# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_mo_gs_ab_2_219_1_0m
_database_code_depnum_ccdc_archive 'CCDC 2237742'
loop_
_audit_author_name
_audit_author_address
Ramanababu
;Indian Institute of Technology Hyderabad
India
;
_audit_update_record             
;
2023-01-24 deposited with the CCDC.	2023-02-10 downloaded from the CCDC.
;
_audit_creation_date             2023-01-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H20 O'
_chemical_formula_sum            'C14 H20 O'
_chemical_formula_weight         204.30
_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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+1/4, x+3/4, z+3/4'
'y+1/4, -x+1/4, z+1/4'
'-x, -y+1/2, z'
'x+1/2, y+1/2, z+1/2'
'-y+3/4, x+5/4, z+5/4'
'y+3/4, -x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'-x, -y, -z'
'y-1/4, -x-3/4, -z-3/4'
'-y-1/4, x-1/4, -z-1/4'
'x, y-1/2, -z'
'-x+1/2, -y+1/2, -z+1/2'
'y+1/4, -x-1/4, -z-1/4'
'-y+1/4, x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'

_cell_length_a                   19.065(2)
_cell_length_b                   19.065(2)
_cell_length_c                   13.900(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5052.3(15)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3842
_cell_measurement_temperature    298
_cell_measurement_theta_max      23.39
_cell_measurement_theta_min      2.80
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6595
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1063 before and 0.0684 after correction.
The Ratio of minimum to maximum transmission is 0.8846.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.074
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.153
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            21267
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_min         1.813
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1591
_reflns_number_total             2790
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       0.0045(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2790
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0574
_refine_ls_restrained_S_all      1.038
_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)+(0.0724P)²+2.0147P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1756
_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 Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C9(H9A,H9B), C8(H8A,H8B), C12(H12A,H12B),
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C4(H4), C3(H3)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.54534(9) 0.83989(7) 0.65112(10) 0.0593(4) Uani 1 1 d . . . . .
C13 C 0.57498(15) 0.95979(15) 0.78071(17) 0.0890(8) Uani 1 1 d . . . . .
H13A H 0.579275 1.006083 0.809060 0.107 Uiso 1 1 calc R U . . .
H13B H 0.547228 0.930582 0.823330 0.107 Uiso 1 1 calc R U . . .
C14 C 0.54122(11) 0.96432(10) 0.68312(13) 0.0554(5) Uani 1 1 d . . . . .
H14A H 0.549521 1.009913 0.654326 0.067 Uiso 1 1 calc R U . . .
H14B H 0.491022 0.956713 0.687755 0.067 Uiso 1 1 calc R U . . .
C10 C 0.57591(9) 0.90625(9) 0.62348(13) 0.0473(5) Uani 1 1 d . . . . .
C9 C 0.56792(11) 0.91717(10) 0.51574(13) 0.0550(5) Uani 1 1 d . . . . .
H9A H 0.587902 0.962337 0.498990 0.066 Uiso 1 1 calc R U . . .
H9B H 0.518308 0.918808 0.500399 0.066 Uiso 1 1 calc R U . . .
C8 C 0.60253(13) 0.86076(12) 0.45345(14) 0.0701(7) Uani 1 1 d . . . . .
H8A H 0.652219 0.858825 0.468192 0.084 Uiso 1 1 calc R U . . .
H8B H 0.582315 0.815465 0.468991 0.084 Uiso 1 1 calc R U . . .
C5 C 0.59319(12) 0.87477(11) 0.34749(14) 0.0585(6) Uani 1 1 d . . . . .
C6 C 0.64268(13) 0.91121(12) 0.29611(16) 0.0684(6) Uani 1 1 d . . . . .
H6 H 0.683027 0.926804 0.327051 0.082 Uiso 1 1 calc R U . . .
C7 C 0.63377(15) 0.92526(12) 0.19899(17) 0.0771(7) Uani 1 1 d . . . . .
H7 H 0.668362 0.949893 0.166072 0.092 Uiso 1 1 calc R U . . .
C2 C 0.57533(15) 0.90372(13) 0.15073(16) 0.0724(7) Uani 1 1 d . . . . .
C1 C 0.5653(2) 0.91976(17) 0.04465(18) 0.1210(13) Uani 1 1 d . . . . .
H1A H 0.604356 0.901555 0.008854 0.182 Uiso 1 1 calc R U . . .
H1B H 0.562522 0.969601 0.035630 0.182 Uiso 1 1 calc R U . . .
H1C H 0.522788 0.898263 0.022380 0.182 Uiso 1 1 calc R U . . .
C4 C 0.53458(13) 0.85277(13) 0.29859(17) 0.0736(7) Uani 1 1 d . . . . .
H4 H 0.500149 0.827625 0.331112 0.088 Uiso 1 1 calc R U . . .
C3 C 0.52587(15) 0.86730(14) 0.20211(18) 0.0819(8) Uani 1 1 d . . . . .
H3 H 0.485432 0.852011 0.171114 0.098 Uiso 1 1 calc R U . . .
C12 C 0.64571(16) 0.92818(19) 0.7650(2) 0.1150(12) Uani 1 1 d . . . . .
