# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_dm-fbm
_audit_block_doi                 10.5517/ccdc.csd.cc2rgqxw
_database_code_depnum_ccdc_archive 'CCDC 2546399'
loop_
_audit_author_name
_audit_author_address
'Gerald Draeger'
;Leibniz University Hannover, Institute of organic Chemistry
Germany
;
_audit_update_record             
;
2026-04-15 deposited with the CCDC.	2026-06-02 downloaded from the CCDC.
;
_audit_creation_date             2025-02-21
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
draeger@oci.uni-hannover.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 F O4'
_chemical_formula_sum            'C18 H17 F O4'
_chemical_formula_weight         316.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H17FO4
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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.11690(10)
_cell_length_b                   14.9307(2)
_cell_length_c                   16.7379(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.073(2)
_cell_angle_gamma                90
_cell_volume                     1505.10(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6607
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      72.3060
_cell_measurement_theta_min      3.9800
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.609
_exptl_absorpt_coefficient_mu    0.889
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 9 3 0.0446
-3 5 -3 0.1953
-1 -9 -3 0.0446
0 1 -11 0.0377
-4 -1 2 0.2400
0 -1 11 0.0862
1 -1 0 0.3427
2 -1 -1 0.3646
_exptl_crystal_size_max          0.621
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.089
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.6476 9.0902 2.9762 -0.9381 -0.1080 0.3290
-3.0820 4.8737 -2.5993 -0.5320 -0.0612 -0.8445
-0.6476 -9.0902 -2.9762 0.9381 0.1080 -0.3290
0.1970 1.3964 -10.6651 -0.1000 0.8686 -0.4854
-3.9370 -1.2105 2.1585 0.0644 -0.5613 -0.8251
-0.1808 -1.3919 10.6601 0.0998 -0.8666 0.4890
1.0010 -1.0023 0.4985 0.1144 0.0511 0.2586
2.0007 -1.0050 -1.0024 0.1336 0.2665 0.4193

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10025
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.672
_diffrn_reflns_theta_min         3.995
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  37.00   0.50    2.75    --    0.00 -43.00-172.00  252
  2  ω    -38.00  89.00   0.50    2.75    --    0.00  77.00 149.00  254
  3  ω      7.00 107.00   0.50   11.02    --   96.30 -77.00  24.00  200
  4  ω     83.00 123.00   0.50   11.02    --   96.30  43.00 -20.00   80
  5  ω     46.00  71.00   0.50   11.02    --   96.30 -43.00-172.00   50
  6  ω    122.00 147.00   0.50   11.02    --   96.30  77.00 149.00   50
  7  ω    -35.00   9.00   0.50    2.75    --    0.00  38.00  90.00   88
  8  ω     23.00  89.00   0.50    2.75    --    0.00  38.00  90.00  132
  9  ω     55.00 128.00   0.50   11.02    --   96.30 -61.00 -30.00  146
 10  ω     17.00  43.00   0.50   11.02    --   96.30 -61.00 -30.00   52
 11  ω    116.00 148.00   0.50   11.02    --   96.30  61.00-180.00   64
 12  ω     62.00 145.00   0.50   11.02    --   96.30  61.00  60.00  166
 13  ω     63.00 186.00   0.50   11.02    --   96.30  45.00 -60.00  246
 14  ω    138.00 186.00   0.50   11.02    --   96.30  61.00-120.00   96
 15  ω    -50.00 -25.00   0.50    2.75    --    0.00 -77.00  24.00   50
 16  ω    -50.00 -25.00   0.50    2.75    --    0.00 -43.00-172.00   50
 17  ω    -89.00  39.00   0.50    2.75    --    0.00 -38.00  60.00  256
 18  ω     78.00 104.00   0.50    0.50    --   96.30 -82.00-120.00   52
 19  ω     26.00  93.00   0.50    0.50    --   96.30 -82.00 -30.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0131699000
_diffrn_orient_matrix_UB_12      -0.1028806000
_diffrn_orient_matrix_UB_13      -0.0038462000
_diffrn_orient_matrix_UB_21      0.0972650000
_diffrn_orient_matrix_UB_22      0.0069712000
_diffrn_orient_matrix_UB_23      -0.0787300000
_diffrn_orient_matrix_UB_31      0.2362377000
_diffrn_orient_matrix_UB_32      0.0029116000
_diffrn_orient_matrix_UB_33      0.0502570000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2554
_reflns_number_total             2854
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2854
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.022
_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)+(0.0505P)²+0.6082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0960
_refine_ls_wR_factor_ref         0.0982
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C2(H2), C12(H12), C8(H8), C11(H11), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C20(H20A,H20B,H20C), C17(H17A,H17B,H17C)
;
_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
F13 F -0.06160(13) 0.33423(5) 0.60623(5) 0.0264(2) Uani 1 1 d . . . . .
