Investigations on photochromic properties of 2,6-bis(5-bromo-2-hydroxybenzylidene)cyclohexanone
Corici, Livia; Sova, Sergiu; Badea, Valentin; Aparaschivei, Diana; Costisor, Otilia; Cseh, Liliana; Photochem. Photobiol. Sci.  (2017) –; doi:10.1039/C6PP00466K

data_1545696
_publ_section_title
;
 Investigations on photochromic properties of
 2,6-bis(5-bromo-2-hydroxybenzylidene)cyclohexanone
;
_journal_name_full               'Photochem. Photobiol. Sci.'
_journal_paper_doi               10.1039/C6PP00466K
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H15 Br2 O2, Cl O4, 0.38(H2 O)'
_chemical_formula_sum            'C20 H15.75 Br2 Cl O6.38'
_chemical_formula_weight         553.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-12-15
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2016-12-15 deposited with the CCDC.
2017-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.184(5)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2991(6)
_cell_length_b                   20.2762(12)
_cell_length_c                   15.0236(7)
_cell_measurement_reflns_used    6178
_cell_measurement_temperature    200.00(14)
_cell_measurement_theta_max      20.9590
_cell_measurement_theta_min      1.5510
_cell_volume                     4050.3(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(14)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0797
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_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    -76.00 -35.00   1.00  100.00    --  -15.60-178.00  60.00   41
  2  \w    -16.00  23.00   1.00  100.00    --  -15.60 -99.00  60.00   39
  3  \w      2.00  54.00   1.00  100.00    --   17.79  57.00-180.00   52
  4  \w      0.00  28.00   1.00  100.00    --   17.79  19.00 120.00   28
  5  \w     35.00  89.00   1.00  100.00    --   17.79  19.00 120.00   54
  6  \w     -7.00  73.00   1.00  100.00    --   17.79  77.00-120.00   80
  7  \w     10.00  85.00   1.00  100.00    --   17.79  57.00  30.00   75
  8  \w      8.00  67.00   1.00  100.00    --   17.79  57.00 -30.00   59
  9  \w     22.00  54.00   1.00  100.00    --   17.79 -99.00 150.00   32
 10  \w    -44.00  13.00   1.00  100.00    --   17.79 -77.00 150.00   57
 11  \w    -51.00  24.00   1.00  100.00    --   17.79 -38.00  30.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0202776000
_diffrn_orient_matrix_UB_12      -0.0067606000
_diffrn_orient_matrix_UB_13      0.0430817000
_diffrn_orient_matrix_UB_21      -0.0474267000
_diffrn_orient_matrix_UB_22      -0.0121047000
_diffrn_orient_matrix_UB_23      0.0133122000
_diffrn_orient_matrix_UB_31      0.0136250000
_diffrn_orient_matrix_UB_32      -0.0320996000
_diffrn_orient_matrix_UB_33      -0.0140754000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_unetI/netI     0.1035
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            37527
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        23.256
_diffrn_reflns_theta_max         23.256
_diffrn_reflns_theta_min         1.532
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    4.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear dark brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_description       prism
_exptl_crystal_F_000             2190
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.789
_refine_diff_density_min         -1.034
_refine_diff_density_rms         0.122
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.31(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1034
_refine_ls_number_reflns         11580
_refine_ls_number_restraints     162
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1335
_refine_ls_R_factor_gt           0.0759
_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^)+(0.1087P)^2^+3.7554P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1755
_refine_ls_wR_factor_ref         0.2089
_reflns_Friedel_coverage         0.937
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                7177
_reflns_number_total             11580
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6pp00466k2.cif
_cod_data_source_block           shi_3355_lics
_cod_original_cell_volume        4050.3(3)
_cod_database_code               1545696
_chemical_oxdiff_formula         'C20 H20 O2 Br2 Cl2'
_chemical_oxdiff_usercomment     Br_AH
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.69(2) 0.31(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
3. Restrained distances
 O12X-O10X \\sim O9X-O11X \\sim O10X-O9X \\sim O12X-O9X \\sim O11X-O12X \\sim
O11X-O10X
 with sigma of 0.01
 Cl11-O12X \\sim Cl11-O10X \\sim Cl11-O11X \\sim Cl11-O9X
 with sigma of 0.01
 Cl10-O15 \\sim Cl10-O16 \\sim Cl10-O14 \\sim Cl10-O13
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C17C) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C15C) \\sim Ueq, Uanis(C19A) \\sim Ueq, Uanis(C15A) \\sim Ueq, Uanis(C4D)
\\sim Ueq, Uanis(C13D) \\sim Ueq, Uanis(C4C) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C12C) \\sim Ueq, Uanis(C13C) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C1D) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uiso(Cl11)
Uiso(Cl11) = Uiso(O9X) = Uiso(O10X) = Uiso(O11X) = Uiso(O12X)
Uiso(O15) = Uiso(O16) = Uiso(O14) = Uiso(O13)
5. Others
 Fixed Sof: O13X(0.5) O14(0.5) O15X(0.5) O16X(0.5) O13(0.5) O14X(0.5) O15(0.5)
 O16(0.5) Cl(0.75) O9(0.75) O10(0.75) O11(0.75) O12(0.75) Cl11(0.25) O9X(0.25)
 O10X(0.25) O11X(0.25) O12X(0.25) O1W(0.6) H1WA(0.6) H1WB(0.6) O3W(0.4)
 H3WA(0.4) H3WB(0.4) O2W(0.5) H2WA(0.5) H2WB(0.5)
6.a Riding coordinates:
 O2A(H2A), O2C(H2C), O2B(H2B), O1W(H1WA,H1WB), O3W(H3WA,H3WB)
6.b Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C7A(H7A), C6C(H6C), C3B(H3B), C6B(H6B), C7B(H7B), C2D(H2DA),
 C3D(H3D), C6D(H6D), C7D(H7D)
6.c Idealised tetrahedral OH refined as rotating group:
 O2D(H2D)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-12-07
_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 2.164
_oxdiff_exptl_absorpt_empirical_full_min 0.752