# 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 2021

####################################################################### 
# 
# 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_zhangxiao_bmz-9-2_collect
_database_code_depnum_ccdc_archive 'CCDC 2075017'
loop_
_audit_author_name
_audit_author_address
zhangsha
;Central South University
China
;
_audit_update_record             
;
2021-04-02 deposited with the CCDC.	2021-06-11 downloaded from the CCDC.
;
_audit_creation_date             2019-12-02
_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 H14 O5'
_chemical_formula_sum            'C12 H14 O5'
_chemical_formula_weight         238.23
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C99 H90 N9 O9 '
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      tetragonal
_space_group_IT_number           94
_space_group_name_H-M_alt        'P 42 21 2'
_space_group_name_Hall           'P 4n 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'y, x, -z'
'-y, -x, -z'

_cell_length_a                   18.0532(2)
_cell_length_b                   18.0532(2)
_cell_length_c                   6.74410(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2198.02(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4461
_cell_measurement_temperature    107(5)
_cell_measurement_theta_max      74.1230
_cell_measurement_theta_min      4.8980
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.764
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
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    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            5540
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.375
_diffrn_reflns_theta_min         4.899
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      107(5)
_diffrn_detector                 'Pilatus3R 200K-A'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00   5.00   0.20    0.70    --    0.00 -82.00  30.00  130
  2  ω    -33.00  27.00   0.20    0.70    --    0.00 -82.00  60.00  300
  3  ω     78.00 173.00   0.20    2.10    --   95.80  61.00 -90.00  475
  4  ω     72.00 107.00   0.20    2.10    --   95.80  61.00 -30.00  175
  5  ω     87.00 176.00   0.20    2.10    --   95.80  82.00  90.00  445
  6  ω    127.00 172.00   0.20    2.10    --   95.80  82.00 -60.00  225
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Pro: Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0230358000
_diffrn_orient_matrix_UB_12      0.0780445000
_diffrn_orient_matrix_UB_13      -0.0688423000
_diffrn_orient_matrix_UB_21      0.0753215000
_diffrn_orient_matrix_UB_22      -0.0093041000
_diffrn_orient_matrix_UB_23      0.1046246000
_diffrn_orient_matrix_UB_31      0.0330239000
_diffrn_orient_matrix_UB_32      -0.0331174000
_diffrn_orient_matrix_UB_33      -0.1909439000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'MicroMax 007 (Cu) X-ray Source'
_reflns_Friedel_coverage         0.640
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.936
_reflns_number_gt                2082
_reflns_number_total             2175
_reflns_odcompleteness_completeness 99.83
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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         0.270
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 
;
 Flack x determined using 744 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.22(16)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0611
_refine_ls_restrained_S_all      1.116
_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)+(0.0427P)²+3.7699P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.1501
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
2.d Idealised tetrahedral OH refined as rotating group:
 O0AA(H0AA), O1AA(H1AA), O4AA(H4AA)
;
_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
O0AA O 0.64208(18) 0.14186(17) 0.4691(4) 0.0239(7) Uani 1 1 d . . . . .
H0AA H 0.6703 0.1110 0.5166 0.036 Uiso 1 1 calc GR . . . .
O1AA O 0.75099(17) 0.41623(17) 0.2919(5) 0.0275(7) Uani 1 1 d . . . . .
H1AA H 0.7869 0.3952 0.3409 0.041 Uiso 1 1 calc GR . . . .
O2 O 0.53390(17) 0.14317(16) 0.1565(5) 0.0264(7) Uani 1 1 d . . . . .
O3AA O 0.45381(17) 0.23344(17) 0.1782(5) 0.0293(7) Uani 1 1 d . . . . .
O4AA O 0.49674(18) 0.36971(19) 0.2149(7) 0.0411(10) Uani 1 1 d . . . . .
H4AA H 0.4674 0.3354 0.2017 0.062 Uiso 1 1 calc GR . . . .
C4A C 0.6533(2) 0.2405(2) 0.2433(6) 0.0214(9) Uani 1 1 d . . . . .
C8A C 0.5803(2) 0.2663(2) 0.2169(6) 0.0232(9) Uani 1 1 d . . . . .
