#------------------------------------------------------------------------------
#$Date: 2025-03-07 17:30:27 +0100 (Fri 07 de Mar de 2025) $
#$Revision: 298328 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/99/7159938.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7159938
loop_
_publ_author_name
'Pocock, Ian A.'
'Doulcet, Julien'
'Rice, Craig R.'
'Sweeney, Joseph B.'
'Gill, Duncan M.'
_publ_section_title
;
 Stereocontrolled synthesis of the aconitine D ring from D-glucose.
;
_journal_issue                   21
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4347
_journal_page_last               4352
_journal_paper_doi               10.1039/d4ob00561a
_journal_volume                  22
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C17 H20 O6'
_chemical_formula_sum            'C17 H20 O6'
_chemical_formula_weight         320.344
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_Int_Tables_number      4
_audit_creation_date             2023-06-19
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2024-03-27 deposited with the CCDC.	2024-05-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.038(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3489(4)
_cell_length_b                   5.0069(2)
_cell_length_c                   18.7570(7)
_cell_measurement_reflns_used    3696
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      72.46
_cell_measurement_theta_min      4.72
_cell_volume                     783.95(6)
_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)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 0.9653
_diffrn_measured_fraction_theta_max 0.9570
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_Laue_measured_fraction_full 0.9653
_diffrn_reflns_Laue_measured_fraction_max 0.9570
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4136
_diffrn_reflns_point_group_measured_fraction_full 0.7683
_diffrn_reflns_point_group_measured_fraction_max 0.7478
_diffrn_reflns_theta_full        67.6786
_diffrn_reflns_theta_max         72.46
_diffrn_reflns_theta_min         4.72
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       plate
_exptl_crystal_F_000             341.282
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.3997
_refine_diff_density_min         -0.5117
_refine_diff_density_rms         0.1258
_refine_ls_abs_structure_details
'Hooft, R.W.W., Straver, L.H., Spek, A.L. (2010). J. Appl. Cryst., 43, 665-668.'
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_d_res_high            0.8085
_refine_ls_d_res_low             9.3770
_refine_ls_goodness_of_fit_ref   1.0507
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    35
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2327
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.0507
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0881
_refine_ls_shift/su_max          -0.0023
_refine_ls_shift/su_mean         0.0006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1307P)²+1.8021P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2285
_refine_ls_wR_factor_ref         0.2359
_reflns_Friedel_coverage         0.480
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              6
_reflns_limit_k_min              -5
_reflns_limit_l_max              23
_reflns_limit_l_min              -22
_reflns_number_gt                2111
_reflns_number_total             2327
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob00561a2.cif
_cod_data_source_block           cu_IanP_chiral_0m
_cod_depositor_comments
;
          Adding full bibliography for 7159938.cif.

2025-03-06
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C8.5 H10 O3'
_cod_original_formula_weight         160.172
_cod_original_formula_moiety         '0.5(C17 H20 O6)'
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_Hall     ' P 2yb'
_cod_database_code               7159938
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5a), C6(H6)
2.d Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C17(H17a,H17b,H17c)
2.e Idealised tetrahedral OH refined as rotating group:
 O5(H5)
2.f :
 C15(H15)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z
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_refinement_flags_posn
O1 O -0.0508(4) 0.1317(7) 0.72412(16) 0.0168(8) Uani 1.000000 .
O2 O 0.0552(4) 0.2392(10) 0.61283(18) 0.0309(10) Uani 1.000000 .
O3 O 0.3292(4) 0.4768(8) 0.75188(18) 0.0233(9) Uani 1.000000 .
O4 O -0.0483(4) 0.2311(8) 0.87409(17) 0.0215(8) Uani 1.000000 .
O5 O 0.1868(4) 0.5910(7) 0.88996(18) 0.0221(8) Uani 1.000000 .
H5 H 0.2666(7) 0.684(4) 0.902(3) 0.0331(12) Uiso 1.000000 GR
O6 O 0.4909(4) 0.5292(8) 0.8502(2) 0.0268(9) Uani 1.000000 .
