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

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

data_MAF04a
_database_code_depnum_ccdc_archive 'CCDC 2372678'
loop_
_audit_author_name
_audit_author_address
'Lauren Connor'
;Novartis
Switzerland
;
_audit_update_record             
;
2024-07-22 deposited with the CCDC.	2025-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            SADZIDO1-007-EXP056-001
_chemical_source_common          DCM/HEP
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H21 N1 O4'
_chemical_formula_sum            'C12 H21 N O4'
_chemical_formula_weight         243.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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.
;

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                   6.8875(2)
_cell_length_b                   10.3983(3)
_cell_length_c                   18.8853(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1352.53(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8356
_cell_measurement_theta_min      4.683
_cell_measurement_theta_max      67.9855

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.734
_shelx_estimated_absorpt_T_min   0.753
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6681
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 absolute structure:  C8S, C10S, Flack x = 0.06(9)[942 quotients]
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_source                   'MicroStar rotating anode'
_diffrn_measurement_device_type  'Bruker SMART6000 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16097
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.683
_diffrn_reflns_theta_max         68.367
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2460
_reflns_number_gt                2328
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.988
_reflns_Friedel_fraction_full    0.994

_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²+0.1239P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 942 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2460
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0704
_refine_ls_wR_factor_gt          0.0694
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44891(19) 0.77361(11) 0.53489(6) 0.0268(3) Uani 1 1 d . . . . .
O2 O 0.81805(17) 0.55595(11) 0.61467(6) 0.0227(3) Uani 1 1 d . . . . .
O3 O 0.45868(19) 0.71622(12) 0.42044(6) 0.0234(3) Uani 1 1 d . . . . .
H3 H 0.405(3) 0.793(2) 0.4138(2) 0.035 Uiso 1 1 calc R U . . .
N4 N 0.5079(2) 0.52200(14) 0.57728(7) 0.0204(3) Uani 1 1 d . . . . .
O5 O 0.58722(17) 0.47867(12) 0.68913(6) 0.0249(3) Uani 1 1 d . . . . .
C6 C 0.6494(2) 0.52310(15) 0.62665(8) 0.0189(3) Uani 1 1 d . . . . .
C7 C 0.3012(3) 0.49955(18) 0.59236(9) 0.0245(4) Uani 1 1 d . . . . .
H7A H 0.228789 0.581296 0.587489 0.029 Uiso 1 1 calc R U . . .
H7B H 0.286346 0.469068 0.641724 0.029 Uiso 1 1 calc R U . . .
C8 C 0.5531(2) 0.55876(16) 0.50454(8) 0.0194(4) Uani 1 1 d . . . . .
H8 H 0.697639 0.559416 0.499418 0.023 Uiso 1 1 calc R U . . .
C9 C 0.4796(2) 0.69469(17) 0.48938(9) 0.0200(4) Uani 1 1 d . . . . .
C10 C 0.2561(3) 0.43331(17) 0.46439(10) 0.0251(4) Uani 1 1 d . . . . .
H10 H 0.184586 0.514279 0.452723 0.030 Uiso 1 1 calc R U . . .
C11 C 0.7129(3) 0.48435(17) 0.75301(8) 0.0244(4) Uani 1 1 d . . . . .
C12 C 0.2175(3) 0.40037(17) 0.54196(10) 0.0268(4) Uani 1 1 d . . . . .
H12A H 0.075609 0.394207 0.549662 0.032 Uiso 1 1 calc R U . . .
H12B H 0.274893 0.315285 0.552694 0.032 Uiso 1 1 calc R U . . .
C13 C 0.4726(3) 0.45741(15) 0.45381(9) 0.0226(4) Uani 1 1 d . . . . .
H13A H 0.495207 0.485909 0.404475 0.027 Uiso 1 1 calc R U . . .
H13B H 0.543894 0.375763 0.460903 0.027 Uiso 1 1 calc R U . . .
C14 C 0.5849(3) 0.4220(2) 0.80868(10) 0.0358(5) Uani 1 1 d . . . . .
H14A H 0.460110 0.467162 0.810805 0.054 Uiso 1 1 calc R U . . .
