Simple and efficient synthesis of bicyclic enol-carbamates: access to brabantamides and their analogues
Záborský, Ondrej; Petrovičová, Ľudmila; Doháňošová, Jana; Moncol, Ján; Fischer, Róbert; RSC Advances 10 (2020) 6790–6793; doi:10.1039/D0RA00796J

data_7240052
_publ_section_title
;
 Simple and efficient synthesis of bicyclic enol-carbamates: access to
 brabantamides and their analogues
;
_journal_issue                   12
_journal_name_full               'RSC Advances'
_journal_page_first              6790
_journal_page_last               6793
_journal_paper_doi               10.1039/D0RA00796J
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H38 N2 O3'
_chemical_formula_sum            'C22 H38 N2 O3'
_chemical_formula_weight         378.54
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-09-17 deposited with the CCDC.	2020-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.8450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.52490(10)
_cell_length_b                   9.17550(10)
_cell_length_c                   24.7518(3)
_cell_measurement_reflns_used    77628
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.25
_cell_measurement_theta_min      3.59
_cell_volume                     2151.95(4)
_computing_cell_refinement
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011 (Burla et al., 2007)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari with Xenocs Genix3D Cu HF'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0155
_diffrn_reflns_av_unetI/netI     0.0072
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            68366
_diffrn_reflns_point_group_measured_fraction_full 0.896
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.821
_diffrn_reflns_theta_min         3.590
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  0.770
_exptl_absorpt_correction_T_min  0.289
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       plate
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 2829 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         7376
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0494P)^2^+0.4065P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0806
_reflns_Friedel_coverage         0.649
_reflns_Friedel_fraction_full    0.778
_reflns_Friedel_fraction_max     0.735
_reflns_number_gt                7303
_reflns_number_total             7376
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ra00796j2.cif
_cod_data_source_block           21
_cod_depositor_comments
'Adding full bibliography for 7240050--7240052.cif.'
_cod_database_code               7240052
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.772
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1A(H1A), C1B(H1B)
2.b Secondary CH2 refined with riding coordinates:
 C4A(H4AA,H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C9A(H9AA,H9AB), C10A(H10A,
 H10B), C11A(H11A,H11B), C12A(H12A,H12B), C13A(H13A,H13B), C14A(H14A,H14B),
 C15A(H15A,H15B), C16A(H16A,H16B), C17A(H17A,H17B), C18A(H18A,H18B), C19A(H19A,
 H19B), C20A(H20A,H20B), C21A(H21A,H21B), C4B(H4BA,H4BB), C5B(H5BA,H5BB),
 C6B(H6BA,H6BB), C9B(H9BA,H9BB), C10B(H10C,H10D), C11B(H11C,H11D), C12B(H12C,
 H12D), C13B(H13C,H13D), C14B(H14C,H14D), C15B(H15C,H15D), C16B(H16C,H16D),
 C17B(H17C,H17D), C18B(H18C,H18D), C19B(H19C,H19D), C20B(H20C,H20D), C21B(H21C,
 H21D)
2.c Aromatic/amide H refined with riding coordinates:
 N2A(H2A), C7A(H7A), N2B(H2B), C7B(H7B)
2.d Idealised Me refined as rotating group:
 C22A(H22A,H22B,H22C), C22B(H22D,H22E,H22F)
;
_shelx_res_checksum              91325
_olex2_submission_special_instructions 'No special instructions were received'