Solar photochemistry: optimisation of the photo Friedel–Crafts acylation of naphthoquinones
Mitchell, Lorna J.; Lewis, William; Moody, Christopher J.; Green Chemistry 15 (2013) 2830–; doi:10.1039/c3gc41477a

data_7211321
_publ_section_title
;
 Solar photochemistry: optimisation of the photo Friedel--Crafts acylation
 of naphthoquinones
;
_journal_issue                   10
_journal_name_full               'Green Chemistry'
_journal_page_first              2830
_journal_paper_doi               10.1039/c3gc41477a
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C15 H16 O4'
_chemical_formula_sum            'C15 H16 O4'
_chemical_formula_weight         260.28
_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'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-07-04
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.8287(3)
_cell_length_b                   7.9789(3)
_cell_length_c                   24.2643(9)
_cell_measurement_reflns_used    5510
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.2240
_cell_measurement_theta_min      3.6340
_cell_volume                     2483.67(14)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.6296
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.9961
_diffrn_measured_fraction_theta_max 0.9822
_diffrn_measurement_details
;
  1 omega  -46.00   28.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000    0.0000 74

  2 omega   18.00  105.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2573   57.0000  120.0000 87

  3 omega   30.00   75.00   1.0000  320.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -30.0000   90.0000 45

  4 omega   66.00  109.00   1.0000  320.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -94.0000  -60.0000 43

  5 omega   82.00  170.00   1.0000  320.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   45.0000    0.0000 88

  6 omega   30.00   89.00   1.0000  320.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -30.0000 -180.0000 59

  7 omega  133.00  172.00   1.0000  320.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   77.0000 -180.0000 39

  8 omega   10.00  112.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2573   77.0000 -120.0000 102

  9 omega  -28.00   65.00   1.0000   80.0000
omega____ theta____ kappa____ phi______ frames
    -       40.2573  -57.0000  120.0000 93

 10 omega   81.00  173.00   1.0000  320.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   45.0000  150.0000 92

 11 omega   63.00  167.00   1.0000  320.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526   15.0000  -90.0000 104

 12 omega   23.00  109.00   1.0000  320.0000
omega____ theta____ kappa____ phi______ frames
    -      103.2526  -94.0000  120.0000 86
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0989630000
_diffrn_orient_matrix_UB_12      -0.1015532000
_diffrn_orient_matrix_UB_13      -0.0133929000
_diffrn_orient_matrix_UB_21      0.0267683000
_diffrn_orient_matrix_UB_22      0.0080701000
_diffrn_orient_matrix_UB_23      -0.0618470000
_diffrn_orient_matrix_UB_31      0.0625415000
_diffrn_orient_matrix_UB_32      -0.1639833000
_diffrn_orient_matrix_UB_33      0.0052578000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.0371
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            13106
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.782
_diffrn_reflns_theta_min         3.643
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_T_max  1.018
_exptl_absorpt_correction_T_min  0.931
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.1243
_exptl_crystal_size_mid          0.0791
_exptl_crystal_size_min          0.0316
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0525
_refine_ls_R_factor_gt           0.0438
_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^)+(0.0636P)^2^+1.0941P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1191
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2126
_reflns_number_total             2494
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3gc41477a.txt
_cod_data_source_block           lmcjmm
_cod_original_cell_volume        2483.67(15)
_cod_database_code               7211321
_nottingham_internal_coll_name   LMCJMM
_nottingham_internal_coll_number 12611
_nottingham_internal_coll_client LM/CJM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '80 and 320s'
_nottingham_internal_coll_frame_width 1
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   28/6/2013
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user WL
_nottingham_internal_process_date 1/7/2013
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date 1/7/2013
_nottingham_internal_refinement_user WL
_nottingham_internal_refinement_date 1/7/2013
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 4/7/2013
_nottingham_internal_archive_date 4/7/2013
_chemical_oxdiff_formula         'C15 H16 O4'
_chemical_oxdiff_usercomment
'LMCJMM #12611 IN FOMBLIN FIML ON MICROMOUNT FOR LM/CJM'
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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, All C(H,H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C7(H7), C5(H5)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C14(H14A,H14B,H14C)
;
_shelxl_version_number           2013-2