#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:16:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178428 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/49/4024962.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_4024962
loop_
_publ_author_name
'Margareta Horvat'
'Helmut Görner'
'Klaus-Dieter Warzecha'
'Jörg Neudörfl'
'Axel G. Griesbeck'
'Kata Mlinarić-Majerski'
'Nikola Basarić'
_publ_section_title
;
Photoinitiated Domino Reactions: N-(Adamantyl)phthalimides
and N-(Adamantylalkyl)phthalimides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8219
_journal_page_last               8231
_journal_paper_doi               10.1021/jo901753z
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C19 H21 N O2'
_chemical_formula_sum            'C19 H21 N O2'
_chemical_formula_weight         295.37
_chemical_name_systematic
; 
 ? 
;
_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                 97.080(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   9.8165(7)
_cell_length_b                   9.4087(7)
_cell_length_c                   32.345(2)
_cell_measurement_reflns_used    6601
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.54
_cell_volume                     2964.6(4)
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_collection       'Nonius COLLECT'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/Omega-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  0.0566
_diffrn_reflns_av_sigmaI/netI    0.1259
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            6601
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.829
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3112
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.829
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0418
_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)+(0.0262P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0732
_refine_ls_wR_factor_ref         0.0850
_reflns_number_gt                1580
_reflns_number_total             3112
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901753z_si_004.cif
_cod_data_source_block           zim-mgh517n
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4024962
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_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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.57185(13) 0.25288(12) -0.01372(4) 0.0214(3) Uani 1 1 d . . .
O2 O 0.48793(13) 0.09186(13) 0.11582(4) 0.0241(3) Uani 1 1 d . . .
N1 N 0.68519(17) 0.29971(16) 0.05038(4) 0.0176(4) Uani 1 1 d . . .
C1 C 0.5706(2) 0.29320(18) 0.02268(6) 0.0189(5) Uani 1 1 d . . .
C2 C 0.69252(19) 0.37930(17) 0.08959(5) 0.0180(5) Uani 1 1 d . . .
H2A H 0.6332 0.4644 0.0852 0.022 Uiso 1 1 calc R . .
H2B H 0.7880 0.4122 0.0974 0.022 Uiso 1 1 calc R . .
C3 C 0.64745(19) 0.29097(18) 0.12580(5) 0.0159(4) Uani 1 1 d . . .
C4 C 0.51653(19) 0.2141(2) 0.10757(5) 0.0179(5) Uani 1 1 d . . .
C5 C 0.41293(19) 0.29656(18) 0.07852(5) 0.0169(4) Uani 1 1 d . . .
C6 C 0.43914(19) 0.33347(18) 0.03847(6) 0.0169(4) Uani 1 1 d . . .
C7 C 0.3374(2) 0.39907(18) 0.01134(6) 0.0204(5) Uani 1 1 d . . .
H7 H 0.3543 0.4212 -0.0162 0.024 Uiso 1 1 calc R . .
C8 C 0.2117(2) 0.43241(18) 0.02408(6) 0.0251(5) Uani 1 1 d . . .
H8 H 0.1440 0.4808 0.0058 0.030 Uiso 1 1 calc R . .
C9 C 0.1852(2) 0.39463(18) 0.06383(6) 0.0252(5) Uani 1 1 d . . .
H9 H 0.0988 0.4164 0.0726 0.030 Uiso 1 1 calc R . .
C10 C 0.2846(2) 0.32530(18) 0.09068(6) 0.0218(5) Uani 1 1 d . . .
H10 H 0.2649 0.2972 0.1175 0.026 Uiso 1 1 calc R . .
C11 C 0.76180(19) 0.19068(18) 0.14608(5) 0.0191(5) Uani 1 1 d . . .
H11 H 0.7885 0.1230 0.1246 0.023 Uiso 1 1 calc R . .
C12 C 0.71607(19) 0.10600(19) 0.18288(5) 0.0235(5) Uani 1 1 d . . .
H12A H 0.6377 0.0438 0.1727 0.028 Uiso 1 1 calc R . .
H12B H 0.7924 0.0450 0.1954 0.028 Uiso 1 1 calc R . .
C13 C 0.6738(2) 0.2088(2) 0.21583(5) 0.0246(5) Uani 1 1 d . . .
H13 H 0.6404 0.1535 0.2390 0.029 Uiso 1 1 calc R . .
C14 C 0.55912(19) 0.30751(19) 0.19617(5) 0.0231(5) Uani 1 1 d . . .
H14A H 0.4777 0.2503 0.1854 0.028 Uiso 1 1 calc R . .
H14B H 0.5321 0.3734 0.2176 0.028 Uiso 1 1 calc R . .
C15 C 0.60829(19) 0.39294(18) 0.16040(5) 0.0187(5) Uani 1 1 d . . .
H15 H 0.5334 0.4582 0.1483 0.022 Uiso 1 1 calc R . .
C16 C 0.73472(19) 0.4811(2) 0.17774(5) 0.0219(5) Uani 1 1 d . . .
H16A H 0.7093 0.5483 0.1990 0.026 Uiso 1 1 calc R . .
H16B H 0.7676 0.5369 0.1550 0.026 Uiso 1 1 calc R . .