H14B H 0.648952 0.426937 0.854931 0.054 Uiso 1 1 calc R U . . .
H14C H 0.562851 0.331678 0.796247 0.054 Uiso 1 1 calc R U . . .
C15 C 0.1855(3) 0.3278(2) 0.41487(11) 0.0370(5) Uani 1 1 d . . . . .
H15A H 0.218866 0.350184 0.365951 0.055 Uiso 1 1 calc R U . . .
H15B H 0.044303 0.319029 0.419182 0.055 Uiso 1 1 calc R U . . .
H15C H 0.247766 0.246284 0.427570 0.055 Uiso 1 1 calc R U . . .
C16 C 0.8960(3) 0.4064(2) 0.74257(10) 0.0370(5) Uani 1 1 d . . . . .
H16A H 0.862496 0.321898 0.723051 0.055 Uiso 1 1 calc R U . . .
H16B H 0.961600 0.395194 0.788211 0.055 Uiso 1 1 calc R U . . .
H16C H 0.982555 0.451413 0.709698 0.055 Uiso 1 1 calc R U . . .
C17 C 0.7514(3) 0.62439(18) 0.77054(10) 0.0338(5) Uani 1 1 d . . . . .
H17A H 0.829575 0.663261 0.732842 0.051 Uiso 1 1 calc R U . . .
H17B H 0.821760 0.630045 0.815535 0.051 Uiso 1 1 calc R U . . .
H17C H 0.627650 0.670339 0.774584 0.051 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0364(7) 0.0230(6) 0.0210(6) -0.0044(5) -0.0023(6) 0.0027(5)
O2 0.0211(6) 0.0250(6) 0.0220(6) 0.0060(5) -0.0007(5) -0.0022(5)
O3 0.0309(7) 0.0220(6) 0.0173(6) 0.0025(5) -0.0010(5) 0.0039(5)
N4 0.0190(7) 0.0262(7) 0.0160(7) 0.0035(6) 0.0012(5) -0.0008(6)
O5 0.0275(6) 0.0315(7) 0.0159(6) 0.0052(5) -0.0006(5) -0.0057(5)
C6 0.0230(9) 0.0163(7) 0.0173(8) 0.0022(6) -0.0001(6) 0.0012(7)
C7 0.0198(8) 0.0313(9) 0.0224(9) 0.0034(7) 0.0029(7) -0.0005(8)
C8 0.0202(8) 0.0219(8) 0.0159(8) 0.0026(6) 0.0009(6) 0.0005(7)
C9 0.0193(8) 0.0225(8) 0.0182(8) 0.0008(6) 0.0000(7) -0.0025(7)
C10 0.0283(9) 0.0201(8) 0.0269(9) -0.0003(7) -0.0056(8) -0.0006(7)
C11 0.0313(10) 0.0259(9) 0.0161(8) 0.0036(7) -0.0019(7) -0.0007(8)
C12 0.0232(9) 0.0251(9) 0.0320(9) 0.0033(8) -0.0009(8) -0.0027(7)
C13 0.0297(9) 0.0187(8) 0.0193(8) 0.0002(7) 0.0006(7) 0.0028(7)
C14 0.0465(12) 0.0419(11) 0.0190(9) 0.0066(8) 0.0005(9) -0.0092(10)
C15 0.0457(13) 0.0287(10) 0.0364(11) -0.0039(8) -0.0091(9) -0.0073(9)
C16 0.0438(12) 0.0433(12) 0.0239(9) 0.0038(9) -0.0059(9) 0.0139(10)
C17 0.0491(13) 0.0277(9) 0.0246(9) 0.0029(8) -0.0090(9) -0.0036(9)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.207(2) . ?
O2 C6 1.232(2) . ?
O3 C9 1.329(2) . ?
O3 H3 0.89(3) . ?
N4 C6 1.349(2) . ?
N4 C8 1.460(2) . ?
N4 C7 1.470(2) . ?
O5 C6 1.3375(19) . ?
O5 C11 1.486(2) . ?
C7 C12 1.517(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C13 1.528(2) . ?
C8 C9 1.528(2) . ?
