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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_P21_a
_database_code_depnum_ccdc_archive 'CCDC 1948418'
loop_
_audit_author_name
_audit_author_address
'Srinivasan Karuppannan'
;Bharathiar University
India
;
_audit_update_record             
;
2019-08-21 deposited with the CCDC.	2021-01-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        Vanillin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 O3'
_chemical_formula_weight         152.14

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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+1/2, -z'

_cell_length_a                   14.0276(8)
_cell_length_b                   7.8650(4)
_cell_length_c                   14.9871(8)
_cell_angle_alpha                90
_cell_angle_beta                 115.475(2)
_cell_angle_gamma                90
_cell_volume                     1492.72(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9955
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      26.66

_exptl_crystal_description       PLATE
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43087
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.634
_diffrn_reflns_theta_max         27.193
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6592
_reflns_number_gt                5214
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.857
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.998

_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 APEX2'
_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    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0449P)²+0.3255P] 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       0.025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1963 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6592
_refine_ls_number_parameters     406
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1137
_refine_ls_wR_factor_gt          0.1072
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.105
_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
O3 O 0.18272(16) 0.0873(3) 0.77753(14) 0.0488(6) Uani 1 1 d . . . . .
O9 O 0.79955(16) 0.1421(3) 0.27477(14) 0.0502(6) Uani 1 1 d . . . . .
O2 O 0.05881(16) 0.1027(4) 0.58379(15) 0.0570(6) Uani 1 1 d . . . . .
H2 H 0.049806 0.056231 0.628542 0.085 Uiso 1 1 calc R U . . .
O8 O 0.71468(18) 0.0617(4) 0.08350(16) 0.0607(7) Uani 1 1 d . . . . .
H8 H 0.776506 0.057376 0.124494 0.091 Uiso 1 1 calc R U . . .
O6 O 0.63785(16) 0.6092(3) 0.69675(15) 0.0563(6) Uani 1 1 d . . . . .
O5 O 0.70716(18) 0.5730(4) 0.89226(16) 0.0633(7) Uani 1 1 d . . . . .
H5 H 0.654860 0.532732 0.846819 0.095 Uiso 1 1 calc R U . . .
O12 O 0.26410(18) 0.6527(4) 0.19431(15) 0.0614(7) Uani 1 1 d . . . . .
O4 O 0.95543(19) 0.9139(4) 0.66826(18) 0.0653(7) Uani 1 1 d . . . . .
O1 O 0.52626(19) 0.3898(4) 0.8080(2) 0.0673(7) Uani 1 1 d . . . . .
O10 O -0.08553(19) 0.9405(4) 0.1608(2) 0.0690(7) Uani 1 1 d . . . . .
O7 O 0.4924(2) 0.4724(4) 0.3086(2) 0.0706(8) Uani 1 1 d . . . . .
O11 O 0.3770(2) 0.6351(5) 0.38884(18) 0.0785(9) Uani 1 1 d . . . . .
H11 H 0.388561 0.597901 0.343342 0.118 Uiso 1 1 calc R U . . .
C5 C 0.1565(2) 0.1689(4) 0.6198(2) 0.0409(7) Uani 1 1 d . . . . .
C29 C 0.6584(2) 0.1522(4) 0.1203(2) 0.0436(7) Uani 1 1 d . . . . .
C3 C 0.3224(2) 0.2371(4) 0.7551(2) 0.0406(7) Uani 1 1 d . . . . .
H3 H 0.366799 0.237157 0.822375 0.049 Uiso 1 1 calc R U . . .
C30 C 0.6986(2) 0.1959(4) 0.2205(2) 0.0398(7) Uani 1 1 d . . . . .
C6 C 0.1899(3) 0.2428(5) 0.5548(2) 0.0520(8) Uani 1 1 d . . . . .
H6 H 0.145199 0.245476 0.487571 0.062 Uiso 1 1 calc R U . . .
C31 C 0.6377(2) 0.2853(4) 0.2548(2) 0.0420(7) Uani 1 1 d . . . . .
H31 H 0.664289 0.313776 0.321402 0.050 Uiso 1 1 calc R U . . .
C4 C 0.2244(2) 0.1655(4) 0.7217(2) 0.0374(6) Uani 1 1 d . . . . .
C13 C 0.7685(2) 0.6485(4) 0.8557(2) 0.0455(7) Uani 1 1 d . . . . .
C15 C 0.8015(2) 0.7495(4) 0.7204(2) 0.0432(7) Uani 1 1 d . . . . .
H15 H 0.779791 0.764305 0.652915 0.052 Uiso 1 1 calc R U . . .
C2 C 0.3562(2) 0.3102(4) 0.6886(2) 0.0462(7) Uani 1 1 d . . . . .
C10 C 0.9008(2) 0.8070(4) 0.7872(2) 0.0470(8) Uani 1 1 d . . . . .
C14 C 0.7360(2) 0.6715(4) 0.7539(2) 0.0407(7) Uani 1 1 d . . . . .
C21 C 0.2803(3) 0.7030(5) 0.3525(2) 0.0526(8) Uani 1 1 d . . . . .
C20 C 0.2176(2) 0.7154(4) 0.2495(2) 0.0454(7) Uani 1 1 d . . . . .
