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

data_raf_rsr_163_a_autored
_database_code_depnum_ccdc_archive 'CCDC 2235974'
loop_
_audit_author_name
_audit_author_address
'Darshan Mhatre'
;Indian Institute of technology Bombay
India
;
_audit_update_record             
;
2023-01-13 deposited with the CCDC.	2023-12-13 downloaded from the CCDC.
;
_audit_creation_date             2023-01-05
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H18 O4'
_chemical_formula_sum            'C13 H18 O4'
_chemical_formula_weight         238.27
_chemical_absolute_configuration unk
_chemical_melting_point          152-154
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                   7.5355(3)
_cell_length_b                   7.5626(2)
_cell_length_c                   11.2958(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.257(3)
_cell_angle_gamma                90
_cell_volume                     626.57(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4214
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.3300
_cell_measurement_theta_min      1.8610
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'Yellow Solid'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.106
_exptl_crystal_size_min          0.089
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1451
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12140
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         1.852
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.81  15.69   0.50    4.00    --   -9.84 -59.25-123.92  233
  2  φ    -90.56  13.44   0.50    4.00  81.02  -9.84  31.50    --   208
  3  ω    -65.46   0.04   0.50    4.00    --  -19.34  94.56   1.16  131
  4  ω   -100.81  15.69   0.50    4.00    --   -9.84 -59.25  92.08  233
  5  ω   -100.81  15.69   0.50    4.00    --   -9.84 -59.25 164.08  233
  6  φ    166.27 350.27   0.50    4.00   6.61  -9.84 -31.50    --   368
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0070589000
_diffrn_orient_matrix_UB_12      -0.0199144000
_diffrn_orient_matrix_UB_13      -0.0601098000
_diffrn_orient_matrix_UB_21      0.0884919000
_diffrn_orient_matrix_UB_22      -0.0350976000
_diffrn_orient_matrix_UB_23      0.0229587000
_diffrn_orient_matrix_UB_31      -0.0383565000
_diffrn_orient_matrix_UB_32      -0.0846609000
_diffrn_orient_matrix_UB_33      0.0046372000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\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         0.846
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2051
_reflns_number_total             2191
_reflns_odcompleteness_completeness 78.32
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.72
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.233
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 862 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.048
_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)+(0.0825P)²+0.0318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1294
_refine_ls_wR_factor_ref         0.1341
_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.a Ternary CH refined with riding coordinates:
 C005(H005), C008(H008), C00D(H00E)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00C,H00D), C00E(H00F,H00G), C00G(H00K,H00L), C00H(H00M,H00N)
2.c X=CH2 refined with riding coordinates:
 C009(H00A,H00B)
2.d Idealised Me refined as rotating group:
 C00F(H00H,H00I,H00J)
2.e Idealised tetrahedral OH refined as rotating group:
 O001(H001), O002(H002)
;
_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
O001 O 0.5809(4) 0.8449(3) 0.6136(2) 0.0321(6) Uani 1 1 d . . . . .
H001 H 0.496162 0.810422 0.556285 0.048 Uiso 1 1 calc GR . . . .
O002 O 0.6654(3) 0.1913(3) 0.58121(18) 0.0258(6) Uani 1 1 d . . . . .
H002 H 0.639058 0.086190 0.593999 0.039 Uiso 1 1 calc GR . . . .
O003 O 0.8822(3) 0.6924(3) 0.79351(18) 0.0270(6) Uani 1 1 d . . . . .
O004 O 1.1284(3) 0.7173(4) 0.7172(2) 0.0370(7) Uani 1 1 d . . . . .
C005 C 0.7008(4) 0.6161(4) 0.7603(3) 0.0205(7) Uani 1 1 d . . . . .
H005 H 0.675300 0.550708 0.831575 0.025 Uiso 1 1 calc R . . . .
C006 C 0.9790(5) 0.6558(4) 0.7100(3) 0.0243(7) Uani 1 1 d . . . . .
C007 C 0.8733(4) 0.5334(4) 0.6170(3) 0.0242(7) Uani 1 1 d . . . . .
C008 C 0.7029(4) 0.4845(4) 0.6562(3) 0.0200(7) Uani 1 1 d . . . . .
H008 H 0.595366 0.508452 0.587719 0.024 Uiso 1 1 calc R . . . .