C5 C 0.7097(2) 0.2906(2) 0.2651(6) 0.0228(9) Uani 1 1 d . . . . .
H5 H 0.7582 0.2740 0.2775 0.027 Uiso 1 1 calc R . . . .
C6 C 0.6946(2) 0.3668(2) 0.2688(6) 0.0255(9) Uani 1 1 d . . . . .
C1 C 0.5202(3) 0.2148(2) 0.1834(6) 0.0244(9) Uani 1 1 d . . . . .
C4 C 0.6635(2) 0.1572(2) 0.2669(6) 0.0222(9) Uani 1 1 d . . . . .
C3 C 0.6097(3) 0.1182(2) 0.1238(7) 0.0257(10) Uani 1 1 d . . . . .
H3 H 0.6240 0.1306 -0.0125 0.031 Uiso 1 1 calc R . . . .
C8 C 0.5661(3) 0.3428(2) 0.2259(7) 0.0277(10) Uani 1 1 d . . . . .
C7 C 0.6235(3) 0.3941(2) 0.2515(8) 0.0293(10) Uani 1 1 d . . . . .
C9 C 0.6063(3) 0.0353(3) 0.1431(8) 0.0317(11) Uani 1 1 d . . . . .
H9A H 0.5946 0.0224 0.2775 0.048 Uiso 1 1 calc GR . . . .
H9B H 0.6534 0.0144 0.1079 0.048 Uiso 1 1 calc GR . . . .
H9C H 0.5688 0.0163 0.0562 0.048 Uiso 1 1 calc GR . . . .
C10 C 0.7420(2) 0.1311(3) 0.2266(8) 0.0297(10) Uani 1 1 d . . . . .
H10A H 0.7756 0.1561 0.3143 0.045 Uiso 1 1 calc GR . . . .
H10B H 0.7549 0.1421 0.0917 0.045 Uiso 1 1 calc GR . . . .
H10C H 0.7451 0.0787 0.2482 0.045 Uiso 1 1 calc GR . . . .
C11 C 0.6076(3) 0.4758(3) 0.2660(11) 0.0471(15) Uani 1 1 d . . . . .
H11A H 0.6524 0.5018 0.2973 0.071 Uiso 1 1 calc GR . . . .
H11B H 0.5716 0.4843 0.3683 0.071 Uiso 1 1 calc GR . . . .
H11C H 0.5885 0.4932 0.1416 0.071 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
O0AA H0AA 0.8200 . ?
O0AA C4 1.444(5) . ?
O1AA H1AA 0.8200 . ?
O1AA C6 1.363(5) . ?
O2 C1 1.329(5) . ?
O2 C3 1.458(5) . ?
O3AA C1 1.245(6) . ?
O4AA H4AA 0.8200 . ?
O4AA C8 1.345(5) . ?
C4A C8A 1.409(6) . ?
C4A C5 1.368(6) . ?
C4A C4 1.524(6) . ?
C8A C1 1.447(6) . ?
C8A C8 1.407(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(6) . ?
C6 C7 1.380(6) . ?
C4 C3 1.539(6) . ?
C4 C10 1.518(6) . ?
C3 H3 0.9800 . ?
C3 C9 1.504(6) . ?
C8 C7 1.401(6) . ?
C7 C11 1.506(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 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
C4 O0AA H0AA 109.5 . . ?
C6 O1AA H1AA 109.5 . . ?
C1 O2 C3 119.8(3) . . ?
C8 O4AA H4AA 109.5 . . ?
C8A C4A C4 116.8(4) . . ?
C5 C4A C8A 119.4(4) . . ?
C5 C4A C4 123.4(4) . . ?
C4A C8A C1 120.7(4) . . ?
C8 C8A C4A 119.3(4) . . ?
C8 C8A C1 120.1(4) . . ?
C4A C5 H5 119.8 . . ?
C4A C5 C6 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
O1AA C6 C5 120.0(4) . . ?
O1AA C6 C7 118.1(4) . . ?
C7 C6 C5 121.9(4) . . ?
O2 C1 C8A 120.4(4) . . ?
O3AA C1 O2 116.0(4) . . ?
O3AA C1 C8A 123.5(4) . . ?
