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#$Date: 2023-03-08 12:00:21 +0200 (Wed, 08 Mar 2023) $
#$Revision: 281740 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106883.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_8106883
loop_
_publ_author_name
'Fu, Ying'
'Wang, Yun-Kai'
'Yang, Fei'
'Ye, Fei'
_publ_section_title
;
 Crystal structure of
 1-((2R,3S)-2,3-dimethyl-2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)-2-phenoxyethan-1-one,
 C18H19NO3
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              389
_journal_page_last               391
_journal_paper_doi               10.1515/ncrs-2014-9124
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety
;
 'C11 H9 Cl4 N O2'  
;
_chemical_formula_sum            'C18 H19 N O3'
_chemical_formula_weight         297.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                97.00(3)
_cell_angle_beta                 105.63(3)
_cell_angle_gamma                99.16(3)
_cell_formula_units_Z            2
_cell_length_a                   7.9928(16)
_cell_length_b                   8.7582(18)
_cell_length_c                   11.692(2)
_cell_measurement_reflns_used    6265
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.56
_cell_measurement_theta_min      3.23
_cell_volume                     766.4(3)
_computing_cell_refinement       'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_collection       'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0351
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7586
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.23
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_correction_T_min  0.9735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
ABSCOR (Higashi, 1995)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0447
_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)+(0.0831P)²+0.0000P] where P=(Fo²+2Fc²)/3'
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1235
_refine_ls_wR_factor_ref         0.1313
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2561
_reflns_number_total             3480
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2014-9124_suppl.cif
_cod_data_source_block           1
_cod_database_code               8106883
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
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
C1 C 0.73402(17) 0.88768(14) 0.81626(11) 0.0419(3) Uani 1 1 d . . .
C2 C 0.8639(2) 0.80820(18) 0.86811(13) 0.0559(4) Uani 1 1 d . . .
H2 H 0.9478 0.8537 0.9414 0.067 Uiso 1 1 calc R . .
C3 C 0.8694(2) 0.66281(18) 0.81202(15) 0.0617(4) Uani 1 1 d . . .
H3 H 0.9564 0.6098 0.8473 0.074 Uiso 1 1 calc R . .
C4 C 0.7453(2) 0.59560(17) 0.70313(14) 0.0578(4) Uani 1 1 d . . .
H4 H 0.7494 0.4974 0.6647 0.069 Uiso 1 1 calc R . .
C5 C 0.61520(19) 0.67352(15) 0.65110(13) 0.0481(3) Uani 1 1 d . . .
H5 H 0.5319 0.6268 0.5778 0.058 Uiso 1 1 calc R . .
C6 C 0.60637(16) 0.82082(14) 0.70634(10) 0.0368(3) Uani 1 1 d . . .
C7 C 0.44857(17) 1.03010(14) 0.74805(10) 0.0400(3) Uani 1 1 d . . .
H7 H 0.3781 1.0975 0.7035 0.048 Uiso 1 1 calc R . .
C8 C 0.63274(17) 1.12660(14) 0.81166(11) 0.0417(3) Uani 1 1 d . . .
H8 H 0.6872 1.1589 0.7504 0.050 Uiso 1 1 calc R . .
C9 C 0.3494(2) 0.96146(18) 0.83003(14) 0.0588(4) Uani 1 1 d . . .
H9A H 0.2332 0.9055 0.7826 0.088 Uiso 1 1 calc R . .
H9B H 0.3391 1.0447 0.8876 0.088 Uiso 1 1 calc R . .
H9C H 0.4133 0.8907 0.8717 0.088 Uiso 1 1 calc R . .
C10 C 0.6412(2) 1.27184(17) 0.89931(13) 0.0577(4) Uani 1 1 d . . .
H10A H 0.5863 1.2425 0.9592 0.087 Uiso 1 1 calc R . .
H10B H 0.5798 1.3431 0.8565 0.087 Uiso 1 1 calc R . .
H10C H 0.7629 1.3221 0.9378 0.087 Uiso 1 1 calc R . .
C11 C 0.36946(15) 0.87498(14) 0.54149(10) 0.0373(3) Uani 1 1 d . . .
C12 C 0.22318(16) 0.96946(15) 0.50855(11) 0.0428(3) Uani 1 1 d . . .
