# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_6478
_database_code_depnum_ccdc_archive 'CCDC 1901847'
loop_
_audit_author_name
_audit_author_address
'N-para-chloro-substituted fused bicyclic tetrahydroisoxazolo'
;South China Normal University
China
;
_audit_update_record             
;
2019-03-08 deposited with the CCDC.	2019-08-14 downloaded from the CCDC.
;
_audit_creation_date             2019-03-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-1
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H18 Cl N O2'
_chemical_formula_sum            'C23 H18 Cl N O2'
_chemical_formula_weight         375.83
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2832(7)
_cell_length_b                   10.0044(7)
_cell_length_c                   11.1070(9)
_cell_angle_alpha                87.027(6)
_cell_angle_beta                 65.546(8)
_cell_angle_gamma                82.335(6)
_cell_volume                     930.61(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2538
_cell_measurement_temperature    173(13)
_cell_measurement_theta_max      28.7860
_cell_measurement_theta_min      4.0220
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.223
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81504
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7976
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         3.369
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      173(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     35.00  68.00   1.00    5.00    --   15.49 178.00  30.00   33
  2  ω    -52.00  80.00   1.00    5.00    --   15.49   0.00 -60.00  132
  3  ω    -28.00   8.00   1.00    5.00    --  -16.28  38.00-180.00   36
  4  ω     -2.00  42.00   1.00    5.00    --   15.34 -77.00  30.00   44
  5  ω     53.00  78.00   1.00    5.00    --   15.34  57.00 150.00   25
  6  ω      3.00  44.00   1.00    5.00    --   15.34  57.00 150.00   41
  7  ω    -75.00  -3.00   1.00    5.00    --  -15.96 -57.00 -90.00   72
  8  ω    -21.00   1.00   1.00    5.00    --  -15.96 -99.00-180.00   22
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0250204000
_diffrn_orient_matrix_UB_12      0.0302757000
_diffrn_orient_matrix_UB_13      0.0432834000
_diffrn_orient_matrix_UB_21      0.0574752000
_diffrn_orient_matrix_UB_22      -0.0568668000
_diffrn_orient_matrix_UB_23      -0.0072234000
_diffrn_orient_matrix_UB_31      0.0567830000
_diffrn_orient_matrix_UB_32      0.0311005000
_diffrn_orient_matrix_UB_33      -0.0547376000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2911
_reflns_number_total             3900
_reflns_odcompleteness_completeness 98.21
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3900
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0584
_refine_ls_restrained_S_all      1.038
_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)+(0.0398P)²+0.6177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1265
_refine_ls_wR_factor_ref         0.1381
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C14(H14), C23(H23), C22(H22), C15(H15)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C13(H13), C11(H11), C12(H12), C5(H5), C3(H3), C2(H2), C10(H10),
 C6(H6), C20(H20), C17(H17), C19(H19), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.81449(11) 0.27010(10) -0.23814(7) 0.0764(3) Uani 1 1 d . . . . .
O1 O 0.45460(18) 0.34263(17) 0.40844(15) 0.0450(4) Uani 1 1 d . . . . .
O2 O 0.3669(2) 0.11874(16) 0.58409(16) 0.0484(4) Uani 1 1 d . . . . .
N1 N 0.6304(2) 0.32537(18) 0.33836(18) 0.0388(4) Uani 1 1 d . . . . .
C4 C 0.6667(3) 0.3026(2) 0.2020(2) 0.0387(5) Uani 1 1 d . . . . .
C7 C 0.6815(3) 0.2154(2) 0.4115(2) 0.0358(5) Uani 1 1 d . . . . .
H7 H 0.6650 0.1283 0.3860 0.043 Uiso 1 1 calc R . . . .
C8 C 0.8551(3) 0.2158(2) 0.3845(2) 0.0379(5) Uani 1 1 d . . . . .
C14 C 0.5675(3) 0.2481(2) 0.5557(2) 0.0400(5) Uani 1 1 d . . . . .
H14 H 0.6170 0.2933 0.6023 0.048 Uiso 1 1 calc R . . . .
C23 C 0.4247(3) 0.3377(2) 0.5453(2) 0.0412(5) Uani 1 1 d . . . . .
H23 H 0.4073 0.4275 0.5838 0.049 Uiso 1 1 calc R . . . .
C22 C 0.2868(3) 0.2545(3) 0.6213(2) 0.0483(6) Uani 1 1 d . . . . .
