Circularly polarized chemiluminescence from planarly chiral bis(adamantylidene-1,2-dioxetane)s
Shi, Minglin; Xie, Mo; Wan, Shigang; Zou, Chao; Liu, Yuliang; Zhou, Xinyan; Yang, Peng; Chang, Xiaoyong; Lu, Wei; Chemical Communications  (2023) –; doi:10.1039/D3CC03389A

data_7132032
_publ_section_title
;
 Circularly polarized chemiluminescence from planarly chiral
 bis(adamantylidene-1,2-dioxetane)s
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03389A
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H26 Cl2 O6'
_chemical_formula_sum            'C36 H26 Cl2 O6'
_chemical_formula_weight         625.47
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-08-07 deposited with the CCDC.	2023-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2696(4)
_cell_length_b                   19.8223(11)
_cell_length_c                   20.3510(11)
_cell_measurement_reflns_used    9837
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.37
_cell_measurement_theta_min      3.11
_cell_volume                     2932.6(3)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'APEX 3 (Bruker 2021)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26930
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.384
_diffrn_reflns_theta_min         3.112
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.055
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.395
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6014
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1055 before and 0.0653 after correction.
The Ratio of minimum to maximum transmission is 0.7986.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details
;
 Flack x determined using 2227 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     401
_refine_ls_number_reflns         5386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0281
_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^)+(0.0380P)^2^+0.9302P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0728
_refine_ls_wR_factor_ref         0.0732
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                5280
_reflns_number_total             5386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03389a2.cif
_cod_data_source_block           cxy3235_0m
_cod_database_code               7132032
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.621
_shelx_estimated_absorpt_t_min   0.488
_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:
 C11(H11A,H11B), C12(H12A,H12B), C28(H28A,H28B), C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4A), C5(H5A), C14(H14), C26(H26), C31(H31), C32(H32), C33(H33), C34(H34),
 C35(H35), C36(H36)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C23(H23A,H23B,H23C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_shelx_res_checksum              86
_shelx_hkl_checksum              40691
_olex2_submission_special_instructions 'No special instructions were received'