Crystal structure of (3R,3aS,6R,6aR)-6-hexyl-3-methyltetrahydrofuro[3,4-b]furan-2,4-dione, C13H20O4
Huang, Yu-Xi; Chen, Zan-Hong; Liao, Yu-Ting; Li, Jia-Yi; Huang, Mei-Ying; Ding, Bo; Huang, Hong-Bo; Tao, Yi-Wen; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 719–721; doi:10.1515/ncrs-2023-0167

data_8107540
_publ_section_title
;
 Crystal structure of
 (3R,3aS,6R,6aR)-6-hexyl-3-methyltetrahydrofuro[3,4-b]furan-2,4-dione,
 C13H20O4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              719
_journal_page_last               721
_journal_paper_doi               10.1515/ncrs-2023-0167
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C29 H27 Er N8 O9'
_chemical_formula_sum            'C29 H27 Er N8 O9'
_chemical_formula_weight         798.84
_chemical_name_systematic
;
(1-(pyridin-2-yl)-<i>N</i>-(pyridin-2-ylmethyl)-<i>N</i>-((1-(4-vinylbenzyl)-
1<i>H</i>-benzo[<i>d</i>]imidazol-2-yl)methyl)methanamine-k^4^<i>N</i>,
<i>N</i>',<i>N</i>'',<i>N</i>''')tri(nitrato-k<i>O</i>,<i>O</i>')-erbium(III)
;
_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     dual
_cell_angle_alpha                80.130(2)
_cell_angle_beta                 86.409(2)
_cell_angle_gamma                75.761(2)
_cell_formula_units_Z            2
_cell_length_a                   8.6681(2)
_cell_length_b                   13.0695(3)
_cell_length_c                   14.1408(4)
_cell_measurement_reflns_used    13042
_cell_measurement_temperature    295.52(10)
_cell_measurement_theta_max      76.9330
_cell_measurement_theta_min      4.3680
_cell_volume                     1529.43(7)
_computing_cell_refinement       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.52(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -18.00   7.00   0.50    0.17    --   48.55 -19.00 -90.00   50
  2  \w     40.00  65.00   0.50    0.69    --  108.86 -57.00-120.00   50
  3  \w     37.00  66.00   0.50    0.69    --  108.86 -57.00-150.00   58
  4  \w     87.00 177.00   0.50    0.69    --  108.86  77.00 -60.00  180
  5  \w    102.00 164.00   0.50    0.69    --  108.86 113.00 -97.00  124
  6  \w     -6.00  19.00   0.50    0.17    --  -48.55  57.00-120.00   50
  7  \w    -22.00  27.00   0.50    0.17    --  -48.55  19.00-180.00   98
  8  \w    -63.00 -31.00   0.50    0.17    --  -48.55  57.00-120.00   64
  9  \w    -26.00  27.00   0.50    0.17    --  -48.55  19.00 -30.00  106
 10  \w    -42.00  14.00   0.50    0.17    --  -48.55  38.00  60.00  112
 11  \w    -84.00 -19.00   0.50    0.69    --  -91.75 125.00  30.00  130
 12  \w    -83.00 -19.00   0.50    0.69    --  -91.75 125.00   0.00  128
 13  \w    -80.00 -40.00   0.50    0.69    --  -91.75 125.00 -30.00   80
 14  \w    -70.00 -42.00   0.50    0.69    --  -91.75 113.00 -97.00   56
 15  \w    -71.00 -19.00   0.50    0.69    --  -91.75 125.00-120.00  104
 16  \w    -76.00  -8.00   0.50    0.17    --  -48.55 113.00 -97.00  136
 17  \w    -56.00 -31.00   0.50    0.69    --  -91.75  57.00-180.00   50
 18  \w    -58.00 -23.00   0.50    0.69    --  -91.75  57.00 120.00   70
 19  \w     36.00  70.00   0.50    0.69    --  108.86 -99.00-150.00   68
 20  \w     49.00  97.00   0.50    0.69    --  108.86-125.00   0.00   96
 21  \w     80.00 112.00   0.50    0.69    --  108.86-125.00  30.00   64
 22  \w     76.00 108.00   0.50    0.69    --  108.86-109.00 -63.12   64
 23  \w     37.00  73.00   0.50    0.69    --  108.86-125.00  30.00   72
 24  \w     67.00 112.00   0.50    0.69    --  108.86-125.00 150.00   90