C19 C 0.1192(2) 0.7861(4) 0.2150(2) 0.0452(7) Uani 1 1 d . . . . .
H19 H 0.077459 0.794656 0.147349 0.054 Uiso 1 1 calc R U . . .
C8 C 0.2461(3) 0.0842(5) 0.8819(2) 0.0554(9) Uani 1 1 d . . . . .
H8A H 0.313532 0.034539 0.895542 0.083 Uiso 1 1 calc R U . . .
H8B H 0.211432 0.017825 0.912934 0.083 Uiso 1 1 calc R U . . .
H8C H 0.256072 0.198168 0.907202 0.083 Uiso 1 1 calc R U . . .
C26 C 0.5358(2) 0.3338(4) 0.1899(3) 0.0487(8) Uani 1 1 d . . . . .
C27 C 0.4971(2) 0.2938(5) 0.0911(3) 0.0559(9) Uani 1 1 d . . . . .
H27 H 0.429432 0.328186 0.047908 0.067 Uiso 1 1 calc R U . . .
C18 C 0.0810(3) 0.8459(4) 0.2819(3) 0.0470(8) Uani 1 1 d . . . . .
C23 C 0.1429(3) 0.8336(5) 0.3821(3) 0.0599(10) Uani 1 1 d . . . . .
H23 H 0.117365 0.871834 0.426443 0.072 Uiso 1 1 calc R U . . .
C28 C 0.5576(3) 0.2035(5) 0.0556(2) 0.0567(9) Uani 1 1 d . . . . .
H28 H 0.531007 0.177084 -0.011213 0.068 Uiso 1 1 calc R U . . .
C7 C 0.2896(3) 0.3127(5) 0.5895(3) 0.0556(9) Uani 1 1 d . . . . .
H7 H 0.311991 0.361892 0.545293 0.067 Uiso 1 1 calc R U . . .
C1 C 0.4611(3) 0.3862(5) 0.7243(3) 0.0594(9) Uani 1 1 d . . . . .
H1 H 0.478788 0.436515 0.677302 0.071 Uiso 1 1 calc R U . . .
C32 C 0.8466(3) 0.1821(5) 0.3768(2) 0.0556(9) Uani 1 1 d . . . . .
H32A H 0.846092 0.303062 0.385043 0.083 Uiso 1 1 calc R U . . .
H32B H 0.918124 0.141633 0.406282 0.083 Uiso 1 1 calc R U . . .
H32C H 0.807506 0.128615 0.408207 0.083 Uiso 1 1 calc R U . . .
C22 C 0.2419(3) 0.7652(6) 0.4163(3) 0.0649(11) Uani 1 1 d . . . . .
H22 H 0.284018 0.760753 0.484033 0.078 Uiso 1 1 calc R U . . .
C16 C 0.5956(3) 0.6406(6) 0.5930(2) 0.0710(12) Uani 1 1 d . . . . .
H16A H 0.590725 0.760979 0.581324 0.106 Uiso 1 1 calc R U . . .
H16B H 0.526614 0.590768 0.560809 0.106 Uiso 1 1 calc R U . . .
H16C H 0.641115 0.591174 0.567146 0.106 Uiso 1 1 calc R U . . .
C12 C 0.8664(3) 0.7073(5) 0.9209(2) 0.0615(10) Uani 1 1 d . . . . .
H12 H 0.888369 0.693347 0.988473 0.074 Uiso 1 1 calc R U . . .
C9 C 0.9722(3) 0.8903(5) 0.7532(3) 0.0593(9) Uani 1 1 d . . . . .
H9 H 1.036378 0.928579 0.801410 0.071 Uiso 1 1 calc R U . . .
C17 C -0.0241(3) 0.9206(5) 0.2462(3) 0.0585(9) Uani 1 1 d . . . . .
H17 H -0.045822 0.956205 0.293679 0.070 Uiso 1 1 calc R U . . .
C25 C 0.4689(3) 0.4296(5) 0.2247(3) 0.0586(9) Uani 1 1 d . . . . .
H25 H 0.402081 0.460240 0.177635 0.070 Uiso 1 1 calc R U . . .
C11 C 0.9320(3) 0.7863(6) 0.8871(2) 0.0627(10) Uani 1 1 d . . . . .
H11A H 0.997716 0.825948 0.931854 0.075 Uiso 1 1 calc R U . . .
C24 C 0.2067(3) 0.6658(6) 0.0891(2) 0.0707(11) Uani 1 1 d . . . . .
H24A H 0.140638 0.606864 0.068022 0.106 Uiso 1 1 calc R U . . .
H24B H 0.247307 0.616043 0.058104 0.106 Uiso 1 1 calc R U . . .
H24C H 0.193645 0.783438 0.070684 0.106 Uiso 1 1 calc R U . . .


_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 C4 1.356(3) . ?
O3 C8 1.428(3) . ?
O9 C30 1.362(3) . ?
O9 C32 1.416(4) . ?
O2 C5 1.344(4) . ?
O2 H2 0.8200 . ?
O8 C29 1.345(4) . ?
O8 H8 0.8200 . ?
O6 C14 1.362(3) . ?
