Solvent-regulated biomorphs from the intense π,π-mediated assemblies of tetracenequinone fused porphyrin
Chen, Chen; Li, Dan; Cao, Guanyue; Qin, Zhonghe; Xu, Yi; Liu, Xiujun; Li, Qizhao; Xie, Yongshu; Li, Chengjie; CrystEngComm 23 (2021) 7565–7569; doi:10.1039/D1CE01173A

data_7243658
_publ_section_title
;
 Solvent-regulated biomorphs from the intense \p,\p-mediated assemblies of
 tetracenequinone fused porphyrin
;
_journal_issue                   43
_journal_name_full               CrystEngComm
_journal_page_first              7565
_journal_page_last               7569
_journal_paper_doi               10.1039/D1CE01173A
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         '0.998(C140.6 H117.831 N4 Ni O8)'
_chemical_formula_sum            'C140.3 H117.1 N4 Ni O8'
_chemical_formula_weight         2045.79
_chemical_name_systematic        Ni4TQ
_space_group_crystal_system      tetragonal
_space_group_IT_number           81
_space_group_name_Hall           'P -4'
_space_group_name_H-M_alt        'P -4'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-06-14
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-08-16 deposited with the CCDC.	2021-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   20.4751(3)
_cell_length_b                   20.4751(3)
_cell_length_c                   13.4593(10)
_cell_measurement_reflns_used    5584
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      67.9430
_cell_measurement_theta_min      3.0020
_cell_volume                     5642.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.946
_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   -108.00 -11.00   0.50    0.05    --  -36.74 -47.00  -3.00  194
  2  \w     12.00  98.00   0.50    0.05    --   36.74-121.00 127.00  172
  3  \w   -167.00 -91.00   0.50    0.13    -- -100.00 -47.00  -3.00  152
  4  \w   -112.00 -35.00   0.50    0.13    -- -100.00 121.00-149.00  154
  5  \w   -157.00 -98.00   0.50    0.13    -- -100.00 -74.00-160.00  118
  6  \w   -121.00 -76.00   0.50    0.05    --  -36.74-179.00-150.00   90
  7  \w    -73.00 -48.00   0.50    0.05    --  -36.74-179.00   0.00   50
  8  \w    -19.00  65.00   0.50    0.05    --   36.74 -57.00 -60.00  168
  9  \w   -132.00 -99.00   0.50    0.13    -- -100.00  61.00   0.00   66
 10  \w    -55.00 -28.00   0.50    0.13    -- -100.00  61.00   0.00   54
 11  \w   -120.00 -90.00   0.50    0.13    -- -100.00-111.00   0.00   60
 12  \w     30.00  55.00   0.50    0.13    --  110.24 -94.00 -60.00   50
 13  \w     34.00  78.00   0.50    0.13    --  110.24 -94.00-180.00   88
 14  \w     27.00 111.00   0.50    0.13    --  110.24-111.00 150.00  168
 15  \w     28.00 112.00   0.50    0.13    --  110.24-111.00 -30.00  168
 16  \w     26.00 101.00   0.50    0.13    --  110.24 -94.00 -30.00  150
 17  \w     25.00 104.00   0.50    0.13    --  110.24 -94.00 150.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0067455000
_diffrn_orient_matrix_UB_12      0.0147644000
_diffrn_orient_matrix_UB_13      0.1117787000
_diffrn_orient_matrix_UB_21      -0.0611860000
_diffrn_orient_matrix_UB_22      0.0415796000
_diffrn_orient_matrix_UB_23      -0.0213941000
_diffrn_orient_matrix_UB_31      -0.0433101000
_diffrn_orient_matrix_UB_32      -0.0608821000
_diffrn_orient_matrix_UB_33      0.0125763000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23848
_diffrn_reflns_point_group_measured_fraction_full 0.872
_diffrn_reflns_point_group_measured_fraction_max 0.822
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.443
_diffrn_reflns_theta_min         2.158
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58260
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             2158
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.046
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 2298 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.50(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     838
_refine_ls_number_reflns         9343
_refine_ls_number_restraints     992
_refine_ls_restrained_S_all      1.196
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0708
_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^)+(0.1453P)^2^+0.4544P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1993
_refine_ls_wR_factor_ref         0.2207
_reflns_Friedel_coverage         0.661
_reflns_Friedel_fraction_full    0.749
_reflns_Friedel_fraction_max     0.686
_reflns_number_gt                6673
_reflns_number_total             9343
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce01173a2.cif
_cod_data_source_block           ni
_cod_depositor_comments
'Adding full bibliography for 7243657--7243658.cif.'