H12A H 0.1442 0.9519 0.5578 0.051 Uiso 1 1 calc R . .
H12B H 0.2758 1.0805 0.5253 0.051 Uiso 1 1 calc R . .
C13 C 0.00420(15) 0.78631(15) 0.34689(11) 0.0411(3) Uani 1 1 d . . .
C14 C -0.07090(18) 0.74728(17) 0.22288(12) 0.0504(3) Uani 1 1 d . . .
H14 H -0.0341 0.8114 0.1728 0.060 Uiso 1 1 calc R . .
C15 C -0.1999(2) 0.6136(2) 0.17401(15) 0.0644(4) Uani 1 1 d . . .
H15 H -0.2493 0.5874 0.0908 0.077 Uiso 1 1 calc R . .
C16 C -0.2561(2) 0.5189(2) 0.24712(18) 0.0716(5) Uani 1 1 d . . .
H16 H -0.3442 0.4293 0.2140 0.086 Uiso 1 1 calc R . .
C17 C -0.1809(2) 0.55789(19) 0.36944(17) 0.0686(5) Uani 1 1 d . . .
H17 H -0.2188 0.4935 0.4190 0.082 Uiso 1 1 calc R . .
C18 C -0.04983(19) 0.69087(17) 0.42111(14) 0.0539(4) Uani 1 1 d . . .
H18 H 0.0008 0.7153 0.5043 0.065 Uiso 1 1 calc R . .
N1 N 0.46833(13) 0.90315(11) 0.65934(8) 0.0374(2) Uani 1 1 d . . .
O1 O 0.73933(13) 1.03161(11) 0.87973(8) 0.0499(3) Uani 1 1 d . . .
O2 O 0.39227(12) 0.78204(11) 0.46342(7) 0.0488(3) Uani 1 1 d . . .
O3 O 0.12514(11) 0.92528(11) 0.38537(7) 0.0455(2) Uani 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
O1 C1 C2 115.95(12) . .
O1 C1 C6 123.48(11) . .
C2 C1 C6 120.57(12) . .
C3 C2 C1 120.45(13) . .
C3 C2 H2 119.8 . .
C1 C2 H2 119.8 . .
C2 C3 C4 119.76(13) . .
C2 C3 H3 120.1 . .
C4 C3 H3 120.1 . .
C3 C4 C5 120.20(13) . .
C3 C4 H4 119.9 . .
C5 C4 H4 119.9 . .
C4 C5 C6 121.16(13) . .
C4 C5 H5 119.4 . .
C6 C5 H5 119.4 . .
C5 C6 C1 117.86(12) . .
C5 C6 N1 123.36(11) . .
C1 C6 N1 118.71(10) . .
N1 C7 C8 106.87(10) . .
N1 C7 C9 110.38(11) . .
C8 C7 C9 115.21(11) . .
N1 C7 H7 108.1 . .
C8 C7 H7 108.1 . .
C9 C7 H7 108.1 . .
O1 C8 C10 106.47(10) . .
O1 C8 C7 109.56(10) . .
C10 C8 C7 115.56(11) . .
O1 C8 H8 108.3 . .
C10 C8 H8 108.3 . .
C7 C8 H8 108.3 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
O2 C11 N1 124.05(11) . .
O2 C11 C12 119.75(11) . .
N1 C11 C12 116.20(10) . .
O3 C12 C11 110.96(10) . .
O3 C12 H12A 109.4 . .
C11 C12 H12A 109.4 . .
O3 C12 H12B 109.4 . .
C11 C12 H12B 109.4 . .
H12A C12 H12B 108.0 . .
O3 C13 C18 125.20(12) . .
O3 C13 C14 114.75(12) . .
C18 C13 C14 120.00(13) . .
C15 C14 C13 119.97(15) . .
C15 C14 H14 120.0 . .
C13 C14 H14 120.0 . .
C16 C15 C14 120.49(15) . .
C16 C15 H15 119.8 . .
C14 C15 H15 119.8 . .
C17 C16 C15 119.22(16) . .
C17 C16 H16 120.4 . .
C15 C16 H16 120.4 . .
C16 C17 C18 121.57(17) . .
C16 C17 H17 119.2 . .
C18 C17 H17 119.2 . .
