#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/41/2234186.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_2234186
loop_
_publ_author_name
'Jin, Xu-Dong'
'Yin, Xue-Yue'
'Wang, Hai-Bo'
'Chang, Xiao-Hong'
'Jin, Yue-Hong'
_publ_section_title
;
 (E)-N-Benzylideneadamantan-1-amine
;
_journal_coeditor_code           GK2442
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1130
_journal_paper_doi               10.1107/S1600536812011415
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H21 N'
_chemical_formula_moiety         'C17 H21 N'
_chemical_formula_sum            'C17 H21 N'
_chemical_formula_weight         239.35
_chemical_melting_point          320.5
_chemical_name_systematic
;
(E)-N-Benzylideneadamantan-1-amine
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.480(2)
_cell_length_b                   7.141(2)
_cell_length_c                   29.674(11)
_cell_measurement_reflns_used    5300
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.8
_cell_volume                     1373.1(8)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'SMART (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω 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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            4971
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.75
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.158
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate-shaped
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.172
_refine_ls_abs_structure_details
;Flack, H. D. (1983). Acta Cryst. A39,
876--881, 1097 Friedel pairs
;
_refine_ls_abs_structure_Flack   -3(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0759
_refine_ls_R_factor_gt           0.0495
_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/[σ²(Fo²)+(0.0708P)²+0.1812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1399
_reflns_number_gt                1981
_reflns_number_total             2726
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2442.cif
_cod_data_source_block           I
_cod_database_code               2234186
_cod_database_fobs_code          2234186
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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
_atom_site_symmetry_multiplicity
C C1 0.1858(3) 0.5833(3) 0.14354(7) 0.0372(5) Uani d . 1 1
C C2 0.3828(4) 0.5357(3) 0.16995(9) 0.0527(6) Uani d . 1 1
H H2A 0.4953 0.5136 0.1490 0.063 Uiso calc R 1 1
H H2B 0.3611 0.4222 0.1872 0.063 Uiso calc R 1 1
C C3 0.2221(4) 0.7625(3) 0.11730(8) 0.0479(6) Uani d . 1 1
H H3A 0.0982 0.7945 0.1007 0.057 Uiso calc R 1 1
H H3B 0.3326 0.7429 0.0957 0.057 Uiso calc R 1 1
C C4 0.0121(3) 0.6168(3) 0.17747(8) 0.0456(6) Uani d . 1 1
H H4A -0.0107 0.5039 0.1950 0.055 Uiso calc R 1 1
H H4B -0.1146 0.6458 0.1615 0.055 Uiso calc R 1 1
C C5 0.0674(4) 0.7804(3) 0.20945(7) 0.0474(6) Uani d . 1 1
H H5 -0.0453 0.8011 0.2309 0.057 Uiso calc R 1 1
C C6 0.2638(4) 0.7272(4) 0.23476(9) 0.0570(7) Uani d . 1 1
H H6A 0.2993 0.8259 0.2558 0.068 Uiso calc R 1 1
H H6B 0.2402 0.6133 0.2518 0.068 Uiso calc R 1 1
C C7 0.4407(4) 0.6974(3) 0.20206(8) 0.0514(6) Uani d . 1 1
H H7 0.5671 0.6664 0.2186 0.062 Uiso calc R 1 1
C C8 0.4736(4) 0.8731(3) 0.17412(9) 0.0539(6) Uani d . 1 1
H H8A 0.5135 0.9755 0.1938 0.065 Uiso calc R 1 1
H H8B 0.5848 0.8522 0.1528 0.065 Uiso calc R 1 1
