#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/53/1515329.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1515329
loop_
_publ_author_name
'Aldemir, Müge'
'Heinemann, Frank W.'
'Kisch, Horst'
_publ_section_title
;
 Photochemical synthesis of N-adamantylhomoallylamines through addition of
 cyclic olefins to imines catalyzed by alumina grafted cadmium sulfide.
;
_journal_issue                   6
_journal_name_full
'Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              908
_journal_page_last               913
_journal_paper_doi               10.1039/c1pp05298e
_journal_volume                  11
_journal_year                    2012
_chemical_formula_moiety         'C34 H42 Cl2 N2'
_chemical_formula_sum            'C34 H42 Cl2 N2'
_chemical_formula_weight         549.60
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                84.03(2)
_cell_angle_beta                 82.99(1)
_cell_angle_gamma                83.11(1)
_cell_formula_units_Z            1
_cell_length_a                   6.4218(5)
_cell_length_b                   10.300(2)
_cell_length_c                   10.942(1)
_cell_measurement_reflns_used    36
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.00
_cell_measurement_theta_min      6.00
_cell_volume                     710.22(16)
_computing_cell_refinement       'EVALCCD (Duisenberg, 2003)'
_computing_data_collection       'COLLECT (Bruker-Nonius, 2002)'
_computing_data_reduction        'EVALCCD (Duisenberg, 2003)'
_computing_molecular_graphics    'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_publication_material  'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_structure_refinement  'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_structure_solution    'SHELXTL 6.12 (Bruker AXS, 2002)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method
;
ω-rotations with 2.00 ° and 380 sec per frame
;
_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  0.0809
_diffrn_reflns_av_sigmaI/netI    0.0602
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13053
_diffrn_reflns_theta_full        26.36
_diffrn_reflns_theta_max         26.36
_diffrn_reflns_theta_min         3.22
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker AXS, 2002'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             294
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.557
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2889
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0864
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0508P)²+0.7014P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1288
_reflns_number_gt                2050
_reflns_number_total             2889
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1pp05298e.txt
_cod_data_source_block           ma0504
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1515329
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
Cl1 Cl -0.09541(12) 0.68468(7) 0.97141(6) 0.0281(2) Uani 1 1 d