C009 C 0.9351(5) 0.4835(5) 0.5218(3) 0.0325(8) Uani 1 1 d . . . . .
H00A H 1.049339 0.526067 0.511679 0.039 Uiso 1 1 calc R . . . .
H00B H 0.865388 0.405161 0.463538 0.039 Uiso 1 1 calc R . . . .
C00A C 0.5576(5) 0.2488(4) 0.7639(3) 0.0232(7) Uani 1 1 d . . . . .
C00B C 0.5870(5) 0.1876(4) 0.8778(3) 0.0277(7) Uani 1 1 d . . . . .
C00C C 0.5637(5) 0.7623(4) 0.7246(3) 0.0259(7) Uani 1 1 d . . . . .
H00C H 0.439117 0.713611 0.714268 0.031 Uiso 1 1 calc R . . . .
H00D H 0.582093 0.851830 0.790299 0.031 Uiso 1 1 calc R . . . .
C00D C 0.6986(4) 0.2894(4) 0.6941(3) 0.0205(7) Uani 1 1 d . . . . .
H00E H 0.821265 0.256161 0.744561 0.025 Uiso 1 1 calc R . . . .
C00E C 0.3576(5) 0.2740(5) 0.7085(4) 0.0352(9) Uani 1 1 d . . . . .
H00F H 0.320453 0.208439 0.630918 0.042 Uiso 1 1 calc R . . . .
H00G H 0.328212 0.400745 0.693340 0.042 Uiso 1 1 calc R . . . .
C00F C 0.7660(6) 0.1517(6) 0.9641(3) 0.0453(11) Uani 1 1 d . . . . .
H00H H 0.775928 0.025184 0.983360 0.068 Uiso 1 1 calc GR . . . .
H00I H 0.773822 0.219606 1.038954 0.068 Uiso 1 1 calc GR . . . .
H00J H 0.865561 0.186633 0.926355 0.068 Uiso 1 1 calc GR . . . .
C00G C 0.4116(6) 0.1596(5) 0.9168(4) 0.0405(9) Uani 1 1 d . . . . .
H00K H 0.402950 0.240686 0.984058 0.049 Uiso 1 1 calc R . . . .
H00L H 0.402030 0.036235 0.943927 0.049 Uiso 1 1 calc R . . . .
C00H C 0.2634(6) 0.1997(7) 0.8037(4) 0.0498(11) Uani 1 1 d . . . . .
H00M H 0.176117 0.287103 0.822730 0.060 Uiso 1 1 calc R . . . .
H00N H 0.195718 0.090534 0.773116 0.060 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
O001 C00C 1.434(4) . ?
O002 C00D 1.447(4) . ?
O003 C005 1.451(4) . ?
O003 C006 1.347(4) . ?
O004 C006 1.203(4) . ?
C005 C008 1.544(4) . ?
C005 C00C 1.504(5) . ?
C006 C007 1.487(5) . ?
C007 C008 1.498(5) . ?
C007 C009 1.321(5) . ?
C008 C00D 1.539(4) . ?
C00A C00B 1.336(4) . ?
C00A C00D 1.493(5) . ?
C00A C00E 1.506(5) . ?
C00B C00F 1.497(5) . ?
C00B C00G 1.501(5) . ?
C00E C00H 1.525(5) . ?
C00G C00H 1.522(6) . ?

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 O003 C005 111.5(2) . . ?
O003 C005 C008 106.3(2) . . ?
O003 C005 C00C 109.0(3) . . ?
C00C C005 C008 113.3(2) . . ?
O003 C006 C007 109.5(3) . . ?
O004 C006 O003 121.5(3) . . ?
O004 C006 C007 129.0(3) . . ?
C006 C007 C008 107.6(3) . . ?
C009 C007 C006 121.4(3) . . ?
C009 C007 C008 131.0(3) . . ?
C007 C008 C005 103.0(3) . . ?
C007 C008 C00D 113.1(2) . . ?
C00D C008 C005 113.7(2) . . ?
C00B C00A C00D 126.8(3) . . ?
C00B C00A C00E 111.9(3) . . ?
C00D C00A C00E 121.3(3) . . ?
C00A C00B C00F 127.9(3) . . ?
C00A C00B C00G 111.7(3) . . ?
