#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2203502.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_2203502 loop_ _publ_author_name 'Crane, Jonathan D.' 'Rogerson, Eleanor' _publ_section_title ; 2-(Adamantan-1-yl)-5-methylbenzo[d][1,3]oxazin-4-one ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o669 _journal_page_last o670 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C19 H21 N O2' _chemical_formula_moiety 'C19 H21 N O2' _chemical_formula_sum 'C19 H21 N O2' _chemical_formula_weight 295.37 _chemical_name_systematic ; 2-(Adamantan-1-yl)-5-methylbenzo[d][1,3]oxazin-4-one ; _space_group_IT_number 11 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yb' _symmetry_space_group_name_H-M 'P 1 21/m 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 104.275(11) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 8.3514(12) _cell_length_b 6.7324(5) _cell_length_c 13.3203(19) _cell_measurement_reflns_used 8117 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 34.71 _cell_measurement_theta_min 2.52 _cell_volume 725.81(16) _computing_cell_refinement X-AREA _computing_data_collection 'X-AREA (Stoe & Cie, 2001)' _computing_data_reduction 'X-RED (Stoe & Cie, 2001)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)' _computing_publication_material WinGX _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'X-STEP32 (Stoe & Cie, 2001) and WinGX (Farrugia, 1999)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Stoe IPDS-II area-detector' _diffrn_measurement_method '\f and \w' _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 0.0611 _diffrn_reflns_av_sigmaI/netI 0.0522 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 10561 _diffrn_reflns_theta_full 34.71 _diffrn_reflns_theta_max 34.71 _diffrn_reflns_theta_min 2.52 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 316 _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.492 _refine_diff_density_min -0.365 _refine_ls_extinction_coef 0.032(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 126 _refine_ls_number_reflns 3325 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.001 _refine_ls_R_factor_all 0.0725 _refine_ls_R_factor_gt 0.0475 _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/[\s^2^(Fo^2^)+(0.081P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1312 _refine_ls_wR_factor_ref 0.1411 _reflns_number_gt 2132 _reflns_number_total 3325 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file su6090.