#------------------------------------------------------------------------------
#$Date: 2025-08-22 00:24:23 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301857 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/43/7114330.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_7114330
loop_
_publ_author_name
'Lorbach, Volker'
'Franke, Dirk'
'Nieger, Martin'
'MÃ¼ller, Michael'
_publ_section_title
;
 Cyclohexadiene-trans-diols as versatile starting material in natural
 product synthesis: short and efficient synthesis of iso-crotepoxide and
 ent-senepoxide
;
_journal_issue                   5
_journal_name_full               'Chemical Communications'
_journal_page_first              494
_journal_paper_doi               10.1039/b110420a
_journal_year                    2002
_chemical_formula_moiety         'C14 H14 O6'
_chemical_formula_sum            'C14 H14 O6'
_chemical_formula_weight         278.25
_chemical_name_systematic
; 
Benzoic acid 5,6-dihydroxy-3,8-dioxa-tricyclo[5.1.0.0^2,4^]oct-4-
ylmethyl ester
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8867(2)
_cell_length_b                   11.7119(2)
_cell_length_c                   12.0177(3)
_cell_measurement_reflns_used    5616
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1
_cell_volume                     1250.80(5)
_computing_cell_refinement       DENZO-SMN
_computing_data_collection       Collect
_computing_data_reduction        DENZO-SMN
_computing_molecular_graphics    XP
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'rotation in phi and omega, 2 deg.'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            24670
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.34
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   '-0.1(6); cannot be determined reliabl.'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2206
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0221
_refine_ls_R_factor_gt           0.0214
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0362P)²+0.1548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0559
_refine_ls_wR_factor_ref         0.0563
_reflns_number_gt                2157
_reflns_number_total             2206
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b110420a.txt
_cod_data_source_block           mm02_compound_14
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7114330
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.83674(10) 0.53788(7) 0.40866(7) 0.02418(19) Uani 1 1 d D
H1O H 0.8748(16) 0.5341(13) 0.3454(12) 0.036 Uiso 1 1 d D
O2 O 0.45831(9) 0.43413(7) 0.33310(7) 0.02210(19) Uani 1 1 d D
H2O H 0.4147(15) 0.4973(11) 0.3327(13) 0.033 Uiso 1 1 d D
O3 O 0.79645(9) 0.51757(7) 0.17420(7) 0.02173(18) Uani 1 1 d .
O4 O 0.49471(9) 0.67477(6) 0.29542(6) 0.02004(18) Uani 1 1 d .
O5 O 0.62411(9) 0.74833(7) 0.52901(6) 0.02131(18) Uani 1 1 d .
O6 O 0.73195(10) 0.91447(7) 0.57665(7) 0.0268(2) Uani 1 1 d .
C1 C 0.67703(13) 0.54589(9) 0.39426(9) 0.0183(2) Uani 1 1 d .
H1 H 0.6291 0.5388 0.4692 0.022 Uiso 1 1 calc R
C2 C 0.61695(13) 0.44882(9) 0.32097(9) 0.0193(2) Uani 1 1 d .
H2 H 0.6666 0.3765 0.3456 0.023 Uiso 1 1 calc R
C3 C 0.65261(13) 0.46545(9) 0.19889(9) 0.0199(2) Uani 1 1 d .
H3 H 0.6185 0.4037 0.1472 0.024 Uiso 1 1 calc R
C4 C 0.65846(13) 0.58128(9) 0.15284(9) 0.0201(2) Uani 1 1 d .
H4 H 0.6280 0.5905 0.0732 0.024 Uiso 1 1 calc R
C5 C 0.63131(13) 0.68014(9) 0.22786(9) 0.0191(2) Uani 1 1 d .
H5 H 0.6603 0.7570 0.1988 0.023 Uiso 1 1 calc R
C6 C 0.64044(11) 0.66411(9) 0.34894(9) 0.0164(2) Uani 1 1 d .
