#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/78/2227884.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_2227884
loop_
_publ_author_name
'Maharramov, Abel M.'
'Ismiyev, Arif I.'
'Rashidov, Bahruz A.'
_publ_section_title
;
 rac-1-(6-Hydroxy-3,6-dimethyl-4-phenyl-4,5,6,7-tetrahydro-2,1-benzoxazol-5-yl)ethanone
;
_journal_coeditor_code           PB2043
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3030
_journal_paper_doi               10.1107/S1600536810043667
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C17 H19 N O3'
_chemical_formula_moiety         'C17 H19 N O3'
_chemical_formula_sum            'C17 H19 N O3'
_chemical_formula_weight         285.33
_chemical_name_systematic
;
rac-1-(6-Hydroxy-3,6-dimethyl-4-phenyl-4,5,6,7-tetrahydro-
2,1-benzoxazol-5-yl)ethanone
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.4960(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.1518(9)
_cell_length_b                   5.5353(3)
_cell_length_c                   17.2956(9)
_cell_measurement_reflns_used    5396
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.23
_cell_measurement_theta_min      2.42
_cell_volume                     1503.61(14)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2001)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16629
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.42
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_correction_T_min  0.9746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.209
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3724
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0456
_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)+(0.0748P)²+0.3882P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.1414
_reflns_number_gt                2840
_reflns_number_total             3724
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pb2043.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2227884
_cod_database_fobs_code          2227884
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_disorder_assembly
_atom_site_disorder_group
N N1 0.01908(8) 1.0929(3) 0.62899(8) 0.0564(4) Uani d . 1 . .
O O1 0.03792(7) 0.9296(3) 0.69321(7) 0.0604(3) Uani d . 1 . .
C C1 0.11922(9) 0.8524(3) 0.70211(9) 0.0487(4) Uani d . 1 . .
C C1A 0.15432(8) 0.9589(3) 0.64670(8) 0.0396(3) Uani d . 1 . .
C C2 0.24052(8) 0.9339(2) 0.62856(7) 0.0345(3) Uani d . 1 . .
H H2A 0.2427 0.7768 0.6030 0.041 Uiso calc R 1 . .
C C3 0.25009(8) 1.1335(2) 0.56826(8) 0.0359(3) Uani d . 1 . .
H H3A 0.2545 1.2872 0.5970 0.043 Uiso calc R 1 . .
C C4 0.16899(9) 1.1510(2) 0.49910(8) 0.0385(3) Uani d . 1 . .
O O3 0.14932(6) 0.90993(17) 0.47197(6) 0.0418(2) Uani d . 1 . .
H H3B 0.1068 0.9106 0.4352 0.063 Uiso calc R 1 . .
C C5 0.09667(9) 1.2536(3) 0.53313(9) 0.0467(3) Uani d . 1 . .
H H5A 0.1089 1.4201 0.5492 0.056 Uiso calc R 1 . .
H H5B 0.0436 1.2497 0.4928 0.056 Uiso calc R 1 . .
C C5A 0.08853(9) 1.1061(3) 0.60280(8) 0.0431(3) Uani d . 1 . .
C C6 0.14961(12) 0.6749(4) 0.76606(11) 0.0655(5) Uani d . 1 . .
H H6A 0.1053 0.6434 0.7933 0.098 Uiso calc R 1 . .
H H6B 0.1986 0.7384 0.8030 0.098 Uiso calc R 1 . .
H H6C 0.1647 0.5275 0.7435 0.098 Uiso calc R 1 . .
C C7 0.31251(8) 0.9425(2) 0.70323(8) 0.0365(3) Uani d . 1 . .
C C8 0.31689(10) 1.1287(3) 0.75728(9) 0.0529(4) Uani d . 1 . .
H H8A 0.2767 1.2521 0.7468 0.063 Uiso calc R 1 . .
C C9 0.38009(11) 1.1345(4) 0.82687(10) 0.0621(5) Uani d . 1 . .
H H9A 0.3818 1.2600 0.8630 0.075 Uiso calc R 1 . .
C C10 0.44022(10) 0.9549(4) 0.84244(10) 0.0601(5) Uani d . 1 . .
H H10A 0.4823 0.9574 0.8894 0.072 Uiso calc R 1 . .
C C11 0.43813(10) 0.7719(4) 0.78874(11) 0.0610(5) Uani d . 1 . .
H H11A 0.4796 0.6520 0.7987 0.073 Uiso calc R 1 . .
