Crystalline-state chemiluminescence reactions of two-fluorophore-linked adamantylideneadamantane 1,2-dioxetane isomers accompanied by solid-to-solid phase transitions
Matsuhashi, Chihiro; Oyama, Hironaga; Uekusa, Hidehiro; Sato-Tomita, Ayana; Ichiyanagi, Kouhei; Maki, Shojiro A.; Hirano, Takashi; CrystEngComm  (2022) –; doi:10.1039/D2CE00266C

data_7244772
_publ_section_title
;
 Crystalline-state chemiluminescence reactions of two-fluorophore-linked
 adamantylideneadamantane 1,2-dioxetane isomers accompanied by
 solid-to-solid phase transitions
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D2CE00266C
_journal_year                    2022
_chemical_formula_moiety         'C34 H28 F3 N O6'
_chemical_formula_sum            'C34 H28 F3 N O6'
_chemical_formula_weight         603.57
_chemical_melting_point          468.5(5)
_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             2021-12-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_audit_update_record
;
2021-12-15 deposited with the CCDC.	2022-04-08 downloaded from the CCDC.
;
_cell_angle_alpha                108.781(7)
_cell_angle_beta                 101.858(6)
_cell_angle_gamma                105.672(6)
_cell_formula_units_Z            2
_cell_length_a                   7.4930(4)
_cell_length_b                   13.8284(10)
_cell_length_c                   15.4815(13)
_cell_measurement_reflns_used    5323
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      29.9620
_cell_measurement_theta_min      2.6650
_cell_volume                     1385.0(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.835
_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    -90.00 -63.00   0.50   80.77    --   -4.30  45.00  60.00   54
  2  \w    -92.00  84.00   0.50   80.77    --   -4.30  45.00 150.00  352
  3  \w     38.00  65.00   0.50   80.77    --   -4.30  45.00  60.00   54
  4  \w    -24.00  46.00   0.50   80.77    --   -4.30  45.00   0.00  140
  5  \w    -37.00 -10.00   0.50   80.77    --   -4.30  45.00  60.00   54
  6  \w    -41.00 -14.00   0.50   80.77    --    4.30  45.00  30.00   54
  7  \w    -84.00  90.00   0.50   80.77    --    4.30  45.00  90.00  348
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RINC): fixed-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1015902000
_diffrn_orient_matrix_UB_12      0.0302602000
_diffrn_orient_matrix_UB_13      0.0235582000
_diffrn_orient_matrix_UB_21      0.0167139000
_diffrn_orient_matrix_UB_22      -0.0494607000
_diffrn_orient_matrix_UB_23      -0.0057388000
_diffrn_orient_matrix_UB_31      0.0132465000
_diffrn_orient_matrix_UB_32      -0.0042980000
_diffrn_orient_matrix_UB_33      -0.0449736000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0550
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.835
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25797
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.835
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.357
_diffrn_reflns_theta_min         2.627
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Mo) X-ray DW Source'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.35a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       plate
_exptl_crystal_F_000             628
_exptl_crystal_preparation       Luminescent
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: n-Hexane / dichloromethane'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     426
_refine_ls_number_reflns         6970
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0849
_refine_ls_R_factor_gt           0.0645
_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^)+(0.0981P)^2^+0.4513P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1607
_refine_ls_wR_factor_ref         0.1732
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5449
_reflns_number_total             6970
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ce00266c4.cif
_cod_data_source_block           cm-ii-108-2_autored
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '468-469' was changed to
'468.5(5)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_cell_volume        1384.96(19)
_cod_database_code               7244772
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C34H28F3NO6
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.952
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Others
 Sof(F2B)=Sof(F3A)=Sof(F1B)=1-FVAR(1)
 Sof(F3B)=Sof(F2A)=Sof(F1A)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C29(H29), C27(H27), C32(H32)
3.b Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B), C26(H26A,H26B), C23(H23A,H23B), C31(H31A,H31B), C33(H33A,
 H33B), C34(H34A,H34B)
3.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C17(H17), C3(H3), C6(H6), C12(H12), C14(H14), C7(H7), C21(H21),
 C20(H20), C15(H15)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              43256
_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 1.434
_oxdiff_exptl_absorpt_empirical_full_min 0.726