C7 C 0.68682(14) 0.76411(10) 0.41840(9) 0.0205(2) Uani 1 1 d .
H7A H 0.7979 0.7687 0.4224 0.025 Uiso 1 1 calc R
H7B H 0.6485 0.8358 0.3852 0.025 Uiso 1 1 calc R
C8 C 0.66176(12) 0.82996(9) 0.60230(9) 0.0193(2) Uani 1 1 d .
C9 C 0.60861(13) 0.80457(10) 0.71736(10) 0.0216(2) Uani 1 1 d .
C10 C 0.52105(13) 0.70875(10) 0.74156(10) 0.0223(3) Uani 1 1 d .
H10 H 0.4963 0.6558 0.6845 0.027 Uiso 1 1 calc R
C11 C 0.47017(14) 0.69133(11) 0.84993(11) 0.0286(3) Uani 1 1 d .
H11 H 0.4093 0.6270 0.8669 0.034 Uiso 1 1 calc R
C12 C 0.50875(16) 0.76845(12) 0.93306(10) 0.0327(3) Uani 1 1 d .
H12 H 0.4727 0.7569 1.0066 0.039 Uiso 1 1 calc R
C13 C 0.59908(16) 0.86200(12) 0.91001(11) 0.0333(3) Uani 1 1 d .
H13 H 0.6273 0.9131 0.9678 0.040 Uiso 1 1 calc R
C14 C 0.64800(14) 0.88043(11) 0.80181(10) 0.0279(3) Uani 1 1 d .
H14 H 0.7086 0.9450 0.7852 0.033 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 H1O 107.2(11)
C2 O2 H2O 110.5(10)
C3 O3 C4 60.60(7)
C6 O4 C5 60.59(7)
C8 O5 C7 114.46(8)
O1 C1 C6 108.31(9)
O1 C1 C2 111.45(9)
C6 C1 C2 113.21(9)
O1 C1 H1 107.9
C6 C1 H1 107.9
C2 C1 H1 107.9
O2 C2 C3 108.74(9)
O2 C2 C1 111.99(9)
C3 C2 C1 112.85(9)
O2 C2 H2 107.7
C3 C2 H2 107.7
C1 C2 H2 107.7
O3 C3 C4 60.07(7)
O3 C3 C2 115.97(9)
C4 C3 C2 119.50(9)
O3 C3 H3 116.4
C4 C3 H3 116.4
C2 C3 H3 116.4
O3 C4 C3 59.33(7)
O3 C4 C5 115.35(9)
C3 C4 C5 119.07(9)
O3 C4 H4 116.8
C3 C4 H4 116.8
C5 C4 H4 116.8
O4 C5 C6 59.36(7)
O4 C5 C4 115.97(9)
C6 C5 C4 119.46(10)
O4 C5 H5 116.6
C6 C5 H5 116.6
C4 C5 H5 116.6
O4 C6 C5 60.06(7)
O4 C6 C7 115.20(9)
C5 C6 C7 117.88(9)
O4 C6 C1 115.29(9)
C5 C6 C1 118.82(9)
C7 C6 C1 116.96(9)
O5 C7 C6 107.76(8)
O5 C7 H7A 110.2
C6 C7 H7A 110.2
O5 C7 H7B 110.2
C6 C7 H7B 110.2
H7A C7 H7B 108.5
O6 C8 O5 122.95(10)
O6 C8 C9 124.25(10)
O5 C8 C9 112.80(10)
C14 C9 C10 120.05(11)
C14 C9 C8 117.95(11)
C10 C9 C8 122.00(10)
C11 C10 C9 119.55(11)
C11 C10 H10 120.2
C9 C10 H10 120.2
C12 C11 C10 119.77(12)
C12 C11 H11 120.1
C10 C11 H11 120.1
C13 C12 C11 120.86(11)
C13 C12 H12 119.6
C11 C12 H12 119.6
C12 C13 C14 119.44(12)
C12 C13 H13 120.3
C14 C13 H13 120.3
C13 C14 C9 120.30(13)
C13 C14 H14 119.8
