# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_mo_gp_a5_9r_0ma
_database_code_depnum_ccdc_archive 'CCDC 2376512'
loop_
_audit_author_name
_audit_author_address
'Anagha Varma A'
;IISER Tirupati
India
;
_audit_update_record             
;
2024-08-08 deposited with the CCDC.	2025-04-01 downloaded from the CCDC.
;
_audit_creation_date             2024-08-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H18 O5'
_chemical_formula_sum            'C15 H18 O5'
_chemical_formula_weight         278.29
_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 0.0033 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      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   15.9986(7)
_cell_length_b                   28.8588(12)
_cell_length_c                   12.5342(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5787.0(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9751
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.28
_cell_measurement_theta_min      2.82
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7098
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1024 before and 0.0571 after correction.
The Ratio of minimum to maximum transmission is 0.9519.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2368
_exptl_crystal_size_max          0.9
_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  0.0394
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            57843
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_min         2.823
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3528
_reflns_number_total             3594
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3594
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.076
_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)+(0.0548P)²+2.6822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0834
_refine_ls_wR_factor_ref         0.0838
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.0(8)
 0.0(8)
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:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C4(H4)
3.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C)
;
_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
O5 O 0.44012(8) 0.76548(5) 0.18113(11) 0.0325(3) Uani 1 1 d . . . . .
O1 O 0.73447(7) 0.68384(4) 0.48361(10) 0.0274(3) Uani 1 1 d . . . . .
O4 O 0.42044(8) 0.61580(4) 0.68115(10) 0.0254(3) Uani 1 1 d . . . . .
O3 O 0.50651(9) 0.56957(4) 0.58563(11) 0.0348(3) Uani 1 1 d . . . . .
O2 O 0.61756(7) 0.64100(4) 0.48422(10) 0.0238(2) Uani 1 1 d . . . . .
C10 C 0.46896(10) 0.60516(6) 0.59788(13) 0.0230(3) Uani 1 1 d . . . . .
C5 C 0.49323(10) 0.74404(5) 0.24917(12) 0.0215(3) Uani 1 1 d . . . . .
C3 C 0.62985(9) 0.74876(6) 0.33123(13) 0.0225(3) Uani 1 1 d . . . . .
H3 H 0.681375 0.764338 0.342773 0.027 Uiso 1 1 calc R U . . .
C9 C 0.46863(10) 0.64539(5) 0.52025(13) 0.0229(3) Uani 1 1 d . . . . .
H9A H 0.477192 0.674531 0.560460 0.027 Uiso 1 1 calc R U . . .
H9B H 0.413101 0.647124 0.485626 0.027 Uiso 1 1 calc R U . . .
C2 C 0.61279(9) 0.70635(5) 0.38034(11) 0.0197(3) Uani 1 1 d . . . . .
C7 C 0.53692(10) 0.68438(5) 0.36571(12) 0.0190(3) Uani 1 1 d . . . . .
C6 C 0.47514(9) 0.70227(5) 0.30060(12) 0.0200(3) Uani 1 1 d . . . . .
H6 H 0.423075 0.686974 0.291287 0.024 Uiso 1 1 calc R U . . .
C4 C 0.56952(10) 0.76719(5) 0.26562(13) 0.0227(3) Uani 1 1 d . . . . .
H4 H 0.579494 0.795938 0.230948 0.027 Uiso 1 1 calc R U . . .
C8 C 0.53520(10) 0.64166(5) 0.43460(12) 0.0206(3) Uani 1 1 d . . . . .
H8 H 0.526429 0.613291 0.390187 0.025 Uiso 1 1 calc R U . . .
C12 C 0.48710(13) 0.57067(7) 0.82378(16) 0.0369(4) Uani 1 1 d . . . . .
H12A H 0.522348 0.552539 0.775344 0.055 Uiso 1 1 calc R U . . .
H12B H 0.475654 0.552541 0.888257 0.055 Uiso 1 1 calc R U . . .
H12C H 0.516104 0.599353 0.843318 0.055 Uiso 1 1 calc R U . . .
C1 C 0.66396(10) 0.67847(6) 0.45261(12) 0.0223(3) Uani 1 1 d . . . . .
C13 C 0.34857(16) 0.60988(7) 0.84240(17) 0.0422(5) Uani 1 1 d . . . . .
