# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_Id1176r_a
_audit_block_doi                 10.5517/ccdc.csd.cc2bk3np
_database_code_depnum_ccdc_archive 'CCDC 2161402'
loop_
_audit_author_name
_audit_author_address
'Srinivasan Karuppannan'
;Bharathiar University
India
;
_audit_update_record             
;
2022-03-23 deposited with the CCDC.	2024-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        ?
_chemical_name_common            'ETHYL MALTOL'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 O3'
_chemical_formula_sum            'C7 H8 O3'
_chemical_formula_weight         140.13

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   20.9615(11)
_cell_length_b                   20.9615(11)
_cell_length_c                   7.8858(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3000.7(4)
_cell_formula_units_Z            18
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9651
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      27.30

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             1332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9680
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III  Photon Cmos Detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57071
_diffrn_reflns_av_unetI/netI     0.0056
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.816
_diffrn_reflns_theta_max         27.334
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1496
_reflns_number_gt                1389
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+1.9829P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0174(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1496
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0911
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O3 O 0.54633(4) 0.68699(4) 0.39718(12) 0.0470(3) Uani 1 1 d . . . . .
H3 H 0.573416 0.669893 0.380084 0.070 Uiso 1 1 calc R U . . .
O1 O 0.59834(5) 0.87239(4) 0.51082(11) 0.0453(2) Uani 1 1 d . . . . .
O2 O 0.67413(4) 0.73064(4) 0.58150(12) 0.0479(3) Uani 1 1 d . . . . .
C2 C 0.58598(5) 0.75526(5) 0.46398(13) 0.0323(2) Uani 1 1 d . . . . .
C1 C 0.65185(5) 0.77502(5) 0.56092(13) 0.0334(2) Uani 1 1 d . . . . .
C3 C 0.56209(6) 0.80376(6) 0.44108(13) 0.0352(3) Uani 1 1 d . . . . .
C5 C 0.68730(6) 0.84860(6) 0.62813(14) 0.0395(3) Uani 1 1 d . . . . .
H5 H 0.730385 0.865718 0.690859 0.047 Uiso 1 1 calc R U . . .
C6 C 0.49551(7) 0.79072(7) 0.34614(16) 0.0454(3) Uani 1 1 d . . . . .
H6A H 0.477134 0.745745 0.280633 0.054 Uiso 1 1 calc R U . . .
H6B H 0.508850 0.831006 0.267384 0.054 Uiso 1 1 calc R U . . .
C4 C 0.65956(7) 0.89260(6) 0.60217(16) 0.0450(3) Uani 1 1 d . . . . .
H4 H 0.683672 0.939525 0.649460 0.054 Uiso 1 1 calc R U . . .
C7 C 0.43492(8) 0.78433(9) 0.4622(2) 0.0607(4) Uani 1 1 d . . . . .
H7A H 0.418403 0.741825 0.533567 0.091 Uiso 1 1 calc R U . . .
H7B H 0.394460 0.779409 0.395253 0.091 Uiso 1 1 calc R U . . .
H7C H 0.453548 0.827707 0.531390 0.091 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.0353(4) 0.0359(4) 0.0718(6) -0.0161(4) -0.0119(4) 0.0193(3)
O1 0.0525(5) 0.0348(4) 0.0544(5) -0.0040(3) -0.0062(4) 0.0261(4)
O2 0.0379(4) 0.0400(5) 0.0704(6) -0.0001(4) -0.0079(4) 0.0228(4)
C2 0.0287(5) 0.0304(5) 0.0367(5) 0.0000(4) 0.0026(4) 0.0138(4)
C1 0.0285(5) 0.0329(5) 0.0377(5) 0.0040(4) 0.0040(4) 0.0145(4)
C3 0.0371(5) 0.0350(5) 0.0357(5) 0.0006(4) 0.0012(4) 0.0196(4)
C5 0.0339(5) 0.0363(5) 0.0416(6) -0.0021(4) -0.0029(4) 0.0125(4)
C6 0.0478(7) 0.0504(7) 0.0469(6) 0.0004(5) -0.0065(5) 0.0312(6)
C4 0.0457(6) 0.0329(5) 0.0504(7) -0.0068(5) -0.0041(5) 0.0151(5)
C7 0.0476(7) 0.0699(9) 0.0747(9) 0.0146(7) 0.0054(6) 0.0369(7)

