# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_test1_a
_database_code_depnum_ccdc_archive 'CCDC 1990107'
loop_
_audit_author_name
_audit_author_address
'Sanu Saha'
;Indian Association for the Cultivation of Science
India
;
_audit_update_record             
;
2020-03-13 deposited with the CCDC.	2020-09-18 downloaded from the CCDC.
;
_audit_creation_date             2020-03-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H30 O4'
_chemical_formula_sum            'C15 H30 O4'
_chemical_formula_weight         274.39
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.380(12)
_cell_length_b                   5.067(7)
_cell_length_c                   19.58(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.25(4)
_cell_angle_gamma                90
_cell_volume                     829(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    632
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      24.68
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.3468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1331 before and 0.0768 after correction.
The Ratio of minimum to maximum transmission is 0.4653.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             304
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1653
_diffrn_reflns_av_unetI/netI     0.3293
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4883
_diffrn_reflns_point_group_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.437
_diffrn_ambient_temperature      301.57
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.988
_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_standards_number         0
_reflns_Friedel_coverage         0.655
_reflns_Friedel_fraction_full    0.808
_reflns_Friedel_fraction_max     0.830
_reflns_number_gt                805
_reflns_number_total             2666
_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 V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 
;
 Flack x determined using 182 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -3.3(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.938
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2666
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.3111
_refine_ls_R_factor_gt           0.1285
_refine_ls_restrained_S_all      0.939
_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)+(0.1380P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2632
_refine_ls_wR_factor_ref         0.3464
_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, All O(H) groups
2. Restrained distances
 C00D-C009 \\sim C00D-C00C
 with sigma of 0.02
 C00G-C00F \\sim C00H-C00F
 with sigma of 0.02
 C00C-C00A \\sim C00D-C00C
 with sigma of 0.02
 C009-C008 \\sim C00E-C008
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C005) = Uanis(C007)
Uanis(C00A) = Uanis(C00I)
Uanis(C008) = Uanis(C007)
Uanis(C00F) = Uanis(C00H)
4.a Ternary CH refined with riding coordinates:
 C005(H005), C007(H007), C008(H008)
4.b Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C00A(H00C,H00D), C00B(H00E,H00F), C00C(H00G,H00H), C00D(H00I,
 H00J), C00F(H00N,H00O), C00G(H00P,H00Q), C00H(H00R,H00S), C00I(H00T,H00U)
4.c Idealised Me refined as rotating group:
 C00E(H00K,H00L,H00M), C00J(H00V,H00W,H00X)
4.d Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002), O004(H004)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.2768(12) 0.2045(18) 0.8726(7) 0.075(4) Uani 1 1 d . . . . .
H001 H 0.2224 0.1297 0.8999 0.113 Uiso 1 1 calc GR . . . .
O002 O 0.4689(12) 0.5219(16) 0.9717(6) 0.067(4) Uani 1 1 d . . . . .
H002 H 0.4671 0.3604 0.9742 0.101 Uiso 1 1 calc GR . . . .
O003 O 0.0828(10) 0.3655(17) 0.9642(6) 0.059(3) Uani 1 1 d . . . . .
O004 O 0.1266(11) 0.7919(18) 0.9436(6) 0.069(4) Uani 1 1 d . . . . .
H004 H 0.0471 0.8129 0.9650 0.103 Uiso 1 1 calc GR . . . .
C005 C 0.4308(15) 0.599(2) 0.9040(8) 0.044(2) Uani 1 1 d . . . . .
H005 H 0.4220 0.7921 0.9025 0.052 Uiso 1 1 calc R . . . .
C006 C 0.1498(17) 0.533(3) 0.9337(9) 0.055(4) Uani 1 1 d . . . . .
C007 C 0.2646(16) 0.478(2) 0.8809(9) 0.044(2) Uani 1 1 d . . . . .
H007 H 0.2246 0.5578 0.8374 0.052 Uiso 1 1 calc R . . . .
C008 C 0.5569(13) 0.515(2) 0.8578(7) 0.044(2) Uani 1 1 d D . . . .
H008 H 0.5628 0.3218 0.8585 0.052 Uiso 1 1 calc R . . . .
C009 C 0.5223(17) 0.605(3) 0.7826(8) 0.070(5) Uani 1 1 d D . . . .
H00A H 0.4104 0.5708 0.7691 0.084 Uiso 1 1 calc R . . . .
H00B H 0.5384 0.7943 0.7804 0.084 Uiso 1 1 calc R . . . .
C00A C 0.6986(19) 0.467(4) 0.6111(10) 0.085(4) Uani 1 1 d D . . . .
H00C H 0.6773 0.2787 0.6076 0.102 Uiso 1 1 calc R . . . .