H13A H 0.376788 0.638502 0.864119 0.063 Uiso 1 1 calc R U . . .
H13B H 0.335636 0.591301 0.905731 0.063 Uiso 1 1 calc R U . . .
H13C H 0.296640 0.617552 0.804880 0.063 Uiso 1 1 calc R U . . .
C11 C 0.40536(11) 0.58240(6) 0.76871(12) 0.0254(3) Uani 1 1 d . . . . .
C14 C 0.36097(13) 0.53985(7) 0.72580(16) 0.0338(4) Uani 1 1 d . . . . .
H14A H 0.309822 0.549325 0.688714 0.051 Uiso 1 1 calc R U . . .
H14B H 0.346589 0.519202 0.785093 0.051 Uiso 1 1 calc R U . . .
H14C H 0.397816 0.523549 0.675888 0.051 Uiso 1 1 calc R U . . .
C15 C 0.36287(13) 0.74218(9) 0.15866(19) 0.0483(6) Uani 1 1 d . . . . .
H15A H 0.330660 0.760279 0.106828 0.072 Uiso 1 1 calc R U . . .
H15B H 0.330567 0.738937 0.224671 0.072 Uiso 1 1 calc R U . . .
H15C H 0.374621 0.711419 0.129144 0.072 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
O5 C5 1.3536(19) . ?
O5 C15 1.435(2) . ?
O1 C1 1.203(2) . ?
O4 C10 1.3365(19) . ?
O4 C11 1.4804(18) . ?
O3 C10 1.200(2) . ?
O2 C8 1.4573(19) . ?
O2 C1 1.370(2) . ?
C10 C9 1.515(2) . ?
C5 C6 1.397(2) . ?
C5 C4 1.407(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.397(2) . ?
C3 C4 1.375(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C8 1.516(2) . ?
C2 C7 1.382(2) . ?
C2 C1 1.462(2) . ?
C7 C6 1.382(2) . ?
C7 C8 1.505(2) . ?
C6 H6 0.9500 . ?
C4 H4 0.9500 . ?
C8 H8 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 C11 1.517(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C11 1.519(2) . ?
C11 C14 1.517(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C5 O5 C15 116.76(14) . . ?
C10 O4 C11 121.60(12) . . ?
C1 O2 C8 110.87(12) . . ?
O4 C10 C9 108.88(13) . . ?
O3 C10 O4 125.98(15) . . ?
O3 C10 C9 125.14(14) . . ?
O5 C5 C6 123.71(14) . . ?
O5 C5 C4 114.83(14) . . ?
C6 C5 C4 121.46(14) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C4 C3 C2 117.73(14) . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C10 C9 C8 113.46(12) . . ?
H9A C9 H9B 107.7 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C3 C2 C1 130.22(14) . . ?
C7 C2 C3 121.02(14) . . ?
C7 C2 C1 108.74(14) . . ?
C2 C7 C6 122.35(14) . . ?
C2 C7 C8 108.41(13) . . ?
C6 C7 C8 129.18(14) . . ?
C5 C6 H6 121.7 . . ?
C7 C6 C5 116.54(13) . . ?
C7 C6 H6 121.7 . . ?
C5 C4 H4 119.6 . . ?
C3 C4 C5 120.86(14) . . ?
C3 C4 H4 119.6 . . ?
O2 C8 C9 109.51(13) . . ?
O2 C8 C7 103.83(12) . . ?
O2 C8 H8 110.7 . . ?
C9 C8 H8 110.7 . . ?
C7 C8 C9 111.16(12) . . ?
C7 C8 H8 110.7 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
O1 C1 O2 121.09(14) . . ?
O1 C1 C2 130.83(16) . . ?
O2 C1 C2 108.07(13) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
O4 C11 C12 110.01(14) . . ?
O4 C11 C13 102.03(14) . . ?
O4 C11 C14 109.90(14) . . ?
C12 C11 C13 110.82(17) . . ?
C12 C11 C14 112.60(15) . . ?
C14 C11 C13 110.97(16) . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
O5 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
O5 C5 C6 C7 178.52(15) . . . . ?
O5 C5 C4 C3 -178.71(16) . . . . ?
O4 C10 C9 C8 167.85(14) . . . . ?
