# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_AN1
_database_code_depnum_ccdc_archive 'CCDC 2294269'
loop_
_audit_author_name
_audit_author_address
'Deschamps Guillot'
;University Paris Cite
France
;
_audit_update_record             
;
2023-12-08 deposited with the CCDC.	2024-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            
2-(3-morpholino-2,2-diphenyl-2,3-dihydrobenzol[b][1,4]dioxin-6-yl)ethan-1-ol
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H27 N O4'
_chemical_formula_sum            'C26 H27 N O4'
_chemical_formula_weight         417.48

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   39.383(3)
_cell_length_b                   6.2918(5)
_cell_length_c                   17.9687(14)
_cell_angle_alpha                90
_cell_angle_beta                 107.702(4)
_cell_angle_gamma                90
_cell_volume                     4241.7(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6472
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      25

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             1776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48553
_diffrn_reflns_av_unetI/netI     0.1230
_diffrn_reflns_av_R_equivalents  0.1338
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_h_max       51
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.171
_diffrn_reflns_theta_max         30.565
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6472
_reflns_number_gt                3101
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ORTEP(III)
_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)+(0.0444P)²+44.5471P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6472
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2139
_refine_ls_R_factor_gt           0.1204
_refine_ls_wR_factor_ref         0.2906
_refine_ls_wR_factor_gt          0.2540
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
C1 C 0.15493(11) 0.6916(7) 0.1877(2) 0.0264(9) Uani 1 1 d . . . . .
C2 C 0.10163(12) 0.8213(7) 0.0979(2) 0.0269(10) Uani 1 1 d . . . . .
C3 C 0.12422(12) 0.9887(7) 0.0714(2) 0.0250(9) Uani 1 1 d . . . . .
H3 H 0.1094 1.1168 0.0585 0.030 Uiso 1 1 calc R U . . .
C4 C 0.17074(12) 0.8892(7) 0.1879(2) 0.0268(9) Uani 1 1 d . . . . .
C5 C 0.20291(12) 0.9349(7) 0.2436(3) 0.0289(10) Uani 1 1 d . . . . .
H5 H 0.2130 1.0688 0.2443 0.035 Uiso 1 1 calc R U . . .
C6 C 0.22042(12) 0.7827(8) 0.2986(3) 0.0324(11) Uani 1 1 d . . . . .
C7 C 0.20457(13) 0.5844(8) 0.2953(3) 0.0350(11) Uani 1 1 d . . . . .
H7 H 0.2160 0.4796 0.3305 0.042 Uiso 1 1 calc R U . . .
C8 C 0.17221(12) 0.5399(7) 0.2407(3) 0.0299(10) Uani 1 1 d . . . . .
H8 H 0.1620 0.4061 0.2397 0.036 Uiso 1 1 calc R U . . .
C9 C 0.24694(15) 0.9603(8) 0.4271(3) 0.0404(13) Uani 1 1 d . . . . .
H9A H 0.2300 0.8780 0.4448 0.052 Uiso 1 1 calc R U . A 1
H9B H 0.2689 0.9668 0.4702 0.052 Uiso 1 1 calc R U . A 1
