# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ss24
_database_code_depnum_ccdc_archive 'CCDC 2169275'
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_audit_creation_date             2022-04-11
_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         'C19 H17 Br O4'
_chemical_formula_sum            'C19 H17 Br O4'
_chemical_formula_weight         389.23
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.8846(3)
_cell_length_b                   10.4690(6)
_cell_length_c                   18.3384(9)
_cell_angle_alpha                90(4)
_cell_angle_beta                 79.975(4)
_cell_angle_gamma                90(4)
_cell_volume                     1679.66(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7685
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5250
_cell_measurement_theta_min      3.3510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.467
_exptl_absorpt_correction_T_max  35
_exptl_absorpt_correction_T_min  25
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            clear
_exptl_crystal_colour_lustre     clear
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19410
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.130
_diffrn_reflns_theta_min         2.979
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3264
_reflns_number_total             4138
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.385
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       0.0542(17)
_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   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0390P)²+0.4901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0874
_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:
 C00E(H00A,H00B), C00L(H00E,H00G), C00M(H00I,H00J), C00N(H00K,H00L)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00C(H00C), C00D(H00D), C00F(H00F), C00H(H00H)
2.c Idealised Me refined as rotating group:
 C00O(H00M,H00N,H00O)
;
_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
Br01 Br 1.11534(2) 0.76994(3) 0.83292(2) 0.05603(12) Uani 1 1 d . . . . .
O002 O 0.37909(15) 0.28796(12) 0.54779(8) 0.0397(3) Uani 1 1 d . . . . .
O003 O 0.25013(16) 0.88602(13) 0.63237(9) 0.0490(4) Uani 1 1 d . . . . .
O004 O 0.47723(17) 0.88886(13) 0.69072(9) 0.0501(4) Uani 1 1 d . . . . .
O005 O 0.60118(17) 0.28624(15) 0.59060(10) 0.0531(4) Uani 1 1 d . . . . .
C006 C 0.44902(19) 0.47483(17) 0.60367(10) 0.0315(4) Uani 1 1 d . . . . .
C007 C 0.54234(19) 0.55019(17) 0.64062(10) 0.0325(4) Uani 1 1 d . . . . .
H007 H 0.633627 0.523362 0.653947 0.039 Uiso 1 1 calc R U . . .
C008 C 0.32043(19) 0.54853(17) 0.59331(10) 0.0314(4) Uani 1 1 d . . . . .
C009 C 0.47750(19) 0.67247(17) 0.65457(10) 0.0324(4) Uani 1 1 d . . . . .
C00A C 0.33618(19) 0.67112(17) 0.62267(10) 0.0324(4) Uani 1 1 d . . . . .
C00B C 0.4867(2) 0.34202(18) 0.58114(10) 0.0349(4) Uani 1 1 d . . . . .
C00C C 0.7705(2) 0.87816(19) 0.71942(11) 0.0408(5) Uani 1 1 d . . . . .
H00C H 0.745596 0.950601 0.694657 0.049 Uiso 1 1 calc R U . . .
C00D C 0.8408(2) 0.66458(19) 0.79690(11) 0.0380(4) Uani 1 1 d . . . . .
H00D H 0.863348 0.594100 0.823953 0.046 Uiso 1 1 calc R U . . .
C00E C 0.1876(2) 0.51356(19) 0.55667(11) 0.0393(4) Uani 1 1 d . . . . .
H00A H 0.155107 0.427116 0.570409 0.047 Uiso 1 1 calc R U . . .
H00B H 0.218947 0.516298 0.503321 0.047 Uiso 1 1 calc R U . . .
C00F C 0.9007(2) 0.8780(2) 0.75157(12) 0.0450(5) Uani 1 1 d . . . . .
H00F H 0.963891 0.949254 0.747683 0.054 Uiso 1 1 calc R U . . .
C00G C 0.5372(2) 0.77671(17) 0.68886(11) 0.0344(4) Uani 1 1 d . . . . .
C00H C 0.7122(2) 0.66465(18) 0.76364(11) 0.0365(4) Uani 1 1 d . . . . .
H00H H 0.649189 0.593209 0.767911 0.044 Uiso 1 1 calc R U . . .
C00I C 0.6762(2) 0.77039(17) 0.72387(11) 0.0330(4) Uani 1 1 d . . . . .
C00J C 0.2350(2) 0.77086(19) 0.61218(12) 0.0371(4) Uani 1 1 d . . . . .
C00K C 0.9356(2) 0.77088(19) 0.78943(12) 0.0388(4) Uani 1 1 d . . . . .
C00L C 0.0540(2) 0.6055(2) 0.57977(14) 0.0506(6) Uani 1 1 d . . . . .
H00E H -0.023506 0.590468 0.549468 0.061 Uiso 1 1 calc R U . . .
H00G H 0.008551 0.589721 0.630992 0.061 Uiso 1 1 calc R U . . .
C00M C 0.4028(2) 0.15623(18) 0.52504(12) 0.0420(5) Uani 1 1 d . . . . .
H00I H 0.412430 0.102887 0.567238 0.050 Uiso 1 1 calc R U . . .
H00J H 0.495406 0.147941 0.488502 0.050 Uiso 1 1 calc R U . . .
C00N C 0.1068(2) 0.7432(2) 0.57112(14) 0.0494(6) Uani 1 1 d . . . . .
H00K H 0.140164 0.761553 0.518971 0.059 Uiso 1 1 calc R U . . .
H00L H 0.021320 0.799108 0.589328 0.059 Uiso 1 1 calc R U . . .
C00O C 0.2653(3) 0.1163(2) 0.49222(13) 0.0556(6) Uani 1 1 d . . . . .
H00M H 0.254433 0.172292 0.451985 0.083 Uiso 1 1 calc R U . . .
H00N H 0.175180 0.121200 0.529556 0.083 Uiso 1 1 calc R U . . .
H00O H 0.279026 0.030224 0.474301 0.083 Uiso 1 1 calc R U . . .
H003 H 0.370(3) 0.895(4) 0.6633(18) 0.110(12) Uiso 1 1 d . . . . .