C1 C -0.4670(7) -0.1463(13) 0.6182(3) 0.0328(14) Uani 1.000000 .
H1 H -0.5720(7) -0.1533(13) 0.6369(3) 0.0394(17) Uiso 1.000000 R
C2 C -0.3570(6) 0.0303(13) 0.6463(3) 0.0292(13) Uani 1.000000 .
H2 H -0.3863(6) 0.1444(13) 0.6844(3) 0.0350(15) Uiso 1.000000 R
C3 C -0.2031(6) 0.0435(11) 0.6195(2) 0.0195(11) Uani 1.000000 .
C4 C -0.1635(6) -0.1223(11) 0.5629(3) 0.0213(11) Uani 1.000000 .
H4 H -0.0596(6) -0.1123(11) 0.5433(3) 0.0256(13) Uiso 1.000000 R
C5 C -0.4258(6) -0.3142(12) 0.5630(3) 0.0276(12) Uani 1.000000 .
H5a H -0.5016(6) -0.4383(12) 0.5442(3) 0.0331(14) Uiso 1.000000 R
C6 C -0.2736(6) -0.3008(11) 0.5351(3) 0.0234(11) Uani 1.000000 .
H6 H -0.2451(6) -0.4145(11) 0.4968(3) 0.0281(13) Uiso 1.000000 R
C7 C -0.0840(6) 0.2329(12) 0.6538(2) 0.0210(11) Uani 1.000000 .
H7 H -0.1314(6) 0.4159(12) 0.6568(2) 0.0252(13) Uiso 1.000000 R
C8 C 0.1733(6) 0.4108(13) 0.6437(3) 0.0288(15) Uani 1.000000 .
H8a H 0.2706(6) 0.4110(13) 0.6143(3) 0.0346(18) Uiso 1.000000 R
H8b H 0.1319(6) 0.5958(13) 0.6462(3) 0.0346(18) Uiso 1.000000 R
C9 C 0.2134(6) 0.3087(11) 0.7183(3) 0.0196(11) Uani 1.000000 .
H9 H 0.2578(6) 0.1237(11) 0.7149(3) 0.0235(14) Uiso 1.000000 R
C10 C 0.0624(6) 0.3014(10) 0.7607(2) 0.0157(10) Uani 1.000000 .
H10 H 0.0173(6) 0.4859(10) 0.7641(2) 0.0188(12) Uiso 1.000000 R
C11 C 0.3792(6) 0.3595(11) 0.8180(3) 0.0204(11) Uani 1.000000 .
H11 H 0.4278(6) 0.1799(11) 0.8096(3) 0.0245(13) Uiso 1.000000 R
C12 C 0.0918(5) 0.1911(10) 0.8351(2) 0.0151(10) Uani 1.000000 .
H12 H 0.1148(5) -0.0045(10) 0.8320(2) 0.0182(12) Uiso 1.000000 R
C13 C 0.2380(6) 0.3361(10) 0.8699(3) 0.0181(11) Uani 1.000000 .
C14 C 0.2985(6) 0.1845(11) 0.9335(3) 0.0213(11) Uani 1.000000 .
C15 C 0.3569(7) 0.0774(12) 0.9851(3) 0.0313(13) Uani 1.000000 .
H15 H 0.4031(7) -0.0073(12) 1.0259(3) 0.0376(16) Uiso 1.000000 R
C16 C -0.0833(7) 0.0428(12) 0.9278(3) 0.0291(12) Uani 1.000000 .
H16a H -0.061(5) -0.1375(14) 0.9104(8) 0.0437(19) Uiso 1.000000 GR
H16b H -0.017(4) 0.079(5) 0.9703(8) 0.0437(19) Uiso 1.000000 GR
H16c H -0.1966(14) 0.056(6) 0.9400(17) 0.0437(19) Uiso 1.000000 GR
C17 C 0.6380(6) 0.5506(17) 0.8128(3) 0.0394(16) Uani 1.000000 .