_cod_original_cell_volume        5642.5(5)
_cod_original_formula_sum        'C140.30 H117.10 N4 Ni O8'
_cod_database_code               7243658
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C140H116N4NiO8
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.868
_reflns_odcompleteness_completeness 98.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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
 C4-C2 = C4-C1
 1.57 with sigma of 0.02
 C024-C01A = C01W-C01A = C021-C01A
 1.57 with sigma of 0.02
 C4-C2
 1.6 with sigma of 0.02
 C4-C3
 1.57 with sigma of 0.02
 C4-C1
 1.6 with sigma of 0.02
 C4-C3 = C4-C2
 1.7 with sigma of 0.02
 C4-C3 = C4-C2 = C4-C1
 1.7 with sigma of 0.02
 C1-C2
 2.44 with sigma of 0.04
 C3-C1
 2.44 with sigma of 0.04
 C2A-C3A
 1.7 with sigma of 0.04
 C3-C2
 2.7 with sigma of 0.04
 C018-C12
 3 with sigma of 0.04
 C11-C12
 2.7 with sigma of 0.04
 C0-C12
 2.7 with sigma of 0.04
 C01S-C16
 2.7 with sigma of 0.04
 C16-C01Y
 2.7 with sigma of 0.04
 C01T-C01V
 2.7 with sigma of 0.04
 C01X-C01V
 2.7 with sigma of 0.04
 C14-C025
 2.6 with sigma of 0.04
 C7-C01V
 2.6 with sigma of 0.04
 C025-C022 \\sim C022-C01U \\sim C14-C022
 with sigma of 0.02
 C024-C01A \\sim C01W-C01A \\sim C021-C01A
 with sigma of 0.02
 C01J-C010 \\sim C01B-C010 \\sim C01B-C00G \\sim C00P-C00G \\sim C018-C00P
\\sim C01J-C018
 with sigma of 0.02
 C4-C2 \\sim C4-C1 \\sim C4-C3
 with sigma of 0.02
 C9-C10 \\sim C9-C10A
 with sigma of 0.02
 C8-C6 \\sim C8-C6A
 with sigma of 0.04
 C10-C5 \\sim C10A-C5A
 with sigma of 0.02
 C7-C6 \\sim C7A-C6A
 with sigma of 0.02
 C8-C7 \\sim C8-C7A
 with sigma of 0.02
 C6-C4 \\sim C6A-C4
 with sigma of 0.04
 C9-C5 \\sim C9-C5A
 with sigma of 0.04
 C10-C6 \\sim C10A-C6A
 with sigma of 0.04
 C7-C5 \\sim C7A-C5A
 with sigma of 0.04
 C10-C4 \\sim C10A-C4
 with sigma of 0.04
 C01Q-C6 \\sim C01Q-C6A
 with sigma of 0.04
 C6-C5 \\sim C6A-C5A
 with sigma of 0.02
 C7-C01Q \\sim C7A-C01Q
 with sigma of 0.02
 C5-C4 \\sim C5A-C4
 with sigma of 0.02
 C3-C2 \\sim C3A-C2A
 with sigma of 0.02
 C4-C2 \\sim C4-C2A
 with sigma of 0.02
 C1-C4 \\sim C1A-C4
 with sigma of 0.02
 C3-C4 \\sim C3A-C4
 with sigma of 0.04
 C4-C3A \\sim C4-C2A \\sim C4-C1A
 with sigma of 0.02
 C01X-C01Q \\sim C01S-C01Q \\sim C01V-C01Q
 with sigma of 0.02
 C5-C4 \\sim C5A-C2A
 with sigma of 0.02
 C01A-C01W \\sim C01A-C11
 with sigma of 0.02
 C01A-C021 \\sim C01A-C0
 with sigma of 0.02
 C01A-C024 \\sim C01A-C12
 with sigma of 0.02
 C01W-C01A \\sim C11-C01A \\sim C024-C01A \\sim C12-C01A \\sim C021-C01A \\sim
C01A-C0
 with sigma of 0.02
 C01U-C022 \\sim C15-C022
 with sigma of 0.02
 C14-C022 \\sim C14A-C022
 with sigma of 0.02
 C022-C025 \\sim C022-C13
 with sigma of 0.02
 C14-C022 \\sim C13-C022 \\sim C025-C022 \\sim C15-C022 \\sim C14A-C022 \\sim
C022-C01U
 with sigma of 0.02
 C01T-C01Q \\sim C01S-C01Q
 with sigma of 0.02