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/m' _cod_database_code 2203502 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, z' loop_ _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_type_symbol O1 0.39794(12) 0.2500 0.58496(8) 0.0299(2) Uani d S 1 O O2 0.30446(10) 0.2500 0.41487(7) 0.0219(2) Uani d S 1 O N1 0.02377(13) 0.2500 0.32687(8) 0.0197(2) Uani d S 1 N C1 0.27710(15) 0.2500 0.51396(10) 0.0208(2) Uani d S 1 C C2 0.17667(14) 0.2500 0.32710(10) 0.0187(2) Uani d S 1 C C3 -0.01715(14) 0.2500 0.42282(10) 0.0189(2) Uani d S 1 C C4 0.10352(15) 0.2500 0.51764(10) 0.0188(2) Uani d S 1 C C5 0.05645(16) 0.2500 0.61268(10) 0.0219(2) Uani d S 1 C C6 -0.11190(18) 0.2500 0.60815(11) 0.0242(3) Uani d S 1 C H6 -0.1462 0.2500 0.6710 0.029 Uiso calc SR 1 H C7 -0.23170(16) 0.2500 0.51463(12) 0.0254(3) Uani d S 1 C H7 -0.3455 0.2500 0.5144 0.030 Uiso calc SR 1 H C8 -0.18492(15) 0.2500 0.42207(11) 0.0233(3) Uani d S 1 C H8 -0.2664 0.2500 0.3582 0.028 Uiso calc SR 1 H C9 0.1785(2) 0.2500 0.71724(11) 0.0317(3) Uani d S 1 C H9A 0.1207 0.2201 0.7711 0.038 Uiso calc PR 0.50 H H9B 0.2307 0.3810 0.7303 0.038 Uiso calc PR 0.50 H H9C 0.2633 0.1490 0.7182 0.038 Uiso calc PR 0.50 H C10 0.23881(14) 0.2500 0.22986(9) 0.0179(2) Uani d S 1 C C11 0.09153(15) 0.2500 0.13392(10) 0.0248(3) Uani d S 1 C H11A 0.0224 0.1309 0.1349 0.030 Uiso calc PR 0.50 H H11B 0.0224 0.3691 0.1349 0.030 Uiso calc PR 0.50 H C12 0.15514(16) 0.2500 0.03505(10) 0.0265(3) Uani d S 1 C H12 0.0589 0.2500 -0.0269 0.032 Uiso calc SR 1 H C13 0.25990(13) 0.43563(16) 0.03269(8) 0.0273(2) Uani d . 1 C H13A 0.1923 0.5562 0.0334 0.033 Uiso calc R 1 H H13B 0.2993 0.4370 -0.0316 0.033 Uiso calc R 1 H C14 0.40801(12) 0.43543(14) 0.12743(7) 0.02358(19) Uani d . 1 C H14 0.4765 0.5567 0.1258 0.028 Uiso calc R 1 H C15 0.34586(12) 0.43626(14) 0.22713(7) 0.02296(19) Uani d . 1 C H15A 0.2797 0.5575 0.2293 0.028 Uiso calc R 1 H H15B 0.4412 0.4371 0.2884 0.028 Uiso calc R 1 H C16 0.51278(16) 0.2500 0.12420(10) 0.0235(3) Uani d S 1 C H16A 0.5524 0.2500 0.0600 0.028 Uiso calc SR 1 H H16B 0.6103 0.2500 0.1842 0.028 Uiso calc SR 1 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0196(4) 0.0484(7) 0.0209(5) 0.000 0.0036(3) 0.000 O2 0.0149(4) 0.0333(5) 0.0184(4) 0.000 0.0059(3) 0.000 N1 0.0169(4) 0.0230(5) 0.0202(5) 0.000 0.0067(4) 0.000 C1 0.0186(5) 0.0250(6) 0.0198(5) 0.000 0.0068(4) 0.000 C2 0.0173(5) 0.0201(5) 0.0193(5) 0.000 0.0058(4) 0.000 C3 0.0171(5) 0.0193(5) 0.0219(5) 0.000 0.0079(4) 0.000 C4 0.0180(5) 0.0191(5) 0.0212(5) 0.000 0.0086(4) 0.000 C5 0.0257(6) 0.0207(6) 0.0220(6) 0.000 0.0111(5) 0.000 C6 0.0284(6) 0.0217(6) 0.0286(6) 0.000 