# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_sam-1-tet-3p2
_database_code_depnum_ccdc_archive 'CCDC 2023107'
loop_
_audit_author_name
_audit_author_address
'Krishnan Venkatasubbaiah'
;National Institute of Science Education and Research(NISER)
India
;
_audit_update_record             
;
2020-08-13 deposited with the CCDC.	2021-01-13 downloaded from the CCDC.
;
_audit_creation_date             2019-12-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 O'
_chemical_formula_sum            'C15 H16 O'
_chemical_formula_weight         212.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C60 H56 O4 '
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                   8.9714(15)
_cell_length_b                   6.6608(7)
_cell_length_c                   19.405(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.551(15)
_cell_angle_gamma                90
_cell_volume                     1146.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2981
_cell_measurement_temperature    114(1)
_cell_measurement_theta_max      72.5770
_cell_measurement_theta_min      4.5500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.580
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51642
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46b (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1362
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.941
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13865
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_theta_full        66.592
_diffrn_reflns_theta_max         66.592
_diffrn_reflns_theta_min         4.609
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      114(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.941
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00 -10.00   0.50    4.50    --  -38.50 139.00   5.00  176
  2  ω    -93.00  -6.00   0.50    4.50    --  -38.50 130.00-168.00  174
  3  ω     28.00 102.00   0.50    4.50    --   47.81-130.00 118.00  148
  4  ω     32.00 107.00   0.50    4.50    --   47.81-139.00 -55.00  150
  5  ω     40.00 128.00   0.50   18.00    --  102.63-139.00 -55.00  176
  6  ω     39.00 121.00   0.50   18.00    --  102.63-130.00 118.00  164
  7  ω     86.00 166.00   0.50   18.00    --  102.63 139.00   5.00  160
  8  ω     92.00 167.00   0.50   18.00    --  102.63 130.00-168.00  150
  9  ω   -103.00 -15.00   0.50    4.50    --  -38.50 -77.00  30.00  176
 10  ω    -44.00  31.00   0.50    4.50    --  -38.50  19.00 -60.00  150
 11  ω   -101.00 -27.00   0.50    4.50    --  -38.50 -57.00 120.00  148
 12  ω     25.00 112.00   0.50    4.50    --   47.81  77.00-120.00  174
 13  ω     45.00 114.00   0.50    4.50    --   47.81  37.00   0.00  138
 14  ω     38.00 107.00   0.50   18.00    --  102.63 -45.00 -90.00  138
 15  ω     35.00 106.00   0.50   18.00    --  102.63 -30.00 120.00  142
 16  ω     34.00 111.00   0.50   18.00    --  102.63 -15.00 -60.00  154
 17  ω     94.00 168.00   0.50   18.00    --  102.63 125.00 150.00  148
 18  ω     38.00 107.00   0.50   18.00    --  102.63 -45.00  90.00  138
 19  ω     33.00 171.00   0.50   18.00    --  102.63   0.00-120.00  276
 20  ω     38.00 107.00   0.50   18.00    --  102.63 -45.00-180.00  138
 21  ω     98.00 167.00   0.50   18.00    --  102.63  45.00-120.00  138
 22  ω     38.00 118.00   0.50   18.00    --  102.63-125.00 150.00  160
 23  ω     40.00 116.00   0.50   18.00    --  102.63 -61.00  90.00  152
 24  ω     38.00 126.00   0.50   18.00    --  102.63 -77.00   0.00  176
 25  ω     38.00 118.00   0.50   18.00    --  102.63-125.00 -60.00  160
