# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
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data_n240104a
_database_code_depnum_ccdc_archive 'CCDC 2323662'
_audit_update_record             
;
2024-01-05 deposited with the CCDC.	2024-04-22 downloaded from the CCDC.
;
_audit_creation_date             2024-01-04
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 O4'
_chemical_formula_sum            'C19 H18 O4'
_chemical_formula_weight         310.33
_chemical_melting_point          ?
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                   13.6705(14)
_cell_length_b                   7.2456(7)
_cell_length_c                   16.9158(17)
_cell_angle_alpha                90
_cell_angle_beta                 105.335(2)
_cell_angle_gamma                90
_cell_volume                     1615.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4150
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.57
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1122 before and 0.0345 after correction. The Ratio of minimum to maximum transmission is 0.8989. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8941
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.008
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         2.497
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2336
_reflns_number_total             2836
_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       'SAINT V8.32B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.32B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.027
_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     208
_refine_ls_number_reflns         2836
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0565P)²+0.3192P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1088
_refine_ls_wR_factor_ref         0.1172
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C9(H9), C10(H10), C13(H13), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.79015(9) 0.13219(17) 0.40961(7) 0.0682(4) Uani 1 1 d . . . . .
O2 O 0.90592(9) 0.31557(18) 0.49172(7) 0.0685(4) Uani 1 1 d . . . . .
O3 O 1.00241(11) 0.4470(2) 0.24180(9) 0.0971(5) Uani 1 1 d . . . . .
O4 O 1.15446(10) 0.29258(19) 0.28619(8) 0.0785(4) Uani 1 1 d . . . . .
C1 C 1.08676(16) 0.3784(3) 0.21715(12) 0.0800(6) Uani 1 1 d . . . . .
H1A H 1.120885 0.478681 0.197313 0.096 Uiso 1 1 calc R . . . .
H1B H 1.064394 0.289480 0.173212 0.096 Uiso 1 1 calc R . . . .
C2 C 1.01082(12) 0.3749(2) 0.31804(10) 0.0571(4) Uani 1 1 d . . . . .
C3 C 1.10121(11) 0.2830(2) 0.34471(10) 0.0532(4) Uani 1 1 d . . . . .
C4 C 1.12789(12) 0.1984(2) 0.41896(10) 0.0581(4) Uani 1 1 d . . . . .
H4 H 1.189367 0.136524 0.437061 0.070 Uiso 1 1 calc R . . . .
C5 C 1.05955(12) 0.2081(2) 0.46685(10) 0.0574(4) Uani 1 1 d . . . . .
H5 H 1.075092 0.151561 0.518021 0.069 Uiso 1 1 calc R . . . .
C6 C 0.96970(12) 0.3001(2) 0.43922(9) 0.0525(4) Uani 1 1 d . . . . .
C7 C 0.94249(12) 0.3872(2) 0.36365(10) 0.0583(4) Uani 1 1 d . . . . .
H7 H 0.881396 0.450100 0.345198 0.070 Uiso 1 1 calc R . . . .
C8 C 0.81381(12) 0.2317(2) 0.46829(9) 0.0519(4) Uani 1 1 d . . . . .
C9 C 0.75300(13) 0.2764(2) 0.52477(10) 0.0579(4) Uani 1 1 d . . . . .
H9 H 0.780612 0.347957 0.570919 0.069 Uiso 1 1 calc R . . . .
C10 C 0.65894(11) 0.2155(2) 0.51062(9) 0.0499(4) Uani 1 1 d . . . . .
H10 H 0.637213 0.143348 0.463797 0.060 Uiso 1 1 calc R . . . .
C11 C 0.58301(11) 0.24335(18) 0.55682(9) 0.0452(3) Uani 1 1 d . . . . .
C12 C 0.60730(12) 0.2499(2) 0.64318(9) 0.0528(4) Uani 1 1 d . . . . .
C13 C 0.52952(14) 0.2657(2) 0.68128(10) 0.0611(4) Uani 1 1 d . . . . .
H13 H 0.545768 0.268280 0.738244 0.073 Uiso 1 1 calc R . . . .
C14 C 0.42884(14) 0.2776(2) 0.63788(11) 0.0639(4) Uani 1 1 d . . . . .
C15 C 0.40678(12) 0.2752(2) 0.55332(11) 0.0595(4) Uani 1 1 d . . . . .