C00F C00B C00G 120.4(3) . . ?
O001 C00C C005 111.1(3) . . ?
O002 C00D C008 104.9(2) . . ?
O002 C00D C00A 111.1(2) . . ?
C00A C00D C008 114.0(3) . . ?
C00A C00E C00H 104.1(3) . . ?
C00B C00G C00H 104.6(3) . . ?
C00G C00H C00E 107.1(3) . . ?

_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 1.483
_oxdiff_exptl_absorpt_empirical_full_min 0.647
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_raf_rsr_naph_t_autored
_database_code_depnum_ccdc_archive 'CCDC 2270886'
loop_
_audit_author_name
_audit_author_address
'Ravikant Ranjan'
;Indian Institute of technology Bombay
India
;
_audit_update_record             
;
2023-06-19 deposited with the CCDC.	2023-12-13 downloaded from the CCDC.
;
_audit_creation_date             2023-06-19
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 O4'
_chemical_formula_sum            'C17 H16 O4'
_chemical_formula_weight         284.30
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHO
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                   5.1299(4)
_cell_length_b                   14.7848(10)
_cell_length_c                   9.1241(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.366(7)
_cell_angle_gamma                90
_cell_volume                     692.00(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3112
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      26.5440
_cell_measurement_theta_min      2.6220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7550
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         2.623
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ    107.79 251.79   0.50    3.00  15.81  -9.84 -59.25    --   288
  2  ω   -100.81  15.69   0.50    3.00    --   -9.84 -59.25  20.08  233
  3  φ    181.44 325.44   0.50    3.00  81.02  -9.84  31.50    --   288
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0482386000
_diffrn_orient_matrix_UB_12      -0.0447820000
_diffrn_orient_matrix_UB_13      0.0060640000
_diffrn_orient_matrix_UB_21      0.1120012000
_diffrn_orient_matrix_UB_22      -0.0164701000
_diffrn_orient_matrix_UB_23      -0.0364649000
_diffrn_orient_matrix_UB_31      0.0651407000
_diffrn_orient_matrix_UB_32      -0.0048311000
_diffrn_orient_matrix_UB_33      0.0684301000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.887
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.960
_reflns_number_gt                2159
_reflns_number_total             2381
_reflns_odcompleteness_completeness 84.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.70
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.214
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 828 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_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     192
_refine_ls_number_reflns         2381
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0436
_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)+(0.0502P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1073
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005), C009(H009), C00B(H00C)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C00E(H00F), C00F(H00G), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L)
2.d X=CH2 refined with riding coordinates:
 C00D(H00D,H00E)
2.e Idealised tetrahedral OH refined as rotating group:
 O001(H001), O003(H003)
;
_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
O001 O 0.2484(5) 0.68960(17) 0.8936(3) 0.0312(6) Uani 1 1 d . . . . .
H001 H 0.213850 0.733873 0.947783 0.047 Uiso 1 1 calc GR . . . .
O002 O 0.7514(5) 0.39671(17) 0.6846(2) 0.0294(6) Uani 1 1 d . . . . .
O003 O 0.8590(5) 0.56455(18) 0.8640(3) 0.0355(7) Uani 1 1 d . . . . .
H003 H 0.955135 0.609092 0.882938 0.053 Uiso 1 1 calc GR . . . .
O004 O 0.8028(6) 0.31533(17) 0.8873(3) 0.0357(7) Uani 1 1 d . . . . .
C005 C 0.6073(7) 0.5958(2) 0.8191(4) 0.0260(8) Uani 1 1 d . . . . .
H005 H 0.627765 0.638398 0.734815 0.031 Uiso 1 1 calc R . . . .
C006 C 0.3909(7) 0.4336(2) 0.5191(4) 0.0266(8) Uani 1 1 d . . . . .
C007 C 0.3451(7) 0.3432(3) 0.5026(4) 0.0318(9) Uani 1 1 d . . . . .
H007 H 0.444621 0.301031 0.558044 0.038 Uiso 1 1 calc R . . . .
C008 C 0.6904(7) 0.3762(2) 0.8235(4) 0.0272(8) Uani 1 1 d . . . . .
C009 C 0.4578(7) 0.5121(2) 0.7670(4) 0.0237(8) Uani 1 1 d . . . . .