_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
O3 C2 1.3515(12) . ?
O3 H3 0.8200 . ?
O1 C4 1.3423(15) . ?
O1 C3 1.3624(13) . ?
O2 C1 1.2427(13) . ?
C2 C3 1.3512(14) . ?
C2 C1 1.4459(14) . ?
C1 C5 1.4373(14) . ?
C3 C6 1.4837(15) . ?
C5 C4 1.3293(17) . ?
C5 H5 0.9300 . ?
C6 C7 1.5162(19) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C4 H4 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
C2 O3 H3 109.5 . . ?
C4 O1 C3 119.36(9) . . ?
C3 C2 O3 118.78(9) . . ?
C3 C2 C1 121.01(9) . . ?
O3 C2 C1 120.19(9) . . ?
O2 C1 C5 124.68(10) . . ?
O2 C1 C2 121.14(9) . . ?
C5 C1 C2 114.18(9) . . ?
C2 C3 O1 121.31(10) . . ?
C2 C3 C6 126.67(10) . . ?
O1 C3 C6 112.01(9) . . ?
C4 C5 C1 121.13(10) . . ?
C4 C5 H5 119.4 . . ?
C1 C5 H5 119.4 . . ?
C3 C6 C7 112.38(11) . . ?
C3 C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C3 C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C5 C4 O1 122.99(10) . . ?
C5 C4 H4 118.5 . . ?
O1 C4 H4 118.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
C3 C2 C1 O2 -179.66(10) . . . . ?
O3 C2 C1 O2 1.62(15) . . . . ?
C3 C2 C1 C5 0.33(14) . . . . ?
O3 C2 C1 C5 -178.38(9) . . . . ?
O3 C2 C3 O1 177.55(9) . . . . ?
C1 C2 C3 O1 -1.18(15) . . . . ?
O3 C2 C3 C6 -0.78(17) . . . . ?
C1 C2 C3 C6 -179.52(10) . . . . ?
C4 O1 C3 C2 0.91(16) . . . . ?
C4 O1 C3 C6 179.47(10) . . . . ?
O2 C1 C5 C4 -179.22(11) . . . . ?
C2 C1 C5 C4 0.78(15) . . . . ?
C2 C3 C6 C7 108.44(14) . . . . ?
O1 C3 C6 C7 -70.03(13) . . . . ?
C1 C5 C4 O1 -1.11(18) . . . . ?
C3 O1 C4 C5 0.25(17) . . . . ?

_refine_diff_density_max         0.246
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.030

_shelx_res_file                  
;
TITL Id1176r_a.res in R-3
    Id1176r_a.res
    created by SHELXL-2016/6 at 11:51:40 on 02-Feb-2022
CELL  0.71073  20.9615  20.9615   7.8858   90.000   90.000  120.000
ZERR   18.000   0.0011   0.0011   0.0005    0.000    0.000    0.000
LATT 3
SYMM -Y, X-Y, Z
SYMM -X+Y, -X, Z
SFAC C  H  O
UNIT 126  144  54
REM Old TITL Id1176r in R-3
REM SHELXT solution in R-3
REM R1 0.154,  Rweak 0.007,  Alpha 0.022,  Orientation as input
REM Formula found by SHELXT:  C7 O3
L.S. 10
BOND $H
FMAP 2
PLAN 20
SIZE 0.20 0.30 0.30
TEMP 23.000
HTAB
CONF
ACTA
WGHT    0.042600    1.982900
EXTI    0.017361
FVAR       0.46644
O3    3    0.546335    0.686995    0.397178    11.00000    0.03530    0.03593 =
         0.07175   -0.01611   -0.01186    0.01930
AFIX 147
H3    2    0.573416    0.669893    0.380084    11.00000   -1.50000
AFIX   0
O1    3    0.598341    0.872387    0.510819    11.00000    0.05247    0.03479 =
         0.05439   -0.00399   -0.00618    0.02614
O2    3    0.674132    0.730640    0.581498    11.00000    0.03786    0.03997 =
         0.07040   -0.00013   -0.00792    0.02282
C2    1    0.585982    0.755262    0.463978    11.00000    0.02865    0.03037 =
         0.03673    0.00003    0.00260    0.01378
C1    1    0.651853    0.775019    0.560924    11.00000    0.02851    0.03292 =
         0.03767    0.00404    0.00401    0.01454
C3    1    0.562091    0.803756    0.441081    11.00000    0.03714    0.03501 =
         0.03567    0.00056    0.00119    0.01963
C5    1    0.687303    0.848599    0.628135    11.00000    0.03385    0.03629 =
         0.04159   -0.00205   -0.00293    0.01249
AFIX  43
H5    2    0.730385    0.865718    0.690859    11.00000   -1.20000
AFIX   0
C6    1    0.495513    0.790721    0.346144    11.00000    0.04776    0.05036 =
         0.04691    0.00042   -0.00648    0.03115
AFIX  23
H6A   2    0.477134    0.745745    0.280633    11.00000   -1.20000
H6B   2    0.508850    0.831006    0.267384    11.00000   -1.20000
AFIX   0
C4    1    0.659562    0.892599    0.602173    11.00000    0.04568    0.03286 =
         0.05039   -0.00675   -0.00411    0.01510
AFIX  43
H4    2    0.683672    0.939525    0.649460    11.00000   -1.20000
AFIX   0
C7    1    0.434924    0.784329    0.462235    11.00000    0.04759    0.06990 =
         0.07466    0.01461    0.00539    0.03691
AFIX 137
H7A   2    0.418403    0.741825    0.533567    11.00000   -1.50000
H7B   2    0.394460    0.779409    0.395253    11.00000   -1.50000
H7C   2    0.453548    0.827707    0.531390    11.00000   -1.50000
AFIX   0
HKLF 4