H00D H 0.8089 0.4890 0.6289 0.102 Uiso 1 1 calc R . . . .
C00B C 0.6775(18) 0.587(3) 0.5414(9) 0.073(5) Uani 1 1 d . . . . .
H00E H 0.6956 0.7754 0.5449 0.087 Uiso 1 1 calc R . . . .
H00F H 0.5684 0.5589 0.5227 0.087 Uiso 1 1 calc R . . . .
C00C C 0.5913(19) 0.585(4) 0.6603(9) 0.076(5) Uani 1 1 d D . . . .
H00G H 0.4809 0.5513 0.6442 0.091 Uiso 1 1 calc R . . . .
H00H H 0.6068 0.7747 0.6613 0.091 Uiso 1 1 calc R . . . .
C00D C 0.6201(19) 0.479(3) 0.7323(10) 0.083(7) Uani 1 1 d D . . . .
H00I H 0.5981 0.2906 0.7316 0.099 Uiso 1 1 calc R . . . .
H00J H 0.7322 0.5019 0.7472 0.099 Uiso 1 1 calc R . . . .
C00E C 0.7255(16) 0.627(4) 0.8848(10) 0.103(8) Uani 1 1 d D . . . .
H00K H 0.7334 0.8090 0.8714 0.155 Uiso 1 1 calc GR . . . .
H00L H 0.8084 0.5273 0.8654 0.155 Uiso 1 1 calc GR . . . .
H00M H 0.7374 0.6144 0.9338 0.155 Uiso 1 1 calc GR . . . .
C00F C 0.889(2) 0.472(4) 0.3759(10) 0.111(6) Uani 1 1 d D . . . .
H00N H 0.8690 0.2834 0.3725 0.134 Uiso 1 1 calc R . . . .
H00O H 0.9980 0.4948 0.3959 0.134 Uiso 1 1 calc R . . . .
C00G C 0.778(2) 0.588(4) 0.4222(10) 0.095(6) Uani 1 1 d D . . . .
H00P H 0.6696 0.5652 0.4023 0.114 Uiso 1 1 calc R . . . .
H00Q H 0.7987 0.7763 0.4258 0.114 Uiso 1 1 calc R . . . .
C00H C 0.878(2) 0.586(5) 0.3057(11) 0.111(6) Uani 1 1 d D . . . .
H00R H 0.8970 0.7747 0.3095 0.134 Uiso 1 1 calc R . . . .
H00S H 0.7689 0.5626 0.2861 0.134 Uiso 1 1 calc R . . . .
C00I C 0.791(2) 0.470(4) 0.4936(10) 0.085(4) Uani 1 1 d . . . . .
H00T H 0.7708 0.2817 0.4899 0.102 Uiso 1 1 calc R . . . .
H00U H 0.8994 0.4932 0.5135 0.102 Uiso 1 1 calc R . . . .
C00J C 0.990(3) 0.473(5) 0.2572(11) 0.138(10) Uani 1 1 d . . . . .
H00V H 1.0968 0.4737 0.2784 0.207 Uiso 1 1 calc GR . . . .
H00W H 0.9859 0.5781 0.2163 0.207 Uiso 1 1 calc GR . . . .
H00X H 0.9586 0.2954 0.2458 0.207 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 H001 0.8200 . ?
O001 C007 1.401(13) . ?
O002 H002 0.8200 . ?
O002 C005 1.396(16) . ?
O003 C006 1.202(14) . ?
O004 H004 0.8200 . ?
O004 C006 1.341(16) . ?
C005 H005 0.9800 . ?
C005 C007 1.559(18) . ?
C005 C008 1.503(17) . ?
C006 C007 1.489(18) . ?
C007 H007 0.9800 . ?
C008 H008 0.9800 . ?
C008 C009 1.550(16) . ?
C008 C00E 1.578(15) . ?
C009 H00A 0.9700 . ?
C009 H00B 0.9700 . ?
C009 C00D 1.474(15) . ?
C00A H00C 0.9700 . ?
C00A H00D 0.9700 . ?
C00A C00B 1.49(2) . ?
C00A C00C 1.492(16) . ?
C00B H00E 0.9700 . ?
C00B H00F 0.9700 . ?
C00B C00I 1.50(2) . ?
C00C H00G 0.9700 . ?
C00C H00H 0.9700 . ?
C00C C00D 1.512(17) . ?
C00D H00I 0.9700 . ?
C00D H00J 0.9700 . ?
C00E H00K 0.9600 . ?
C00E H00L 0.9600 . ?
C00E H00M 0.9600 . ?
C00F H00N 0.9700 . ?
C00F H00O 0.9700 . ?
C00F C00G 1.472(18) . ?
C00F C00H 1.49(2) . ?
C00G H00P 0.9700 . ?
