Asymmetric Total Synthesis of (+)-Dihydroitomanallene B and Formal Synthesis of (-)-Kumausallene
Fernandes, Rodney Agustinho; Kumar, Atul; Pathare, Ramdas Shivaji; Chemical Communications  (2022) –; doi:10.1039/D2CC04574E

data_7130778
_publ_section_title
;
 Asymmetric Total Synthesis of (+)-Dihydroitomanallene B and Formal
 Synthesis of (-)-Kumausallene
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04574E
_journal_year                    2022
_chemical_formula_moiety         'C22 H21 N2 O9'
_chemical_formula_sum            'C22 H21 N2 O9'
_chemical_formula_weight         457.41
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-07-13
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-07-16 deposited with the CCDC.	2022-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.911(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0311(7)
_cell_length_b                   41.153(3)
_cell_length_c                   7.9883(11)
_cell_measurement_reflns_used    3066
_cell_measurement_temperature    150
_cell_measurement_theta_max      27.8410
_cell_measurement_theta_min      2.8060
_cell_volume                     2129.1(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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      150
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_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   -110.00  70.00   1.00   16.00    --  -20.00   0.00-108.00  180
  2  \w   -107.00 -72.00   1.00   16.00    --  -20.00 -72.00-180.00   35
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1019
_diffrn_reflns_av_unetI/netI     0.1479
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8643
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.979
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             956
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.142
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.1676
_refine_ls_R_factor_gt           0.0849
_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^)+(0.1575P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2095
_refine_ls_wR_factor_ref         0.3167
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1844
_reflns_number_total             3679
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04574e2.cif
_cod_data_source_block           raf-ram-061_mo
_cod_original_cell_volume        2129.1(4)
_cod_database_code               7130778
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.979
_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.a Ternary CH refined with riding coordinates:
 C00L(H00L), C00T(H00T), C00U(H00U)
2.b Secondary CH2 refined with riding coordinates:
 C00Q(H00A,H00B), C00R(H00D,H00E), C00S(H00F,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00G(H00G), C00I(H00I), C00M(H00M), C00N(H00N), C00O(H00O),
 C00P(H00P), C00W(H00W), C00X(H00X)
2.d Idealised Me refined as rotating group:
 C00V(H00J,H00K,H00Q)
;
_shelx_res_checksum              91573
_shelx_hkl_checksum              83750
_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
;