_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
Br01 C00K 1.905(2) . ?
O002 C00B 1.347(2) . ?
O002 C00M 1.445(2) . ?
O003 C00J 1.275(2) . ?
O003 H003 1.29(3) . ?
O004 C00G 1.287(2) . ?
O004 H003 1.16(3) . ?
O005 C00B 1.210(2) . ?
C006 C007 1.402(2) . ?
C006 C008 1.418(2) . ?
C006 C00B 1.472(3) . ?
C007 H007 0.9300 . ?
C007 C009 1.408(3) . ?
C008 C00A 1.408(2) . ?
C008 C00E 1.502(2) . ?
C009 C00A 1.475(2) . ?
C009 C00G 1.409(3) . ?
C00A C00J 1.412(3) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.386(3) . ?
C00C C00I 1.400(3) . ?
C00D H00D 0.9300 . ?
C00D C00H 1.385(3) . ?
C00D C00K 1.389(3) . ?
C00E H00A 0.9700 . ?
C00E H00B 0.9700 . ?
C00E C00L 1.529(3) . ?
C00F H00F 0.9300 . ?
C00F C00K 1.382(3) . ?
C00G C00I 1.489(3) . ?
C00H H00H 0.9300 . ?
C00H C00I 1.393(3) . ?
C00J C00N 1.500(3) . ?
C00L H00E 0.9700 . ?
C00L H00G 0.9700 . ?
C00L C00N 1.516(3) . ?
C00M H00I 0.9700 . ?
C00M H00J 0.9700 . ?
C00M C00O 1.512(3) . ?
C00N H00K 0.9700 . ?
C00N H00L 0.9700 . ?
C00O H00M 0.9600 . ?
C00O H00N 0.9600 . ?
C00O H00O 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 O002 C00M 116.96(14) . . ?
C00J O003 H003 109.7(16) . . ?
C00G O004 H003 114.3(18) . . ?
C007 C006 C008 108.47(15) . . ?
C007 C006 C00B 122.87(15) . . ?
C008 C006 C00B 128.66(15) . . ?
C006 C007 H007 125.0 . . ?
C006 C007 C009 110.00(15) . . ?
C009 C007 H007 125.0 . . ?
C006 C008 C00E 129.90(16) . . ?
C00A C008 C006 107.93(14) . . ?
C00A C008 C00E 122.15(16) . . ?
C007 C009 C00A 105.54(15) . . ?
C007 C009 C00G 127.67(16) . . ?
C00G C009 C00A 126.73(16) . . ?
C008 C00A C009 108.03(15) . . ?
C008 C00A C00J 120.89(16) . . ?
C00J C00A C009 130.72(17) . . ?
O002 C00B C006 112.34(15) . . ?
O005 C00B O002 122.89(17) . . ?
O005 C00B C006 124.77(17) . . ?
C00F C00C H00C 119.7 . . ?
C00F C00C C00I 120.65(19) . . ?
C00I C00C H00C 119.7 . . ?
C00H C00D H00D 120.4 . . ?
C00H C00D C00K 119.29(19) . . ?
C00K C00D H00D 120.4 . . ?
C008 C00E H00A 109.5 . . ?
C008 C00E H00B 109.5 . . ?
C008 C00E C00L 110.79(15) . . ?
H00A C00E H00B 108.1 . . ?
C00L C00E H00A 109.5 . . ?
C00L C00E H00B 109.5 . . ?
C00C C00F H00F 120.3 . . ?
C00K C00F C00C 119.41(18) . . ?
C00K C00F H00F 120.3 . . ?
O004 C00G C009 122.14(17) . . ?
O004 C00G C00I 113.51(16) . . ?
C009 C00G C00I 124.32(16) . . ?
C00D C00H H00H 119.6 . . ?
C00D C00H C00I 120.83(17) . . ?
C00I C00H H00H 119.6 . . ?
C00C C00I C00G 118.21(17) . . ?
C00H C00I C00C 118.79(17) . . ?
C00H C00I C00G 122.93(16) . . ?
O003 C00J C00A 123.87(18) . . ?
O003 C00J C00N 117.19(17) . . ?
C00A C00J C00N 118.85(17) . . ?
C00D C00K Br01 119.57(16) . . ?
C00F C00K Br01 119.45(14) . . ?
C00F C00K C00D 120.97(18) . . ?
C00E C00L H00E 109.4 . . ?
C00E C00L H00G 109.4 . . ?
H00E C00L H00G 108.0 . . ?
C00N C00L C00E 110.98(17) . . ?
C00N C00L H00E 109.4 . . ?
C00N C00L H00G 109.4 . . ?
O002 C00M H00I 110.3 . . ?
O002 C00M H00J 110.3 . . ?
O002 C00M C00O 106.97(16) . . ?
H00I C00M H00J 108.6 . . ?
C00O C00M H00I 110.3 . . ?
C00O C00M H00J 110.3 . . ?
C00J C00N C00L 112.35(17) . . ?
C00J C00N H00K 109.1 . . ?
C00J C00N H00L 109.1 . . ?
C00L C00N H00K 109.1 . . ?
C00L C00N H00L 109.1 . . ?
H00K C00N H00L 107.9 . . ?
C00M C00O H00M 109.5 . . ?
C00M C00O H00N 109.5 . . ?
C00M C00O H00O 109.5 . . ?
H00M C00O H00N 109.5 . . ?
H00M C00O H00O 109.5 . . ?
H00N C00O H00O 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
O003 C00J C00N C00L -154.3(2) . . . . ?
O004 C00G C00I C00C -32.5(3) . . . . ?
O004 C00G C00I C00H 144.4(2) . . . . ?
C006 C007 C009 C00A -0.9(2) . . . . ?
C006 C007 C009 C00G -178.44(19) . . . . ?
C006 C008 C00A C009 -1.8(2) . . . . ?
C006 C008 C00A C00J 172.02(18) . . . . ?
C006 C008 C00E C00L 161.9(2) . . . . ?
C007 C006 C008 C00A 1.2(2) . . . . ?
C007 C006 C008 C00E 179.60(18) . . . . ?
