#------------------------------------------------------------------------------
#$Date: 2022-03-06 03:35:56 +0200 (Sun, 06 Mar 2022) $
#$Revision: 273466 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158555.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_7158555
loop_
_publ_author_name
'BRAIA, Nabila'
'Merabet-Khelassi, Mounia'
'TOFFANO, martial'
'Guillot, Régis'
'Aribi-Zouioueche, Louisa'
_publ_section_title
;
 Access to valuable building blocks by regio-and enantioselective
 ring-opening of itaconic anhydride using lipase catalysis.
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00047D
_journal_year                    2022
_chemical_formula_moiety         'C15 H26 O4'
_chemical_formula_sum            'C15 H26 O4'
_chemical_formula_weight         270.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-06-08 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                87.791(9)
_cell_angle_beta                 87.437(9)
_cell_angle_gamma                66.595(8)
_cell_formula_units_Z            2
_cell_length_a                   5.3029(14)
_cell_length_b                   5.4415(15)
_cell_length_c                   28.824(8)
_cell_measurement_reflns_used    2901
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      28.04
_cell_measurement_theta_min      2.83
_cell_volume                     762.3(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3134
_diffrn_reflns_av_unetI/netI     0.3721
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            24402
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.538
_diffrn_reflns_theta_min         2.830
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.9461
_exptl_absorpt_correction_T_min  0.7893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX3'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_description       needle
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         4654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.952
_refine_ls_R_factor_all          0.2800
_refine_ls_R_factor_gt           0.0945
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0361P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1471
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1863
_reflns_number_total             4654
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00047d2.cif
_cod_data_source_block           mo_v463GuillotICMMO
_cod_database_code               7158555
_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.
;
_shelx_estimated_absorpt_t_min   0.993
_shelx_estimated_absorpt_t_max   0.999
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_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
C1 C 0.2751(4) 0.5178(5) 0.45563(8) 0.0128(5) Uani 1 1 d . . . . .
C2 C 0.4920(4) 0.5312(4) 0.42229(8) 0.0111(5) Uani 1 1 d . . . . .
C3 C 0.4128(4) 0.7799(4) 0.39265(8) 0.0131(5) Uani 1 1 d . . . . .
H3A H 0.577838 0.780282 0.375219 0.016 Uiso 1 1 calc R U . . .
H3B H 0.343273 0.937804 0.412828 0.016 Uiso 1 1 calc R U . . .
C4 C 0.1955(4) 0.8034(5) 0.35876(8) 0.0127(5) Uani 1 1 d . . . . .
C5 C 0.7415(4) 0.3367(4) 0.42074(8) 0.0172(6) Uani 1 1 d . . . . .
H5A H 0.784377 0.185239 0.441142 0.021 Uiso 1 1 calc R U . . .
H5B H 0.877353 0.348760 0.399217 0.021 Uiso 1 1 calc R U . . .
C6 C -0.1017(4) 1.0822(4) 0.30231(8) 0.0176(6) Uani 1 1 d . . . . .
H6A H -0.266238 1.089877 0.320865 0.021 Uiso 1 1 calc R U . . .
H6B H -0.055918 0.938856 0.279345 0.021 Uiso 1 1 calc R U . . .
C7 C -0.1580(4) 1.3464(5) 0.27786(8) 0.0173(6) Uani 1 1 d . . . . .
H7A H 0.008921 1.336744 0.259844 0.021 Uiso 1 1 calc R U . . .
H7B H -0.200878 1.487266 0.301215 0.021 Uiso 1 1 calc R U . . .
C8 C -0.3966(4) 1.4223(5) 0.24527(8) 0.0193(6) Uani 1 1 d . . . . .
H8A H -0.352856 1.280829 0.222008 0.023 Uiso 1 1 calc R U . . .
H8B H -0.562565 1.430195 0.263389 0.023 Uiso 1 1 calc R U . . .
C9 C -0.4592(4) 1.6887(5) 0.22019(8) 0.0178(6) Uani 1 1 d . . . . .
H9A H -0.288839 1.685293 0.204163 0.021 Uiso 1 1 calc R U . . .
H9B H -0.516314 1.831583 0.243433 0.021 Uiso 1 1 calc R U . . .
C10 C -0.6823(4) 1.7585(5) 0.18483(8) 0.0196(6) Uani 1 1 d . . . . .
H10A H -0.852960 1.762760 0.200888 0.023 Uiso 1 1 calc R U . . .
H10B H -0.625672 1.615037 0.161686 0.023 Uiso 1 1 calc R U . . .
C11 C -0.7446(4) 2.0256(5) 0.15939(8) 0.0200(6) Uani 1 1 d . . . . .
