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_1551471
_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         'C34 H24 N6 O2 Zn'
_chemical_formula_sum            'C34 H24 N6 O2 Zn'
_chemical_formula_weight         613.96
_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'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-07-24 deposited with the CCDC.    2019-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 114.758(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1672(4)
_cell_length_b                   27.7657(7)
_cell_length_c                   9.6241(3)
_cell_measurement_reflns_used    3566
_cell_measurement_temperature    296.4(5)
_cell_measurement_theta_max      72.8410
_cell_measurement_theta_min      4.6090
_cell_volume                     2709.81(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (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_environment      air
_diffrn_ambient_temperature      296.4(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_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   -104.00 -20.00   1.00    6.99    --  -36.54 -57.00  30.00   84
  2  \w    -53.00  31.00   1.00    6.99    --  -36.54  57.00  30.00   84
  3  \w   -104.00 -20.00   1.00    6.99    --  -36.54 -57.00 -90.00   84
  4  \w      1.00  75.00   1.00    6.99    --   36.54 -99.00  60.00   74
  5  \w     23.00  90.00   1.00    6.99    --   36.54-125.00-120.00   67
  6  \w     82.00 176.00   1.00   27.96    --  108.71  77.00  60.00   94
  7  \w     39.00 109.00   1.00   27.96    --  108.71 -94.00-180.00   70
  8  \w     40.00 126.00   1.00   27.96    --  108.71 -45.00 -90.00   86
  9  \w     91.00 176.00   1.00   27.96    --  108.71  61.00  30.00   85
 10  \w     39.00 109.00   1.00   27.96    --  108.71 -94.00 120.00   70
 11  \w    100.00 178.00   1.00   27.96    --  108.71 111.00-120.00   78
 12  \w    100.00 178.00   1.00   27.96    --  108.71 111.00 120.00   78
 13  \w     39.00 115.00   1.00   27.96    --  108.71-111.00 -60.00   76
 14  \w     41.00 135.00   1.00   27.96    --  108.71 -77.00 -60.00   94
 15  \w   -104.00 -38.00   1.00    6.99    --  -36.54 -77.00 150.00   66
;
_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_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0089931000
_diffrn_orient_matrix_UB_12      0.0545354000
_diffrn_orient_matrix_UB_13      -0.0322667000
_diffrn_orient_matrix_UB_21      -0.1514025000
_diffrn_orient_matrix_UB_22      -0.0037519000
_diffrn_orient_matrix_UB_23      -0.0810510000
_diffrn_orient_matrix_UB_31      -0.0087300000
_diffrn_orient_matrix_UB_32      0.0094911000
_diffrn_orient_matrix_UB_33      0.1532108000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7639
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.852
_diffrn_reflns_theta_min         4.642
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.625
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
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    1.505
_exptl_crystal_description       needle
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.963
_refine_diff_density_min         -0.609
_refine_diff_density_rms         0.093
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2670
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0623
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1317P)^2^+2.4419P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.1856
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2233
_reflns_number_total             2670
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9sc01596e2.cif
_cod_data_source_block           lcm-386
_cod_original_cell_volume        2709.82(17)
_cod_database_code               1551471
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C00B, N005
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
C00B \\sim N005: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
4.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00F(H00F), C00H(H00H), C00I(H00I), C00K(H00K),
 C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P)
4.b Idealised Me refined as rotating group:
 C00L(H00A,H00B,H00C)
;
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.471
_oxdiff_exptl_absorpt_empirical_full_min 0.743