C17 C 0.8499(2) 0.38192(19) 0.19731(5) 0.0217(5) Uani 1 1 d . . .
H17 H 0.9319 0.4397 0.2083 0.026 Uiso 1 1 calc R . .
C18 C 0.88888(19) 0.27798(19) 0.16419(5) 0.0211(5) Uani 1 1 d . . .
H18A H 0.9618 0.2130 0.1768 0.025 Uiso 1 1 calc R . .
H18B H 0.9251 0.3315 0.1415 0.025 Uiso 1 1 calc R . .
C19 C 0.7987(2) 0.2982(2) 0.23304(5) 0.0271(5) Uani 1 1 d . . .
H19A H 0.8726 0.2353 0.2462 0.033 Uiso 1 1 calc R . .
H19B H 0.7729 0.3647 0.2545 0.033 Uiso 1 1 calc R . .
H1 H 0.7642(19) 0.2760(19) 0.0398(5) 0.034(6) 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 123.02(16) . . ?
C1 N1 H1 114.6(12) . . ?
C2 N1 H1 119.7(12) . . ?
O1 C1 N1 122.67(17) . . ?
O1 C1 C6 120.85(17) . . ?
N1 C1 C6 116.46(16) . . ?
N1 C2 C3 113.13(13) . . ?
N1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C2 105.54(15) . . ?
C4 C3 C11 113.95(15) . . ?
C2 C3 C11 112.86(15) . . ?
C4 C3 C15 107.36(14) . . ?
C2 C3 C15 109.42(14) . . ?
C11 C3 C15 107.53(14) . . ?
O2 C4 C5 117.67(17) . . ?
O2 C4 C3 124.51(18) . . ?
C5 C4 C3 117.79(16) . . ?
C10 C5 C6 119.40(17) . . ?
C10 C5 C4 119.16(16) . . ?
C6 C5 C4 121.20(16) . . ?
C7 C6 C5 119.74(18) . . ?
C7 C6 C1 118.71(17) . . ?
C5 C6 C1 121.35(17) . . ?
C8 C7 C6 120.68(18) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 119.54(19) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 H8 120.2 . . ?
C10 C9 C8 120.18(19) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C5 120.38(18) . . ?
C9 C10 H10 119.8 . . ?
C5 C10 H10 119.8 . . ?
C12 C11 C18 106.23(14) . . ?
C12 C11 C3 112.11(15) . . ?
C18 C11 C3 110.20(14) . . ?
C12 C11 H11 109.4 . . ?
C18 C11 H11 109.4 . . ?
C3 C11 H11 109.4 . . ?
C13 C12 C11 109.85(15) . . ?
C13 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C19 C13 C12 108.97(16) . . ?
C19 C13 C14 109.35(15) . . ?
C12 C13 C14 109.93(15) . . ?
C19 C13 H13 109.5 . . ?
C12 C13 H13 109.5 . . ?
C14 C13 H13 109.5 . . ?
C15 C14 C13 110.28(15) . . ?
C15 C14 H14A 109.6 . . ?
C13 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C13 C14 H14B 109.6 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 108.76(15) . . ?
C14 C15 C3 110.33(14) . . ?
C16 C15 C3 109.52(15) . . ?
C14 C15 H15 109.4 . . ?
C16 C15 H15 109.4 . . ?
C3 C15 H15 109.4 . . ?
C15 C16 C17 109.96(15) . . ?
C15 C16 H16A 109.7 . . ?
C17 C16 H16A 109.7 . . ?
C15 C16 H16B 109.7 . . ?
C17 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C18 C17 C19 109.39(15) . . ?
C18 C17 C16 109.46(15) . . ?
C19 C17 C16 109.18(16) . . ?
C18 C17 H17 109.6 . . ?
C19 C17 H17 109.6 . . ?
C16 C17 H17 109.6 . . ?
C17 C18 C11 110.12(15) . . ?
C17 C18 H18A 109.6 . . ?
C11 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
C11 C18 H18B 109.6 . . ?
H18A C18 H18B 108.2 . . ?
C13 C19 C17 109.26(15) . . ?
C13 C19 H19A 109.8 . . ?
C17 C19 H19A 109.8 . . ?
C13 C19 H19B 109.8 . . ?
C17 C19 H19B 109.8 . . ?
H19A C19 H19B 108.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2383(19) . ?
O2 C4 1.2209(19) . ?
N1 C1 1.350(2) . ?
N1 C2 1.4670(19) . ?
N1 H1 0.913(17) . ?
C1 C6 1.494(2) . ?
C2 C3 1.545(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.528(3) . ?
C3 C11 1.549(2) . ?
C3 C15 1.558(2) . ?
C4 C5 1.511(2) . ?
C5 C10 1.392(2) . ?
C5 C6 1.395(2) . ?
C6 C7 1.390(2) . ?
C7 C8 1.384(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.544(2) . ?
C11 C18 1.547(2) . ?
C11 H11 1.0000 . ?
C12 C13 1.534(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C19 1.533(2) . ?
C13 C14 1.535(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.535(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.540(2) . ?
C15 H15 1.0000 . ?
C16 C17 1.540(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.533(2) . ?
C17 C19 1.534(2) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