 25  \w     81.00 107.00   0.50    0.69    --  108.86-113.00 171.00   52
 26  \w     81.00 106.00   0.50    0.69    --  108.86 -99.00 120.00   50
 27  \w     44.00  74.00   0.50    0.17    --   48.55-113.00 171.00   60
 28  \w     53.00 102.00   0.50    0.69    --  108.86 -99.00  60.00   98
 29  \w     66.00 102.00   0.50    0.69    --  108.86 -99.00-120.00   72
 30  \w     74.00 100.00   0.50    0.69    --  108.86 -99.00-150.00   52
 31  \w     65.00 105.00   0.50    0.69    --  108.86 -99.00-180.00   80
 32  \w   -114.00 -73.00   0.50    0.17    --  -48.55-125.00 -30.00   82
 33  \w   -117.00 -91.00   0.50    0.17    --  -48.55-125.00-150.00   52
 34  \w   -152.00 -92.00   0.50    0.69    --  -91.75 -99.00-120.00  120
 35  \w   -126.00 -85.00   0.50    0.69    --  -91.75-113.00 171.00   82
 36  \w   -149.00 -92.00   0.50    0.69    --  -91.75 -19.00  30.00  114
 37  \w   -151.00 -73.00   0.50    0.69    --  -91.75 -77.00 120.00  156
 38  \w   -147.00 -77.00   0.50    0.69    --  -91.75 -57.00-120.00  140
 39  \w   -105.00 -76.00   0.50    0.69    --  -91.75 -77.00-150.00   58
 40  \w   -145.00-119.00   0.50    0.69    --  -91.75 -77.00-150.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0539292000
_diffrn_orient_matrix_UB_12      -0.0726051000
_diffrn_orient_matrix_UB_13      0.0868258000
_diffrn_orient_matrix_UB_21      0.1077632000
_diffrn_orient_matrix_UB_22      0.0336937000
_diffrn_orient_matrix_UB_23      0.0654478000
_diffrn_orient_matrix_UB_31      -0.1382595000
_diffrn_orient_matrix_UB_32      0.0936878000
_diffrn_orient_matrix_UB_33      0.0202904000
_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  0.0459
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18450
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.532
_diffrn_reflns_theta_min         3.535
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34353
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_description       block
_exptl_crystal_F_000             794
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.398
_refine_diff_density_min         -0.953
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         6022
_refine_ls_number_restraints     601
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0561P)^2^+2.1759P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5507
_reflns_number_total             6022
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0167_suppl_001.cif
_cod_data_source_block           exp_4996_auto
_cod_database_code               8107540
_shelx_estimated_absorpt_t_max   0.895
_shelx_estimated_absorpt_t_min   0.600
_olex2_refinement_description
;
1. Restrained distances
 O9-O10
 2.16 with sigma of 0.02
 O9A-N7 \\sim O9-N7
 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
N7 \\sim O8 \\sim O9 \\sim O10: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
N7 \\sim O8 \\sim O9A \\sim O10: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Others
 Sof(O9A)=1-FVAR(1)
 Sof(O9)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C17(H17A,H17B), C18(H18A,H18B), C24(H24A,H24B)
5.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C14(H14), C20(H20), C21(H21), C22(H22), C23(H23), C26(H26), C27(H27), C28(H28),
  C29(H29)
5.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
;
_shelx_res_checksum              30553
_shelx_hkl_checksum              15565
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.281
_oxdiff_exptl_absorpt_empirical_full_min 0.585