 C01S-C01Q \\sim C01Y-C01Q \\sim C16-C01Q
 with sigma of 0.02
 C01V-C01Q \\sim C01T-C01Q \\sim C01X-C01Q
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C00G \\sim C00P \\sim C01B \\sim C01J \\sim C010 \\sim C018: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C01A) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C10) = Uanis(C10A)
Uanis(C4) = Uanis(C4A)
Uanis(C12) = Uanis(C024)
Uanis(C01S) = Uanis(C01T)
Uanis(C01X) = Uanis(C01Y)
Uanis(C01V) = Uanis(C16)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H8B)=Sof(C10A)=Sof(H10A)=1-FVAR(1)
 Sof(C5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H8A)=Sof(C10)=Sof(H10)=FVAR(1)
 Sof(C1A)=Sof(H1AB)=Sof(H1AC)=Sof(C2A)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=
 1-FVAR(2)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=Sof(C3)=
 Sof(H3A)=Sof(H3B)=Sof(H3C)=FVAR(2)
 Sof(C4)=1-FVAR(3)
 Sof(C4A)=FVAR(3)
 Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12)=Sof(H12A)=Sof(H12B)=Sof(H12C)=
 1-FVAR(4)
 Sof(C01W)=Sof(H01Z)=Sof(HB)=Sof(HC)=Sof(C021)=Sof(H02A)=Sof(H02B)=Sof(H02C)=
 FVAR(4)
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14A)=Sof(C15)=Sof(H15A)=Sof(H15B)=
 Sof(H15C)=1-FVAR(5)
 Sof(C01U)=Sof(H01Y)=Sof(H)=Sof(HA)=Sof(C14)=Sof(H14B)=Sof(H14C)=Sof(C025)=
 FVAR(5)
 Sof(C01Y)=Sof(H01M)=Sof(H01O)=Sof(H01Q)=1-FVAR(6)
 Sof(C01X)=Sof(H01J)=Sof(H01K)=Sof(H01L)=FVAR(6)
 Sof(C01S)=Sof(H01A)=Sof(H01B)=Sof(H01C)=FVAR(7)
 Sof(C01T)=Sof(H01D)=Sof(H01E)=Sof(H01F)=FVAR(8)
 Fixed Sof: H1AA(0.75) C01V(0.5) H01G(0.5) H01H(0.5) H01I(0.5) H4AA(0.5)
 H4AB(0.5) H4AC(0.5) C16(0.5) H16A(0.5) H16B(0.5) H16C(0.5) C0(0.5) H0A(0.5)
 H0B(0.5) H0C(0.5) H14A(0.8) H14D(0.75) H14E(0.5) H14F(0.5) C024(0.5) H02D(0.5)
 H02E(0.5) H02F(0.5) H02G(0.3) H02H(0.3) H02I(0.3)
6.a Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00O(H00O), C00R(H00R), C00U(H00U), C00Z(H00Z), C01N(H01N),
 C01P(H01P), C6(H6), C6A(H6A), C8(H8A), C8(H8B), C009(H009), C10(H10),
 C10A(H10A), C00C(H00C), C00P(H00P), C00Q(H00Q), C01B(H01R), C01C(H01S),
 C01E(H01T), C01I(H01U), C01J(H01V), C01M(H01W), C01O(H01X), C012(H012)
6.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC), C01S(H01A,H01B,H01C), C01T(H01D,H01E,
 H01F), C01V(H01G,H01H,H01I), C01X(H01J,H01K,H01L), C01Y(H01M,H01O,H01Q),
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C3A(H3AA,H3AB,H3AC), C4A(H4AA,H4AB,H4AC),
 C16(H16A,H16B,H16C), C0(H0A,H0B,H0C), C01U(H01Y,H,HA), C01W(H01Z,HB,HC),
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C), C14A(H14D,H14E,H14F), C15(H15A,H15B,H15C), C021(H02A,H02B,H02C),
 C024(H02D,H02E,H02F), C025(H02G,H02H,H02I)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              75036
_shelx_hkl_checksum              67383
_shelx_fab_checksum              13097
_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 1.870
_oxdiff_exptl_absorpt_empirical_full_min 0.780