Photosensitised Regioselective [2+2]-Cycloaddition of Cinnamates and related Alkenes
Pagire, Santosh K.; Hossain, Asik; Traub, Lukas; Kerres, Sabine; Reiser, Oliver; Chem. Commun.  (2017) –; doi:10.1039/C7CC06710K

data_7120749
_publ_section_title
;
 Photosensitised Regioselective [2+2]-Cycloaddition of Cinnamates and
 related Alkenes
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC06710K
_journal_year                    2017
_chemical_formula_moiety         'C30 H24 O2'
_chemical_formula_sum            'C30 H24 O2'
_chemical_formula_weight         416.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_date             2016-12-13
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-08-25 deposited with the CCDC.
2017-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.349(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8157(1)
_cell_length_b                   9.5942(1)
_cell_length_c                   21.1289(2)
_cell_measurement_reflns_used    27386
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      73.4240
_cell_measurement_theta_min      4.0690
_cell_volume                     2191.90(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.42b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1773
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9993
_diffrn_measured_fraction_theta_max 0.9861
_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     14.00 117.00   1.00    1.50    --   40.71  37.00  30.00  103
  2  \w     14.00 117.00   1.00    1.50    --   40.71  37.00-120.00  103
  3  \w      2.00  98.00   1.00    1.50    --   40.71-125.00   0.00   96
  4  \w     11.00 115.00   1.00    1.50    --   40.71  57.00 120.00  104
  5  \w      2.00  98.00   1.00    1.50    --   40.71-125.00 150.00   96
  6  \w      8.00  46.00   1.00    1.50    --   42.00  80.00 -29.60   38
  7  \w      5.00  33.00   1.00    1.50    --   42.00  88.00-175.82   28
  8  \w      3.00  29.00   1.00    1.50    --   42.00  91.00 -83.17   26
  9  \w     10.00  36.00   1.00    1.50    --   46.00  85.00  77.68   26
 10  \w     19.00  45.00   1.00    1.50    --   54.00  82.00 -23.76   26
 11  \w     20.00  46.00   1.00    1.50    --   54.00  80.00-129.39   26
 12  \w     19.00  45.00   1.00    1.50    --   54.00  82.00 125.57   26
 13  \w     19.00  45.00   1.00    1.50    --   54.00  82.00 -78.55   26
 14  \w     25.00 136.00   1.00    1.50    --   58.00  76.00 -96.07  111
 15  \w     32.00 145.00   1.00    1.50    --   66.00  77.00 162.96  113
 16  \w     33.00 144.00   1.00    1.50    --   66.00  76.00 -88.29  111
 17  \w     32.00 145.00   1.00    1.50    --   66.00  77.00  13.79  113
 18  \w     33.00 144.00   1.00    1.50    --   66.00  75.00  82.23  111
 19  \w     37.00 148.00   1.00    1.50    --   70.00  76.00 -29.90  111
 20  \w     37.00 148.00   1.00    1.50    --   70.00  75.00-168.73  111
 21  \w     36.00 149.00   1.00    1.50    --   70.00  77.00  94.75  113
 22  \w     37.00 148.00   1.00    1.50    --   70.00  75.00 -67.03  111
 23  \w     38.00 146.00   1.00    1.50    --   70.00  71.00 122.41  108
 24  \w     40.00 153.00   1.00   12.00    --   74.00  77.00  22.23  113
 25  \w     32.00 121.00   1.00   12.00    --  106.98-125.00 -60.00   89
 26  \w     73.00 158.00   1.00   12.00    --  106.98  77.00-150.00   85
 27  \w     32.00  77.00   1.00   12.00    --  106.98 -45.00  60.00   45
 28  \w     77.00 158.00   1.00   12.00    --  106.98  61.00-150.00   81
 29  \w     23.00 109.00   1.00   12.00    --  106.98 -94.00  30.00   86
 30  \w     73.00 158.00   1.00   12.00    --  106.98  77.00   0.00   85
 31  \w     23.00 109.00   1.00   12.00    --  106.98 -94.00 -30.00   86
 32  \w     73.00 158.00   1.00   12.00    --  106.98  77.00-180.00   85
 33  \w     23.00 109.00   1.00   12.00    --  106.98 -94.00 -60.00   86
 34  \w     33.00 137.00   1.00   12.00    --  106.98 -61.00 120.00  104
 35  \w     73.00 158.00   1.00   12.00    --  106.98  77.00  60.00   85
 36  \w     23.00 109.00   1.00   12.00    --  106.98 -94.00  90.00   86
 37  \w     73.00 158.00   1.00   12.00    --  106.98  77.00 -30.00   85
 38  \w     73.00 158.00   1.00   12.00    --  106.98  77.00-120.00   85
 39  \w     73.00 158.00   1.00   12.00    --  106.98  77.00 120.00   85
 40  \w     32.00  77.00   1.00   12.00    --  106.98 -45.00   0.00   45
 41  \w     73.00 158.00   1.00   12.00    --  106.98  77.00  30.00   85
 42  \w     32.00  77.00   1.00   12.00    --  106.98 -45.00 -60.00   45
 43  \w     73.00 158.00   1.00   12.00    --  106.98  77.00 -60.00   85
 44  \w     73.00 154.00   1.00   12.00    --  106.98  77.00 150.00   81
 45  \w     76.00 121.00   1.00   12.00    --  106.98-125.00-180.00   45
 46  \w     73.00 149.00   1.00   12.00    --  106.98  77.00  90.00   76
 47  \w     73.00 154.00   1.00   12.00    --  106.98  77.00 -90.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0689314000
_diffrn_orient_matrix_UB_12      -0.0672327000
_diffrn_orient_matrix_UB_13      0.0568380000
_diffrn_orient_matrix_UB_21      0.0364259000
_diffrn_orient_matrix_UB_22      0.1456901000
_diffrn_orient_matrix_UB_23      0.0247790000
_diffrn_orient_matrix_UB_31      -0.1192860000
_diffrn_orient_matrix_UB_32      0.0056340000
_diffrn_orient_matrix_UB_33      0.0383883000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            49002
_diffrn_reflns_theta_full        73.5881
_diffrn_reflns_theta_max         73.59
_diffrn_reflns_theta_min         4.09
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.606
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.42b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2621
_exptl_crystal_description       prism
_exptl_crystal_F_000             882.6194
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.074
_refine_diff_density_max         0.2557
_refine_diff_density_min         -0.1984
_refine_diff_density_rms         0.0346
_refine_ls_d_res_high            0.8037
_refine_ls_d_res_low             10.8127
_refine_ls_goodness_of_fit_ref   1.0479
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    48
_refine_ls_number_parameters     288
_refine_ls_number_reflns         4378
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0479
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0391P)^2^+0.7255P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0849
_refine_ls_wR_factor_ref         0.0873
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              13
_reflns_limit_h_min              -12
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                4034
_reflns_number_total             4378
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c7cc06710k2.cif
_cod_data_source_block           P196
_cod_database_code               7120749
_chemical_oxdiff_formula         'C30 H20 O2'
_chemical_oxdiff_usercomment     Papire_Reiser_PC-96
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C2(H2), C4(H4), C11(H11)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C20(H20), C24(H24), C23(H23), C13(H13), C9(H9), C17(H17),
 C7(H7), C26(H26), C15(H15), C8(H8), C30(H30), C16(H16), C22(H22), C14(H14),
 C21(H21), C29(H29), C28(H28), C27(H27)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems CryoStream 700'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder with inert oil'
_olex2_submission_original_sample_id PC-96
_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 1.354
_oxdiff_exptl_absorpt_empirical_full_min 0.823