C007 C006 C00B O002 178.83(17) . . . . ?
C007 C006 C00B O005 -1.6(3) . . . . ?
C007 C009 C00A C008 1.7(2) . . . . ?
C007 C009 C00A C00J -171.3(2) . . . . ?
C007 C009 C00G O004 171.4(2) . . . . ?
C007 C009 C00G C00I -6.5(3) . . . . ?
C008 C006 C007 C009 -0.2(2) . . . . ?
C008 C006 C00B O002 -1.3(3) . . . . ?
C008 C006 C00B O005 178.3(2) . . . . ?
C008 C00A C00J O003 -174.41(19) . . . . ?
C008 C00A C00J C00N 1.9(3) . . . . ?
C008 C00E C00L C00N 49.6(2) . . . . ?
C009 C00A C00J O003 -2.2(4) . . . . ?
C009 C00A C00J C00N 174.12(19) . . . . ?
C009 C00G C00I C00C 145.6(2) . . . . ?
C009 C00G C00I C00H -37.5(3) . . . . ?
C00A C008 C00E C00L -20.0(3) . . . . ?
C00A C009 C00G O004 -5.6(3) . . . . ?
C00A C009 C00G C00I 176.43(18) . . . . ?
C00A C00J C00N C00L 29.1(3) . . . . ?
C00B O002 C00M C00O 177.82(17) . . . . ?
C00B C006 C007 C009 179.71(17) . . . . ?
C00B C006 C008 C00A -178.63(19) . . . . ?
C00B C006 C008 C00E -0.3(3) . . . . ?
C00C C00F C00K Br01 179.47(16) . . . . ?
C00C C00F C00K C00D -1.2(3) . . . . ?
C00D C00H C00I C00C -1.4(3) . . . . ?
C00D C00H C00I C00G -178.26(18) . . . . ?
C00E C008 C00A C009 179.70(16) . . . . ?
C00E C008 C00A C00J -6.5(3) . . . . ?
C00E C00L C00N C00J -54.9(3) . . . . ?
C00F C00C C00I C00G 179.45(19) . . . . ?
C00F C00C C00I C00H 2.5(3) . . . . ?
C00G C009 C00A C008 179.23(19) . . . . ?
C00G C009 C00A C00J 6.2(3) . . . . ?
C00H C00D C00K Br01 -178.45(15) . . . . ?
C00H C00D C00K C00F 2.2(3) . . . . ?
C00I C00C C00F C00K -1.2(3) . . . . ?
C00K C00D C00H C00I -0.9(3) . . . . ?
C00M O002 C00B O005 1.9(3) . . . . ?
C00M O002 C00B C006 -178.48(16) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_22julb_0m
_database_code_depnum_ccdc_archive 'CCDC 2169277'
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_audit_creation_date             2021-09-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 O4 S'
_chemical_formula_sum            'C21 H19 O4 S'
_chemical_formula_weight         367.42
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6775(6)
_cell_length_b                   9.7016(6)
_cell_length_c                   11.8817(8)
_cell_angle_alpha                86.390(2)
_cell_angle_beta                 79.605(2)
_cell_angle_gamma                66.426(2)
_cell_volume                     901.70(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6757
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.22
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             386
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.6
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            20304
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_min         2.291
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3976
_reflns_number_total             4474
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4474
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.100
_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)+(0.0559P)²+0.3597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1084
_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 Ternary CH refined with riding coordinates:
 C00L(H00L)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00B,H00C), C00J(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00G(H00G), C00H(H00H), C00K(H00K), C00M(H00M), C00O(H00O),
 C00P(H00P)
2.d Idealised Me refined as rotating group:
 C00N(H00F,H00I,H00J), C00Q(H00N,H00Q,H00R)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
S001 S 0.84346(4) 0.43648(4) 0.48815(3) 0.01655(10) Uani 1 1 d . . . . .
O002 O 0.79020(12) 0.10962(10) 0.20773(7) 0.01204(19) Uani 1 1 d . . . . .
O003 O 0.54977(12) 0.00282(11) 0.21589(8) 0.0150(2) Uani 1 1 d . . . . .
O004 O 1.01000(13) 0.15562(12) 0.35313(8) 0.0192(2) Uani 1 1 d . . . . .
O005 O 0.60012(14) -0.11442(12) 0.38329(9) 0.0222(2) Uani 1 1 d . . . . .
C006 C 0.89556(16) 0.05132(14) 0.10489(10) 0.0114(2) Uani 1 1 d . . . . .
C007 C 0.97089(16) -0.10144(14) 0.07866(10) 0.0120(2) Uani 1 1 d . . . . .
C008 C 0.63362(17) -0.04094(14) 0.30361(11) 0.0139(3) Uani 1 1 d . . . . .
C009 C 0.84586(17) 0.32166(14) 0.04701(11) 0.0135(2) Uani 1 1 d . . . . .
C00A C 0.63048(18) 0.31807(16) 0.57053(11) 0.0168(3) Uani 1 1 d . . . . .
H00A H 0.573272 0.253909 0.582906 0.020 Uiso 1 1 calc R U . . .
C00B C 0.77741(17) 0.00976(14) 0.29547(10) 0.0126(2) Uani 1 1 d . . . . .
C00C C 0.92267(16) 0.15611(14) 0.02589(10) 0.0116(2) Uani 1 1 d . . . . .
C00D C 0.87564(17) 0.16405(15) 0.41315(10) 0.0142(3) Uani 1 1 d . . . . .
C00E C 0.77386(17) 0.29252(15) 0.48919(11) 0.0140(3) Uani 1 1 d . . . . .
C00F C 0.93100(18) -0.09688(15) 0.34317(11) 0.0164(3) Uani 1 1 d . . . . .
H00B H 0.930514 -0.192816 0.371234 0.020 Uiso 1 1 calc R U . . .
H00C H 1.041891 -0.100174 0.306797 0.020 Uiso 1 1 calc R U . . .
C00G C 0.87626(19) 0.38444(16) 0.13896(11) 0.0180(3) Uani 1 1 d . . . . .