H15 H 0.339516 0.287029 0.523187 0.071 Uiso 1 1 calc R . . . .
C16 C 0.48083(11) 0.25580(18) 0.51158(9) 0.0488(4) Uani 1 1 d . . . . .
C17 C 0.45025(13) 0.2526(2) 0.41919(9) 0.0613(4) Uani 1 1 d . . . . .
H17A H 0.484212 0.350561 0.398898 0.092 Uiso 1 1 d R . . . .
H17B H 0.378202 0.268991 0.399488 0.092 Uiso 1 1 d R . . . .
H17C H 0.469032 0.136251 0.400338 0.092 Uiso 1 1 d R . . . .
C18 C 0.71445(15) 0.2361(3) 0.69639(10) 0.0802(6) Uani 1 1 d . . . . .
H18A H 0.748020 0.134106 0.678509 0.120 Uiso 1 1 d R . . . .
H18B H 0.713430 0.217136 0.752329 0.120 Uiso 1 1 d R . . . .
H18C H 0.750160 0.348196 0.692249 0.120 Uiso 1 1 d R . . . .
C19 C 0.34550(18) 0.2916(4) 0.68117(16) 0.1042(8) Uani 1 1 d . . . . .
H19A H 0.335122 0.173087 0.702977 0.156 Uiso 1 1 d R . . . .
H19B H 0.283872 0.331207 0.642967 0.156 Uiso 1 1 d R . . . .
H19C H 0.364632 0.379417 0.725057 0.156 Uiso 1 1 d R . . . .


_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 C8 1.2001(18) . ?
O2 C6 1.4041(18) . ?
O2 C8 1.3592(19) . ?
O3 C1 1.416(2) . ?
O3 C2 1.3679(19) . ?
O4 C1 1.427(2) . ?
O4 C3 1.3769(18) . ?
C2 C3 1.371(2) . ?
C2 C7 1.363(2) . ?
C3 C4 1.358(2) . ?
C4 C5 1.391(2) . ?
C5 C6 1.367(2) . ?
C6 C7 1.385(2) . ?
C8 C9 1.459(2) . ?
C9 C10 1.320(2) . ?
C10 C11 1.469(2) . ?
C11 C12 1.411(2) . ?
C11 C16 1.407(2) . ?
C12 C13 1.386(2) . ?
C12 C18 1.506(2) . ?
C13 C14 1.381(3) . ?
C14 C15 1.382(2) . ?
C14 C19 1.512(2) . ?
C15 C16 1.386(2) . ?
C16 C17 1.507(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
C8 O2 C6 117.53(12) . . ?
C2 O3 C1 105.76(14) . . ?
C3 O4 C1 104.99(13) . . ?
O3 C1 O4 108.33(14) . . ?
O3 C2 C3 109.85(14) . . ?
C7 C2 O3 127.55(15) . . ?
C7 C2 C3 122.60(14) . . ?
C2 C3 O4 109.93(14) . . ?
C4 C3 O4 128.61(15) . . ?
C4 C3 C2 121.46(15) . . ?
C3 C4 C5 117.29(14) . . ?
C6 C5 C4 120.45(14) . . ?
C5 C6 O2 118.35(14) . . ?
C5 C6 C7 122.38(14) . . ?
C7 C6 O2 119.16(14) . . ?
C2 C7 C6 115.82(14) . . ?
O1 C8 O2 122.42(14) . . ?
O1 C8 C9 126.81(14) . . ?
O2 C8 C9 110.75(13) . . ?
C10 C9 C8 120.24(15) . . ?
C9 C10 C11 130.49(15) . . ?
C12 C11 C10 123.34(14) . . ?
C16 C11 C10 117.33(13) . . ?
C16 C11 C12 119.27(14) . . ?
C11 C12 C18 122.81(15) . . ?
C13 C12 C11 119.01(15) . . ?
C13 C12 C18 118.16(15) . . ?
C14 C13 C12 122.50(15) . . ?
C13 C14 C15 117.62(15) . . ?
C13 C14 C19 121.30(17) . . ?
C15 C14 C19 121.08(18) . . ?
C14 C15 C16 122.67(15) . . ?
C11 C16 C17 121.74(14) . . ?
C15 C16 C11 118.90(14) . . ?
C15 C16 C17 119.35(14) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
