A triphenylphosphine mediated photo-rearrangement and methanol addition of aryl chalcones to 1-propanones.
Sun, Qiu; Yao, Chang Jiang; König, Burkhard; Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology 14 (2015) 948–952; doi:10.1039/c5pp00009b

data_1518734
_publ_section_title
;
 A triphenylphosphine mediated photo-rearrangement and methanol addition
 of aryl chalcones to 1-propanones.
;
_journal_issue                   5
_journal_name_full
'Photochemical &amp; photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              948
_journal_page_last               952
_journal_paper_doi               10.1039/c5pp00009b
_journal_volume                  14
_journal_year                    2015
_chemical_formula_moiety         'C20 H18 O2'
_chemical_formula_sum            'C20 H18 O2'
_chemical_formula_weight         290.34
_chemical_name_systematic
'3-Methoxy-1-(naphthalen-2-yl)-2-phenylpropan-1-one '
_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_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2014-11-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.11.03 svn.r3071 for OlexSys, GUI svn.r4932)
;
_audit_update_record
;
2015-01-02 deposited with the CCDC.
2015-02-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.702(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7862(2)
_cell_length_b                   16.6613(3)
_cell_length_c                   11.1995(3)
_cell_measurement_reflns_used    5541
_cell_measurement_temperature    123.00(14)
_cell_measurement_theta_max      66.6040
_cell_measurement_theta_min      5.0100
_cell_volume                     1512.47(7)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2548
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
  1 omega  -80.00  -52.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5337  125.0000  -60.0000 56

  2 omega  -22.00   30.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5337  -57.0000 -150.0000 104

  3 omega    0.00   84.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5337  -19.0000  -90.0000 168

  4 omega   12.00   42.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000 -126.4386 60

  5 omega   90.00  118.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -62.0000  -53.4388 56

  6 omega   10.00   77.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000  -30.0000 134

  7 omega   39.00   66.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -62.0000  -53.4388 54

  8 omega   17.00   62.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000   90.0000 90

  9 omega   27.00   63.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000  -90.0000 72

 10 omega   16.00   66.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -30.0000  120.0000 100

 11 omega   51.00  132.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -90.0000 -126.4386 162

 12 omega   63.00  167.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   61.0000   30.0000 208

 13 omega   75.00  101.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000   -8.2617 52

 14 omega   14.00   84.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -95.0000   90.0000 140

 15 omega   10.00   36.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000  -92.0000   -8.2617 52

 16 omega -120.00   -8.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5337  -77.0000  120.0000 224

 17 omega   12.00  115.00   0.5000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5337   57.0000  -60.0000 206

 18 omega   66.00  142.00   0.5000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       93.5000   45.0000 -180.0000 152
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0396959000
_diffrn_orient_matrix_UB_12      -0.0885876000
_diffrn_orient_matrix_UB_13      -0.0151591000
_diffrn_orient_matrix_UB_21      0.0936965000
_diffrn_orient_matrix_UB_22      0.0257418000
_diffrn_orient_matrix_UB_23      -0.0850162000
_diffrn_orient_matrix_UB_31      0.1603829000
_diffrn_orient_matrix_UB_32      0.0068345000
_diffrn_orient_matrix_UB_33      0.1215988000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9385
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.821
_diffrn_reflns_theta_min         5.037
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92024
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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    1.275
_exptl_crystal_description       prism
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.2169
_exptl_crystal_size_mid          0.1561
_exptl_crystal_size_min          0.0931
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0356
_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^)+(0.0476P)^2^+0.3817P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0957
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2406
_reflns_number_total             2658
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5pp00009b2.cif
_cod_data_source_block           n111
_cod_depositor_comments          'Adding full bibliography for 1518734.cif.'
_cod_database_code               1518734
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C20 H18 O2'
_reflns_odcompleteness_completeness 98.47
_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 C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C12(H12), C5(H5), C9(H9), C20(H20), C8(H8), C7(H7), C13(H13),
 C6(H6), C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              96784
_olex2_diffrn_ambient_temperature_device 'Oxford Instruments CryoJet'
_olex2_submission_special_instructions 'No special instructions were received'