O19 O 0.38462(16) 0.61163(6) 0.82669(6) 0.0238(2) Uani 1 1 d . . . . .
O22 O 0.75278(16) 0.34851(6) 0.83675(6) 0.0260(2) Uani 1 1 d . . . . .
O16 O 0.67560(17) 0.39601(6) 0.95595(6) 0.0249(2) Uani 1 1 d . . . . .
O21 O 0.73766(17) 0.56898(7) 0.86819(7) 0.0319(3) Uani 1 1 d . . . . .
C6 C 0.1345(2) 0.37606(8) 0.63399(8) 0.0183(3) Uani 1 1 d . . . . .
C5 C 0.1831(2) 0.39436(8) 0.71598(8) 0.0183(3) Uani 1 1 d . . . . .
H5 H 0.080363 0.379632 0.750441 0.022 Uiso 1 1 calc R U . . .
C4 C 0.3851(2) 0.43476(8) 0.74743(8) 0.0174(3) Uani 1 1 d . . . . .
C18 C 0.5448(2) 0.55089(8) 0.84708(8) 0.0198(3) Uani 1 1 d . . . . .
C1 C 0.2747(2) 0.39575(8) 0.57916(8) 0.0181(3) Uani 1 1 d . . . . .
C7 C 0.2189(2) 0.37450(8) 0.49120(8) 0.0185(3) Uani 1 1 d . . . . .
C3 C 0.5305(2) 0.45595(8) 0.69437(8) 0.0195(3) Uani 1 1 d . . . . .
H3 H 0.668611 0.483772 0.714833 0.023 Uiso 1 1 calc R U . . .
C2 C 0.4754(2) 0.43682(8) 0.61229(8) 0.0195(3) Uani 1 1 d . . . . .
H2 H 0.576981 0.452070 0.577553 0.023 Uiso 1 1 calc R U . . .
C12 C 0.0110(2) 0.39453(8) 0.44569(8) 0.0209(3) Uani 1 1 d . . . . .
H12 H -0.100195 0.420405 0.471574 0.025 Uiso 1 1 calc R U . . .
C14 C 0.4512(2) 0.45527(8) 0.83810(8) 0.0183(3) Uani 1 1 d . . . . .
C23 C 0.2569(2) 0.44618(9) 0.88477(8) 0.0216(3) Uani 1 1 d . . . . .
H23A H 0.131444 0.482402 0.858138 0.032 Uiso 1 1 calc R U . . .
H23B H 0.303767 0.467097 0.940641 0.032 Uiso 1 1 calc R U . . .
H23C H 0.211656 0.383242 0.885277 0.032 Uiso 1 1 calc R U . . .
C8 C 0.3795(2) 0.33566(8) 0.45195(8) 0.0216(3) Uani 1 1 d . . . . .
H8 H 0.521920 0.321638 0.482029 0.026 Uiso 1 1 calc R U . . .
C15 C 0.6445(2) 0.39337(8) 0.87502(8) 0.0191(3) Uani 1 1 d . . . . .
C11 C -0.0351(2) 0.37698(9) 0.36277(8) 0.0237(3) Uani 1 1 d . . . . .
H11 H -0.176623 0.391489 0.332214 0.028 Uiso 1 1 calc R U . . .
