# Supplementary Information (SI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_hjt20240404b1_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2349262'
loop_
_audit_author_name
_audit_author_address
'Spirocyclic alcohol'
;Zhejiang university of technology
China
;
_audit_update_record             
;
2024-04-18 deposited with the CCDC.	2025-05-27 downloaded from the CCDC.
;
_audit_creation_date             2024-04-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 O2'
_chemical_formula_sum            'C18 H16 O2'
_chemical_formula_weight         264.31
_chemical_absolute_configuration ?
_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 0.0137 0.0067 '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 0.0389 0.0241 '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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   5.9260(3)
_cell_length_b                   11.6332(6)
_cell_length_c                   19.3715(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1335.44(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9970
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      63.37
_cell_measurement_theta_min      3.86
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.427
_exptl_absorpt_correction_T_max  0.7523
_exptl_absorpt_correction_T_min  0.6446
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0675 before and 0.0544 after correction.
The Ratio of minimum to maximum transmission is 0.8568.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13849
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         63.425
_diffrn_reflns_theta_min         3.856
_diffrn_ambient_temperature      150.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.14
_diffrn_source_power             0.0796404
_diffrn_source_target            Mo
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.708
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                3163
_reflns_number_total             3273
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1291 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+0.1290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0801
_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)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C5(H5a,H5b), C17(H17a,H17b)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1a), C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45511(18) 0.50557(8) 0.73191(5) 0.0260(2) Uani 1 1 d . . . . .
H1 H 0.461511 0.573452 0.746567 0.039 Uiso 1 1 calc R U . . .
O2 O 0.50860(17) 0.21342(8) 0.69382(5) 0.0241(2) Uani 1 1 d . . . . .
C1 C 0.3266(3) 0.43247(14) 0.48123(8) 0.0357(4) Uani 1 1 d . . . . .
H1A H 0.314534 0.461754 0.435604 0.043 Uiso 1 1 calc R U . . .
C2 C 0.1645(3) 0.45994(13) 0.52945(8) 0.0324(3) Uani 1 1 d . . . . .
H2 H 0.041996 0.508101 0.516645 0.039 Uiso 1 1 calc R U . . .
C3 C 0.1777(2) 0.41790(11) 0.59707(7) 0.0249(3) Uani 1 1 d . . . . .
C4 C 0.0067(3) 0.45176(13) 0.65034(8) 0.0320(3) Uani 1 1 d . . . . .
H4A H -0.141744 0.462261 0.627772 0.038 Uiso 1 1 calc R U . . .
H4B H 0.051164 0.526189 0.671059 0.038 Uiso 1 1 calc R U . . .
C5 C -0.0148(2) 0.36179(14) 0.70726(8) 0.0308(3) Uani 1 1 d . . . . .
H5A H -0.081242 0.290812 0.687699 0.037 Uiso 1 1 calc R U . . .
H5B H -0.118563 0.390754 0.743348 0.037 Uiso 1 1 calc R U . . .
C6 C 0.2135(2) 0.33320(11) 0.74011(7) 0.0217(3) Uani 1 1 d . . . . .
C7 C 0.3238(2) 0.43817(11) 0.77771(7) 0.0222(3) Uani 1 1 d . . . . .
H7 H 0.202380 0.487120 0.798214 0.027 Uiso 1 1 calc R U . . .
C8 C 0.4580(2) 0.38263(11) 0.83523(6) 0.0225(3) Uani 1 1 d . . . . .
C9 C 0.6314(3) 0.42953(12) 0.87393(7) 0.0265(3) Uani 1 1 d . . . . .
H9 H 0.679840 0.506317 0.866246 0.032 Uiso 1 1 calc R U . . .
C10 C 0.7335(3) 0.36183(14) 0.92440(7) 0.0303(3) Uani 1 1 d . . . . .
H10 H 0.852739 0.392667 0.951454 0.036 Uiso 1 1 calc R U . . .
C11 C 0.5078(3) 0.36233(15) 0.49868(7) 0.0333(3) Uani 1 1 d . . . . .