H00G H 0.936444 0.322118 0.192680 0.022 Uiso 1 1 calc R U . . .
C00H C 0.57997(19) 0.45221(16) 0.63299(11) 0.0191(3) Uani 1 1 d . . . . .
H00H H 0.486476 0.485114 0.691811 0.023 Uiso 1 1 calc R U . . .
C00I C 0.68253(19) 0.52964(16) 0.59840(11) 0.0182(3) Uani 1 1 d . . . . .
C00J C 0.40115(18) -0.03593(17) 0.22619(12) 0.0180(3) Uani 1 1 d . . . . .
H00D H 0.321785 0.008088 0.295597 0.022 Uiso 1 1 calc R U . . .
H00E H 0.436491 -0.144226 0.229604 0.022 Uiso 1 1 calc R U . . .
C00K C 0.7253(2) 0.63375(16) 0.07172(13) 0.0245(3) Uani 1 1 d . . . . .
H00K H 0.687706 0.737489 0.078981 0.029 Uiso 1 1 calc R U . . .
C00L C 0.81153(17) 0.04183(15) 0.41141(11) 0.0147(3) Uani 1 1 d . . . . .
H00L H 0.737801 0.028746 0.480424 0.018 Uiso 1 1 calc R U . . .
C00M C 0.75084(19) 0.41708(16) -0.03072(12) 0.0204(3) Uani 1 1 d . . . . .
H00M H 0.727892 0.376617 -0.091466 0.024 Uiso 1 1 calc R U . . .
C00N C 0.6643(2) 0.67736(17) 0.64265(13) 0.0255(3) Uani 1 1 d . . . . .
H00F H 0.766214 0.665228 0.670335 0.038 Uiso 1 1 calc R U . . .
H00I H 0.568635 0.712175 0.703937 0.038 Uiso 1 1 calc R U . . .
H00J H 0.646201 0.749474 0.582076 0.038 Uiso 1 1 calc R U . . .
C00O C 0.8169(2) 0.53976(17) 0.15053(12) 0.0228(3) Uani 1 1 d . . . . .
H00O H 0.838775 0.580766 0.211480 0.027 Uiso 1 1 calc R U . . .
C00P C 0.6900(2) 0.57281(17) -0.01791(14) 0.0253(3) Uani 1 1 d . . . . .
H00P H 0.625712 0.635763 -0.069569 0.030 Uiso 1 1 calc R U . . .
C00Q C 0.3176(2) 0.0242(2) 0.12366(13) 0.0259(3) Uani 1 1 d . . . . .
H00N H 0.394120 -0.025463 0.055905 0.039 Uiso 1 1 calc R U . . .
H00Q H 0.289906 0.130379 0.118219 0.039 Uiso 1 1 calc R U . . .
H00R H 0.215076 0.006394 0.131113 0.039 Uiso 1 1 calc R U . . .
H007 H 0.948(2) -0.1720(19) 0.1307(14) 0.015(4) Uiso 1 1 d . . . . .


_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
S001 C00E 1.7278(13) . ?
S001 C00I 1.7212(14) . ?
O002 C006 1.3854(14) . ?
O002 C00B 1.3981(15) . ?
O003 C008 1.3292(16) . ?
O003 C00J 1.4644(16) . ?
O004 C00D 1.2270(16) . ?
O005 C008 1.2127(16) . ?
C006 C007 1.3894(18) . ?
C006 C00C 1.4004(17) . ?
C007 C00C 1.3981(17) 2_755 ?
C007 H007 0.951(17) . ?
C008 C00B 1.4999(18) . ?
C009 C00C 1.4903(17) . ?
C009 C00G 1.3965(19) . ?
C009 C00M 1.3951(19) . ?
C00A H00A 0.9300 . ?
C00A C00E 1.3758(18) . ?
C00A C00H 1.4086(19) . ?
C00B C00F 1.5046(19) . ?
C00B C00L 1.5352(17) . ?
C00D C00E 1.4570(18) . ?
C00D C00L 1.5003(18) . ?
C00F H00B 0.9700 . ?
C00F H00C 0.9700 . ?
C00F C00L 1.5037(18) . ?
C00G H00G 0.9300 . ?
C00G C00O 1.3909(19) . ?
C00H H00H 0.9300 . ?
C00H C00I 1.375(2) . ?
C00I C00N 1.496(2) . ?
C00J H00D 0.9700 . ?
C00J H00E 0.9700 . ?
C00J C00Q 1.497(2) . ?
C00K H00K 0.9300 . ?
C00K C00O 1.386(2) . ?
C00K C00P 1.385(2) . ?
C00L H00L 0.9800 . ?
C00M H00M 0.9300 . ?
C00M C00P 1.395(2) . ?
C00N H00F 0.9600 . ?
C00N H00I 0.9600 . ?
C00N H00J 0.9600 . ?
C00O H00O 0.9300 . ?
C00P H00P 0.9300 . ?
C00Q H00N 0.9600 . ?
C00Q H00Q 0.9600 . ?
C00Q H00R 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
C00I S001 C00E 91.96(7) . . ?
C006 O002 C00B 118.45(10) . . ?
C008 O003 C00J 114.14(10) . . ?
O002 C006 C007 123.29(11) . . ?
O002 C006 C00C 116.12(11) . . ?
C007 C006 C00C 120.60(11) . . ?
C006 C007 C00C 121.63(12) . 2_755 ?
C006 C007 H007 120.5(10) . . ?
C00C C007 H007 117.8(10) 2_755 . ?
O003 C008 C00B 113.23(11) . . ?
O005 C008 O003 124.69(12) . . ?
O005 C008 C00B 122.08(12) . . ?
C00G C009 C00C 121.40(12) . . ?
C00M C009 C00C 119.49(12) . . ?
C00M C009 C00G 118.98(12) . . ?
C00E C00A H00A 123.7 . . ?
C00E C00A C00H 112.51(12) . . ?
C00H C00A H00A 123.7 . . ?
O002 C00B C008 116.83(11) . . ?
O002 C00B C00F 121.90(11) . . ?
O002 C00B C00L 115.91(10) . . ?
