#------------------------------------------------------------------------------
#$Date: 2023-06-05 06:56:22 +0200 (Mon 05 de Jun de 2023) $
#$Revision: 284325 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/93/7159308.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_7159308
loop_
_publ_author_name
'Lukoyanov, Alexander A.'
'Tabolin, Andrey A.'
'Nelyubina, Yulia V.'
'Aksenova, Svetlana A.'
'Sukhorukov, Alexey Yu'
_publ_section_title
;
 Nitronate-aryne cycloaddition as a concise route to stereochemically
 complex fused benzisoxazolines and amino alcohols.
;
_journal_issue                   18
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              3871
_journal_page_last               3880
_journal_paper_doi               10.1039/d3ob00235g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C19 H20 Cl N O2'
_chemical_formula_sum            'C19 H20 Cl N O2'
_chemical_formula_weight         329.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-01-25 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.9610(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4108(6)
_cell_length_b                   7.4249(5)
_cell_length_c                   23.5740(16)
_cell_measurement_reflns_used    6252
_cell_measurement_temperature    120.15
_cell_measurement_theta_max      30.40
_cell_measurement_theta_min      2.58
_cell_volume                     1627.11(19)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16452
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.996
_diffrn_reflns_theta_min         1.749
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6471
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0676 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.8673.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3551
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0333
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0295P)²+0.9035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0802
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3111
_reflns_number_total             3551
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00235g2.cif
_cod_data_source_block           AL001
_cod_depositor_comments
'Adding full bibliography for 7159308--7159315.cif.'
_cod_database_code               7159308
_shelxl_version_number           2014/6
_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_max   0.988
_shelx_estimated_absorpt_t_min   0.941
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C10(H10), C17(H17), C18(H18), C9(H9), C8(H8), C7(H7)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C12(H12A,H12B,H12C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Cl1 Cl -0.04791(4) -0.02127(5) 0.66562(2) 0.02298(10) Uani 1 1 d . . . . .
O1 O 0.50878(10) 0.88960(13) 0.58897(4) 0.0196(2) Uani 1 1 d . . . . .
O2 O 0.66323(10) 0.71616(12) 0.65266(4) 0.0164(2) Uani 1 1 d . . . . .
N1 N 0.53283(12) 0.80719(15) 0.64796(5) 0.0157(2) Uani 1 1 d . . . . .
C2 C 0.30470(14) 0.72447(17) 0.59580(5) 0.0140(3) Uani 1 1 d . . . . .
C15 C 0.15324(15) 0.14004(18) 0.61243(6) 0.0169(3) Uani 1 1 d . . . . .
H15 H 0.1139 0.0727 0.5794 0.020 Uiso 1 1 calc R U . . .
C13 C 0.32920(14) 0.35493(17) 0.65877(6) 0.0147(3) Uani 1 1 d . . . . .
C14 C 0.26840(14) 0.25672(18) 0.61059(6) 0.0160(3) Uani 1 1 d . . . . .
H14 H 0.3064 0.2697 0.5758 0.019 Uiso 1 1 calc R U . . .
C1 C 0.37515(14) 0.83905(18) 0.56303(6) 0.0156(3) Uani 1 1 d . . . . .
C10 C 0.16469(15) 0.67129(18) 0.57538(6) 0.0166(3) Uani 1 1 d . . . . .
H10 H 0.1141 0.5950 0.5977 0.020 Uiso 1 1 calc R U . . .
C16 C 0.09711(14) 0.12378(18) 0.66306(6) 0.0169(3) Uani 1 1 d . . . . .
C17 C 0.15599(15) 0.21746(18) 0.71191(6) 0.0190(3) Uani 1 1 d . . . . .
H17 H 0.1171 0.2047 0.7465 0.023 Uiso 1 1 calc R U . . .
C18 C 0.27248(15) 0.33005(18) 0.70962(6) 0.0176(3) Uani 1 1 d . . . . .
H18 H 0.3147 0.3917 0.7434 0.021 Uiso 1 1 calc R U . . .
C4 C 0.45287(14) 0.48476(17) 0.65693(5) 0.0138(3) Uani 1 1 d . . . . .
H4 H 0.5197 0.4731 0.6941 0.017 Uiso 1 1 calc R U . . .
C9 C 0.09940(15) 0.73162(19) 0.52156(6) 0.0185(3) Uani 1 1 d . . . . .
H9 H 0.0035 0.6966 0.5071 0.022 Uiso 1 1 calc R U . . .
C3 C 0.40217(14) 0.68428(17) 0.65129(6) 0.0143(3) Uani 1 1 d . . . . .
C19 C 0.34131(15) 0.75195(18) 0.70378(6) 0.0180(3) Uani 1 1 d . . . . .
H19A H 0.4077 0.7212 0.7387 0.027 Uiso 1 1 calc R U . . .
