Wavelength Dependent Photoextrusion and Tandem Photoextrusion Reactions of Ninhydrin bis-Acetals for the Synthesis of 8-Ring Lactones, Benzocyclobutenes and Orthoanhydrides.
Harrowven, David; Sun, Wei; Kayal, Surajit; Raimbach, William; Sun, Xue-Zhong; Light, Mark E.; Hanson-Heine, Magnus W.D.; George, Michael W.; Chemical Communications  (2022) –; doi:10.1039/D1CC06800H

data_7129462
_publ_section_title
;
 Wavelength Dependent Photoextrusion and Tandem Photoextrusion Reactions
 of Ninhydrin bis-Acetals for the Synthesis of 8-Ring Lactones,
 Benzocyclobutenes and Orthoanhydrides.
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06800H
_journal_year                    2022
_chemical_formula_moiety         'C15 H16 O5'
_chemical_formula_sum            'C15 H16 O5'
_chemical_formula_weight         276.28
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-04-09 deposited with the CCDC.	2021-12-23 downloaded from the CCDC.
;
_cell_angle_alpha                88.072(2)
_cell_angle_beta                 65.610(3)
_cell_angle_gamma                66.567(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1160(3)
_cell_length_b                   9.3511(3)
_cell_length_c                   9.7170(3)
_cell_measurement_reflns_used    14192
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.5530
_cell_measurement_theta_min      4.0980
_cell_volume                     683.68(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.18b (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_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   -109.00  17.00   1.00    1.00    --  -19.30 -60.00 150.00  126
  2  \w   -109.00  17.00   1.00    1.00    --  -19.30 -60.00  30.00  126
  3  \w    -56.00  70.00   1.00    1.00    --  -19.30  60.00-120.00  126
  4  \w    -56.00  70.00   1.00    1.00    --  -19.30  60.00  30.00  126
  5  \w    -56.00  70.00   1.00    1.00    --  -19.30  60.00 120.00  126
  6  \w   -109.00  17.00   1.00    1.00    --  -19.30 -60.00 -90.00  126
  7  \w    -56.00  70.00   1.00    1.00    --  -19.30  60.00 -30.00  126
  8  \w   -109.00  16.00   1.00    1.00    --  -19.30 -57.00 -60.00  125
  9  \w    -56.00  38.00   1.00    1.00    --  -19.30  60.00  60.00   94
 10  \w    -56.00  70.00   1.00    1.00    --  -19.30  60.00-180.00  126
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0324624000
_diffrn_orient_matrix_UB_12      0.0276409000
_diffrn_orient_matrix_UB_13      0.0785702000
_diffrn_orient_matrix_UB_21      0.0148783000
_diffrn_orient_matrix_UB_22      -0.0776428000
_diffrn_orient_matrix_UB_23      0.0165145000
_diffrn_orient_matrix_UB_31      0.0871878000
_diffrn_orient_matrix_UB_32      -0.0145944000
_diffrn_orient_matrix_UB_33      -0.0117732000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            20674
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.498
_diffrn_reflns_theta_min         3.050
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.18b (Rigaku Oxford Diffraction, 2018)
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    1.342
_exptl_crystal_description       prism
_exptl_crystal_F_000             292
_exptl_crystal_recrystallization_method
'The material was recrystallised from DCM by slow evaporation'
_exptl_crystal_size_max          0.592
_exptl_crystal_size_mid          0.401
_exptl_crystal_size_min          0.169
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0366
_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^)+(0.0481P)^2^+0.2268P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0960
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3335
_reflns_number_total             3457
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc06800h2.cif
_cod_data_source_block           2019sot0006_k1_100k
_cod_original_cell_volume        683.68(4)
_cod_database_code               7129462
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'C15 H16 O5'
_chemical_oxdiff_usercomment     SW/8311/143
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 95.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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 Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C4(H4A,H4B,H4C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_shelx_res_checksum              56704
_olex2_date_sample_data_collection 2019-04-01
_olex2_date_sample_submission    2019-03-25
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder silicon oil'
_olex2_submission_original_sample_id SW/8311/143
_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 1.532
_oxdiff_exptl_absorpt_empirical_full_min 0.589