Asymmetric Petasis reaction for the synthesis of chiral α- and β-butadienyl amines.
Xie, Yi-Wen; Zhao, Zhen-Ni; Lin, Zi-Wei; Wang, Yu-Hao; Liu, Ya-Qun; Huang, Yi-Yong; Chemical communications (Cambridge, England) 57 (2021) 2364–2367; doi:10.1039/d0cc08241d

data_7127867
_publ_section_title
;
 Asymmetric Petasis reaction for the synthesis of chiral \a- and
 \b-butadienyl amines.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2364
_journal_page_last               2367
_journal_paper_doi               10.1039/d0cc08241d
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C19 H21 N O2'
_chemical_formula_sum            'C19 H21 N O2'
_chemical_formula_weight         295.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-07
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_audit_update_record
;
2020-08-13 deposited with the CCDC.	2021-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.370(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.510(2)
_cell_length_b                   5.7053(5)
_cell_length_c                   10.3731(9)
_cell_measurement_reflns_used    7731
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.42
_cell_measurement_theta_min      2.36
_cell_volume                     1620.9(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0153
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.934
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12012
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.675
_diffrn_reflns_theta_min         1.487
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0900 before and 0.0311 after correction. The Ra'
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_F_000             632
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details
; 
 Flack x determined using 1625 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.6(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         4164
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0373
_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^)+(0.0630P)^2^+0.3526P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1050
_reflns_Friedel_coverage         0.772
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                3896
_reflns_number_total             4164
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0cc08241d2.cif
_cod_data_source_block           mo_191216e_0m
_cod_depositor_comments          'Adding full bibliography for 7127867.cif.'
_cod_database_code               7127867
_shelx_shelxl_version_number     2014/7
_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 O(H) groups 
2.a Ternary CH refined with riding coordinates: 
 C1(H1), C2(H2), C10(H10) 
2.b Secondary CH2 refined with riding coordinates: 
 C3(H3A,H3B), C15(H15A,H15B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C17(H17) 
2.d X=CH2 refined with riding coordinates: 
 C18(H18A,H18B), C19(H19A,H19B) 
2.e Idealised tetrahedral OH refined as rotating group: 
 O1(H1B) 
;
_olex2_submission_special_instructions 'No special instructions were received'