C8 H8 1.0000 . ?
C10 C15 1.521(3) . ?
C10 C13 1.525(3) . ?
C10 C12 1.528(3) . ?
C10 H10 1.0000 . ?
C11 C16 1.512(3) . ?
C11 C17 1.517(3) . ?
C11 C14 1.518(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C9 O3 H3 109.5 . . ?
C6 N4 C8 119.61(14) . . ?
C6 N4 C7 124.53(14) . . ?
C8 N4 C7 115.52(13) . . ?
C6 O5 C11 121.06(13) . . ?
O2 C6 O5 124.02(15) . . ?
O2 C6 N4 123.84(15) . . ?
O5 C6 N4 112.07(14) . . ?
N4 C7 C12 110.76(15) . . ?
N4 C7 H7A 109.5 . . ?
C12 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
C12 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N4 C8 C13 109.38(13) . . ?
N4 C8 C9 110.35(13) . . ?
C13 C8 C9 113.57(13) . . ?
N4 C8 H8 107.8 . . ?
C13 C8 H8 107.8 . . ?
C9 C8 H8 107.8 . . ?
O1 C9 O3 124.34(16) . . ?
O1 C9 C8 123.60(15) . . ?
O3 C9 C8 112.04(14) . . ?
C15 C10 C13 110.52(16) . . ?
C15 C10 C12 111.85(15) . . ?
C13 C10 C12 109.43(14) . . ?
C15 C10 H10 108.3 . . ?
C13 C10 H10 108.3 . . ?
C12 C10 H10 108.3 . . ?
O5 C11 C16 111.03(14) . . ?
O5 C11 C17 108.49(14) . . ?
C16 C11 C17 113.45(17) . . ?
O5 C11 C14 101.93(14) . . ?
C16 C11 C14 110.23(16) . . ?
C17 C11 C14 111.12(16) . . ?
C7 C12 C10 112.51(14) . . ?
C7 C12 H12A 109.1 . . ?
C10 C12 H12A 109.1 . . ?
C7 C12 H12B 109.1 . . ?
C10 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C10 C13 C8 112.71(14) . . ?
C10 C13 H13A 109.0 . . ?
C8 C13 H13A 109.0 . . ?
C10 C13 H13B 109.0 . . ?
C8 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C11 O5 C6 O2 9.5(2) . . . . ?
C11 O5 C6 N4 -173.42(14) . . . . ?
C8 N4 C6 O2 1.3(2) . . . . ?
C7 N4 C6 O2 -171.62(16) . . . . ?
C8 N4 C6 O5 -175.73(14) . . . . ?
C7 N4 C6 O5 11.3(2) . . . . ?
C6 N4 C7 C12 -131.77(17) . . . . ?
C8 N4 C7 C12 55.0(2) . . . . ?
C6 N4 C8 C13 130.94(15) . . . . ?
C7 N4 C8 C13 -55.49(19) . . . . ?
C6 N4 C8 C9 -103.43(17) . . . . ?
C7 N4 C8 C9 70.14(18) . . . . ?
N4 C8 C9 O1 22.4(2) . . . . ?
C13 C8 C9 O1 145.65(17) . . . . ?
N4 C8 C9 O3 -159.22(14) . . . . ?
C13 C8 C9 O3 -36.0(2) . . . . ?
C6 O5 C11 C16 -61.5(2) . . . . ?
C6 O5 C11 C17 63.8(2) . . . . ?
C6 O5 C11 C14 -178.86(15) . . . . ?
N4 C7 C12 C10 -52.5(2) . . . . ?
C15 C10 C12 C7 175.46(17) . . . . ?
C13 C10 C12 C7 52.64(19) . . . . ?
C15 C10 C13 C8 -177.57(14) . . . . ?
C12 C10 C13 C8 -53.97(17) . . . . ?
N4 C8 C13 C10 54.66(18) . . . . ?
