# Supplementary Information (SI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_2_211_1
_database_code_depnum_ccdc_archive 'CCDC 2335728'
loop_
_audit_author_name
_audit_author_address
'zurong Xu'
;South China University of Technology 
China
;
_audit_update_record             
;
2024-02-27 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;
_audit_creation_date             2023-04-01
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 Br O3'
_chemical_formula_sum            'C14 H13 Br O3'
_chemical_formula_weight         309.15
_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'
Br Br -0.6763 1.2805 '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/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                   6.5459(6)
_cell_length_b                   7.4134(4)
_cell_length_c                   27.118(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.115(9)
_cell_angle_gamma                90
_cell_volume                     1308.48(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2753
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      70.9200
_cell_measurement_theta_min      3.2270
_shelx_estimated_absorpt_T_max   0.726
_shelx_estimated_absorpt_T_min   0.607
_exptl_absorpt_coefficient_mu    4.273
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48611
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.1447
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -3
_diffrn_reflns_number            2308
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.568
_diffrn_reflns_theta_max         66.568
_diffrn_reflns_theta_min         3.278
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00  -8.00   1.00    1.00    --  -40.92 -77.00   0.00  109
  2  ω   -115.00 -17.00   1.00    1.00    --  -40.92 -37.00-150.00   98
  3  ω     23.00  97.00   1.00    1.00    --   40.92-125.00  30.00   74
  4  ω     17.00  92.00   1.00    1.00    --   40.92-117.00-150.00   75
  5  ω     17.00 115.00   1.00    1.00    --   40.92  37.00 120.00   98
  6  ω     81.00 178.00   1.00    1.50    --  106.95  45.00 -90.00   97
  7  ω     34.00 121.00   1.00    1.50    --  106.95-125.00 150.00   87
  8  ω     32.00  74.00   1.00    1.50    --  106.95 -15.00-150.00   42
  9  ω     42.00  86.00   1.00    1.50    --  106.95 -30.00 -60.00   44
 10  ω    100.00 135.00   1.00    1.50    --  106.95 -30.00 120.00   35
 11  ω    106.00 134.00   1.00    1.50    --  106.95 -30.00 -60.00   28
 12  ω    126.00 178.00   1.00    1.50    --  106.95 125.00  30.00   52
 13  ω     32.00  95.00   1.00    1.50    --  106.95 -30.00 120.00   63
 14  ω     81.00 149.00   1.00    1.50    --  106.95  45.00 120.00   68
 15  ω     87.00 144.00   1.00    1.50    --  106.95 -15.00-150.00   57
 16  ω     35.00 136.00   1.00    1.50    --  106.95 -61.00 120.00  101
 17  ω     82.00 109.00   1.00    1.50    --  106.95 -94.00 -60.00   27
 18  ω     32.00 140.00   1.00    1.50    --  106.95 -77.00 -60.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0742923000
_diffrn_orient_matrix_UB_12      0.0579478000
_diffrn_orient_matrix_UB_13      0.0535210000
_diffrn_orient_matrix_UB_21      0.0124809000
_diffrn_orient_matrix_UB_22      0.1972671000
_diffrn_orient_matrix_UB_23      -0.0172792000
_diffrn_orient_matrix_UB_31      -0.2242336000
_diffrn_orient_matrix_UB_32      0.0301412000
_diffrn_orient_matrix_UB_33      0.0102624000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1980
_reflns_number_total             2308
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         3.426
_refine_diff_density_min         -1.543
_refine_diff_density_rms         0.439
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.595
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1251
_refine_ls_R_factor_gt           0.1137
_refine_ls_restrained_S_all      2.595
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3452
_refine_ls_wR_factor_ref         0.3523
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.712(7)
 0.288(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C11(H11)
3.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Br1 Br 0.8435(2) 0.19899(15) 0.54635(4) 0.0615(4) Uani 1 1 d . . . A 1
O1 O 0.1860(11) 0.5075(8) 0.2032(2) 0.0422(16) Uani 1 1 d . . . . .
