# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc29lrsg
_database_code_depnum_ccdc_archive 'CCDC 2133196'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1002/asia.202200131 2022
loop_
_audit_author_name
_audit_author_address
'Ping-An Wang'
;The Fourth Military Medical University
China
;
_audit_update_record             
;
2022-01-08 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_audit_creation_date             2021-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 Cl N O3'
_chemical_formula_sum            'C12 H12 Cl N O3'
_chemical_formula_weight         253.68
_chemical_absolute_configuration unk
_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 0.0181 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'
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'
Cl Cl 0.3639 0.7018 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.78020(10)
_cell_length_b                   7.48790(10)
_cell_length_c                   27.7844(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1202.55(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3805
_cell_measurement_temperature    230.00(10)
_cell_measurement_theta_max      72.4380
_cell_measurement_theta_min      6.1130
_shelx_estimated_absorpt_T_max   0.787
_shelx_estimated_absorpt_T_min   0.748
_exptl_absorpt_coefficient_mu    2.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86032
_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            colorless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            4506
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        65.931
_diffrn_reflns_theta_max         65.931
_diffrn_reflns_theta_min         6.121
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      230.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -113.00 -51.00   1.00    1.00    --  -40.70 -58.00  40.00   62
  2  ω      1.00  28.00   1.00    1.00    --  -40.70  58.00-178.00   27
  3  ω    -68.00 -17.00   1.00    1.00    --  -40.70  58.00-178.00   51
  4  ω     91.00 117.00   1.00    1.00    --  104.23  58.00-178.00   26
  5  ω     31.00 133.00   1.00    1.00    --  104.23 -58.00  40.00  102
  6  ω    -87.00 -10.00   1.00    1.00    --  -40.70 125.00 -90.00   77
  7  ω     17.00  43.00   1.00    1.00    --   40.70 -58.00  40.00   26
  8  ω     79.00 173.00   1.00    1.00    --  104.23  45.00 120.00   94
  9  ω     31.00 130.00   1.00    1.00    --  104.23 -45.00-180.00   99
 10  ω     72.00 167.00   1.00    1.00    --  104.23  15.00 -60.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0397549000
_diffrn_orient_matrix_UB_12      0.1969852000
_diffrn_orient_matrix_UB_13      0.0137789000
_diffrn_orient_matrix_UB_21      -0.2037771000
_diffrn_orient_matrix_UB_22      0.0097639000
_diffrn_orient_matrix_UB_23      -0.0356363000
_diffrn_orient_matrix_UB_31      -0.1670313000
_diffrn_orient_matrix_UB_32      -0.0587460000
_diffrn_orient_matrix_UB_33      0.0401790000
_diffrn_oxdiff_digest_frames     
;
01156600571559a1b37859f990c3c777b100030f7e1
;
_diffrn_oxdiff_digest_hkl        
;
014260d1841e06ed44ac084874ef41da982709
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2021
_reflns_number_total             2082
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 785 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(6)
_refine_ls_extinction_coef       0.0138(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2082
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0251
_refine_ls_restrained_S_all      1.084
_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)+(0.0350P)²+0.1460P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0661
_refine_ls_wR_factor_ref         0.0669
_refine_special_details          ?
_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
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.33141(13) 0.62583(8) 0.57098(2) 0.0562(2) Uani 1 1 d . . . . .
O1 O 0.3516(3) 0.0270(2) 0.28179(5) 0.0458(4) Uani 1 1 d . . . . .
O2 O 0.9607(3) 0.4584(3) 0.32438(7) 0.0536(5) Uani 1 1 d . . . . .
O3 O 0.7395(3) 0.7026(2) 0.31867(6) 0.0425(4) Uani 1 1 d . . . . .
N1 N 0.5084(3) 0.3037(3) 0.29379(6) 0.0352(4) Uani 1 1 d . . . . .
H1 H 0.5448 0.3255 0.2640 0.042 Uiso 1 1 calc R . . . .
C1 C 0.4005(4) 0.5407(3) 0.51427(8) 0.0376(5) Uani 1 1 d . . . . .
C2 C 0.2412(4) 0.5554(3) 0.47752(8) 0.0396(5) Uani 1 1 d . . . . .
H2 H 0.0994 0.6137 0.4828 0.048 Uiso 1 1 calc R . . . .
C3 C 0.2916(4) 0.4838(3) 0.43308(8) 0.0367(5) Uani 1 1 d . . . . .
H3 H 0.1834 0.4948 0.4080 0.044 Uiso 1 1 calc R . . . .
C4 C 0.4998(3) 0.3956(3) 0.42459(7) 0.0282(4) Uani 1 1 d . . . . .
C5 C 0.6585(4) 0.3857(3) 0.46200(7) 0.0331(5) Uani 1 1 d . . . . .