REM  Id1176r_a.res in R-3
REM R1 =  0.0328 for    1389 Fo > 4sig(Fo)  and  0.0349 for all    1496 data
REM     94 parameters refined using      0 restraints

END

WGHT      0.0426      1.9829

REM Instructions for potential hydrogen bonds
EQIV $1 -y+4/3, x-y+2/3, z-1/3
HTAB O3 O2_$1

REM Highest difference peak  0.246,  deepest hole -0.183,  1-sigma level  0.030
Q1    1   0.6223  0.7666  0.5028  11.00000  0.05    0.25
Q2    1   0.5636  0.7742  0.4909  11.00000  0.05    0.22
Q3    1   0.5864  0.7851  0.4219  11.00000  0.05    0.20
Q4    1   0.6626  0.8084  0.6123  11.00000  0.05    0.19
Q5    1   0.5268  0.7946  0.3992  11.00000  0.05    0.18
Q6    1   0.6535  0.8562  0.6662  11.00000  0.05    0.15
Q7    1   0.6859  0.8764  0.5585  11.00000  0.05    0.13
Q8    1   0.6615  0.9460  0.6279  11.00000  0.05    0.12
Q9    1   0.5751  0.7325  0.4226  11.00000  0.05    0.11
Q10   1   0.4693  0.7856  0.4072  11.00000  0.05    0.10
Q11   1   0.7175  0.7486  0.6352  11.00000  0.05    0.10
Q12   1   0.6835  0.7578  0.5263  11.00000  0.05    0.09
Q13   1   0.6210  0.8727  0.5733  11.00000  0.05    0.09
Q14   1   0.6655  0.7385  0.6730  11.00000  0.05    0.09
Q15   1   0.5741  0.8315  0.4955  11.00000  0.05    0.08
Q16   1   0.4992  0.7764  0.2367  11.00000  0.05    0.08
Q17   1   0.4065  0.8051  0.4337  11.00000  0.05    0.08
Q18   1   0.4318  0.7658  0.5914  11.00000  0.05    0.08
Q19   1   0.4076  0.7205  0.4694  11.00000  0.05    0.07
Q20   1   0.6405  0.6859  0.5360  11.00000  0.05    0.07
;
_shelx_res_checksum              863

_exptl_crystal_recrystallization_method 'Solution Growth Method'
####################################################################### 
# 
# 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_T11_a
_database_code_depnum_ccdc_archive 'CCDC 2260298'
loop_
_audit_author_name
_audit_author_address
'Srinivasan Karuppannan'
;Bharathiar University
India
;
_audit_update_record             
;
2023-05-03 deposited with the CCDC.	2024-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        '2ETHYL 3HYDROXY4PYRANONE'
_chemical_name_common            'ETHYL MALTOL'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 O3'
_chemical_formula_sum            'C7 H8 O3'
_chemical_formula_weight         140.13

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   4.8597(7)
_cell_length_b                   6.8797(10)
_cell_length_c                   20.170(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.200(4)
_cell_angle_gamma                90
_cell_volume                     671.56(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4046
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      20.75

