Carbazole-Containing Porphyrinoid and its Oligomers
Song, Jianxin; Wu, Tongjing; Kim, Taeyeon; Yin, Bangshao; Wang, Kaisheng; Xu, Ling; Zhou, Mingbo; Kim, Dongho; Chemical Communications  (2019) –; doi:10.1039/C9CC06114B

data_7124066
_publ_section_title
;
 Carbazole-Containing Porphyrinoid and its Oligomers
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC06114B
_journal_year                    2019
_chemical_formula_moiety         'C108 H110 N8 O2 Zn2'
_chemical_formula_sum            'C108 H110 N8 O2 Zn2'
_chemical_formula_weight         1682.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-11-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2019-06-10 deposited with the CCDC.    2019-08-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.236(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.7916(8)
_cell_length_b                   12.9587(3)
_cell_length_c                   36.5620(11)
_cell_measurement_reflns_used    14165
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      72.6500
_cell_measurement_theta_min      4.1900
_cell_volume                     11732.6(6)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0697
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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    -32.00  52.00   1.00    2.50    --   34.48 -38.00   0.00   84
  2  \w     21.00 103.00   1.00    2.50    --   34.48  38.00 -90.00   82
  3  \w     39.00  66.00   1.00    2.50    --   34.48  57.00 -90.00   27
  4  \w     16.00 101.00   1.00    2.50    --   34.48  77.00 -60.00   85
  5  \w    118.00 145.00   1.00   12.00    --  107.46 111.00  60.00   27
  6  \w     92.00 160.00   1.00   12.00    --  107.46  45.00   0.00   68
  7  \w     89.00 116.00   1.00   12.00    --  107.46  30.00 150.00   27
  8  \w    148.00 175.00   1.00   12.00    --  107.46  30.00 150.00   27
  9  \w     82.00 118.00   1.00   12.00    --  107.46 -45.00 -30.00   36
 10  \w     86.00 113.00   1.00   12.00    --  107.46-111.00 -30.00   27
 11  \w     66.00 108.00   1.00   12.00    --  107.46 -94.00  30.00   42
 12  \w     59.00 125.00   1.00   12.00    --  107.46 -45.00  30.00   66
 13  \w     62.00 114.00   1.00   12.00    --  107.46-111.00 150.00   52
 14  \w     54.00  86.00   1.00   12.00    --  107.46 -77.00  90.00   32
 15  \w     39.00 121.00   1.00   12.00    --  107.46 -45.00 120.00   82
 16  \w     36.00  63.00   1.00    2.50    --   34.48-125.00 120.00   27
 17  \w     30.00  88.00   1.00    2.50    --   34.48-125.00  60.00   58
 18  \w     40.00  67.00   1.00   12.00    --  107.46 -45.00 -30.00   27
 19  \w     61.00 134.00   1.00   12.00    --  107.46 -77.00 -90.00   73
 20  \w     52.00  88.00   1.00    2.50    --   34.48-125.00-120.00   36
 21  \w     39.00  75.00   1.00    2.50    --   34.48-125.00-180.00   36
 22  \w     26.00  53.00   1.00    2.50    --   34.48-125.00-150.00   27
 23  \w     37.00 105.00   1.00   12.00    --  107.46-111.00 -90.00   68
 24  \w     49.00  95.00   1.00   12.00    --  107.46 -94.00-180.00   46
 25  \w     39.00 125.00   1.00   12.00    --  107.46 -45.00-150.00   86
 26  \w    103.00 175.00   1.00   12.00    --  107.46  77.00-180.00   72
 27  \w     38.00 174.00   1.00   12.00    --  107.46   0.00 150.00  136
 28  \w    -33.00  33.00   1.00    2.50    --   34.48 -77.00-180.00   66
 29  \w    -42.00  35.00   1.00    2.50    --  -34.48  38.00-150.00   77
 30  \w    -35.00  21.00   1.00    2.50    --   34.48 -38.00  90.00   56
 31  \w    -48.00 -23.00   1.00    2.50    --  -34.48 -57.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, 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      0.0526189000
_diffrn_orient_matrix_UB_12      -0.0625953000