O2 O 0.1769(15) 0.2269(11) 0.1726(3) 0.062(2) Uani 1 1 d . . . . .
O3 O -0.2383(12) 0.4290(10) 0.1929(3) 0.053(2) Uani 1 1 d . . . . .
C1 C 0.4399(15) 0.4016(12) 0.4049(3) 0.042(2) Uani 1 1 d . . . . .
C2 C 0.6508(15) 0.4526(14) 0.4138(4) 0.046(2) Uani 1 1 d . . . . .
H2 H 0.710064 0.527383 0.390652 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7662(16) 0.3951(12) 0.4549(3) 0.044(2) Uani 1 1 d . . . . .
H3 H 0.906332 0.429443 0.461187 0.053 Uiso 1 1 calc R U . . .
C4 C 0.6754(16) 0.2832(11) 0.4882(4) 0.043(2) Uani 1 1 d . . . . .
C5 C 0.4760(15) 0.2371(11) 0.4810(3) 0.039(2) Uani 1 1 d . . . . .
H5 H 0.418572 0.165640 0.505138 0.046 Uiso 1 1 calc R U . . .
C6 C 0.354(2) 0.2911(13) 0.4395(4) 0.051(3) Uani 1 1 d . . . . .
H6 H 0.214420 0.254737 0.434214 0.061 Uiso 1 1 calc R U . . .
C7 C 0.3141(19) 0.4750(10) 0.3604(3) 0.049(3) Uani 1 1 d . . . . .
H7 H 0.274446 0.603039 0.365994 0.059 Uiso 1 1 calc R U . . .
C8 C 0.3986(17) 0.4530(14) 0.3081(4) 0.047(3) Uani 1 1 d . . . . .
H8A H 0.456620 0.565144 0.295475 0.057 Uiso 1 1 calc R U . . .
H8B H 0.494319 0.350349 0.306292 0.057 Uiso 1 1 calc R U . . .
C9 C 0.1887(16) 0.4148(11) 0.2868(3) 0.042(2) Uani 1 1 d . . . . .
C10 C 0.1266(16) 0.3652(13) 0.3361(4) 0.047(2) Uani 1 1 d . . . . .
H10A H 0.134756 0.234275 0.343194 0.056 Uiso 1 1 calc R U . . .
H10B H -0.008157 0.414943 0.342655 0.056 Uiso 1 1 calc R U . . .
C11 C -0.1340(15) 0.4089(11) 0.2340(4) 0.040(2) Uani 1 1 d . . . . .
H11 H -0.203426 0.373370 0.261480 0.049 Uiso 1 1 calc R U . . .
C12 C 0.0769(15) 0.4354(13) 0.2419(3) 0.042(2) Uani 1 1 d . . . . .
C13 C 0.2157(15) 0.3818(11) 0.1681(3) 0.040(2) Uani 1 1 d . . . . .
C14 C 0.3118(15) 0.4677(13) 0.1253(3) 0.044(2) Uani 1 1 d . . . . .
H14A H 0.254609 0.588686 0.119082 0.066 Uiso 1 1 calc R U . . .
H14B H 0.282101 0.393454 0.095488 0.066 Uiso 1 1 calc R U . . .
H14C H 0.460887 0.476241 0.133687 0.066 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
Br1 C4 1.927(10) . ?
O1 C12 1.434(12) . ?
O1 C13 1.361(11) . ?
O2 C13 1.185(12) . ?
O3 C11 1.254(12) . ?
C1 C2 1.427(14) . ?
C1 C6 1.408(15) . ?
C1 C7 1.489(13) . ?
C2 H2 0.9500 . ?
C2 C3 1.347(13) . ?
C3 H3 0.9500 . ?
C3 C4 1.405(14) . ?
C4 C5 1.343(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.367(14) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C7 C8 1.586(14) . ?
C7 C10 1.560(14) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.460(14) . ?
C9 C10 1.483(14) . ?
C9 C12 1.361(13) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11 0.9500 . ?
C11 C12 1.388(14) . ?
C13 C14 1.518(13) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
C13 O1 C12 112.1(7) . . ?
