Stereoselective Intermolecular [2 + 2] Cycloadditions of Erlenmeyer-Plöchl Azlactones Using Visible Light Photoredox Catalysis.
Marra, Isabellar F. S.; de Almeida, Angelina M.; Silva, Larissa P.; de Castro, Pedro P.; Corrêa, Charlane C; Amarante, Giovanni Wilson; The Journal of organic chemistry 83 (2018) 15144–15154; doi:10.1021/acs.joc.8b02430

data_4034737
_publ_section_title
;
 Stereoselective Intermolecular [2 + 2] Cycloadditions of
 Erlenmeyer-Pl\"ochl Azlactones Using Visible Light Photoredox Catalysis.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              15144
_journal_page_last               15154
_journal_paper_doi               10.1021/acs.joc.8b02430
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C33 H24 Cl2 N2 O5'
_chemical_formula_sum            'C33 H24 Cl2 N2 O5'
_chemical_formula_weight         599.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.820(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.0644(8)
_cell_length_b                   18.8372(7)
_cell_length_c                   13.6807(5)
_cell_measurement_reflns_used    4178
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      71.3570
_cell_measurement_theta_min      4.1490
_cell_volume                     6344.4(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2923
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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    -59.00  31.00   1.00   30.00    --  -40.85  38.00 -60.00   90
  2  \w    -64.00  24.00   1.00   30.00    --  -40.85  38.00-150.00   88
  3  \w     56.00  84.00   1.00   30.00    --   40.85-125.00 -90.00   28
  4  \w     30.00 111.00   1.00  150.00    --  103.96-111.00   0.00   81
  5  \w     53.00 108.00   1.00  150.00    --  103.96 -94.00  60.00   55
  6  \w     76.00 170.00   1.00  150.00    --  103.96  30.00  90.00   94
  7  \w    106.00 170.00   1.00  150.00    --  103.96 111.00   0.00   64
  8  \w     68.00 128.00   1.00  150.00    --  103.96 -45.00  90.00   60
  9  \w    121.00 166.00   1.00  150.00    --  103.96 111.00-120.00   45
 10  \w    117.00 151.00   1.00  150.00    --  103.96 111.00 120.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0086307000
_diffrn_orient_matrix_UB_12      0.0683503000
_diffrn_orient_matrix_UB_13      0.0568226000
_diffrn_orient_matrix_UB_21      0.0124377000
_diffrn_orient_matrix_UB_22      0.0447954000
_diffrn_orient_matrix_UB_23      -0.0872589000
_diffrn_orient_matrix_UB_31      -0.0607443000
_diffrn_orient_matrix_UB_32      -0.0005034000
_diffrn_orient_matrix_UB_33      -0.0480839000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11606
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.548
_diffrn_reflns_theta_max         67.548
_diffrn_reflns_theta_min         4.667
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.177
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       needle
_exptl_crystal_F_000             2480
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.042
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         5702
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0675
_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^)+(0.1119P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1845
_refine_ls_wR_factor_ref         0.2117
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4101
_reflns_number_total             5702
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02430_si_002.cif
_cod_data_source_block           isabela_cu_n2_c
_cod_database_code               4034737
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C33 H24 Cl2 N2 O5'
_shelx_estimated_absorpt_t_max   0.920
_shelx_estimated_absorpt_t_min   0.730
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C12(H12), C30(H30), C18(H18), C4(H4), C20(H20), C29(H29), C32(H32),
 C3(H3), C31(H31), C17(H17), C15(H15), C16(H16), C24(H24), C21(H21), C6(H6),
 C22(H22), C1(H1), C23(H23)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_shelx_res_checksum              64459
_shelx_hkl_checksum              48710
_shelx_fab_checksum              41726
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.181
_oxdiff_exptl_absorpt_empirical_full_min 0.253