C9 C14 H14 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.4329(14)
O1 H1O 0.834(13)
O2 C2 1.4277(14)
O2 H2O 0.836(13)
O3 C3 1.4473(14)
O3 C4 1.4582(13)
O4 C6 1.4513(13)
O4 C5 1.4617(14)
O5 C8 1.3423(14)
O5 C7 1.4532(13)
O6 C8 1.2099(15)
C1 C6 1.5230(15)
C1 C2 1.5341(15)
C1 H1 1.0000
C2 C3 1.5135(15)
C2 H2 1.0000
C3 C4 1.4660(15)
C3 H3 1.0000
C4 C5 1.4872(16)
C4 H4 1.0000
C5 C6 1.4694(15)
C5 H5 1.0000
C6 C7 1.4962(15)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.4911(16)
C9 C14 1.3935(17)
C9 C10 1.3962(18)
C10 C11 1.3937(18)
C10 H10 0.9500
C11 C12 1.3898(19)
C11 H11 0.9500
C12 C13 1.386(2)
C12 H12 0.9500
C13 C14 1.3880(18)
C13 H13 0.9500
C14 H14 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O3 0.834(13) 2.180(15) 2.8502(12) 137.4(13) .
O2 H2O O4 0.836(13) 2.242(14) 2.8728(11) 132.4(13) .
O2 H2O O6 0.836(13) 2.211(14) 2.8926(12) 138.8(14) 4_466
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
O1 C1 C2 O2 162.03(9)
C6 C1 C2 O2 -75.57(11)
O1 C1 C2 C3 -74.87(11)
C6 C1 C2 C3 47.52(13)
C4 O3 C3 C2 -110.59(11)
O2 C2 C3 O3 160.64(9)
C1 C2 C3 O3 35.76(13)
O2 C2 C3 C4 91.87(12)
C1 C2 C3 C4 -33.01(15)
C3 O3 C4 C5 110.13(10)
C2 C3 C4 O3 104.76(11)
O3 C3 C4 C5 -103.87(11)
C2 C3 C4 C5 0.89(16)
C6 O4 C5 C4 110.32(11)
O3 C4 C5 O4 -118.77(10)
C3 C4 C5 O4 -51.26(14)
O3 C4 C5 C6 -50.86(14)
C3 C4 C5 C6 16.66(16)
C5 O4 C6 C7 108.99(10)
C5 O4 C6 C1 -110.07(10)
C4 C5 C6 O4 -104.47(11)
O4 C5 C6 C7 -104.55(10)
C4 C5 C6 C7 150.98(10)
O4 C5 C6 C1 104.23(10)
C4 C5 C6 C1 -0.24(15)
O1 C1 C6 O4 160.42(8)
C2 C1 C6 O4 36.30(12)
O1 C1 C6 C5 92.15(11)
C2 C1 C6 C5 -31.98(14)
O1 C1 C6 C7 -59.34(12)
C2 C1 C6 C7 176.54(9)
C8 O5 C7 C6 177.46(9)
O4 C6 C7 O5 86.29(10)
C5 C6 C7 O5 154.26(9)
C1 C6 C7 O5 -53.98(12)
C7 O5 C8 O6 5.64(15)
C7 O5 C8 C9 -174.07(9)
O6 C8 C9 C14 -3.01(17)
O5 C8 C9 C14 176.70(10)
O6 C8 C9 C10 176.52(11)
O5 C8 C9 C10 -3.78(15)
C14 C9 C10 C11 1.71(17)
C8 C9 C10 C11 -177.80(10)
C9 C10 C11 C12 -0.91(18)
C10 C11 C12 C13 -0.86(19)
C11 C12 C13 C14 1.82(19)
C12 C13 C14 C9 -1.00(19)
C10 C9 C14 C13 -0.76(18)
C8 C9 C14 C13 178.77(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11173486
