#------------------------------------------------------------------------------
#$Date: 2020-11-06 15:07:16 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258947 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/76/7157687.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_7157687
loop_
_publ_author_name
'Borgohain, Hemi'
'Talukdar, Kangkan'
'Sarma, Bipul'
'Das, Sajal Kumar'
_publ_section_title
;
 Regioselectivity of the trifluoroethanol-promoted intramolecular
 N-Boc-epoxide cyclization towards 1,3-oxazolidin-2-ones and
 1,3-oxazinan-2-ones.
;
_journal_issue                   37
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7401
_journal_page_last               7413
_journal_paper_doi               10.1039/d0ob01698e
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-12-08 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.3884(13)
_cell_length_b                   26.944(3)
_cell_length_c                   6.9828(6)
_cell_measurement_reflns_used    1420
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.35
_cell_measurement_theta_min      2.67
_cell_volume                     2707.1(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1000
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            21415
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.372
_diffrn_reflns_theta_min         1.512
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.767
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3356
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.767
_refine_ls_R_factor_all          0.1318
_refine_ls_R_factor_gt           0.0620
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1619P)²+1.7095P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.2411
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1667
_reflns_number_total             3356
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01698e2.cif
_cod_data_source_block           hsd
_cod_depositor_comments
'Adding full bibliography for 7157687--7157688.cif.'
_cod_original_cell_volume        2707.1(4)
_cod_database_code               7157687
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.969
_shelx_estimated_absorpt_t_max   0.980
_exptl_absorpt_special_details   SADABS
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.61775(13) 0.46127(6) 0.0818(3) 0.0368(5) Uani 1 1 d . . . . .
O2 O 0.63323(14) 0.52446(7) -0.1158(3) 0.0418(5) Uani 1 1 d . . . . .
O3 O 0.61756(18) 0.45127(8) 0.6009(3) 0.0550(6) Uani 1 1 d . . . . .
H3 H 0.6248 0.4730 0.6818 0.082 Uiso 1 1 calc R U . . .
N3 N 0.63492(14) 0.54087(7) 0.2032(3) 0.0340(5) Uani 1 1 d . . . . .
C2 C 0.62779(17) 0.51065(9) 0.0514(4) 0.0317(6) Uani 1 1 d . . . . .
C4 C 0.6300(2) 0.52451(9) 0.4031(4) 0.0376(6) Uani 1 1 d . . . . .
H4A H 0.5694 0.5327 0.4550 0.045 Uiso 1 1 calc R U . . .
H4B H 0.6765 0.5420 0.4776 0.045 Uiso 1 1 calc R U . . .
C5 C 0.64592(19) 0.46927(9) 0.4207(4) 0.0365(6) Uani 1 1 d . . . . .
H5 H 0.7120 0.4620 0.4017 0.044 Uiso 1 1 calc R U . . .
C6 C 0.58975(18) 0.44295(9) 0.2699(4) 0.0333(6) Uani 1 1 d . . . . .
H6 H 0.5239 0.4506 0.2896 0.040 Uiso 1 1 calc R U . . .
C7 C 0.60211(18) 0.38725(9) 0.2708(4) 0.0361(6) Uani 1 1 d . . . . .
C8 C 0.6742(2) 0.36445(10) 0.1715(5) 0.0494(8) Uani 1 1 d . . . . .
H8 H 0.7155 0.3834 0.1000 0.059 Uiso 1 1 calc R U . . .
C9 C 0.6843(3) 0.31332(11) 0.1795(5) 0.0610(9) Uani 1 1 d . . . . .
H9 H 0.7315 0.2981 0.1103 0.073 Uiso 1 1 calc R U . . .
C10 C 0.6255(3) 0.28504(11) 0.2881(5) 0.0599(10) Uani 1 1 d . . . . .
H10 H 0.6334 0.2508 0.2944 0.072 Uiso 1 1 calc R U . . .
C11 C 0.5547(3) 0.30740(12) 0.3877(5) 0.0629(10) Uani 1 1 d . . . . .
H11 H 0.5147 0.2883 0.4619 0.075 Uiso 1 1 calc R U . . .
C12 C 0.5426(2) 0.35845(10) 0.3780(5) 0.0515(8) Uani 1 1 d . . . . .
H12 H 0.4939 0.3733 0.4443 0.062 Uiso 1 1 calc R U . . .
C13 C 0.63695(19) 0.59405(9) 0.1744(4) 0.0360(6) Uani 1 1 d . . . . .
C14 C 0.7169(2) 0.61982(10) 0.2151(5) 0.0503(8) Uani 1 1 d . . . . .
H14 H 0.7701 0.6030 0.2543 0.060 Uiso 1 1 calc R U . . .
C15 C 0.7179(3) 0.67117(11) 0.1972(6) 0.0712(11) Uani 1 1 d . . . . .
H15 H 0.7716 0.6889 0.2253 0.085 Uiso 1 1 calc R U . . .
C16 C 0.6387(3) 0.69572(12) 0.1375(6) 0.0742(12) Uani 1 1 d . . . . .
H16 H 0.6392 0.7301 0.1252 0.089 Uiso 1 1 calc R U . . .