N1 N 0.3529(3) 0.6097(2) 0.3864(2) 0.0171(5) Uani 1 1 d
H1 H 0.431(5) 0.571(3) 0.330(3) 0.021 Uiso 1 1 d
C1 C 0.3228(4) 0.7497(2) 0.3364(2) 0.0132(5) Uani 1 1 d
C2 C 0.3092(5) 0.7491(3) 0.1968(2) 0.0191(6) Uani 1 1 d
H2A H 0.445(5) 0.708(3) 0.159(3) 0.023 Uiso 1 1 d
H2B H 0.194(5) 0.695(3) 0.181(3) 0.023 Uiso 1 1 d
C3 C 0.2658(4) 0.8897(3) 0.1353(2) 0.0205(6) Uani 1 1 d
H3 H 0.263(5) 0.883(3) 0.048(3) 0.025 Uiso 1 1 d
C4 C 0.4466(4) 0.9674(3) 0.1537(2) 0.0212(6) Uani 1 1 d
H4A H 0.579(5) 0.922(3) 0.114(3) 0.025 Uiso 1 1 d
H4B H 0.423(4) 1.059(3) 0.111(3) 0.025 Uiso 1 1 d
C5 C 0.4607(4) 0.9725(3) 0.2915(2) 0.0188(6) Uani 1 1 d
H5 H 0.571(5) 1.019(3) 0.303(3) 0.023 Uiso 1 1 d
C6 C 0.5023(4) 0.8311(3) 0.3532(2) 0.0182(6) Uani 1 1 d
H6A H 0.507(4) 0.835(3) 0.445(3) 0.022 Uiso 1 1 d
H6B H 0.645(5) 0.788(3) 0.313(3) 0.022 Uiso 1 1 d
C7 C 0.1129(4) 0.8176(3) 0.3958(2) 0.0173(6) Uani 1 1 d
H7A H -0.003(5) 0.762(3) 0.385(3) 0.021 Uiso 1 1 d
H7B H 0.116(4) 0.819(3) 0.490(3) 0.021 Uiso 1 1 d
C8 C 0.0714(4) 0.9585(3) 0.3336(2) 0.0189(6) Uani 1 1 d
H8 H -0.054(5) 1.002(3) 0.370(3) 0.023 Uiso 1 1 d
C9 C 0.2518(4) 1.0370(3) 0.3507(3) 0.0210(6) Uani 1 1 d
H9A H 0.260(5) 1.047(3) 0.433(3) 0.025 Uiso 1 1 d
H9B H 0.226(5) 1.126(3) 0.309(3) 0.025 Uiso 1 1 d
C10 C 0.0569(4) 0.9528(3) 0.1968(3) 0.0210(6) Uani 1 1 d
H10A H -0.051(5) 0.905(3) 0.184(3) 0.025 Uiso 1 1 d
H10B H 0.025(5) 1.045(3) 0.152(3) 0.025 Uiso 1 1 d
C11 C 0.4631(4) 0.5748(3) 0.4964(2) 0.0211(6) Uani 1 1 d
H11 H 0.588(5) 0.623(3) 0.491(3) 0.025 Uiso 1 1 d
C12 C 0.3186(4) 0.6061(3) 0.6140(2) 0.0206(6) Uani 1 1 d
C13 C 0.1226(4) 0.5564(3) 0.6420(3) 0.0240(6) Uani 1 1 d
H13 H 0.067(5) 0.504(3) 0.583(3) 0.029 Uiso 1 1 d
C14 C -0.0048(5) 0.5784(3) 0.7522(3) 0.0229(6) Uani 1 1 d
H14 H -0.137(5) 0.547(3) 0.771(3) 0.028 Uiso 1 1 d
C15 C 0.0658(4) 0.6525(3) 0.8348(2) 0.0205(6) Uani 1 1 d
C16 C 0.2587(5) 0.7021(3) 0.8101(3) 0.0254(6) Uani 1 1 d
H16 H 0.302(5) 0.752(3) 0.868(3) 0.030 Uiso 1 1 d
C17 C 0.3832(5) 0.6791(3) 0.6998(3) 0.0241(6) Uani 1 1 d
H17 H 0.524(5) 0.714(3) 0.684(3) 0.029 Uiso 1 1 d
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'
Cl Cl 0.1484 0.1585 '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
C11 N1 C1 119.2(2) . .
C11 N1 H1 104(2) . .
C1 N1 H1 105(2) . .
N1 C1 C2 106.27(19) . .
N1 C1 C6 114.8(2) . .
C2 C1 C6 108.3(2) . .
N1 C1 C7 110.3(2) . .
C2 C1 C7 108.5(2) . .
C6 C1 C7 108.5(2) . .
C1 C2 C3 111.2(2) . .
C1 C2 H2A 108.1(17) . .
C3 C2 H2A 109.5(17) . .
C1 C2 H2B 111.1(16) . .
C3 C2 H2B 109.1(17) . .
H2A C2 H2B 108(2) . .
C10 C3 C4 110.2(2) . .
C10 C3 C2 108.6(2) . .
C4 C3 C2 108.5(2) . .
C10 C3 H3 112.5(18) . .
C4 C3 H3 109.6(17) . .
C2 C3 H3 107.3(17) . .
C5 C4 C3 110.2(2) . .
C5 C4 H4A 110.0(17) . .
C3 C4 H4A 107.6(17) . .
C5 C4 H4B 111.0(16) . .
C3 C4 H4B 109.1(16) . .
H4A C4 H4B 109(2) . .
C9 C5 C4 108.9(2) . .
C9 C5 C6 109.2(2) . .
C4 C5 C6 109.3(2) . .
C9 C5 H5 110.4(17) . .
C4 C5 H5 110.2(18) . .
C6 C5 H5 108.7(18) . .
C1 C6 C5 110.4(2) . .