H17a H 0.692(3) 0.377(3) 0.813(2) 0.059(2) Uiso 1.000000 GR
H17b H 0.6155(8) 0.606(10) 0.7635(9) 0.059(2) Uiso 1.000000 GR
H17c H 0.707(3) 0.683(8) 0.8363(17) 0.059(2) Uiso 1.000000 GR
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03376 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
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
C10 O1 C7 110.2(4) . . ?
C8 O2 C7 111.4(4) . . ?
C11 O3 C9 109.1(4) . . ?
C16 O4 C12 117.4(4) . . ?
C13 O5 H5 109.5 . . ?
C17 O6 C11 114.0(4) . . ?
C2 C1 H1 119.8(3) . . ?
C5 C1 H1 119.8(3) . . ?
C5 C1 C2 120.3(5) . . ?
H2 C2 C1 119.7(3) . . ?
C3 C2 C1 120.5(5) . . ?
C3 C2 H2 119.7(3) . . ?
C4 C3 C2 118.8(5) . . ?
C7 C3 C2 118.8(4) . . ?
C7 C3 C4 122.4(4) . . ?
H4 C4 C3 119.7(3) . . ?
C6 C4 C3 120.6(5) . . ?
C6 C4 H4 119.7(3) . . ?
H5a C5 C1 120.1(3) . . ?
C6 C5 C1 119.7(5) . . ?
C6 C5 H5a 120.1(3) . . ?
C5 C6 C4 119.9(5) . . ?
H6 C6 C4 120.0(3) . . ?
H6 C6 C5 120.0(3) . . ?
O2 C7 O1 111.2(4) . . ?
C3 C7 O1 106.6(4) . . ?
C3 C7 O2 109.0(4) . . ?
H7 C7 O1 110.0(3) . . ?
H7 C7 O2 110.0(3) . . ?
H7 C7 C3 110.0(3) . . ?
H8a C8 O2 110.1(3) . . ?
H8b C8 O2 110.1(4) . . ?
H8b C8 H8a 108.4 . . ?
C9 C8 O2 108.1(4) . . ?
C9 C8 H8a 110.1(3) . . ?
C9 C8 H8b 110.1(3) . . ?
C8 C9 O3 110.2(4) . . ?
H9 C9 O3 109.1(3) . . ?
H9 C9 C8 109.1(3) . . ?
C10 C9 O3 110.6(4) . . ?
C10 C9 C8 108.7(4) . . ?
C10 C9 H9 109.1(3) . . ?
C9 C10 O1 108.3(4) . . ?
H10 C10 O1 109.4(2) . . ?
H10 C10 C9 109.4(3) . . ?
C12 C10 O1 108.6(4) . . ?
C12 C10 C9 111.8(4) . . ?
C12 C10 H10 109.4(3) . . ?
O6 C11 O3 108.0(4) . . ?
H11 C11 O3 110.3(3) . . ?
H11 C11 O6 110.3(3) . . ?
C13 C11 O3 111.3(4) . . ?
C13 C11 O6 106.5(4) . . ?
C13 C11 H11 110.3(3) . . ?
C10 C12 O4 107.7(3) . . ?
H12 C12 O4 109.4(3) . . ?
H12 C12 C10 109.4(3) . . ?
C13 C12 O4 111.7(4) . . ?
C13 C12 C10 109.3(4) . . ?
C13 C12 H12 109.4(3) . . ?
C11 C13 O5 109.9(4) . . ?
C12 C13 O5 107.3(4) . . ?
C12 C13 C11 111.8(4) . . ?
C14 C13 O5 110.5(4) . . ?
C14 C13 C11 106.9(4) . . ?
C14 C13 C12 110.5(4) . . ?
C15 C14 C13 174.7(6) . . ?
H15 C15 C14 180.0 . . ?
H16a C16 O4 109.5 . . ?
H16b C16 O4 109.5 . . ?
H16b C16 H16a 109.5 . . ?
H16c C16 O4 109.5 . . ?
H16c C16 H16a 109.5 . . ?
H16c C16 H16b 109.5 . . ?