C17 C 0.5598(3) 0.66972(12) 0.0967(6) 0.0692(11) Uani 1 1 d . . . . .
H17 H 0.5070 0.6864 0.0553 0.083 Uiso 1 1 calc R U . . .
C18 C 0.5579(2) 0.61843(11) 0.1165(5) 0.0524(8) Uani 1 1 d . . . . .
H18 H 0.5038 0.6008 0.0908 0.063 Uiso 1 1 calc R U . . .
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
C2 O1 C6 120.17(18) . . ?
C5 O3 H3 109.5 . . ?
C2 N3 C13 119.5(2) . . ?
C2 N3 C4 124.5(2) . . ?
C13 N3 C4 115.6(2) . . ?
O2 C2 N3 124.3(2) . . ?
O2 C2 O1 117.0(2) . . ?
N3 C2 O1 118.7(2) . . ?
N3 C4 C5 111.5(2) . . ?
N3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
O3 C5 C6 107.9(2) . . ?
O3 C5 C4 111.6(2) . . ?
C6 C5 C4 109.0(2) . . ?
O3 C5 H5 109.4 . . ?
C6 C5 H5 109.4 . . ?
C4 C5 H5 109.4 . . ?
O1 C6 C5 108.8(2) . . ?
O1 C6 C7 107.89(19) . . ?
C5 C6 C7 113.7(2) . . ?
O1 C6 H6 108.8 . . ?
C5 C6 H6 108.8 . . ?
C7 C6 H6 108.8 . . ?
C12 C7 C8 119.1(3) . . ?
C12 C7 C6 119.2(2) . . ?
C8 C7 C6 121.6(2) . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.7(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 120.4(3) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C18 120.8(3) . . ?
C14 C13 N3 119.2(2) . . ?
C18 C13 N3 119.8(2) . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C16 C15 C14 119.7(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.4(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 119.3(3) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
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 C2 1.355(3) . ?
O1 C6 1.459(3) . ?
O2 C2 1.228(3) . ?
O3 C5 1.409(3) . ?
O3 H3 0.8200 . ?
N3 C2 1.341(3) . ?
N3 C13 1.447(3) . ?
N3 C4 1.465(3) . ?
C4 C5 1.511(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.505(4) . ?
C5 H5 0.9800 . ?
C6 C7 1.511(3) . ?
C6 H6 0.9800 . ?
C7 C12 1.377(4) . ?
C7 C8 1.390(4) . ?
C8 C9 1.386(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.368(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.374(4) . ?
C13 C18 1.374(4) . ?
C14 C15 1.389(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.382(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.364(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(4) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
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
_geom_torsion_publ_flag
C13 N3 C2 O2 8.6(4) . . . . ?
C4 N3 C2 O2 -179.0(3) . . . . ?
C13 N3 C2 O1 -174.3(2) . . . . ?
C4 N3 C2 O1 -1.8(4) . . . . ?
C6 O1 C2 O2 -166.0(2) . . . . ?
C6 O1 C2 N3 16.7(3) . . . . ?
C2 N3 C4 C5 17.8(4) . . . . ?
C13 N3 C4 C5 -169.5(2) . . . . ?
N3 C4 C5 O3 -164.4(2) . . . . ?
N3 C4 C5 C6 -45.4(3) . . . . ?
C2 O1 C6 C5 -45.7(3) . . . . ?
C2 O1 C6 C7 -169.4(2) . . . . ?
O3 C5 C6 O1 179.7(2) . . . . ?
C4 C5 C6 O1 58.4(3) . . . . ?
O3 C5 C6 C7 -60.1(3) . . . . ?
C4 C5 C6 C7 178.6(2) . . . . ?
O1 C6 C7 C12 -147.6(3) . . . . ?
C5 C6 C7 C12 91.6(3) . . . . ?
O1 C6 C7 C8 34.7(3) . . . . ?
C5 C6 C7 C8 -86.0(3) . . . . ?
C12 C7 C8 C9 0.9(5) . . . . ?
C6 C7 C8 C9 178.6(3) . . . . ?
C7 C8 C9 C10 -1.7(5) . . . . ?
C8 C9 C10 C11 1.1(6) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C8 C7 C12 C11 0.4(5) . . . . ?
C6 C7 C12 C11 -177.3(3) . . . . ?
C10 C11 C12 C7 -0.9(5) . . . . ?
C2 N3 C13 C14 -112.8(3) . . . . ?
C4 N3 C13 C14 74.1(3) . . . . ?
C2 N3 C13 C18 70.6(3) . . . . ?
C4 N3 C13 C18 -102.5(3) . . . . ?
C18 C13 C14 C15 -0.1(5) . . . . ?
N3 C13 C14 C15 -176.7(3) . . . . ?
C13 C14 C15 C16 -0.4(6) . . . . ?
C14 C15 C16 C17 0.1(6) . . . . ?
C15 C16 C17 C18 0.7(6) . . . . ?
C14 C13 C18 C17 0.9(5) . . . . ?
N3 C13 C18 C17 177.5(3) . . . . ?
C16 C17 C18 C13 -1.2(5) . . . . ?