C9 C 0.3321(2) 0.31742(9) 0.36916(9) 0.0252(3) Uani 1 1 d . . . . .
H9 H 0.441806 0.290588 0.343151 0.030 Uiso 1 1 calc R U . . .
C10 C 0.1262(3) 0.33816(9) 0.32466(8) 0.0259(3) Uani 1 1 d . . . . .
H10 H 0.094828 0.325948 0.268111 0.031 Uiso 1 1 calc R U . . .
C20 C 0.4570(3) 0.70418(9) 0.83461(9) 0.0286(3) Uani 1 1 d . . . . .
H20A H 0.579513 0.713233 0.804775 0.043 Uiso 1 1 calc R U . . .
H20B H 0.507312 0.718305 0.892063 0.043 Uiso 1 1 calc R U . . .
H20C H 0.333028 0.743547 0.812352 0.043 Uiso 1 1 calc R U . . .
C17 C 0.8631(2) 0.34568(10) 0.99810(8) 0.0265(3) Uani 1 1 d . . . . .
H17A H 0.861321 0.285260 0.975120 0.040 Uiso 1 1 calc R U . . .
H17B H 0.853562 0.341732 1.055840 0.040 Uiso 1 1 calc R U . . .
H17C H 1.001249 0.375955 0.991893 0.040 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
F13 C6 1.3599(15) . ?
O19 C18 1.3350(16) . ?
O19 C20 1.4500(16) . ?
O22 C15 1.2025(15) . ?
O16 C15 1.3353(16) . ?
O16 C17 1.4472(17) . ?
O21 C18 1.2015(17) . ?
C6 C5 1.3797(18) . ?
C6 C1 1.3927(17) . ?
C5 C4 1.3929(19) . ?
C4 C3 1.3988(17) . ?
C4 C14 1.5315(17) . ?
C18 C14 1.5358(17) . ?
C1 C7 1.4862(18) . ?
C1 C2 1.3974(19) . ?
C7 C12 1.396(2) . ?
C7 C8 1.3998(17) . ?
C3 C2 1.3859(19) . ?
C12 C11 1.3920(19) . ?
C14 C23 1.5383(16) . ?
C14 C15 1.5422(18) . ?
C8 C9 1.3921(19) . ?
C11 C10 1.3919(19) . ?
C9 C10 1.382(2) . ?

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
C18 O19 C20 115.17(11) . . ?
C15 O16 C17 116.07(10) . . ?
F13 C6 C5 117.03(10) . . ?
F13 C6 C1 118.67(12) . . ?
C5 C6 C1 124.28(12) . . ?
C6 C5 C4 118.96(11) . . ?
C5 C4 C3 118.59(12) . . ?
C5 C4 C14 121.62(10) . . ?
C3 C4 C14 119.79(12) . . ?
O19 C18 C14 111.23(11) . . ?
O21 C18 O19 124.16(12) . . ?
O21 C18 C14 124.60(12) . . ?
C6 C1 C7 123.13(12) . . ?
C6 C1 C2 115.51(12) . . ?
C2 C1 C7 121.36(11) . . ?
C12 C7 C1 121.63(11) . . ?
C12 C7 C8 118.69(12) . . ?
C8 C7 C1 119.66(12) . . ?
C2 C3 C4 120.76(12) . . ?
C3 C2 C1 121.89(11) . . ?
C11 C12 C7 120.69(12) . . ?
C4 C14 C18 108.20(10) . . ?
C4 C14 C23 113.07(11) . . ?
C4 C14 C15 109.17(10) . . ?
C18 C14 C23 109.89(10) . . ?
C18 C14 C15 105.74(10) . . ?
C23 C14 C15 110.49(10) . . ?
C9 C8 C7 120.47(13) . . ?
O22 C15 O16 124.25(13) . . ?
O22 C15 C14 125.14(12) . . ?
O16 C15 C14 110.61(10) . . ?
C10 C11 C12 119.93(13) . . ?
C10 C9 C8 120.29(12) . . ?
C9 C10 C11 119.93(13) . . ?

