One-pot heteroannulation toward phosphaperylene diimides with high luminescence and out-of-plane anisotropy
Ma, Zetong; Liu, Yujian; Wang, Z.-H.; Jiang, Wei; Chemical Communications  (2022) –; doi:10.1039/D2CC04784E

data_7130831
_publ_section_title
;
 One-pot heteroannulation toward phosphaperylene diimides with high
 luminescence and out-of-plane anisotropy
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC04784E
_journal_year                    2022
_chemical_formula_moiety         '3(C H Cl3), C44 H18 F14 N2 O6 P2'
_chemical_formula_sum            'C47 H21 Cl9 F14 N2 O6 P2'
_chemical_formula_weight         1356.65
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-30 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.674(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   34.0447(12)
_cell_length_b                   5.7951(2)
_cell_length_c                   26.8127(10)
_cell_measurement_reflns_used    10007
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      1.909
_cell_volume                     5272.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9d (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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      223.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       '\w scans at fixed \c = 45\%'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            19483
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         1.862
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.640
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.70236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.9d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.709
_exptl_crystal_description       rod
_exptl_crystal_F_000             2696
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.117
_exptl_crystal_size_min          0.032
_refine_diff_density_max         1.142
_refine_diff_density_min         -0.678
_refine_diff_density_rms         0.100
_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     366
_refine_ls_number_reflns         6054
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1026
_refine_ls_R_factor_gt           0.0891
_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^)+(0.1532P)^2^+17.6398P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2578
_refine_ls_wR_factor_ref         0.2724
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4868
_reflns_number_total             6054
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04784e2.cif
_cod_data_source_block           mx7527e
_cod_database_code               7130831
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.772
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Rigid bond restraints
 P1, C13
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F5, C22
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Others
 Fixed Sof: C24(0.5) H24(0.5)
4.a Riding coordinates:
 C24(H24)
4.b Ternary CH refined with riding coordinates:
 C23(H23)
4.c Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B)
4.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C9(H9), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_shelx_res_checksum              9258
_shelx_hkl_checksum              61544
_olex2_submission_special_instructions 'No special instructions were received'