# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_lcj-0910-4-2-r
_database_code_depnum_ccdc_archive 'CCDC 2131243'
loop_
_audit_author_name
_audit_author_address
'lipeng long'
;xia men university
China
;
_audit_update_record             
;
2021-12-28 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;
_audit_creation_date             2021-10-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 F4 N2 O'
_chemical_formula_sum            'C9 H6 F4 N2 O'
_chemical_formula_weight         234.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N'
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'
F F 0.0171 0.0103 '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                   6.2144(4)
_cell_length_b                   8.2329(4)
_cell_length_c                   10.3279(6)
_cell_angle_alpha                70.410(5)
_cell_angle_beta                 72.569(6)
_cell_angle_gamma                86.651(5)
_cell_volume                     474.44(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2008
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.9040
_cell_measurement_theta_min      2.2140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87022
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.60a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.639
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6312
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.493
_diffrn_reflns_theta_min         2.192
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     49.00  85.00   0.50    2.00    --   20.00  54.00-120.00   72
  2  ω    -73.00   1.00   0.50    2.00    --   20.00  54.00   0.00  148
  3  ω     13.00  71.00   0.50    2.00    --   20.00  54.00   0.00  116
  4  ω    -65.00 -39.00   0.50    2.00    --   20.00  54.00 120.00   52
  5  ω    -22.00 105.00   0.50    2.00    --   20.00  54.00 120.00  254
  6  ω    -72.00  96.00   0.50    2.00    --   20.00  54.00 -60.00  336
  7  ω    -70.00 -23.00   0.50    2.00    --   20.00  54.00-180.00   94
  8  ω     47.00 103.00   0.50    2.00    --   20.00  54.00-180.00  112
  9  ω     24.00 107.00   0.50    2.00    --   20.00  54.00 150.00  166
 10  ω     63.00  88.00   0.50    2.00    --   20.00  54.00  60.00   50
 11  ω    -74.00 -48.00   0.50    2.00    --   20.00  54.00 -90.00   52
 12  ω    -74.00  30.00   0.50    2.00    --   20.00  54.00  90.00  208
 13  ω    -69.00  28.00   0.50    2.00    --   20.00  54.00-120.00  194
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0319658000
_diffrn_orient_matrix_UB_12      -0.0567281000
_diffrn_orient_matrix_UB_13      -0.0304369000
_diffrn_orient_matrix_UB_21      0.0406029000
_diffrn_orient_matrix_UB_22      -0.0703924000
_diffrn_orient_matrix_UB_23      0.0470397000
_diffrn_orient_matrix_UB_31      -0.1080394000
_diffrn_orient_matrix_UB_32      -0.0144135000
_diffrn_orient_matrix_UB_33      0.0518803000
_diffrn_oxdiff_digest_frames     
;
01e8bf2c569b1799871250ea878de9098b01854ec1c
;
_diffrn_oxdiff_digest_hkl        
;
014975a85a7cce4e1ccfe1c449d96e7dffb4eb
;
_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              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1142
_reflns_number_total             1934
_reflns_odcompleteness_completeness 98.97
_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 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1934
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.055
_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)+(0.0736P)²+0.0438P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1287
_refine_ls_wR_factor_ref         0.1503
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C00F(H00A,H00B,H00C), C00G(H00D,H00E,H00F)
;
_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
F001 F 0.8353(2) 0.3119(2) 0.61339(15) 0.0789(5) Uani 1 1 d . . . . .
F002 F 0.1740(2) 0.1834(2) 0.39800(15) 0.0777(5) Uani 1 1 d . . . . .
O003 O 0.8319(2) 0.4941(2) 0.31300(16) 0.0556(4) Uani 1 1 d . . . . .
F004 F 0.4867(3) 0.0711(2) 0.78312(15) 0.0882(5) Uani 1 1 d . . . . .
F005 F 0.1643(2) 0.0095(2) 0.67603(16) 0.0850(5) Uani 1 1 d . . . . .
N006 N 0.5596(3) 0.4494(2) 0.21824(19) 0.0541(5) Uani 1 1 d . . . . .
N007 N 0.8659(3) 0.6557(3) 0.0760(2) 0.0644(6) Uani 1 1 d . . . . .
C008 C 0.5119(3) 0.3404(3) 0.3616(2) 0.0501(6) Uani 1 1 d . . . . .