H17a C17 O6 109.5 . . ?
H17b C17 O6 109.5 . . ?
H17b C17 H17a 109.5 . . ?
H17c C17 O6 109.5 . . ?
H17c C17 H17a 109.5 . . ?
H17c C17 H17b 109.5 . . ?
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 C7 1.435(5) . ?
O1 C10 1.435(5) . ?
O2 C7 1.405(6) . ?
O2 C8 1.424(6) . ?
O3 C9 1.421(6) . ?
O3 C11 1.428(6) . ?
O4 C12 1.406(5) . ?
O4 C16 1.414(6) . ?
O5 H5 0.8400 . ?
O5 C13 1.399(6) . ?
O6 C11 1.391(6) . ?
O6 C17 1.430(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.373(8) . ?
C1 C5 1.383(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(7) . ?
C3 C4 1.391(7) . ?
C3 C7 1.510(7) . ?
C4 H4 0.9500 . ?
C4 C6 1.378(7) . ?
C5 H5a 0.9500 . ?
C5 C6 1.384(7) . ?
C6 H6 0.9500 . ?
C7 H7 1.0000 . ?
C8 H8a 0.9900 . ?
C8 H8b 0.9900 . ?
C8 C9 1.521(7) . ?
C9 H9 1.0000 . ?
C9 C10 1.503(6) . ?
C10 H10 1.0000 . ?
C10 C12 1.517(6) . ?
C11 H11 1.0000 . ?
C11 C13 1.547(7) . ?
C12 H12 1.0000 . ?
C12 C13 1.554(6) . ?
C13 C14 1.494(7) . ?
C14 C15 1.202(8) . ?
C15 H15 0.9500 . ?
C16 H16a 0.9800 . ?
C16 H16b 0.9800 . ?
C16 H16c 0.9800 . ?
C17 H17a 0.9800 . ?
C17 H17b 0.9800 . ?
C17 H17c 0.9800 . ?
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 O2 C8 -61.5(5) . . . . ?
O1 C7 C3 C2 67.5(5) . . . . ?
O1 C7 C3 C4 -111.2(4) . . . . ?
O1 C10 C9 O3 179.4(3) . . . . ?
O1 C10 C9 C8 58.3(4) . . . . ?
O1 C10 C12 O4 -69.9(4) . . . . ?
O1 C10 C12 C13 168.6(4) . . . . ?
O2 C7 C3 C2 -172.4(4) . . . . ?
O2 C7 C3 C4 9.0(5) . . . . ?
O2 C8 C9 O3 -179.0(4) . . . . ?
O2 C8 C9 C10 -57.7(5) . . . . ?
O3 C9 C10 C12 -61.1(4) . . . . ?
O3 C11 O6 C17 -66.7(5) . . . . ?
O3 C11 C13 O5 -66.3(4) . . . . ?
O3 C11 C13 C12 52.8(5) . . . . ?
O3 C11 C13 C14 173.8(4) . . . . ?
O4 C12 C10 C9 170.8(4) . . . . ?
O4 C12 C13 O5 -43.7(4) . . . . ?
O4 C12 C13 C11 -164.3(4) . . . . ?
O4 C12 C13 C14 76.7(4) . . . . ?
O5 C13 C11 O6 51.2(4) . . . . ?
O5 C13 C12 C10 75.3(4) . . . . ?
O6 C11 C13 C12 170.3(4) . . . . ?
O6 C11 C13 C14 -68.7(5) . . . . ?
C1 C2 C3 C4 1.1(7) . . . . ?
C1 C2 C3 C7 -177.6(6) . . . . ?
C1 C5 C6 C4 0.6(7) . . . . ?
C2 C3 C4 C6 -1.5(6) . . . . ?
C3 C4 C6 C5 0.7(6) . . . . ?
C8 C9 C10 C12 177.8(4) . . . . ?
C9 C10 C12 C13 49.3(4) . . . . ?
C10 C12 C13 C11 -45.2(4) . . . . ?
C10 C12 C13 C14 -164.2(4) . . . . ?
