Unusual [4+2] Fusion Strategy to Forge meso-N/O-Heteroarene-Fused (Quinoidal) Porphyrins with Intense Near-Infrared Q-Bands
Li, Chengming; Zhu, Lei; Liang, Wenbo; Su, Rongchuan; Yin, Jiangliang; Hu, Yanmei; Lan, Yu; Wu, Di; You, Jingsong; Chemical Science  (2019) –; doi:10.1039/C9SC01596E

data_1551472
_publ_section_title
;
 Unusual [4+2] Fusion Strategy to Forge meso-N/O-Heteroarene-Fused
 (Quinoidal) Porphyrins with Intense Near-Infrared Q-Bands
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/C9SC01596E
_journal_year                    2019
_chemical_formula_moiety         'C64 H40 F4 N4 O3 Zn'
_chemical_formula_sum            'C64 H40 F4 N4 O3 Zn'
_chemical_formula_weight         1054.37
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-07-24 deposited with the CCDC.    2019-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                102.982(7)
_cell_angle_beta                 94.647(6)
_cell_angle_gamma                95.015(7)
_cell_formula_units_Z            2
_cell_length_a                   13.4252(11)
_cell_length_b                   14.2425(13)
_cell_length_c                   14.4941(9)
_cell_measurement_reflns_used    2214
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9340
_cell_measurement_theta_min      3.2270
_cell_volume                     2675.7(4)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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    -23.00  22.50   0.70  150.00    --  -14.81 -99.00 120.00   65
  2  \w    -50.00  40.30   0.70  150.00    --   16.53 -77.00 -30.00  129
  3  \w    -10.00  77.50   0.70  150.00    --   16.53  77.00-120.00  125
  4  \w    -41.00  32.50   0.70  150.00    --   16.53 -38.00 -30.00  105
  5  \w      8.00  80.10   0.70  150.00    --   16.53  38.00 120.00  103
  6  \w     50.00  76.60   0.70  150.00    --   16.53  38.00 150.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0093327000
_diffrn_orient_matrix_UB_12      0.0253970000
_diffrn_orient_matrix_UB_13      0.0484349000
_diffrn_orient_matrix_UB_21      0.0042403000
_diffrn_orient_matrix_UB_22      -0.0444470000
_diffrn_orient_matrix_UB_23      0.0135721000
_diffrn_orient_matrix_UB_31      0.0523295000
_diffrn_orient_matrix_UB_32      0.0047695000
_diffrn_orient_matrix_UB_33      -0.0044028000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1005
_diffrn_reflns_av_unetI/netI     0.2786
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            22340
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.900
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.523
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_description       stick
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.623
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     685
_refine_ls_number_reflns         10919
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.862
_refine_ls_R_factor_all          0.2308
_refine_ls_R_factor_gt           0.0874
_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^)+(0.0457P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1567
_refine_ls_wR_factor_ref         0.2051
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3440
_reflns_number_total             10919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01596e2.cif
_cod_data_source_block           1
_cod_database_code               1551472
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C175
_shelx_estimated_absorpt_t_max   0.984
_shelx_estimated_absorpt_t_min   0.838
_reflns_odcompleteness_completeness 99.74
_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
2.a Secondary CH2 refined with riding coordinates:
 C61(H61A,H61B), C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C9(H9), C10(H10), C14(H14), C15(H15), C21(H21), C26(H26), C27(H27),
 C29(H29), C30(H30), C32(H32), C33(H33), C35(H35), C36(H36), C38(H38), C39(H39),
  C40(H40), C41(H41), C42(H42), C44(H44), C45(H45), C47(H47), C48(H48),
 C50(H50), C51(H51), C53(H53), C54(H54), C56(H56), C57(H57), C58(H58), C59(H59),
  C60(H60)
;
_shelx_res_checksum              98285
_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 1.255
_oxdiff_exptl_absorpt_empirical_full_min 0.628