H5 H 0.8013 0.3288 0.4568 0.040 Uiso 1 1 calc R . . . .
C6 C 0.6101(4) 0.4587(3) 0.50706(8) 0.0385(5) Uani 1 1 d . . . . .
H6 H 0.7192 0.4518 0.5321 0.046 Uiso 1 1 calc R . . . .
C7 C 0.4120(3) 0.1499(3) 0.30809(7) 0.0327(5) Uani 1 1 d . . . . .
C8 C 0.3882(4) 0.1568(3) 0.36218(7) 0.0325(5) Uani 1 1 d . . . . .
H8A H 0.4342 0.0431 0.3768 0.039 Uiso 1 1 calc R . . . .
H8B H 0.2287 0.1841 0.3716 0.039 Uiso 1 1 calc R . . . .
C9 C 0.5526(3) 0.3071(3) 0.37708(7) 0.0290(4) Uani 1 1 d . . . . .
H9 H 0.7101 0.2558 0.3793 0.035 Uiso 1 1 calc R . . . .
C10 C 0.5469(3) 0.4306(3) 0.33243(7) 0.0294(4) Uani 1 1 d . . . . .
H10 H 0.4169 0.5163 0.3346 0.035 Uiso 1 1 calc R . . . .
C11 C 0.7748(4) 0.5285(3) 0.32491(7) 0.0334(5) Uani 1 1 d . . . . .
C12 C 0.9414(5) 0.8065(4) 0.30559(11) 0.0577(7) Uani 1 1 d . . . . .
H12A H 0.9968 0.7685 0.2743 0.087 Uiso 1 1 calc GR . . . .
H12B H 1.0620 0.7886 0.3294 0.087 Uiso 1 1 calc GR . . . .
H12C H 0.9006 0.9321 0.3044 0.087 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
Cl1 C1 1.746(2) . ?
O1 C7 1.226(3) . ?
O2 C11 1.196(3) . ?
O3 C11 1.331(3) . ?
O3 C12 1.449(3) . ?
N1 H1 0.8700 . ?
N1 C7 1.340(3) . ?
N1 C10 1.451(3) . ?
C1 C2 1.380(3) . ?
C1 C6 1.373(3) . ?
C2 H2 0.9400 . ?
C2 C3 1.377(3) . ?
C3 H3 0.9400 . ?
C3 C4 1.393(3) . ?
C4 C5 1.388(3) . ?
C4 C9 1.508(3) . ?
C5 H5 0.9400 . ?
C5 C6 1.394(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.510(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 C9 1.531(3) . ?
C9 H9 0.9900 . ?
C9 C10 1.548(3) . ?
C10 H10 0.9900 . ?
C10 C11 1.522(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?

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
C11 O3 C12 115.80(19) . . ?
C7 N1 H1 123.0 . . ?
C7 N1 C10 114.03(17) . . ?
C10 N1 H1 123.0 . . ?
C2 C1 Cl1 119.09(18) . . ?
C6 C1 Cl1 119.80(17) . . ?
C6 C1 C2 121.1(2) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C9 122.11(18) . . ?
C5 C4 C3 117.99(18) . . ?
C5 C4 C9 119.87(18) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.26(19) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.9(2) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
O1 C7 N1 125.94(19) . . ?
O1 C7 C8 126.36(19) . . ?
N1 C7 C8 107.70(17) . . ?
C7 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
C7 C8 C9 103.75(16) . . ?
H8A C8 H8B 109.0 . . ?
C9 C8 H8A 111.0 . . ?
C9 C8 H8B 111.0 . . ?
C4 C9 C8 115.74(16) . . ?
C4 C9 H9 107.6 . . ?
C4 C9 C10 115.77(16) . . ?
C8 C9 H9 107.6 . . ?
C8 C9 C10 102.09(15) . . ?
C10 C9 H9 107.6 . . ?
N1 C10 C9 101.84(16) . . ?
N1 C10 H10 110.7 . . ?
N1 C10 C11 110.27(17) . . ?
C9 C10 H10 110.7 . . ?
C11 C10 C9 112.29(16) . . ?
C11 C10 H10 110.7 . . ?
O2 C11 O3 124.5(2) . . ?
O2 C11 C10 124.63(19) . . ?
O3 C11 C10 110.90(18) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
Cl1 C1 C2 C3 -178.08(17) . . . . ?
Cl1 C1 C6 C5 177.66(16) . . . . ?
O1 C7 C8 C9 163.3(2) . . . . ?
N1 C7 C8 C9 -17.5(2) . . . . ?
N1 C10 C11 O2 -62.6(3) . . . . ?
N1 C10 C11 O3 117.0(2) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
C2 C3 C4 C5 -1.6(3) . . . . ?
C2 C3 C4 C9 176.4(2) . . . . ?
C3 C4 C5 C6 1.2(3) . . . . ?