H19B H 0.2478 0.6951 0.7050 0.027 Uiso 1 1 calc R U . . .
H19C H 0.3293 0.8830 0.7013 0.027 Uiso 1 1 calc R U . . .
C5 C 0.53976(14) 0.44533(18) 0.60854(6) 0.0163(3) Uani 1 1 d . . . . .
H5A H 0.5645 0.3157 0.6088 0.020 Uiso 1 1 calc R U . . .
H5B H 0.4808 0.4737 0.5711 0.020 Uiso 1 1 calc R U . . .
C8 C 0.17418(15) 0.84297(19) 0.48891(6) 0.0194(3) Uani 1 1 d . . . . .
H8 H 0.1289 0.8813 0.4520 0.023 Uiso 1 1 calc R U . . .
C7 C 0.31367(15) 0.89909(19) 0.50916(6) 0.0188(3) Uani 1 1 d . . . . .
H7 H 0.3647 0.9754 0.4870 0.023 Uiso 1 1 calc R U . . .
C6 C 0.67787(15) 0.55753(18) 0.61592(6) 0.0172(3) Uani 1 1 d . . . . .
C12 C 0.71753(17) 0.6181(2) 0.55861(6) 0.0236(3) Uani 1 1 d . . . . .
H12A H 0.6343 0.6763 0.5357 0.035 Uiso 1 1 calc R U . . .
H12B H 0.7462 0.5132 0.5378 0.035 Uiso 1 1 calc R U . . .
H12C H 0.7977 0.7037 0.5655 0.035 Uiso 1 1 calc R U . . .
C11 C 0.80321(16) 0.4577(2) 0.65086(7) 0.0244(3) Uani 1 1 d . . . . .
H11A H 0.8864 0.5384 0.6586 0.037 Uiso 1 1 calc R U . . .
H11B H 0.8282 0.3529 0.6292 0.037 Uiso 1 1 calc R U . . .
H11C H 0.7757 0.4177 0.6872 0.037 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'
Cl Cl 0.1484 0.1585 '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
C1 O1 N1 107.36(9) . . ?
N1 O2 C6 120.09(10) . . ?
O1 N1 C3 106.35(9) . . ?
O2 N1 O1 105.99(9) . . ?
O2 N1 C3 114.13(10) . . ?
C1 C2 C10 119.49(12) . . ?
C1 C2 C3 109.05(11) . . ?
C10 C2 C3 131.43(12) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C16 C15 C14 118.97(13) . . ?
C14 C13 C18 117.77(12) . . ?
C14 C13 C4 121.87(12) . . ?
C18 C13 C4 120.36(12) . . ?
C15 C14 C13 121.46(12) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
O1 C1 C2 114.03(12) . . ?
O1 C1 C7 123.20(12) . . ?
C7 C1 C2 122.77(13) . . ?
C2 C10 H10 120.5 . . ?
C2 C10 C9 118.95(12) . . ?
C9 C10 H10 120.5 . . ?
C15 C16 Cl1 119.27(11) . . ?
C15 C16 C17 121.09(13) . . ?
C17 C16 Cl1 119.63(11) . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.13(13) . . ?
C18 C17 H17 120.4 . . ?
C13 C18 H18 119.2 . . ?
C17 C18 C13 121.52(13) . . ?
C17 C18 H18 119.2 . . ?
C13 C4 H4 107.5 . . ?
C13 C4 C3 112.40(10) . . ?
C13 C4 C5 113.63(11) . . ?
C3 C4 H4 107.5 . . ?
C5 C4 H4 107.5 . . ?
C5 C4 C3 108.10(10) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.29(13) . . ?
C8 C9 H9 119.9 . . ?
N1 C3 C4 109.34(10) . . ?
C2 C3 N1 102.76(10) . . ?
C2 C3 C4 113.58(11) . . ?
C2 C3 C19 112.59(11) . . ?
C19 C3 N1 104.43(10) . . ?
C19 C3 C4 113.13(11) . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 C4 110.71(11) . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C9 C8 H8 119.3 . . ?
C7 C8 C9 121.33(13) . . ?
C7 C8 H8 119.3 . . ?
C1 C7 C8 117.14(13) . . ?
C1 C7 H7 121.4 . . ?
C8 C7 H7 121.4 . . ?
O2 C6 C5 110.15(10) . . ?
O2 C6 C12 109.98(11) . . ?
O2 C6 C11 101.87(11) . . ?
C12 C6 C5 112.37(12) . . ?
C11 C6 C5 111.67(12) . . ?
C11 C6 C12 110.31(12) . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
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
Cl1 C16 1.7470(14) . ?
O1 N1 1.5038(14) . ?
O1 C1 1.3627(16) . ?
O2 N1 1.3902(14) . ?
O2 C6 1.4811(16) . ?
