Synthesis of selected plant metabolites of icafolin-methyl <i>via</i> the formation of a spirocyclic nitronate.
Schulz, Göran; Maletz, Julia; Janisch, Pascal; Moczarski, Stefan; Ostrovskyi, Dmytro; Organic & biomolecular chemistry 23 (2025) 2726–2730; doi:10.1039/d5ob00132c

data_7160375
_publ_section_title
;
 Synthesis of selected plant metabolites of icafolin-methyl <i>via</i> the
 formation of a spirocyclic nitronate.
;
_journal_issue                   11
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2726
_journal_page_last               2730
_journal_paper_doi               10.1039/d5ob00132c
_journal_volume                  23
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H16 F2 N2 O6'
_chemical_formula_sum            'C17 H16 F2 N2 O6'
_chemical_formula_weight         382.32
_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_method           SHELXL-2018/3
_audit_update_record
;
2024-12-17 deposited with the CCDC.	2025-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.7401(5)
_cell_length_b                   15.6633(10)
_cell_length_c                   16.0978(12)
_cell_measurement_reflns_used    7160
_cell_measurement_temperature    110
_cell_measurement_theta_max      64.10
_cell_measurement_theta_min      3.94
_cell_volume                     1699.5(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      110
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11024
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        64.258
_diffrn_reflns_theta_max         64.258
_diffrn_reflns_theta_min         5.496
_diffrn_source                   'microfocus source tube IuS'
_exptl_absorpt_coefficient_mu    1.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_description       Block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   0.92
_exptl_transmission_factor_min   0.8
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 1029 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0290
_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^)+(0.0345P)^2^+0.1811P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0696
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                2594
_reflns_number_total             2785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00132c2.cif
_cod_data_source_block           SPSA247122LTCuX820240507_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' 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 7160375--7160376.cif.
;
_cod_database_code               7160375
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.471
_shelx_estimated_absorpt_t_max   0.874
_shelx_res_checksum              28249