# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 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_zhaott_1_0222
_database_code_depnum_ccdc_archive 'CCDC 2244895'
loop_
_audit_author_name
_audit_author_address
ztt
;lanzhou univesuty
China
;
_audit_update_record             
;
2023-02-27 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;
_audit_creation_date             2023-02-27
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H21 N O5'
_chemical_formula_sum            'C18 H21 N O5'
_chemical_formula_weight         331.36
_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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.78002(17)
_cell_length_b                   18.6163(6)
_cell_length_c                   15.8540(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.564(3)
_cell_angle_gamma                90
_cell_volume                     1697.89(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5538
_cell_measurement_temperature    300.88(10)
_cell_measurement_theta_max      75.5350
_cell_measurement_theta_min      4.7710
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.878
_exptl_absorpt_coefficient_mu    0.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81581
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_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    1.296
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10981
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.414
_diffrn_reflns_theta_min         3.672
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.88(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_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     63.00  88.00   1.00    0.10    --   45.40 156.00-174.00   25
  2  ω     80.00 150.00   1.00    0.23    --  109.66 156.00-174.00   70
  3  ω     90.00 175.00   1.00    0.23    --  109.66  30.00-150.00   85
  4  ω    -54.00 -28.00   1.00    0.23    -- -100.00  45.00 150.00   26
  5  ω    -71.00 -26.00   1.00    0.23    -- -100.00  61.00  60.00   45
  6  ω    -73.00 -38.00   1.00    0.23    -- -100.00  61.00   0.00   35
  7  ω    -54.00 -26.00   1.00    0.23    -- -100.00  45.00 -90.00   28
  8  ω    -53.00 -25.00   1.00    0.23    -- -100.00  45.00-150.00   28
  9  ω    -51.00 -25.00   1.00    0.23    -- -100.00  45.00-180.00   26
 10  ω    -30.00  38.00   1.00    0.10    --   45.40 -37.00-180.00   68
 11  ω    -29.00  12.00   1.00    0.10    --   45.40 -19.00-150.00   41
 12  ω    -32.00  23.00   1.00    0.10    --   45.40 -19.00 -60.00   55
 13  ω     60.00  85.00   1.00    0.23    --  109.66-156.00 148.00   25
 14  ω     50.00 114.00   1.00    0.10    --   45.40-156.00 148.00   64
 15  ω     30.00  55.00   1.00    0.10    --   45.40-119.00 -55.00   25
 16  ω     69.00 109.00   1.00    0.23    --  109.66-119.00 -55.00   40
 17  ω     62.00 102.00   1.00    0.23    --  109.66 -77.00 -30.00   40
 18  ω     36.00  61.00   1.00    0.23    --  109.66 -61.00 -30.00   25
 19  ω     44.00  99.00   1.00    0.23    --  109.66 -77.00 -60.00   55
 20  ω     42.00  67.00   1.00    0.23    --  109.66 -61.00  90.00   25
 21  ω   -101.00 -63.00   1.00    0.10    --  -45.40-156.00 148.00   38
 22  ω   -154.00-129.00   1.00    0.23    -- -100.00-119.00 -55.00   25
 23  ω   -174.00-137.00   1.00    0.23    -- -100.00 -94.00-180.00   37
 24  ω   -125.00 -87.00   1.00    0.23    -- -100.00 -94.00-180.00   38
 25  ω   -104.00 -78.00   1.00    0.23    -- -100.00 119.00  29.00   26
 26  ω   -101.00 -76.00   1.00    0.10    --  -45.40 156.00-174.00   25
 27  ω    -79.00 -40.00   1.00    0.23    -- -100.00 156.00-174.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0229391000
_diffrn_orient_matrix_UB_12      0.0800260000
_diffrn_orient_matrix_UB_13      0.0241308000
_diffrn_orient_matrix_UB_21      -0.0506538000
_diffrn_orient_matrix_UB_22      -0.0182440000
_diffrn_orient_matrix_UB_23      0.0911918000
_diffrn_orient_matrix_UB_31      0.2619384000
_diffrn_orient_matrix_UB_32      -0.0105592000
_diffrn_orient_matrix_UB_33      0.0251858000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2667
_reflns_number_total             3377
_reflns_odcompleteness_completeness 100.00
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_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         0.184
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0038(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.082
_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)+(0.0533P)²+0.2084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1268
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(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)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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
O1 O 0.1393(2) 0.82940(7) 0.63894(8) 0.0569(3) Uani 1 1 d . . . . .