0.0184(5) 0.000 C7 0.0207(5) 0.0241(6) 0.0362(7) 0.000 0.0165(5) 0.000 C8 0.0172(5) 0.0258(6) 0.0284(6) 0.000 0.0085(5) 0.000 C9 0.0353(7) 0.0427(8) 0.0191(6) 0.000 0.0105(5) 0.000 C10 0.0167(5) 0.0210(5) 0.0174(5) 0.000 0.0069(4) 0.000 C11 0.0175(5) 0.0374(7) 0.0200(6) 0.000 0.0058(4) 0.000 C12 0.0206(5) 0.0414(8) 0.0179(5) 0.000 0.0055(4) 0.000 C13 0.0314(5) 0.0293(5) 0.0245(4) 0.0079(4) 0.0133(4) 0.0080(4) C14 0.0278(4) 0.0209(4) 0.0259(4) -0.0046(3) 0.0140(3) -0.0008(3) C15 0.0264(4) 0.0212(4) 0.0246(4) -0.0038(3) 0.0126(3) -0.0035(3) C16 0.0193(5) 0.0315(7) 0.0221(6) 0.000 0.0095(4) 0.000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O 0.0106 0.0060 '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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 O2 C1 . . 122.07(9) yes C2 N1 C3 . . 117.81(11) yes O1 C1 O2 . . 116.33(11) yes O1 C1 C4 . . 128.39(12) yes O2 C1 C4 . . 115.28(10) yes N1 C2 O2 . . 124.64(11) yes N1 C2 C10 . . 123.61(11) yes O2 C2 C10 . . 111.75(9) yes C8 C3 N1 . . 117.55(11) ? C8 C3 C4 . . 120.03(11) ? N1 C3 C4 . . 122.43(10) yes C3 C4 C5 . . 120.48(11) ? C3 C4 C1 . . 117.77(11) yes C5 C4 C1 . . 121.75(11) yes C6 C5 C4 . . 117.48(12) ? C6 C5 C9 . . 119.01(12) ? C4 C5 C9 . . 123.51(12) yes C7 C6 C5 . . 122.28(12) ? C7 C6 H6 . . 118.9 ? C5 C6 H6 . . 118.9 ? C8 C7 C6 . . 119.96(12) ? C8 C7 H7 . . 120.0 ? C6 C7 H7 . . 120.0 ? C7 C8 C3 . . 119.78(12) ? C7 C8 H8 . . 120.1 ? C3 C8 H8 . . 120.1 ? C5 C9 H9A . . 109.5 ? C5 C9 H9B . . 109.5 ? H9A C9 H9B . . 109.5 ? C5 C9 H9C . . 109.5 ? H9A C9 H9C . . 109.5 ? H9B C9 H9C . . 109.5 ? C2 C10 C11 . . 109.81(9) ? C2 C10 C15 . . 110.08(6) ? C11 C10 C15 . . 109.19(7) ? C2 C10 C15 . 4_565 110.08(6) ? C11 C10 C15 . 4_565 109.19(7) ? C15 C10 C15 . 4_565 108.44(10) ? C12 C11 C10 . . 109.70(10) ? C12 C11 H11A . . 109.7 ? C10 C11 H11A . . 109.7 ? C12 C11 H11B . . 109.7 ? C10 C11 H11B . . 109.7 ? H11A C11 H11B . . 108.2 ? C13 C12 C13 . 4_565 109.51(11) ? C13 C12 C11 . . 109.74(7) ? C13 C12 C11 4_565 . 109.74(7) ? C13 C12 H12 . . 109.3 ? C13 C12 H12 4_565 . 109.3 ? C11 C12 H12 . . 109.3 ? C12 C13 C14 . . 109.36(8) ? C12 C13 H13A . . 109.8 ? C14 C13 H13A . . 109.8 ? C12 C13 H13B . . 109.8 ? C14 C13 H13B . . 109.8 ? H13A C13 H13B . . 108.2 ? C16 C14 C13 . . 109.15(9) ? C16 C14 C15 . . 110.09(8) ? C13 C14 C15 . . 109.54(8) ? C16 C14 H14 . . 109.3 ? C13 C14 H14 . . 109.3 ? C15 C14 H14 . . 109.3 ? C14 C15 C10 . . 109.70(8) ? C14 C15 H15A . . 109.7 ? C10 C15 H15A . . 109.7 ? C14 C15 H15B . . 109.7 ? C10 C15 H15B . . 109.7 ? H15A C15 H15B . . 