H22 H 0.1916 0.2777 0.6034 0.058 Uiso 1 1 calc R . . . .
C15 C 0.4876(3) 0.1262(3) 0.6331(2) 0.0474(6) Uani 1 1 d . . . . .
H15 H 0.5600 0.0430 0.6246 0.057 Uiso 1 1 calc R . . . .
C9 C 0.9563(3) 0.0961(3) 0.3611(3) 0.0504(6) Uani 1 1 d . . . . .
H9 H 0.9189 0.0159 0.3557 0.061 Uiso 1 1 calc R . . . .
C1 C 0.7520(3) 0.2795(3) -0.0666(2) 0.0519(6) Uani 1 1 d . . . . .
C13 C 0.9148(3) 0.3341(3) 0.3912(3) 0.0542(7) Uani 1 1 d . . . . .
H13 H 0.8490 0.4158 0.4074 0.065 Uiso 1 1 calc R . . . .
C11 C 1.1694(3) 0.2106(4) 0.3523(3) 0.0615(8) Uani 1 1 d . . . . .
H11 H 1.2741 0.2084 0.3425 0.074 Uiso 1 1 calc R . . . .
C12 C 1.0733(3) 0.3309(3) 0.3736(3) 0.0632(8) Uani 1 1 d . . . . .
H12 H 1.1133 0.4105 0.3763 0.076 Uiso 1 1 calc R . . . .
C21 C 0.2581(3) 0.2573(3) 0.7658(3) 0.0561(7) Uani 1 1 d . . . . .
C5 C 0.6316(3) 0.4092(3) 0.1311(3) 0.0559(7) Uani 1 1 d . . . . .
H5 H 0.5789 0.4901 0.1742 0.067 Uiso 1 1 calc R . . . .
C16 C 0.3861(3) 0.1743(3) 0.7735(2) 0.0552(7) Uani 1 1 d . . . . .
C3 C 0.7449(3) 0.1829(3) 0.1362(2) 0.0557(7) Uani 1 1 d . . . . .
H3 H 0.7687 0.1096 0.1827 0.067 Uiso 1 1 calc R . . . .
C2 C 0.7882(4) 0.1712(3) 0.0007(3) 0.0634(8) Uani 1 1 d . . . . .
H2 H 0.8411 0.0907 -0.0434 0.076 Uiso 1 1 calc R . . . .
C10 C 1.1124(3) 0.0940(3) 0.3455(3) 0.0630(8) Uani 1 1 d . . . . .
H10 H 1.1787 0.0126 0.3303 0.076 Uiso 1 1 calc R . . . .
C6 C 0.6735(4) 0.3981(3) -0.0030(3) 0.0610(7) Uani 1 1 d . . . . .
H6 H 0.6485 0.4707 -0.0496 0.073 Uiso 1 1 calc R . . . .
C20 C 0.1420(4) 0.3250(3) 0.8760(3) 0.0778(10) Uani 1 1 d . . . . .
H20 H 0.0579 0.3828 0.8704 0.093 Uiso 1 1 calc R . . . .
C17 C 0.4033(5) 0.1565(4) 0.8909(3) 0.0781(10) Uani 1 1 d . . . . .
H17 H 0.4903 0.1025 0.8957 0.094 Uiso 1 1 calc R . . . .
C19 C 0.1565(6) 0.3029(5) 0.9946(4) 0.1021(15) Uani 1 1 d . . . . .
H19 H 0.0775 0.3431 1.0713 0.123 Uiso 1 1 calc R . . . .
C18 C 0.2850(6) 0.2228(5) 1.0017(3) 0.1026(15) Uani 1 1 d . . . . .
H18 H 0.2930 0.2126 1.0825 0.123 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C1 1.751(3) . ?
O1 N1 1.478(2) . ?
O1 C23 1.427(3) . ?
O2 C22 1.450(3) . ?
O2 C15 1.446(3) . ?
N1 C4 1.432(3) . ?
N1 C7 1.477(3) . ?
C4 C5 1.377(3) . ?
C4 C3 1.384(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.513(3) . ?
C7 C14 1.533(3) . ?
C8 C9 1.383(3) . ?
C8 C13 1.390(3) . ?
C14 H14 0.9800 . ?
C14 C23 1.540(3) . ?
C14 C15 1.543(3) . ?
C23 H23 0.9800 . ?
