#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:51:35 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284311 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/93/7159321.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_7159321
loop_
_publ_author_name
'Ojo, O. Stephen'
'Hughes, David L.'
'Richards, Christopher J.'
_publ_section_title
;
 An expedient copper-catalysed asymmetric synthesis of γ-lactones
 and γ-lactams. Application to the synthesis of lucidulactone A.
;
_journal_issue                   19
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4144
_journal_page_last               4149
_journal_paper_doi               10.1039/d3ob00563a
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H12 O3'
_chemical_formula_structural     4-MeO-C6H4-cyclo-(CHCH2OC(O)CH2)
_chemical_formula_sum            'C11 H12 O3'
_chemical_formula_weight         192.21
_chemical_name_systematic        (R)-6d
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-11-09 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.874(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.0003(5)
_cell_length_b                   7.5875(3)
_cell_length_c                   9.1343(7)
_cell_measurement_reflns_used    6495
_cell_measurement_temperature    102(4)
_cell_measurement_theta_max      76.0720
_cell_measurement_theta_min      5.0140
_cell_volume                     464.28(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976 and Farrugia, 2012)'
_computing_publication_material
'SHELXL-2018/3 (Sheldrick, 2015b) and WINGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8875
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.479
_diffrn_reflns_theta_max         67.479
_diffrn_reflns_theta_min         5.060
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82509
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       plate
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.304
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.049
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 722 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1650
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0418
_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)+(0.0747P)²+0.0981P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_full    0.976
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                1630
_reflns_number_total             1650
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00563a2.cif
_cod_data_source_block           stepheno11a
_cod_depositor_comments
'Adding full bibliography for 7159321--7159322.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7159321
_shelx_shelxl_version_number     2018/3
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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_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 0.3440(4) 0.5444(4) 0.3386(3) 0.0320(7) Uani 1 1 d . . . . .
C2 C 0.4485(4) 0.4597(4) 0.4750(3) 0.0293(6) Uani 1 1 d . . . A 1
H2 H 0.561500 0.393792 0.477737 0.035 Uiso 1 1 calc R U . A 1
C3 C 0.3868(4) 0.4722(3) 0.6056(3) 0.0296(6) Uani 1 1 d . . . A 1
H3 H 0.460358 0.418096 0.695751 0.035 Uiso 1 1 calc R U . A 1
C4 C 0.2139(4) 0.5663(3) 0.6016(3) 0.0287(6) Uani 1 1 d . . . A 1
O4 O 0.1632(3) 0.5672(3) 0.7350(2) 0.0383(6) Uani 1 1 d . . . A 1
C41 C -0.0260(5) 0.6387(5) 0.7317(4) 0.0385(8) Uani 1 1 d . . . A 1
H41A H -0.026915 0.762976 0.711647 0.058 Uiso 1 1 calc R U . A 1
H41B H -0.049994 0.619351 0.828723 0.058 Uiso 1 1 calc R U . A 1
H41C H -0.128573 0.582128 0.652567 0.058 Uiso 1 1 calc R U . A 1
C5 C 0.1083(4) 0.6496(3) 0.4674(4) 0.0311(7) Uani 1 1 d . . . A 1
H5 H -0.006903 0.712533 0.464064 0.037 Uiso 1 1 calc R U . A 1
C6 C 0.1741(4) 0.6395(4) 0.3379(4) 0.0331(7) Uani 1 1 d . . . A 1
H6 H 0.103028 0.697486 0.249062 0.040 Uiso 1 1 calc R U . A 1
C7 C 0.4068(4) 0.5363(4) 0.1934(4) 0.0277(8) Uani 0.900(8) 1 d . . P A 1
H7 H 0.345725 0.635013 0.127082 0.033 Uiso 0.900(8) 1 calc R U P A 1
C8 C 0.3460(5) 0.3627(5) 0.1048(4) 0.0302(9) Uani 0.900(8) 1 d . . P A 1
H8A H 0.362864 0.263668 0.174513 0.036 Uiso 0.900(8) 1 calc R U P A 1
H8B H 0.207922 0.367184 0.042368 0.036 Uiso 0.900(8) 1 calc R U P A 1
O9 O 0.4797(3) 0.3476(4) 0.0094(3) 0.0324(7) Uani 0.900(8) 1 d . . P A 1
C10 C 0.6462(4) 0.4459(4) 0.0685(3) 0.0278(6) Uani 1 1 d . . . . .
O10 O 0.7798(3) 0.4477(3) 0.0097(2) 0.0364(5) Uani 1 1 d . . . . .
C11A C 0.6328(4) 0.5347(4) 0.2123(3) 0.0322(6) Uani 0.900(8) 1 d . . P A 1
H11A H 0.685987 0.653477 0.220066 0.039 Uiso 0.900(8) 1 calc R U P A 1
H11B H 0.704453 0.468371 0.302278 0.039 Uiso 0.900(8) 1 calc R U P A 1
C11B C 0.6328(4) 0.5347(4) 0.2123(3) 0.0322(6) Uani 0.100(8) 1 d . . P A 2
H11C H 0.602918 0.659444 0.198409 0.039 Uiso 0.100(8) 1 calc R U P A 2
H11D H 0.750685 0.516221 0.298259 0.039 Uiso 0.100(8) 1 calc R U P A 2
C21 C 0.438(4) 0.416(4) 0.224(3) 0.023(7) Uiso 0.100(8) 1 d . . P A 2
H21 H 0.461460 0.290935 0.251299 0.027 Uiso 0.100(8) 1 calc R U P A 2
C22 C 0.319(4) 0.459(5) 0.062(3) 0.024(7) Uiso 0.100(8) 1 d . . P A 2
H22A H 0.205686 0.380977 0.026897 0.029 Uiso 0.100(8) 1 calc R U P A 2
H22B H 0.272208 0.580184 0.054493 0.029 Uiso 0.100(8) 1 calc R U P A 2
O23 O 0.462(3) 0.433(4) -0.024(2) 0.024(5) Uiso 0.100(8) 1 d . . P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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
C6 C1 C2 117.8(3) . . ?