108.2 ? C14 C16 C14 4_565 . 109.24(10) ? C14 C16 H16A 4_565 . 109.8 ? C14 C16 H16A . . 109.8 ? C14 C16 H16B 4_565 . 109.8 ? C14 C16 H16B . . 109.8 ? H16A C16 H16B . . 108.3 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.2010(16) yes O2 C2 . 1.3750(15) yes O2 C1 . 1.3940(15) yes N1 C2 . 1.2762(15) yes N1 C3 . 1.4019(16) yes C1 C4 . 1.4625(17) yes C2 C10 . 1.5094(16) ? C3 C8 . 1.3988(17) ? C3 C4 . 1.4082(18) yes C4 C5 . 1.4151(17) ? C5 C6 . 1.3923(19) ? C5 C9 . 1.510(2) ? C6 C7 . 1.392(2) ? C6 H6 . 0.9500 ? C7 C8 . 1.3821(19) ? C7 H7 . 0.9500 ? C8 H8 . 0.9500 ? C9 H9A . 0.9800 ? C9 H9B . 0.9800 ? C9 H9C . 0.9800 ? C10 C11 . 1.5398(17) ? C10 C15 . 1.5457(11) ? C10 C15 4_565 1.5457(11) ? C11 C12 . 1.5368(18) ? C11 H11A . 0.9900 ? C11 H11B . 0.9900 ? C12 C13 . 1.5303(13) ? C12 C13 4_565 1.5303(13) ? C12 H12 . 1.0000 ? C13 C14 . 1.5339(14) ? C13 H13A . 0.9900 ? C13 H13B . 0.9900 ? C14 C16 . 1.5311(12) ? C14 C15 . 1.5405(12) ? C14 H14 . 1.0000 ? C15 H15A . 0.9900 ? C15 H15B . 0.9900 ? C16 C14 4_565 1.5311(12) ? C16 H16A . 0.9900 ? C16 H16B . 0.9900 ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag C1 C7 3.3984(4) 3_556 yes C3 C5 3.4038(4) 3_556 yes C4 C8 3.4884(5) 3_556 yes N1 C6 3.5083(5) 3_556 yes 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_site_symmetry_1 _geom_torsion_site_symmetry_4 _geom_torsion C2 O2 C1 O1 . . 180.0 C2 O2 C1 C4 . . 0.0 C3 N1 C2 O2 . . 0.0 C3 N1 C2 C10 . . 180.0 C1 O2 C2 N1 . . 0.0 C1 O2 C2 C10 . . 180.0 C2 N1 C3 C8 . . 180.0 C2 N1 C3 C4 . . 0.0 C8 C3 C4 C5 . . 0.0 N1 C3 C4 C5 . . 180.0 C8 C3 C4 C1 . . 180.0 N1 C3 C4 C1 . . 0.0 O1 C1 C4 C3 . . 180.0 O2 C1 C4 C3 . . 0.0 O1 C1 C4 C5 . . 0.0 O2 C1 C4 C5 . . 180.0 C3 C4 C5 C6 . . 0.0 C1 C4 C5 C6 . . 180.0 C3 C4 C5 C9 . . 180.0 C1 C4 C5 C9 . . 0.0 C4 C5 C6 C7 . . 0.0 C9 C5 C6 C7 . . 180.0 C5 C6 C7 C8 . . 0.0 C6 C7 C8 C3 . . 0.0 N1 C3 C8 C7 . . 180.0 C4 C3 C8 C7 . . 0.0 N1 C2 C10 C11 . . 0.0 O2 C2 C10 C11 . . 180.0 N1 C2 C10 C15 . . 120.25(7) O2 C2 C10 C15 . . -59.75(7) N1 C2 C10 C15 . 4_565 -120.25(7) O2 C2 C10 C15 . 4_565 59.75(7) C2 C10 C11 C12 . . 180.0 C15 C10 C11 C12 . . 59.21(6) C15 C10 C11 C12 4_565 . -59.21(6) C10 C11 C12 C13 . . -60.19(7) C10 C11 C12 C13 . 4_565 60.19(7) C13 C12 C13 C14 4_565 . -60.07(12) C11 C12 C13 C14 . . 60.45(11) C12 C13 C14 C16 . . 60.38(10) C12 C13 C14 C15 . . -60.23(10) C16 C14 C15 C10 . . -60.25(10) C13 C14 C15 C10 . . 59.79(10) C2 C10 C15 C14 . . -179.74(8) C11 C10 C15 C14 . . -59.12(10) C15 C10 C15 C14 4_565 . 59.77(12) C13 C14 C16 C14 . 4_565 -60.82(12) C15 C14 C16 C14 . 4_565 59.45(13)