C2 C1 C7 118.8(9) . . ?
C6 C1 C2 119.3(9) . . ?
C6 C1 C7 121.9(10) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(9) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.8(10) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 Br1 118.3(8) . . ?
C5 C4 Br1 119.9(7) . . ?
C5 C4 C3 121.8(9) . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.2(10) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 H6 120.6 . . ?
C5 C6 C1 118.7(11) . . ?
C5 C6 H6 120.6 . . ?
C1 C7 H7 110.7 . . ?
C1 C7 C8 118.2(9) . . ?
C1 C7 C10 119.7(8) . . ?
C8 C7 H7 110.7 . . ?
C10 C7 H7 110.7 . . ?
C10 C7 C8 84.3(7) . . ?
C7 C8 H8A 113.9 . . ?
C7 C8 H8B 113.9 . . ?
H8A C8 H8B 111.1 . . ?
C9 C8 C7 88.3(8) . . ?
C9 C8 H8A 113.9 . . ?
C9 C8 H8B 113.9 . . ?
C8 C9 C10 91.6(8) . . ?
C12 C9 C8 136.5(10) . . ?
C12 C9 C10 131.4(10) . . ?
C7 C10 H10A 113.9 . . ?
C7 C10 H10B 113.9 . . ?
C9 C10 C7 88.5(8) . . ?
C9 C10 H10A 113.9 . . ?
C9 C10 H10B 113.9 . . ?
H10A C10 H10B 111.1 . . ?
O3 C11 H11 118.0 . . ?
O3 C11 C12 124.0(9) . . ?
C12 C11 H11 118.0 . . ?
C9 C12 O1 115.8(9) . . ?
C9 C12 C11 123.6(9) . . ?
C11 C12 O1 120.3(8) . . ?
O1 C13 C14 110.5(7) . . ?
O2 C13 O1 122.9(9) . . ?
O2 C13 C14 126.6(9) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
Br1 C4 C5 C6 -178.4(7) . . . . ?
O3 C11 C12 O1 6.7(14) . . . . ?
O3 C11 C12 C9 179.4(9) . . . . ?
C1 C2 C3 C4 0.6(15) . . . . ?
C1 C7 C8 C9 140.4(8) . . . . ?
C1 C7 C10 C9 -138.7(9) . . . . ?
C2 C1 C6 C5 0.5(14) . . . . ?
C2 C1 C7 C8 52.3(11) . . . . ?
C2 C1 C7 C10 152.4(10) . . . . ?
C2 C3 C4 Br1 179.1(7) . . . . ?
C2 C3 C4 C5 -2.1(14) . . . . ?
C3 C4 C5 C6 2.8(14) . . . . ?
C4 C5 C6 C1 -2.0(15) . . . . ?
C6 C1 C2 C3 0.1(15) . . . . ?
C6 C1 C7 C8 -130.9(10) . . . . ?
C6 C1 C7 C10 -30.8(14) . . . . ?
C7 C1 C2 C3 177.0(9) . . . . ?
C7 C1 C6 C5 -176.3(9) . . . . ?
C7 C8 C9 C10 -20.7(7) . . . . ?
C7 C8 C9 C12 151.7(11) . . . . ?
C8 C7 C10 C9 -19.4(7) . . . . ?
C8 C9 C10 C7 21.0(7) . . . . ?
C8 C9 C12 O1 2.5(16) . . . . ?
C8 C9 C12 C11 -170.5(10) . . . . ?
C10 C7 C8 C9 19.7(7) . . . . ?
C10 C9 C12 O1 172.3(9) . . . . ?
C10 C9 C12 C11 -0.7(16) . . . . ?
C12 O1 C13 O2 -8.4(13) . . . . ?
C12 O1 C13 C14 174.2(7) . . . . ?
C12 C9 C10 C7 -152.0(10) . . . . ?
C13 O1 C12 C9 109.8(9) . . . . ?
C13 O1 C12 C11 -77.0(10) . . . . ?

