Photoinduced Intermolecular [4+2] Cycloaddition Reaction for Construction of Benzobicyclo[2.2.2]octane Skeletons.
Liu, Qiang; Wang, Junlei; Li, Dazhi; Yang, Chao; Xia, Wujiong; The Journal of organic chemistry 82 (2017) 1389–1402; doi:10.1021/acs.joc.6b02547

data_4032144
_publ_section_title
;
 Photoinduced Intermolecular [4+2] Cycloaddition Reaction for Construction
 of Benzobicyclo[2.2.2]octane Skeletons.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1389
_journal_page_last               1402
_journal_paper_doi               10.1021/acs.joc.6b02547
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C22 H25 N O6'
_chemical_formula_sum            'C22 H25 N O6'
_chemical_formula_weight         399.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-06-20
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                76.523(8)
_cell_angle_beta                 80.432(9)
_cell_angle_gamma                64.208(9)
_cell_formula_units_Z            2
_cell_length_a                   10.0753(11)
_cell_length_b                   10.3677(8)
_cell_length_c                   11.4126(13)
_cell_measurement_reflns_used    2050
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5040
_cell_measurement_theta_min      3.7420
_cell_volume                     1041.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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    -50.00  40.00   1.00    4.00    --   18.81 -57.00  90.00   90
  2  \w     44.00  91.00   1.00    4.00    --   18.81-178.00   0.00   47
  3  \w    -50.00  37.00   1.00    4.00    --   18.81 -57.00 -30.00   87
  4  \w    -36.00  51.00   1.00    4.00    --   18.81   0.00   0.00   87
  5  \w    -20.00  60.00   1.00    4.00    --   18.81 -99.00-150.00   80
  6  \w    -58.00 -21.00   1.00    4.00    --  -19.74  89.00  71.00   37
  7  \w    -25.00  10.00   1.00    4.00    --  -19.74 -89.00 -44.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0413930000
_diffrn_orient_matrix_UB_12      0.0061234000
_diffrn_orient_matrix_UB_13      -0.0560924000
_diffrn_orient_matrix_UB_21      -0.0478429000
_diffrn_orient_matrix_UB_22      0.0749191000
_diffrn_orient_matrix_UB_23      -0.0139745000
_diffrn_orient_matrix_UB_31      0.0463130000
_diffrn_orient_matrix_UB_32      0.0178567000
_diffrn_orient_matrix_UB_33      0.0276665000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7802
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         3.129
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0904
_refine_ls_R_factor_gt           0.0597
_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^)+(0.0851P)^2^+0.1577P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1468
_refine_ls_wR_factor_ref         0.1741
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2501
_reflns_number_total             3753
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02547_si_002.cif
_cod_data_source_block           20160619
_cod_depositor_comments          'Adding full bibliography for 4032144.cif.'
_cod_database_code               4032144
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C2 \\sim C2A \\sim C3 \\sim C3A \\sim C4 \\sim C4A: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=
 Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=1-FVAR(1)
 Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=Sof(C4)=
 Sof(H4A)=Sof(H4B)=Sof(H4C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C17(H17), C18(H18)
4.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16)
4.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C2A(H2AA,H2AB,H2AC), C3(H3A,H3B,H3C), C3A(H3AA,H3AB,H3AC),
 C4(H4A,H4B,H4C), C4A(H4AA,H4AB,H4AC), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_shelx_res_checksum              73365
_shelx_hkl_checksum              55292
_shelx_shelxl_version_number     2014/7
_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 1.372
_oxdiff_exptl_absorpt_empirical_full_min 0.725