C008 C00B C00F 115.55(11) . . ?
C008 C00B C00L 114.33(10) . . ?
C00F C00B C00L 59.29(8) . . ?
C006 C00C C009 123.94(11) . . ?
C007 C00C C006 117.77(11) 2_755 . ?
C007 C00C C009 118.28(11) 2_755 . ?
O004 C00D C00E 121.08(12) . . ?
O004 C00D C00L 121.10(12) . . ?
C00E C00D C00L 117.82(11) . . ?
C00A C00E S001 111.19(10) . . ?
C00A C00E C00D 130.67(12) . . ?
C00D C00E S001 118.02(10) . . ?
C00B C00F H00B 117.6 . . ?
C00B C00F H00C 117.6 . . ?
H00B C00F H00C 114.7 . . ?
C00L C00F C00B 61.37(9) . . ?
C00L C00F H00B 117.6 . . ?
C00L C00F H00C 117.6 . . ?
C009 C00G H00G 119.9 . . ?
C00O C00G C009 120.29(13) . . ?
C00O C00G H00G 119.9 . . ?
C00A C00H H00H 123.3 . . ?
C00I C00H C00A 113.34(12) . . ?
C00I C00H H00H 123.3 . . ?
C00H C00I S001 110.99(10) . . ?
C00H C00I C00N 127.99(13) . . ?
C00N C00I S001 120.99(11) . . ?
O003 C00J H00D 110.1 . . ?
O003 C00J H00E 110.1 . . ?
O003 C00J C00Q 107.95(11) . . ?
H00D C00J H00E 108.4 . . ?
C00Q C00J H00D 110.1 . . ?
C00Q C00J H00E 110.1 . . ?
C00O C00K H00K 120.1 . . ?
C00P C00K H00K 120.1 . . ?
C00P C00K C00O 119.86(13) . . ?
C00B C00L H00L 117.6 . . ?
C00D C00L C00B 116.13(10) . . ?
C00D C00L C00F 115.84(11) . . ?
C00D C00L H00L 117.6 . . ?
C00F C00L C00B 59.34(8) . . ?
C00F C00L H00L 117.6 . . ?
C009 C00M H00M 119.8 . . ?
C009 C00M C00P 120.44(14) . . ?
C00P C00M H00M 119.8 . . ?
C00I C00N H00F 109.5 . . ?
C00I C00N H00I 109.5 . . ?
C00I C00N H00J 109.5 . . ?
H00F C00N H00I 109.5 . . ?
H00F C00N H00J 109.5 . . ?
H00I C00N H00J 109.5 . . ?
C00G C00O H00O 119.8 . . ?
C00K C00O C00G 120.35(14) . . ?
C00K C00O H00O 119.8 . . ?
C00K C00P C00M 120.04(14) . . ?
C00K C00P H00P 120.0 . . ?
C00M C00P H00P 120.0 . . ?
C00J C00Q H00N 109.5 . . ?
C00J C00Q H00Q 109.5 . . ?
C00J C00Q H00R 109.5 . . ?
H00N C00Q H00Q 109.5 . . ?
H00N C00Q H00R 109.5 . . ?
H00Q C00Q H00R 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 C006 C007 C00C -179.64(11) . . . 2_755 ?
O002 C006 C00C C007 179.64(11) . . . 2_755 ?
O002 C006 C00C C009 0.03(19) . . . . ?
O002 C00B C00F C00L 103.23(13) . . . . ?
O002 C00B C00L C00D -7.37(16) . . . . ?
O002 C00B C00L C00F -113.25(13) . . . . ?
O003 C008 C00B O002 7.94(16) . . . . ?
O003 C008 C00B C00F -145.97(11) . . . . ?
O003 C008 C00B C00L 147.93(11) . . . . ?
O004 C00D C00E S001 2.57(17) . . . . ?
O004 C00D C00E C00A -173.01(14) . . . . ?
O004 C00D C00L C00B -59.95(17) . . . . ?
O004 C00D C00L C00F 6.88(18) . . . . ?
O005 C008 C00B O002 -172.05(12) . . . . ?
O005 C008 C00B C00F 34.04(18) . . . . ?
O005 C008 C00B C00L -32.06(18) . . . . ?
C006 O002 C00B C008 -93.73(13) . . . . ?
C006 O002 C00B C00F 58.41(15) . . . . ?
C006 O002 C00B C00L 126.91(12) . . . . ?
C007 C006 C00C C007 -0.8(2) . . . 2_755 ?
C007 C006 C00C C009 179.59(12) . . . . ?
C008 O003 C00J C00Q 178.31(11) . . . . ?
C008 C00B C00F C00L -104.31(12) . . . . ?
C008 C00B C00L C00D -147.74(12) . . . . ?
C008 C00B C00L C00F 106.38(13) . . . . ?
C009 C00G C00O C00K 0.8(2) . . . . ?
C009 C00M C00P C00K 0.7(2) . . . . ?
C00A C00H C00I S001 -0.20(16) . . . . ?
C00A C00H C00I C00N 178.04(14) . . . . ?
C00B O002 C006 C007 9.12(18) . . . . ?
C00B O002 C006 C00C -171.33(11) . . . . ?
C00B C00F C00L C00D -106.36(12) . . . . ?
C00C C006 C007 C00C 0.8(2) . . . 2_755 ?
C00C C009 C00G C00O 173.75(13) . . . . ?
C00C C009 C00M C00P -174.55(13) . . . . ?
C00E S001 C00I C00H -0.42(11) . . . . ?
C00E S001 C00I C00N -178.80(12) . . . . ?
C00E C00A C00H C00I 0.92(18) . . . . ?
C00E C00D C00L C00B 120.56(13) . . . . ?
C00E C00D C00L C00F -172.61(11) . . . . ?
C00F C00B C00L C00D 105.88(13) . . . . ?
C00G C009 C00C C006 59.02(18) . . . . ?
C00G C009 C00C C007 -120.58(14) . . . 2_755 ?
C00G C009 C00M C00P 1.2(2) . . . . ?
C00H C00A C00E S001 -1.22(15) . . . . ?