C009 C 0.6767(3) 0.3676(3) 0.4193(2) 0.0496(5) Uani 1 1 d . . . . .
C00A C 0.7473(4) 0.5350(3) 0.1963(2) 0.0537(6) Uani 1 1 d . . . . .
C00B C 0.3374(4) 0.2192(3) 0.4480(2) 0.0563(6) Uani 1 1 d . . . . .
C00C C 0.6753(4) 0.2808(3) 0.5599(2) 0.0562(6) Uani 1 1 d . . . . .
C00D C 0.4977(4) 0.1608(3) 0.6448(2) 0.0615(7) Uani 1 1 d . . . . .
C00E C 0.3324(4) 0.1300(3) 0.5893(3) 0.0610(6) Uani 1 1 d . . . . .
C00F C 1.0751(4) 0.7385(4) 0.0663(3) 0.0777(8) Uani 1 1 d . . . . .
H00A H 1.041240 0.842373 0.089803 0.117 Uiso 1 1 calc GR . . . .
H00B H 1.175656 0.766176 -0.029810 0.117 Uiso 1 1 calc GR . . . .
H00C H 1.145651 0.661226 0.132715 0.117 Uiso 1 1 calc GR . . . .
C00G C 0.7752(5) 0.7168(4) -0.0463(3) 0.0768(8) Uani 1 1 d . . . . .
H00D H 0.668427 0.631588 -0.038233 0.115 Uiso 1 1 calc GR . . . .
H00E H 0.896131 0.736369 -0.134149 0.115 Uiso 1 1 calc GR . . . .
H00F H 0.701343 0.822708 -0.046926 0.115 Uiso 1 1 calc GR . . . .


_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
F001 C00C 1.347(3) . ?
F002 C00B 1.355(3) . ?
O003 C009 1.391(3) . ?
O003 C00A 1.389(3) . ?
F004 C00D 1.353(2) . ?
F005 C00E 1.358(3) . ?
N006 C008 1.401(3) . ?
N006 C00A 1.319(3) . ?
N007 C00A 1.335(3) . ?
N007 C00F 1.465(3) . ?
N007 C00G 1.461(3) . ?
C008 C009 1.390(3) . ?
C008 C00B 1.385(3) . ?
C009 C00C 1.385(3) . ?
C00B C00E 1.387(3) . ?
C00C C00D 1.389(3) . ?
C00D C00E 1.389(4) . ?
C00F H00A 0.9600 . ?
C00F H00B 0.9600 . ?
C00F H00C 0.9600 . ?
C00G H00D 0.9600 . ?
C00G H00E 0.9600 . ?
C00G H00F 0.9600 . ?

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
C00A O003 C009 102.98(16) . . ?
C00A N006 C008 103.51(17) . . ?
C00A N007 C00F 122.2(2) . . ?
C00A N007 C00G 118.9(2) . . ?
C00G N007 C00F 118.8(2) . . ?
C009 C008 N006 109.57(19) . . ?
C00B C008 N006 131.6(2) . . ?
C00B C008 C009 118.8(2) . . ?
C008 C009 O003 108.17(18) . . ?
C00C C009 O003 128.3(2) . . ?
C00C C009 C008 123.5(2) . . ?
N006 C00A O003 115.8(2) . . ?
N006 C00A N007 128.1(2) . . ?
N007 C00A O003 116.1(2) . . ?
F002 C00B C008 122.0(2) . . ?
F002 C00B C00E 119.2(2) . . ?
C008 C00B C00E 118.8(2) . . ?
F001 C00C C009 122.2(2) . . ?
F001 C00C C00D 121.2(2) . . ?
C009 C00C C00D 116.7(2) . . ?
F004 C00D C00C 119.6(2) . . ?
F004 C00D C00E 119.5(2) . . ?
C00E C00D C00C 120.9(2) . . ?
F005 C00E C00B 120.1(2) . . ?
F005 C00E C00D 118.6(2) . . ?
C00B C00E C00D 121.3(2) . . ?
N007 C00F H00A 109.5 . . ?
N007 C00F H00B 109.5 . . ?
N007 C00F H00C 109.5 . . ?
H00A C00F H00B 109.5 . . ?
H00A C00F H00C 109.5 . . ?