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.030
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.002
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.997
_shelx_estimated_absorpt_T_max   1.000
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.109
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'BRUKER APEX -III PHOTON CMOS DETECTOR'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12501
_diffrn_reflns_av_unetI/netI     0.1020
_diffrn_reflns_av_R_equivalents  0.1455
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.130
_diffrn_reflns_theta_max         27.193
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1498
_reflns_number_gt                741
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'BRUKER APEX III'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRIKER SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0485P)²+0.1730P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.014(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1498
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1785
_refine_ls_R_factor_gt           0.0746
_refine_ls_wR_factor_ref         0.1414
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.8659(4) 0.5143(3) 0.60844(10) 0.0462(6) Uani 1 1 d . . . . .
O2 O 0.3071(4) 0.4387(3) 0.74249(11) 0.0484(6) Uani 1 1 d . . . . .
O3 O 0.4224(5) 0.1370(3) 0.65887(10) 0.0504(7) Uani 1 1 d . . . . .
H3 H 0.350607 0.125530 0.693926 0.076 Uiso 1 1 calc R U . . .
C4 C 0.5477(6) 0.3127(4) 0.65726(13) 0.0340(7) Uani 1 1 d . . . . .
C3 C 0.4762(6) 0.4662(4) 0.70131(14) 0.0342(7) Uani 1 1 d . . . . .
C5 C 0.7323(6) 0.3398(4) 0.61284(14) 0.0367(8) Uani 1 1 d . . . . .
C2 C 0.6187(6) 0.6453(4) 0.69321(14) 0.0400(8) Uani 1 1 d . . . . .
H2 H 0.580899 0.752471 0.718992 0.048 Uiso 1 1 calc R U . . .
C1 C 0.8048(7) 0.6595(4) 0.64908(15) 0.0480(9) Uani 1 1 d . . . . .
H1 H 0.898051 0.776837 0.646177 0.058 Uiso 1 1 calc R U . . .
C6 C 0.8127(7) 0.1991(4) 0.56224(14) 0.0497(9) Uani 1 1 d . . . . .
H6A H 0.756563 0.069690 0.574589 0.060 Uiso 1 1 calc R U . . .
H6B H 1.012321 0.199138 0.562297 0.060 Uiso 1 1 calc R U . . .
C7 C 0.6860(8) 0.2437(5) 0.49273(15) 0.0649(11) Uani 1 1 d . . . . .
H7A H 0.488311 0.239214 0.491862 0.097 Uiso 1 1 calc R U . . .
H7B H 0.747028 0.149157 0.462246 0.097 Uiso 1 1 calc R U . . .
H7C H 0.742322 0.370973 0.479904 0.097 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0511(13) 0.0457(13) 0.0431(13) 0.0000(11) 0.0118(10) -0.0042(11)
O2 0.0569(14) 0.0407(12) 0.0507(14) -0.0002(11) 0.0219(11) 0.0009(11)
O3 0.0708(16) 0.0350(12) 0.0480(15) -0.0042(11) 0.0192(12) -0.0083(12)
C4 0.0404(18) 0.0306(17) 0.0311(17) 0.0016(13) 0.0034(15) 0.0022(14)
C3 0.0362(18) 0.0349(17) 0.0308(17) 0.0078(14) -0.0016(15) 0.0051(15)
C5 0.0434(19) 0.0336(17) 0.0329(17) 0.0006(15) 0.0028(15) 0.0028(15)
C2 0.049(2) 0.0315(16) 0.0391(19) -0.0042(14) 0.0038(16) 0.0042(15)
C1 0.059(2) 0.0367(18) 0.048(2) -0.0032(17) 0.0019(18) -0.0076(16)
C6 0.052(2) 0.052(2) 0.047(2) -0.0039(16) 0.0131(17) 0.0106(17)
C7 0.092(3) 0.058(2) 0.045(2) -0.0065(18) 0.015(2) 0.002(2)

_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 1.343(3) . ?
O1 C5 1.372(3) . ?
O2 C3 1.235(3) . ?
O3 C4 1.355(3) . ?
O3 H3 0.8200 . ?
C4 C5 1.337(4) . ?
C4 C3 1.442(4) . ?
C3 C2 1.430(4) . ?
C5 C6 1.484(4) . ?
C2 C1 1.329(4) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C6 C7 1.511(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
C1 O1 C5 118.7(2) . . ?
C4 O3 H3 109.5 . . ?
C5 C4 O3 118.1(2) . . ?
C5 C4 C3 121.6(3) . . ?
O3 C4 C3 120.3(2) . . ?
O2 C3 C2 124.5(3) . . ?
O2 C3 C4 121.0(3) . . ?
C2 C3 C4 114.5(3) . . ?
C4 C5 O1 121.0(2) . . ?
C4 C5 C6 127.2(3) . . ?
O1 C5 C6 111.8(2) . . ?
C1 C2 C3 120.4(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C1 O1 123.8(3) . . ?
C2 C1 H1 118.1 . . ?
O1 C1 H1 118.1 . . ?
C5 C6 C7 113.3(2) . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
C5 C4 C3 O2 -179.4(3) . . . . ?
O3 C4 C3 O2 2.3(4) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?
O3 C4 C3 C2 -178.5(3) . . . . ?
O3 C4 C5 O1 179.8(2) . . . . ?
C3 C4 C5 O1 1.4(4) . . . . ?
O3 C4 C5 C6 2.1(4) . . . . ?
C3 C4 C5 C6 -176.2(3) . . . . ?
C1 O1 C5 C4 -1.0(4) . . . . ?
C1 O1 C5 C6 177.0(2) . . . . ?
O2 C3 C2 C1 177.6(3) . . . . ?
C4 C3 C2 C1 -1.6(4) . . . . ?
C3 C2 C1 O1 2.1(5) . . . . ?
C5 O1 C1 C2 -0.8(4) . . . . ?
C4 C5 C6 C7 103.4(4) . . . . ?
O1 C5 C6 C7 -74.4(3) . . . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.045