O2 O 0.4412(2) 0.91091(6) 0.56403(8) 0.0570(3) Uani 1 1 d . . . . .
O3 O 0.7041(2) 0.85610(6) 0.45082(9) 0.0606(4) Uani 1 1 d . . . . .
O4 O 0.18834(19) 0.64135(7) 0.35175(8) 0.0547(3) Uani 1 1 d . . . . .
O5 O -0.0109(2) 0.57247(7) 0.43364(8) 0.0641(4) Uani 1 1 d . . . . .
N1 N 0.3383(2) 0.56759(7) 0.55702(9) 0.0483(3) Uani 1 1 d . . . . .
H1 H 0.209239 0.544527 0.556522 0.058 Uiso 1 1 calc R . . . .
C1 C 0.3954(2) 0.69301(7) 0.50901(9) 0.0377(3) Uani 1 1 d . . . . .
C2 C 0.2549(2) 0.72221(8) 0.56561(10) 0.0416(3) Uani 1 1 d . . . . .
H2 H 0.152264 0.693147 0.591798 0.050 Uiso 1 1 calc R . . . .
C3 C 0.2675(2) 0.79533(8) 0.58334(10) 0.0428(4) Uani 1 1 d . . . . .
C4 C 0.4198(3) 0.83919(8) 0.54388(10) 0.0433(4) Uani 1 1 d . . . . .
C5 C 0.5597(3) 0.80924(8) 0.48643(10) 0.0436(4) Uani 1 1 d . . . . .
C6 C 0.5487(3) 0.73590(8) 0.46918(10) 0.0418(3) Uani 1 1 d . . . . .
H6 H 0.643290 0.715775 0.431248 0.050 Uiso 1 1 calc R . . . .
C7 C 0.3725(2) 0.61320(7) 0.48619(10) 0.0394(3) Uani 1 1 d . . . . .
H7 H 0.511885 0.597630 0.460661 0.047 Uiso 1 1 calc R . . . .
C8 C 0.1618(3) 0.60499(8) 0.42159(10) 0.0411(3) Uani 1 1 d . . . . .
C9 C -0.0062(3) 0.64300(11) 0.28792(12) 0.0583(5) Uani 1 1 d . . . . .
H9A H 0.001774 0.602497 0.250835 0.087 Uiso 1 1 calc GR . . . .
H9B H -0.001984 0.686589 0.255747 0.087 Uiso 1 1 calc GR . . . .
H9C H -0.148298 0.641017 0.314570 0.087 Uiso 1 1 calc GR . . . .
C10 C 0.5016(3) 0.55876(7) 0.62594(10) 0.0411(3) Uani 1 1 d . . . . .
C11 C 0.4491(3) 0.51462(9) 0.69270(12) 0.0512(4) Uani 1 1 d . . . . .
H11 H 0.306897 0.490911 0.689471 0.061 Uiso 1 1 calc R . . . .
C12 C 0.6045(3) 0.50578(11) 0.76300(12) 0.0613(5) Uani 1 1 d . . . . .
H12 H 0.566514 0.475961 0.806652 0.074 Uiso 1 1 calc R . . . .
C13 C 0.8166(3) 0.54050(12) 0.76986(13) 0.0644(5) Uani 1 1 d . . . . .
H13 H 0.920334 0.535057 0.818053 0.077 Uiso 1 1 calc R . . . .
C14 C 0.8710(3) 0.58321(11) 0.70407(13) 0.0619(5) Uani 1 1 d . . . . .
H14 H 1.014348 0.606281 0.707697 0.074 Uiso 1 1 calc R . . . .
C15 C 0.7175(3) 0.59267(9) 0.63257(12) 0.0517(4) Uani 1 1 d . . . . .
H15 H 0.758450 0.621764 0.588699 0.062 Uiso 1 1 calc R . . . .
C16 C -0.0241(3) 0.78849(13) 0.67930(14) 0.0719(6) Uani 1 1 d . . . . .