H00B C00F H00C 109.5 . . ?
N007 C00G H00D 109.5 . . ?
N007 C00G H00E 109.5 . . ?
N007 C00G H00F 109.5 . . ?
H00D C00G H00E 109.5 . . ?
H00D C00G H00F 109.5 . . ?
H00E C00G H00F 109.5 . . ?

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
F001 C00C C00D F004 -1.2(3) . . . . ?
F001 C00C C00D C00E 179.6(2) . . . . ?
F002 C00B C00E F005 -0.5(3) . . . . ?
F002 C00B C00E C00D 179.2(2) . . . . ?
O003 C009 C00C F001 0.3(4) . . . . ?
O003 C009 C00C C00D 179.3(2) . . . . ?
F004 C00D C00E F005 -0.3(3) . . . . ?
F004 C00D C00E C00B 180.0(2) . . . . ?
N006 C008 C009 O003 -0.2(2) . . . . ?
N006 C008 C009 C00C 179.13(19) . . . . ?
N006 C008 C00B F002 1.8(4) . . . . ?
N006 C008 C00B C00E -179.3(2) . . . . ?
C008 N006 C00A O003 -0.2(2) . . . . ?
C008 N006 C00A N007 179.7(2) . . . . ?
C008 C009 C00C F001 -178.89(19) . . . . ?
C008 C009 C00C C00D 0.1(3) . . . . ?
C008 C00B C00E F005 -179.5(2) . . . . ?
C008 C00B C00E C00D 0.2(4) . . . . ?
C009 O003 C00A N006 0.1(2) . . . . ?
C009 O003 C00A N007 -179.83(19) . . . . ?
C009 C008 C00B F002 -178.53(19) . . . . ?
C009 C008 C00B C00E 0.4(3) . . . . ?
C009 C00C C00D F004 179.80(19) . . . . ?
C009 C00C C00D C00E 0.5(4) . . . . ?
C00A O003 C009 C008 0.0(2) . . . . ?
C00A O003 C009 C00C -179.2(2) . . . . ?
C00A N006 C008 C009 0.2(2) . . . . ?
C00A N006 C008 C00B 180.0(2) . . . . ?
C00B C008 C009 O003 -179.93(19) . . . . ?
C00B C008 C009 C00C -0.6(3) . . . . ?
C00C C00D C00E F005 179.0(2) . . . . ?
C00C C00D C00E C00B -0.8(4) . . . . ?
C00F N007 C00A O003 1.0(3) . . . . ?
C00F N007 C00A N006 -178.9(2) . . . . ?
C00G N007 C00A O003 -174.2(2) . . . . ?
C00G N007 C00A N006 5.9(4) . . . . ?

_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 1.178
_oxdiff_exptl_absorpt_empirical_full_min 0.878
####################################################################### 
# 
# 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_lcj_210903_2_r
_database_code_depnum_ccdc_archive 'CCDC 2132707'
loop_
_audit_author_name
_audit_author_address
'lipeng long'
;xia men university
China
;
_audit_update_record             
;
2022-01-06 deposited with the CCDC.	2022-03-15 downloaded from the CCDC.