H009 H 0.271027 0.527333 0.746858 0.028 Uiso 1 1 calc R . . . .
C00A C 0.4806(7) 0.6460(2) 0.9457(4) 0.0282(8) Uani 1 1 d . . . . .
H00A H 0.436854 0.602889 1.024872 0.034 Uiso 1 1 calc R . . . .
H00B H 0.602934 0.691581 0.985908 0.034 Uiso 1 1 calc R . . . .
C00B C 0.5863(7) 0.4699(2) 0.6294(4) 0.0237(8) Uani 1 1 d . . . . .
H00C H 0.697995 0.516353 0.580888 0.028 Uiso 1 1 calc R . . . .
C00C C 0.0420(8) 0.4644(3) 0.3378(4) 0.0301(9) Uani 1 1 d . . . . .
C00D C 0.3343(8) 0.4172(3) 0.9907(4) 0.0343(9) Uani 1 1 d . . . . .
H00D H 0.366030 0.363461 1.045033 0.041 Uiso 1 1 calc R . . . .
H00E H 0.199788 0.457415 1.019755 0.041 Uiso 1 1 calc R . . . .
C00E C 0.1300(8) 0.6508(3) 0.3620(4) 0.0344(9) Uani 1 1 d . . . . .
H00F H 0.160051 0.714089 0.368934 0.041 Uiso 1 1 calc R . . . .
C00F C 0.2785(7) 0.5919(2) 0.4440(4) 0.0306(9) Uani 1 1 d . . . . .
H00G H 0.409361 0.615202 0.507791 0.037 Uiso 1 1 calc R . . . .
C00G C 0.2402(7) 0.4973(2) 0.4354(3) 0.0261(8) Uani 1 1 d . . . . .
C00H C 0.4780(7) 0.4361(2) 0.8743(4) 0.0264(8) Uani 1 1 d . . . . .
C00I C -0.1082(8) 0.5275(3) 0.2563(4) 0.0375(10) Uani 1 1 d . . . . .
H00I H -0.241146 0.505952 0.192332 0.045 Uiso 1 1 calc R . . . .
C00J C 0.1506(8) 0.3112(3) 0.4036(4) 0.0351(9) Uani 1 1 d . . . . .
H00J H 0.124624 0.247959 0.392327 0.042 Uiso 1 1 calc R . . . .
C00K C -0.0669(8) 0.6177(3) 0.2674(4) 0.0415(11) Uani 1 1 d . . . . .
H00K H -0.170326 0.658572 0.211700 0.050 Uiso 1 1 calc R . . . .
C00L C 0.0022(8) 0.3697(3) 0.3255(4) 0.0358(9) Uani 1 1 d . . . . .
H00L H -0.129869 0.347173 0.261772 0.043 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
O001 C00A 1.433(4) . ?
O002 C008 1.341(4) . ?
O002 C00B 1.462(4) . ?
O003 C005 1.429(4) . ?
O004 C008 1.216(4) . ?
C005 C009 1.531(5) . ?
C005 C00A 1.522(5) . ?
C006 C007 1.365(5) . ?
C006 C00B 1.514(5) . ?
C006 C00G 1.435(5) . ?
C007 C00J 1.422(5) . ?
C008 C00H 1.481(5) . ?
C009 C00B 1.553(5) . ?
C009 C00H 1.493(5) . ?
C00C C00G 1.432(5) . ?
C00C C00I 1.417(6) . ?
C00C C00L 1.420(6) . ?
C00D C00H 1.326(5) . ?
C00E C00F 1.376(5) . ?
C00E C00K 1.412(6) . ?
C00F C00G 1.415(5) . ?
C00I C00K 1.353(6) . ?
C00J C00L 1.352(6) . ?

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
C008 O002 C00B 110.8(3) . . ?
O003 C005 C009 106.1(3) . . ?
O003 C005 C00A 109.3(3) . . ?
C00A C005 C009 114.5(3) . . ?
C007 C006 C00B 122.2(3) . . ?
C007 C006 C00G 119.5(3) . . ?
C00G C006 C00B 118.2(3) . . ?
C006 C007 C00J 121.0(4) . . ?
O002 C008 C00H 109.7(3) . . ?
O004 C008 O002 120.5(3) . . ?
O004 C008 C00H 129.8(3) . . ?
C005 C009 C00B 111.2(3) . . ?