O3 C10 C9 C8 -12.5(2) . . . . ?
C10 O4 C11 C12 62.0(2) . . . . ?
C10 O4 C11 C13 179.65(17) . . . . ?
C10 O4 C11 C14 -62.5(2) . . . . ?
C10 C9 C8 O2 -60.92(16) . . . . ?
C10 C9 C8 C7 -175.06(13) . . . . ?
C3 C2 C7 C6 1.5(2) . . . . ?
C3 C2 C7 C8 -175.93(13) . . . . ?
C3 C2 C1 O1 -4.1(3) . . . . ?
C3 C2 C1 O2 176.41(15) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C2 C7 C6 C5 0.3(2) . . . . ?
C2 C7 C8 O2 -2.46(15) . . . . ?
C2 C7 C8 C9 115.19(14) . . . . ?
C7 C2 C1 O1 177.17(16) . . . . ?
C7 C2 C1 O2 -2.35(17) . . . . ?
C6 C5 C4 C3 1.6(2) . . . . ?
C6 C7 C8 O2 -179.70(15) . . . . ?
C6 C7 C8 C9 -62.1(2) . . . . ?
C4 C5 C6 C7 -1.8(2) . . . . ?
C4 C3 C2 C7 -1.8(2) . . . . ?
C4 C3 C2 C1 179.61(16) . . . . ?
C8 O2 C1 O1 -178.86(14) . . . . ?
C8 O2 C1 C2 0.72(17) . . . . ?
C8 C7 C6 C5 177.18(15) . . . . ?
C1 O2 C8 C9 -117.78(13) . . . . ?
C1 O2 C8 C7 1.01(16) . . . . ?
C1 C2 C7 C6 -179.57(14) . . . . ?
C1 C2 C7 C8 2.96(17) . . . . ?
C11 O4 C10 O3 -2.2(3) . . . . ?
C11 O4 C10 C9 177.38(13) . . . . ?
C15 O5 C5 C6 -2.7(3) . . . . ?
C15 O5 C5 C4 177.60(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.0(8)
2 0.0(8)

####################################################################### 
# 
# 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_mo_gp_a6_5_0m
_database_code_depnum_ccdc_archive 'CCDC 2376513'
loop_
_audit_author_name
_audit_author_address
'Anagha Varma A'
;IISER TIRUPATI
India
;
_audit_update_record             
;
2024-12-31 deposited with the CCDC.	2025-04-01 downloaded from the CCDC.
;
_audit_creation_date             2024-08-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 O4'
_chemical_formula_sum            'C16 H14 O4'
_chemical_formula_weight         270.27
_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 0.0033 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.7983(2)
_cell_length_b                   12.3215(6)
_cell_length_c                   22.0080(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1301.16(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9830
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0884 before and 0.0575 after correction.
The Ratio of minimum to maximum transmission is 0.8660.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            31758
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.313
_diffrn_reflns_theta_min         2.482
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3077
_reflns_number_total             3232
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.434
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.1(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.034
_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)+(0.0521P)²+0.3334P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0932
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.10795
 -0.10795
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C8(H8), C6(H6), C3(H3), C10(H10)
2.d Idealised Me refined as rotating group:
 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
O4 O 0.8074(3) 0.62018(11) 0.53958(6) 0.0283(3) Uani 1 1 d . . . . .
O3 O 1.1407(3) 0.54529(11) 0.59661(6) 0.0301(3) Uani 1 1 d . . . . .
O2 O 1.0643(3) 0.74084(10) 0.69032(6) 0.0268(3) Uani 1 1 d . . . . .
O1 O 1.1228(3) 0.90666(11) 0.73007(6) 0.0325(3) Uani 1 1 d . . . . .
C4 C 0.4751(4) 0.77141(14) 0.85664(8) 0.0213(3) Uani 1 1 d . . . . .
C14 C 0.9203(4) 0.59030(14) 0.59235(8) 0.0251(4) Uani 1 1 d . . . . .
C5 C 0.3487(4) 0.81780(14) 0.90885(8) 0.0242(4) Uani 1 1 d . . . . .
H5 H 0.405462 0.887586 0.922403 0.029 Uiso 1 1 calc R U . . .
C9 C 0.3925(4) 0.66517(14) 0.83768(8) 0.0215(3) Uani 1 1 d . . . . .
