A 3,4-dihalo-2(5H)-furanone initiated ring-opening reaction of DABCO in the absence of a metal catalyst and additive and its application in a one-pot two-step reaction
Wu, Han-Qing; Yang, Kai; Chen, Xiao-Yun; Arulkumar, Mani; Wang, Neng; Chen, Si-Hong; Wang, Zhao-Yang; Green Chemistry 21 (2019) 3782–; doi:10.1039/C9GC01740B

data_7232918
_publ_section_title
;
 A 3,4-dihalo-2(5H)-furanone initiated ring-opening reaction of DABCO in
 the absence of a metal catalyst and additive and its application in a
 one-pot two-step reaction
;
_journal_issue                   14
_journal_name_full               'Green Chemistry'
_journal_page_first              3782
_journal_paper_doi               10.1039/C9GC01740B
_journal_volume                  21
_journal_year                    2019
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C16 H24 Cl2 N2 O3'
_chemical_formula_sum            'C16 H24 Cl2 N2 O3'
_chemical_formula_weight         363.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2296n8
_audit_creation_date             2019-03-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-12 deposited with the CCDC.    2019-06-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1568(15)
_cell_length_b                   17.163(2)
_cell_length_c                   9.1319(15)
_cell_measurement_reflns_used    1617
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.8310
_cell_measurement_theta_min      3.8370
_cell_volume                     1748.6(4)
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_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 0.997
_diffrn_measured_fraction_theta_max 0.988
_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      4.00  73.00   1.00    7.50    --   15.34  57.00 -90.00   69
  2  \w    -55.00 -29.00   1.00    7.50    --  -16.12 -38.00 120.00   26
  3  \w    -84.00  24.00   1.00    7.50    --  -16.12   0.00 -30.00  108
;
_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      -0.0192621000
_diffrn_orient_matrix_UB_12      0.0065456000
_diffrn_orient_matrix_UB_13      0.0730364000
_diffrn_orient_matrix_UB_21      0.0397121000
_diffrn_orient_matrix_UB_22      0.0321440000
_diffrn_orient_matrix_UB_23      0.0055135000
_diffrn_orient_matrix_UB_31      -0.0456898000
_diffrn_orient_matrix_UB_32      0.0251282000
_diffrn_orient_matrix_UB_33      -0.0260714000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.1307
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7165
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         3.652
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.387
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62168
_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 white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details
;
 Flack x determined using 508 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3618
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.892
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0613
_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^)+(0.0267P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0862
_refine_ls_wR_factor_ref         0.1040
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.942
_reflns_Friedel_fraction_max     0.899
_reflns_number_gt                1830
_reflns_number_total             3618
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9gc01740b2.cif
_cod_data_source_block           exp_6529
_cod_depositor_comments          'Adding full bibliography for 7232918.cif.'
_cod_database_code               7232918
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.955
_shelx_estimated_absorpt_t_min   0.906
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B), C4(H4A,H4B), C3(H3A,H3B), C15(H15A,H15B), C16(H16A,
 H16B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C2(H2A,H2B), C1(H1A,H1B)
;
_shelx_res_checksum              18681
_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 1.679
_oxdiff_exptl_absorpt_empirical_full_min 0.649