O0AA C4 C4A 104.8(3) . . ?
O0AA C4 C3 109.6(3) . . ?
O0AA C4 C10 111.1(4) . . ?
C4A C4 C3 108.0(3) . . ?
C10 C4 C4A 113.6(4) . . ?
C10 C4 C3 109.5(4) . . ?
O2 C3 C4 110.9(3) . . ?
O2 C3 H3 108.6 . . ?
O2 C3 C9 104.8(4) . . ?
C4 C3 H3 108.6 . . ?
C9 C3 C4 115.3(4) . . ?
C9 C3 H3 108.6 . . ?
O4AA C8 C8A 121.5(4) . . ?
O4AA C8 C7 117.2(4) . . ?
C7 C8 C8A 121.3(4) . . ?
C6 C7 C8 117.6(4) . . ?
C6 C7 C11 121.5(4) . . ?
C8 C7 C11 120.9(4) . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C4 C10 H10A 109.5 . . ?
C4 C10 H10B 109.5 . . ?
C4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
O0AA C4 C3 O2 58.9(5) . . . . ?
O0AA C4 C3 C9 -59.9(5) . . . . ?
O1AA C6 C7 C8 179.4(4) . . . . ?
O1AA C6 C7 C11 -2.5(7) . . . . ?
O4AA C8 C7 C6 178.1(4) . . . . ?
O4AA C8 C7 C11 0.0(8) . . . . ?
C4A C8A C1 O2 -7.0(6) . . . . ?
C4A C8A C1 O3AA 172.8(4) . . . . ?
C4A C8A C8 O4AA -175.5(4) . . . . ?
C4A C8A C8 C7 3.0(7) . . . . ?
C4A C5 C6 O1AA 179.6(4) . . . . ?
C4A C5 C6 C7 0.2(7) . . . . ?
C4A C4 C3 O2 -54.8(4) . . . . ?
C4A C4 C3 C9 -173.6(4) . . . . ?
C8A C4A C5 C6 2.5(6) . . . . ?
C8A C4A C4 O0AA -77.7(4) . . . . ?
C8A C4A C4 C3 39.1(5) . . . . ?
C8A C4A C4 C10 160.8(4) . . . . ?
C8A C8 C7 C6 -0.4(7) . . . . ?
C8A C8 C7 C11 -178.5(5) . . . . ?
C5 C4A C8A C1 176.9(4) . . . . ?
C5 C4A C8A C8 -4.0(6) . . . . ?
C5 C4A C4 O0AA 96.0(5) . . . . ?
C5 C4A C4 C3 -147.2(4) . . . . ?
C5 C4A C4 C10 -25.5(6) . . . . ?
C5 C6 C7 C8 -1.2(7) . . . . ?
C5 C6 C7 C11 176.9(5) . . . . ?
C1 O2 C3 C4 43.4(5) . . . . ?
C1 O2 C3 C9 168.4(4) . . . . ?
C1 C8A C8 O4AA 3.7(7) . . . . ?
C1 C8A C8 C7 -177.9(5) . . . . ?
C4 C4A C8A C1 -9.2(6) . . . . ?
C4 C4A C8A C8 170.0(4) . . . . ?
C4 C4A C5 C6 -171.1(4) . . . . ?
C3 O2 C1 O3AA 168.7(4) . . . . ?
C3 O2 C1 C8A -11.4(6) . . . . ?
C8 C8A C1 O2 173.8(4) . . . . ?
C8 C8A C1 O3AA -6.4(7) . . . . ?
C10 C4 C3 O2 -179.0(4) . . . . ?
C10 C4 C3 C9 62.2(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 1.708
_oxdiff_exptl_absorpt_empirical_full_min 0.657
####################################################################### 
# 
# 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_zhangxiao_bmz-9-1_collect
_database_code_depnum_ccdc_archive 'CCDC 2075013'
loop_
_audit_author_name
_audit_author_address
Zhangsha
;Central South University
China
;
_audit_update_record             
;
2021-05-26 deposited with the CCDC.	2021-06-11 downloaded from the CCDC.