;
_audit_creation_date             2022-01-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H9 Cl N2 O'
_chemical_formula_sum            'C9 H10 Cl N2 O'
_chemical_formula_weight         197.64
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Cl'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   10.2788(8)
_cell_length_b                   7.8203(7)
_cell_length_c                   12.2421(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.159(8)
_cell_angle_gamma                90
_cell_volume                     968.63(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2574
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.7990
_cell_measurement_theta_min      2.0400
_shelx_estimated_absorpt_T_max   0.949
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    0.355
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            8357
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.013
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  48.00   0.50    4.42    --   20.00  54.00 -30.00  148
  2  ω     53.00 109.00   0.50    4.42    --   20.00  54.00 -30.00  112
  3  ω    -74.00 108.00   0.50    4.42    --   20.00  54.00-150.00  364
  4  ω    -15.00  11.00   0.50    4.42    --   20.00  54.00 -90.00   52
  5  ω     50.00  75.00   0.50    4.42    --   20.00  54.00 -90.00   50
  6  ω    -25.00   0.00   0.50    4.42    --   20.00  54.00-180.00   50
  7  ω     17.00  42.00   0.50    4.42    --   20.00  54.00-180.00   50
  8  ω     45.00 102.00   0.50    4.42    --   20.00  54.00  30.00  114
  9  ω    -14.00  11.00   0.50    4.42    --   20.00  54.00-120.00   50
 10  ω     40.00  65.00   0.50    4.42    --   20.00  54.00-120.00   50
 11  ω    -66.00 -41.00   0.50    4.42    --   20.00  54.00 -30.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0698483000
_diffrn_orient_matrix_UB_12      -0.0077965000
_diffrn_orient_matrix_UB_13      0.0095543000
_diffrn_orient_matrix_UB_21      -0.0040535000
_diffrn_orient_matrix_UB_22      -0.0478782000
_diffrn_orient_matrix_UB_23      -0.0497092000
_diffrn_orient_matrix_UB_31      0.0046036000
_diffrn_orient_matrix_UB_32      0.0766524000
_diffrn_orient_matrix_UB_33      -0.0300196000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1443
_reflns_number_total             2667
_reflns_odcompleteness_completeness 99.72
_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 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.085
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         2667
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1121
_refine_ls_R_factor_gt           0.0622
_refine_ls_restrained_S_all      1.015
_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)+(0.0969P)²+0.0252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1612
_refine_ls_wR_factor_ref         0.1956
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B)
2.b Idealised Me refined as rotating group:
 C00C(H00C,H00D,H00E), C00D(H00F,H00G,H00H)
;
_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
Cl01 Cl 0.06513(7) 0.52686(10) 0.22021(6) 0.0812(3) Uani 1 1 d . . . . .
O002 O 0.50495(15) 0.2862(2) 0.44660(13) 0.0578(4) Uani 1 1 d . . . . .
N003 N 0.4192(2) 0.2103(3) 0.60075(16) 0.0614(5) Uani 1 1 d . . . . .
N004 N 0.64735(19) 0.1584(3) 0.59306(16) 0.0672(6) Uani 1 1 d . . . . .
C005 C 0.3712(2) 0.3309(3) 0.42686(19) 0.0514(5) Uani 1 1 d . . . . .
C006 C 0.3188(2) 0.2833(3) 0.52091(19) 0.0543(6) Uani 1 1 d . . . . .
C007 C 0.5240(2) 0.2159(3) 0.55201(19) 0.0548(6) Uani 1 1 d . . . . .
C008 C 0.1656(2) 0.4280(3) 0.3347(2) 0.0567(6) Uani 1 1 d . . . . .
C009 C 0.2995(2) 0.4037(3) 0.33149(19) 0.0561(6) Uani 1 1 d . . . . .
H009 H 0.337340 0.433829 0.270606 0.067 Uiso 1 1 calc R U . . .
C00A C 0.1079(2) 0.3807(3) 0.4255(2) 0.0634(6) Uani 1 1 d . . . . .
H00A H 0.017821 0.397460 0.422799 0.076 Uiso 1 1 calc R U . . .
C00B C 0.1835(2) 0.3090(3) 0.5198(2) 0.0662(7) Uani 1 1 d . . . . .
H00B H 0.145307 0.278925 0.580508 0.079 Uiso 1 1 calc R U . . .
C00C C 0.7536(2) 0.1684(4) 0.5279(2) 0.0711(7) Uani 1 1 d . . . . .
H00C H 0.740755 0.081715 0.471451 0.107 Uiso 1 1 calc R U . . .
H00D H 0.837177 0.150956 0.575683 0.107 Uiso 1 1 calc R U . . .
H00E H 0.752590 0.278994 0.493720 0.107 Uiso 1 1 calc R U . . .
C00D C 0.6734(3) 0.0891(4) 0.7063(2) 0.0795(8) Uani 1 1 d . . . . .
H00F H 0.716858 0.174217 0.756350 0.119 Uiso 1 1 calc R U . . .
H00G H 0.729108 -0.009892 0.708527 0.119 Uiso 1 1 calc R U . . .
H00H H 0.591410 0.057554 0.728023 0.119 Uiso 1 1 calc R U . . .


_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
Cl01 C008 1.766(2) . ?
O002 C005 1.397(3) . ?
O002 C007 1.385(3) . ?
N003 C006 1.411(3) . ?
N003 C007 1.320(3) . ?