C9 C8 C13 C10 -69.09(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O2 0.89 1.76 2.6439(17) 169.5 4_466 yes

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.038
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/HEP'
####################################################################### 
# 
# 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_MAF05a
_database_code_depnum_ccdc_archive 'CCDC 2372681'
loop_
_audit_author_name
_audit_author_address
'Lauren Connor'
;Novartis
Switzerland
;
_audit_update_record             
;
2024-07-24 deposited with the CCDC.	2025-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            SADZIDO1-007-EXP056-002
_chemical_source_common          DCM/HEP
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H21 N O4'
_chemical_formula_sum            'C12 H21 N O4'
_chemical_formula_weight         243.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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.
;

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                   6.8905(2)
_cell_length_b                   10.3980(3)
_cell_length_c                   18.8773(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1352.51(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8633
_cell_measurement_theta_min      4.685
_cell_measurement_theta_max      68.412

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.734
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6322
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 absolute structure: C8R, C10R, Flack x = 0.08(8) [921 quotients]
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_source                   'MicroStar rotating anode'
_diffrn_measurement_device_type  'Bruker SMART6000 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18014
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0485
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         4.685
_diffrn_reflns_theta_max         68.477
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2453
_reflns_number_gt                2313
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_max     0.981
_reflns_Friedel_fraction_full    0.990

_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.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2020)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+0.1612P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0091(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 921 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2453
_refine_ls_number_parameters     161
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0737
_refine_ls_wR_factor_gt          0.0723
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4487(2) 0.22645(12) 0.53484(6) 0.0273(3) Uani 1 1 d . . . . .
O2 O 0.81808(18) 0.44409(12) 0.61470(6) 0.0232(3) Uani 1 1 d . . . . .
O3 O 0.4585(2) 0.28387(13) 0.42039(6) 0.0239(3) Uani 1 1 d . . . . .
H3 H 0.402(4) 0.204(3) 0.4136(2) 0.036 Uiso 1 1 calc R U . . .
N4 N 0.5078(2) 0.47787(15) 0.57721(7) 0.0207(3) Uani 1 1 d . . . . .
O5 O 0.58714(18) 0.52133(13) 0.68921(6) 0.0255(3) Uani 1 1 d . . . . .
C6 C 0.6492(3) 0.47692(17) 0.62666(9) 0.0190(4) Uani 1 1 d . . . . .
C7 C 0.3014(3) 0.5003(2) 0.59239(9) 0.0247(4) Uani 1 1 d . . . . .
H7A H 0.286734 0.530687 0.641801 0.030 Uiso 1 1 calc R U . . .
H7B H 0.228995 0.418549 0.587523 0.030 Uiso 1 1 calc R U . . .
C8 C 0.5529(3) 0.44128(18) 0.50453(8) 0.0196(4) Uani 1 1 d . . . . .
H8 H 0.697302 0.440590 0.499405 0.024 Uiso 1 1 calc R U . . .
C9 C 0.4793(3) 0.30544(18) 0.48936(9) 0.0199(4) Uani 1 1 d . . . . .
C10 C 0.2560(3) 0.56653(19) 0.46436(10) 0.0251(4) Uani 1 1 d . . . . .
H10 H 0.184532 0.485579 0.452652 0.030 Uiso 1 1 calc R U . . .
C11 C 0.7129(3) 0.51562(19) 0.75304(9) 0.0249(4) Uani 1 1 d . . . . .
C12 C 0.2171(3) 0.59976(18) 0.54200(10) 0.0272(4) Uani 1 1 d . . . . .
H12A H 0.274262 0.684901 0.552729 0.033 Uiso 1 1 calc R U . . .
H12B H 0.075232 0.605727 0.549706 0.033 Uiso 1 1 calc R U . . .
C13 C 0.4724(3) 0.54261(17) 0.45382(9) 0.0231(4) Uani 1 1 d . . . . .
H13A H 0.543581 0.624300 0.460976 0.028 Uiso 1 1 calc R U . . .
H13B H 0.495201 0.514201 0.404458 0.028 Uiso 1 1 calc R U . . .
C14 C 0.5851(3) 0.5779(2) 0.80881(10) 0.0359(5) Uani 1 1 d . . . . .
H14A H 0.563368 0.668286 0.796482 0.054 Uiso 1 1 calc R U . . .