_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 1.662
_oxdiff_exptl_absorpt_empirical_full_min 0.683
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.712(7)
2 0.288(7)

####################################################################### 
# 
# 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_179-4
_database_code_depnum_ccdc_archive 'CCDC 2335731'
loop_
_audit_author_name
_audit_author_address
'zurong Xu'
;South China University of Technology 
China
;
_audit_update_record             
;
2024-02-27 deposited with the CCDC.	2024-11-18 downloaded from the CCDC.
;
_audit_creation_date             2021-11-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 O5'
_chemical_formula_sum            'C16 H14 O5'
_chemical_formula_weight         286.27
_chemical_absolute_configuration ?
_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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.7856(4)
_cell_length_b                   6.0442(4)
_cell_length_c                   16.6292(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.683(5)
_cell_angle_gamma                90
_cell_volume                     681.27(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2083
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.3590
_cell_measurement_theta_min      5.3060
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.871
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77547
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.14
_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  0.0449
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2502
_diffrn_reflns_point_group_measured_fraction_full 0.727
_diffrn_reflns_point_group_measured_fraction_max 0.688
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.435
_diffrn_reflns_theta_min         2.660
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  61.00   1.00    1.00    --   40.73 -57.00   0.00   63
  2  ω     31.00 134.00   1.00    1.00    --  106.95 -30.00 -90.00  103
  3  ω     93.00 119.00   1.00    1.00    --  106.95-125.00-180.00   26
  4  ω     54.00  80.00   1.00    1.00    --  106.95-125.00-180.00   26
  5  ω     26.00 101.00   1.00    1.00    --  106.95 -95.00  90.00   75
  6  ω     86.00 111.00   1.00    1.00    --  106.95  45.00  90.00   25
  7  ω    132.00 164.00   1.00    1.00    --  106.95  45.00  90.00   32
  8  ω    115.00 177.00   1.00    1.00    --  106.95 125.00  60.00   62
  9  ω     94.00 170.00   1.00    1.00    --  106.95 125.00   0.00   76
 10  ω    -34.00   3.00   1.00    1.00    --   40.73 -77.00 150.00   37
 11  ω    -67.00  31.00   1.00    1.00    --  -40.73  57.00-120.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0012453000
_diffrn_orient_matrix_UB_12      0.2295785000
_diffrn_orient_matrix_UB_13      0.0402826000
_diffrn_orient_matrix_UB_21      0.0244265000
_diffrn_orient_matrix_UB_22      -0.1101374000
_diffrn_orient_matrix_UB_23      0.0833625000
_diffrn_orient_matrix_UB_31      0.2260592000
_diffrn_orient_matrix_UB_32      0.0107062000
_diffrn_orient_matrix_UB_33      -0.0048817000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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         0.302
_reflns_Friedel_fraction_full    0.393
_reflns_Friedel_fraction_max     0.355
_reflns_number_gt                1864
_reflns_number_total             1897
_reflns_odcompleteness_completeness 99.78
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.107
_refine_ls_abs_structure_details 
;
 Flack x determined using 415 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       0.0157(18)
_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   1.141
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         1897
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0834
_refine_ls_restrained_S_all      1.141
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0728P)²+3.7566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2455
_refine_ls_wR_factor_ref         0.2464
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C12(H12)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_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 -0.2023(4) 0.1630(7) 0.0983(2) 0.0340(9) Uani 1 1 d . . . . .
O2 O -0.2364(5) 0.5097(8) 0.0509(2) 0.0489(11) Uani 1 1 d . . . . .
O3 O 1.3049(4) 0.8989(6) 0.3666(2) 0.0313(9) Uani 1 1 d . . . . .
O4 O 1.1353(4) 0.4848(6) 0.39109(17) 0.0239(7) Uani 1 1 d . . . . .
O5 O 1.1424(5) 0.6494(7) 0.5123(2) 0.0349(9) Uani 1 1 d . . . . .
C1 C 0.0426(6) 0.4200(9) 0.1366(3) 0.0259(11) Uani 1 1 d . . . . .