C00G H00Q 0.9700 . ?
C00G C00I 1.52(2) . ?
C00H H00R 0.9700 . ?
C00H H00S 0.9700 . ?
C00H C00J 1.50(3) . ?
C00I H00T 0.9700 . ?
C00I H00U 0.9700 . ?
C00J H00V 0.9600 . ?
C00J H00W 0.9600 . ?
C00J H00X 0.9600 . ?

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
C007 O001 H001 109.5 . . ?
C005 O002 H002 109.5 . . ?
C006 O004 H004 109.5 . . ?
O002 C005 H005 108.7 . . ?
O002 C005 C007 107.5(11) . . ?
O002 C005 C008 111.7(12) . . ?
C007 C005 H005 108.7 . . ?
C008 C005 H005 108.7 . . ?
C008 C005 C007 111.5(11) . . ?
O003 C006 O004 122.7(13) . . ?
O003 C006 C007 124.2(13) . . ?
O004 C006 C007 113.1(10) . . ?
O001 C007 C005 110.6(11) . . ?
O001 C007 C006 108.8(11) . . ?
O001 C007 H007 109.3 . . ?
C005 C007 H007 109.3 . . ?
C006 C007 C005 109.5(13) . . ?
C006 C007 H007 109.3 . . ?
C005 C008 H008 108.2 . . ?
C005 C008 C009 113.5(11) . . ?
C005 C008 C00E 110.4(13) . . ?
C009 C008 H008 108.2 . . ?
C009 C008 C00E 108.2(11) . . ?
C00E C008 H008 108.2 . . ?
C008 C009 H00A 108.4 . . ?
C008 C009 H00B 108.4 . . ?
H00A C009 H00B 107.4 . . ?
C00D C009 C008 115.7(14) . . ?
C00D C009 H00A 108.4 . . ?
C00D C009 H00B 108.4 . . ?
H00C C00A H00D 107.8 . . ?
C00B C00A H00C 109.0 . . ?
C00B C00A H00D 109.0 . . ?
C00C C00A H00C 109.0 . . ?
C00C C00A H00D 109.0 . . ?
C00C C00A C00B 113.0(16) . . ?
C00A C00B H00E 109.3 . . ?
C00A C00B H00F 109.3 . . ?
C00A C00B C00I 111.8(14) . . ?
H00E C00B H00F 107.9 . . ?
C00I C00B H00E 109.3 . . ?
C00I C00B H00F 109.3 . . ?
C00A C00C H00G 108.9 . . ?
C00A C00C H00H 108.9 . . ?
C00A C00C C00D 113.3(16) . . ?
H00G C00C H00H 107.7 . . ?
C00D C00C H00G 108.9 . . ?
C00D C00C H00H 108.9 . . ?
C009 C00D C00C 114.1(15) . . ?
C009 C00D H00I 108.7 . . ?
C009 C00D H00J 108.7 . . ?
C00C C00D H00I 108.7 . . ?
C00C C00D H00J 108.7 . . ?
H00I C00D H00J 107.6 . . ?
C008 C00E H00K 109.5 . . ?
C008 C00E H00L 109.5 . . ?
C008 C00E H00M 109.5 . . ?
H00K C00E H00L 109.5 . . ?
H00K C00E H00M 109.5 . . ?
H00L C00E H00M 109.5 . . ?
H00N C00F H00O 107.6 . . ?
C00G C00F H00N 108.7 . . ?
C00G C00F H00O 108.7 . . ?
C00G C00F C00H 114(2) . . ?
C00H C00F H00N 108.7 . . ?
C00H C00F H00O 108.7 . . ?
C00F C00G H00P 108.8 . . ?
C00F C00G H00Q 108.8 . . ?
C00F C00G C00I 113.9(17) . . ?
H00P C00G H00Q 107.7 . . ?
C00I C00G H00P 108.8 . . ?
C00I C00G H00Q 108.8 . . ?
C00F C00H H00R 108.4 . . ?
C00F C00H H00S 108.4 . . ?
C00F C00H C00J 116(2) . . ?
H00R C00H H00S 107.4 . . ?
C00J C00H H00R 108.4 . . ?
C00J C00H H00S 108.4 . . ?
C00B C00I C00G 114.4(16) . . ?
C00B C00I H00T 108.7 . . ?
C00B C00I H00U 108.7 . . ?
C00G C00I H00T 108.7 . . ?
C00G C00I H00U 108.7 . . ?
H00T C00I H00U 107.6 . . ?
C00H C00J H00V 109.5 . . ?
C00H C00J H00W 109.5 . . ?
C00H C00J H00X 109.5 . . ?
H00V C00J H00W 109.5 . . ?
H00V C00J H00X 109.5 . . ?
H00W C00J H00X 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