H16A H -0.138897 0.769440 0.637428 0.108 Uiso 1 1 calc GR . . . .
H16B H -0.098374 0.818565 0.717816 0.108 Uiso 1 1 calc GR . . . .
H16C H 0.054135 0.749679 0.710077 0.108 Uiso 1 1 calc GR . . . .
C17 C 0.2528(3) 0.95409(9) 0.52726(14) 0.0633(5) Uani 1 1 d . . . . .
H17A H 0.247578 0.951937 0.466608 0.095 Uiso 1 1 calc GR . . . .
H17B H 0.275309 1.002948 0.545616 0.095 Uiso 1 1 calc GR . . . .
H17C H 0.109168 0.936344 0.544902 0.095 Uiso 1 1 calc GR . . . .
C18 C 0.8423(4) 0.82915(11) 0.38885(13) 0.0657(5) Uani 1 1 d . . . . .
H18A H 0.743834 0.807359 0.343708 0.099 Uiso 1 1 calc GR . . . .
H18B H 0.948818 0.793969 0.414182 0.099 Uiso 1 1 calc GR . . . .
H18C H 0.927836 0.867874 0.366658 0.099 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
O1 C3 1.3619(19) . ?
O1 C16 1.413(2) . ?
O2 C4 1.3757(17) . ?
O2 C17 1.431(2) . ?
O3 C5 1.3666(18) . ?
O3 C18 1.417(2) . ?
O4 C8 1.3195(19) . ?
O4 C9 1.438(2) . ?
O5 C8 1.1985(18) . ?
N1 C7 1.4367(19) . ?
N1 C10 1.383(2) . ?
C1 C2 1.379(2) . ?
C1 C6 1.389(2) . ?
C1 C7 1.5317(19) . ?
C2 C3 1.390(2) . ?
C3 C4 1.393(2) . ?
C4 C5 1.392(2) . ?
C5 C6 1.393(2) . ?
C7 C8 1.521(2) . ?
C10 C11 1.396(2) . ?
C10 C15 1.394(2) . ?
C11 C12 1.372(3) . ?
C12 C13 1.381(3) . ?
C13 C14 1.372(3) . ?
C14 C15 1.381(3) . ?

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
C3 O1 C16 118.11(14) . . ?
C4 O2 C17 113.77(13) . . ?
C5 O3 C18 117.93(13) . . ?
C8 O4 C9 117.06(13) . . ?
C10 N1 C7 123.56(12) . . ?
C2 C1 C6 120.72(13) . . ?
C2 C1 C7 119.56(12) . . ?
C6 C1 C7 119.63(13) . . ?
C1 C2 C3 119.68(13) . . ?
O1 C3 C2 124.46(14) . . ?
O1 C3 C4 115.15(14) . . ?
C2 C3 C4 120.39(14) . . ?
O2 C4 C3 120.73(14) . . ?
O2 C4 C5 119.74(14) . . ?
C5 C4 C3 119.46(13) . . ?
O3 C5 C4 115.56(13) . . ?
O3 C5 C6 124.25(14) . . ?
C4 C5 C6 120.19(13) . . ?
C1 C6 C5 119.56(14) . . ?
N1 C7 C1 113.83(13) . . ?
N1 C7 C8 107.76(12) . . ?
C8 C7 C1 107.56(11) . . ?
O4 C8 C7 111.28(12) . . ?
O5 C8 O4 124.00(15) . . ?
O5 C8 C7 124.64(14) . . ?
N1 C10 C11 119.15(14) . . ?
N1 C10 C15 122.93(14) . . ?
C15 C10 C11 117.92(15) . . ?
C12 C11 C10 120.87(16) . . ?
C11 C12 C13 120.95(18) . . ?
C14 C13 C12 118.60(17) . . ?
C13 C14 C15 121.42(17) . . ?
C14 C15 C10 120.23(16) . . ?

_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 1.985
_oxdiff_exptl_absorpt_empirical_full_min 0.495
####################################################################### 
# 
# 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_zhaott_2_0224_autored
_database_code_depnum_ccdc_archive 'CCDC 2244897'
loop_
_audit_author_name
_audit_author_address
ztt
;lanzhou univesuty
China
;
_audit_update_record             
;
2023-02-27 deposited with the CCDC.	2023-10-10 downloaded from the CCDC.