H12A H 0.651764 0.887557 0.806140 0.138 Uiso 1 1 calc R U . . .
H12B H 0.681994 0.962030 0.780397 0.138 Uiso 1 1 calc R U . . .
C11 C 0.65110(10) 0.90693(12) 0.66117(15) 0.0614(6) Uani 1 1 d . . . . .
H11A H 0.672143 0.860796 0.655390 0.074 Uiso 1 1 calc R U . . .
H11B H 0.679395 0.940258 0.625482 0.074 Uiso 1 1 calc R U . . .
H1 H 0.507(2) 0.833(2) 0.633(3) 0.179(19) Uiso 1 1 d . . . . .


_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 C10 1.445(2) . ?
O1 H1 0.78(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.504(3) . ?
C13 C12 1.493(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C10 1.533(3) . ?
C10 C9 1.520(2) . ?
C10 C11 1.526(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.530(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C5 1.507(3) . ?
C5 C6 1.372(3) . ?
C5 C4 1.374(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.387(3) . ?
C7 H7 0.9300 . ?
C7 C2 1.364(3) . ?
C2 C1 1.518(3) . ?
C2 C3 1.372(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C3 1.379(3) . ?
C3 H3 0.9300 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.502(3) . ?
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
C10 O1 H1 117(3) . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 H13A 110.5 . . ?
C14 C13 H13B 110.5 . . ?
C12 C13 H13A 110.5 . . ?
C12 C13 H13B 110.5 . . ?
C12 C13 C14 106.1(2) . . ?
C13 C14 H14A 110.7 . . ?
C13 C14 H14B 110.7 . . ?
C13 C14 C10 105.17(17) . . ?
H14A C14 H14B 108.8 . . ?
C10 C14 H14A 110.7 . . ?
C10 C14 H14B 110.7 . . ?
O1 C10 C14 108.33(15) . . ?
O1 C10 C9 109.98(15) . . ?
O1 C10 C11 107.15(16) . . ?
C9 C10 C14 113.00(15) . . ?
C9 C10 C11 115.55(16) . . ?
C11 C10 C14 102.33(15) . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C10 C9 C8 114.71(16) . . ?
H9A C9 H9B 107.6 . . ?
C8 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
C5 C8 C9 112.17(17) . . ?
C5 C8 H8A 109.2 . . ?
C5 C8 H8B 109.2 . . ?
C6 C5 C8 121.1(2) . . ?
C6 C5 C4 117.2(2) . . ?
C4 C5 C8 121.7(2) . . ?
C5 C6 H6 119.3 . . ?
C5 C6 C7 121.3(2) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 119.3 . . ?
C2 C7 C6 121.4(2) . . ?
C2 C7 H7 119.3 . . ?
C7 C2 C1 121.3(3) . . ?
C7 C2 C3 117.3(2) . . ?
C3 C2 C1 121.4(3) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C5 C4 H4 119.4 . . ?
C5 C4 C3 121.2(2) . . ?
C3 C4 H4 119.4 . . ?
C2 C3 C4 121.7(2) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C13 C12 H12A 110.1 . . ?
C13 C12 H12B 110.1 . . ?
C13 C12 C11 108.15(19) . . ?
H12A C12 H12B 108.4 . . ?
C11 C12 H12A 110.1 . . ?
C11 C12 H12B 110.1 . . ?
C10 C11 H11A 110.6 . . ?
C10 C11 H11B 110.6 . . ?
C12 C11 C10 105.53(18) . . ?
C12 C11 H11A 110.6 . . ?
C12 C11 H11B 110.6 . . ?
H11A C11 H11B 108.8 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C10 C9 C8 -59.5(2) . . . . ?
O1 C10 C11 C12 -82.2(2) . . . . ?
C13 C14 C10 O1 77.4(2) . . . . ?
C13 C14 C10 C9 -160.49(19) . . . . ?
C13 C14 C10 C11 -35.6(2) . . . . ?
C13 C12 C11 C10 -16.5(3) . . . . ?
C14 C13 C12 C11 -6.0(3) . . . . ?
C14 C10 C9 C8 179.35(18) . . . . ?
C14 C10 C11 C12 31.7(2) . . . . ?
C10 C9 C8 C5 -179.62(19) . . . . ?
C9 C10 C11 C12 154.9(2) . . . . ?
C9 C8 C5 C6 92.9(3) . . . . ?
C9 C8 C5 C4 -86.0(3) . . . . ?
C8 C5 C6 C7 -178.9(2) . . . . ?
C8 C5 C4 C3 178.5(2) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
C5 C4 C3 C2 0.5(4) . . . . ?
C6 C5 C4 C3 -0.5(3) . . . . ?
C6 C7 C2 C1 179.4(2) . . . . ?
C6 C7 C2 C3 -0.3(4) . . . . ?
C7 C2 C3 C4 -0.1(4) . . . . ?
C1 C2 C3 C4 -179.8(2) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C12 C13 C14 C10 26.1(3) . . . . ?
C11 C10 C9 C8 62.0(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'NYLON LOOP'
_olex2_submission_special_instructions 'No special instructions were received'
