#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:16:33 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178428 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/49/4024961.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_4024961
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         'C20 H23 N O2'
_chemical_formula_sum            'C20 H23 N O2'
_chemical_formula_weight         309.39
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                113.131(6)
_cell_angle_beta                 99.921(7)
_cell_angle_gamma                106.091(9)
_cell_formula_units_Z            2
_cell_length_a                   7.3253(7)
_cell_length_b                   11.185(3)
_cell_length_c                   11.3358(18)
_cell_measurement_reflns_used    4468
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.14
_cell_volume                     778.0(3)
_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 0.971
_diffrn_measured_fraction_theta_max 0.971
_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  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0715
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4468
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             332
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .07
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3305
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0445
_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)+(0.0472P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0961
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                2263
_reflns_number_total             3305
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901753z_si_003.cif
_cod_data_source_block           zz
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4024961
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.71904(14) 1.05960(12) 0.46080(12) 0.0241(3) Uani 1 1 d . . .
O2 O 0.98835(15) 0.68295(13) 0.40327(12) 0.0228(3) Uani 1 1 d . . .
N1 N 0.52473(19) 0.83537(15) 0.38629(15) 0.0236(3) Uani 1 1 d . . .
C1 C 0.6837(2) 0.93242(18) 0.39047(17) 0.0188(4) Uani 1 1 d . . .
C2 C 0.4652(2) 0.68359(17) 0.31465(17) 0.0223(4) Uani 1 1 d . . .
H2A H 0.4437 0.6531 0.2170 0.027 Uiso 1 1 calc R . .
H2B H 0.3370 0.6373 0.3251 0.027 Uiso 1 1 calc R . .
C3 C 0.6235(2) 0.63884(17) 0.36862(17) 0.0199(4) Uani 1 1 d . . .
H3 H 0.6664 0.6802 0.4695 0.024 Uiso 1 1 calc R . .
C4 C 0.8066(2) 0.66236(17) 0.31314(16) 0.0189(4) Uani 1 1 d . . .
C5 C 0.8557(2) 0.77117(17) 0.26298(16) 0.0180(4) Uani 1 1 d . . .
C6 C 0.8116(2) 0.89255(17) 0.30363(15) 0.0181(4) Uani 1 1 d . . .
C7 C 0.8939(2) 0.99257(18) 0.26135(17) 0.0221(4) Uani 1 1 d . . .
H7 H 0.8664 1.0759 0.2901 0.027 Uiso 1 1 calc R . .
C8 C 1.0125(2) 0.97259(18) 0.17986(17) 0.0251(4) Uani 1 1 d . . .
H8 H 1.0668 1.0417 0.1531 0.030 Uiso 1 1 calc R . .
C9 C 1.0528(2) 0.85139(18) 0.13679(18) 0.0262(4) Uani 1 1 d . . .
H9 H 1.1321 0.8357 0.0786 0.031 Uiso 1 1 calc R . .
C10 C 0.9767(2) 0.75340(18) 0.17908(17) 0.0239(4) Uani 1 1 d . . .
H10 H 1.0073 0.6714 0.1504 0.029 Uiso 1 1 calc R . .
C11 C 0.6964(2) 0.50597(16) 0.20401(16) 0.0178(4) Uani 1 1 d . . .
H11 H 0.5982 0.5059 0.1308 0.021 Uiso 1 1 calc R . .
C12 C 0.5797(2) 0.47853(17) 0.29734(16) 0.0185(4) Uani 1 1 d . . .
C13 C 0.6918(2) 0.43793(17) 0.39421(17) 0.0210(4) Uani 1 1 d . . .
H13A H 0.8189 0.5178 0.4564 0.025 Uiso 1 1 calc R . .
H13B H 0.6090 0.4167 0.4492 0.025 Uiso 1 1 calc R . .
C14 C 0.7361(2) 0.30999(17) 0.31410(17) 0.0223(4) Uani 1 1 d . . .
H14 H 0.8082 0.2844 0.3780 0.027 Uiso 1 1 calc R . .
C15 C 0.8690(2) 0.34604(18) 0.23227(17) 0.0241(4) Uani 1 1 d . . .
H15A H 0.9960 0.4260 0.2946 0.029 Uiso 1 1 calc R . .
H15B H 0.9019 0.2643 0.1817 0.029 Uiso 1 1 calc R . .
C16 C 0.7605(2) 0.38474(17) 0.13283(17) 0.0211(4) Uani 1 1 d . . .
H16 H 0.8445 0.4063 0.0775 0.025 Uiso 1 1 calc R . .
C17 C 0.5570(2) 0.26121(18) 0.04102(17) 0.0231(4) Uani 1 1 d . . .
H17A H 0.4852 0.2855 -0.0230 0.028 Uiso 1 1 calc R . .
H17B H 0.5813 0.1763 -0.0124 0.028 Uiso 1 1 calc R . .
C18 C 0.4255(2) 0.22943(18) 0.12631(17) 0.0224(4) Uani 1 1 d . . .
H18 H 0.2968 0.1487 0.0642 0.027 Uiso 1 1 calc R . .
C19 C 0.3776(2) 0.35699(17) 0.21052(17) 0.0218(4) Uani 1 1 d . . .
H19A H 0.2974 0.3812 0.1503 0.026 Uiso 1 1 calc R . .