_olex2_date_sample_submission    2025-02-20
_olex2_exptl_crystal_mounting_method 
'mounted on a 18 mm mounted CryoLoop (20 micron, 0.2 - 0.3 mm, Hampton Research)'
_olex2_submission_original_sample_id DM-FBM
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.429
_oxdiff_exptl_absorpt_empirical_full_min 0.373
####################################################################### 
# 
# 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_dm-npm
_audit_block_doi                 10.5517/ccdc.csd.cc2rgqzy
_database_code_depnum_ccdc_archive 'CCDC 2546401'
loop_
_audit_author_name
_audit_author_address
'Gerald Draeger'
;Leibniz University Hannover, Institute of organic Chemistry
Germany
;
_audit_update_record             
;
2026-04-15 deposited with the CCDC.	2026-06-02 downloaded from the CCDC.
;
_audit_creation_date             2025-02-21
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/3
loop_
_audit_author_email
draeger@oci.uni-hannover.de
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 O5'
_chemical_formula_sum            'C17 H18 O5'
_chemical_formula_weight         302.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H18O5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   6.09780(10)
_cell_length_b                   8.1260(2)
_cell_length_c                   30.3631(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.540(2)
_cell_angle_gamma                90
_cell_volume                     1499.79(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9088
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      72.6220
_cell_measurement_theta_min      2.9220
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.554
_exptl_absorpt_coefficient_mu    0.816
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.95a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             640
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -2 5 0.3786
-1 -1 -19 0.0360
3 3 0 0.3355
1 1 19 0.0899
-4 -1 1 0.3813
0 -5 0 0.1353
4 -1 0 0.3872
0 5 0 0.0107
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_min          0.143
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.4438 -2.4555 4.5493 0.0240 -0.2071 0.9780
-0.6827 -0.6445 -18.9381 -0.1102 0.9607 0.2548
3.4726 2.5115 -0.1340 0.0016 -0.0160 -0.9999
0.5045 0.5176 19.1958 0.1116 -0.9725 -0.2042
-3.9325 -0.5331 0.5038 0.3826 0.0439 0.9229
0.1263 -5.2716 0.0017 -0.8883 -0.1020 0.4477
3.9183 -0.6909 -0.4979 -0.5837 -0.0669 -0.8092
0.1771 5.2692 -0.0404 0.8516 0.0978 -0.5150

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            14360
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.436
_diffrn_reflns_theta_min         2.920
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  89.00   0.50    0.50    --    0.00  57.00   0.00  246
  2  ω    -34.00  89.00   0.50    0.50    --    0.00  57.00 150.00  246
  3  ω      7.00 137.00   0.50    1.13    --   96.30 -82.00 -90.00  260
  4  ω     60.00 186.00   0.50    1.13    --   96.30  45.00  30.00  252
  5  ω     60.00 186.00   0.50    1.13    --   96.30  45.00-180.00  252
  6  ω      7.00 131.00   0.50    1.13    --   96.30 -61.00 -90.00  248
  7  ω      7.00 137.00   0.50    1.13    --   96.30 -82.00 -90.00  260
  8  ω     62.00 186.00   0.50    1.13    --   96.30  61.00 150.00  248
  9  ω     58.00 186.00   0.50    1.13    --   96.30  77.00  60.00  256
 10  ω    -39.00  89.00   0.50    0.50    --    0.00  38.00 -90.00  256
 11  ω    -34.00  89.00   0.50    0.50    --    0.00  57.00  60.00  246
 12  ω     58.00 186.00   0.50    1.13    --   96.30  77.00 -90.00  256
 13  ω      7.00  97.00   0.50    1.13    --   96.30 -77.00  90.00  180
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1191769000
_diffrn_orient_matrix_UB_12      0.1656633000
_diffrn_orient_matrix_UB_13      0.0044782000
_diffrn_orient_matrix_UB_21      -0.0201968000
_diffrn_orient_matrix_UB_22      0.0188491000
_diffrn_orient_matrix_UB_23      -0.0506416000
_diffrn_orient_matrix_UB_31      -0.2227405000
_diffrn_orient_matrix_UB_32      -0.0902622000
_diffrn_orient_matrix_UB_33      -0.0023527000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2620
_reflns_number_total             2924
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.95a 64-bit (release 03-11-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.95a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2924
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0384
_refine_ls_restrained_S_all      1.071
_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)+(0.0555P)²+0.4308P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1081
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C2(H2), C5(H5), C8(H8), C3(H3), C7(H7)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C17(H17A,H17B,H17C), C14(H14A,H14B,H14C), C22(H22A,H22B,
 H22C)
;
_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
O16 O 0.17302(14) 0.44404(11) 0.58593(3) 0.0214(2) Uani 1 1 d . . . . .