H14B H 0.649251 0.572697 0.855065 0.054 Uiso 1 1 calc R U . . .
H14C H 0.460326 0.532864 0.810907 0.054 Uiso 1 1 calc R U . . .
C15 C 0.1854(4) 0.6724(2) 0.41485(12) 0.0379(5) Uani 1 1 d . . . . .
H15A H 0.219241 0.650400 0.365905 0.057 Uiso 1 1 calc R U . . .
H15B H 0.247435 0.753966 0.427765 0.057 Uiso 1 1 calc R U . . .
H15C H 0.044283 0.681076 0.419037 0.057 Uiso 1 1 calc R U . . .
C16 C 0.8957(3) 0.5935(2) 0.74281(11) 0.0376(5) Uani 1 1 d . . . . .
H16A H 0.981588 0.549152 0.709429 0.056 Uiso 1 1 calc R U . . .
H16B H 0.961979 0.603513 0.788416 0.056 Uiso 1 1 calc R U . . .
H16C H 0.862165 0.678489 0.723965 0.056 Uiso 1 1 calc R U . . .
C17 C 0.7509(4) 0.3757(2) 0.77054(10) 0.0340(5) Uani 1 1 d . . . . .
H17A H 0.627105 0.330009 0.774874 0.051 Uiso 1 1 calc R U . . .
H17B H 0.821990 0.369980 0.815393 0.051 Uiso 1 1 calc R U . . .
H17C H 0.828274 0.336625 0.732664 0.051 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0361(8) 0.0239(7) 0.0220(6) 0.0039(6) -0.0027(6) -0.0030(6)
O2 0.0202(6) 0.0267(7) 0.0228(6) -0.0059(5) -0.0006(5) 0.0020(5)
O3 0.0305(7) 0.0232(7) 0.0180(6) -0.0025(5) -0.0007(6) -0.0036(6)
N4 0.0179(7) 0.0274(8) 0.0167(7) -0.0031(6) 0.0008(6) 0.0002(6)
O5 0.0272(7) 0.0334(7) 0.0158(6) -0.0056(5) -0.0008(5) 0.0057(6)
C6 0.0223(9) 0.0167(8) 0.0180(8) -0.0020(6) 0.0004(7) -0.0010(7)
C7 0.0195(9) 0.0323(10) 0.0224(9) -0.0037(8) 0.0022(7) 0.0009(8)
C8 0.0191(8) 0.0233(9) 0.0164(8) -0.0026(7) 0.0009(7) -0.0016(8)
C9 0.0184(8) 0.0239(9) 0.0176(8) -0.0002(7) -0.0002(7) 0.0024(7)
C10 0.0272(9) 0.0209(9) 0.0272(9) -0.0005(8) -0.0057(8) 0.0009(8)
C11 0.0307(10) 0.0280(10) 0.0159(8) -0.0037(7) -0.0036(8) 0.0005(8)
C12 0.0223(9) 0.0268(10) 0.0327(10) -0.0031(8) -0.0001(8) 0.0031(8)
C13 0.0283(9) 0.0204(9) 0.0205(8) 0.0007(7) 0.0003(8) -0.0038(8)
C14 0.0451(12) 0.0430(12) 0.0197(9) -0.0074(9) 0.0003(9) 0.0087(10)
C15 0.0437(13) 0.0309(11) 0.0392(11) 0.0041(9) -0.0085(10) 0.0075(10)
C16 0.0427(13) 0.0456(13) 0.0243(10) -0.0045(9) -0.0048(10) -0.0147(11)
C17 0.0490(14) 0.0291(10) 0.0239(9) -0.0023(8) -0.0096(9) 0.0036(10)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.207(2) . ?
O2 C6 1.234(2) . ?
O3 C9 1.329(2) . ?
O3 H3 0.92(3) . ?
N4 C6 1.349(2) . ?
N4 C8 1.457(2) . ?
N4 C7 1.469(2) . ?
O5 C6 1.338(2) . ?
O5 C11 1.485(2) . ?
C7 C12 1.520(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.528(3) . ?
C8 C13 1.528(2) . ?
C8 H8 1.0000 . ?
C10 C15 1.524(3) . ?