;
_audit_creation_date             2021-05-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '8(C12 H14 O5)'
_chemical_formula_sum            'C96 H112 O40'
_chemical_formula_weight         1905.85
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C99 H90 N9 O9 '
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      tetragonal
_space_group_IT_number           94
_space_group_name_H-M_alt        'P 42 21 2'
_space_group_name_Hall           'P 4n 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'y, x, -z'
'-y, -x, -z'

_cell_length_a                   18.0572(4)
_cell_length_b                   18.0572(4)
_cell_length_c                   6.7365(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2196.52(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2447
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      73.6430
_cell_measurement_theta_min      5.4800
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.950
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
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    1.441
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            5270
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.045
_diffrn_reflns_theta_max         67.045
_diffrn_reflns_theta_min         3.461
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      101(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_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    -33.00  -3.00   0.20    0.63    --    0.00 -82.00-120.00  150
  2  ω    -31.00  28.00   0.20    0.63    --    0.00 -82.00  30.00  295
  3  ω      7.00  86.00   0.20    2.51    --   95.80 -61.00 120.00  395
  4  ω     92.00 118.00   0.20    2.51    --   95.80 -61.00 120.00  130
  5  ω     87.00 164.00   0.20    2.51    --   95.80  82.00-150.00  385
  6  ω     96.00 175.00   0.20    2.51    --   95.80  45.00   0.00  395
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0118559000
_diffrn_orient_matrix_UB_12      -0.0829560000
_diffrn_orient_matrix_UB_13      -0.0421096000
_diffrn_orient_matrix_UB_21      0.0183339000
_diffrn_orient_matrix_UB_22      -0.0180315000
_diffrn_orient_matrix_UB_23      0.2178913000
_diffrn_orient_matrix_UB_31      -0.0826159000
_diffrn_orient_matrix_UB_32      0.0078679000
_diffrn_orient_matrix_UB_33      0.0543417000
_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         0.662
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                1887
_reflns_number_total             1964
_reflns_odcompleteness_completeness 99.92
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 686 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1964
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0633
_refine_ls_restrained_S_all      1.179
_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)+(0.0211P)²+4.4834P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1455
_refine_ls_wR_factor_ref         0.1464
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008)
2.c Idealised Me refined as rotating group:
 C00F(H00A,H00B,H00C), C00G(H00D,H00E,H00F), C00H(H00G,H00H,H00I)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O003(H003), O005(H005)
;
_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
O001 O 0.1420(2) 0.3580(2) 0.5309(5) 0.0305(8) Uani 1 1 d . . . . .
H001 H 0.1097 0.3311 0.4848 0.046 Uiso 1 1 calc R U . . .
O002 O 0.1435(2) 0.4661(2) 0.8435(6) 0.0315(9) Uani 1 1 d . . . . .
O003 O 0.4164(2) 0.2492(2) 0.7076(6) 0.0340(9) Uani 1 1 d . . . . .
H003 H 0.3964 0.2148 0.6486 0.051 Uiso 1 1 calc R U . . .
O004 O 0.2336(2) 0.5463(2) 0.8222(6) 0.0352(9) Uani 1 1 d . . . . .
O005 O 0.3702(2) 0.5036(2) 0.7855(8) 0.0485(12) Uani 1 1 d . . . . .
H005 H 0.3360 0.5328 0.8021 0.073 Uiso 1 1 calc R U . . .
C006 C 0.2412(3) 0.3467(3) 0.7564(8) 0.0268(11) Uani 1 1 d . . . . .
C007 C 0.2666(3) 0.4198(3) 0.7846(8) 0.0276(11) Uani 1 1 d . . . . .
C008 C 0.2905(3) 0.2907(3) 0.7349(7) 0.0266(11) Uani 1 1 d . . . . .
H008 H 0.2738 0.2422 0.7229 0.032 Uiso 1 1 calc R U . . .
C009 C 0.1186(3) 0.3899(3) 0.8758(8) 0.0313(12) Uani 1 1 d . . . . .
H009 H 0.1311 0.3757 1.0122 0.038 Uiso 1 1 calc R U . . .
C00A C 0.2153(3) 0.4798(3) 0.8167(8) 0.0306(12) Uani 1 1 d . . . . .
C00B C 0.1575(3) 0.3363(3) 0.7334(7) 0.0271(11) Uani 1 1 d . . . . .