C13 C18 C17 118.75(14) . .
C13 C18 H18 120.6 . .
C17 C18 H18 120.6 . .
C11 N1 C6 123.42(9) . .
C11 N1 C7 121.84(10) . .
C6 N1 C7 114.63(9) . .
C1 O1 C8 114.35(9) . .
C13 O3 C12 119.73(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.3710(15) .
C1 C2 1.3866(18) .
C1 C6 1.3984(19) .
C2 C3 1.372(2) .
C2 H2 0.9300 .
C3 C4 1.379(2) .
C3 H3 0.9300 .
C4 C5 1.380(2) .
C4 H4 0.9300 .
C5 C6 1.3917(17) .
C5 H5 0.9300 .
C6 N1 1.4361(15) .
C7 N1 1.4833(14) .
C7 C8 1.5150(19) .
C7 C9 1.5186(19) .
C7 H7 0.9800 .
C8 O1 1.4397(15) .
C8 C10 1.5134(17) .
C8 H8 0.9800 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 O2 1.2185(14) .
C11 N1 1.3610(16) .
C11 C12 1.5307(17) .
C12 O3 1.4134(15) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 O3 1.3697(16) .
C13 C18 1.379(2) .
C13 C14 1.3872(18) .
C14 C15 1.377(2) .
C14 H14 0.9300 .
C15 C16 1.372(3) .
C15 H15 0.9300 .
C16 C17 1.370(3) .
C16 H16 0.9300 .
C17 C18 1.385(2) .
C17 H17 0.9300 .
C18 H18 0.9300 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8 H8 O2 0.98 2.55 3.371(3) 141.6 2_676
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
O1 C1 C2 C3 179.62(14) . . . .
C6 C1 C2 C3 0.2(2) . . . .
C1 C2 C3 C4 0.3(3) . . . .
C2 C3 C4 C5 -0.5(3) . . . .
C3 C4 C5 C6 0.3(2) . . . .
C4 C5 C6 C1 0.2(2) . . . .
C4 C5 C6 N1 -176.57(13) . . . .
O1 C1 C6 C5 -179.78(12) . . . .
C2 C1 C6 C5 -0.4(2) . . . .
O1 C1 C6 N1 -2.9(2) . . . .
C2 C1 C6 N1 176.46(12) . . . .
N1 C7 C8 O1 -64.79(12) . . . .
C9 C7 C8 O1 58.23(13) . . . .
N1 C7 C8 C10 174.98(11) . . . .
C9 C7 C8 C10 -62.00(15) . . . .
O2 C11 C12 O3 3.12(17) . . . .
N1 C11 C12 O3 -177.48(10) . . . .
O3 C13 C14 C15 -177.18(11) . . . .
C18 C13 C14 C15 0.29(19) . . . .
C13 C14 C15 C16 0.5(2) . . . .
C14 C15 C16 C17 -0.7(2) . . . .
C15 C16 C17 C18 0.2(2) . . . .
O3 C13 C18 C17 176.36(12) . . . .
C14 C13 C18 C17 -0.8(2) . . . .
C16 C17 C18 C13 0.6(2) . . . .
O2 C11 N1 C6 -3.0(2) . . . .
C12 C11 N1 C6 177.67(11) . . . .
O2 C11 N1 C7 172.98(12) . . . .
C12 C11 N1 C7 -6.39(17) . . . .
C5 C6 N1 C11 -22.57(19) . . . .
C1 C6 N1 C11 160.71(12) . . . .
C5 C6 N1 C7 161.23(12) . . . .
C1 C6 N1 C7 -15.49(16) . . . .
C8 C7 N1 C11 -128.69(12) . . . .
C9 C7 N1 C11 105.33(14) . . . .
C8 C7 N1 C6 47.58(13) . . . .
C9 C7 N1 C6 -78.40(14) . . . .
C2 C1 O1 C8 165.67(12) . . . .
C6 C1 O1 C8 -14.96(19) . . . .
C10 C8 O1 C1 174.53(11) . . . .
C7 C8 O1 C1 48.91(14) . . . .
C18 C13 O3 C12 8.98(17) . . . .
C14 C13 O3 C12 -173.70(10) . . . .
C11 C12 O3 C13 75.40(13) . . . .