H11A H -0.802158 2.169255 0.182493 0.024 Uiso 1 1 calc R U . . .
H11B H -0.573926 2.021686 0.143399 0.024 Uiso 1 1 calc R U . . .
C12 C -0.9675(4) 2.0941(5) 0.12387(8) 0.0218(6) Uani 1 1 d . . . . .
H12A H -0.908824 1.951617 0.100526 0.026 Uiso 1 1 calc R U . . .
H12B H -1.137449 2.095676 0.139777 0.026 Uiso 1 1 calc R U . . .
C13 C -1.0317(4) 2.3608(5) 0.09906(8) 0.0217(6) Uani 1 1 d . . . . .
H13A H -0.862001 2.358438 0.082930 0.026 Uiso 1 1 calc R U . . .
H13B H -1.088458 2.502895 0.122446 0.026 Uiso 1 1 calc R U . . .
C14 C -1.2560(4) 2.4314(5) 0.06386(9) 0.0277(7) Uani 1 1 d . . . . .
H14A H -1.424705 2.430021 0.079802 0.033 Uiso 1 1 calc R U . . .
H14B H -1.197517 2.291789 0.040006 0.033 Uiso 1 1 calc R U . . .
C15 C -1.3234(4) 2.7030(5) 0.03989(9) 0.0319(7) Uani 1 1 d . . . . .
H15A H -1.386524 2.843235 0.063155 0.048 Uiso 1 1 calc R U . . .
H15B H -1.468546 2.735799 0.017681 0.048 Uiso 1 1 calc R U . . .
H15C H -1.158526 2.704980 0.023396 0.048 Uiso 1 1 calc R U . . .
O1 O 0.0642(2) 0.7128(3) 0.46438(5) 0.0154(4) Uani 1 1 d . . . . .
O2 O 0.3345(2) 0.2782(3) 0.47533(5) 0.0167(4) Uani 1 1 d . . . . .
H2 H 0.205011 0.283300 0.493689 0.025 Uiso 1 1 calc R U . . .
O3 O 0.0926(3) 0.6428(3) 0.35559(5) 0.0199(4) Uani 1 1 d . . . . .
O4 O 0.1277(2) 1.0264(3) 0.33244(5) 0.0163(4) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0031 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 0.0109 0.0061 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 123.6(2) . . ?
O1 C1 C2 122.5(2) . . ?
O2 C1 C2 113.94(18) . . ?
C5 C2 C1 121.2(2) . . ?
C5 C2 C3 123.0(2) . . ?
C1 C2 C3 115.73(17) . . ?
C2 C3 C4 112.41(17) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
O3 C4 O4 123.6(2) . . ?
O3 C4 C3 124.8(2) . . ?
O4 C4 C3 111.64(18) . . ?
C2 C5 H5A 120.0 . . ?
C2 C5 H5B 120.0 . . ?
H5A C5 H5B 120.0 . . ?
O4 C6 C7 108.03(16) . . ?
O4 C6 H6A 110.1 . . ?
C7 C6 H6A 110.1 . . ?
O4 C6 H6B 110.1 . . ?
C7 C6 H6B 110.1 . . ?
H6A C6 H6B 108.4 . . ?
C6 C7 C8 111.89(17) . . ?
C6 C7 H7A 109.2 . . ?
C8 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 113.17(17) . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 114.00(17) . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
C10 C9 H9B 108.8 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 114.08(17) . . ?
C9 C10 H10A 108.7 . . ?
C11 C10 H10A 108.7 . . ?
C9 C10 H10B 108.7 . . ?
C11 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 113.88(17) . . ?
C12 C11 H11A 108.8 . . ?
C10 C11 H11A 108.8 . . ?
C12 C11 H11B 108.8 . . ?
C10 C11 H11B 108.8 . . ?
H11A C11 H11B 107.7 . . ?
C13 C12 C11 113.86(17) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 C14 114.10(18) . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 C15 113.64(19) . . ?
C13 C14 H14A 108.8 . . ?
C15 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C15 C14 H14B 108.8 . . ?
H14A C14 H14B 107.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 O2 H2 109.5 . . ?
C4 O4 C6 115.69(16) . . ?
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
C1 O1 1.222(2) . ?
C1 O2 1.325(3) . ?
C1 C2 1.488(3) . ?
C2 C5 1.326(3) . ?
C2 C3 1.493(3) . ?
C3 C4 1.507(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O3 1.208(2) . ?
C4 O4 1.336(3) . ?
C5 H5A 0.9500 . ?
C5 H5B 0.9500 . ?
C6 O4 1.452(2) . ?
C6 C7 1.501(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.521(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.514(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.518(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.523(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.521(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.511(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.518(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.521(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O2 H2 0.8400 . ?