O13 O 0.31098(15) 0.68905(11) 0.52522(3) 0.0216(2) Uani 1 1 d . . . . .
O21 O 0.70164(15) 0.70631(12) 0.83925(3) 0.0240(2) Uani 1 1 d . . . . .
O18 O -0.14292(15) 0.56458(12) 0.56112(3) 0.0255(2) Uani 1 1 d . . . . .
O19 O 0.40965(16) 0.91982(12) 0.56217(3) 0.0259(2) Uani 1 1 d . . . . .
C9 C 0.3468(2) 0.76499(16) 0.71715(4) 0.0175(3) Uani 1 1 d . . . . .
C15 C 0.0416(2) 0.57358(16) 0.57827(4) 0.0178(3) Uani 1 1 d . . . . .
C1 C 0.2879(2) 0.71755(15) 0.63792(4) 0.0168(3) Uani 1 1 d . . . . .
C10 C 0.2189(2) 0.78233(16) 0.67628(4) 0.0179(3) Uani 1 1 d . . . . .
H10 H 0.082960 0.839827 0.675429 0.021 Uiso 1 1 calc R U . . .
C2 C 0.4925(2) 0.63361(16) 0.63970(4) 0.0190(3) Uani 1 1 d . . . . .
H2 H 0.542420 0.589190 0.613337 0.023 Uiso 1 1 calc R U . . .
C12 C 0.3079(2) 0.79307(16) 0.55891(4) 0.0176(3) Uani 1 1 d . . . . .
C5 C 0.6768(2) 0.65887(16) 0.75985(4) 0.0194(3) Uani 1 1 d . . . . .
H5 H 0.813071 0.601676 0.761091 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5500(2) 0.68029(15) 0.71871(4) 0.0179(3) Uani 1 1 d . . . . .
C6 C 0.5995(2) 0.72206(16) 0.79771(4) 0.0203(3) Uani 1 1 d . . . . .
C8 C 0.2762(2) 0.83163(17) 0.75699(4) 0.0208(3) Uani 1 1 d . . . . .
H8 H 0.141671 0.890924 0.756334 0.025 Uiso 1 1 calc R U . . .
C3 C 0.6193(2) 0.61537(16) 0.67863(4) 0.0194(3) Uani 1 1 d . . . . .
H3 H 0.755539 0.558529 0.678862 0.023 Uiso 1 1 calc R U . . .
C11 C 0.1516(2) 0.73637(16) 0.59343(4) 0.0177(3) Uani 1 1 d . . . . .
C20 C -0.0284(2) 0.86852(17) 0.59418(4) 0.0213(3) Uani 1 1 d . . . . .
H20A H -0.094158 0.887046 0.564087 0.032 Uiso 1 1 calc R U . . .
H20B H 0.036363 0.971353 0.605988 0.032 Uiso 1 1 calc R U . . .
H20C H -0.142267 0.831399 0.612955 0.032 Uiso 1 1 calc R U . . .
C7 C 0.3992(2) 0.81136(16) 0.79610(4) 0.0219(3) Uani 1 1 d . . . . .
H7 H 0.350507 0.857280 0.822400 0.026 Uiso 1 1 calc R U . . .
C17 C 0.0834(2) 0.28916(16) 0.56906(4) 0.0240(3) Uani 1 1 d . . . . .
H17A H 0.039045 0.300240 0.537472 0.036 Uiso 1 1 calc R U . . .
