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_7211322
_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         'C16 H18 O5'
_chemical_formula_sum            'C16 H18 O5'
_chemical_formula_weight         290.30
_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   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-17
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 107.285(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7243(11)
_cell_length_b                   5.0123(3)
_cell_length_c                   18.5815(12)
_cell_measurement_reflns_used    2283
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.4140
_cell_measurement_theta_min      3.2290
_cell_volume                     1398.36(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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 10.3613
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.9548
_diffrn_measurement_details
;
  1 omega  -38.00   24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000 -180.0000 62

  2 omega  -44.00   26.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   45.0000 -120.0000 70

  3 omega  -33.00   31.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000  -60.0000 64

  4 omega  -91.00  -63.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  125.0000   60.0000 28

  5 omega  132.00  161.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  125.0000 -180.0000 29

  6 omega   85.00  178.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472   30.0000  -90.0000 93

  7 omega   36.00   90.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000   90.0000 54

  8 omega   37.00   94.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -45.0000  -90.0000 57

  9 omega  126.00  174.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  114.0000   55.0000 48

 10 omega   42.00   67.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  120.0000 25

 11 omega   33.00   70.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472  -30.0000  150.0000 37

 12 omega   39.00   96.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      105.8472 -125.0000   60.0000 57
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova-Duo, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0124119000
_diffrn_orient_matrix_UB_12      0.0578073000
_diffrn_orient_matrix_UB_13      0.0839032000
_diffrn_orient_matrix_UB_21      0.1017703000
_diffrn_orient_matrix_UB_22      -0.0183051000
_diffrn_orient_matrix_UB_23      0.0162722000
_diffrn_orient_matrix_UB_31      0.0036068000
_diffrn_orient_matrix_UB_32      0.3015111000
_diffrn_orient_matrix_UB_33      -0.0150741000
_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  0.0207
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5181
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.350
_diffrn_reflns_theta_min         4.980
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_T_max  1.555
_exptl_absorpt_correction_T_min  1.146
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_description       lath
_exptl_crystal_F_000             616
_exptl_crystal_recrystallization_method
'crystallised by slow cooling of a hot cyclohexane solution'
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.0864
_exptl_crystal_size_min          0.0426
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0557P)^2^+0.2158P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1048
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2328
_reflns_number_total             2731
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3gc41477a.txt
_cod_data_source_block           lmcjmg
_cod_original_cell_volume        1398.35(17)
_cod_database_code               7211322
_nottingham_internal_coll_name   LMCJMG
_nottingham_internal_coll_number 12560
_nottingham_internal_coll_client LM/CJM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '3 and 12'
_nottingham_internal_coll_frame_width 1
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   14/6/2013
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user WL
_nottingham_internal_process_date 14/6/2013
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date 14/6/2013
_nottingham_internal_refinement_user WL
_nottingham_internal_refinement_date 14/6/2013
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 17/6/2013
_nottingham_internal_archive_date 17/6/2013
_chemical_oxdiff_formula         'C16 H18 O5'
_chemical_oxdiff_usercomment
'LMCJMG #12560 IN FOMBLIN FILM ON A MICROMOUNT FOR LM/CJM'
_reflns_odcompleteness_completeness 99.86
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C19(H19A,H19B,H19C)
;
_shelxl_version_number           2013-2