Visible-light-enabled stereoselective synthesis of functionalized cyclohexylamine derivatives <i>via</i> [4 + 2] cycloadditions.
Lu, Yi-Nan; Che, Chao; Zhen, Guangjin; Chang, Xin; Dong, Xiu-Qin; Wang, Chun-Jiang; Chemical science 15 (2024) 6507–6514; doi:10.1039/d4sc00667d

data_1571299
_publ_section_title
;
 Visible-light-enabled stereoselective synthesis of functionalized
 cyclohexylamine derivatives <i>via</i> [4 + 2] cycloadditions.
;
_journal_issue                   17
_journal_name_full               'Chemical science'
_journal_page_first              6507
_journal_page_last               6514
_journal_paper_doi               10.1039/d4sc00667d
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C26 H24 O'
_chemical_formula_sum            'C26 H24 O'
_chemical_formula_weight         352.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-24
_audit_creation_method
;
Olex2 1.5-ac6-012
(compiled 2023.08.24 svn.re1ec1418 for Rigaku Oxford Diffraction, GUI svn.r6817)
;
_audit_update_record
;
2023-12-26 deposited with the CCDC.	2024-03-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.7125(3)
_cell_length_b                   7.21700(10)
_cell_length_c                   22.9642(3)
_cell_measurement_reflns_used    20386
_cell_measurement_temperature    293
_cell_measurement_theta_max      74.0370
_cell_measurement_theta_min      3.8820
_cell_volume                     3764.20(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-012 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     34.00  83.00   0.50    0.50    --    0.00  64.00  22.61   98
  2  \w    -24.00  28.00   0.50    0.50    --    0.00  64.00  22.61  104
  3  \w    -22.00  80.00   0.50    0.50    --    0.00  56.00 117.19  204
  4  \w    -28.00  15.00   0.50    0.50    --    0.00 -82.00  60.00   86
  5  \w    -30.00  -5.00   0.50    0.50    --    0.00 -82.00  30.00   50
  6  \w     34.00 122.00   0.50    1.00    --   95.20 -82.00 -60.00  176
  7  \w     10.00  41.00   0.50    1.00    --   95.20 -82.00 150.00   62
  8  \w     87.00 126.00   0.50    1.00    --   95.20 -82.00  90.00   78
  9  \w      7.00 112.00   0.50    1.00    --   95.20 -61.00 -60.00  210
 10  \w     89.00 185.00   0.50    1.00    --   95.20  61.00 -90.00  192
 11  \w     76.00 102.00   0.50    1.00    --   95.20 -82.00-150.00   52
 12  \w     61.00 100.00   0.50    1.00    --   95.20 -82.00 150.00   78
 13  \w      6.00 112.00   0.50    1.00    --   95.20 -30.00-180.00  212
 14  \w     65.00 127.00   0.50    1.00    --   95.20 -82.00  30.00  124
 15  \w     18.00  67.00   0.50    1.00    --   95.20 -82.00  90.00   98
 16  \w     76.00 110.00   0.50    1.00    --   95.20 -45.00  30.00   68
 17  \w     14.00  42.00   0.50    1.00    --   95.20 -45.00  30.00   56
 18  \w     53.00  92.00   0.50    1.00    --   95.20 -45.00-180.00   78
 19  \w     59.00 101.00   0.50    1.00    --   95.20 -82.00-120.00   84
 20  \w     89.00 125.00   0.50    1.00    --   95.20 -82.00   0.00   72
 21  \w     19.00 106.00   0.50    1.00    --   95.20 -82.00-180.00  174
 22  \w     97.00 139.00   0.50    1.00    --   95.20  77.00 -30.00   84
 23  \w     79.00 182.00   0.50    1.00    --   95.20  30.00-150.00  206
 24  \w     74.00 166.00   0.50    1.00    --   95.20  15.00  30.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0028302000
_diffrn_orient_matrix_UB_12      0.0378490000
_diffrn_orient_matrix_UB_13      -0.0659597000
_diffrn_orient_matrix_UB_21      -0.0675674000
_diffrn_orient_matrix_UB_22      0.0141273000
_diffrn_orient_matrix_UB_23      0.0036202000
_diffrn_orient_matrix_UB_31      0.0050466000
_diffrn_orient_matrix_UB_32      0.2096497000
_diffrn_orient_matrix_UB_33      0.0116901000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0757
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            38918
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.307
_diffrn_reflns_theta_min         3.850
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.565
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       prism
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3805
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0420
_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^)+(0.0596P)^2^+1.5294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1107
_refine_ls_wR_factor_ref         0.1129
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3537
_reflns_number_total             3805
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc00667d2.cif
_cod_data_source_block           20231107_lyn
_cod_depositor_comments
'Adding full bibliography for 1571298--1571300.cif.'
_cod_database_code               1571299
_shelx_shelxl_version_number     2018/3
_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.a Ternary CH refined with riding coordinates:
 C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00C(H00C,H00D), C00D(H00E,H00F), C00H(H00J,H00K)
2.c Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00E(H00G), C00F(H00H), C00G(H00I), C00I(H00L),
 C00J(H00M), C00K(H00N), C00L(H00O), C00M(H00P), C00N(H00Q), C00P(H00U),
 C00Q(H00V), C00R(H00W)
2.d Idealised Me refined as rotating group:
 C00O(H00R,H00S,H00T)
;
_shelx_res_checksum              48416
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.832
_oxdiff_exptl_absorpt_empirical_full_min 0.429