O6 C16 1.427(4) . ?
O5 C13 1.341(4) . ?
O5 H5 0.8200 . ?
O12 C20 1.347(4) . ?
O12 C24 1.433(4) . ?
O4 C9 1.205(4) . ?
O1 C1 1.193(4) . ?
O10 C17 1.207(4) . ?
O7 C25 1.202(5) . ?
O11 C21 1.336(4) . ?
O11 H11 0.8200 . ?
C5 C6 1.378(4) . ?
C5 C4 1.410(4) . ?
C29 C28 1.387(4) . ?
C29 C30 1.401(4) . ?
C3 C4 1.366(4) . ?
C3 C2 1.398(4) . ?
C3 H3 0.9300 . ?
C30 C31 1.366(4) . ?
C6 C7 1.380(5) . ?
C6 H6 0.9300 . ?
C31 C26 1.393(4) . ?
C31 H31 0.9300 . ?
C13 C12 1.379(4) . ?
C13 C14 1.404(4) . ?
C15 C14 1.367(4) . ?
C15 C10 1.395(4) . ?
C15 H15 0.9300 . ?
C2 C7 1.374(5) . ?
C2 C1 1.460(5) . ?
C10 C11 1.377(5) . ?
C10 C9 1.460(5) . ?
C21 C22 1.374(5) . ?
C21 C20 1.414(4) . ?
C20 C19 1.368(4) . ?
C19 C18 1.405(4) . ?
C19 H19 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C26 C27 1.376(5) . ?
C26 C25 1.464(5) . ?
C27 C28 1.376(5) . ?
C27 H27 0.9300 . ?
C18 C23 1.377(5) . ?
C18 C17 1.458(5) . ?
C23 C22 1.367(5) . ?
C23 H23 0.9300 . ?
C28 H28 0.9300 . ?
C7 H7 0.9300 . ?
C1 H1 0.9300 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C22 H22 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C12 C11 1.375(5) . ?
C12 H12 0.9300 . ?
C9 H9 0.9300 . ?
C17 H17 0.9300 . ?
C25 H25 0.9300 . ?
C11 H11A 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C4 O3 C8 116.9(2) . . ?
C30 O9 C32 117.2(2) . . ?
C5 O2 H2 109.5 . . ?
C29 O8 H8 109.5 . . ?
C14 O6 C16 117.1(2) . . ?
C13 O5 H5 109.5 . . ?
C20 O12 C24 117.2(3) . . ?
C21 O11 H11 109.5 . . ?
O2 C5 C6 118.5(3) . . ?
O2 C5 C4 121.7(3) . . ?
C6 C5 C4 119.9(3) . . ?
O8 C29 C28 118.0(3) . . ?
O8 C29 C30 122.2(3) . . ?
C28 C29 C30 119.8(3) . . ?
C4 C3 C2 120.4(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
O9 C30 C31 126.4(3) . . ?
O9 C30 C29 113.5(3) . . ?
C31 C30 C29 120.1(3) . . ?
C5 C6 C7 119.9(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C30 C31 C26 119.9(3) . . ?
C30 C31 H31 120.1 . . ?
C26 C31 H31 120.1 . . ?
O3 C4 C3 126.4(3) . . ?
O3 C4 C5 114.0(2) . . ?
C3 C4 C5 119.5(3) . . ?
O5 C13 C12 118.5(3) . . ?
O5 C13 C14 122.4(3) . . ?
C12 C13 C14 119.0(3) . . ?
C14 C15 C10 120.2(3) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
C7 C2 C3 119.7(3) . . ?
C7 C2 C1 119.9(3) . . ?
C3 C2 C1 120.4(3) . . ?
C11 C10 C15 119.6(3) . . ?
C11 C10 C9 119.2(3) . . ?
C15 C10 C9 121.2(3) . . ?
O6 C14 C15 126.0(3) . . ?
O6 C14 C13 113.8(3) . . ?
C15 C14 C13 120.1(3) . . ?
O11 C21 C22 119.5(3) . . ?
O11 C21 C20 121.2(3) . . ?
C22 C21 C20 119.4(3) . . ?
O12 C20 C19 126.4(3) . . ?
O12 C20 C21 114.1(3) . . ?
C19 C20 C21 119.5(3) . . ?
C20 C19 C18 120.0(3) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C27 C26 C31 120.0(3) . . ?
C27 C26 C25 119.0(3) . . ?
C31 C26 C25 121.0(3) . . ?
C26 C27 C28 120.7(3) . . ?
C26 C27 H27 119.7 . . ?
C28 C27 H27 119.7 . . ?
C23 C18 C19 120.0(3) . . ?
C23 C18 C17 119.5(3) . . ?
C19 C18 C17 120.5(3) . . ?
C22 C23 C18 119.9(3) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?
C27 C28 C29 119.5(3) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C2 C7 C6 120.6(3) . . ?
C2 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
O1 C1 C2 126.2(4) . . ?
O1 C1 H1 116.9 . . ?
C2 C1 H1 116.9 . . ?
O9 C32 H32A 109.5 . . ?
O9 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O9 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C23 C22 C21 121.2(3) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C11 C12 C13 120.8(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
O4 C9 C10 125.9(3) . . ?