N1 C3 1.5431(17) . ?
C2 C1 1.3855(18) . ?
C2 C10 1.3878(19) . ?
C2 C3 1.5060(18) . ?
C15 H15 0.9500 . ?
C15 C14 1.3934(19) . ?
C15 C16 1.3836(19) . ?
C13 C14 1.3952(19) . ?
C13 C18 1.3984(19) . ?
C13 C4 1.5171(18) . ?
C14 H14 0.9500 . ?
C1 C7 1.3847(19) . ?
C10 H10 0.9500 . ?
C10 C9 1.3948(19) . ?
C16 C17 1.385(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(2) . ?
C18 H18 0.9500 . ?
C4 H4 1.0000 . ?
C4 C3 1.5557(18) . ?
C4 C5 1.5316(18) . ?
C9 H9 0.9500 . ?
C9 C8 1.393(2) . ?
C3 C19 1.5271(18) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5307(19) . ?
C8 H8 0.9500 . ?
C8 C7 1.389(2) . ?
C7 H7 0.9500 . ?
C6 C12 1.5245(19) . ?
C6 C11 1.5218(19) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
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
Cl1 C16 C17 C18 179.00(10) . . . . ?
O1 N1 C3 C2 -6.61(12) . . . . ?
O1 N1 C3 C4 114.34(10) . . . . ?
O1 N1 C3 C19 -124.31(10) . . . . ?
O1 C1 C7 C8 -177.27(12) . . . . ?
O2 N1 C3 C2 -123.09(11) . . . . ?
O2 N1 C3 C4 -2.15(14) . . . . ?
O2 N1 C3 C19 119.20(11) . . . . ?
N1 O1 C1 C2 -2.65(14) . . . . ?
N1 O1 C1 C7 176.22(12) . . . . ?
N1 O2 C6 C5 -37.95(15) . . . . ?
N1 O2 C6 C12 86.44(14) . . . . ?
N1 O2 C6 C11 -156.58(11) . . . . ?
C2 C1 C7 C8 1.5(2) . . . . ?
C2 C10 C9 C8 0.2(2) . . . . ?
C15 C16 C17 C18 0.4(2) . . . . ?
C13 C4 C3 N1 -178.39(10) . . . . ?
C13 C4 C3 C2 -64.27(14) . . . . ?
C13 C4 C3 C19 65.69(14) . . . . ?
C13 C4 C5 C6 -169.44(11) . . . . ?
C14 C15 C16 Cl1 179.65(10) . . . . ?
C14 C15 C16 C17 -1.8(2) . . . . ?
C14 C13 C18 C17 -2.6(2) . . . . ?
C14 C13 C4 C3 100.69(14) . . . . ?
C14 C13 C4 C5 -22.48(17) . . . . ?
C1 O1 N1 O2 127.71(10) . . . . ?
C1 O1 N1 C3 5.89(12) . . . . ?
C1 C2 C10 C9 1.45(19) . . . . ?
C1 C2 C3 N1 5.27(13) . . . . ?
C1 C2 C3 C4 -112.72(12) . . . . ?
C1 C2 C3 C19 117.05(12) . . . . ?
C10 C2 C1 O1 176.50(11) . . . . ?
C10 C2 C1 C7 -2.4(2) . . . . ?
C10 C2 C3 N1 -172.81(13) . . . . ?
C10 C2 C3 C4 69.20(18) . . . . ?
C10 C2 C3 C19 -61.03(18) . . . . ?
C10 C9 C8 C7 -1.1(2) . . . . ?
C16 C15 C14 C13 0.9(2) . . . . ?
C16 C17 C18 C13 1.8(2) . . . . ?
C18 C13 C14 C15 1.19(19) . . . . ?
C18 C13 C4 C3 -79.41(15) . . . . ?
C18 C13 C4 C5 157.42(12) . . . . ?
C4 C13 C14 C15 -178.91(12) . . . . ?
C4 C13 C18 C17 177.52(12) . . . . ?
C4 C5 C6 O2 -21.23(15) . . . . ?
C4 C5 C6 C12 -144.23(12) . . . . ?
C4 C5 C6 C11 91.20(13) . . . . ?
C9 C8 C7 C1 0.2(2) . . . . ?
C3 C2 C1 O1 -1.84(15) . . . . ?
C3 C2 C1 C7 179.28(12) . . . . ?
C3 C2 C10 C9 179.36(13) . . . . ?
C3 C4 C5 C6 65.07(14) . . . . ?
C5 C4 C3 N1 -52.18(13) . . . . ?
C5 C4 C3 C2 61.94(14) . . . . ?
C5 C4 C3 C19 -168.10(11) . . . . ?
C6 O2 N1 O1 -65.80(12) . . . . ?
C6 O2 N1 C3 50.90(14) . . . . ?