C00H C00A C00E C00D 174.60(13) . . . . ?
C00I S001 C00E C00A 0.94(11) . . . . ?
C00I S001 C00E C00D -175.47(11) . . . . ?
C00J O003 C008 O005 4.25(18) . . . . ?
C00J O003 C008 C00B -175.74(11) . . . . ?
C00L C00D C00E S001 -177.94(9) . . . . ?
C00L C00D C00E C00A 6.5(2) . . . . ?
C00M C009 C00C C006 -125.31(14) . . . . ?
C00M C009 C00C C007 55.09(18) . . . 2_755 ?
C00M C009 C00G C00O -1.9(2) . . . . ?
C00O C00K C00P C00M -1.9(2) . . . . ?
C00P C00K C00O C00G 1.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_21octd_0m
_database_code_depnum_ccdc_archive 'CCDC 2169276'
_audit_update_record             
;
2022-04-28 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_audit_creation_date             2021-11-18
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6257)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 O4'
_chemical_formula_sum            'C26 H20 O4'
_chemical_formula_weight         396.42
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   7.3447(5)
_cell_length_b                   21.7403(15)
_cell_length_c                   12.7291(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.687(2)
_cell_angle_gamma                90
_cell_volume                     1974.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7019
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1388 before and 0.0589 after correction.
The Ratio of minimum to maximum transmission is 0.9413.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            31839
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.309
_diffrn_reflns_theta_min         2.495
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4083
_reflns_number_total             4896
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_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         0.360
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4896
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.190
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1621
_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:
 C00Q(H00B,H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00A(H00A), C00C(H00C), C00D(H00D), C00H(H00H), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00R(H00R),
 C00S(H00S), C00U(H00U)
2.c Idealised Me refined as rotating group:
 C00T(H00F,H00G,H00I)
;
_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
O001 O 0.73960(13) 0.50540(4) 0.78498(8) 0.0179(2) Uani 1 1 d . . . . .
O002 O 0.78251(15) 0.54052(4) 0.25340(8) 0.0215(2) Uani 1 1 d . . . . .
O003 O 0.79594(16) 0.64088(5) 0.34303(8) 0.0253(3) Uani 1 1 d . . . . .
O004 O 0.75449(18) 0.40958(5) 0.72032(9) 0.0299(3) Uani 1 1 d . . . . .
C005 C 0.78878(18) 0.62984(6) 0.44069(11) 0.0170(3) Uani 1 1 d . . . . .
C006 C 0.77420(17) 0.55933(6) 0.59082(11) 0.0139(3) Uani 1 1 d . . . . .
H006 H 0.780248 0.589359 0.643573 0.017 Uiso 1 1 calc R U . . .
C007 C 0.76212(17) 0.50986(6) 0.42834(11) 0.0140(3) Uani 1 1 d . . . . .
C008 C 0.76197(17) 0.49573(6) 0.60651(11) 0.0147(3) Uani 1 1 d . . . . .
C009 C 0.75957(18) 0.49788(6) 0.31872(11) 0.0153(3) Uani 1 1 d . . . . .
C00A C 0.75662(18) 0.46571(6) 0.50852(11) 0.0153(3) Uani 1 1 d . . . . .
H00A H 0.750422 0.423357 0.498034 0.018 Uiso 1 1 calc R U . . .
C00B C 0.79441(19) 0.68417(6) 0.51350(11) 0.0170(3) Uani 1 1 d . . . . .
C00C C 0.60232(18) 0.39400(6) 0.29476(11) 0.0171(3) Uani 1 1 d . . . . .
H00C H 0.534856 0.404558 0.345399 0.021 Uiso 1 1 calc R U . . .
C00D C 0.83339(19) 0.41882(6) 0.19471(12) 0.0187(3) Uani 1 1 d . . . . .
H00D H 0.919009 0.446261 0.177450 0.022 Uiso 1 1 calc R U . . .
C00E C 0.75236(19) 0.46493(6) 0.70738(11) 0.0171(3) Uani 1 1 d . . . . .
C00F C 0.73210(18) 0.43534(6) 0.27080(11) 0.0151(3) Uani 1 1 d . . . . .
C00G C 0.62652(19) 0.71848(6) 0.50903(11) 0.0174(3) Uani 1 1 d . . . . .
C00H C 0.57307(19) 0.33716(6) 0.24354(12) 0.0208(3) Uani 1 1 d . . . . .
H00H H 0.485161 0.310062 0.259224 0.025 Uiso 1 1 calc R U . . .
C00I C 0.77581(17) 0.57017(6) 0.48220(11) 0.0141(3) Uani 1 1 d . . . . .
C00J C 0.6373(2) 0.77084(6) 0.57814(12) 0.0193(3) Uani 1 1 d . . . . .
C00K C 0.4522(2) 0.70215(7) 0.44081(12) 0.0220(3) Uani 1 1 d . . . . .
H00K H 0.443730 0.667827 0.396304 0.026 Uiso 1 1 calc R U . . .
C00L C 0.8065(2) 0.36174(7) 0.14507(12) 0.0229(3) Uani 1 1 d . . . . .
H00L H 0.875945 0.350602 0.095746 0.027 Uiso 1 1 calc R U . . .
C00M C 0.6752(2) 0.32091(7) 0.16896(12) 0.0223(3) Uani 1 1 d . . . . .
H00M H 0.656234 0.282809 0.134898 0.027 Uiso 1 1 calc R U . . .
C00N C 0.9595(2) 0.70105(7) 0.58243(12) 0.0221(3) Uani 1 1 d . . . . .
H00N H 1.066785 0.677706 0.585660 0.027 Uiso 1 1 calc R U . . .
C00O C 0.9686(2) 0.75374(7) 0.64896(12) 0.0239(3) Uani 1 1 d . . . . .
H00O H 1.082008 0.765316 0.694496 0.029 Uiso 1 1 calc R U . . .
C00P C 0.8110(2) 0.78750(6) 0.64622(12) 0.0227(3) Uani 1 1 d . . . . .
H00P H 0.818241 0.822090 0.690011 0.027 Uiso 1 1 calc R U . . .