_shelx_res_file                  
;
TITL T11_a.res in P2(1)/n
    T11_a.res
    created by SHELXL-2016/6 at 18:46:00 on 26-Apr-2023
CELL  0.71073   4.8597   6.8797  20.1697   90.000   95.200   90.000
ZERR    4.000   0.0007   0.0010   0.0031    0.000    0.004    0.000
LATT 1
SYMM 1/2-X, 1/2+Y, 1/2-Z
SFAC C  H  O
UNIT 28  32  12
REM Old TITL T11 in P2(1)/n
REM SHELXT solution in P2(1)/n
REM R1 0.212,  Rweak 0.090,  Alpha 0.066,  Orientation as input
REM Formula found by SHELXT:  C7 O3
L.S. 10
ACTA
BOND $H
FMAP 2
PLAN 20
SIZE 0.002 0.01 0.03
TEMP 23.000
HTAB
CONF
WGHT    0.048500    0.173000
EXTI    0.014302
FVAR       0.87192
O1    3    0.865902    0.514300    0.608437    11.00000    0.05111    0.04572 =
         0.04310    0.00005    0.01181   -0.00417
O2    3    0.307100    0.438743    0.742489    11.00000    0.05693    0.04069 =
         0.05075   -0.00024    0.02190    0.00089
O3    3    0.422393    0.136951    0.658875    11.00000    0.07084    0.03500 =
         0.04802   -0.00417    0.01916   -0.00828
AFIX 147
H3    2    0.350607    0.125530    0.693926    11.00000   -1.50000
AFIX   0
C4    1    0.547722    0.312690    0.657263    11.00000    0.04035    0.03061 =
         0.03113    0.00163    0.00343    0.00220
C3    1    0.476220    0.466171    0.701307    11.00000    0.03619    0.03491 =
         0.03078    0.00776   -0.00165    0.00513
C5    1    0.732333    0.339780    0.612840    11.00000    0.04344    0.03358 =
         0.03294    0.00059    0.00284    0.00284
C2    1    0.618706    0.645312    0.693214    11.00000    0.04929    0.03148 =
         0.03910   -0.00423    0.00380    0.00423
AFIX  43
H2    2    0.580899    0.752471    0.718992    11.00000   -1.20000
AFIX   0
C1    1    0.804784    0.659537    0.649081    11.00000    0.05910    0.03669 =
         0.04759   -0.00320    0.00191   -0.00762
AFIX  43
H1    2    0.898051    0.776837    0.646177    11.00000   -1.20000
AFIX   0
C6    1    0.812699    0.199059    0.562241    11.00000    0.05230    0.05164 =
         0.04678   -0.00393    0.01313    0.01057
AFIX  23
H6A   2    0.756563    0.069690    0.574589    11.00000   -1.20000
H6B   2    1.012321    0.199138    0.562297    11.00000   -1.20000
AFIX   0
C7    1    0.686047    0.243666    0.492728    11.00000    0.09248    0.05848 =
         0.04550   -0.00652    0.01523    0.00190
AFIX 137
H7A   2    0.488311    0.239214    0.491862    11.00000   -1.50000
H7B   2    0.747028    0.149157    0.462246    11.00000   -1.50000
H7C   2    0.742322    0.370973    0.479904    11.00000   -1.50000
AFIX   0
HKLF 4




REM  T11_a.res in P2(1)/n
REM R1 =  0.0746 for     741 Fo > 4sig(Fo)  and  0.1785 for all    1498 data
REM     94 parameters refined using      0 restraints

END

WGHT      0.0485      0.1738

REM Instructions for potential hydrogen bonds
EQIV $1 -x+1/2, y-1/2, -z+3/2
HTAB O3 O2_$1
EQIV $2 -x+1/2, y+1/2, -z+3/2
HTAB C2 O2_$2

