The crystal structure of (2R,6′R)-2′,7-dichloro-4,6-dimethoxy-6′-methyl-3H-spiro[benzofuran-2,1′-cyclohexan]-2′-ene-3,4′-dione, C16H14Cl2O5
Zhang, Meng; Bai, Yu-Bin; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 185–187; doi:10.1515/ncrs-2022-0538

data_8107390
_publ_section_title
;
 The crystal structure of
 (2R,6&#x2032;R)-2&#x2032;,7-dichloro-4,6-dimethoxy-6&#x2032;-methyl-3H-spiro[benzofuran-2,1&#x2032;-cyclohexan]-2&#x2032;-ene-3,4&#x2032;-dione,
 C16H14Cl2O5
;
_journal_issue                   2
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              185
_journal_page_last               187
_journal_paper_doi               10.1515/ncrs-2022-0538
_journal_volume                  238
_journal_year                    2023
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H14 Cl2 O5'
_chemical_formula_sum            'C16 H14 Cl2 O5'
_chemical_formula_weight         357.17
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   23.2297(5)
_cell_length_b                   16.3509(3)
_cell_length_c                   8.7300(2)
_cell_measurement_reflns_used    7489
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.5260
_cell_measurement_theta_min      4.6380
_cell_volume                     3315.89(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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     14.00 100.00   1.00    1.50    --   36.10  38.00 -30.00   86
  2  \w     82.00 107.00   1.00    1.50    --   36.10  38.00  90.00   25
  3  \w     35.00  63.00   1.00    1.50    --   36.10  38.00  90.00   28
  4  \w     27.00  53.00   1.00    1.50    --   36.10 -57.00 120.00   26
  5  \w     26.00  84.00   1.00    1.50    --   36.10-125.00  90.00   58
  6  \w     39.00  77.00   1.00    1.50    --   36.10 -99.00 -30.00   38
  7  \w     22.00  49.00   1.00    1.50    --   36.10 -77.00 -90.00   27
  8  \w      1.00  55.00   1.00    1.50    --   36.10 -99.00 -90.00   54
  9  \w    108.00 177.00   1.00    5.00    --  108.00 111.00  90.00   69
 10  \w     72.00 123.00   1.00    5.00    --  108.00 -50.00  60.00   51
 11  \w     45.00  75.00   1.00    5.00    --  108.00 -50.00 150.00   30
 12  \w     42.00 164.00   1.00    5.00    --  108.00   0.00  30.00  122
 13  \w     71.00 114.00   1.00    5.00    --  108.00-111.00-150.00   43
 14  \w     43.00 122.00   1.00    5.00    --  108.00 -77.00-150.00   79
 15  \w     38.00  64.00   1.00    5.00    --  108.00-111.00-150.00   26
 16  \w     40.00 123.00   1.00    5.00    --  108.00 -50.00   0.00   83
 17  \w     63.00 105.00   1.00    1.50    --   36.10  57.00-180.00   42
 18  \w    -31.00  -6.00   1.00    1.50    --   36.10 -77.00 -90.00   25
 19  \w    -22.00  19.00   1.00    1.50    --   36.10 -57.00 120.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0020998000
_diffrn_orient_matrix_UB_12      -0.0385135000
_diffrn_orient_matrix_UB_13      0.1610421000
_diffrn_orient_matrix_UB_21      0.0063709000
_diffrn_orient_matrix_UB_22      0.0854844000
_diffrn_orient_matrix_UB_23      0.0723653000
_diffrn_orient_matrix_UB_31      -0.0659273000
_diffrn_orient_matrix_UB_32      0.0095016000
_diffrn_orient_matrix_UB_33      0.0017677000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13604
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.702
_diffrn_reflns_theta_min         3.806
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.727
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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    1.431
_exptl_crystal_description       block
_exptl_crystal_F_000             1472
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details
;
 Flack x determined using 2353 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.006(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     421
_refine_ls_number_reflns         6350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0472
_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/[\s^2^(Fo^2^)+(0.0770P)^2^+0.2391P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1268
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                5967
_reflns_number_total             6350
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0538_suppl.cif
_cod_data_source_block           exp_11387
_cod_database_code               8107390
_shelx_estimated_absorpt_t_max   0.663
_shelx_estimated_absorpt_t_min   0.554
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C31(H31), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C3(H3), C12(H12), C28(H28)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C23(H23A,H23B,H23C), C32(H32A,H32B,H32C), C7(H7A,H7B,
 H7C), C8(H8A,H8B,H8C), C16(H16A,H16B,H16C)
;
_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 3.044
_oxdiff_exptl_absorpt_empirical_full_min 0.582