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_7130832
_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         'C H2 Cl2, C44 H18 F14 N2 O6 P2'
_chemical_formula_sum            'C45 H20 Cl2 F14 N2 O6 P2'
_chemical_formula_weight         1083.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-09-21
_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                 97.757(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.5562(11)
_cell_length_b                   11.4446(5)
_cell_length_c                   20.8876(13)
_cell_measurement_reflns_used    6123
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5120
_cell_measurement_theta_min      1.9580
_cell_volume                     4158.4(4)
_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  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0863
_diffrn_reflns_av_unetI/netI     0.1124
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            30262
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_min         1.968
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75058
_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    1.731
_exptl_crystal_description       plate
_exptl_crystal_F_000             2168
_exptl_crystal_size_max          0.128
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     704
_refine_ls_number_reflns         9502
_refine_ls_number_restraints     228
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.1553
_refine_ls_R_factor_gt           0.0762
_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^)+(0.0811P)^2^+1.4553P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.2013
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5013
_reflns_number_total             9502
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc04784e2.cif
_cod_data_source_block           mx7518a
_cod_database_code               7130832
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.956
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F7 \\sim C39 \\sim C40
\\sim F1A \\sim F2A \\sim F4A \\sim F3A \\sim F5A \\sim F7A \\sim F6A: within
1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim
Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(C40)
\\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F4A) \\sim Ueq,
Uanis(F5A) \\sim Ueq, Uanis(F7A) \\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F3A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(F1A)=Sof(F2A)=Sof(F4A)=Sof(F3A)=Sof(F5A)=Sof(F7A)=Sof(F6A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=Sof(F7)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C45(H45A,H45B), C37(H37A,H37B), C41(H41A,H41B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C14(H14), C19(H19), C26(H26), C27(H27), C28(H28), C29(H29),
 C30(H30), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
;
_shelx_res_checksum              80511
_shelx_hkl_checksum              74540
_olex2_submission_special_instructions 'No special instructions were received'