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

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

data_p21c
_database_code_depnum_ccdc_archive 'CCDC 2101324'
loop_
_audit_author_name
_audit_author_address
'Ricardo A. Peralta'
;Universidad Autonoma Metropolitana
Mexico
;
_audit_update_record             
;
2025-09-05 deposited with the CCDC.	2025-10-30 downloaded from the CCDC.
;
_audit_creation_date             2025-09-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H26 O3'
_chemical_formula_sum            'C22 H26 O3'
_chemical_formula_weight         338.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C25H25O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   11.6017(8)
_cell_length_b                   13.7639(6)
_cell_length_c                   12.7600(8)
_cell_angle_alpha                90
_cell_angle_beta                 114.935(8)
_cell_angle_gamma                90
_cell_volume                     1847.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11370
_cell_measurement_temperature    150.00(14)
_cell_measurement_theta_max      28.5150
_cell_measurement_theta_min      3.7860
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.44030
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.051
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            80523
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.371
_diffrn_reflns_theta_min         3.444
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1695
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  91.00   1.00   15.00    --   19.03  37.00-120.00   98
  2  ω     -2.00  88.00   1.00   15.00    --   19.03  57.00  30.00   90
  3  ω      1.00  80.00   1.00   15.00    --   19.03-131.00  99.28   79
  4  ω     -2.00  88.00   1.00   15.00    --   19.03  57.00 120.00   90
  5  ω     -7.00  91.00   1.00   15.00    --   19.03  37.00 -30.00   98
  6  ω    -50.00  40.00   1.00   15.00    --   19.03 -57.00 120.00   90
  7  ω    -40.00  49.00   1.00   15.00    --  -19.65  57.00 -30.00   89
  8  ω    -25.00  22.00   1.00   15.00    --  -19.65 -99.00-150.00   47
  9  ω    -50.00  50.00   1.00   15.00    --  -19.65  77.00-150.00  100
 10  ω    -54.00  92.00   1.00   15.00    --   19.03   0.00-180.00  146
 11  ω    -54.00  92.00   1.00   15.00    --   19.03   0.00-150.00  146
 12  ω    -90.00 -10.00   1.00   15.00    --  -19.65 146.00 118.98   80
 13  ω    -25.00  22.00   1.00   15.00    --  -19.65 -99.00 150.00   47
 14  ω    -96.00 -32.00   1.00   15.00    --  -19.65 178.00  30.00   64
 15  ω    -25.00  22.00   1.00   15.00    --  -19.65 -99.00 -90.00   47
 16  ω    -81.00  -1.00   1.00   15.00    --  -19.65 131.00 -89.05   80
 17  ω    -54.00  92.00   1.00   15.00    --   19.03   0.00 -90.00  146
 18  ω    -54.00  92.00   1.00   15.00    --   19.03   0.00 -60.00  146
 19  ω    -54.00  92.00   1.00   15.00    --   19.03   0.00 -30.00  146
 20  ω    -54.00  92.00   1.00   15.00    --   19.03   0.00   0.00  146
 21  ω    -54.00  -5.00   1.00   15.00    --   19.03   0.00  30.00   49
 22  ω    -54.00  92.00   1.00   15.00    --   19.03   0.00-120.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0661978000
_diffrn_orient_matrix_UB_12      0.0008571000
_diffrn_orient_matrix_UB_13      0.0357129000
_diffrn_orient_matrix_UB_21      0.0098805000
_diffrn_orient_matrix_UB_22      -0.0353398000
_diffrn_orient_matrix_UB_23      -0.0358849000
_diffrn_orient_matrix_UB_31      0.0077873000
_diffrn_orient_matrix_UB_32      0.0375259000
_diffrn_orient_matrix_UB_33      -0.0345699000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3528
_reflns_number_total             4806
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         4806
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0816
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.054
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1586
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C009(H009), C00D(H00D), C00E(H00E)
1.b Secondary CH2 refined with riding coordinates:
 C00L(H00L,H00M), C00M(H00N,H00O), C00N(H00P,H00Q)
1.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00A(H00A), C00F(H00F), C00H(H00H)
1.d Idealised Me refined as rotating group:
 C00J(H00B,H00C,H00G), C00K(H00I,H00J,H00K), C00O(H00R,H00S,H00T), C00P(H00U,
 H00V,H00W)
1.e Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
O001 O 0.60529(9) 0.38522(7) 0.80049(8) 0.0200(2) Uani 1 1 d . . . . .
O002 O 0.76247(9) 0.14476(8) 0.53927(8) 0.0251(3) Uani 1 1 d . . . . .
H002 H 0.7059 0.1391 0.4715 0.038 Uiso 1 1 calc GR . . . .
