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_1551473
_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
'F6 Sb, C65 H43 F4 N6 O2 Zn, C H2 Cl2, C4 H8 O'
_chemical_formula_sum            'C70 H53 Cl2 F10 N6 O3 Sb Zn'
_chemical_formula_weight         1474.20
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-06-28
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-06-29 deposited with the CCDC.    2019-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.6455(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.2843(2)
_cell_length_b                   17.94042(16)
_cell_length_c                   17.71991(20)
_cell_measurement_reflns_used    14746
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.5480
_cell_measurement_theta_min      4.5080
_cell_volume                     6238.91(11)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_environment      air
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details
;
  1 omega   20.00  104.00   1.0000    3.7400
omega____ theta____ kappa____ phi______ frames
    -       36.5421   57.0000   60.0000 84

  2 omega   18.00  106.00   1.0000    3.7400
omega____ theta____ kappa____ phi______ frames
    -       36.5421   38.0000  -60.0000 88

  3 omega    1.00   75.00   1.0000    3.7400
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  -90.0000 74

  4 omega   10.00  104.00   1.0000    3.7400
omega____ theta____ kappa____ phi______ frames
    -       36.5421   77.0000  -30.0000 94

  5 omega  -33.00   55.00   1.0000    3.7400
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -38.0000   90.0000 88

  6 omega    1.00   75.00   1.0000    3.7400
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000  120.0000 74

  7 omega    1.00   75.00   1.0000    3.7400
omega____ theta____ kappa____ phi______ frames
    -       36.5421  -99.0000 -180.0000 74

  8 omega   40.00   98.00   1.0000   14.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  120.0000 58

  9 omega   39.00  109.00   1.0000   14.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  150.0000 70

 10 omega   38.00   91.00   1.0000   14.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 11 omega   40.00   98.00   1.0000   14.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 58

 12 omega   40.00   98.00   1.0000   14.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 13 omega   90.00  175.00   1.0000   14.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  120.0000 85

 14 omega   38.00   91.00   1.0000   14.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 53

 15 omega   39.00  109.00   1.0000   14.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

 16 omega   38.00   91.00   1.0000   14.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

 17 omega   91.00  116.00   1.0000   14.9600
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000 -180.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0203195000
_diffrn_orient_matrix_UB_12      -0.0509893000
_diffrn_orient_matrix_UB_13      0.0603716000
_diffrn_orient_matrix_UB_21      0.0735715000
_diffrn_orient_matrix_UB_22      -0.0298475000
_diffrn_orient_matrix_UB_23      0.0254639000
_diffrn_orient_matrix_UB_31      0.0185541000
_diffrn_orient_matrix_UB_32      0.0622725000
_diffrn_orient_matrix_UB_33      0.0614723000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32809
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.744
_diffrn_reflns_theta_min         4.506
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    5.419
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dull blackish black'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_description       block
_exptl_crystal_F_000             2976
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.634
_refine_diff_density_min         -1.466
_refine_diff_density_rms         0.111
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     860
_refine_ls_number_reflns         11878
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1081P)^2^+4.5330P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1520
_refine_ls_wR_factor_ref         0.1619
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9736
_reflns_number_total             11878
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01596e2.cif
_cod_data_source_block           lcm-b393
_cod_original_cell_volume        6238.92(12)
_cod_database_code               1551473
_reflns_odcompleteness_completeness 98.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 O2A-C3A
 1.88 with sigma of 0.01
 O2-C3
 1.88 with sigma of 0.01
3. Others
 Sof(O2A)=1-FVAR(1)
 Sof(O2)=FVAR(1)
 Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=1-FVAR(2)
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(H3C)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C028(H02A,H02B), C02A(H02C,H02D), C02E(H02H,H02I), C02F(H02J,H02K), C02G(H02L,
 H02M), C02H(H02T,H02U), C02J(H02N,H02O), C02L(H02P,H02Q), C02M(H02R,H02S)
4.b Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00R(H00R), C00V(H00V), C00X(H00X), C00Y(H00Y), C013(H013),
 C018(H018), C01C(H01C), C01E(H01E), C01J(H01J), C01K(H01K), C01M(H01M),
 C01N(H01N), C01O(H01O), C01P(H01P), C01Q(H01Q), C01R(H01R), C01S(H01S),
 C01T(H01T), C01V(H01V), C01X(H01X), C01Z(H01Z), C020(H020), C022(H022),
 C023(H023), C024(H024), C026(H026), C027(H027), C029(H029), C02B(H02E),
 C02C(H02F), C02D(H02G)
4.c Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C3A(H3AA,H3AB,H3AC)
;
_shelx_res_checksum              30558
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2017-06-28
_olex2_submission_special_instructions 'No special instructions were received'