C C12 0.37398(9) 0.7651(3) 0.71932(9) 0.0473(3) Uani d . 1 . .
H H12A 0.3726 0.6394 0.6834 0.057 Uiso calc R 1 . .
C C13 0.33153(9) 1.1072(3) 0.53928(8) 0.0445(3) Uani d . 1 . .
O O2 0.37936(8) 1.2779(3) 0.54585(9) 0.0725(4) Uani d . 1 . .
C C14 0.35025(12) 0.8785(4) 0.50168(12) 0.0625(5) Uani d . 1 . .
H H14A 0.4038 0.8928 0.4870 0.094 Uiso calc R 1 . .
H H14B 0.3060 0.8472 0.4551 0.094 Uiso calc R 1 . .
H H14C 0.3530 0.7477 0.5387 0.094 Uiso calc R 1 . .
C C15 0.18200(11) 1.3114(3) 0.43155(9) 0.0532(4) Uani d . 1 . .
H H15A 0.1305 1.3163 0.3905 0.080 Uiso calc R 1 . .
H H15B 0.2273 1.2474 0.4103 0.080 Uiso calc R 1 . .
H H15C 0.1964 1.4718 0.4512 0.080 Uiso calc R 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5A N1 O1 . . 105.32(12) ?
C1 O1 N1 . . 108.49(12) ?
O1 C1 C1A . . 109.66(14) ?
O1 C1 C6 . . 116.05(14) ?
C1A C1 C6 . . 134.27(14) ?
C1 C1A C5A . . 104.14(13) ?
C1 C1A C2 . . 131.88(13) ?
C5A C1A C2 . . 123.94(13) ?
C1A C2 C7 . . 112.40(11) ?
C1A C2 C3 . . 108.51(10) ?
C7 C2 C3 . . 111.81(10) ?
C1A C2 H2A . . 108.0 ?
C7 C2 H2A . . 108.0 ?
C3 C2 H2A . . 108.0 ?
C13 C3 C2 . . 112.53(11) ?
C13 C3 C4 . . 112.97(11) ?
C2 C3 C4 . . 111.28(10) ?
C13 C3 H3A . . 106.5 ?
C2 C3 H3A . . 106.5 ?
C4 C3 H3A . . 106.5 ?
O3 C4 C15 . . 110.73(12) ?
O3 C4 C5 . . 109.96(12) ?
C15 C4 C5 . . 109.44(12) ?
O3 C4 C3 . . 106.10(10) ?
C15 C4 C3 . . 112.61(12) ?
C5 C4 C3 . . 107.92(11) ?
C4 O3 H3B . . 109.5 ?
C5A C5 C4 . . 109.10(11) ?
C5A C5 H5A . . 109.9 ?
C4 C5 H5A . . 109.9 ?
C5A C5 H5B . . 109.9 ?
C4 C5 H5B . . 109.9 ?
H5A C5 H5B . . 108.3 ?
N1 C5A C1A . . 112.39(14) ?
N1 C5A C5 . . 123.88(13) ?
C1A C5A C5 . . 123.71(13) ?
C1 C6 H6A . . 109.5 ?
C1 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C1 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C8 C7 C12 . . 118.30(13) ?
C8 C7 C2 . . 120.33(12) ?
C12 C7 C2 . . 121.36(12) ?
C7 C8 C9 . . 121.07(15) ?
C7 C8 H8A . . 119.5 ?
C9 C8 H8A . . 119.5 ?
C8 C9 C10 . . 119.88(17) ?
C8 C9 H9A . . 120.1 ?
C10 C9 H9A . . 120.1 ?
C11 C10 C9 . . 119.92(14) ?
C11 C10 H10A . . 120.0 ?
C9 C10 H10A . . 120.0 ?
C10 C11 C12 . . 120.04(15) ?
C10 C11 H11A . . 120.0 ?
C12 C11 H11A . . 120.0 ?
C7 C12 C11 . . 120.76(15) ?
C7 C12 H12A . . 119.6 ?
C11 C12 H12A . . 119.6 ?
O2 C13 C14 . . 121.07(15) ?
O2 C13 C3 . . 118.51(15) ?
C14 C13 C3 . . 120.40(13) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C4 C15 H15A . . 109.5 ?
C4 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C4 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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
N1 C5A . 1.306(2) ?
N1 O1 . 1.4090(19) ?
O1 C1 . 1.3550(18) ?
C1 C1A . 1.357(2) ?
C1 C6 . 1.475(2) ?
C1A C5A . 1.4117(19) ?