O4 C9 H9 117.0 . . ?
C10 C9 H9 117.0 . . ?
O10 C17 C18 126.2(3) . . ?
O10 C17 H17 116.9 . . ?
C18 C17 H17 116.9 . . ?
O7 C25 C26 125.9(3) . . ?
O7 C25 H25 117.0 . . ?
C26 C25 H25 117.0 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11A 119.9 . . ?
C10 C11 H11A 119.9 . . ?
O12 C24 H24A 109.5 . . ?
O12 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O12 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C32 O9 C30 C31 0.1(5) . . . . ?
C32 O9 C30 C29 179.6(3) . . . . ?
O8 C29 C30 O9 1.7(4) . . . . ?
C28 C29 C30 O9 -177.9(3) . . . . ?
O8 C29 C30 C31 -178.8(3) . . . . ?
C28 C29 C30 C31 1.6(5) . . . . ?
O2 C5 C6 C7 179.7(3) . . . . ?
C4 C5 C6 C7 0.2(5) . . . . ?
O9 C30 C31 C26 179.1(3) . . . . ?
C29 C30 C31 C26 -0.4(5) . . . . ?
C8 O3 C4 C3 2.1(5) . . . . ?
C8 O3 C4 C5 -178.0(3) . . . . ?
C2 C3 C4 O3 178.5(3) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
O2 C5 C4 O3 1.3(4) . . . . ?
C6 C5 C4 O3 -179.2(3) . . . . ?
O2 C5 C4 C3 -178.9(3) . . . . ?
C6 C5 C4 C3 0.7(5) . . . . ?
C4 C3 C2 C7 1.2(5) . . . . ?
C4 C3 C2 C1 -179.8(3) . . . . ?
C14 C15 C10 C11 -0.7(5) . . . . ?
C14 C15 C10 C9 179.8(3) . . . . ?
C16 O6 C14 C15 -5.6(5) . . . . ?
C16 O6 C14 C13 174.8(3) . . . . ?
C10 C15 C14 O6 -179.7(3) . . . . ?
C10 C15 C14 C13 -0.1(5) . . . . ?
O5 C13 C14 O6 -0.5(5) . . . . ?
C12 C13 C14 O6 -179.7(3) . . . . ?
O5 C13 C14 C15 179.9(3) . . . . ?
C12 C13 C14 C15 0.7(5) . . . . ?
C24 O12 C20 C19 2.2(6) . . . . ?
C24 O12 C20 C21 -178.1(3) . . . . ?
O11 C21 C20 O12 0.4(5) . . . . ?
C22 C21 C20 O12 179.0(4) . . . . ?
O11 C21 C20 C19 -179.8(4) . . . . ?
C22 C21 C20 C19 -1.3(6) . . . . ?
O12 C20 C19 C18 179.8(3) . . . . ?
C21 C20 C19 C18 0.1(5) . . . . ?
C30 C31 C26 C27 -1.0(5) . . . . ?
C30 C31 C26 C25 180.0(3) . . . . ?
C31 C26 C27 C28 1.1(5) . . . . ?
C25 C26 C27 C28 -179.8(3) . . . . ?
C20 C19 C18 C23 0.2(5) . . . . ?
C20 C19 C18 C17 -179.6(3) . . . . ?
C19 C18 C23 C22 0.8(6) . . . . ?
C17 C18 C23 C22 -179.4(4) . . . . ?
C26 C27 C28 C29 0.1(6) . . . . ?
O8 C29 C28 C27 178.9(3) . . . . ?
C30 C29 C28 C27 -1.4(5) . . . . ?
C3 C2 C7 C6 -0.4(5) . . . . ?
C1 C2 C7 C6 -179.4(4) . . . . ?
C5 C6 C7 C2 -0.3(6) . . . . ?
C7 C2 C1 O1 -178.8(4) . . . . ?
C3 C2 C1 O1 2.1(6) . . . . ?
C18 C23 C22 C21 -2.1(6) . . . . ?
O11 C21 C22 C23 -179.2(4) . . . . ?
C20 C21 C22 C23 2.3(6) . . . . ?
O5 C13 C12 C11 -179.7(4) . . . . ?
C14 C13 C12 C11 -0.4(6) . . . . ?
C11 C10 C9 O4 178.7(4) . . . . ?
C15 C10 C9 O4 -1.8(6) . . . . ?
C23 C18 C17 O10 179.1(4) . . . . ?
C19 C18 C17 O10 -1.1(6) . . . . ?
C27 C26 C25 O7 179.7(4) . . . . ?
C31 C26 C25 O7 -1.2(6) . . . . ?
C13 C12 C11 C10 -0.3(6) . . . . ?
C15 C10 C11 C12 0.9(6) . . . . ?
