Total synthesis of atropisomeric indolosesquiterpenoids <i>via</i> N-N bond formation: dixiamycins A and B.
Nandi, Rhituparna; Niyogi, Sovan; Kundu, Sourav; Gavit, Vipin R.; Munda, Mintu; Murmu, Ranjit; Bisai, Alakesh; Chemical science 14 (2023) 8047–8053; doi:10.1039/d2sc07119c

data_1569431
_publ_section_title
;
 Total synthesis of atropisomeric indolosesquiterpenoids <i>via</i> N-N
 bond formation: dixiamycins A and B.
;
_journal_issue                   30
_journal_name_full               'Chemical science'
_journal_page_first              8047
_journal_page_last               8053
_journal_paper_doi               10.1039/d2sc07119c
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C24 H26 N2 O7, C2 H O2'
_chemical_formula_sum            'C26 H27 N2 O9'
_chemical_formula_weight         511.49
_chemical_name_systematic
'methyl (1S,2S,4aS)-1,4a-dimethyl-7-nitro-2-(nitrooxy)-6-phenyl-1,2,3,4,4a,9,10,10a-octahydrophenanthrene-1-carboxylate'
_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
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2dgbgp
_audit_creation_date             2022-11-08
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-08 deposited with the CCDC.	2023-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.08080(10)
_cell_length_b                   13.2575(2)
_cell_length_c                   31.0012(5)
_cell_measurement_reflns_used    7707
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.8630
_cell_measurement_theta_min      2.8510
_cell_volume                     2499.20(7)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix3000'
_diffrn_measurement_method       omega-scans
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            14987
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.227
_diffrn_reflns_theta_min         3.626
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72409
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   ABSPACK
_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    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             1076
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Hexane, Ethylacetate,Methanol'
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details
;
 Flack x determined using 1229 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.33(18)
_refine_ls_extinction_coef       0.0014(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0861
_refine_ls_R_factor_gt           0.0748
_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^)+(0.0999P)^2^+2.6206P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2050
_refine_ls_wR_factor_ref         0.2139
_reflns_Friedel_coverage         0.613
_reflns_Friedel_fraction_full    0.855
_reflns_Friedel_fraction_max     0.845
_reflns_number_gt                3637
_reflns_number_total             4258
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc07119c2.cif
_cod_data_source_block           rn202
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Empirical' was
changed to 'empirical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1569431.cif.
;
_cod_database_code               1569431
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.903
_shelx_estimated_absorpt_t_min   0.832
_olex2_refinement_description
;
1. Uiso/Uaniso restraints and constraints
Uanis(C21) = Uanis(C22) = Uanis(C23) = Uanis(C20) = Uanis(C24) = Uanis(C19)
2.a Ternary CH refined with riding coordinates:
 C10(H10), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C11(H11A,H11B), C6(H6A,H6B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C15(H15), C22(H22), C20(H20), C24(H24), C21(H21), C23(H23)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C1(H1A,H1B,H1C), C9(H9A,H9B,H9C)
2.e Idealised tetrahedral OH refined as rotating group:
 O(H)
;
_shelx_res_checksum              88014
_olex2_submission_special_instructions 'No special instructions were received'