C2 C 0.1268(6) 0.6288(9) 0.1318(3) 0.0271(11) Uani 1 1 d . . . . .
H2 H 0.065165 0.737710 0.100148 0.033 Uiso 1 1 calc R U . . .
C3 C 0.3034(6) 0.6747(9) 0.1744(2) 0.0234(10) Uani 1 1 d . . . . .
H3 H 0.358220 0.815403 0.171695 0.028 Uiso 1 1 calc R U . . .
C4 C 0.3990(6) 0.5125(8) 0.2212(2) 0.0224(10) Uani 1 1 d . . . . .
C5 C 0.3120(6) 0.3029(8) 0.2268(3) 0.0238(11) Uani 1 1 d . . . . .
H5 H 0.373105 0.193487 0.258377 0.029 Uiso 1 1 calc R U . . .
C6 C 0.1347(7) 0.2593(9) 0.1849(3) 0.0300(12) Uani 1 1 d . . . . .
H6 H 0.076607 0.120689 0.189314 0.036 Uiso 1 1 calc R U . . .
C7 C 0.5837(6) 0.5587(8) 0.2657(3) 0.0244(11) Uani 1 1 d . . . . .
C8 C 0.7062(6) 0.7681(9) 0.2709(3) 0.0240(11) Uani 1 1 d . . . . .
H8A H 0.645955 0.889548 0.298994 0.029 Uiso 1 1 calc R U . . .
H8B H 0.758111 0.815634 0.220392 0.029 Uiso 1 1 calc R U . . .
C9 C 0.8482(6) 0.6245(9) 0.3238(3) 0.0251(11) Uani 1 1 d . . . . .
C10 C 0.7132(6) 0.4399(8) 0.3134(3) 0.0270(12) Uani 1 1 d . . . . .
H10 H 0.714517 0.295006 0.332269 0.032 Uiso 1 1 calc R U . . .
C11 C 1.0278(6) 0.6586(9) 0.3572(2) 0.0236(10) Uani 1 1 d . . . . .
C12 C 1.1272(6) 0.8706(8) 0.3516(3) 0.0250(11) Uani 1 1 d . . . . .
H12 H 1.051838 0.992770 0.335619 0.030 Uiso 1 1 calc R U . . .
C13 C 1.1993(6) 0.5012(9) 0.4699(3) 0.0268(11) Uani 1 1 d . . . . .
C14 C 1.3393(7) 0.3250(10) 0.4927(3) 0.0310(12) Uani 1 1 d . . . . .
H14A H 1.274253 0.184241 0.488072 0.046 Uiso 1 1 calc R U . . .
H14B H 1.387466 0.346895 0.547354 0.046 Uiso 1 1 calc R U . . .
H14C H 1.447808 0.328545 0.457744 0.046 Uiso 1 1 calc R U . . .
C15 C -0.1464(6) 0.3769(10) 0.0904(3) 0.0283(12) Uani 1 1 d . . . . .
C16 C -0.3860(6) 0.1019(10) 0.0559(3) 0.0360(14) Uani 1 1 d . . . . .
H16A H -0.387879 0.159758 0.002148 0.054 Uiso 1 1 calc R U . . .
H16B H -0.494799 0.162001 0.083696 0.054 Uiso 1 1 calc R U . . .
H16C H -0.396928 -0.056341 0.053978 0.054 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
O1 C15 1.355(7) . ?
O1 C16 1.451(5) . ?
O2 C15 1.188(7) . ?
O3 C12 1.232(5) . ?
O4 C11 1.384(6) . ?
O4 C13 1.365(5) . ?
O5 C13 1.215(6) . ?
C1 C2 1.389(7) . ?
C1 C6 1.391(7) . ?
C1 C15 1.486(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(6) . ?
C4 C5 1.402(7) . ?
C4 C7 1.452(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.515(7) . ?
C7 C10 1.361(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.541(6) . ?
C9 C10 1.449(7) . ?
C9 C11 1.332(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.453(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.465(7) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C15 O1 C16 115.7(4) . . ?
C13 O4 C11 118.3(4) . . ?