C9 C10 C11 C12 -179.6(4) . . . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 'Solution Crystallization'
####################################################################### 
# 
# 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_ex1156vn8_a
_database_code_depnum_ccdc_archive 'CCDC 1990284'
loop_
_audit_author_name
_audit_author_address
'Dr. K. Srinivasan'
;Bharathiar University
India
;
_audit_update_record             
;
2020-07-19 deposited with the CCDC.	2021-01-13 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_RINTA01_ex1156vn8_a         
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: Since the size of the crystal is very small, the Rint value exceeds 0.18
;
# Added during the CSD deposition process: Sunday 19 July 2020 06:31 AM
# end Validation Reply Form



_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        Vanillin
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 O3'
_chemical_formula_weight         152.14

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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   16.4359(13)
_cell_length_b                   3.8887(3)
_cell_length_c                   45.843(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2930.0(4)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6926
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      21.8

_exptl_crystal_description       needle
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Mo
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            75071
_diffrn_reflns_av_unetI/netI     0.1031
_diffrn_reflns_av_R_equivalents  0.1905
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -58
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_theta_min         2.478
_diffrn_reflns_theta_max         27.127
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6393
_reflns_number_gt                3326
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.972
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.998

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_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)+(0.0352P)²+0.3025P] 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       0.0044(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1218 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.8(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         6393
_refine_ls_number_parameters     406
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1558
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1040
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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
O9 O 0.18553(18) 0.2395(10) 0.53470(7) 0.0477(10) Uani 1 1 d . . . . .
O12 O 0.14976(18) 0.1753(10) 0.65851(7) 0.0539(11) Uani 1 1 d . . . . .
O3 O 0.5972(2) 0.2564(9) 0.34097(7) 0.0497(10) Uani 1 1 d . . . . .
O5 O 0.22561(18) 0.7404(11) 0.44957(8) 0.0541(11) Uani 1 1 d . . . . .
O6 O 0.53826(18) 0.7600(9) 0.46860(7) 0.0471(10) Uani 1 1 d . . . . .
O8 O 0.49795(19) 0.2922(11) 0.55401(8) 0.0583(12) Uani 1 1 d . . . . .
O7 O 0.12892(18) -0.0380(11) 0.58346(7) 0.0536(11) Uani 1 1 d . . . . .
H7 H 0.105035 0.056142 0.569936 0.080 Uiso 1 1 calc R U . . .
O10 O 0.0216(2) -0.0943(12) 0.63173(7) 0.0576(11) Uani 1 1 d . . . . .
H10 H 0.065044 -0.027477 0.625051 0.086 Uiso 1 1 calc R U . . .
O1 O 0.7092(2) -0.0496(11) 0.37369(7) 0.0565(11) Uani 1 1 d . . . . .
H1 H 0.664813 0.033274 0.377836 0.085 Uiso 1 1 calc R U . . .
O4 O 0.59579(18) 1.0322(12) 0.41984(7) 0.0552(12) Uani 1 1 d . . . . .
H4 H 0.619063 0.949947 0.434043 0.083 Uiso 1 1 calc R U . . .
O11 O 0.0333(3) 0.4647(13) 0.76201(8) 0.0776(14) Uani 1 1 d . . . . .
C22 C 0.2431(3) 0.1453(13) 0.55449(10) 0.0332(12) Uani 1 1 d . . . . .
C9 C 0.5141(3) 1.0104(14) 0.42371(11) 0.0352(13) Uani 1 1 d . . . . .
C13 C 0.3990(3) 0.8354(13) 0.45168(10) 0.0361(13) Uani 1 1 d . . . . .
H13 H 0.376846 0.733238 0.468210 0.043 Uiso 1 1 calc R U . . .
C21 C 0.3247(3) 0.1850(13) 0.55179(10) 0.0333(12) Uani 1 1 d . . . . .
H21 H 0.346148 0.288635 0.535209 0.040 Uiso 1 1 calc R U . . .
C12 C 0.3485(3) 0.9588(13) 0.42956(10) 0.0324(13) Uani 1 1 d . . . . .
C10 C 0.4648(3) 1.1347(14) 0.40222(10) 0.0422(14) Uani 1 1 d . . . . .
H10A H 0.487104 1.234434 0.385605 0.051 Uiso 1 1 calc R U . . .
C30 C 0.0786(3) 0.1612(14) 0.67451(10) 0.0394(14) Uani 1 1 d . . . . .
C14 C 0.4818(3) 0.8667(13) 0.44873(10) 0.0321(12) Uani 1 1 d . . . . .
C15 C 0.2604(3) 0.9063(15) 0.43129(11) 0.0397(14) Uani 1 1 d . . . . .
H15 H 0.228667 1.010344 0.417005 0.048 Uiso 1 1 calc R U . . .
C25 C 0.0138(3) 0.0166(13) 0.65968(11) 0.0413(14) Uani 1 1 d . . . . .
C2 C 0.7978(3) -0.1023(14) 0.33407(10) 0.0426(14) Uani 1 1 d . . . . .
H2 H 0.835535 -0.207383 0.346262 0.051 Uiso 1 1 calc R U . . .
C6 C 0.6672(3) 0.1617(13) 0.32716(11) 0.0387(14) Uani 1 1 d . . . . .
O2 O 0.7367(3) 0.2968(13) 0.23852(8) 0.0857(16) Uani 1 1 d . . . . .
C20 C 0.3763(3) 0.0711(14) 0.57377(10) 0.0336(13) Uani 1 1 d . . . . .