 26  ω     40.00 116.00   0.50   18.00    --  102.63 -61.00 120.00  152
 27  ω     38.00 126.00   0.50   18.00    --  102.63 -77.00 -90.00  176
 28  ω     94.00 168.00   0.50   18.00    --  102.63 125.00-120.00  148
 29  ω     90.00 165.00   0.50   18.00    --  102.63  61.00 -60.00  150
 30  ω     98.00 167.00   0.50   18.00    --  102.63  45.00 -90.00  138
 31  ω     40.00 116.00   0.50   18.00    --  102.63 -61.00-120.00  152
 32  ω     39.00 125.00   0.50   18.00    --  102.63-134.00-178.03  172
 33  ω     95.00 171.00   0.50   18.00    --  102.63  15.00 -30.00  152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Dual, Cu at home/near, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0315758000
_diffrn_orient_matrix_UB_12      -0.0611763000
_diffrn_orient_matrix_UB_13      0.0729333000
_diffrn_orient_matrix_UB_21      -0.1229495000
_diffrn_orient_matrix_UB_22      -0.1470782000
_diffrn_orient_matrix_UB_23      -0.0333279000
_diffrn_orient_matrix_UB_31      0.1188538000
_diffrn_orient_matrix_UB_32      -0.1675917000
_diffrn_orient_matrix_UB_33      0.0027112000
_diffrn_oxdiff_ac3_digest_frames 
;
01f2f0683f30fc2f87081b32fbe5d614440002693bf
;
_diffrn_oxdiff_ac3_digest_hkl    
;
015369af02c5ba0c7b6f240e510ebb328542de
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1406
_reflns_number_total             1899
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46b (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.280
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         1899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1201
_refine_ls_R_factor_gt           0.1022
_refine_ls_restrained_S_all      1.280
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2919
_refine_ls_wR_factor_ref         0.3190
_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 Ternary CH refined with riding coordinates:
 C12(H12), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C14(H14A,H14B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C6(H6), C7(H7)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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
O1 O 0.5133(3) 0.0601(3) 0.61178(12) 0.0576(8) Uani 1 1 d . . . . .
C4 C 0.2331(4) 0.4695(4) 0.43288(15) 0.0441(8) Uani 1 1 d . . . . .
C2 C 0.3814(3) 0.2658(4) 0.52537(15) 0.0436(8) Uani 1 1 d . . . . .
H2 H 0.4031 0.1804 0.4903 0.052 Uiso 1 1 calc R . . . .
C3 C 0.2973(4) 0.4304(4) 0.50653(15) 0.0441(8) Uani 1 1 d . . . . .
C1 C 0.4400(4) 0.2136(4) 0.59687(17) 0.0496(9) Uani 1 1 d . . . . .
C5 C 0.2405(4) 0.3228(5) 0.38094(17) 0.0504(8) Uani 1 1 d . . . . .
H5 H 0.2866 0.2003 0.3933 0.060 Uiso 1 1 calc R . . . .
C9 C 0.1612(4) 0.6526(4) 0.41256(17) 0.0536(9) Uani 1 1 d . . . . .
C8 C 0.1065(4) 0.6872(5) 0.34345(18) 0.0583(9) Uani 1 1 d . . . . .
H8 H 0.0641 0.8113 0.3303 0.070 Uiso 1 1 calc R . . . .
C6 C 0.1813(4) 0.3569(6) 0.31279(18) 0.0572(9) Uani 1 1 d . . . . .
H6 H 0.1861 0.2574 0.2796 0.069 Uiso 1 1 calc R . . . .
C7 C 0.1133(4) 0.5419(6) 0.29311(18) 0.0594(10) Uani 1 1 d . . . . .
H7 H 0.0733 0.5665 0.2469 0.071 Uiso 1 1 calc R . . . .
C12 C 0.2709(6) 0.5829(5) 0.56136(18) 0.0702(12) Uani 1 1 d . . . . .
H12 H 0.3658 0.6561 0.5620 0.084 Uiso 1 1 calc R . . . .
C15 C 0.2751(5) 0.6576(5) 0.68929(18) 0.0623(10) Uani 1 1 d . . . . .
H15A H 0.3410 0.7708 0.6883 0.093 Uiso 1 1 calc GR . . . .
H15B H 0.2955 0.5931 0.7339 0.093 Uiso 1 1 calc GR . . . .
H15C H 0.1722 0.7025 0.6814 0.093 Uiso 1 1 calc GR . . . .
C13 C 0.3009(6) 0.5107(7) 0.63300(19) 0.0841(15) Uani 1 1 d . . . . .
