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

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

data_03526
_audit_block_doi                 10.5517/ccdc.csd.cc2bn1sv
_database_code_depnum_ccdc_archive 'CCDC 2164227'
loop_
_audit_author_name
_audit_author_address
'Josefina Perles'
;Universidad Autonoma de Madrid
Spain
;
_audit_update_record             
;
2022-04-04 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            MSP-348_250K
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H28 F2 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         398.48

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   10.1227(17)
_cell_length_b                   19.823(2)
_cell_length_c                   21.730(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4360.4(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3428
_cell_measurement_theta_min      3.0265
_cell_measurement_theta_max      20.2096
_cell_measurement_temperature    250.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.056
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696

_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      250.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            31693
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_av_unetI/netI     0.0494
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_full        25.34
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26

_refine_special_details          
;
;

_reflns_number_total             3954
_reflns_number_gt                2388
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0504
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1445
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_number_reflns         3954
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0760P)²+0.0063P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.162
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'

_computing_data_collection       'Bruker Instrument Service v2010.9.0.0'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.8779(2) 0.72949(12) 0.52228(11) 0.0513(6) Uani d . . . 1 . .
C C2 0.8794(2) 0.77613(11) 0.57535(11) 0.0508(6) Uani d . . . 1 . .
H H2A 0.822625 0.814981 0.566472 0.061000 Uiso calc U . R 1 . .
H H2B 0.969485 0.792787 0.581799 0.061000 Uiso calc U . R 1 . .
C C3 0.8311(2) 0.74125(10) 0.63376(10) 0.0415(5) Uani d . . . 1 . .
H H3A 0.824215 0.774613 0.666885 0.050000 Uiso calc U . R 1 . .
H H3B 0.896046 0.707280 0.646314 0.050000 Uiso calc U . R 1 . .
C C4 0.6971(2) 0.70725(9) 0.62486(9) 0.0330(5) Uani d . . . 1 . .
H H4 0.630765 0.742936 0.617080 0.040000 Uiso calc U . R 1 . .
C C5 0.6996(2) 0.66078(10) 0.56929(9) 0.0406(6) Uani d . . . 1 . .
H H5A 0.610326 0.643396 0.562036 0.049000 Uiso calc U . R 1 . .
H H5B 0.757143 0.622238 0.578187 0.049000 Uiso calc U . R 1 . .
C C6 0.7485(2) 0.69583(12) 0.51108(10) 0.0513(6) Uani d . . . 1 . .
H H6A 0.758075 0.662581 0.478007 0.062000 Uiso calc U . R 1 . .
H H6B 0.683412 0.729471 0.497919 0.062000 Uiso calc U . R 1 . .
C C7 0.6571(2) 0.66992(10) 0.68343(9) 0.0371(5) Uani d . . . 1 . .
H H7A 0.704041 0.626694 0.684663 0.045000 Uiso calc U . R 1 . .