C17 C 0.2104(3) -0.0045(14) 0.57968(10) 0.0362(13) Uani 1 1 d . . . . .
C23 C 0.4631(3) 0.1295(15) 0.57283(11) 0.0430(14) Uani 1 1 d . . . . .
H23 H 0.494465 0.035774 0.587719 0.052 Uiso 1 1 calc R U . . .
C1 C 0.7249(3) 0.0040(14) 0.34498(10) 0.0390(13) Uani 1 1 d . . . . .
C5 C 0.6849(3) 0.2118(14) 0.29813(11) 0.0419(13) Uani 1 1 d . . . . .
H5 H 0.647263 0.318341 0.285989 0.050 Uiso 1 1 calc R U . . .
C19 C 0.3439(3) -0.0877(14) 0.59822(10) 0.0420(14) Uani 1 1 d . . . . .
H19 H 0.378446 -0.169127 0.612737 0.050 Uiso 1 1 calc R U . . .
C4 C 0.7588(3) 0.1036(14) 0.28702(10) 0.0420(13) Uani 1 1 d . . . . .
C3 C 0.8156(3) -0.0539(14) 0.30488(11) 0.0438(14) Uani 1 1 d . . . . .
H3 H 0.865215 -0.126389 0.297323 0.053 Uiso 1 1 calc R U . . .
C11 C 0.3818(3) 1.1110(14) 0.40541(10) 0.0407(14) Uani 1 1 d . . . . .
H11 H 0.347906 1.199336 0.391000 0.049 Uiso 1 1 calc R U . . .
C18 C 0.2612(3) -0.1256(14) 0.60116(10) 0.0409(13) Uani 1 1 d . . . . .
H18 H 0.239762 -0.232650 0.617584 0.049 Uiso 1 1 calc R U . . .
C16 C 0.5101(3) 0.6198(14) 0.49535(10) 0.0454(15) Uani 1 1 d . . . . .
H16A H 0.477823 0.787838 0.505402 0.068 Uiso 1 1 calc R U . . .
H16B H 0.555863 0.557073 0.507244 0.068 Uiso 1 1 calc R U . . .
H16C H 0.477701 0.419539 0.491496 0.068 Uiso 1 1 calc R U . . .
C29 C 0.0699(3) 0.2693(13) 0.70280(10) 0.0420(14) Uani 1 1 d . . . . .
H29 H 0.113570 0.365792 0.712769 0.050 Uiso 1 1 calc R U . . .
C24 C 0.2133(3) 0.3877(15) 0.50792(10) 0.0487(15) Uani 1 1 d . . . . .
H24A H 0.245715 0.587252 0.512059 0.073 Uiso 1 1 calc R U . . .
H24B H 0.167368 0.452737 0.496241 0.073 Uiso 1 1 calc R U . . .
H24C H 0.245573 0.222432 0.497508 0.073 Uiso 1 1 calc R U . . .
C27 C -0.0696(3) 0.0869(15) 0.70142(11) 0.0496(15) Uani 1 1 d . . . . .
H27 H -0.119725 0.063158 0.710584 0.060 Uiso 1 1 calc R U . . .
C28 C -0.0050(3) 0.2323(14) 0.71629(10) 0.0430(14) Uani 1 1 d . . . . .
C32 C 0.2210(3) 0.2982(17) 0.67292(11) 0.0569(17) Uani 1 1 d . . . . .
H32A H 0.211601 0.527454 0.679922 0.085 Uiso 1 1 calc R U . . .
H32B H 0.265777 0.299625 0.659461 0.085 Uiso 1 1 calc R U . . .
H32C H 0.233648 0.150335 0.689064 0.085 Uiso 1 1 calc R U . . .
C26 C -0.0598(3) -0.0237(15) 0.67288(11) 0.0492(15) Uani 1 1 d . . . . .
H26 H -0.102920 -0.124015 0.662890 0.059 Uiso 1 1 calc R U . . .
C31 C -0.0175(4) 0.3454(17) 0.74622(13) 0.0638(19) Uani 1 1 d . . . . .
H31 H -0.069705 0.323048 0.753789 0.077 Uiso 1 1 calc R U . . .
C7 C 0.7797(4) 0.1570(17) 0.25623(12) 0.0589(17) Uani 1 1 d . . . . .
H7A H 0.829948 0.076754 0.249872 0.071 Uiso 1 1 calc R U . . .
C8 C 0.5348(3) 0.4141(16) 0.32385(11) 0.0584(17) Uani 1 1 d . . . . .
H8A H 0.555215 0.622902 0.315398 0.088 Uiso 1 1 calc R U . . .
H8B H 0.488909 0.465574 0.336042 0.088 Uiso 1 1 calc R U . . .
H8C H 0.518379 0.259779 0.308601 0.088 Uiso 1 1 calc R U . . .


_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
O9 C22 1.362(5) . ?
O9 C24 1.431(6) . ?
O12 C30 1.382(5) . ?
O12 C32 1.427(5) . ?
O3 C6 1.363(6) . ?
O3 C8 1.430(5) . ?
O5 C15 1.203(6) . ?
O6 C14 1.365(5) . ?
O6 C16 1.420(5) . ?
O8 C23 1.214(6) . ?