H13 H 0.2096 0.4296 0.6328 0.101 Uiso 1 1 calc R . . . .
C10 C 0.1466(7) 0.8110(5) 0.4668(2) 0.0790(14) Uani 1 1 d . . . . .
H10A H 0.2166 0.9188 0.4613 0.095 Uiso 1 1 calc R . . . .
H10B H 0.0456 0.8665 0.4578 0.095 Uiso 1 1 calc R . . . .
C14 C 0.4089(7) 0.3576(6) 0.6526(2) 0.0867(16) Uani 1 1 d . . . . .
H14A H 0.3759 0.2803 0.6899 0.104 Uiso 1 1 calc R . . . .
H14B H 0.5033 0.4216 0.6715 0.104 Uiso 1 1 calc R . . . .
C11 C 0.1738(8) 0.7445(8) 0.5367(2) 0.109(2) Uani 1 1 d . . . . .
H11A H 0.0759 0.7119 0.5492 0.131 Uiso 1 1 calc R . . . .
H11B H 0.2101 0.8606 0.5644 0.131 Uiso 1 1 calc 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 C1 1.227(4) . ?
C4 C3 1.482(4) . ?
C4 C5 1.413(4) . ?
C4 C9 1.408(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.350(4) . ?
C2 C1 1.451(5) . ?
C3 C12 1.515(4) . ?
C1 C14 1.502(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.369(5) . ?
C9 C8 1.377(5) . ?
C9 C10 1.510(4) . ?
C8 H8 0.9300 . ?
C8 C7 1.383(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.403(6) . ?
C7 H7 0.9300 . ?
C12 H12 0.9800 . ?
C12 C13 1.458(5) . ?
C12 C11 1.422(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 C13 1.510(4) . ?
C13 H13 0.9800 . ?
C13 C14 1.419(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.413(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

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
C5 C4 C3 120.9(3) . . ?
C9 C4 C3 121.2(3) . . ?
C9 C4 C5 117.9(3) . . ?
C3 C2 H2 117.9 . . ?
C3 C2 C1 124.2(3) . . ?
C1 C2 H2 117.9 . . ?
C4 C3 C12 118.7(3) . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 C12 119.6(3) . . ?
O1 C1 C2 122.0(3) . . ?
O1 C1 C14 120.9(3) . . ?
C2 C1 C14 117.1(3) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C9 C10 119.6(3) . . ?
C8 C9 C4 120.0(3) . . ?
C8 C9 C10 120.4(3) . . ?
C9 C8 H8 119.2 . . ?
C9 C8 C7 121.6(3) . . ?
C7 C8 H8 119.2 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0(3) . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 119.0(3) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C3 C12 H12 96.6 . . ?
C13 C12 C3 115.0(3) . . ?
C13 C12 H12 96.6 . . ?
C11 C12 C3 115.0(3) . . ?
C11 C12 H12 96.6 . . ?
C11 C12 C13 126.0(3) . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
C12 C13 C15 116.7(3) . . ?
C12 C13 H13 98.2 . . ?
C15 C13 H13 98.2 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 C15 116.4(3) . . ?
C14 C13 H13 98.2 . . ?
C9 C10 H10A 108.4 . . ?
C9 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 115.4(3) . . ?
C11 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C1 C14 H14A 108.0 . . ?
C1 C14 H14B 108.0 . . ?
C13 C14 C1 117.3(4) . . ?
C13 C14 H14A 108.0 . . ?
C13 C14 H14B 108.0 . . ?
H14A C14 H14B 107.2 . . ?
C12 C11 H11A 106.1 . . ?
C12 C11 H11B 106.1 . . ?
C10 C11 C12 124.7(4) . . ?
C10 C11 H11A 106.1 . . ?
C10 C11 H11B 106.1 . . ?
H11A C11 H11B 106.3 . . ?

_shelx_SHELXL_version_number     2014/7
_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 4.353
_oxdiff_exptl_absorpt_empirical_full_min 0.219