H H7B 0.686257 0.696412 0.719008 0.045000 Uiso calc U . R 1 . .
C C8 0.5098(2) 0.65635(10) 0.68980(9) 0.0365(5) Uani d . . . 1 . .
H H8 0.475343 0.632828 0.652946 0.044000 Uiso calc U . R 1 . .
C C9 0.4379(2) 0.72396(11) 0.69953(10) 0.0381(5) Uani d . . . 1 . .
C C10 0.2526(3) 0.79810(13) 0.68108(13) 0.0676(8) Uani d . . . 1 . .
H H10A 0.173099 0.793998 0.705694 0.101000 Uiso calc U . R 1 . .
H H10B 0.229838 0.814484 0.640382 0.101000 Uiso calc U . R 1 . .
H H10C 0.312783 0.829585 0.700638 0.101000 Uiso calc U . R 1 . .
C C11 0.2380(3) 0.67928(13) 0.64680(13) 0.0660(7) Uani d . . . 1 . .
H H11A 0.153106 0.675893 0.667319 0.099000 Uiso calc U . R 1 . .
H H11B 0.284096 0.636534 0.649972 0.099000 Uiso calc U . R 1 . .
H H11C 0.224390 0.690299 0.603773 0.099000 Uiso calc U . R 1 . .
C C12 0.4684(2) 0.55160(10) 0.74083(10) 0.0367(5) Uani d . . . 1 . .
C C13 0.4581(2) 0.51441(10) 0.68104(10) 0.0403(6) Uani d . . . 1 . .
C C14 0.5689(2) 0.49556(11) 0.64851(12) 0.0522(7) Uani d . . . 1 . .
H H14 0.653138 0.503811 0.665090 0.063000 Uiso calc U . R 1 . .
C C15 0.5576(3) 0.46469(12) 0.59188(13) 0.0675(8) Uani d . . . 1 . .
H H15 0.633867 0.452752 0.569770 0.081000 Uiso calc U . R 1 . .
C C16 0.4357(4) 0.45147(13) 0.56789(14) 0.0744(9) Uani d . . . 1 . .
H H16 0.428295 0.430636 0.529188 0.089000 Uiso calc U . R 1 . .
C C17 0.3245(3) 0.46844(13) 0.59999(15) 0.0748(9) Uani d . . . 1 . .
H H17 0.240684 0.458831 0.583613 0.090000 Uiso calc U . R 1 . .
C C18 0.3355(3) 0.49970(12) 0.65649(13) 0.0600(7) Uani d . . . 1 . .
H H18 0.258789 0.511115 0.678517 0.072000 Uiso calc U . R 1 . .
C C19 0.4555(2) 0.51159(10) 0.79881(11) 0.0394(5) Uani d . . . 1 . .
C C20 0.4419(3) 0.44207(11) 0.79779(12) 0.0564(7) Uani d . . . 1 . .
H H20 0.439675 0.419254 0.759879 0.068000 Uiso calc U . R 1 . .
C C21 0.4316(3) 0.40583(12) 0.85212(15) 0.0693(8) Uani d . . . 1 . .
H H21 0.422730 0.358653 0.850701 0.083000 Uiso calc U . R 1 . .
C C22 0.4342(3) 0.43804(13) 0.90781(13) 0.0629(7) Uani d . . . 1 . .
H H22 0.426659 0.413272 0.944534 0.075000 Uiso calc U . R 1 . .
C C23 0.4478(2) 0.50713(12) 0.90946(12) 0.0545(7) Uani d . . . 1 . .
H H23 0.449296 0.529635 0.947532 0.065000 Uiso calc U . R 1 . .
C C24 0.4594(2) 0.54344(10) 0.85577(11) 0.0431(6) Uani d . . . 1 . .
H H24 0.470010 0.590498 0.857635 0.052000 Uiso calc U . R 1 . .
F F1 0.91825(16) 0.76227(9) 0.46976(7) 0.0842(5) Uani d . . . 1 . .
F F3 0.97435(14) 0.68064(7) 0.53083(7) 0.0691(5) Uani d . . . 1 . .
N N1 0.31638(19) 0.73196(9) 0.67583(8) 0.0480(5) Uani d . . . 1 . .
N N2 0.48882(18) 0.61531(8) 0.74564(8) 0.0384(4) Uani d . . . 1 . .
O O1 0.49311(16) 0.76949(7) 0.72754(8) 0.0519(4) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 F1 . 1.375(2) ?
C1 F3 . 1.388(3) ?
C1 C2 . 1.478(3) ?
C1 C6 . 1.490(3) ?
C2 C3 . 1.526(3) ?
C3 C4 . 1.527(3) ?
C4 C5 . 1.519(3) ?
C4 C7 . 1.527(3) ?
C5 C6 . 1.526(3) ?
C7 C8 . 1.522(3) ?
C8 N2 . 1.476(2) ?
C8 C9 . 1.539(3) ?
C9 O1 . 1.224(2) ?
C9 N1 . 1.343(3) ?
C10 N1 . 1.466(3) ?
C11 N1 . 1.456(3) ?
C12 N2 . 1.284(2) ?
C12 C19 . 1.495(3) ?
C12 C13 . 1.498(3) ?
C13 C14 . 1.378(3) ?
C13 C18 . 1.381(3) ?
C14 C15 . 1.379(4) ?
C15 C16 . 1.364(4) ?
C16 C17 . 1.366(4) ?
C17 C18 . 1.380(4) ?