C00Q C 0.7237(2) 0.48032(7) 0.88811(11) 0.0224(3) Uani 1 1 d . . . . .
H00B H 0.832304 0.455291 0.919419 0.027 Uiso 1 1 calc R U . . .
H00E H 0.612382 0.454933 0.878696 0.027 Uiso 1 1 calc R U . . .
C00R C 0.4710(2) 0.80513(7) 0.57524(13) 0.0240(3) Uani 1 1 d . . . . .
H00R H 0.475389 0.839051 0.620279 0.029 Uiso 1 1 calc R U . . .
C00S C 0.2947(2) 0.73673(7) 0.43974(14) 0.0271(3) Uani 1 1 d . . . . .
H00S H 0.180591 0.725734 0.394321 0.033 Uiso 1 1 calc R U . . .
C00T C 0.7114(2) 0.53420(7) 0.96035(12) 0.0268(3) Uani 1 1 d . . . . .
H00F H 0.602613 0.558264 0.928857 0.040 Uiso 1 1 calc R U . . .
H00G H 0.821626 0.559177 0.968228 0.040 Uiso 1 1 calc R U . . .
H00I H 0.702240 0.519520 1.030035 0.040 Uiso 1 1 calc R U . . .
C00U C 0.3057(2) 0.78877(7) 0.50722(14) 0.0283(4) Uani 1 1 d . . . . .
H00U H 0.198815 0.812132 0.505205 0.034 Uiso 1 1 calc R U . . .
H002 H 0.792(3) 0.5926(11) 0.2945(18) 0.055(7) Uiso 1 1 d . . . . .


_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 C00E 1.3425(16) . ?
O001 C00Q 1.4515(16) . ?
O002 C009 1.2826(16) . ?
O002 H002 1.24(2) . ?
O003 C005 1.2794(17) . ?
O003 H002 1.21(2) . ?
O004 C00E 1.2143(17) . ?
C005 C00B 1.4959(18) . ?
C005 C00I 1.4124(18) . ?
C006 H006 0.9300 . ?
C006 C008 1.4031(18) . ?
C006 C00I 1.4053(18) . ?
C007 C009 1.4153(18) . ?
C007 C00A 1.4085(18) . ?
C007 C00I 1.4719(17) . ?
C008 C00A 1.4000(18) . ?
C008 C00E 1.4645(18) . ?
C009 C00F 1.4842(18) . ?
C00A H00A 0.9300 . ?
C00B C00G 1.4306(19) . ?
C00B C00N 1.368(2) . ?
C00C H00C 0.9300 . ?
C00C C00F 1.3954(18) . ?
C00C C00H 1.3898(19) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.4005(19) . ?
C00D C00L 1.3855(19) . ?
C00G C00J 1.4294(19) . ?
C00G C00K 1.412(2) . ?
C00H H00H 0.9300 . ?
C00H C00M 1.388(2) . ?
C00J C00P 1.409(2) . ?
C00J C00R 1.4237(19) . ?
C00K H00K 0.9300 . ?
C00K C00S 1.377(2) . ?
C00L H00L 0.9300 . ?
C00L C00M 1.396(2) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00N C00O 1.417(2) . ?
C00O H00O 0.9300 . ?
C00O C00P 1.364(2) . ?
C00P H00P 0.9300 . ?
C00Q H00B 0.9700 . ?
C00Q H00E 0.9700 . ?
C00Q C00T 1.505(2) . ?
C00R H00R 0.9300 . ?
C00R C00U 1.361(2) . ?
C00S H00S 0.9300 . ?
C00S C00U 1.411(2) . ?
C00T H00F 0.9600 . ?
C00T H00G 0.9600 . ?
C00T H00I 0.9600 . ?
C00U H00U 0.9300 . ?

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
C00E O001 C00Q 116.99(11) . . ?
C009 O002 H002 112.9(11) . . ?
C005 O003 H002 109.3(11) . . ?
O003 C005 C00B 116.90(12) . . ?
O003 C005 C00I 123.89(13) . . ?
C00I C005 C00B 119.20(12) . . ?
C008 C006 H006 125.6 . . ?
C008 C006 C00I 108.72(12) . . ?
C00I C006 H006 125.6 . . ?
C009 C007 C00I 127.35(12) . . ?
C00A C007 C009 126.37(12) . . ?
C00A C007 C00I 106.26(11) . . ?
C006 C008 C00E 126.39(12) . . ?
C00A C008 C006 108.77(12) . . ?
C00A C008 C00E 124.83(12) . . ?
O002 C009 C007 122.21(12) . . ?
O002 C009 C00F 114.93(12) . . ?
C007 C009 C00F 122.86(12) . . ?
C007 C00A H00A 125.4 . . ?
C008 C00A C007 109.17(11) . . ?
C008 C00A H00A 125.4 . . ?
C00G C00B C005 119.32(12) . . ?
C00N C00B C005 119.97(12) . . ?
C00N C00B C00G 120.70(13) . . ?
C00F C00C H00C 119.7 . . ?
C00H C00C H00C 119.7 . . ?
C00H C00C C00F 120.52(13) . . ?
C00F C00D H00D 119.9 . . ?
C00L C00D H00D 119.9 . . ?
C00L C00D C00F 120.22(13) . . ?
O001 C00E C008 111.83(11) . . ?
O004 C00E O001 123.41(13) . . ?
O004 C00E C008 124.77(13) . . ?
C00C C00F C009 122.25(12) . . ?
C00C C00F C00D 119.21(12) . . ?
C00D C00F C009 118.45(12) . . ?
C00J C00G C00B 117.98(13) . . ?
C00K C00G C00B 122.76(13) . . ?
C00K C00G C00J 119.26(13) . . ?
C00C C00H H00H 120.0 . . ?
C00M C00H C00C 119.91(13) . . ?
C00M C00H H00H 120.0 . . ?
C005 C00I C007 130.33(12) . . ?
C006 C00I C005 122.61(12) . . ?
C006 C00I C007 107.06(11) . . ?
C00P C00J C00G 119.55(13) . . ?
C00P C00J C00R 121.83(13) . . ?
