#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/35/2203502.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
'Jonathan D Crane'
'Eleanor Rogerson'
_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_paper_doi               10.1107/S1600536804006907
_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       'φ and ω'
_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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.081P)²] where P = (Fo²+2Fc²)/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>2σ(I)
_cod_data_source_file            su6090.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2203502
_cod_database_fobs_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_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)