C10 C13 1.525(3) . ?
C10 C12 1.530(3) . ?
C10 H10 1.0000 . ?
C11 C16 1.510(3) . ?
C11 C17 1.515(3) . ?
C11 C14 1.517(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C9 O3 H3 109.5 . . ?
C6 N4 C8 119.70(14) . . ?
C6 N4 C7 124.40(14) . . ?
C8 N4 C7 115.57(13) . . ?
C6 O5 C11 121.06(14) . . ?
O2 C6 O5 123.93(16) . . ?
O2 C6 N4 123.82(15) . . ?
O5 C6 N4 112.18(15) . . ?
N4 C7 C12 110.85(15) . . ?
N4 C7 H7A 109.5 . . ?
C12 C7 H7A 109.5 . . ?
N4 C7 H7B 109.5 . . ?
C12 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N4 C8 C9 110.31(14) . . ?
N4 C8 C13 109.43(14) . . ?
C9 C8 C13 113.57(14) . . ?
N4 C8 H8 107.8 . . ?
C9 C8 H8 107.8 . . ?
C13 C8 H8 107.8 . . ?
O1 C9 O3 124.29(17) . . ?
O1 C9 C8 123.64(16) . . ?
O3 C9 C8 112.05(15) . . ?
C15 C10 C13 110.48(17) . . ?
C15 C10 C12 111.62(16) . . ?
C13 C10 C12 109.48(15) . . ?
C15 C10 H10 108.4 . . ?
C13 C10 H10 108.4 . . ?
C12 C10 H10 108.4 . . ?
O5 C11 C16 111.19(15) . . ?
O5 C11 C17 108.44(15) . . ?
C16 C11 C17 113.50(18) . . ?
O5 C11 C14 101.97(15) . . ?
C16 C11 C14 110.10(17) . . ?
C17 C11 C14 111.03(17) . . ?
C7 C12 C10 112.25(15) . . ?
C7 C12 H12A 109.2 . . ?
C10 C12 H12A 109.2 . . ?
C7 C12 H12B 109.2 . . ?
C10 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C10 C13 C8 112.67(15) . . ?
C10 C13 H13A 109.1 . . ?
C8 C13 H13A 109.1 . . ?
C10 C13 H13B 109.1 . . ?
C8 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C17 H17A 109.5 . . ?
C11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C11 O5 C6 O2 -9.5(3) . . . . ?
C11 O5 C6 N4 173.37(15) . . . . ?
C8 N4 C6 O2 -1.4(3) . . . . ?
C7 N4 C6 O2 171.65(18) . . . . ?
C8 N4 C6 O5 175.68(15) . . . . ?
C7 N4 C6 O5 -11.3(2) . . . . ?
C6 N4 C7 C12 131.67(18) . . . . ?
C8 N4 C7 C12 -55.0(2) . . . . ?
C6 N4 C8 C9 103.52(18) . . . . ?
C7 N4 C8 C9 -70.14(19) . . . . ?
C6 N4 C8 C13 -130.84(16) . . . . ?
C7 N4 C8 C13 55.5(2) . . . . ?
N4 C8 C9 O1 -22.4(2) . . . . ?
C13 C8 C9 O1 -145.69(18) . . . . ?
N4 C8 C9 O3 159.30(15) . . . . ?
C13 C8 C9 O3 36.0(2) . . . . ?
C6 O5 C11 C16 61.5(2) . . . . ?
C6 O5 C11 C17 -63.9(2) . . . . ?
C6 O5 C11 C14 178.87(16) . . . . ?
N4 C7 C12 C10 52.4(2) . . . . ?
C15 C10 C12 C7 -175.28(18) . . . . ?
C13 C10 C12 C7 -52.6(2) . . . . ?
C15 C10 C13 C8 177.45(15) . . . . ?
C12 C10 C13 C8 54.14(19) . . . . ?
N4 C8 C13 C10 -54.75(19) . . . . ?
C9 C8 C13 C10 68.99(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O2 0.92 1.73 2.6445(18) 169.1 4_456 yes

_refine_diff_density_max         0.162
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.045
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM/HEP'
