Catalytic enantioselective intramolecular 1,3-dipolar cycloaddition of azomethine ylides with fluorinated dipolarophiles
Cristóbal, Christian; Gaviña, Daniel; Alonso, Inés; Ribagorda, María; Carretero, Juan C.; del Pozo, Carlos; Adrio, Javier; Chemical Communications  (2022) –; doi:10.1039/D2CC02902B

data_7130275
_publ_section_title
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 Catalytic enantioselective intramolecular 1,3-dipolar cycloaddition of
 azomethine ylides with fluorinated dipolarophiles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC02902B
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_sum            'C82 H82 F6 N8 O12 S4'
_chemical_formula_weight         1613.79
_chemical_name_common            ccgnme
_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   mixed
_audit_update_record
;
2022-05-18 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 90.00(3)
_cell_angle_gamma                90.00(3)
_cell_formula_units_Z            1
_cell_length_a                   17.233(3)
_cell_length_b                   6.965(2)
_cell_length_c                   18.586(4)
_cell_measurement_reflns_used    3713
_cell_measurement_temperature    250.(2)
_cell_measurement_theta_max      21.5382
_cell_measurement_theta_min      3.3398
_cell_volume                     2230.8(9)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1328)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_diffrn_ambient_temperature      250.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa Apex II'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10595
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.19
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.178
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             844
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.134
_refine_diff_density_max         1.680
_refine_diff_density_min         -0.733
_refine_ls_abs_structure_details
;

Flack x determined using 974 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(3)
_refine_ls_extinction_coef       0.11(4)
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.872
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3936
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.873
_refine_ls_R_factor_all          0.1976
_refine_ls_R_factor_gt           0.1674
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4126
_refine_ls_wR_factor_ref         0.4383
_reflns_number_gt                2971
_reflns_number_total             3936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc02902b2.cif
_cod_data_source_block           03432def
_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 7556 2019-12-06 15:28:31Z antanas 
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_cod_database_code               7130275
_shelx_res_checksum              60371
_shelx_hkl_checksum              95826