O7 C17 1.357(5) . ?
O7 H7 0.8200 . ?
O10 C25 1.358(5) . ?
O10 H10 0.8200 . ?
O1 C1 1.358(5) . ?
O1 H1 0.8200 . ?
O4 C9 1.357(5) . ?
O4 H4 0.8200 . ?
O11 C31 1.198(7) . ?
C22 C21 1.355(6) . ?
C22 C17 1.401(7) . ?
C9 C10 1.364(6) . ?
C9 C14 1.381(6) . ?
C13 C14 1.373(6) . ?
C13 C12 1.395(6) . ?
C13 H13 0.9300 . ?
C21 C20 1.390(6) . ?
C21 H21 0.9300 . ?
C12 C11 1.370(6) . ?
C12 C15 1.464(7) . ?
C10 C11 1.375(7) . ?
C10 H10A 0.9300 . ?
C30 C29 1.371(6) . ?
C30 C25 1.382(6) . ?
C15 H15 0.9300 . ?
C25 C26 1.362(6) . ?
C2 C1 1.362(6) . ?
C2 C3 1.383(6) . ?
C2 H2 0.9300 . ?
C6 C5 1.376(6) . ?
C6 C1 1.395(7) . ?
O2 C7 1.206(6) . ?
C20 C19 1.386(6) . ?
C20 C23 1.445(7) . ?
C17 C18 1.374(6) . ?
C23 H23 0.9300 . ?
C5 C4 1.382(7) . ?
C5 H5 0.9300 . ?
C19 C18 1.374(6) . ?
C19 H19 0.9300 . ?
C4 C3 1.384(7) . ?
C4 C7 1.468(7) . ?
C3 H3 0.9300 . ?
C11 H11 0.9300 . ?
C18 H18 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C29 C28 1.386(6) . ?
C29 H29 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C27 C28 1.382(7) . ?
C27 C26 1.386(7) . ?
C27 H27 0.9300 . ?
C28 C31 1.455(7) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C26 H26 0.9300 . ?
C31 H31 0.9300 . ?
C7 H7A 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C22 O9 C24 117.2(4) . . ?
C30 O12 C32 117.6(4) . . ?
C6 O3 C8 117.7(4) . . ?
C14 O6 C16 118.2(4) . . ?
C17 O7 H7 109.5 . . ?
C25 O10 H10 109.5 . . ?
C1 O1 H1 109.5 . . ?
C9 O4 H4 109.5 . . ?
C21 C22 O9 126.6(4) . . ?
C21 C22 C17 120.1(4) . . ?
O9 C22 C17 113.2(4) . . ?
O4 C9 C10 118.1(4) . . ?
O4 C9 C14 120.9(4) . . ?
C10 C9 C14 121.0(4) . . ?
C14 C13 C12 119.2(4) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C22 C21 C20 120.1(4) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 C15 119.9(4) . . ?
C13 C12 C15 120.1(4) . . ?
C9 C10 C11 119.2(5) . . ?
C9 C10 H10A 120.4 . . ?
C11 C10 H10A 120.4 . . ?
C29 C30 O12 125.3(4) . . ?
C29 C30 C25 120.7(4) . . ?
O12 C30 C25 114.0(4) . . ?
O6 C14 C13 125.5(4) . . ?
O6 C14 C9 114.6(4) . . ?
C13 C14 C9 119.9(4) . . ?
O5 C15 C12 125.7(5) . . ?
O5 C15 H15 117.2 . . ?
C12 C15 H15 117.2 . . ?
O10 C25 C26 117.8(5) . . ?
O10 C25 C30 121.4(4) . . ?
C26 C25 C30 120.8(5) . . ?
C1 C2 C3 120.0(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
O3 C6 C5 126.2(5) . . ?
O3 C6 C1 114.9(4) . . ?
C5 C6 C1 119.0(5) . . ?
C19 C20 C21 119.6(4) . . ?
C19 C20 C23 118.2(4) . . ?
C21 C20 C23 122.1(4) . . ?
O7 C17 C18 118.4(4) . . ?
O7 C17 C22 121.6(4) . . ?
C18 C17 C22 120.0(4) . . ?
O8 C23 C20 124.7(5) . . ?
O8 C23 H23 117.6 . . ?
C20 C23 H23 117.6 . . ?
O1 C1 C2 118.5(5) . . ?
O1 C1 C6 120.4(4) . . ?
C2 C1 C6 121.1(5) . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C18 C19 C20 120.5(4) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C5 C4 C3 120.6(5) . . ?
C5 C4 C7 121.1(5) . . ?
C3 C4 C7 118.3(5) . . ?
C2 C3 C4 119.3(5) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C12 C11 C10 120.8(4) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C17 C18 C19 119.6(4) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
O6 C16 H16A 109.5 . . ?
O6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C30 C29 C28 118.9(5) . . ?
C30 C29 H29 120.6 . . ?
C28 C29 H29 120.6 . . ?
O9 C24 H24A 109.5 . . ?
O9 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O9 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C28 C27 C26 120.2(5) . . ?
C28 C27 H27 119.9 . . ?
C26 C27 H27 119.9 . . ?
C27 C28 C29 120.3(4) . . ?