C7 C 0.0625(4) 0.65830(16) 0.92081(8) 0.0271(4) Uani 1 1 d . . . . .
H7 H -0.078277 0.620821 0.942736 0.033 Uiso 1 1 calc R U . . .
C8 C 0.1826(4) 0.61032(14) 0.87109(8) 0.0246(4) Uani 1 1 d . . . . .
H8 H 0.124927 0.539835 0.858930 0.029 Uiso 1 1 calc R U . . .
C6 C 0.1459(4) 0.76290(16) 0.93978(8) 0.0271(4) Uani 1 1 d . . . . .
H6 H 0.060519 0.795273 0.974250 0.033 Uiso 1 1 calc R U . . .
C2 C 0.7953(4) 0.77898(14) 0.77408(8) 0.0230(3) Uani 1 1 d . . . . .
C1 C 1.0092(4) 0.82003(15) 0.73216(8) 0.0261(4) Uani 1 1 d . . . . .
C3 C 0.6809(4) 0.82828(14) 0.82347(8) 0.0222(3) Uani 1 1 d . . . . .
H3 H 0.737697 0.899026 0.835344 0.027 Uiso 1 1 calc R U . . .
C10 C 0.5218(4) 0.61603(14) 0.78662(8) 0.0230(4) Uani 1 1 d . . . . .
H10 H 0.470771 0.545021 0.774003 0.028 Uiso 1 1 calc R U . . .
C11 C 0.7216(4) 0.67328(14) 0.75598(8) 0.0228(3) Uani 1 1 d . . . . .
C15 C 0.9694(4) 0.59285(17) 0.48573(8) 0.0300(4) Uani 1 1 d . . . . .
H15A H 0.999500 0.513461 0.483525 0.036 Uiso 1 1 calc R U . . .
H15B H 1.153327 0.629147 0.487115 0.036 Uiso 1 1 calc R U . . .
C12 C 0.8971(4) 0.64357(14) 0.70200(8) 0.0237(4) Uani 1 1 d . . . . .
H12 H 1.021439 0.581078 0.712286 0.028 Uiso 1 1 calc R U . . .
C16 C 0.8070(5) 0.63096(19) 0.43151(9) 0.0369(5) Uani 1 1 d . . . . .
H16A H 0.905759 0.610443 0.394264 0.055 Uiso 1 1 calc R U . . .
H16B H 0.787174 0.710069 0.433098 0.055 Uiso 1 1 calc R U . . .
H16C H 0.622000 0.597260 0.431756 0.055 Uiso 1 1 calc R U . . .
C13 C 0.7312(4) 0.61842(16) 0.64518(9) 0.0272(4) Uani 1 1 d . . . . .
H13A H 0.615770 0.682136 0.634322 0.033 Uiso 1 1 calc R U . . .
H13B H 0.604362 0.556729 0.653307 0.033 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
O4 C14 1.333(2) . ?
O4 C15 1.457(2) . ?
O3 C14 1.198(2) . ?
O2 C1 1.367(2) . ?
O2 C12 1.465(2) . ?
O1 C1 1.199(2) . ?
C4 C5 1.420(2) . ?
C4 C9 1.430(2) . ?
C4 C3 1.414(3) . ?
C14 C13 1.515(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.367(3) . ?
C9 C8 1.418(3) . ?
C9 C10 1.419(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.371(3) . ?
C7 C6 1.413(3) . ?
C8 H8 0.9500 . ?
C6 H6 0.9500 . ?
C2 C1 1.470(3) . ?
C2 C3 1.361(3) . ?
C2 C11 1.407(2) . ?
C3 H3 0.9500 . ?
C10 H10 0.9500 . ?
C10 C11 1.368(3) . ?
C11 C12 1.502(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.500(3) . ?
C12 H12 1.0000 . ?
C12 C13 1.514(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 O4 C15 115.34(15) . . ?
C1 O2 C12 111.08(14) . . ?
C5 C4 C9 119.09(16) . . ?
C3 C4 C5 121.12(16) . . ?
C3 C4 C9 119.78(16) . . ?
O4 C14 C13 111.22(16) . . ?
O3 C14 O4 123.68(18) . . ?
O3 C14 C13 125.08(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.54(17) . . ?