REM Highest difference peak  0.207,  deepest hole -0.189,  1-sigma level  0.045
Q1    1   0.2246  0.5579  0.7607  11.00000  0.05    0.21
Q2    1   0.9315  0.0223  0.5801  11.00000  0.05    0.19
Q3    1   0.1097  0.1392  0.7146  11.00000  0.05    0.16
Q4    1   0.2630 -0.0284  0.7047  11.00000  0.05    0.16
Q5    1   0.7273  0.8491  0.6190  11.00000  0.05    0.15
Q6    1   0.3134  0.3026  0.7557  11.00000  0.05    0.14
Q7    1   0.9223  0.3235  0.5269  11.00000  0.05    0.14
Q8    1   0.4662  0.6193  0.6789  11.00000  0.05    0.13
Q9    1   0.8599  0.6477  0.5823  11.00000  0.05    0.13
Q10   1   0.2537  0.1531  0.6685  11.00000  0.05    0.13
Q11   1   0.6365  0.6602  0.6495  11.00000  0.05    0.13
Q12   1   0.6538  0.1775  0.5387  11.00000  0.05    0.13
Q13   1   0.5626  0.3420  0.6147  11.00000  0.05    0.13
Q14   1   0.9940  0.1029  0.4989  11.00000  0.05    0.13
Q15   1   0.9906  0.8718  0.6222  11.00000  0.05    0.12
Q16   1   0.8055  0.5333  0.7233  11.00000  0.05    0.12
Q17   1   0.5300  0.3458  0.7071  11.00000  0.05    0.12
Q18   1   0.6213  0.9050  0.6709  11.00000  0.05    0.12
Q19   1   0.9688  0.4681  0.5676  11.00000  0.05    0.12
Q20   1   0.9141  0.7633  0.6221  11.00000  0.05    0.12
;
_shelx_res_checksum              55050

_chemical_compound_source        'solution crystallization method'
_chemical_properties_physical    Air-sensitive,Moisture-sensitive,Hygroscopic
####################################################################### 
# 
# 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_ID1211EMA_EWTRI_a
_audit_block_doi                 10.5517/ccdc.csd.cc2bk3vw
_database_code_depnum_ccdc_archive 'CCDC 2161408'
loop_
_audit_author_name
_audit_author_address
'Srinivasan Karuppannan'
;Bharathiar University
India
;
_audit_update_record             
;
2022-03-23 deposited with the CCDC.	2024-02-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        2-ETHYL-3-HYDROXY-4-PYRANONE
_chemical_name_common            'ETHYL MALTOL'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 O3'
_chemical_formula_sum            'C7 H8 O3'
_chemical_formula_weight         140.13

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1414(8)
_cell_length_b                   7.6229(8)
_cell_length_c                   7.6784(8)
_cell_angle_alpha                62.162(3)
_cell_angle_beta                 68.379(3)
_cell_angle_gamma                76.408(3)
_cell_volume                     342.61(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6739
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.01

_exptl_crystal_description       COLUMNAR
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_F_000             148
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.025
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.107
_shelx_estimated_absorpt_T_min   0.997
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9970
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_process_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III PHOTON CMOS DETECTOR'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19576
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.031
_diffrn_reflns_theta_max         27.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1529
_reflns_number_gt                1137
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'BRUKER APEX3'
_computing_cell_refinement       'BRUKER SAINT'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0524P)²+0.0679P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.074(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1529
_refine_ls_number_parameters     94
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1248
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.04608(17) 0.1032(2) 0.66783(17) 0.0636(4) Uani 1 1 d . . . . .
H1 H -0.001916 0.059999 0.793766 0.095 Uiso 1 1 calc R U . . .
O3 O 0.52265(17) 0.30608(18) 0.34480(17) 0.0611(4) Uani 1 1 d . . . . .
O2 O 0.22952(18) 0.0360(2) 0.95314(17) 0.0669(4) Uani 1 1 d . . . . .
C1 C 0.3323(2) 0.2495(2) 0.4085(2) 0.0498(4) Uani 1 1 d . . . . .
C2 C 0.2331(2) 0.1591(2) 0.6107(2) 0.0462(4) Uani 1 1 d . . . . .
C3 C 0.3227(2) 0.1186(2) 0.7675(2) 0.0469(4) Uani 1 1 d . . . . .
C4 C 0.5233(2) 0.1792(2) 0.6890(3) 0.0537(4) Uani 1 1 d . . . . .
H4 H 0.592355 0.156713 0.780185 0.064 Uiso 1 1 calc R U . . .
C6 C 0.2521(3) 0.3060(3) 0.2342(3) 0.0610(5) Uani 1 1 d . . . . .
H6A H 0.151559 0.216093 0.276703 0.073 Uiso 1 1 calc R U . . .
H6B H 0.361084 0.292591 0.118720 0.073 Uiso 1 1 calc R U . . .
C5 C 0.6112(3) 0.2672(3) 0.4876(3) 0.0619(5) Uani 1 1 d . . . . .
H5 H 0.741945 0.304366 0.442089 0.074 Uiso 1 1 calc R U . . .
C7 C 0.1583(3) 0.5165(3) 0.1661(3) 0.0801(6) Uani 1 1 d . . . . .
H7A H 0.048554 0.529489 0.279392 0.120 Uiso 1 1 calc R U . . .
H7B H 0.108499 0.548429 0.053628 0.120 Uiso 1 1 calc R U . . .
H7C H 0.258027 0.605978 0.122049 0.120 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0483(7) 0.0986(10) 0.0488(7) -0.0272(7) -0.0153(5) -0.0217(6)
O3 0.0503(7) 0.0777(8) 0.0501(7) -0.0225(6) -0.0100(5) -0.0143(6)
O2 0.0546(7) 0.0954(10) 0.0449(7) -0.0169(6) -0.0178(5) -0.0188(6)
C1 0.0455(8) 0.0566(9) 0.0510(9) -0.0255(7) -0.0155(7) -0.0024(7)
C2 0.0409(8) 0.0533(9) 0.0479(8) -0.0227(7) -0.0154(6) -0.0035(6)
C3 0.0438(8) 0.0505(9) 0.0487(9) -0.0201(7) -0.0185(7) -0.0020(6)
C4 0.0467(9) 0.0621(10) 0.0589(10) -0.0244(8) -0.0243(7) -0.0042(7)
C6 0.0622(11) 0.0774(12) 0.0481(9) -0.0281(8) -0.0173(8) -0.0086(9)
C5 0.0438(9) 0.0782(12) 0.0654(11) -0.0279(9) -0.0165(8) -0.0127(8)
C7 0.0882(14) 0.0794(14) 0.0706(13) -0.0165(10) -0.0409(11) -0.0076(11)

