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_1551470
_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         'C70 H46 N8 Zn, C H Cl3'
_chemical_formula_sum            'C71 H47 Cl3 N8 Zn'
_chemical_formula_weight         1183.88
_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     direct
_audit_creation_date             2017-07-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-06-29 deposited with the CCDC.    2019-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                67.268(3)
_cell_angle_beta                 82.291(3)
_cell_angle_gamma                82.584(3)
_cell_formula_units_Z            2
_cell_length_a                   10.1189(3)
_cell_length_b                   16.2647(5)
_cell_length_c                   19.3022(6)
_cell_measurement_reflns_used    13039
_cell_measurement_temperature    150
_cell_measurement_theta_max      72.5090
_cell_measurement_theta_min      4.4530
_cell_volume                     2893.14(17)
_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    'SIR2004 (Burla et al., 2007)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   17.00  105.00   1.0000    3.4000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000    0.0000 88

  2 omega   19.00  103.00   1.0000    3.4000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   57.0000 -150.0000 84

  3 omega  -32.00   63.00   1.0000    3.4000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -77.0000  -30.0000 95

  4 omega  -31.00   53.00   1.0000    3.4000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -57.0000    0.0000 84

  5 omega  -33.00   55.00   1.0000    3.4000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -38.0000   60.0000 88

  6 omega   23.00   89.00   1.0000    3.4000
omega____ theta____ kappa____ phi______ frames
    -       36.0421 -125.0000  150.0000 66

  7 omega   17.00  105.00   1.0000    3.4000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000  -60.0000 88

  8 omega  -32.00   63.00   1.0000    3.4000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -77.0000 -120.0000 95

  9 omega    1.00   75.00   1.0000    3.4000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000  -30.0000 74

 10 omega    1.00   75.00   1.0000    3.4000
omega____ theta____ kappa____ phi______ frames
    -       36.0421  -99.0000 -150.0000 74

 11 omega   38.00  116.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 78

 12 omega   39.00  109.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   30.0000 70

 13 omega   40.00   98.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   60.0000 58

 14 omega   39.00  109.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   90.0000 70

 15 omega   81.00  176.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -90.0000 95

 16 omega   39.00  109.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -180.0000 70

 17 omega   40.00   98.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -120.0000 58

 18 omega   38.00   91.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -60.0000 53

 19 omega   40.00   98.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000 -150.0000 58

 20 omega   38.00   91.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 53

 21 omega   38.00  116.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 78

 22 omega   40.00   98.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 58

 23 omega   91.00  176.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   45.0000  -30.0000 85

 24 omega   70.00  178.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   15.0000  -90.0000 108

 25 omega   38.00   91.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 53

 26 omega   40.00   98.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  150.0000 58

 27 omega   57.00  150.00   1.0000   13.5800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   90.0000 93

 28 omega    9.00  104.00   1.0000    3.4000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000    0.0000 95

 29 omega    9.00  104.00   1.0000    3.4000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000  150.0000 95

 30 omega    9.00  104.00   1.0000    3.4000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000  -90.0000 95

 31 omega   17.00   93.00   1.0000    3.4000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   38.0000   90.0000 76

 32 omega    9.00  104.00   1.0000    3.4000
omega____ theta____ kappa____ phi______ frames
    -       36.0421   77.0000   90.0000 95
;
_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      -0.0275185000
_diffrn_orient_matrix_UB_12      0.0948241000
_diffrn_orient_matrix_UB_13      0.0012704000
_diffrn_orient_matrix_UB_21      0.1474896000
_diffrn_orient_matrix_UB_22      -0.0011373000
_diffrn_orient_matrix_UB_23      0.0125823000
_diffrn_orient_matrix_UB_31      0.0355358000
_diffrn_orient_matrix_UB_32      0.0403642000
_diffrn_orient_matrix_UB_33      -0.0859792000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            28348
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        63.691
_diffrn_reflns_theta_max         63.691
_diffrn_reflns_theta_min         4.425
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.268
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56288
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.900
_refine_diff_density_min         -1.158
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.352
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     751
_refine_ls_number_reflns         9511
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.352
_refine_ls_R_factor_all          0.1104
_refine_ls_R_factor_gt           0.0980
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2969
_refine_ls_wR_factor_ref         0.3133
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7727
_reflns_number_total             9511
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01596e2.cif
_cod_data_source_block           lcm-13387-2-150k_sq
_cod_depositor_comments
;

2022-09-15
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C142 H94 Cl6 N16 Zn2'
_cod_original_formula_weight         2367.77
_cod_original_formula_moiety         '2(C70 H46 N8 Zn), 2(C H Cl3)'
_cod_original_formula_units_Z            1
_cod_original_cell_volume        2893.15(16)
_cod_database_code               1551470
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C00H(H00H), C00P(H00P), C00T(H00T), C00X(H00X), C00Y(H00Y), C00Z(H00Z),
 C011(H011), C013(H013), C016(H016), C018(H018), C019(H019), C01A(H01A),
 C01C(H01C), C01D(H01D), C01E(H01E), C01F(H01F), C01G(H01G), C01H(H01H),
 C01I(H01I), C01J(H01J), C01K(H01K), C01L(H01L), C01M(H01M), C01N(H01N),
 C01O(H01O), C01P(H01P), C01S(H01S), C01T(H01T), C01U(H01U), C01V(H01V),
 C01W(H01W), C01X(H01X), C01Z(H01Z), C020(H020), C022(H022), C023(H023),
 C024(H024), C025(H025), C026(H026), C027(H027), C028(H028), C029(H029),
 C02A(H02A), C02B(H02B), C02D(H02D), C4(H4)
;
_shelx_res_checksum              91521
_shelx_fab_checksum              81684
_olex2_submission_special_instructions 'No special instructions were received'