;
_audit_creation_date             2023-02-24
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 Cl N O2'
_chemical_formula_sum            'C21 H18 Cl N O2'
_chemical_formula_weight         351.81
_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'
Cl Cl 0.3639 0.7018 '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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.4508(2)
_cell_length_b                   12.4654(2)
_cell_length_c                   14.1577(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.135(2)
_cell_angle_gamma                90
_cell_volume                     1820.98(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7897
_cell_measurement_temperature    300.88(10)
_cell_measurement_theta_max      76.3080
_cell_measurement_theta_min      3.1150
_shelx_estimated_absorpt_T_max   0.875
_shelx_estimated_absorpt_T_min   0.771
_exptl_absorpt_coefficient_mu    1.960
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.113a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_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    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12011
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.528
_diffrn_reflns_theta_min         4.753
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300.88(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.940
_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  13.00   1.00    0.10    --  -45.27  72.00 135.00   62
  2  ω    -51.00 -25.00   1.00    0.17    -- -100.00  45.00 150.00   26
  3  ω    -54.00 -29.00   1.00    0.17    -- -100.00  45.00 120.00   25
  4  ω    -94.00 -37.00   1.00    0.17    -- -100.00  72.00 135.00   57
  5  ω    -54.00 -25.00   1.00    0.17    -- -100.00  45.00   0.00   29
  6  ω    -52.00 -26.00   1.00    0.17    -- -100.00  45.00 -60.00   26
  7  ω    -54.00 -26.00   1.00    0.17    -- -100.00  45.00 -90.00   28
  8  ω    -73.00 -27.00   1.00    0.17    -- -100.00  61.00-150.00   46
  9  ω   -118.00 -22.00   1.00    0.10    --  -45.27 -72.00   5.00   96
 10  ω     45.00  70.00   1.00    0.10    --   45.27  72.00 135.00   25
 11  ω     88.00 173.00   1.00    0.17    --  109.66  72.00 135.00   85
 12  ω    132.00 174.00   1.00    0.17    --  109.66  15.00  90.00   42
 13  ω    104.00 173.00   1.00    0.17    --  109.66  45.00  60.00   69
 14  ω     78.00 123.00   1.00    0.17    --  109.66  15.00  90.00   45
 15  ω     42.00  84.00   1.00    0.17    --  109.66 -72.00   5.00   42
 16  ω     42.00  67.00   1.00    0.17    --  109.66 -61.00  30.00   25
 17  ω     37.00  62.00   1.00    0.17    --  109.66 -61.00  60.00   25
 18  ω     36.00  61.00   1.00    0.17    --  109.66 -61.00 150.00   25
 19  ω    -11.00  22.00   1.00    0.10    --   45.27 -72.00   5.00   33
 20  ω    -23.00  23.00   1.00    0.10    --   45.27 -19.00   0.00   46
 21  ω     36.00  67.00   1.00    0.17    --  109.66 -61.00 -90.00   31
 22  ω     44.00  95.00   1.00    0.17    --  109.66 -77.00 -90.00   51
 23  ω     83.00 108.00   1.00    0.17    --  109.66-125.00 -90.00   25
 24  ω     38.00  66.00   1.00    0.17    --  109.66 -61.00 -60.00   28
 25  ω     37.00  69.00   1.00    0.17    --  109.66-125.00 -90.00   32
 26  ω    -30.00   9.00   1.00    0.10    --   45.27 -19.00-150.00   39
 27  ω   -164.00-139.00   1.00    0.17    -- -100.00 -72.00   5.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0555580000
_diffrn_orient_matrix_UB_12      -0.0196272000
_diffrn_orient_matrix_UB_13      -0.0931131000
_diffrn_orient_matrix_UB_21      -0.0790848000
_diffrn_orient_matrix_UB_22      -0.1045977000
_diffrn_orient_matrix_UB_23      -0.0165686000
_diffrn_orient_matrix_UB_31      -0.1136745000
_diffrn_orient_matrix_UB_32      0.0628210000
_diffrn_orient_matrix_UB_33      -0.0566687000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3253
_reflns_number_total             3599
_reflns_odcompleteness_completeness 97.79
_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 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.113a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.113a (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       0.0066(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3599
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.060
_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)+(0.0457P)²+0.4251P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1009
_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:
 C2(H2), C3(H3), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11), C12(H12),
 C13(H13), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.75017(6) 0.94594(5) 0.20882(4) 0.0908(2) Uani 1 1 d . . . . .