C23 C22 1.537(3) . ?
C22 H22 0.9800 . ?
C22 C21 1.516(4) . ?
C15 H15 0.9800 . ?
C15 C16 1.514(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(4) . ?
C1 C2 1.369(4) . ?
C1 C6 1.367(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.398(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.367(4) . ?
C11 C10 1.361(4) . ?
C12 H12 0.9300 . ?
C21 C16 1.385(4) . ?
C21 C20 1.384(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.381(4) . ?
C16 C17 1.377(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.394(4) . ?
C2 H2 0.9300 . ?
C10 H10 0.9300 . ?
C6 H6 0.9300 . ?
C20 H20 0.9300 . ?
C20 C19 1.383(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.390(5) . ?
C19 H19 0.9300 . ?
C19 C18 1.374(6) . ?
C18 H18 0.9300 . ?

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
C23 O1 N1 104.46(16) . . ?
C15 O2 C22 96.75(17) . . ?
C4 N1 O1 106.53(16) . . ?
C4 N1 C7 117.91(18) . . ?
C7 N1 O1 103.62(15) . . ?
C5 C4 N1 117.7(2) . . ?
C5 C4 C3 118.6(2) . . ?
C3 C4 N1 123.6(2) . . ?
N1 C7 H7 110.1 . . ?
N1 C7 C8 110.46(17) . . ?
N1 C7 C14 102.65(17) . . ?
C8 C7 H7 110.1 . . ?
C8 C7 C14 113.36(18) . . ?
C14 C7 H7 110.1 . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 C13 118.2(2) . . ?
C13 C8 C7 121.3(2) . . ?
C7 C14 H14 112.3 . . ?
C7 C14 C23 104.01(18) . . ?
C7 C14 C15 113.63(19) . . ?
C23 C14 H14 112.3 . . ?
C23 C14 C15 101.46(18) . . ?
C15 C14 H14 112.3 . . ?
O1 C23 C14 106.54(17) . . ?
O1 C23 H23 112.6 . . ?
O1 C23 C22 109.94(19) . . ?
C14 C23 H23 112.6 . . ?
C22 C23 C14 101.92(19) . . ?
C22 C23 H23 112.6 . . ?
O2 C22 C23 100.79(18) . . ?
O2 C22 H22 115.3 . . ?
O2 C22 C21 101.1(2) . . ?
C23 C22 H22 115.3 . . ?
C21 C22 C23 107.1(2) . . ?
C21 C22 H22 115.3 . . ?
O2 C15 C14 101.43(19) . . ?
O2 C15 H15 115.3 . . ?
O2 C15 C16 101.1(2) . . ?
C14 C15 H15 115.3 . . ?
C16 C15 C14 106.6(2) . . ?
C16 C15 H15 115.3 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 121.0(3) . . ?
C10 C9 H9 119.5 . . ?
C2 C1 Cl1 120.0(2) . . ?
C6 C1 Cl1 118.9(2) . . ?
C6 C1 C2 121.1(2) . . ?
C8 C13 H13 119.8 . . ?
C8 C13 C12 120.3(3) . . ?
C12 C13 H13 119.8 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.3(3) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 119.9(3) . . ?
C11 C12 H12 120.0 . . ?
C16 C21 C22 104.9(2) . . ?
C20 C21 C22 133.7(3) . . ?
C20 C21 C16 121.4(3) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(3) . . ?
C6 C5 H5 119.4 . . ?
C21 C16 C15 104.9(2) . . ?
C17 C16 C15 133.7(3) . . ?
C17 C16 C21 121.3(3) . . ?
C4 C3 H3 119.7 . . ?
C4 C3 C2 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C1 C2 C3 119.2(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.9 . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C21 C20 H20 121.4 . . ?
C19 C20 C21 117.1(4) . . ?
C19 C20 H20 121.4 . . ?
C16 C17 H17 121.4 . . ?
C16 C17 C18 117.2(4) . . ?
C18 C17 H17 121.4 . . ?
C20 C19 H19 119.3 . . ?
C18 C19 C20 121.5(3) . . ?
C18 C19 H19 119.3 . . ?
C17 C18 H18 119.3 . . ?
C19 C18 C17 121.5(4) . . ?
C19 C18 H18 119.3 . . ?

_olex2_date_sample_data_collection 2019-03-05
_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 1.465
_oxdiff_exptl_absorpt_empirical_full_min 0.816