C3 C4 C9 C8 -60.8(2) . . . . ?
C3 C4 C9 C10 58.6(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C4 C9 C10 N1 -157.65(16) . . . . ?
C4 C9 C10 C11 84.4(2) . . . . ?
C5 C4 C9 C8 117.2(2) . . . . ?
C5 C4 C9 C10 -123.38(19) . . . . ?
C6 C1 C2 C3 1.1(3) . . . . ?
C7 N1 C10 C9 22.5(2) . . . . ?
C7 N1 C10 C11 141.86(18) . . . . ?
C7 C8 C9 C4 156.30(17) . . . . ?
C7 C8 C9 C10 29.66(19) . . . . ?
C8 C9 C10 N1 -31.03(18) . . . . ?
C8 C9 C10 C11 -148.96(17) . . . . ?
C9 C4 C5 C6 -176.87(19) . . . . ?
C9 C10 C11 O2 50.2(3) . . . . ?
C9 C10 C11 O3 -130.17(18) . . . . ?
C10 N1 C7 O1 175.7(2) . . . . ?
C10 N1 C7 C8 -3.5(2) . . . . ?
C12 O3 C11 O2 6.5(3) . . . . ?
C12 O3 C11 C10 -173.07(18) . . . . ?

_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 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.802
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2222101'
loop_
_audit_author_name
_audit_author_address
'Ping-An Wang'
;The Fourth Military Medical University
China
;
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2023-09-18 downloaded from the CCDC.
;
_audit_creation_date             2021-12-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 Cl N O3'
_chemical_formula_sum            'C12 H12 Cl N O3'
_chemical_formula_weight         253.68
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
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'
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'
Cl Cl 0.3639 0.7018 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.7785(3)
_cell_length_b                   7.4826(3)
_cell_length_c                   27.8645(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1204.81(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1587
_cell_measurement_temperature    240.00(10)
_cell_measurement_theta_max      71.5080
_cell_measurement_theta_min      6.1270
_shelx_estimated_absorpt_T_max   0.749
_shelx_estimated_absorpt_T_min   0.713
_exptl_absorpt_coefficient_mu    2.793
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            3366
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.514
_diffrn_reflns_theta_max         66.514
_diffrn_reflns_theta_min         6.124
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      240.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -109.00 -60.00   1.00    1.50    --  -40.70 -57.00 -90.00   49
  2  ω    -66.00 -22.00   1.00    1.50    --  -40.70 125.00-150.00   44
  3  ω    -53.00  18.00   1.00    1.50    --  -40.70  38.00-150.00   71
  4  ω     78.00 176.00   1.00    1.50    --  104.23  30.00   0.00   98
  5  ω     58.00 112.00   1.00    1.50    --  104.23-125.00 -90.00   54
  6  ω     31.00  97.00   1.00    1.50    --  104.23 -30.00-180.00   66
  7  ω     35.00 128.00   1.00    1.50    --  104.23 -61.00  90.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0098393000
_diffrn_orient_matrix_UB_12      -0.0944341000
_diffrn_orient_matrix_UB_13      -0.0490722000
_diffrn_orient_matrix_UB_21      -0.0124733000
_diffrn_orient_matrix_UB_22      -0.1829033000
_diffrn_orient_matrix_UB_23      0.0252868000
_diffrn_orient_matrix_UB_31      -0.2660993000
_diffrn_orient_matrix_UB_32      0.0050531000
_diffrn_orient_matrix_UB_33      -0.0030385000
_diffrn_oxdiff_digest_frames     
;
01355152ea0cfbc9216873b40b940162a7004979b94
;
_diffrn_oxdiff_digest_hkl        
;
01f0afa80d5a7661176d3b2352e837d26975bb
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                1884
_reflns_number_total             2090
_reflns_odcompleteness_completeness 99.15
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 674 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.029(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2090
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.045
_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)+(0.0377P)²+0.1066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0840
_refine_special_details          ?
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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 0.33476(18) 0.37627(12) 0.57085(3) 0.0618(3) Uani 1 1 d . . . . .
O1 O 0.3528(4) 0.9687(3) 0.28158(8) 0.0507(6) Uani 1 1 d . . . . .
O2 O 0.9625(4) 0.5383(4) 0.32458(10) 0.0591(7) Uani 1 1 d . . . . .
O3 O 0.7407(4) 0.2938(3) 0.31883(8) 0.0470(6) Uani 1 1 d . . . . .
N1 N 0.5097(5) 0.6926(4) 0.29397(9) 0.0392(6) Uani 1 1 d . . . . .
H1 H 0.5454 0.6704 0.2646 0.047 Uiso 1 1 calc R . . . .
C1 C 0.4033(6) 0.4601(4) 0.51414(11) 0.0402(7) Uani 1 1 d . . . . .
