#------------------------------------------------------------------------------
#$Date: 2021-05-05 12:04:01 +0300 (Wed, 05 May 2021) $
#$Revision: 264952 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157974.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_7157974
loop_
_publ_author_name
'Qiu, Shaotong'
'Cao, Tongxiang'
'Zhu, Shifa'
_publ_section_title
;
 Catalyst-free synthesis of isoxazolidine from nitrosoarene and haloalkyne
 via a 1,2-halo-migration/[3 + 2] cycloaddition cascade.
;
_journal_issue                   14
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3139
_journal_page_last               3143
_journal_paper_doi               10.1039/d1ob00421b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C19 H17 Br N2 O3'
_chemical_formula_sum            'C19 H17 Br N2 O3'
_chemical_formula_weight         401.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-08-15 deposited with the CCDC.	2021-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.834(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4819(3)
_cell_length_b                   5.4926(2)
_cell_length_c                   25.2518(7)
_cell_measurement_reflns_used    3261
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.3840
_cell_measurement_theta_min      3.5600
_cell_volume                     1694.42(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     70.00 119.00   1.00    1.00    --   40.98  19.00 120.00   49
  2  ω    124.00 164.00   1.00    1.00    --  106.95 125.00   0.00   40
  3  ω    105.00 168.00   1.00    1.00    --  106.95 125.00 120.00   63
  4  ω     81.00 178.00   1.00    1.00    --  106.95  45.00 -90.00   97
  5  ω    138.00 165.00   1.00    1.00    --  106.95 125.00-120.00   27
  6  ω     36.00 130.00   1.00    1.00    --  106.95 -61.00 120.00   94
  7  ω     25.00  96.00   1.00    1.00    --   40.98-125.00 150.00   71
  8  ω     28.00 104.00   1.00    1.00    --  106.95 -94.00  60.00   76
  9  ω      6.00  35.00   1.00    1.00    --   40.98 -99.00-180.00   29
 10  ω    -24.00  65.00   1.00    1.00    --   40.98 -57.00-150.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1089999000
_diffrn_orient_matrix_UB_12      0.1398479000
_diffrn_orient_matrix_UB_13      0.0148480000
_diffrn_orient_matrix_UB_21      0.0163343000
_diffrn_orient_matrix_UB_22      -0.0282852000
_diffrn_orient_matrix_UB_23      -0.0585140000
_diffrn_orient_matrix_UB_31      -0.0612858000
_diffrn_orient_matrix_UB_32      0.2415083000
_diffrn_orient_matrix_UB_33      -0.0154983000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0406
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            5983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.578
_diffrn_reflns_theta_min         3.577
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.488
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3295
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0308
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0376P)²+0.2301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0772
_refine_ls_wR_factor_ref         0.0817
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2860
_reflns_number_total             3295
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00421b2.cif
_cod_data_source_block           9st229
_cod_depositor_comments
'Adding full bibliography for 7157974--7157975.cif.'
_cod_database_code               7157974
_shelx_shelxl_version_number     2018/3
_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.
;
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C6(H6), C3(H3A), C14(H14), C10(H10), C13(H13),
 C12(H12), C11(H11)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.752
_oxdiff_exptl_absorpt_empirical_full_min 0.649
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
Br1 Br 1.00809(2) 0.83291(5) 0.25228(2) 0.02924(10) Uani 1 1 d . . . . .
O2 O 0.99036(12) 0.8322(3) 0.55393(6) 0.0235(3) Uani 1 1 d . . . . .
O1 O 0.63445(12) 1.0823(3) 0.50763(6) 0.0237(3) Uani 1 1 d . . . . .
O3 O 0.86220(12) 0.4584(3) 0.48426(6) 0.0227(3) Uani 1 1 d . . . . .
H3 H 0.912011 0.407255 0.470603 0.034 Uiso 1 1 calc GR . . . .