C10 C 0.25456(13) 0.8382(9) 0.3608(3) 0.0412(13) Uani 1 1 d . . . . .
H10A H 0.2694 0.9240 0.3382 0.054 Uiso 1 1 calc R U . . .
H10B H 0.2675 0.7090 0.3811 0.054 Uiso 1 1 calc R U . . .
C11 C 0.14538(14) 1.0477(9) -0.1160(3) 0.0399(12) Uani 1 1 d . . . . .
H11A H 0.1207 1.0312 -0.1476 0.052 Uiso 1 1 calc R U . . .
H11B H 0.1557 1.1616 -0.1385 0.052 Uiso 1 1 calc R U . . .
C12 C 0.14658(14) 1.1090(8) -0.0334(3) 0.0348(11) Uani 1 1 d . . . . .
H12A H 0.1709 1.1393 -0.0024 0.045 Uiso 1 1 calc R U . . .
H12B H 0.1323 1.2355 -0.0345 0.045 Uiso 1 1 calc R U . . .
C13 C 0.15440(14) 0.7422(8) 0.0023(3) 0.0359(11) Uani 1 1 d . . . . .
H13A H 0.1460 0.6243 0.0267 0.047 Uiso 1 1 calc R U . . .
H13B H 0.1790 0.7709 0.0322 0.047 Uiso 1 1 calc R U . . .
C14 C 0.15199(15) 0.6866(8) -0.0807(3) 0.0385(12) Uani 1 1 d . . . . .
H14A H 0.1664 0.5616 -0.0809 0.050 Uiso 1 1 calc R U . . .
H14B H 0.1275 0.6528 -0.1095 0.050 Uiso 1 1 calc R U . . .
C15 C 0.07160(12) 0.7429(7) 0.0283(3) 0.0264(9) Uani 1 1 d . . . . .
C16 C 0.04364(12) 0.8791(8) -0.0084(3) 0.0342(11) Uani 1 1 d . . . . .
H16 H 0.0437 1.0167 0.0105 0.041 Uiso 1 1 calc R U . . .
C17 C 0.01602(13) 0.8164(9) -0.0716(3) 0.0383(12) Uani 1 1 d . . . . .
H17 H -0.0022 0.9107 -0.0955 0.046 Uiso 1 1 calc R U . . .
C18 C 0.01555(15) 0.6119(10) -0.0993(3) 0.0462(14) Uani 1 1 d . . . . .
H18 H -0.0032 0.5671 -0.1419 0.055 Uiso 1 1 calc R U . . .
C19 C 0.04273(16) 0.4744(9) -0.0641(3) 0.0478(14) Uani 1 1 d . . . . .
H19 H 0.0424 0.3368 -0.0832 0.057 Uiso 1 1 calc R U . . .
C20 C 0.07045(15) 0.5387(8) -0.0005(3) 0.0405(12) Uani 1 1 d . . . . .
H20 H 0.0886 0.4435 0.0231 0.049 Uiso 1 1 calc R U . . .
C21 C 0.08551(12) 0.9114(7) 0.1590(2) 0.0257(9) Uani 1 1 d . . . . .
C22 C 0.08721(13) 1.1208(8) 0.1839(3) 0.0337(11) Uani 1 1 d . . . . .
H22 H 0.0999 1.2201 0.1645 0.040 Uiso 1 1 calc R U . . .
C23 C 0.06996(14) 1.1837(8) 0.2380(3) 0.0370(12) Uani 1 1 d . . . . .
H23 H 0.0714 1.3241 0.2550 0.044 Uiso 1 1 calc R U . . .
C24 C 0.05090(15) 1.0379(10) 0.2659(3) 0.0452(14) Uani 1 1 d . . . . .
H24 H 0.0392 1.0804 0.3014 0.054 Uiso 1 1 calc R U . . .
C25 C 0.04892(15) 0.8296(9) 0.2418(3) 0.0434(13) Uani 1 1 d . . . . .
H25 H 0.0362 0.7314 0.2614 0.052 Uiso 1 1 calc R U . . .
C26 C 0.06573(13) 0.7669(8) 0.1891(3) 0.0369(12) Uani 1 1 d . . . . .
H26 H 0.0640 0.6260 0.1728 0.044 Uiso 1 1 calc R U . . .
N1 N 0.13241(10) 0.9309(6) 0.0014(2) 0.0297(9) Uani 1 1 d . . . . .
O1 O 0.12298(8) 0.6403(5) 0.13159(17) 0.0275(7) Uani 1 1 d . . . . .
O2 O 0.15515(8) 1.0466(5) 0.13529(18) 0.0321(8) Uani 1 1 d . . . . .
O3 O 0.16395(10) 0.8573(6) -0.1186(2) 0.0424(9) Uani 1 1 d . . . . .
O4A O 0.2342(2) 1.1588(11) 0.4126(4) 0.052(2) Uani 0.556(8) 1 d . . P B 1
H4A H 0.2162 1.1581 0.3746 0.556(8) Uiso 0.556(8) 1 calc R U P B 1
O4B O 0.2744(2) 1.0014(12) 0.4898(5) 0.037(2) Uani 0.444(8) 1 d . . P B 2
H4B H 0.2928 0.9597 0.4824 0.444 Uiso 0.444(8) 1 calc R U P B 2