H17B H -0.044831 0.259502 0.584895 0.036 Uiso 1 1 calc R U . . .
H17C H 0.195522 0.203009 0.573419 0.036 Uiso 1 1 calc R U . . .
C14 C 0.4577(2) 0.73258(18) 0.49156(4) 0.0253(3) Uani 1 1 d . . . . .
H14A H 0.442356 0.651939 0.467518 0.038 Uiso 1 1 calc R U . . .
H14B H 0.609960 0.732896 0.504572 0.038 Uiso 1 1 calc R U . . .
H14C H 0.419525 0.842256 0.479915 0.038 Uiso 1 1 calc R U . . .
C22 C 0.9005(2) 0.6124(2) 0.84366(4) 0.0277(3) Uani 1 1 d . . . . .
H22A H 1.012972 0.666965 0.827514 0.042 Uiso 1 1 calc R U . . .
H22B H 0.872718 0.501933 0.831515 0.042 Uiso 1 1 calc R U . . .
H22C H 0.952156 0.603905 0.874971 0.042 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
O16 C15 1.3324(15) . ?
O16 C17 1.4493(15) . ?
O13 C12 1.3281(15) . ?
O13 C14 1.4541(15) . ?
O21 C6 1.3676(15) . ?
O21 C22 1.4302(17) . ?
O18 C15 1.2039(16) . ?
O19 C12 1.2025(16) . ?
C9 C10 1.4197(17) . ?
C9 C4 1.4148(18) . ?
C9 C8 1.4231(17) . ?
C15 C11 1.5373(17) . ?
C1 C10 1.3739(17) . ?
C1 C2 1.4193(17) . ?
C1 C11 1.5365(17) . ?
C2 C3 1.3683(17) . ?
C12 C11 1.5417(16) . ?
C5 C4 1.4268(17) . ?
C5 C6 1.3761(18) . ?
C4 C3 1.4210(17) . ?
C6 C7 1.4182(19) . ?
C8 C7 1.3635(18) . ?
C11 C20 1.5373(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 O16 C17 114.81(10) . . ?
C12 O13 C14 115.68(10) . . ?
C6 O21 C22 117.21(10) . . ?
C10 C9 C8 121.52(11) . . ?
C4 C9 C10 119.80(11) . . ?
C4 C9 C8 118.68(12) . . ?
O16 C15 C11 112.65(10) . . ?
O18 C15 O16 123.79(12) . . ?
O18 C15 C11 123.55(11) . . ?
C10 C1 C2 118.62(11) . . ?
C10 C1 C11 121.78(11) . . ?
C2 C1 C11 119.59(10) . . ?
C1 C10 C9 121.26(11) . . ?
C3 C2 C1 121.33(11) . . ?
O13 C12 C11 112.37(10) . . ?
O19 C12 O13 124.74(11) . . ?
O19 C12 C11 122.86(11) . . ?
C6 C5 C4 119.21(12) . . ?
C9 C4 C5 120.08(11) . . ?
C9 C4 C3 118.08(11) . . ?
C3 C4 C5 121.82(12) . . ?
O21 C6 C5 125.04(12) . . ?
O21 C6 C7 114.07(11) . . ?
C5 C6 C7 120.89(12) . . ?
C7 C8 C9 120.77(12) . . ?
C2 C3 C4 120.90(12) . . ?
C15 C11 C12 109.40(10) . . ?
C1 C11 C15 111.75(10) . . ?
C1 C11 C12 107.90(10) . . ?
C1 C11 C20 113.17(10) . . ?
C20 C11 C15 108.06(10) . . ?
C20 C11 C12 106.38(10) . . ?
C8 C7 C6 120.32(12) . . ?

_olex2_date_sample_submission    2025-02-20
_olex2_exptl_crystal_mounting_method 
'mounted on a 18 mm mounted CryoLoop (20 micron, 0.2 - 0.3 mm, Hampton Research)'
_olex2_submission_original_sample_id DM-NPM
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.131
_oxdiff_exptl_absorpt_empirical_full_min 0.285