C6 C5 H5 119.7 . . ?
C8 C9 C4 118.80(16) . . ?
C8 C9 C10 121.17(16) . . ?
C10 C9 C4 120.03(16) . . ?
C8 C7 H7 119.7 . . ?
C8 C7 C6 120.68(18) . . ?
C6 C7 H7 119.7 . . ?
C9 C8 H8 119.8 . . ?
C7 C8 C9 120.46(17) . . ?
C7 C8 H8 119.8 . . ?
C5 C6 C7 120.41(18) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C3 C2 C1 129.02(17) . . ?
C3 C2 C11 122.53(17) . . ?
C11 C2 C1 108.44(16) . . ?
O2 C1 C2 108.19(15) . . ?
O1 C1 O2 121.42(18) . . ?
O1 C1 C2 130.36(18) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 C4 118.23(16) . . ?
C2 C3 H3 120.9 . . ?
C9 C10 H10 120.8 . . ?
C11 C10 C9 118.46(16) . . ?
C11 C10 H10 120.8 . . ?
C2 C11 C12 107.98(16) . . ?
C10 C11 C2 120.93(17) . . ?
C10 C11 C12 131.10(16) . . ?
O4 C15 H15A 110.3 . . ?
O4 C15 H15B 110.3 . . ?
O4 C15 C16 107.31(17) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.3 . . ?
C16 C15 H15B 110.3 . . ?
O2 C12 C11 104.27(14) . . ?
O2 C12 H12 110.1 . . ?
O2 C12 C13 108.09(14) . . ?
C11 C12 H12 110.1 . . ?
C11 C12 C13 114.10(16) . . ?
C13 C12 H12 110.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C12 C13 C14 111.44(16) . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?

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 C14 C13 C12 -149.02(15) . . . . ?
O3 C14 C13 C12 32.3(3) . . . . ?
O2 C12 C13 C14 63.92(19) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C4 C9 C8 C7 -0.3(3) . . . . ?
C4 C9 C10 C11 -1.0(3) . . . . ?
C14 O4 C15 C16 179.02(17) . . . . ?
C5 C4 C9 C8 1.2(2) . . . . ?
C5 C4 C9 C10 -178.24(16) . . . . ?
C5 C4 C3 C2 179.56(17) . . . . ?
C9 C4 C5 C6 -1.6(3) . . . . ?
C9 C4 C3 C2 -0.2(3) . . . . ?
C9 C10 C11 C2 -0.8(3) . . . . ?
C9 C10 C11 C12 178.73(17) . . . . ?
C8 C9 C10 C11 179.58(17) . . . . ?
C8 C7 C6 C5 -0.2(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C2 C11 C12 O2 -1.93(19) . . . . ?
C2 C11 C12 C13 -119.63(17) . . . . ?
C1 O2 C12 C11 1.68(19) . . . . ?
C1 O2 C12 C13 123.43(16) . . . . ?
C1 C2 C3 C4 179.67(18) . . . . ?
C1 C2 C11 C10 -178.86(17) . . . . ?
C1 C2 C11 C12 1.5(2) . . . . ?
C3 C4 C5 C6 178.64(17) . . . . ?
C3 C4 C9 C8 -179.04(16) . . . . ?
C3 C4 C9 C10 1.6(2) . . . . ?
C3 C2 C1 O2 178.36(18) . . . . ?
C3 C2 C1 O1 -3.5(4) . . . . ?
C3 C2 C11 C10 2.2(3) . . . . ?
C3 C2 C11 C12 -177.41(17) . . . . ?
C10 C9 C8 C7 179.09(17) . . . . ?
C10 C11 C12 O2 178.51(19) . . . . ?
C10 C11 C12 C13 60.8(3) . . . . ?
C11 C2 C1 O2 -0.5(2) . . . . ?
C11 C2 C1 O1 177.7(2) . . . . ?
C11 C2 C3 C4 -1.6(3) . . . . ?
C11 C12 C13 C14 179.40(15) . . . . ?
C15 O4 C14 O3 0.9(3) . . . . ?
C15 O4 C14 C13 -177.81(15) . . . . ?
C12 O2 C1 O1 -179.14(18) . . . . ?
C12 O2 C1 C2 -0.8(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.10795
2 -0.10795