N2 N 0.81941(14) 1.0021(4) 0.53883(6) 0.0182(4) Uani 1 1 d . . . . .
N1 N 0.54474(15) 0.7778(4) 0.41969(7) 0.0237(4) Uani 1 1 d . . . . .
H1 H 0.533799 0.912690 0.435023 0.028 Uiso 1 1 calc R . . . .
C1 C 0.75382(16) 0.5817(4) 0.35388(7) 0.0182(4) Uani 1 1 d . . . . .
C16 C 0.71723(16) 0.9726(4) 0.50275(8) 0.0180(4) Uani 1 1 d . . . . .
C2 C 0.73923(17) 0.7977(4) 0.32478(8) 0.0202(4) Uani 1 1 d . . . . .
H2 H 0.678406 0.894003 0.325815 0.024 Uiso 1 1 calc R . . . .
C4 C 0.90445(17) 0.7272(5) 0.29327(8) 0.0212(5) Uani 1 1 d . . . . .
C9 C 0.45150(17) 0.6510(4) 0.38956(8) 0.0194(4) Uani 1 1 d . . . . .
C17 C 0.89738(17) 0.8517(4) 0.52679(8) 0.0188(4) Uani 1 1 d . . . . .
C18 C 0.84979(17) 0.7121(4) 0.47493(8) 0.0187(4) Uani 1 1 d . . . . .
H18 H 0.885433 0.762199 0.445532 0.022 Uiso 1 1 calc R . . . .
C15 C 0.73248(17) 0.7919(4) 0.46363(8) 0.0180(4) Uani 1 1 d . . . . .
C8 C 0.64910(17) 0.6973(4) 0.42540(8) 0.0181(4) Uani 1 1 d . . . . .
C5 C 0.92105(17) 0.5102(4) 0.32135(8) 0.0219(5) Uani 1 1 d . . . . .
H5 H 0.981905 0.414356 0.320113 0.026 Uiso 1 1 calc R . . . .
C7 C 0.67184(17) 0.5008(4) 0.38722(8) 0.0197(4) Uani 1 1 d . . . . .
H7A H 0.603838 0.455950 0.363055 0.024 Uiso 1 1 calc R . . . .
H7B H 0.699876 0.357594 0.408001 0.024 Uiso 1 1 calc R . . . .
C6 C 0.84490(17) 0.4374(4) 0.35161(8) 0.0201(4) Uani 1 1 d . . . . .
H6 H 0.854891 0.291070 0.370503 0.024 Uiso 1 1 calc R . . . .
C3 C 0.81369(18) 0.8728(4) 0.29415(8) 0.0222(5) Uani 1 1 d . . . . .
H3A H 0.803097 1.017397 0.274619 0.027 Uiso 1 1 calc R . . . .
C19 C 0.83902(18) 1.1719(4) 0.58418(8) 0.0223(5) Uani 1 1 d . . . . .
H19A H 0.774497 1.267941 0.583556 0.033 Uiso 1 1 calc GR . . . .
H19B H 0.899025 1.277021 0.581322 0.033 Uiso 1 1 calc GR . . . .
H19C H 0.856429 1.082661 0.617529 0.033 Uiso 1 1 calc GR . . . .
C14 C 0.39469(17) 0.7459(5) 0.34109(8) 0.0224(5) Uani 1 1 d . . . . .
H14 H 0.417426 0.890471 0.327684 0.027 Uiso 1 1 calc R . . . .
C10 C 0.41886(18) 0.4332(4) 0.40924(8) 0.0241(5) Uani 1 1 d . . . . .
H10 H 0.457317 0.370179 0.441819 0.029 Uiso 1 1 calc R . . . .
C13 C 0.30301(18) 0.6229(5) 0.31253(8) 0.0280(5) Uani 1 1 d . . . . .
H13 H 0.263734 0.687163 0.280267 0.034 Uiso 1 1 calc R . . . .