C1A C2 . 1.5032(18) ?
C2 C7 . 1.5236(17) ?
C2 C3 . 1.5514(18) ?
C2 H2A . 0.9800 ?
C3 C13 . 1.520(2) ?
C3 C4 . 1.5572(17) ?
C3 H3A . 0.9800 ?
C4 O3 . 1.4257(16) ?
C4 C15 . 1.520(2) ?
C4 C5 . 1.534(2) ?
O3 H3B . 0.8200 ?
C5 C5A . 1.487(2) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 H6A . 0.9600 ?
C6 H6B . 0.9600 ?
C6 H6C . 0.9600 ?
C7 C8 . 1.382(2) ?
C7 C12 . 1.3779(19) ?
C8 C9 . 1.385(2) ?
C8 H8A . 0.9300 ?
C9 C10 . 1.372(3) ?
C9 H9A . 0.9300 ?
C10 C11 . 1.370(3) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.391(2) ?
C11 H11A . 0.9300 ?
C12 H12A . 0.9300 ?
C13 O2 . 1.2089(19) ?
C13 C14 . 1.486(2) ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
C15 H15A . 0.9600 ?
C15 H15B . 0.9600 ?
C15 H15C . 0.9600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O3 H3B N1 3_576 0.82000 2.077 2.8689(17) 162.34 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5A N1 O1 C1 . . . . -0.02(17) ?
N1 O1 C1 C1A . . . . 0.22(18) ?
N1 O1 C1 C6 . . . . -178.75(15) ?
O1 C1 C1A C5A . . . . -0.32(17) ?
C6 C1 C1A C5A . . . . 178.4(2) ?
O1 C1 C1A C2 . . . . -178.25(14) ?
C6 C1 C1A C2 . . . . 0.5(3) ?
C1 C1A C2 C7 . . . . -46.1(2) ?
C5A C1A C2 C7 . . . . 136.34(14) ?
C1 C1A C2 C3 . . . . -170.25(15) ?
C5A C1A C2 C3 . . . . 12.17(18) ?
C1A C2 C3 C13 . . . . -173.88(11) ?
C7 C2 C3 C13 . . . . 61.59(14) ?
C1A C2 C3 C4 . . . . -45.93(14) ?
C7 C2 C3 C4 . . . . -170.45(10) ?
C13 C3 C4 O3 . . . . 79.39(14) ?
C2 C3 C4 O3 . . . . -48.32(14) ?
C13 C3 C4 C15 . . . . -41.88(16) ?
C2 C3 C4 C15 . . . . -169.60(12) ?
C13 C3 C4 C5 . . . . -162.78(12) ?
C2 C3 C4 C5 . . . . 69.50(14) ?
O3 C4 C5 C5A . . . . 62.22(14) ?
C15 C4 C5 C5A . . . . -175.95(12) ?
C3 C4 C5 C5A . . . . -53.09(15) ?
O1 N1 C5A C1A . . . . -0.19(17) ?
O1 N1 C5A C5 . . . . 178.08(13) ?
C1 C1A C5A N1 . . . . 0.32(17) ?
C2 C1A C5A N1 . . . . 178.46(13) ?
C1 C1A C5A C5 . . . . -177.95(14) ?
C2 C1A C5A C5 . . . . 0.2(2) ?
C4 C5 C5A N1 . . . . -157.04(14) ?
C4 C5 C5A C1A . . . . 21.04(19) ?
C1A C2 C7 C8 . . . . -51.35(18) ?
C3 C2 C7 C8 . . . . 70.98(16) ?
C1A C2 C7 C12 . . . . 127.79(14) ?
C3 C2 C7 C12 . . . . -109.88(15) ?
C12 C7 C8 C9 . . . . -1.6(2) ?
C2 C7 C8 C9 . . . . 177.60(16) ?
C7 C8 C9 C10 . . . . 0.8(3) ?
C8 C9 C10 C11 . . . . 0.7(3) ?
C9 C10 C11 C12 . . . . -1.5(3) ?
C8 C7 C12 C11 . . . . 0.8(2) ?
C2 C7 C12 C11 . . . . -178.33(14) ?
C10 C11 C12 C7 . . . . 0.7(3) ?
C2 C3 C13 O2 . . . . -125.57(14) ?
C4 C3 C13 O2 . . . . 107.38(16) ?
C2 C3 C13 C14 . . . . 56.16(17) ?
C4 C3 C13 C14 . . . . -70.90(17) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 2957905