C6 C1 C7 118.8(3) . . ?
C2 C1 C7 123.4(2) . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
O4 C4 C5 125.2(2) . . ?
O4 C4 C3 115.3(3) . . ?
C5 C4 C3 119.5(3) . . ?
C4 O4 C41 117.7(2) . . ?
O4 C41 H41A 109.5 . . ?
O4 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O4 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 121.2(3) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C1 C7 C8 112.9(2) . . ?
C1 C7 C11A 116.8(2) . . ?
C8 C7 C11A 99.8(2) . . ?
C1 C7 H7 109.0 . . ?
C8 C7 H7 109.0 . . ?
C11A C7 H7 109.0 . . ?
O9 C8 C7 104.8(2) . . ?
O9 C8 H8A 110.8 . . ?
C7 C8 H8A 110.8 . . ?
O9 C8 H8B 110.8 . . ?
C7 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C10 O9 C8 110.2(2) . . ?
O10 C10 O23 117.0(9) . . ?
O10 C10 O9 121.1(3) . . ?
O10 C10 C11A 129.6(3) . . ?
O9 C10 C11A 109.2(2) . . ?
O10 C10 C11B 129.6(3) . . ?
O23 C10 C11B 107.2(9) . . ?
C10 C11A C7 103.2(2) . . ?
C10 C11A H11A 111.1 . . ?
C7 C11A H11A 111.1 . . ?
C10 C11A H11B 111.1 . . ?
C7 C11A H11B 111.1 . . ?
H11A C11A H11B 109.1 . . ?
C10 C11B C21 94.2(9) . . ?
C10 C11B H11C 112.9 . . ?
C21 C11B H11C 112.9 . . ?
C10 C11B H11D 112.9 . . ?
C21 C11B H11D 112.9 . . ?
H11C C11B H11D 110.3 . . ?
C22 C21 C11B 92.7(17) . . ?
C22 C21 C1 106(2) . . ?
C11B C21 C1 101.5(14) . . ?
C22 C21 H21 117.6 . . ?
C11B C21 H21 117.6 . . ?
C1 C21 H21 117.6 . . ?
O23 C22 C21 103(2) . . ?
O23 C22 H22A 111.1 . . ?
C21 C22 H22A 111.1 . . ?
O23 C22 H22B 111.1 . . ?
C21 C22 H22B 111.1 . . ?
H22A C22 H22B 109.1 . . ?
C10 O23 C22 109.8(17) . . ?
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 C6 1.390(4) . ?
C1 C2 1.404(4) . ?
C1 C7 1.515(4) . ?
C1 C21 1.70(3) . ?
C2 C3 1.385(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(4) . ?
C3 H3 0.9300 . ?
C4 O4 1.365(3) . ?
C4 C5 1.386(4) . ?
O4 C41 1.423(3) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.540(4) . ?
C7 C11A 1.541(4) . ?
C7 H7 0.9800 . ?
C8 O9 1.456(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
O9 C10 1.357(4) . ?
C10 O10 1.206(3) . ?
C10 O23 1.32(2) . ?
C10 C11A 1.503(4) . ?
C10 C11B 1.503(4) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C11B C21 1.66(2) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C21 C22 1.51(4) . ?
C21 H21 0.9800 . ?
C22 O23 1.46(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
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
C6 C1 C2 C3 -1.0(4) . . . . ?
C7 C1 C2 C3 179.3(3) . . . . ?
C1 C2 C3 C4 2.0(4) . . . . ?
C2 C3 C4 O4 178.5(2) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C5 C4 O4 C41 8.9(4) . . . . ?
C3 C4 O4 C41 -171.1(2) . . . . ?
O4 C4 C5 C6 -179.9(2) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C2 C1 C6 C5 -0.5(4) . . . . ?
C7 C1 C6 C5 179.2(2) . . . . ?
C4 C5 C6 C1 1.0(4) . . . . ?
C6 C1 C7 C8 -100.6(3) . . . . ?
C2 C1 C7 C8 79.1(3) . . . . ?
C6 C1 C7 C11A 144.5(3) . . . . ?
C2 C1 C7 C11A -35.8(4) . . . . ?
C1 C7 C8 O9 -158.3(2) . . . . ?
C11A C7 C8 O9 -33.6(3) . . . . ?
C7 C8 O9 C10 21.9(3) . . . . ?
C8 O9 C10 O10 177.6(3) . . . . ?
C8 O9 C10 C11A 0.3(4) . . . . ?
O10 C10 C11A C7 160.7(3) . . . . ?
O9 C10 C11A C7 -22.3(3) . . . . ?
C1 C7 C11A C10 155.1(2) . . . . ?
C8 C7 C11A C10 33.1(3) . . . . ?
O10 C10 C11B C21 -165.2(10) . . . . ?
O23 C10 C11B C21 44.2(17) . . . . ?
C10 C11B C21 C22 -52.7(17) . . . . ?
C10 C11B C21 C1 -159.5(10) . . . . ?
C11B C21 C22 O23 46(2) . . . . ?
C1 C21 C22 O23 148.8(18) . . . . ?
O10 C10 O23 C22 -171.5(16) . . . . ?
C11B C10 O23 C22 -17(2) . . . . ?
C21 C22 O23 C10 -22(3) . . . . ?