C12 C 0.27041(19) 0.4062(5) 0.33199(9) 0.0298(6) Uani 1 1 d . . . . .
H12 H 0.209373 0.324348 0.312861 0.036 Uiso 1 1 calc R . . . .
C11 C 0.3293(2) 0.3106(5) 0.38037(10) 0.0285(5) Uani 1 1 d . . . . .
H11 H 0.308050 0.163421 0.393263 0.034 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C18 O3 H3 109.5 . . ?
C16 N2 C19 124.20(18) . . ?
C17 N2 C16 112.26(17) . . ?
C17 N2 C19 123.54(17) . . ?
C9 N1 H1 118.1 . . ?
C8 N1 H1 118.1 . . ?
C8 N1 C9 123.79(19) . . ?
C2 C1 C7 120.9(2) . . ?
C2 C1 C6 118.9(2) . . ?
C6 C1 C7 120.2(2) . . ?
O1 C16 N2 123.11(19) . . ?
O1 C16 C15 129.90(19) . . ?
N2 C16 C15 106.96(17) . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.3(2) . . ?
C3 C2 H2 119.4 . . ?
C5 C4 Br1 119.66(17) . . ?
C5 C4 C3 121.7(2) . . ?
C3 C4 Br1 118.65(18) . . ?
C14 C9 N1 119.9(2) . . ?
C14 C9 C10 120.4(2) . . ?
C10 C9 N1 119.64(19) . . ?
O2 C17 N2 124.63(19) . . ?
O2 C17 C18 126.3(2) . . ?
N2 C17 C18 109.06(17) . . ?
O3 C18 C17 109.94(16) . . ?
O3 C18 H18 110.6 . . ?
O3 C18 C15 112.87(18) . . ?
C17 C18 H18 110.6 . . ?
C15 C18 C17 102.08(17) . . ?
C15 C18 H18 110.6 . . ?
C16 C15 C18 109.41(17) . . ?
C8 C15 C16 123.86(19) . . ?
C8 C15 C18 126.52(19) . . ?
N1 C8 C15 121.8(2) . . ?
N1 C8 C7 117.83(18) . . ?
C15 C8 C7 120.38(19) . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.8(2) . . ?
C6 C5 H5 120.6 . . ?
C1 C7 H7A 109.1 . . ?
C1 C7 H7B 109.1 . . ?
C8 C7 C1 112.35(18) . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.9 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C2 C3 C4 118.6(2) . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 H3A 120.7 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 C14 H14 120.3 . . ?
C9 C14 C13 119.4(2) . . ?
C13 C14 H14 120.3 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10 120.1 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.3(2) . . ?
C12 C13 H13 119.9 . . ?
C13 C12 H12 120.1 . . ?
C13 C12 C11 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
C10 C11 C12 120.3(2) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
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
Br1 C4 1.906(2) . ?
O2 C17 1.226(3) . ?
O1 C16 1.224(3) . ?
O3 H3 0.8200 . ?
O3 C18 1.417(3) . ?
N2 C16 1.416(2) . ?
N2 C17 1.357(3) . ?
N2 C19 1.458(3) . ?
N1 H1 0.8600 . ?
N1 C9 1.433(3) . ?
N1 C8 1.355(3) . ?
C1 C2 1.388(3) . ?
C1 C7 1.519(3) . ?
C1 C6 1.396(3) . ?
C16 C15 1.440(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(3) . ?
C4 C5 1.380(3) . ?
C4 C3 1.390(3) . ?
C9 C14 1.384(3) . ?
C9 C10 1.388(3) . ?
C17 C18 1.529(3) . ?
C18 H18 0.9800 . ?
C18 C15 1.499(3) . ?
C15 C8 1.369(3) . ?
C8 C7 1.512(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.395(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C6 H6 0.9300 . ?
C3 H3A 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C13 1.396(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.380(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.393(3) . ?
C11 H11 0.9300 . ?