C00H C009 C005 111.9(3) . . ?
C00H C009 C00B 101.5(3) . . ?
O001 C00A C005 109.0(3) . . ?
O002 C00B C006 110.3(3) . . ?
O002 C00B C009 105.5(2) . . ?
C006 C00B C009 113.4(3) . . ?
C00I C00C C00G 119.0(4) . . ?
C00I C00C C00L 122.0(4) . . ?
C00L C00C C00G 119.0(4) . . ?
C00F C00E C00K 120.3(4) . . ?
C00E C00F C00G 121.3(3) . . ?
C00C C00G C006 119.1(3) . . ?
C00F C00G C006 123.0(3) . . ?
C00F C00G C00C 117.9(3) . . ?
C008 C00H C009 107.0(3) . . ?
C00D C00H C008 122.6(3) . . ?
C00D C00H C009 130.3(3) . . ?
C00K C00I C00C 121.6(4) . . ?
C00L C00J C007 120.8(4) . . ?
C00I C00K C00E 119.9(4) . . ?
C00J C00L C00C 120.6(4) . . ?

_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 2.433
_oxdiff_exptl_absorpt_empirical_full_min 0.581
####################################################################### 
# 
# 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_raf_rsr_s_autored
_database_code_depnum_ccdc_archive 'CCDC 2267170'
loop_
_audit_author_name
_audit_author_address
'Ravikant Ranjan'
;Indian Institute of technology Bombay
India
;
_audit_update_record             
;
2023-06-02 deposited with the CCDC.	2023-12-13 downloaded from the CCDC.
;
_audit_creation_date             2023-06-02
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 O4 S'
_chemical_formula_sum            'C11 H12 O4 S'
_chemical_formula_weight         240.27
_chemical_absolute_configuration unk
_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'
S S 0.1246 0.1234 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.5447(4)
_cell_length_b                   10.2606(5)
_cell_length_c                   12.5052(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1096.38(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4409
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.2910
_cell_measurement_theta_min      2.8770
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.290
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.096
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0616
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.893
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12004
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.413
_diffrn_reflns_theta_min         2.568
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.893
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  φ   -132.21   3.79   1.00    2.00  16.12 -12.98 -59.25    --   136
  2  φ    173.44 333.44   1.00    2.00  77.88 -12.98  31.50    --   160
  3  ω     -7.63  15.37   1.00    2.00    --  -12.98 -59.25  20.08   23
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0559298000
_diffrn_orient_matrix_UB_12      0.0510606000
_diffrn_orient_matrix_UB_13      0.0003039000
_diffrn_orient_matrix_UB_21      -0.0493466000
_diffrn_orient_matrix_UB_22      0.0371997000
_diffrn_orient_matrix_UB_23      0.0338904000
_diffrn_orient_matrix_UB_31      0.0364047000
_diffrn_orient_matrix_UB_32      -0.0280069000
_diffrn_orient_matrix_UB_33      0.0455173000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.765
_reflns_number_gt                3003
_reflns_number_total             3579
_reflns_odcompleteness_completeness 89.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     33.34
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_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         0.273
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 
;
 Flack x determined using 1030 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0552
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      0.966
_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)+(0.0497P)²+0.1421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0874
_refine_ls_wR_factor_ref         0.0998
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C4(H4A), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C10(H10)
2.d X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_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
S1 S 0.17659(7) 0.70759(6) 0.25301(5) 0.02771(16) Uani 1 1 d . . . . .
O3 O 0.40526(18) 0.29312(16) 0.10778(11) 0.0191(3) Uani 1 1 d . . . . .
H3 H 0.482249 0.258690 0.077010 0.029 Uiso 1 1 calc GR . . . .
O2 O 0.4167(2) 0.26614(15) 0.33423(11) 0.0211(3) Uani 1 1 d . . . . .
O4 O 0.35464(18) 0.66030(15) 0.48514(11) 0.0186(3) Uani 1 1 d . . . . .
H4 H 0.288185 0.684833 0.530359 0.028 Uiso 1 1 calc GR . . . .
O1 O 0.5679(2) 0.19730(17) 0.46863(12) 0.0284(4) Uani 1 1 d . . . . .
C7 C 0.2915(2) 0.5543(2) 0.42360(15) 0.0153(4) Uani 1 1 d . . . . .
