#------------------------------------------------------------------------------
#$Date: 2022-03-06 03:35:56 +0200 (Sun, 06 Mar 2022) $
#$Revision: 273466 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158553.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_7158553
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         'C7 H10 O4'
_chemical_formula_sum            'C7 H10 O4'
_chemical_formula_weight         158.15
_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                100.249(11)
_cell_angle_beta                 91.298(12)
_cell_angle_gamma                98.547(11)
_cell_formula_units_Z            2
_cell_length_a                   5.2698(10)
_cell_length_b                   7.5782(14)
_cell_length_c                   10.1856(19)
_cell_measurement_reflns_used    1527
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      24.66
_cell_measurement_theta_min      2.76
_cell_volume                     395.33(13)
_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 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.3871
_diffrn_reflns_av_unetI/netI     0.2992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            16345
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         30.594
_diffrn_reflns_theta_min         2.034
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  0.9461
_exptl_absorpt_correction_T_min  0.8803
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker APEX3'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       plate
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.956
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     103
_refine_ls_number_reflns         2434
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.956
_refine_ls_R_factor_all          0.2441
_refine_ls_R_factor_gt           0.0878
_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)+(0.0601P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1658
_reflns_Friedel_coverage         0.000
_reflns_number_gt                983
_reflns_number_total             2434
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00047d2.cif
_cod_data_source_block           mo_v468GuillotICMMO
_cod_database_code               7158553
_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   0.991
_shelx_estimated_absorpt_t_max   0.997
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 0.2952(5) 0.6234(4) 0.9301(3) 0.0147(7) Uani 1 1 d . . . . .
C2 C 0.5240(5) 0.7177(4) 0.8747(3) 0.0149(7) Uani 1 1 d . . . . .
C3 C 0.5352(5) 0.6721(4) 0.7251(3) 0.0173(7) Uani 1 1 d . . . . .
H3A H 0.522283 0.538900 0.697270 0.021 Uiso 1 1 calc R U . . .
H3B H 0.703272 0.728575 0.698491 0.021 Uiso 1 1 calc R U . . .
C4 C 0.3233(5) 0.7367(4) 0.6536(3) 0.0160(7) Uani 1 1 d . . . . .
C5 C 0.7022(6) 0.8315(4) 0.9525(3) 0.0242(8) Uani 1 1 d . . . . .
H5A H 0.685942 0.854810 1.046423 0.029 Uiso 1 1 calc R U . . .
H5B H 0.846959 0.890227 0.914583 0.029 Uiso 1 1 calc R U . . .
C6 C 0.1146(6) 0.7118(4) 0.4386(3) 0.0210(7) Uani 1 1 d . . . . .
H6A H -0.036659 0.734362 0.491272 0.025 Uiso 1 1 calc R U . . .
H6B H 0.058562 0.609661 0.363706 0.025 Uiso 1 1 calc R U . . .
C7 C 0.2164(6) 0.8787(4) 0.3838(3) 0.0267(8) Uani 1 1 d . . . . .
H7A H 0.370614 0.858407 0.334960 0.040 Uiso 1 1 calc R U . . .
H7B H 0.259703 0.982113 0.457644 0.040 Uiso 1 1 calc R U . . .
H7C H 0.085185 0.904448 0.323264 0.040 Uiso 1 1 calc R U . . .
O1 O 0.2735(4) 0.6749(3) 1.06021(18) 0.0230(6) Uani 1 1 d . . . . .
H1 H 0.112(6) 0.615(4) 1.0862(10) 0.035 Uiso 1 1 calc R U . . .
O2 O 0.1426(4) 0.5056(3) 0.85999(18) 0.0206(5) Uani 1 1 d . . . . .
O3 O 0.1849(4) 0.8393(3) 0.70494(19) 0.0217(5) Uani 1 1 d . . . . .
O4 O 0.3094(4) 0.6630(3) 0.52290(18) 0.0207(5) 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
O2 C1 O1 123.4(2) . . ?
O2 C1 C2 121.6(2) . . ?
O1 C1 C2 115.0(2) . . ?
C5 C2 C1 121.6(3) . . ?
C5 C2 C3 123.5(2) . . ?
C1 C2 C3 114.9(2) . . ?
C2 C3 C4 112.3(2) . . ?
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 124.4(3) . . ?
O3 C4 C3 125.5(3) . . ?
O4 C4 C3 110.1(2) . . ?
C2 C5 H5A 120.0 . . ?
C2 C5 H5B 120.0 . . ?
H5A C5 H5B 120.0 . . ?
O4 C6 C7 111.1(2) . . ?
O4 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
O4 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C1 O1 H1 109.5 . . ?
C4 O4 C6 117.4(2) . . ?
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 O2 1.219(3) . ?
C1 O1 1.325(3) . ?
C1 C2 1.484(4) . ?
C2 C5 1.317(4) . ?
C2 C3 1.506(4) . ?
C3 C4 1.507(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 O3 1.204(3) . ?
C4 O4 1.345(3) . ?
C5 H5A 0.9500 . ?
C5 H5B 0.9500 . ?
C6 O4 1.454(3) . ?
C6 C7 1.504(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
O1 H1 0.97(3) . ?