O003 O 0.15511(10) 0.24008(8) 0.61325(9) 0.0279(3) Uani 1 1 d . . . . .
C004 C 0.80302(13) 0.22087(10) 0.71726(12) 0.0202(3) Uani 1 1 d . . . . .
C005 C 0.71992(13) 0.20515(10) 0.60115(11) 0.0195(3) Uani 1 1 d . . . . .
C006 C 0.64404(13) 0.32458(10) 0.73430(11) 0.0184(3) Uani 1 1 d . . . . .
C007 C 0.60139(13) 0.24880(10) 0.55334(11) 0.0194(3) Uani 1 1 d . . . . .
H007 H 0.5469 0.2381 0.4742 0.023 Uiso 1 1 calc R . . . .
C008 C 0.56119(12) 0.30794(10) 0.61953(11) 0.0176(3) Uani 1 1 d . . . . .
C009 C 0.43576(13) 0.35758(10) 0.57745(11) 0.0189(3) Uani 1 1 d . . . . .
H009 H 0.3926 0.3575 0.4911 0.023 Uiso 1 1 calc R . . . .
C00A C 0.76265(13) 0.28149(10) 0.78273(11) 0.0204(3) Uani 1 1 d . . . . .
H00A H 0.8173 0.2933 0.8616 0.025 Uiso 1 1 calc R . . . .
C00B C 0.24156(13) 0.25558(10) 0.56768(12) 0.0217(3) Uani 1 1 d . . . . .
C00C C 0.55039(13) 0.47889(10) 0.74352(12) 0.0200(3) Uani 1 1 d . . . . .
C00D C 0.43610(13) 0.46188(10) 0.62620(12) 0.0200(3) Uani 1 1 d . . . . .
H00D H 0.4279 0.5138 0.5687 0.024 Uiso 1 1 calc R . . . .
C00E C 0.34168(13) 0.32767(10) 0.62957(12) 0.0201(3) Uani 1 1 d . . . . .
H00E H 0.3911 0.3055 0.7111 0.024 Uiso 1 1 calc R . . . .
C00F C 0.21511(13) 0.19776(11) 0.47549(13) 0.0242(3) Uani 1 1 d . . . . .
H00F H 0.2608 0.1946 0.4288 0.029 Uiso 1 1 calc R . . . .
C00G C 0.10479(14) 0.14146(10) 0.46064(13) 0.0257(3) Uani 1 1 d . . . . .
C00H C 0.07276(14) 0.17018(11) 0.54489(13) 0.0280(3) Uani 1 1 d . . . . .
H00H H 0.0023 0.1456 0.5561 0.034 Uiso 1 1 calc R . . . .
C00I C 0.30651(13) 0.43751(10) 0.62981(12) 0.0230(3) Uani 1 1 d . . . . .
C00J C 0.93270(14) 0.17538(12) 0.76964(13) 0.0282(3) Uani 1 1 d . . . . .
H00B H 0.9261 0.1065 0.7484 0.042 Uiso 1 1 calc GR . . . .
H00C H 0.9683 0.1814 0.8540 0.042 Uiso 1 1 calc GR . . . .
H00G H 0.9883 0.2085 0.7408 0.042 Uiso 1 1 calc GR . . . .
C00K C 0.65582(15) 0.53508(11) 0.72888(13) 0.0277(3) Uani 1 1 d . . . . .
H00I H 0.7301 0.5393 0.8035 0.042 Uiso 1 1 calc GR . . . .
H00J H 0.6258 0.6007 0.7006 0.042 Uiso 1 1 calc GR . . . .
H00K H 0.6794 0.5014 0.6731 0.042 Uiso 1 1 calc GR . . . .
C00L C 0.40469(15) 0.47607(11) 0.84570(13) 0.0273(3) Uani 1 1 d . . . . .
H00L H 0.4317 0.4087 0.8717 0.033 Uiso 1 1 calc R . . . .
H00M H 0.3865 0.5091 0.9060 0.033 Uiso 1 1 calc R . . . .
C00M C 0.51112(15) 0.52941(11) 0.82928(12) 0.0254(3) Uani 1 1 d . . . . .
H00N H 0.4826 0.5962 0.8018 0.030 Uiso 1 1 calc R . . . .
H00O H 0.5858 0.5343 0.9048 0.030 Uiso 1 1 calc R . . . .
C00N C 0.28535(15) 0.47432(12) 0.73280(14) 0.0287(4) Uani 1 1 d . . . . .
H00P H 0.2500 0.5409 0.7157 0.034 Uiso 1 1 calc R . . . .
H00Q H 0.2213 0.4325 0.7428 0.034 Uiso 1 1 calc R . . . .
