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_7211320
_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 O4'
_chemical_formula_sum            'C16 H18 O4'
_chemical_formula_weight         274.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-06-07
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 114.189(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7968(2)
_cell_length_b                   21.1512(5)
_cell_length_c                   9.1046(3)
_cell_measurement_reflns_used    6647
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.1530
_cell_measurement_theta_min      4.1720
_cell_volume                     1369.63(7)
_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
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
;
_computing_data_reduction
;
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 0.9996
_diffrn_measured_fraction_theta_max 0.9852
_diffrn_measurement_details
;
  1 omega  -43.00  -18.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000   30.0000 25

  2 omega  -10.00   77.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       39.1804  -99.0000 -180.0000 87

  3 omega  -32.00   60.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       39.1804  -38.0000  -90.0000 92

  4 omega   31.00   63.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      102.8295  -30.0000 -180.0000 32

  5 omega   44.00   94.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      102.8295  -45.0000 -150.0000 50

  6 omega   41.00   87.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      102.8295  -45.0000  120.0000 46

  7 omega   68.00  150.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      102.8295   15.0000    0.0000 82

  8 omega  124.00  150.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      102.8295   77.0000   60.0000 26

  9 omega   60.00   86.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      102.8295 -125.0000  150.0000 26

 10 omega   97.00  122.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      102.8295 -125.0000  150.0000 25

 11 omega   30.00   90.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      102.8295  -30.0000    0.0000 60

 12 omega   30.00   87.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      102.8295  -30.0000   60.0000 57

 13 omega   14.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       39.1804   57.0000  -30.0000 94

 14 omega    9.00  111.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       39.1804   77.0000   30.0000 102

 15 omega   14.00  108.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -       39.1804   57.0000 -120.0000 94

 16 omega   82.00  176.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      102.8295   30.0000   60.0000 94

 17 omega   23.00  109.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      102.8295  -94.0000  -30.0000 86

 18 omega   82.00  176.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      102.8295   30.0000 -120.0000 94

 19 omega   77.00  163.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      102.8295   61.0000   90.0000 86

 20 omega   31.00  133.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      102.8295  -77.0000  120.0000 102

 21 omega   80.00  172.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      102.8295   45.0000  150.0000 92
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.1898122000
_diffrn_orient_matrix_UB_12      0.0081722000
_diffrn_orient_matrix_UB_13      0.0126279000
_diffrn_orient_matrix_UB_21      0.0880770000
_diffrn_orient_matrix_UB_22      0.0504799000
_diffrn_orient_matrix_UB_23      0.1315420000
_diffrn_orient_matrix_UB_31      -0.0560162000
_diffrn_orient_matrix_UB_32      0.0518452000
_diffrn_orient_matrix_UB_33      -0.1302604000
_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  0.0185
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12604
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.564
_diffrn_reflns_theta_min         4.180
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.779
_exptl_absorpt_correction_T_max  1.043
_exptl_absorpt_correction_T_min  0.955
_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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       tablet
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method
'crystallised by vapour diffusion of cyclohexane into an ethyl acetate solution of the compound'
_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.1016
_exptl_crystal_size_min          0.0629
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0329
_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^)+(0.0498P)^2^+0.3480P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0941
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2433
_reflns_number_total             2766
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3gc41477a.txt
_cod_data_source_block           lmcjma
_cod_original_cell_volume        1369.64(7)
_cod_database_code               7211320
_nottingham_internal_coll_name   LMCJMA
_nottingham_internal_coll_number 12543
_nottingham_internal_coll_client LM/CJM
_nottingham_internal_coll_type   CUSTOM
_nottingham_internal_coll_frame_time '10 and 40'
_nottingham_internal_coll_frame_width 1
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   6/06/2012
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user WL
_nottingham_internal_process_date 7/06/2013
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date 7/06/2013
_nottingham_internal_refinement_user WL
_nottingham_internal_refinement_date 7/06/2013
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 7/6/2013
_nottingham_internal_archive_date 7/6/2013
_chemical_oxdiff_formula         'C16 H18 O4'
_chemical_oxdiff_usercomment
'LMCJMA #12543 IN FOMBLIN FILM ON MICROMOUNT FOR LM/CJM'
_reflns_odcompleteness_completeness 99.96
_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), C5(H5), C6(H6), C7(H7)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O9(H9), O15(H15)
;
_shelxl_version_number           2013-2