H11 H 0.621360 0.345350 0.465603 0.040 Uiso 1 1 calc R U . . .
C12 C 0.5210(3) 0.31734(12) 0.56493(7) 0.0258(3) Uani 1 1 d . . . . .
H12 H 0.642116 0.267714 0.576923 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3570(2) 0.34472(11) 0.61404(6) 0.0203(3) Uani 1 1 d . . . . .
C14 C 0.6618(3) 0.24901(14) 0.93546(8) 0.0335(3) Uani 1 1 d . . . . .
H14 H 0.732614 0.203636 0.970007 0.040 Uiso 1 1 calc R U . . .
C15 C 0.4879(3) 0.20261(13) 0.89638(7) 0.0315(3) Uani 1 1 d . . . . .
H15 H 0.439862 0.125659 0.903737 0.038 Uiso 1 1 calc R U . . .
C16 C 0.3848(3) 0.27036(12) 0.84630(7) 0.0252(3) Uani 1 1 d . . . . .
C17 C 0.1942(2) 0.24191(12) 0.79770(7) 0.0273(3) Uani 1 1 d . . . . .
H17A H 0.046679 0.247388 0.821458 0.033 Uiso 1 1 calc R U . . .
H17B H 0.211616 0.163442 0.778652 0.033 Uiso 1 1 calc R U . . .
C18 C 0.3736(2) 0.29106(11) 0.68356(6) 0.0180(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C7 1.4169(16) . ?
O2 C18 1.2226(16) . ?
C1 H1A 0.9500 . ?
C1 C2 1.378(3) . ?
C1 C11 1.390(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.400(2) . ?
C3 C4 1.499(2) . ?
C3 C13 1.4008(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.526(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5321(19) . ?
C6 C7 1.5649(18) . ?
C6 C17 1.5445(19) . ?
C6 C18 1.5299(17) . ?
C7 H7 1.0000 . ?
C7 C8 1.5136(19) . ?
C8 C9 1.384(2) . ?
C8 C16 1.3928(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.394(2) . ?
C10 H10 0.9500 . ?
C10 C14 1.396(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.3882(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.397(2) . ?
C13 C18 1.4876(18) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.391(2) . ?
C16 C17 1.507(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

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
C7 O1 H1 109.5 . . ?
C2 C1 H1A 119.7 . . ?
C2 C1 C11 120.66(14) . . ?
C11 C1 H1A 119.7 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 120.95(14) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 120.96(13) . . ?
C2 C3 C13 118.30(14) . . ?
C13 C3 C4 120.73(12) . . ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C3 C4 C5 111.96(12) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C4 C5 C6 112.03(12) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C5 C6 C7 113.13(12) . . ?
C5 C6 C17 112.57(12) . . ?
C17 C6 C7 103.37(11) . . ?
C18 C6 C5 108.66(11) . . ?
C18 C6 C7 108.93(10) . . ?
C18 C6 C17 110.05(11) . . ?
O1 C7 C6 111.70(10) . . ?
O1 C7 H7 109.2 . . ?
O1 C7 C8 114.13(11) . . ?
C6 C7 H7 109.2 . . ?
C8 C7 C6 103.24(11) . . ?
C8 C7 H7 109.2 . . ?
C9 C8 C7 128.35(13) . . ?
C9 C8 C16 121.16(13) . . ?
C16 C8 C7 110.49(12) . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.66(13) . . ?
C10 C9 H9 120.7 . . ?
C9 C10 H10 119.8 . . ?
C9 C10 C14 120.45(15) . . ?
C14 C10 H10 119.8 . . ?
C1 C11 H11 120.3 . . ?
C12 C11 C1 119.31(15) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.30(14) . . ?
C13 C12 H12 119.8 . . ?
C3 C13 C18 121.18(12) . . ?
C12 C13 C3 120.44(12) . . ?
C12 C13 C18 118.35(12) . . ?
C10 C14 H14 119.7 . . ?
C15 C14 C10 120.52(15) . . ?
C15 C14 H14 119.7 . . ?
C14 C15 H15 120.5 . . ?