C19 C20 . 1.385(3) ?
C19 C24 . 1.390(3) ?
C20 C21 . 1.386(4) ?
C21 C22 . 1.369(4) ?
C22 C23 . 1.377(3) ?
C23 C24 . 1.376(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 C1 F3 . . 103.40(18) ?
F1 C1 C2 . . 110.41(19) ?
F3 C1 C2 . . 108.95(19) ?
F1 C1 C6 . . 109.71(19) ?
F3 C1 C6 . . 109.2(2) ?
C2 C1 C6 . . 114.6(2) ?
C1 C2 C3 . . 111.23(17) ?
C2 C3 C4 . . 112.30(17) ?
C5 C4 C3 . . 110.71(17) ?
C5 C4 C7 . . 111.91(16) ?
C3 C4 C7 . . 110.12(17) ?
C4 C5 C6 . . 112.85(17) ?
C1 C6 C5 . . 110.71(19) ?
C8 C7 C4 . . 114.91(17) ?
N2 C8 C7 . . 108.23(16) ?
N2 C8 C9 . . 107.40(16) ?
C7 C8 C9 . . 108.77(16) ?
O1 C9 N1 . . 121.5(2) ?
O1 C9 C8 . . 119.6(2) ?
N1 C9 C8 . . 118.9(2) ?
N2 C12 C19 . . 117.86(19) ?
N2 C12 C13 . . 124.48(19) ?
C19 C12 C13 . . 117.65(17) ?
C14 C13 C18 . . 118.4(2) ?
C14 C13 C12 . . 121.4(2) ?
C18 C13 C12 . . 120.1(2) ?
C13 C14 C15 . . 120.7(2) ?
C16 C15 C14 . . 120.1(3) ?
C15 C16 C17 . . 120.2(3) ?
C16 C17 C18 . . 119.9(3) ?
C17 C18 C13 . . 120.7(2) ?
C20 C19 C24 . . 118.0(2) ?
C20 C19 C12 . . 121.5(2) ?
C24 C19 C12 . . 120.48(18) ?
C19 C20 C21 . . 120.6(2) ?
C22 C21 C20 . . 120.7(2) ?
C21 C22 C23 . . 119.3(2) ?
C24 C23 C22 . . 120.4(2) ?
C23 C24 C19 . . 121.0(2) ?
C9 N1 C11 . . 125.51(19) ?
C9 N1 C10 . . 118.6(2) ?
C11 N1 C10 . . 115.8(2) ?
C12 N2 C8 . . 119.88(18) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
F1 C1 C2 C3 . . . . 178.36(18) ?
F3 C1 C2 C3 . . . . -68.7(2) ?
C6 C1 C2 C3 . . . . 53.9(3) ?
C1 C2 C3 C4 . . . . -52.8(3) ?
C2 C3 C4 C5 . . . . 52.6(2) ?
C2 C3 C4 C7 . . . . 176.86(17) ?
C3 C4 C5 C6 . . . . -52.8(2) ?
C7 C4 C5 C6 . . . . -176.03(18) ?
F1 C1 C6 C5 . . . . -178.35(18) ?
F3 C1 C6 C5 . . . . 69.0(2) ?
C2 C1 C6 C5 . . . . -53.5(3) ?
C4 C5 C6 C1 . . . . 52.6(3) ?
C5 C4 C7 C8 . . . . -77.9(2) ?
C3 C4 C7 C8 . . . . 158.47(17) ?
C4 C7 C8 N2 . . . . 175.33(15) ?
C4 C7 C8 C9 . . . . -68.3(2) ?
N2 C8 C9 O1 . . . . 84.1(2) ?
C7 C8 C9 O1 . . . . -32.8(3) ?
N2 C8 C9 N1 . . . . -97.2(2) ?
C7 C8 C9 N1 . . . . 145.92(18) ?
N2 C12 C13 C14 . . . . 80.4(3) ?
C19 C12 C13 C14 . . . . -99.0(2) ?
N2 C12 C13 C18 . . . . -98.0(3) ?
C19 C12 C13 C18 . . . . 82.6(3) ?
C18 C13 C14 C15 . . . . 2.1(3) ?
C12 C13 C14 C15 . . . . -176.3(2) ?
C13 C14 C15 C16 . . . . -1.1(4) ?
C14 C15 C16 C17 . . . . -0.3(4) ?
C15 C16 C17 C18 . . . . 0.7(4) ?
C16 C17 C18 C13 . . . . 0.3(4) ?
C14 C13 C18 C17 . . . . -1.7(4) ?
C12 C13 C18 C17 . . . . 176.8(2) ?
N2 C12 C19 C20 . . . . -175.8(2) ?
C13 C12 C19 C20 . . . . 3.6(3) ?
N2 C12 C19 C24 . . . . 3.0(3) ?
C13 C12 C19 C24 . . . . -177.64(19) ?
C24 C19 C20 C21 . . . . 0.5(4) ?
C12 C19 C20 C21 . . . . 179.2(2) ?
C19 C20 C21 C22 . . . . 0.2(4) ?
C20 C21 C22 C23 . . . . -0.3(4) ?
C21 C22 C23 C24 . . . . -0.3(4) ?
C22 C23 C24 C19 . . . . 1.0(4) ?
C20 C19 C24 C23 . . . . -1.1(3) ?
C12 C19 C24 C23 . . . . -179.9(2) ?
O1 C9 N1 C11 . . . . -174.1(2) ?
C8 C9 N1 C11 . . . . 7.2(3) ?
O1 C9 N1 C10 . . . . 3.4(3) ?
C8 C9 N1 C10 . . . . -175.31(18) ?
C19 C12 N2 C8 . . . . 176.56(17) ?
C13 C12 N2 C8 . . . . -2.8(3) ?
C7 C8 N2 C12 . . . . -101.8(2) ?
C9 C8 N2 C12 . . . . 141.0(2) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C10 H10A O1 6_557 0.97 2.38 3.342(3) 171.5 ?