C27 C28 C31 118.7(5) . . ?
C29 C28 C31 121.0(5) . . ?
O12 C32 H32A 109.5 . . ?
O12 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O12 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C25 C26 C27 119.1(5) . . ?
C25 C26 H26 120.4 . . ?
C27 C26 H26 120.4 . . ?
O11 C31 C28 126.1(6) . . ?
O11 C31 H31 117.0 . . ?
C28 C31 H31 117.0 . . ?
O2 C7 C4 125.0(6) . . ?
O2 C7 H7A 117.5 . . ?
C4 C7 H7A 117.5 . . ?
O3 C8 H8A 109.5 . . ?
O3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
C24 O9 C22 C21 1.7(7) . . . . ?
C24 O9 C22 C17 -178.6(5) . . . . ?
O9 C22 C21 C20 -179.1(5) . . . . ?
C17 C22 C21 C20 1.3(8) . . . . ?
C14 C13 C12 C11 -0.5(7) . . . . ?
C14 C13 C12 C15 175.7(4) . . . . ?
O4 C9 C10 C11 179.0(5) . . . . ?
C14 C9 C10 C11 -1.1(8) . . . . ?
C32 O12 C30 C29 2.9(8) . . . . ?
C32 O12 C30 C25 -175.6(5) . . . . ?
C16 O6 C14 C13 -3.4(7) . . . . ?
C16 O6 C14 C9 177.9(5) . . . . ?
C12 C13 C14 O6 179.6(4) . . . . ?
C12 C13 C14 C9 -1.8(8) . . . . ?
O4 C9 C14 O6 1.3(7) . . . . ?
C10 C9 C14 O6 -178.7(5) . . . . ?
O4 C9 C14 C13 -177.5(5) . . . . ?
C10 C9 C14 C13 2.6(8) . . . . ?
C11 C12 C15 O5 170.5(5) . . . . ?
C13 C12 C15 O5 -5.6(8) . . . . ?
C29 C30 C25 O10 -179.5(5) . . . . ?
O12 C30 C25 O10 -0.9(7) . . . . ?
C29 C30 C25 C26 -0.4(8) . . . . ?
O12 C30 C25 C26 178.2(5) . . . . ?
C8 O3 C6 C5 2.0(7) . . . . ?
C8 O3 C6 C1 -178.9(5) . . . . ?
C22 C21 C20 C19 1.0(8) . . . . ?
C22 C21 C20 C23 -175.5(5) . . . . ?
C21 C22 C17 O7 177.9(5) . . . . ?
O9 C22 C17 O7 -1.9(7) . . . . ?
C21 C22 C17 C18 -2.9(8) . . . . ?
O9 C22 C17 C18 177.4(5) . . . . ?
C19 C20 C23 O8 -173.1(6) . . . . ?
C21 C20 C23 O8 3.4(9) . . . . ?
C3 C2 C1 O1 179.6(5) . . . . ?
C3 C2 C1 C6 0.1(8) . . . . ?
O3 C6 C1 O1 0.9(7) . . . . ?
C5 C6 C1 O1 -179.9(5) . . . . ?
O3 C6 C1 C2 -179.7(5) . . . . ?
C5 C6 C1 C2 -0.5(8) . . . . ?
O3 C6 C5 C4 179.7(5) . . . . ?
C1 C6 C5 C4 0.5(7) . . . . ?
C21 C20 C19 C18 -1.6(8) . . . . ?
C23 C20 C19 C18 175.1(5) . . . . ?
C6 C5 C4 C3 -0.3(8) . . . . ?
C6 C5 C4 C7 -179.4(5) . . . . ?
C1 C2 C3 C4 0.1(8) . . . . ?
C5 C4 C3 C2 0.0(8) . . . . ?
C7 C4 C3 C2 179.1(5) . . . . ?
C13 C12 C11 C10 2.0(8) . . . . ?
C15 C12 C11 C10 -174.1(5) . . . . ?
C9 C10 C11 C12 -1.2(8) . . . . ?
O7 C17 C18 C19 -178.4(5) . . . . ?
C22 C17 C18 C19 2.3(8) . . . . ?
C20 C19 C18 C17 -0.1(8) . . . . ?
O12 C30 C29 C28 -178.6(5) . . . . ?
C25 C30 C29 C28 -0.2(8) . . . . ?
C26 C27 C28 C29 0.1(9) . . . . ?
C26 C27 C28 C31 -180.0(5) . . . . ?
C30 C29 C28 C27 0.4(8) . . . . ?
C30 C29 C28 C31 -179.5(5) . . . . ?
O10 C25 C26 C27 180.0(5) . . . . ?
C30 C25 C26 C27 0.9(8) . . . . ?
C28 C27 C26 C25 -0.7(9) . . . . ?
C27 C28 C31 O11 177.4(6) . . . . ?
C29 C28 C31 O11 -2.7(10) . . . . ?
C5 C4 C7 O2 0.7(10) . . . . ?
C3 C4 C7 O2 -178.4(6) . . . . ?

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.040


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?



_publcif_funding_html            
;
;
_exptl_crystal_recrystallization_method 'Solution crystallization'
_chemical_properties_physical    Air-sensitive
