3-Homoacyl coumarin: an all carbon 1,3-dipole for enantioselective concerted (3+2) cycloaddition.
Chen, Yi-Ru; Ganapuram, Madhusudhan Reddy; Hsieh, Kai-Hong; Chen, Kai-Han; Karanam, Praneeth; Vagh, Sandip Sambhaji; Liou, Yan-Cheng; Lin, Wenwei; Chemical communications (Cambridge, England) 54 (2018) 12702–12705; doi:10.1039/c8cc07271j

data_7122464
_publ_section_title
;
 3-Homoacyl coumarin: an all carbon 1,3-dipole for enantioselective
 concerted (3+2) cycloaddition.
;
_journal_issue                   90
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              12702
_journal_page_last               12705
_journal_paper_doi               10.1039/c8cc07271j
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C33 H21 Cl1 O5, 1.085(C H2 Cl2)'
_chemical_formula_sum            'C34.08 H23.17 Cl3.17 O5'
_chemical_formula_weight         625.09
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-10-16 deposited with the CCDC.
2018-10-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.015(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.2268(8)
_cell_length_b                   6.9147(4)
_cell_length_c                   33.035(2)
_cell_measurement_reflns_used    6234
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      21.60
_cell_measurement_theta_min      2.616
_cell_volume                     2984.0(3)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            20104
_diffrn_reflns_point_group_measured_fraction_full 0.800
_diffrn_reflns_point_group_measured_fraction_max 0.800
_diffrn_reflns_theta_full        25.003
_diffrn_reflns_theta_max         25.003
_diffrn_reflns_theta_min         1.248
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6768
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'psi-scan of intensities'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1286
_exptl_crystal_size_max          0.610
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.778
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.111
_refine_ls_abs_structure_details
;
 Flack x determined using 1934 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     730
_refine_ls_number_reflns         8423
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0734
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1286P)^2^+2.6930P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2069
_refine_ls_wR_factor_ref         0.2294
_reflns_Friedel_coverage         0.499
_reflns_Friedel_fraction_full    0.586
_reflns_Friedel_fraction_max     0.586
_reflns_number_gt                6545
_reflns_number_total             8423
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc07271j2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7122464.cif.'
_cod_database_code               7122464
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.808
_shelx_estimated_absorpt_t_max   0.964
_shelx_res_checksum              58322
_shelx_fab_checksum              33005