C00O C 0.19533(15) 0.46714(12) 0.51757(14) 0.0305(4) Uani 1 1 d . . . . .
H00R H 0.1927 0.5381 0.5106 0.046 Uiso 1 1 calc GR . . . .
H00S H 0.1157 0.4438 0.5180 0.046 Uiso 1 1 calc GR . . . .
H00T H 0.2061 0.4385 0.4519 0.046 Uiso 1 1 calc GR . . . .
C00P C 0.03890(16) 0.06751(12) 0.36882(16) 0.0366(4) Uani 1 1 d . . . . .
H00U H 0.0125 0.0975 0.2926 0.055 Uiso 1 1 calc GR . . . .
H00V H -0.0361 0.0430 0.3772 0.055 Uiso 1 1 calc GR . . . .
H00W H 0.0971 0.0136 0.3766 0.055 Uiso 1 1 calc GR . . . .


_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
O001 C006 1.3901(16) . ?
O001 C00C 1.4853(16) . ?
O002 C005 1.3737(16) . ?
O003 C00B 1.3716(17) . ?
O003 C00H 1.3771(18) . ?
C004 C005 1.4025(19) . ?
C004 C00A 1.394(2) . ?
C004 C00J 1.5014(19) . ?
C005 C007 1.3844(19) . ?
C006 C008 1.3907(18) . ?
C006 C00A 1.3820(19) . ?
C007 C008 1.3877(19) . ?
C008 C009 1.4880(18) . ?
C009 C00D 1.564(2) . ?
C009 C00E 1.5540(18) . ?
C00B C00E 1.4778(19) . ?
C00B C00F 1.344(2) . ?
C00C C00D 1.5429(19) . ?
C00C C00K 1.524(2) . ?
C00C C00M 1.5195(19) . ?
C00D C00I 1.5599(19) . ?
C00E C00I 1.566(2) . ?
C00F C00G 1.439(2) . ?
C00G C00H 1.337(2) . ?
C00G C00P 1.496(2) . ?
C00I C00N 1.522(2) . ?
C00I C00O 1.524(2) . ?
C00L C00M 1.525(2) . ?
C00L C00N 1.520(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
C006 O001 C00C 113.93(10) . . ?
C00B O003 C00H 106.03(11) . . ?
C005 C004 C00J 121.30(13) . . ?
C00A C004 C005 118.05(13) . . ?
C00A C004 C00J 120.64(12) . . ?
O002 C005 C004 116.55(12) . . ?
O002 C005 C007 122.70(12) . . ?
C007 C005 C004 120.75(12) . . ?
O001 C006 C008 118.80(12) . . ?
C00A C006 O001 120.14(12) . . ?
C00A C006 C008 121.06(12) . . ?
C005 C007 C008 120.83(12) . . ?
C006 C008 C009 116.17(12) . . ?
C007 C008 C006 118.50(12) . . ?
C007 C008 C009 125.33(12) . . ?
C008 C009 C00D 116.10(11) . . ?
C008 C009 C00E 118.72(11) . . ?
C00E C009 C00D 87.56(10) . . ?
C006 C00A C004 120.77(12) . . ?
O003 C00B C00E 115.37(12) . . ?
C00F C00B O003 109.93(12) . . ?
C00F C00B C00E 134.68(13) . . ?
O001 C00C C00D 111.03(11) . . ?
O001 C00C C00K 107.45(11) . . ?
O001 C00C C00M 103.99(10) . . ?
C00K C00C C00D 111.35(11) . . ?
C00M C00C C00D 111.85(12) . . ?
C00M C00C C00K 110.85(12) . . ?
C00C C00D C009 112.47(11) . . ?
C00C C00D C00I 116.66(11) . . ?
C00I C00D C009 88.48(10) . . ?
C009 C00E C00I 88.61(10) . . ?
C00B C00E C009 119.00(12) . . ?
C00B C00E C00I 120.16(11) . . ?
C00B C00F C00G 107.24(13) . . ?
C00F C00G C00P 127.02(14) . . ?
C00H C00G C00F 105.56(13) . . ?
C00H C00G C00P 127.41(14) . . ?
C00G C00H O003 111.23(13) . . ?
C00D C00I C00E 87.27(10) . . ?
C00N C00I C00D 117.53(12) . . ?
C00N C00I C00E 117.39(12) . . ?
C00N C00I C00O 109.97(12) . . ?
C00O C00I C00D 111.04(12) . . ?
C00O C00I C00E 111.98(12) . . ?
C00N C00L C00M 110.13(13) . . ?
C00C C00M C00L 112.62(12) . . ?
C00L C00N C00I 114.17(12) . . ?

_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 1.364
_oxdiff_exptl_absorpt_empirical_full_min 0.426