_diffrn_orient_matrix_UB_13      0.0069928000
_diffrn_orient_matrix_UB_21      -0.0036478000
_diffrn_orient_matrix_UB_22      -0.0287894000
_diffrn_orient_matrix_UB_23      0.0401146000
_diffrn_orient_matrix_UB_31      -0.0330381000
_diffrn_orient_matrix_UB_32      -0.0967574000
_diffrn_orient_matrix_UB_33      -0.0164199000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1037
_diffrn_reflns_av_unetI/netI     0.1123
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            20751
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         3.570
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.830
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47942
_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            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    0.953
_exptl_crystal_description       plate
_exptl_crystal_F_000             3560
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.06
_platon_squeeze_details
;
;
_refine_diff_density_max         0.827
_refine_diff_density_min         -0.492
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1114
_refine_ls_number_reflns         20751
_refine_ls_number_restraints     54
_refine_ls_restrained_S_all      0.913
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0598
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0791P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1464
_refine_ls_wR_factor_ref         0.1620
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12410
_reflns_number_total             20751
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc06114b2.cif
_cod_data_source_block           exp_242-sr
_cod_database_code               7124066
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         'N8 C200 H200 Zn2 O'
_reflns_odcompleteness_completeness 99.92
_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, All O(H) groups
2. Restrained distances
 O1-H1
 0.85 with sigma of 0.01
 O2-H2
 0.85 with sigma of 0.01
 C105-H1
 1.887278 with sigma of 0.02
 Zn1-H1
 2.749545 with sigma of 0.02
 C106-H2
 1.903435 with sigma of 0.02
 Zn2-H2
 2.719817 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C56) \\sim Ueq, Uanis(C55) \\sim Ueq, Uanis(C54) \\sim Ueq, Uanis(C98)
\\sim Ueq, Uanis(C108) \\sim Ueq, Uanis(C107) \\sim Ueq: with sigma of 0.005
and sigma for terminal atoms of 0.01
Uanis(C99) \\sim Ueq, Uanis(C98) \\sim Ueq, Uanis(C100) \\sim Ueq, Uanis(C54)
\\sim Ueq, Uanis(C56) \\sim Ueq, Uanis(C55) \\sim Ueq, Uanis(C108) \\sim Ueq,
Uanis(C107) \\sim Ueq: with sigma of 0.003 and sigma for terminal atoms of 0.006
4.a Ternary CH refined with riding coordinates:
 C106(H106)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C10(H10), C14(H14), C15(H15), C19(H19), C20(H20),
 C24(H24), C28(H28), C32(H32), C33(H33), C37(H37), C38(H38), C41(H41), C43(H43),
  C46(H46), C48(H48), C63(H63), C65(H65), C72(H72), C74(H74), C81(H81),
 C83(H83), C90(H90), C92(H92)
4.c Idealised Me refined as rotating group:
 C54(H54A,H54B,H54C), C55(H55A,H55B,H55C), C56(H56A,H56B,H56C), C58(H58A,H58B,
 H58C), C59(H59A,H59B,H59C), C60(H60A,H60B,H60C), C67(H67A,H67B,H67C), C68(H68A,
 H68B,H68C), C69(H69A,H69B,H69C), C76(H76A,H76B,H76C), C77(H77A,H77B,H77C),
 C78(H78A,H78B,H78C), C85(H85A,H85B,H85C), C86(H86A,H86B,H86C), C87(H87A,H87B,
 H87C), C94(H94A,H94B,H94C), C95(H95A,H95B,H95C), C96(H96A,H96B,H96C), C98(H98A,
 H98B,H98C), C99(H99A,H99B,H99C), C100(H10M,H10N,H10O), C102(H10G,H10H,H10I),
 C103(H10J,H10K,H10L), C104(H10D,H10E,H10F), C105(H10A,H10B,H10C), C107(H10P,
 H10Q,H10R), C108(H10S,H10T,H10U)
;
_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 1.839
_oxdiff_exptl_absorpt_empirical_full_min 0.391