Lewis Acid-Mediated Ring-Opening Reactions of trans-2-Aroyl-3-styryl-cyclopropane-1,1-dicarboxylates: Access to Cyclopentenes and E,E-1,3-Dienes.
Thangamani, Murugesan; Kannupal, Srinivasan; The Journal of organic chemistry  (2017) –; doi:10.1021/acs.joc.7b02335

data_4033297
_publ_section_title
;
 Lewis Acid-Mediated Ring-Opening Reactions of
 trans-2-Aroyl-3-styryl-cyclopropane-1,1-dicarboxylates: Access to
 Cyclopentenes and E,E-1,3-Dienes.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.7b02335
_journal_year                    2017
_chemical_formula_moiety         'C24 H23 N O7'
_chemical_formula_sum            'C24 H23 N O7'
_chemical_formula_weight         437.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-04
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.618(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.832(2)
_cell_length_b                   11.4226(13)
_cell_length_c                   22.574(3)
_cell_measurement_reflns_used    67624
_cell_measurement_temperature    297(2)
_cell_measurement_theta_max      27.641
_cell_measurement_theta_min      2.231
_cell_volume                     4519.3(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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      297.21
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0942
_diffrn_reflns_av_unetI/netI     0.0737
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            67624
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.641
_diffrn_reflns_theta_min         2.231
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       Block
_exptl_crystal_F_000             1804
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       0.0031(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         10353
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.1508
_refine_ls_R_factor_gt           0.0888
_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^)+(0.1644P)^2^+2.8649P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2426
_refine_ls_wR_factor_ref         0.2842
_reflns_Friedel_coverage         0.999
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                6202
_reflns_number_total             10353
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b02335_si_003.cif
_cod_data_source_block           rn65a
_cod_depositor_comments
;

2025-10-08
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C47 H43 N2 O14'
_cod_original_formula_weight         859.83
_cod_original_formula_moiety         '2(C23.46 H21.37 N O7)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        4519.4(9)
_cod_database_code               4033297
_shelx_shelxl_version_number     2016/4
_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. Others
 Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(C21B)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C18B(H18B), C18A(H18A)
3.b Secondary CH2 refined with riding coordinates:
 C23B(H23A,H23B), C23A(H23C,H23D), C20B(H20A,H20B), C20A(H20C,H20D)
3.c Me refined with riding coordinates:
 C24A(H24D,H24E,H24F)
3.d Aromatic/amide H refined with riding coordinates:
 C9B(H9B), C8B(H8B), C7B(H7B), C13B(H13B), C5B(H5B), C17A(H17A), C3B(H3B),
 C2B(H2B), C3A(H3A), C5A(H5A), C8A(H8A), C13A(H13A), C6A(H6A), C9A(H9A),
 C15B(H15B), C6B(H6B), C7A(H7A), C14A(H14A), C16A(H16A), C14B(H14B), C17B(H17B),
  C2A(H2A), C16B(H16B), C15A(H15A)
3.e Idealised Me refined as rotating group:
 C24B(H24A,H24B,H24C), C21B(H21A,H21B,H21C), C21A(H21D,H21E,H21F)
;
_shelx_res_checksum              57679
_shelx_hkl_checksum              17830
_olex2_submission_special_instructions 'No special instructions were received'