C C9 0.2796(4) 0.9257(3) 0.14885(8) 0.0471(6) Uani d . 1 1
H H9 0.3031 1.0398 0.1312 0.057 Uiso calc R 1 1
C C10 0.1026(4) 0.9556(3) 0.18180(9) 0.0513(6) Uani d . 1 1
H H10A 0.1348 1.0595 0.2016 0.062 Uiso calc R 1 1
H H10B -0.0221 0.9865 0.1653 0.062 Uiso calc R 1 1
C C11 -0.0168(4) 0.3554(3) 0.10652(8) 0.0476(6) Uani d . 1 1
H H11 -0.1226 0.3914 0.1258 0.057 Uiso calc R 1 1
C C12 -0.0603(4) 0.2091(3) 0.07252(8) 0.0490(6) Uani d . 1 1
C C13 0.0838(4) 0.1560(3) 0.04071(8) 0.0554(7) Uani d . 1 1
H H13 0.2133 0.2121 0.0404 0.067 Uiso calc R 1 1
C C14 0.0355(6) 0.0188(3) 0.00920(9) 0.0681(8) Uani d . 1 1
H H14 0.1322 -0.0163 -0.0124 0.082 Uiso calc R 1 1
C C15 -0.1551(6) -0.0648(4) 0.00991(9) 0.0731(9) Uani d . 1 1
H H15 -0.1870 -0.1577 -0.0109 0.088 Uiso calc R 1 1
C C16 -0.2978(5) -0.0116(4) 0.04126(10) 0.0740(9) Uani d . 1 1
H H16 -0.4274 -0.0676 0.0416 0.089 Uiso calc R 1 1
C C17 -0.2507(4) 0.1241(4) 0.07226(9) 0.0610(7) Uani d . 1 1
H H17 -0.3490 0.1592 0.0935 0.073 Uiso calc R 1 1
N N1 0.1537(3) 0.4325(2) 0.11053(6) 0.0480(5) Uani d . 1 1
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
N1 C1 C3 107.34(16)
N1 C1 C4 116.69(17)
C3 C1 C4 108.70(17)
N1 C1 C2 107.17(17)
C3 C1 C2 108.63(18)
C4 C1 C2 108.08(18)
C1 C2 C7 110.58(18)
C1 C2 H2A 109.5
C7 C2 H2A 109.5
C1 C2 H2B 109.5
C7 C2 H2B 109.5
H2A C2 H2B 108.1
C1 C3 C9 111.33(17)
C1 C3 H3A 109.4
C9 C3 H3A 109.4
C1 C3 H3B 109.4
C9 C3 H3B 109.4
H3A C3 H3B 108.0
C1 C4 C5 110.57(18)
C1 C4 H4A 109.5
C5 C4 H4A 109.5
C1 C4 H4B 109.5
C5 C4 H4B 109.5
H4A C4 H4B 108.1
C10 C5 C6 110.3(2)
C10 C5 C4 109.06(18)
C6 C5 C4 107.88(19)
C10 C5 H5 109.9
C6 C5 H5 109.9
C4 C5 H5 109.9
C7 C6 C5 110.52(19)
C7 C6 H6A 109.5
C5 C6 H6A 109.5
C7 C6 H6B 109.5
C5 C6 H6B 109.5
H6A C6 H6B 108.1
C6 C7 C8 109.8(2)
C6 C7 C2 108.4(2)
C8 C7 C2 108.38(19)
C6 C7 H7 110.1
C8 C7 H7 110.1
C2 C7 H7 110.1
C9 C8 C7 111.07(19)
C9 C8 H8A 109.4
C7 C8 H8A 109.4
C9 C8 H8B 109.4
C7 C8 H8B 109.4
H8A C8 H8B 108.0
C8 C9 C10 110.04(19)
C8 C9 C3 108.37(19)
C10 C9 C3 108.3(2)
C8 C9 H9 110.0
C10 C9 H9 110.0
C3 C9 H9 110.0
C5 C10 C9 110.23(19)
C5 C10 H10A 109.6
C9 C10 H10A 109.6
C5 C10 H10B 109.6
C9 C10 H10B 109.6
H10A C10 H10B 108.1
N1 C11 C12 123.3(2)
N1 C11 H11 118.4
C12 C11 H11 118.4
C17 C12 C13 118.8(2)
C17 C12 C11 119.1(2)
C13 C12 C11 122.1(2)
C12 C13 C14 120.1(3)
C12 C13 H13 120.0
C14 C13 H13 120.0
C15 C14 C13 120.0(3)
C15 C14 H14 120.0
C13 C14 H14 120.0
C16 C15 C14 119.9(3)
C16 C15 H15 120.0
C14 C15 H15 120.0
C15 C16 C17 120.2(3)
C15 C16 H16 119.9
C17 C16 H16 119.9
C16 C17 C12 121.1(3)
C16 C17 H17 119.5
C12 C17 H17 119.5
C11 N1 C1 120.97(19)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.471(3)
C1 C3 1.516(3)
C1 C4 1.529(3)
C1 C2 1.536(3)
C2 C7 1.543(3)
C2 H2A 0.9700
C2 H2B 0.9700
C3 C9 1.541(3)
C3 H3A 0.9700
C3 H3B 0.9700
C4 C5 1.547(3)
C4 H4A 0.9700
C4 H4B 0.9700
C5 C10 1.514(3)
C5 C6 1.525(3)
C5 H5 0.9800
C6 C7 1.517(3)
C6 H6A 0.9700
C6 H6B 0.9700
C7 C8 1.519(3)
C7 H7 0.9800
C8 C9 1.511(3)
C8 H8A 0.9700
C8 H8B 0.9700
C9 C10 1.522(3)
C9 H9 0.9800
C10 H10A 0.9700
C10 H10B 0.9700
C11 N1 1.240(3)
C11 C12 1.480(3)
C11 H11 0.9300
C12 C17 1.375(3)
C12 C13 1.381(3)
C13 C14 1.390(3)
C13 H13 0.9300
C14 C15 1.371(5)
C14 H14 0.9300
C15 C16 1.366(4)
C15 H15 0.9300
C16 C17 1.371(4)
C16 H16 0.9300
C17 H17 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 275749