O1 O 0.14081(9) 0.51733(8) 0.41427(7) 0.0491(3) Uani 1 1 d . . . . .
O2 O 0.34423(10) 0.48970(9) 0.48296(9) 0.0601(3) Uani 1 1 d . . . . .
N1 N 0.43343(10) 0.66711(9) 0.41809(8) 0.0394(3) Uani 1 1 d . . . . .
H1 H 0.4721(16) 0.6056(14) 0.4345(12) 0.051(4) Uiso 1 1 d . . . . .
C1 C 0.50478(12) 0.73441(10) 0.36746(8) 0.0364(3) Uani 1 1 d . . . . .
C2 C 0.46213(14) 0.83630(11) 0.33645(10) 0.0466(3) Uani 1 1 d . . . . .
H2 H 0.381827 0.860663 0.347758 0.056 Uiso 1 1 calc R . . . .
C3 C 0.53819(16) 0.90150(12) 0.28899(11) 0.0546(4) Uani 1 1 d . . . . .
H3 H 0.509149 0.969423 0.268537 0.065 Uiso 1 1 calc R . . . .
C4 C 0.65630(16) 0.86571(13) 0.27224(11) 0.0544(4) Uani 1 1 d . . . . .
C5 C 0.70165(15) 0.76606(13) 0.30292(11) 0.0547(4) Uani 1 1 d . . . . .
H5 H 0.782525 0.742781 0.291888 0.066 Uiso 1 1 calc R . . . .
C6 C 0.62581(14) 0.70099(11) 0.35028(10) 0.0456(3) Uani 1 1 d . . . . .
H6 H 0.656268 0.633549 0.371069 0.055 Uiso 1 1 calc R . . . .
C7 C 0.29270(12) 0.65501(9) 0.39480(9) 0.0367(3) Uani 1 1 d . . . . .
C8 C 0.25131(12) 0.64960(10) 0.28554(9) 0.0401(3) Uani 1 1 d . . . . .
C9 C 0.29598(16) 0.56358(12) 0.23748(11) 0.0513(3) Uani 1 1 d . . . . .
H9 H 0.345645 0.510808 0.272386 0.062 Uiso 1 1 calc R . . . .
C10 C 0.26842(19) 0.55462(15) 0.13923(12) 0.0648(5) Uani 1 1 d . . . . .
H10 H 0.298766 0.495954 0.108767 0.078 Uiso 1 1 calc R . . . .
C11 C 0.1963(2) 0.63214(18) 0.08639(12) 0.0724(5) Uani 1 1 d . . . . .
H11 H 0.176682 0.625940 0.020213 0.087 Uiso 1 1 calc R . . . .
C12 C 0.15332(18) 0.71899(17) 0.13219(13) 0.0699(5) Uani 1 1 d . . . . .
H12 H 0.105641 0.772262 0.096489 0.084 Uiso 1 1 calc R . . . .
C13 C 0.18023(15) 0.72833(13) 0.23145(11) 0.0530(4) Uani 1 1 d . . . . .
H13 H 0.150417 0.787557 0.261479 0.064 Uiso 1 1 calc R . . . .
C14 C 0.26406(13) 0.54442(10) 0.43642(9) 0.0392(3) Uani 1 1 d . . . . .
C15 C 0.10455(16) 0.41428(12) 0.44957(12) 0.0554(4) Uani 1 1 d . . . . .
H15A H 0.149818 0.358190 0.422161 0.083 Uiso 1 1 calc GR . . . .
H15B H 0.012829 0.403996 0.431926 0.083 Uiso 1 1 calc GR . . . .
H15C H 0.126997 0.412451 0.517985 0.083 Uiso 1 1 calc GR . . . .
C16 C 0.22109(13) 0.73828(10) 0.44784(9) 0.0413(3) Uani 1 1 d . . . . .
