General acid-mediated aminolactone formation using unactivated alkenes.
Just, David; Gonçalves, Carlos R; Vezonik, Uroš; Kaiser, Daniel; Maulide, Nuno; Chemical science 14 (2023) 10806–10811; doi:10.1039/d3sc04073a

data_1570017
_publ_section_title
;
 General acid-mediated aminolactone formation using unactivated alkenes.
;
_journal_issue                   39
_journal_name_full               'Chemical science'
_journal_page_first              10806
_journal_page_last               10811
_journal_paper_doi               10.1039/d3sc04073a
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C17 H23 N O2'
_chemical_formula_sum            'C17 H23 N O2'
_chemical_formula_weight         273.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-11-25
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-29 deposited with the CCDC.	2023-09-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.824(11)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.635(2)
_cell_length_b                   10.097(2)
_cell_length_c                   20.471(3)
_cell_measurement_reflns_used    5446
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.74
_cell_measurement_theta_min      2.26
_cell_volume                     2937.4(8)
_computing_cell_refinement
;
X-Area Recipe 1.36.0.0 (STOE, 2020)
;
_computing_data_collection
;
X-Area Pilatus3_SV 1.31.170.0 (STOE, 2020)
;
_computing_data_reduction
;
X-Area Integrate 1.78.3.0 (STOE, 2020)
X-Area LANA 1.83.8.0 (STOE, 2020)
;
_computing_molecular_graphics    'Olex2 1.5 (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 1.90, Darmstadt 2020
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'EIGER2 500K'
_diffrn_detector_area_resol_mean 13.33
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details
;
 2445 frames, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, \w scans'
_diffrn_radiation_collimation    '1.2 0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_av_unetI/netI     0.0968
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13059
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_min         2.049
_diffrn_source                   'Axo Mo'
_diffrn_source_current           0.830
_diffrn_source_power             0.050
_diffrn_source_voltage           60
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9930
_exptl_absorpt_correction_T_min  0.6926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(\m~2~-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
Afterwards a spherical absorption correction was performed within STOE LANA.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.483
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.0052(19)
_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   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         2744
_refine_ls_number_restraints     46
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1699
_refine_ls_R_factor_gt           0.0991
_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^)+(0.1750P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2760
_refine_ls_wR_factor_ref         0.3023
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1290
_reflns_number_total             2744
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04073a2.cif
_cod_data_source_block           daju196maj
_cod_depositor_comments          'Adding full bibliography for 1570017.cif.'
_cod_original_cell_volume        2937.6(8)
_cod_database_code               1570017
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.953
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1B-C14B \\sim N1A-C14A \\sim N1A-C16A \\sim N1A-C17A \\sim N1B-C17B \\sim
N1B-C16B
 with sigma of 0.02
 C1-C15A \\sim C1-C15B \\sim C14B-C15B \\sim C14A-C15A
 with sigma of 0.02
 O1-C13A \\sim O1-C13B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N1B) \\sim Ueq, Uanis(N1A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C16B) \\sim Ueq, Uanis(C17B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C15B) = Uanis(C15A)
Uanis(O1B) = Uanis(O1A)
Uanis(C13A) = Uanis(C13B)
4. Others
 Sof(O1B)=Sof(N1B)=Sof(C13B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(H15C)=Sof(H15D)=
 Sof(C16B)=Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C17B)=Sof(H17D)=Sof(H17E)=
 Sof(H17F)=1-FVAR(1)
 Sof(O1A)=Sof(N1A)=Sof(C13A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=Sof(H15B)=
 Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17A)=Sof(H17A)=Sof(H17B)=
 Sof(H17C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C14A(H14A), C14B(H14B)
5.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C15A(H15A,H15B),
 C15B(H15C,H15D)
5.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
5.d Idealised Me refined as rotating group:
 C16A(H16A,H16B,H16C), C17A(H17A,H17B,H17C), C16B(H16D,H16E,H16F), C17B(H17D,
 H17E,H17F)
;
_shelx_res_checksum              29853
_olex2_submission_special_instructions 'No special instructions were received'