H7 H 0.254121 0.485523 0.474178 0.018 Uiso 1 1 calc R . . . .
C3 C 0.5166(3) 0.2870(2) 0.41669(15) 0.0195(4) Uani 1 1 d . . . . .
C8 C 0.1560(3) 0.5965(2) 0.35578(15) 0.0165(4) Uani 1 1 d . . . . .
C4 C 0.4288(3) 0.4982(2) 0.35815(15) 0.0148(4) Uani 1 1 d . . . . .
H4A H 0.482420 0.569211 0.317476 0.018 Uiso 1 1 calc R . . . .
C2 C 0.5441(3) 0.4285(2) 0.42939(16) 0.0168(4) Uani 1 1 d . . . . .
C5 C 0.3768(2) 0.3890(2) 0.28164(15) 0.0161(4) Uani 1 1 d . . . . .
H5 H 0.261015 0.393803 0.270836 0.019 Uiso 1 1 calc R . . . .
C6 C 0.4584(3) 0.3975(2) 0.17456(15) 0.0178(4) Uani 1 1 d . . . . .
H6A H 0.434773 0.482268 0.140306 0.021 Uiso 1 1 calc R . . . .
H6B H 0.573099 0.391314 0.184638 0.021 Uiso 1 1 calc R . . . .
C9 C 0.0043(2) 0.5546(2) 0.36226(17) 0.0201(5) Uani 1 1 d . . . . .
H9 H -0.031352 0.493087 0.413547 0.024 Uiso 1 1 calc R . . . .
C1 C 0.6529(3) 0.4750(2) 0.49500(18) 0.0240(5) Uani 1 1 d . . . . .
H1A H 0.715910 0.416802 0.535487 0.029 Uiso 1 1 calc R . . . .
H1B H 0.667747 0.566413 0.501408 0.029 Uiso 1 1 calc R . . . .
C11 C -0.0173(3) 0.6970(2) 0.21965(17) 0.0249(5) Uani 1 1 d . . . . .
H11 H -0.064872 0.744335 0.163004 0.030 Uiso 1 1 calc R . . . .
C10 C -0.0943(3) 0.6127(3) 0.28426(18) 0.0263(5) Uani 1 1 d . . . . .
H10 H -0.202862 0.594394 0.278046 0.032 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
S1 C8 1.727(2) . ?
S1 C11 1.712(2) . ?
O3 C6 1.432(3) . ?
O2 C3 1.355(3) . ?
O2 C5 1.462(2) . ?
O4 C7 1.438(2) . ?
O1 C3 1.209(3) . ?
C7 C8 1.499(3) . ?
C7 C4 1.542(3) . ?
C3 C2 1.479(3) . ?
C8 C9 1.368(3) . ?
C4 C2 1.508(3) . ?
C4 C5 1.539(3) . ?
C2 C1 1.329(3) . ?
C5 C6 1.512(3) . ?
C9 C10 1.420(3) . ?
C11 C10 1.354(3) . ?

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
C11 S1 C8 92.35(11) . . ?
C3 O2 C5 110.66(16) . . ?
O4 C7 C8 111.97(17) . . ?
O4 C7 C4 106.33(16) . . ?
C8 C7 C4 113.28(16) . . ?
O2 C3 C2 109.66(18) . . ?
O1 C3 O2 121.1(2) . . ?
O1 C3 C2 129.2(2) . . ?
C7 C8 S1 122.21(16) . . ?
C9 C8 S1 110.38(16) . . ?
C9 C8 C7 127.40(19) . . ?
C2 C4 C7 111.12(16) . . ?
C2 C4 C5 102.15(17) . . ?
C5 C4 C7 112.49(17) . . ?
C3 C2 C4 107.35(18) . . ?
C1 C2 C3 122.0(2) . . ?
C1 C2 C4 130.7(2) . . ?
O2 C5 C4 106.31(15) . . ?
O2 C5 C6 109.92(17) . . ?
C6 C5 C4 112.06(17) . . ?
O3 C6 C5 109.07(17) . . ?
C8 C9 C10 112.9(2) . . ?
C10 C11 S1 111.41(17) . . ?
C11 C10 C9 113.0(2) . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.317
_oxdiff_exptl_absorpt_empirical_full_min 0.624
