Bicyclic Piperidines <i>via</i> [2 + 2] Photocycloaddition.
Shcherbakova, Valeriya; Dibchak, Dmitry; Snisarenko, Mariya; Skalenko, Yevhen; Denisenko, Aleksandr V.; Kuznetsova, Anastasiia S.; Mykhailiuk, Pavel K.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c02355

data_4038944
_publ_section_title
;
 Bicyclic Piperidines <i>via</i> [2 + 2] Photocycloaddition.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c02355
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C19 H24 N O, Cl'
_chemical_formula_sum            'C19 H24 Cl N O'
_chemical_formula_weight         317.84
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_block_doi                 10.5517/ccwxhx5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_creation_date             2011-06-23T16:24:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2011-06-27 deposited with the CCDC.	2020-09-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6019(5)
_cell_length_b                   12.1084(8)
_cell_length_c                   18.2856(11)
_cell_measurement_reflns_used    2204
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9813
_cell_measurement_theta_min      3.348
_cell_measurement_wavelength     0.71073
_cell_volume                     1683.13(19)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.4685
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0660477
_diffrn_orient_matrix_UB_12      -0.0081589
_diffrn_orient_matrix_UB_13      0.0268615
_diffrn_orient_matrix_UB_21      0.0643568
_diffrn_orient_matrix_UB_22      -0.0043061
_diffrn_orient_matrix_UB_23      -0.0279177
_diffrn_orient_matrix_UB_31      0.0140372
_diffrn_orient_matrix_UB_32      0.0578811
_diffrn_orient_matrix_UB_33      0.0017072
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0935
_diffrn_reflns_av_unetI/netI     0.1193
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11613
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         3.35
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.3988
_exptl_crystal_size_mid          0.2798
_exptl_crystal_size_min          0.0864
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.16
_refine_diff_density_rms         0.04
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.32(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.833
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.833
_refine_ls_R_factor_all          0.085
_refine_ls_R_factor_gt           0.0387
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0147P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0565
_refine_ls_wR_factor_ref         0.0625
_reflns_number_gt                1904
_reflns_number_total             2966
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo0c02355_si_002.cif
_cod_data_source_block           ojrl343
_cod_original_cell_volume        1683.12(19)
_cod_database_code               4038944