_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
C1 C8 1.374(6) . ?
C1 C4 1.390(6) . ?
C1 O1 1.390(5) . ?
C2 O1 1.435(5) . ?
C2 C15 1.518(6) . ?
C2 C21 1.534(6) . ?
C2 C3 1.545(6) . ?
C3 N1 1.436(5) . ?
C3 O2 1.444(5) . ?
C4 O2 1.378(5) . ?
C4 C5 1.384(6) . ?
C5 C6 1.399(7) . ?
C6 C7 1.388(7) . ?
C6 C10 1.504(7) . ?
C7 C8 1.380(7) . ?
C9 O4B 1.329(9) . ?
C9 O4A 1.342(8) . ?
C9 C10 1.523(7) . ?
C11 O3 1.412(6) . ?
C11 C12 1.522(7) . ?
C12 N1 1.474(6) . ?
C13 N1 1.467(6) . ?
C13 C14 1.507(7) . ?
C14 O3 1.426(6) . ?
C15 C20 1.382(7) . ?
C15 C16 1.393(6) . ?
C16 C17 1.370(7) . ?
C17 C18 1.377(8) . ?
C18 C19 1.372(8) . ?
C19 C20 1.379(7) . ?
C21 C22 1.386(6) . ?
C21 C26 1.408(6) . ?
C22 C23 1.402(7) . ?
C23 C24 1.374(8) . ?
C24 C25 1.375(8) . ?
C25 C26 1.369(7) . ?

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
C8 C1 C4 119.5(4) . . ?
C8 C1 O1 119.3(4) . . ?
C4 C1 O1 121.1(4) . . ?
O1 C2 C15 107.4(4) . . ?
O1 C2 C21 108.0(3) . . ?
C15 C2 C21 108.7(4) . . ?
O1 C2 C3 110.6(4) . . ?
C15 C2 C3 110.2(3) . . ?
C21 C2 C3 111.8(4) . . ?
N1 C3 O2 113.6(4) . . ?
N1 C3 C2 113.6(4) . . ?
O2 C3 C2 110.6(3) . . ?
O2 C4 C5 117.7(4) . . ?
O2 C4 C1 122.3(4) . . ?
C5 C4 C1 119.9(4) . . ?
C4 C5 C6 121.0(4) . . ?
C7 C6 C5 117.8(4) . . ?
C7 C6 C10 122.0(5) . . ?
C5 C6 C10 120.2(5) . . ?
C8 C7 C6 121.3(5) . . ?
C1 C8 C7 120.5(5) . . ?
O4B C9 C10 117.3(6) . . ?
O4A C9 C10 118.0(5) . . ?
C6 C10 C9 110.7(4) . . ?
O3 C11 C12 112.6(4) . . ?
N1 C12 C11 108.5(4) . . ?
N1 C13 C14 108.5(4) . . ?
O3 C14 C13 111.5(4) . . ?
C20 C15 C16 117.6(4) . . ?
C20 C15 C2 122.7(4) . . ?
C16 C15 C2 119.8(4) . . ?
C17 C16 C15 122.0(5) . . ?
C16 C17 C18 119.2(5) . . ?
C19 C18 C17 120.0(5) . . ?
C18 C19 C20 120.5(5) . . ?
C19 C20 C15 120.8(5) . . ?
C22 C21 C26 117.9(4) . . ?
C22 C21 C2 126.3(4) . . ?
C26 C21 C2 115.7(4) . . ?
C21 C22 C23 120.4(5) . . ?
C24 C23 C22 119.9(5) . . ?
C23 C24 C25 120.4(5) . . ?
C26 C25 C24 120.0(5) . . ?
C25 C26 C21 121.3(5) . . ?
C3 N1 C13 119.0(4) . . ?
C3 N1 C12 113.2(4) . . ?
C13 N1 C12 108.8(4) . . ?
C1 O1 C2 114.0(3) . . ?
C4 O2 C3 117.1(3) . . ?
C11 O3 C14 112.0(4) . . ?

_refine_diff_density_max         0.491
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.091