C14 C15 C16 119.08(14) . . ?
C16 C15 H15 120.5 . . ?
C8 C16 C17 110.07(13) . . ?
C15 C16 C8 120.13(14) . . ?
C15 C16 C17 129.81(14) . . ?
C6 C17 H17A 110.9 . . ?
C6 C17 H17B 110.9 . . ?
C16 C17 C6 104.16(11) . . ?
C16 C17 H17A 110.9 . . ?
C16 C17 H17B 110.9 . . ?
H17A C17 H17B 108.9 . . ?
O2 C18 C6 121.73(12) . . ?
O2 C18 C13 120.03(11) . . ?
C13 C18 C6 118.21(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C7 C8 C9 40.98(18) . . . . ?
O1 C7 C8 C16 -138.81(11) . . . . ?
C1 C2 C3 C4 177.39(14) . . . . ?
C1 C2 C3 C13 -1.6(2) . . . . ?
C1 C11 C12 C13 -1.6(2) . . . . ?
C2 C1 C11 C12 1.7(2) . . . . ?
C2 C3 C4 C5 154.62(14) . . . . ?
C2 C3 C13 C12 1.7(2) . . . . ?
C2 C3 C13 C18 -176.12(12) . . . . ?
C3 C4 C5 C6 53.74(17) . . . . ?
C3 C13 C18 O2 167.91(12) . . . . ?
C3 C13 C18 C6 -10.25(18) . . . . ?
C4 C3 C13 C12 -177.31(13) . . . . ?
C4 C3 C13 C18 4.88(19) . . . . ?
C4 C5 C6 C7 63.43(16) . . . . ?
C4 C5 C6 C17 -179.83(11) . . . . ?
C4 C5 C6 C18 -57.67(15) . . . . ?
C5 C6 C7 O1 -87.29(14) . . . . ?
C5 C6 C7 C8 149.65(12) . . . . ?
C5 C6 C17 C16 -150.58(12) . . . . ?
C5 C6 C18 O2 -142.29(13) . . . . ?
C5 C6 C18 C13 35.84(16) . . . . ?
C6 C7 C8 C9 162.41(13) . . . . ?
C6 C7 C8 C16 -17.38(14) . . . . ?
C7 C6 C17 C16 -28.16(13) . . . . ?
C7 C6 C18 O2 94.06(15) . . . . ?
C7 C6 C18 C13 -87.82(13) . . . . ?
C7 C8 C9 C10 -179.42(13) . . . . ?
C7 C8 C16 C15 179.03(13) . . . . ?
C7 C8 C16 C17 -0.60(15) . . . . ?
C8 C9 C10 C14 0.0(2) . . . . ?
C8 C16 C17 C6 18.64(15) . . . . ?
C9 C8 C16 C15 -0.8(2) . . . . ?
C9 C8 C16 C17 179.59(12) . . . . ?
C9 C10 C14 C15 0.0(2) . . . . ?
C10 C14 C15 C16 -0.4(2) . . . . ?
C11 C1 C2 C3 -0.1(2) . . . . ?
C11 C12 C13 C3 -0.1(2) . . . . ?
C11 C12 C13 C18 177.79(13) . . . . ?
C12 C13 C18 O2 -9.94(18) . . . . ?
C12 C13 C18 C6 171.90(12) . . . . ?
C13 C3 C4 C5 -26.41(18) . . . . ?
C14 C15 C16 C8 0.8(2) . . . . ?
C14 C15 C16 C17 -179.65(14) . . . . ?
C15 C16 C17 C6 -160.94(15) . . . . ?
C16 C8 C9 C10 0.3(2) . . . . ?
C17 C6 C7 O1 150.67(11) . . . . ?
C17 C6 C7 C8 27.61(13) . . . . ?
C17 C6 C18 O2 -18.61(17) . . . . ?
C17 C6 C18 C13 159.51(11) . . . . ?
C18 C6 C7 O1 33.67(15) . . . . ?
C18 C6 C7 C8 -89.40(12) . . . . ?
C18 C6 C17 C16 88.05(13) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
