Transition-metal-free iterative two-fold reductive coupling and 1,3-borotropic shift to form 1,4-skipped dienes.
Varalaxmi, Kasarla; Pradhan, Kangkan; Begam, Hasina Mamataj; Polley, Arghya; Kumar, Deepak; Jana, Ranjan; Organic & biomolecular chemistry 22 (2024) 8596–8601; doi:10.1039/d4ob01389a

data_7160147
_publ_section_title
;
 Transition-metal-free iterative two-fold reductive coupling and
 1,3-borotropic shift to form 1,4-skipped dienes.
;
_journal_issue                   43
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              8596
_journal_page_last               8601
_journal_paper_doi               10.1039/d4ob01389a
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C20 H30'
_chemical_formula_sum            'C20 H30'
_chemical_formula_weight         270.461
_chemical_name_systematic        KVL-112
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_Int_Tables_number      14
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc2f3rlx
_audit_creation_date             2022-12-26
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-01-25 deposited with the CCDC.	2024-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.293(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2632(6)
_cell_length_b                   24.832(3)
_cell_length_c                   11.5592(12)
_cell_measurement_reflns_used    7770
_cell_measurement_temperature    115.0
_cell_measurement_theta_max      64.615
_cell_measurement_theta_min      3.560
_cell_volume                     1783.2(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-beta (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve 1.5-beta (Bourhis et al., 2015)'
_diffrn_ambient_temperature      115.0
_diffrn_measured_fraction_theta_full 0.9921
_diffrn_measured_fraction_theta_max 0.9921
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1617
_diffrn_reflns_av_unetI/netI     0.0708
_diffrn_reflns_Laue_measured_fraction_full 0.9921
_diffrn_reflns_Laue_measured_fraction_max 0.9921
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            23023
_diffrn_reflns_point_group_measured_fraction_full 0.9921
_diffrn_reflns_point_group_measured_fraction_max 0.9921
_diffrn_reflns_theta_full        64.9739
_diffrn_reflns_theta_max         64.97
_diffrn_reflns_theta_min         3.56
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.408
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.6517
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1214 before and 0.0740 after correction.
The Ratio of minimum to maximum transmission is 0.8659.
The \l/2 correction factor is Not present.
;
_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    1.007
_exptl_crystal_description       block
_exptl_crystal_F_000             601.535
_exptl_crystal_preparation       CHCl3
_exptl_crystal_recrystallization_method CHCl3
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.4397
_refine_diff_density_min         -0.3577
_refine_diff_density_rms         0.0701
_refine_ls_d_res_high            0.8508
_refine_ls_d_res_low             12.4158
_refine_ls_goodness_of_fit_ref   1.0375
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    46
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3022
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0375
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0757
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1331P)^2^+0.5349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2079
_refine_ls_wR_factor_ref         0.2146
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              6
_reflns_limit_h_min              -7
_reflns_limit_k_max              29
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              -5
_reflns_number_gt                2647
_reflns_number_total             3022
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d4ob01389a2.cif
_cod_data_source_block           kvl_0m_a
_cod_depositor_comments          'Adding full bibliography for 7160147.cif.'
_cod_original_sg_symbol_Hall     '-P 2ybc (x-z,y,z)'
_cod_database_code               7160147
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C11(H11), C8(H8), C2(H2), C3(H3), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C20(H20a,H20b,H20c), C18(H18a,H18b,H18c), C19(H19a,H19b,
 H19c), C17(H17a,H17b,H17c), C15(H15a,H15b,H15c), C16(H16a,H16b,H16c)
;
_olex2_exptl_crystal_mounting_method 'CRYSTAL WAS MOUNTED'
_olex2_submission_original_sample_id KVL-112
_olex2_submission_special_instructions 'No special instructions were received'