C17 C 0.29000(16) 0.79866(12) 0.52096(10) 0.0536(4) Uani 1 1 d . . . . .
H17 H 0.379652 0.792002 0.534788 0.064 Uiso 1 1 calc R . . . .
C18 C 0.2264(2) 0.86903(15) 0.57377(13) 0.0685(5) Uani 1 1 d . . . . .
H18 H 0.273900 0.909176 0.622546 0.082 Uiso 1 1 calc R . . . .
C19 C 0.0943(2) 0.87990(15) 0.55473(15) 0.0731(5) Uani 1 1 d . . . . .
H19 H 0.052113 0.926772 0.590599 0.088 Uiso 1 1 calc R . . . .
C20 C 0.02476(18) 0.82081(14) 0.48204(15) 0.0683(5) Uani 1 1 d . . . . .
H20 H -0.064780 0.828445 0.468241 0.082 Uiso 1 1 calc R . . . .
C21 C 0.08716(15) 0.75014(12) 0.42935(13) 0.0540(4) Uani 1 1 d . . . . .
H21 H 0.038911 0.710013 0.380917 0.065 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 C4 1.7460(15) . ?
O1 C14 1.3203(16) . ?
O1 C15 1.4504(16) . ?
O2 C14 1.1942(16) . ?
N1 C1 1.3941(16) . ?
N1 C7 1.4630(16) . ?
C1 C2 1.3937(18) . ?
C1 C6 1.3893(19) . ?
C2 C3 1.383(2) . ?
C3 C4 1.368(2) . ?
C4 C5 1.375(2) . ?
C5 C6 1.380(2) . ?
C7 C8 1.5402(18) . ?
C7 C14 1.5470(16) . ?
C7 C16 1.5427(18) . ?
C8 C9 1.390(2) . ?
C8 C13 1.3859(19) . ?
C9 C10 1.380(2) . ?
C10 C11 1.372(3) . ?
C11 C12 1.373(3) . ?
C12 C13 1.394(2) . ?
C16 C17 1.386(2) . ?
C16 C21 1.390(2) . ?
C17 C18 1.388(2) . ?
C18 C19 1.371(3) . ?
C19 C20 1.376(3) . ?
C20 C21 1.383(2) . ?

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
C14 O1 C15 116.30(11) . . ?
C1 N1 C7 123.15(10) . . ?
C2 C1 N1 122.68(12) . . ?
C6 C1 N1 119.06(11) . . ?
C6 C1 C2 118.21(12) . . ?
C3 C2 C1 120.58(14) . . ?
C4 C3 C2 119.76(14) . . ?
C3 C4 Cl1 119.89(12) . . ?
C3 C4 C5 121.00(13) . . ?
C5 C4 Cl1 119.09(13) . . ?
C4 C5 C6 119.25(14) . . ?
C5 C6 C1 121.19(13) . . ?
N1 C7 C8 110.05(10) . . ?
N1 C7 C14 104.74(9) . . ?
N1 C7 C16 111.65(10) . . ?
C8 C7 C14 107.64(10) . . ?
C8 C7 C16 115.96(10) . . ?
C16 C7 C14 106.02(10) . . ?
C9 C8 C7 117.57(12) . . ?
C13 C8 C7 124.36(13) . . ?
C13 C8 C9 117.91(13) . . ?
C10 C9 C8 121.57(15) . . ?
C11 C10 C9 120.10(18) . . ?
C10 C11 C12 119.35(16) . . ?
C11 C12 C13 120.88(16) . . ?
C8 C13 C12 120.17(16) . . ?
O1 C14 C7 112.20(10) . . ?
O2 C14 O1 123.89(12) . . ?
O2 C14 C7 123.91(12) . . ?
C17 C16 C7 119.63(12) . . ?
C17 C16 C21 118.11(13) . . ?
C21 C16 C7 122.11(13) . . ?
C16 C17 C18 120.60(16) . . ?
C19 C18 C17 120.65(17) . . ?
C18 C19 C20 119.36(16) . . ?
C19 C20 C21 120.41(16) . . ?
C20 C21 C16 120.87(16) . . ?

_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 1.555
_oxdiff_exptl_absorpt_empirical_full_min 0.687