C2 C 0.6120(6) 0.5425(4) 0.50674(11) 0.0422(7) Uani 1 1 d . . . . .
H2 H 0.7198 0.5505 0.5314 0.051 Uiso 1 1 calc R . . . .
C3 C 0.6602(5) 0.6139(4) 0.46178(10) 0.0357(7) Uani 1 1 d . . . . .
H3 H 0.8016 0.6700 0.4566 0.043 Uiso 1 1 calc R . . . .
C4 C 0.5024(5) 0.6033(4) 0.42444(10) 0.0312(6) Uani 1 1 d . . . . .
C5 C 0.2942(5) 0.5150(4) 0.43325(11) 0.0396(7) Uani 1 1 d . . . . .
H5 H 0.1868 0.5037 0.4086 0.048 Uiso 1 1 calc R . . . .
C6 C 0.2444(6) 0.4441(4) 0.47761(11) 0.0432(8) Uani 1 1 d . . . . .
H6 H 0.1045 0.3858 0.4829 0.052 Uiso 1 1 calc R . . . .
C7 C 0.5540(5) 0.6907(4) 0.37701(10) 0.0323(6) Uani 1 1 d . . . . .
H7 H 0.7100 0.7416 0.3791 0.039 Uiso 1 1 calc R . . . .
C8 C 0.3904(5) 0.8408(4) 0.36187(10) 0.0361(7) Uani 1 1 d . . . . .
H8A H 0.2324 0.8143 0.3712 0.043 Uiso 1 1 calc R . . . .
H8B H 0.4363 0.9536 0.3761 0.043 Uiso 1 1 calc R . . . .
C9 C 0.4138(5) 0.8466(4) 0.30793(10) 0.0375(7) Uani 1 1 d . . . . .
C10 C 0.5485(5) 0.5660(4) 0.33263(10) 0.0320(6) Uani 1 1 d . . . . .
H10 H 0.4197 0.4813 0.3349 0.038 Uiso 1 1 calc R . . . .
C11 C 0.7756(5) 0.4679(4) 0.32514(11) 0.0365(7) Uani 1 1 d . . . . .
C12 C 0.9433(7) 0.1896(5) 0.30572(15) 0.0630(11) Uani 1 1 d . . . . .
H12A H 1.0046 0.2331 0.2759 0.095 Uiso 1 1 calc GR . . . .
H12B H 0.9005 0.0663 0.3022 0.095 Uiso 1 1 calc GR . . . .
H12C H 1.0586 0.2006 0.3303 0.095 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
Cl1 C1 1.746(3) . ?
O1 C9 1.224(4) . ?
O2 C11 1.202(4) . ?
O3 C11 1.330(4) . ?
O3 C12 1.453(4) . ?
N1 H1 0.8600 . ?
N1 C9 1.337(4) . ?
N1 C10 1.452(4) . ?
C1 C2 1.370(4) . ?
C1 C6 1.376(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(4) . ?
C4 C5 1.395(4) . ?
C4 C7 1.504(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.527(4) . ?
C7 C10 1.550(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.510(4) . ?
C10 H10 0.9800 . ?
C10 C11 1.518(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
C11 O3 C12 115.9(3) . . ?
C9 N1 H1 122.9 . . ?
C9 N1 C10 114.3(2) . . ?
C10 N1 H1 122.9 . . ?
C2 C1 Cl1 119.9(3) . . ?
C2 C1 C6 121.0(3) . . ?
C6 C1 Cl1 119.1(3) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.5(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 117.5(3) . . ?
C3 C4 C7 120.3(3) . . ?
C5 C4 C7 122.1(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.4(3) . . ?
C5 C6 H6 120.3 . . ?
C4 C7 H7 107.4 . . ?
C4 C7 C8 116.1(2) . . ?
C4 C7 C10 115.8(2) . . ?
C8 C7 H7 107.4 . . ?
C8 C7 C10 102.1(2) . . ?
C10 C7 H7 107.4 . . ?
C7 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
C9 C8 C7 103.9(2) . . ?
C9 C8 H8A 111.0 . . ?
C9 C8 H8B 111.0 . . ?
O1 C9 N1 126.0(3) . . ?
O1 C9 C8 126.4(3) . . ?
N1 C9 C8 107.6(2) . . ?
N1 C10 C7 101.7(2) . . ?
N1 C10 H10 110.7 . . ?
N1 C10 C11 110.3(2) . . ?
C7 C10 H10 110.7 . . ?
C11 C10 C7 112.5(2) . . ?
C11 C10 H10 110.7 . . ?
O2 C11 O3 124.4(3) . . ?
O2 C11 C10 124.5(3) . . ?
O3 C11 C10 111.1(3) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_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 1.710
_oxdiff_exptl_absorpt_empirical_full_min 0.626
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