C2 C1 C6 119.5(4) . . ?
C2 C1 C15 118.5(4) . . ?
C6 C1 C15 122.0(5) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.9(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 C7 121.1(4) . . ?
C5 C4 C7 119.7(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.8(4) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.9(5) . . ?
C5 C6 H6 119.6 . . ?
C4 C7 C8 130.4(4) . . ?
C10 C7 C4 135.5(5) . . ?
C10 C7 C8 94.0(4) . . ?
C7 C8 H8A 114.7 . . ?
C7 C8 H8B 114.7 . . ?
C7 C8 C9 83.6(4) . . ?
H8A C8 H8B 111.8 . . ?
C9 C8 H8A 114.7 . . ?
C9 C8 H8B 114.7 . . ?
C10 C9 C8 89.5(3) . . ?
C11 C9 C8 133.4(5) . . ?
C11 C9 C10 136.9(5) . . ?
C7 C10 C9 92.9(4) . . ?
C7 C10 H10 133.6 . . ?
C9 C10 H10 133.6 . . ?
O4 C11 C12 117.2(4) . . ?
C9 C11 O4 120.5(5) . . ?
C9 C11 C12 121.9(4) . . ?
O3 C12 C11 124.2(4) . . ?
O3 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
O4 C13 C14 111.7(4) . . ?
O5 C13 O4 121.1(4) . . ?
O5 C13 C14 127.2(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O1 C15 C1 110.8(4) . . ?
O2 C15 O1 124.0(4) . . ?
O2 C15 C1 125.1(5) . . ?
O1 C16 H16A 109.5 . . ?
O1 C16 H16B 109.5 . . ?
O1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
O4 C11 C12 O3 8.3(7) . . . . ?
C1 C2 C3 C4 0.9(7) . . . . ?
C2 C1 C6 C5 -1.7(7) . . . . ?
C2 C1 C15 O1 176.7(4) . . . . ?
C2 C1 C15 O2 -2.4(7) . . . . ?
C2 C3 C4 C5 -1.8(6) . . . . ?
C2 C3 C4 C7 179.8(4) . . . . ?
C3 C4 C5 C6 1.0(6) . . . . ?
C3 C4 C7 C8 -1.0(7) . . . . ?
C3 C4 C7 C10 -177.8(5) . . . . ?
C4 C5 C6 C1 0.8(7) . . . . ?
C4 C7 C8 C9 -177.2(5) . . . . ?
C4 C7 C10 C9 176.9(5) . . . . ?
C5 C4 C7 C8 -179.3(4) . . . . ?
C5 C4 C7 C10 3.8(8) . . . . ?
C6 C1 C2 C3 0.8(7) . . . . ?
C6 C1 C15 O1 -4.3(6) . . . . ?
C6 C1 C15 O2 176.6(5) . . . . ?
C7 C4 C5 C6 179.4(4) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C7 C8 C9 C11 173.9(5) . . . . ?
C8 C7 C10 C9 -0.6(4) . . . . ?
C8 C9 C10 C7 0.6(4) . . . . ?
C8 C9 C11 O4 -169.0(4) . . . . ?
C8 C9 C11 C12 3.8(8) . . . . ?
C9 C11 C12 O3 -164.7(5) . . . . ?
C10 C7 C8 C9 0.6(4) . . . . ?
C10 C9 C11 O4 2.9(8) . . . . ?
C10 C9 C11 C12 175.7(5) . . . . ?
C11 O4 C13 O5 9.6(6) . . . . ?
C11 O4 C13 C14 -169.8(4) . . . . ?
C11 C9 C10 C7 -173.5(6) . . . . ?
C13 O4 C11 C9 -123.2(5) . . . . ?
C13 O4 C11 C12 63.7(5) . . . . ?
C15 C1 C2 C3 179.8(4) . . . . ?
C15 C1 C6 C5 179.3(4) . . . . ?
C16 O1 C15 O2 -1.2(7) . . . . ?
C16 O1 C15 C1 179.7(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 1.502
_oxdiff_exptl_absorpt_empirical_full_min 0.480