C1 C6 H6A 108.3(16) . .
C5 C6 H6A 108.8(16) . .
C1 C6 H6B 109.8(15) . .
C5 C6 H6B 108.9(16) . .
H6A C6 H6B 111(2) . .
C1 C7 C8 110.0(2) . .
C1 C7 H7A 107.6(16) . .
C8 C7 H7A 111.5(17) . .
C1 C7 H7B 110.5(16) . .
C8 C7 H7B 110.4(16) . .
H7A C7 H7B 107(2) . .
C10 C8 C9 110.0(2) . .
C10 C8 C7 109.4(2) . .
C9 C8 C7 109.3(2) . .
C10 C8 H8 109.4(18) . .
C9 C8 H8 107.6(17) . .
C7 C8 H8 111.1(18) . .
C5 C9 C8 110.2(2) . .
C5 C9 H9A 110.5(19) . .
C8 C9 H9A 112.1(18) . .
C5 C9 H9B 108.0(17) . .
C8 C9 H9B 108.9(17) . .
H9A C9 H9B 107(2) . .
C8 C10 C3 109.8(2) . .
C8 C10 H10A 111.5(18) . .
C3 C10 H10A 109.1(18) . .
C8 C10 H10B 112.1(16) . .
C3 C10 H10B 108.1(16) . .
H10A C10 H10B 106(2) . .
N1 C11 C12 111.2(2) . .
N1 C11 C11 108.3(3) . 2_666
C12 C11 C11 109.3(3) . 2_666
N1 C11 H11 110.5(17) . .
C12 C11 H11 108.5(16) . .
C11 C11 H11 109.0(18) 2_666 .
C17 C12 C13 117.9(3) . .
C17 C12 C11 120.8(2) . .
C13 C12 C11 121.3(2) . .
C14 C13 C12 121.6(3) . .
C14 C13 H13 117.0(17) . .
C12 C13 H13 121.3(17) . .
C15 C14 C13 118.4(3) . .
C15 C14 H14 119.6(18) . .
C13 C14 H14 122.0(18) . .
C16 C15 C14 121.2(3) . .
C16 C15 Cl1 119.8(2) . .
C14 C15 Cl1 118.9(2) . .
C15 C16 C17 119.4(3) . .
C15 C16 H16 119.3(19) . .
C17 C16 H16 121.3(19) . .
C16 C17 C12 121.4(3) . .
C16 C17 H17 118.3(17) . .
C12 C17 H17 120.3(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C15 1.749(3) .
N1 C11 1.462(3) .
N1 C1 1.487(3) .
N1 H1 0.85(3) .
C1 C2 1.541(3) .
C1 C6 1.543(3) .
C1 C7 1.544(3) .
C2 C3 1.541(4) .
C2 H2A 0.99(3) .
C2 H2B 1.01(3) .
C3 C10 1.529(4) .
C3 C4 1.530(4) .
C3 H3 0.96(3) .
C4 C5 1.529(4) .
C4 H4A 0.99(3) .
C4 H4B 1.01(3) .
C5 C9 1.524(4) .
C5 C6 1.548(4) .
C5 H5 0.93(3) .
C6 H6A 1.01(3) .
C6 H6B 1.04(3) .
C7 C8 1.545(4) .
C7 H7A 1.01(3) .
C7 H7B 1.03(3) .
C8 C10 1.519(4) .
C8 C9 1.530(4) .
C8 H8 0.93(3) .
C9 H9A 0.93(3) .
C9 H9B 0.98(3) .
C10 H10A 0.93(3) .
C10 H10B 1.03(3) .
C11 C12 1.531(4) .
C11 C11 1.553(5) 2_666
C11 H11 0.99(3) .
C12 C17 1.391(4) .
C12 C13 1.403(4) .
C13 C14 1.394(4) .
C13 H13 1.01(3) .
C14 C15 1.390(4) .
C14 H14 0.94(3) .
C15 C16 1.382(4) .
C16 C17 1.389(4) .
C16 H16 0.94(3) .
C17 H17 1.00(3) .