H19B H 0.3010 0.3357 0.2685 0.026 Uiso 1 1 calc R . .
C20 C 0.5382(2) 0.18673(18) 0.21959(17) 0.0240(4) Uani 1 1 d . . .
H20A H 0.5652 0.1035 0.1650 0.029 Uiso 1 1 calc R . .
H20B H 0.4559 0.1619 0.2734 0.029 Uiso 1 1 calc R . .
H1C H 0.460(3) 0.875(2) 0.443(2) 0.043(6) Uiso 1 1 d . . .
H2C H 1.065(3) 0.779(2) 0.452(2) 0.060(7) 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
C4 O2 H2C 108.3(13) . . ?
C1 N1 C2 126.96(15) . . ?
C1 N1 H1C 111.9(12) . . ?
C2 N1 H1C 120.8(12) . . ?
O1 C1 N1 119.41(15) . . ?
O1 C1 C6 119.04(13) . . ?
N1 C1 C6 121.35(15) . . ?
N1 C2 C3 111.00(13) . . ?
N1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
N1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C12 115.93(13) . . ?
C2 C3 C4 113.15(12) . . ?
C12 C3 C4 87.94(12) . . ?
C2 C3 H3 112.5 . . ?
C12 C3 H3 112.5 . . ?
C4 C3 H3 112.5 . . ?
O2 C4 C5 107.78(11) . . ?
O2 C4 C11 111.22(13) . . ?
C5 C4 C11 117.00(13) . . ?
O2 C4 C3 112.97(12) . . ?
C5 C4 C3 120.40(13) . . ?
C11 C4 C3 86.22(11) . . ?
C6 C5 C10 118.10(14) . . ?
C6 C5 C4 126.65(14) . . ?
C10 C5 C4 114.85(14) . . ?
C5 C6 C7 118.88(14) . . ?
C5 C6 C1 127.45(13) . . ?
C7 C6 C1 113.67(14) . . ?
C8 C7 C6 121.67(16) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 119.71(14) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 119.51(15) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C5 122.10(16) . . ?
C9 C10 H10 118.9 . . ?
C5 C10 H10 118.9 . . ?
C16 C11 C12 111.43(13) . . ?
C16 C11 C4 135.36(12) . . ?
C12 C11 C4 89.47(12) . . ?
C16 C11 H11 105.7 . . ?
C12 C11 H11 105.7 . . ?
C4 C11 H11 105.7 . . ?
C19 C12 C11 108.96(13) . . ?
C19 C12 C13 107.94(12) . . ?
C11 C12 C13 112.17(12) . . ?
C19 C12 C3 128.01(13) . . ?
C11 C12 C3 87.49(11) . . ?
C13 C12 C3 110.38(13) . . ?
C14 C13 C12 110.16(13) . . ?
C14 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
C14 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C20 109.12(12) . . ?
C13 C14 C15 108.91(13) . . ?
C20 C14 C15 110.50(14) . . ?
C13 C14 H14 109.4 . . ?
C20 C14 H14 109.4 . . ?
C15 C14 H14 109.4 . . ?
C16 C15 C14 110.29(12) . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C11 C16 C15 112.26(14) . . ?
C11 C16 C17 102.57(12) . . ?
C15 C16 C17 108.80(13) . . ?
C11 C16 H16 111.0 . . ?
C15 C16 H16 111.0 . . ?
C17 C16 H16 111.0 . . ?
C18 C17 C16 111.02(13) . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C20 C18 C17 107.66(12) . . ?
C20 C18 C19 110.26(14) . . ?
C17 C18 C19 112.31(13) . . ?
C20 C18 H18 108.8 . . ?
C17 C18 H18 108.8 . . ?
C19 C18 H18 108.8 . . ?
C12 C19 C18 106.25(12) . . ?
C12 C19 H19A 110.5 . . ?
C18 C19 H19A 110.5 . . ?
C12 C19 H19B 110.5 . . ?
C18 C19 H19B 110.5 . . ?
H19A C19 H19B 108.7 . . ?
C18 C20 C14 108.91(13) . . ?
C18 C20 H20A 109.9 . . ?
C14 C20 H20A 109.9 . . ?
C18 C20 H20B 109.9 . . ?
C14 C20 H20B 109.9 . . ?
H20A C20 H20B 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 1.2490(19) . ?
O2 C4 1.4306(18) . ?
O2 H2C 0.93(2) . ?
N1 C1 1.3330(19) . ?
N1 C2 1.455(2) . ?
N1 H1C 0.91(2) . ?
C1 C6 1.500(2) . ?
C2 C3 1.513(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C12 1.557(2) . ?
C3 C4 1.577(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.518(2) . ?
C4 C11 1.554(2) . ?
C5 C6 1.401(2) . ?
C5 C10 1.403(2) . ?
C6 C7 1.411(2) . ?
C7 C8 1.371(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C16 1.528(2) . ?
C11 C12 1.538(2) . ?
C11 H11 1.0000 . ?
C12 C19 1.529(2) . ?
C12 C13 1.541(2) . ?
C13 C14 1.522(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C20 1.532(2) . ?
C14 C15 1.536(2) . ?
C14 H14 1.0000 . ?
C15 C16 1.534(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.552(2) . ?
C16 H16 1.0000 . ?
C17 C18 1.546(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C20 1.531(2) . ?
C18 C19 1.547(2) . ?
C18 H18 1.0000 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