C00C C 0.3947(3) 0.3771(3) 0.7478(9) 0.0355(13) Uani 1 1 d . . . . .
C00D C 0.3670(3) 0.3057(3) 0.7306(8) 0.0319(12) Uani 1 1 d . . . . .
C00E C 0.3434(3) 0.4342(3) 0.7743(9) 0.0342(13) Uani 1 1 d . . . . .
C00F C 0.0352(3) 0.3937(3) 0.8582(9) 0.0370(13) Uani 1 1 d . . . . .
H00A H 0.0164 0.4299 0.9494 0.056 Uiso 1 1 calc R U . . .
H00B H 0.0144 0.3461 0.8888 0.056 Uiso 1 1 calc R U . . .
H00C H 0.0220 0.4074 0.7252 0.056 Uiso 1 1 calc R U . . .
C00G C 0.1315(3) 0.2580(3) 0.7744(9) 0.0352(13) Uani 1 1 d . . . . .
H00D H 0.0793 0.2546 0.7502 0.053 Uiso 1 1 calc R U . . .
H00E H 0.1416 0.2456 0.9103 0.053 Uiso 1 1 calc R U . . .
H00F H 0.1573 0.2243 0.6887 0.053 Uiso 1 1 calc R U . . .
C00H C 0.4762(3) 0.3927(4) 0.7354(13) 0.056(2) Uani 1 1 d . . . . .
H00G H 0.4942 0.4076 0.8635 0.085 Uiso 1 1 calc R U . . .
H00H H 0.4848 0.4317 0.6413 0.085 Uiso 1 1 calc R U . . .
H00I H 0.5018 0.3489 0.6934 0.085 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
O001 H001 0.8200 . ?
O001 C00B 1.447(6) . ?
O002 C009 1.464(7) . ?
O002 C00A 1.332(6) . ?
O003 H003 0.8200 . ?
O003 C00D 1.364(6) . ?
O004 C00A 1.247(7) . ?
O005 H005 0.8200 . ?
O005 C00E 1.347(7) . ?
C006 C007 1.411(7) . ?
C006 C008 1.355(7) . ?
C006 C00B 1.532(7) . ?
C007 C00A 1.442(7) . ?
C007 C00E 1.412(7) . ?
C008 H008 0.9300 . ?
C008 C00D 1.408(7) . ?
C009 H009 0.9800 . ?
C009 C00B 1.534(7) . ?
C009 C00F 1.511(7) . ?
C00B C00G 1.514(7) . ?
C00C C00D 1.387(8) . ?
C00C C00E 1.398(8) . ?
C00C C00H 1.502(8) . ?
C00F H00A 0.9600 . ?
C00F H00B 0.9600 . ?
C00F H00C 0.9600 . ?
C00G H00D 0.9600 . ?
C00G H00E 0.9600 . ?
C00G H00F 0.9600 . ?
C00H H00G 0.9600 . ?
C00H H00H 0.9600 . ?
C00H H00I 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
C00B O001 H001 109.5 . . ?
C00A O002 C009 119.6(4) . . ?
C00D O003 H003 109.5 . . ?
C00E O005 H005 109.5 . . ?
C007 C006 C00B 116.7(4) . . ?
C008 C006 C007 120.0(5) . . ?
C008 C006 C00B 123.1(5) . . ?
C006 C007 C00A 120.9(5) . . ?
C006 C007 C00E 119.0(5) . . ?
C00E C007 C00A 120.0(5) . . ?
C006 C008 H008 119.9 . . ?
C006 C008 C00D 120.2(5) . . ?
C00D C008 H008 119.9 . . ?
O002 C009 H009 108.4 . . ?
O002 C009 C00B 111.1(4) . . ?
O002 C009 C00F 104.7(4) . . ?
C00B C009 H009 108.4 . . ?
C00F C009 H009 108.4 . . ?
C00F C009 C00B 115.8(5) . . ?
O002 C00A C007 120.5(5) . . ?
O004 C00A O002 115.6(5) . . ?
O004 C00A C007 123.9(5) . . ?
O001 C00B C006 104.6(4) . . ?
O001 C00B C009 109.3(4) . . ?