_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 C2 1.3490(18) . ?
O1 H1 0.8200 . ?
O3 C5 1.346(2) . ?
O3 C1 1.3641(19) . ?
O2 C3 1.2374(19) . ?
C1 C2 1.344(2) . ?
C1 C6 1.489(2) . ?
C2 C3 1.442(2) . ?
C3 C4 1.430(2) . ?
C4 C5 1.322(2) . ?
C4 H4 0.9300 . ?
C6 C7 1.506(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C5 H5 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
C2 O1 H1 109.5 . . ?
C5 O3 C1 118.95(13) . . ?
C2 C1 O3 120.71(14) . . ?
C2 C1 C6 126.25(15) . . ?
O3 C1 C6 113.00(14) . . ?
C1 C2 O1 119.01(13) . . ?
C1 C2 C3 121.64(14) . . ?
O1 C2 C3 119.35(13) . . ?
O2 C3 C4 124.49(14) . . ?
O2 C3 C2 121.05(14) . . ?
C4 C3 C2 114.47(14) . . ?
C5 C4 C3 120.40(15) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C1 C6 C7 111.51(15) . . ?
C1 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C1 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108.0 . . ?
C4 C5 O3 123.82(15) . . ?
C4 C5 H5 118.1 . . ?
O3 C5 H5 118.1 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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
C5 O3 C1 C2 1.0(2) . . . . ?
C5 O3 C1 C6 178.75(15) . . . . ?
O3 C1 C2 O1 -179.21(14) . . . . ?
C6 C1 C2 O1 3.4(3) . . . . ?
O3 C1 C2 C3 0.1(2) . . . . ?
C6 C1 C2 C3 -177.36(15) . . . . ?
C1 C2 C3 O2 179.71(16) . . . . ?
O1 C2 C3 O2 -1.0(2) . . . . ?
C1 C2 C3 C4 -1.0(2) . . . . ?
O1 C2 C3 C4 178.29(14) . . . . ?
O2 C3 C4 C5 -179.85(17) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C2 C1 C6 C7 92.9(2) . . . . ?
O3 C1 C6 C7 -84.66(18) . . . . ?
C3 C4 C5 O3 0.2(3) . . . . ?
C1 O3 C5 C4 -1.1(3) . . . . ?

_refine_diff_density_max         0.204
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.036

