Native Carboxylate-Assisted Enantioselective C-H Annulations with Allenes and 1,3-Dienes on Ferrocene
Parganiha, Devendra; Upadhyay, Yagya Dutt; Khevariya, Sumit; Patil, Pruthviraj Amar; Jaiswal, Svastik; Dhasmana, Yogesh; Kumar, Sangit; Chemical Communications  (2026) –; doi:10.1039/D5CC06160A

data_7135325
_publ_section_title
;
 Native Carboxylate-Assisted Enantioselective C-H Annulations with Allenes
 and 1,3-Dienes on Ferrocene
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D5CC06160A
_journal_year                    2026
_chemical_formula_moiety         'C28 H22 Fe O2'
_chemical_formula_sum            'C28 H22 Fe O2'
_chemical_formula_weight         446.30
_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
_audit_creation_date             2025-07-12
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-10-28 deposited with the CCDC.	2025-12-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2412(6)
_cell_length_b                   11.3911(8)
_cell_length_c                   21.8790(15)
_cell_measurement_reflns_used    2826
_cell_measurement_temperature    140.00
_cell_measurement_theta_max      21.84
_cell_measurement_theta_min      2.58
_cell_volume                     2053.9(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      140.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1151
_diffrn_reflns_av_unetI/netI     0.0725
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            33287
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.712
_diffrn_reflns_theta_max         24.712
_diffrn_reflns_theta_min         2.016
_diffrn_source_current           1.39
_diffrn_source_power             0.0695
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6647
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0899 before and 0.0741 after correction.
The Ratio of minimum to maximum transmission is 0.8920.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_description       Block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.066
_refine_ls_abs_structure_details
;
 Flack x determined using 934 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         3508
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0535
_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^)+(0.0377P)^2^+2.4458P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1270
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2708
_reflns_number_total             3508
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc06160a3.cif
_cod_data_source_block           3d
_cod_database_code               7135325
_shelx_shelxl_version_number     2019/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
C00N \\sim C00Q \\sim C00U \\sim C00R \\sim C00J \\sim C00G: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
C00I \\sim C008 \\sim C00C \\sim C00M \\sim C00S \\sim C00P: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C00Q) \\sim Ueq, Uanis(C00U) \\sim Ueq, Uanis(C00R) \\sim Ueq,
Uanis(C00N) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C00P) \\sim Ueq, Uanis(C00S) \\sim Ueq, Uanis(C00M) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(C1) = Uanis(C4)
Uanis(C2) = Uanis(C3)
3. Others
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C4)=Sof(H4A)=Sof(H4B)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C3)=Sof(H3A)=Sof(H3B)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C00K(H00B,H00D), C1(H1A,H1B), C3(H3A,H3B), C2(H2A,H2B), C4(H4A,H4B)
4.b Aromatic/amide H refined with riding coordinates:
 C004(H004), C005(H005), C00A(H00A), C00C(H00C), C00E(H00E), C00F(H00F),
 C00H(H00H), C00J(H00J), C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00U(H00U)
;
_shelx_res_checksum              58079
_shelx_hkl_checksum              42878
_olex2_submission_special_instructions 'No special instructions were received'