O001 C00B C00G 111.4(4) . . ?
C006 C00B C009 108.2(4) . . ?
C00G C00B C006 113.7(4) . . ?
C00G C00B C009 109.5(4) . . ?
C00D C00C C00E 117.2(5) . . ?
C00D C00C C00H 121.6(5) . . ?
C00E C00C C00H 121.2(5) . . ?
O003 C00D C008 119.9(5) . . ?
O003 C00D C00C 118.0(5) . . ?
C00C C00D C008 122.0(5) . . ?
O005 C00E C007 121.5(5) . . ?
O005 C00E C00C 117.1(5) . . ?
C00C C00E C007 121.4(5) . . ?
C009 C00F H00A 109.5 . . ?
C009 C00F H00B 109.5 . . ?
C009 C00F H00C 109.5 . . ?
H00A C00F H00B 109.5 . . ?
H00A C00F H00C 109.5 . . ?
H00B C00F H00C 109.5 . . ?
C00B C00G H00D 109.5 . . ?
C00B C00G H00E 109.5 . . ?
C00B C00G H00F 109.5 . . ?
H00D C00G H00E 109.5 . . ?
H00D C00G H00F 109.5 . . ?
H00E C00G H00F 109.5 . . ?
C00C C00H H00G 109.5 . . ?
C00C C00H H00H 109.5 . . ?
C00C C00H H00I 109.5 . . ?
H00G C00H H00H 109.5 . . ?
H00G C00H H00I 109.5 . . ?
H00H C00H H00I 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
O002 C009 C00B O001 -59.0(5) . . . . ?
O002 C009 C00B C006 54.4(5) . . . . ?
O002 C009 C00B C00G 178.8(4) . . . . ?
C006 C007 C00A O002 7.9(8) . . . . ?
C006 C007 C00A O004 -172.4(5) . . . . ?
C006 C007 C00E O005 175.1(5) . . . . ?
C006 C007 C00E C00C -3.6(9) . . . . ?
C006 C008 C00D O003 -179.6(5) . . . . ?
C006 C008 C00D C00C 0.0(8) . . . . ?
C007 C006 C008 C00D -3.2(8) . . . . ?
C007 C006 C00B O001 78.2(5) . . . . ?
C007 C006 C00B C009 -38.3(6) . . . . ?
C007 C006 C00B C00G -160.1(5) . . . . ?
C008 C006 C007 C00A -177.2(5) . . . . ?
C008 C006 C007 C00E 5.0(8) . . . . ?
C008 C006 C00B O001 -96.4(6) . . . . ?
C008 C006 C00B C009 147.2(5) . . . . ?
C008 C006 C00B C00G 25.4(7) . . . . ?
C009 O002 C00A O004 -168.9(5) . . . . ?
C009 O002 C00A C007 10.9(7) . . . . ?
C00A O002 C009 C00B -43.2(6) . . . . ?
C00A O002 C009 C00F -168.8(5) . . . . ?
C00A C007 C00E O005 -2.8(9) . . . . ?
C00A C007 C00E C00C 178.5(6) . . . . ?
C00B C006 C007 C00A 8.1(7) . . . . ?
C00B C006 C007 C00E -169.8(5) . . . . ?
C00B C006 C008 C00D 171.2(5) . . . . ?
C00D C00C C00E O005 -178.2(6) . . . . ?
C00D C00C C00E C007 0.5(9) . . . . ?
C00E C007 C00A O002 -174.2(5) . . . . ?
C00E C007 C00A O004 5.5(8) . . . . ?
C00E C00C C00D O003 -179.1(5) . . . . ?
C00E C00C C00D C008 1.4(9) . . . . ?
C00F C009 C00B O001 60.2(6) . . . . ?
C00F C009 C00B C006 173.6(4) . . . . ?
C00F C009 C00B C00G -62.1(6) . . . . ?
C00H C00C C00D O003 1.9(9) . . . . ?
C00H C00C C00D C008 -177.7(6) . . . . ?
C00H C00C C00E O005 0.8(10) . . . . ?
C00H C00C C00E C007 179.5(6) . . . . ?

_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 1.500
_oxdiff_exptl_absorpt_empirical_full_min 0.753
