#------------------------------------------------------------------------------
#$Date: 2016-08-05 09:31:05 +0300 (Fri, 05 Aug 2016) $
#$Revision: 185006 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/76/2107630.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_2107630
loop_
_publ_author_name
'Mohamed, Sharmarke'
'Karothu, Durga Prasad'
'Naumov, Panče'
_publ_section_title
;
 Using crystal structure prediction to rationalize the hydration
 propensities of substituted adamantane hydrochloride salts
;
_journal_coeditor_code           GP5081
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              551
_journal_page_last               561
_journal_paper_doi               10.1107/S2052520616006326
_journal_volume                  72
_journal_year                    2016
_chemical_formula_sum            'C11 H19 N'
_chemical_formula_weight         165.27
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 96.509(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.2451(8)
_cell_length_b                   6.5202(6)
_cell_length_c                   8.8214(8)
_cell_measurement_reflns_used    13304
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      2.3
_cell_volume                     471.18(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13304
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.324
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             184
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     68
_refine_ls_number_reflns         1000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0758
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0290P)²+0.7802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1456
_refine_ls_wR_factor_ref         0.1478
_reflns_Friedel_coverage         0.000
_reflns_number_gt                913
_reflns_number_total             1000
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            gp5081sup1.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 2107630--2107631.cif.'
_cod_database_code               2107630
_cod_database_fobs_code          2107630
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8170(3) 0.7500 0.6373(3) 0.0174(6) Uani 1 2 d S T P . .
N1 N 0.9161(3) 0.7500 0.5081(3) 0.0294(7) Uani 1 2 d S T P . .
H1 H 0.978(6) 0.873(7) 0.515(6) 0.035 Uiso 0.5 1 d . U P . .
C2 C 0.7096(3) 0.5601(3) 0.6384(3) 0.0300(5) Uani 1 1 d . . . . .
H2A H 0.7783 0.4354 0.6390 0.036 Uiso 1 1 calc R U . . .
H2B H 0.6309 0.5575 0.5449 0.036 Uiso 1 1 calc R U . . .
C6 C 0.9379(3) 0.7500 0.7826(3) 0.0354(9) Uani 1 2 d S T P . .
H6A H 1.0085 0.6270 0.7840 0.043 Uiso 0.5 1 calc R U P . .
H6B H 1.0085 0.8730 0.7840 0.043 Uiso 0.5 1 calc R U P . .
C3 C 0.6169(3) 0.5609(4) 0.7793(3) 0.0409(7) Uani 1 1 d . . . . .
H3 H 0.5472 0.4352 0.7787 0.049 Uiso 1 1 calc R U . . .
C5 C 0.8452(4) 0.7500 0.9237(3) 0.0551(14) Uani 1 2 d S T P . .
H5 H 0.9251 0.7500 1.0178 0.066 Uiso 1 2 calc R U P . .
C7 C 0.5094(4) 0.7500 0.7764(4) 0.0381(9) Uani 1 2 d S T P . .
H7A H 0.4471 0.7500 0.8660 0.046 Uiso 1 2 calc R U P . .
H7B H 0.4306 0.7500 0.6830 0.046 Uiso 1 2 calc R U P . .
C8 C 0.8244(4) 0.7500 0.3558(3) 0.0404(10) Uani 1 2 d S T P . .
H8A H 0.7416 0.8584 0.3498 0.061 Uiso 0.5 1 calc R U P A -1
H8B H 0.7710 0.6168 0.3366 0.061 Uiso 0.5 1 calc R U P A -1
H8C H 0.8993 0.7748 0.2791 0.061 Uiso 0.5 1 calc R U P A -1
C4 C 0.7388(3) 0.5618(6) 0.9229(3) 0.0666(11) Uani 1 1 d . . . . .
H4A H 0.6796 0.5616 1.0145 0.080 Uiso 1 1 calc R U . . .
H4B H 0.8074 0.4370 0.9256 0.080 Uiso 1 1 calc R U . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N1 C1 C2 112.21(14) . 4_575
N1 C1 C2 112.21(14) . .
C2 C1 C2 108.8(2) 4_575 .
N1 C1 C6 106.3(2) . .
C2 C1 C6 108.56(15) 4_575 .
C2 C1 C6 108.56(15) . .
C8 N1 C1 115.8(2) . .
C1 C2 C3 110.26(19) . .
C5 C6 C1 110.0(2) . .
C7 C3 C4 109.9(3) . .
C7 C3 C2 109.5(2) . .
C4 C3 C2 109.35(19) . .
C4 C5 C4 108.9(3) 4_575 .
C4 C5 C6 109.87(19) 4_575 .
C4 C5 C6 109.87(19) . .
C3 C7 C3 108.7(2) . 4_575
C5 C4 C3 109.6(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.476(3) .
C1 C2 1.523(2) 4_575
C1 C2 1.523(2) .
C1 C6 1.533(4) .
N1 C8 1.465(4) .
C2 C3 1.532(3) .
C6 C5 1.532(4) .
C3 C7 1.517(3) .
C3 C4 1.525(4) .
C5 C4 1.508(4) 4_575
C5 C4 1.508(4) .
C7 C3 1.517(3) 4_575
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_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 C1 N1 C8 -61.46(16) 4_575 .
C2 C1 N1 C8 61.46(16) . .
C6 C1 N1 C8 180.000(1) . .
N1 C1 C2 C3 176.67(19) . .
C2 C1 C2 C3 -58.5(3) 4_575 .
C6 C1 C2 C3 59.5(2) . .
N1 C1 C6 C5 180.000(1) . .
C2 C1 C6 C5 59.08(14) 4_575 .
C2 C1 C6 C5 -59.08(14) . .
C1 C2 C3 C7 60.3(2) . .
C1 C2 C3 C4 -60.1(3) . .
C1 C6 C5 C4 -59.89(19) . 4_575
C1 C6 C5 C4 59.89(19) . .
C4 C3 C7 C3 59.2(3) . 4_575
C2 C3 C7 C3 -60.8(3) . 4_575
C4 C5 C4 C3 60.6(4) 4_575 .
C6 C5 C4 C3 -59.8(3) . .
C7 C3 C4 C5 -60.5(3) . .
C2 C3 C4 C5 59.7(3) . .