C00R C00J C00G 118.62(13) . . ?
C00G C00K H00K 119.8 . . ?
C00S C00K C00G 120.41(14) . . ?
C00S C00K H00K 119.8 . . ?
C00D C00L H00L 119.9 . . ?
C00D C00L C00M 120.11(13) . . ?
C00M C00L H00L 119.9 . . ?
C00H C00M C00L 120.01(13) . . ?
C00H C00M H00M 120.0 . . ?
C00L C00M H00M 120.0 . . ?
C00B C00N H00N 119.7 . . ?
C00B C00N C00O 120.63(13) . . ?
C00O C00N H00N 119.7 . . ?
C00N C00O H00O 120.0 . . ?
C00P C00O C00N 120.01(14) . . ?
C00P C00O H00O 120.0 . . ?
C00J C00P H00P 119.4 . . ?
C00O C00P C00J 121.10(13) . . ?
C00O C00P H00P 119.4 . . ?
O001 C00Q H00B 110.4 . . ?
O001 C00Q H00E 110.4 . . ?
O001 C00Q C00T 106.83(12) . . ?
H00B C00Q H00E 108.6 . . ?
C00T C00Q H00B 110.4 . . ?
C00T C00Q H00E 110.4 . . ?
C00J C00R H00R 119.7 . . ?
C00U C00R C00J 120.68(14) . . ?
C00U C00R H00R 119.7 . . ?
C00K C00S H00S 119.8 . . ?
C00K C00S C00U 120.33(14) . . ?
C00U C00S H00S 119.8 . . ?
C00Q C00T H00F 109.5 . . ?
C00Q C00T H00G 109.5 . . ?
C00Q C00T H00I 109.5 . . ?
H00F C00T H00G 109.5 . . ?
H00F C00T H00I 109.5 . . ?
H00G C00T H00I 109.5 . . ?
C00R C00U C00S 120.68(14) . . ?
C00R C00U H00U 119.7 . . ?
C00S C00U H00U 119.7 . . ?

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 C00F C00C -139.54(13) . . . . ?
O002 C009 C00F C00D 37.04(18) . . . . ?
O003 C005 C00B C00G 80.76(17) . . . . ?
O003 C005 C00B C00N -98.41(16) . . . . ?
O003 C005 C00I C006 177.91(13) . . . . ?
O003 C005 C00I C007 -2.0(2) . . . . ?
C005 C00B C00G C00J -178.83(12) . . . . ?
C005 C00B C00G C00K 2.1(2) . . . . ?
C005 C00B C00N C00O 177.62(13) . . . . ?
C006 C008 C00A C007 -1.00(15) . . . . ?
C006 C008 C00E O001 5.57(18) . . . . ?
C006 C008 C00E O004 -174.81(14) . . . . ?
C007 C009 C00F C00C 40.99(19) . . . . ?
C007 C009 C00F C00D -142.42(13) . . . . ?
C008 C006 C00I C005 -179.44(12) . . . . ?
C008 C006 C00I C007 0.52(14) . . . . ?
C009 C007 C00A C008 179.88(12) . . . . ?
C009 C007 C00I C005 0.3(2) . . . . ?
C009 C007 C00I C006 -179.68(12) . . . . ?
C00A C007 C009 O002 -173.38(12) . . . . ?
C00A C007 C009 C00F 6.0(2) . . . . ?
C00A C007 C00I C005 178.85(13) . . . . ?
C00A C007 C00I C006 -1.11(14) . . . . ?
C00A C008 C00E O001 -173.11(12) . . . . ?
C00A C008 C00E O004 6.5(2) . . . . ?
C00B C005 C00I C006 -2.2(2) . . . . ?
C00B C005 C00I C007 177.86(12) . . . . ?
C00B C00G C00J C00P 1.1(2) . . . . ?
C00B C00G C00J C00R -179.48(12) . . . . ?
C00B C00G C00K C00S 179.90(14) . . . . ?
C00B C00N C00O C00P 1.3(2) . . . . ?
C00C C00H C00M C00L -0.3(2) . . . . ?
C00D C00L C00M C00H -0.8(2) . . . . ?
C00E O001 C00Q C00T -179.95(11) . . . . ?
C00E C008 C00A C007 177.87(12) . . . . ?
C00F C00C C00H C00M 0.8(2) . . . . ?
C00F C00D C00L C00M 1.4(2) . . . . ?
C00G C00B C00N C00O -1.5(2) . . . . ?
C00G C00J C00P C00O -1.4(2) . . . . ?
C00G C00J C00R C00U -0.7(2) . . . . ?
C00G C00K C00S C00U -0.3(2) . . . . ?
C00H C00C C00F C009 176.31(12) . . . . ?
C00H C00C C00F C00D -0.3(2) . . . . ?
C00I C005 C00B C00G -99.14(15) . . . . ?
C00I C005 C00B C00N 81.69(17) . . . . ?
C00I C006 C008 C00A 0.28(14) . . . . ?
C00I C006 C008 C00E -178.57(12) . . . . ?
C00I C007 C009 O002 4.9(2) . . . . ?
C00I C007 C009 C00F -175.66(12) . . . . ?
C00I C007 C00A C008 1.29(14) . . . . ?
C00J C00G C00K C00S 0.9(2) . . . . ?
C00J C00R C00U C00S 1.3(2) . . . . ?
C00K C00G C00J C00P -179.81(13) . . . . ?
C00K C00G C00J C00R -0.4(2) . . . . ?
C00K C00S C00U C00R -0.8(2) . . . . ?
C00L C00D C00F C009 -177.55(13) . . . . ?
C00L C00D C00F C00C -0.9(2) . . . . ?
C00N C00B C00G C00J 0.3(2) . . . . ?
C00N C00B C00G C00K -178.72(14) . . . . ?
C00N C00O C00P C00J 0.2(2) . . . . ?
C00P C00J C00R C00U 178.71(15) . . . . ?
C00Q O001 C00E O004 -1.36(19) . . . . ?
C00Q O001 C00E C008 178.28(11) . . . . ?
C00R C00J C00P C00O 179.24(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