_shelx_res_file                  
;
TITL ID1211EMA_EWTRI_a.res in P-1
    ID1211EMA_EWTRI_a.res
    created by SHELXL-2016/6 at 11:26:09 on 27-Nov-2021
CELL  0.71073   7.1414   7.6229   7.6784   62.162   68.379   76.408
ZERR    2.000   0.0008   0.0008   0.0008    0.003    0.003    0.003
LATT 1
SFAC C  H  O
UNIT 14  16  6
REM Old TITL ID1211EMA_EWTRI in P-1
REM SHELXT solution in P-1
REM R1 0.174,  Rweak 0.014,  Alpha 0.045,  Orientation as input
REM Formula found by SHELXT:  C7 O3
L.S. 10
ACTA
BOND $H
FMAP 2
PLAN 20
SIZE 0.02 0.025 0.025
TEMP 23.00
HTAB
CONF
WGHT    0.052400    0.067900
EXTI    0.073852
FVAR       1.31661
O1    3    0.046079    0.103213    0.667828    11.00000    0.04833    0.09862 =
         0.04885   -0.02725   -0.01529   -0.02175
AFIX 147
H1    2   -0.001916    0.059999    0.793766    11.00000   -1.50000
AFIX   0
O3    3    0.522650    0.306078    0.344800    11.00000    0.05031    0.07773 =
         0.05010   -0.02246   -0.00998   -0.01427
O2    3    0.229522    0.035957    0.953142    11.00000    0.05465    0.09542 =
         0.04492   -0.01693   -0.01776   -0.01881
C1    1    0.332328    0.249524    0.408549    11.00000    0.04548    0.05660 =
         0.05097   -0.02547   -0.01554   -0.00243
C2    1    0.233134    0.159129    0.610728    11.00000    0.04094    0.05332 =
         0.04785   -0.02267   -0.01542   -0.00351
C3    1    0.322650    0.118579    0.767464    11.00000    0.04381    0.05051 =
         0.04869   -0.02010   -0.01849   -0.00197
C4    1    0.523300    0.179250    0.689025    11.00000    0.04668    0.06212 =
         0.05893   -0.02443   -0.02430   -0.00418
AFIX  43
H4    2    0.592355    0.156713    0.780185    11.00000   -1.20000
AFIX   0
C6    1    0.252068    0.305996    0.234160    11.00000    0.06220    0.07738 =
         0.04815   -0.02810   -0.01732   -0.00861
AFIX  23
H6A   2    0.151559    0.216093    0.276703    11.00000   -1.20000
H6B   2    0.361084    0.292591    0.118720    11.00000   -1.20000
AFIX   0
C5    1    0.611247    0.267208    0.487643    11.00000    0.04378    0.07822 =
         0.06544   -0.02793   -0.01651   -0.01265
AFIX  43
H5    2    0.741945    0.304366    0.442089    11.00000   -1.20000
AFIX   0
C7    1    0.158290    0.516550    0.166145    11.00000    0.08818    0.07944 =
         0.07058   -0.01650   -0.04093   -0.00758
AFIX 137
H7A   2    0.048554    0.529489    0.279392    11.00000   -1.50000
H7B   2    0.108499    0.548429    0.053628    11.00000   -1.50000
H7C   2    0.258027    0.605978    0.122049    11.00000   -1.50000
AFIX   0
HKLF 4




REM  ID1211EMA_EWTRI_a.res in P-1
REM R1 =  0.0468 for    1137 Fo > 4sig(Fo)  and  0.0647 for all    1529 data
REM     94 parameters refined using      0 restraints

END

WGHT      0.0524      0.0679

REM Instructions for potential hydrogen bonds
HTAB O1 O2
EQIV $1 -x, -y, -z+2
HTAB O1 O2_$1
EQIV $2 -x+1, -y, -z+2
HTAB C4 O2_$2

REM Highest difference peak  0.204,  deepest hole -0.140,  1-sigma level  0.036
Q1    1   0.2549  0.2829  0.5046  11.00000  0.05    0.20
Q2    1   0.7674  0.2932  0.3776  11.00000  0.05    0.16
Q3    1   0.2600  0.1698  0.6958  11.00000  0.05    0.15
Q4    1   0.2078  0.4204  0.2609  11.00000  0.05    0.14
Q5    1   0.2700  0.3075  0.3434  11.00000  0.05    0.14
Q6    1   0.2962  0.1096  0.6879  11.00000  0.05    0.13
Q7    1   0.3199  0.1491  0.5237  11.00000  0.05    0.13
Q8    1   0.0248  0.2171  0.6904  11.00000  0.05    0.12
Q9    1   0.2626  0.1281  0.9059  11.00000  0.05    0.12
Q10   1   0.4220  0.1569  0.7325  11.00000  0.05    0.12
Q11   1   0.5195  0.2793  0.5937  11.00000  0.05    0.12
Q12   1   0.2615 -0.0177  1.0393  11.00000  0.05    0.11
Q13   1   0.6571  0.0799  0.8397  11.00000  0.05    0.10
Q14   1   0.5787  0.1521  0.5854  11.00000  0.05    0.10
Q15   1   0.2145  0.4137  0.1200  11.00000  0.05    0.10
Q16   1   0.1347  0.1363  0.9110  11.00000  0.05    0.10
Q17   1   0.6313  0.0821  0.7464  11.00000  0.05    0.10
Q18   1   0.9390  0.3136  0.2730  11.00000  0.05    0.10
Q19   1   0.2659  0.0510  1.0666  11.00000  0.05    0.10
Q20   1   0.5163  0.3520  0.4141  11.00000  0.05    0.10
;
_shelx_res_checksum              79324

_exptl_crystal_recrystallization_method 'Solution Growth Method'