N004 C007 1.356(3) . ?
N004 C00C 1.464(3) . ?
N004 C00D 1.469(3) . ?
C005 C006 1.404(3) . ?
C005 C009 1.389(3) . ?
C006 C00B 1.404(3) . ?
C008 C009 1.396(3) . ?
C008 C00A 1.399(3) . ?
C009 H009 0.9300 . ?
C00A H00A 0.9300 . ?
C00A C00B 1.390(3) . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9600 . ?
C00C H00D 0.9600 . ?
C00C H00E 0.9600 . ?
C00D H00F 0.9600 . ?
C00D H00G 0.9600 . ?
C00D H00H 0.9600 . ?

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
C007 O002 C005 103.48(16) . . ?
C007 N003 C006 103.21(19) . . ?
C007 N004 C00C 121.3(2) . . ?
C007 N004 C00D 118.4(2) . . ?
C00C N004 C00D 120.3(2) . . ?
O002 C005 C006 107.44(19) . . ?
C009 C005 O002 127.5(2) . . ?
C009 C005 C006 125.1(2) . . ?
C005 C006 N003 109.63(19) . . ?
C00B C006 N003 131.9(2) . . ?
C00B C006 C005 118.5(2) . . ?
N003 C007 O002 116.2(2) . . ?
N003 C007 N004 127.3(2) . . ?
N004 C007 O002 116.5(2) . . ?
C009 C008 Cl01 118.57(19) . . ?
C009 C008 C00A 123.0(2) . . ?
C00A C008 Cl01 118.42(18) . . ?
C005 C009 C008 114.3(2) . . ?
C005 C009 H009 122.8 . . ?
C008 C009 H009 122.8 . . ?
C008 C00A H00A 119.6 . . ?
C00B C00A C008 120.9(2) . . ?
C00B C00A H00A 119.6 . . ?
C006 C00B H00B 120.9 . . ?
C00A C00B C006 118.3(2) . . ?
C00A C00B H00B 120.9 . . ?
N004 C00C H00C 109.5 . . ?
N004 C00C H00D 109.5 . . ?
N004 C00C H00E 109.5 . . ?
H00C C00C H00D 109.5 . . ?
H00C C00C H00E 109.5 . . ?
H00D C00C H00E 109.5 . . ?
N004 C00D H00F 109.5 . . ?
N004 C00D H00G 109.5 . . ?
N004 C00D H00H 109.5 . . ?
H00F C00D H00G 109.5 . . ?
H00F C00D H00H 109.5 . . ?
H00G C00D H00H 109.5 . . ?

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
Cl01 C008 C009 C005 177.75(16) . . . . ?
Cl01 C008 C00A C00B -177.29(19) . . . . ?
O002 C005 C006 N003 0.6(2) . . . . ?
O002 C005 C006 C00B -177.6(2) . . . . ?
O002 C005 C009 C008 177.7(2) . . . . ?
N003 C006 C00B C00A -177.9(2) . . . . ?
C005 O002 C007 N003 0.2(3) . . . . ?
C005 O002 C007 N004 179.3(2) . . . . ?
C005 C006 C00B C00A -0.1(4) . . . . ?
C006 N003 C007 O002 0.2(3) . . . . ?
C006 N003 C007 N004 -178.8(2) . . . . ?
C006 C005 C009 C008 0.0(3) . . . . ?
C007 O002 C005 C006 -0.5(2) . . . . ?
C007 O002 C005 C009 -178.6(2) . . . . ?
C007 N003 C006 C005 -0.5(2) . . . . ?
C007 N003 C006 C00B 177.4(3) . . . . ?
C008 C00A C00B C006 -0.8(4) . . . . ?
C009 C005 C006 N003 178.8(2) . . . . ?
C009 C005 C006 C00B 0.5(4) . . . . ?
C009 C008 C00A C00B 1.4(4) . . . . ?
C00A C008 C009 C005 -0.9(3) . . . . ?
C00C N004 C007 O002 -0.9(3) . . . . ?
C00C N004 C007 N003 178.1(2) . . . . ?
C00D N004 C007 O002 177.6(2) . . . . ?
C00D N004 C007 N003 -3.4(4) . . . . ?

_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 1.665
_oxdiff_exptl_absorpt_empirical_full_min 0.761
