Synthesis, structure and properties of coordination complexes of tin(ii) phthalocyanine and naphthalocyanine with transition metal fragments
Faraonov, Maxim A.; Yudanova, Evgeniya I.; Kuzmin, Alexey V.; Khasanov, Salavat S.; Troyanov, Sergey I.; Otsuka, Akihiro; Yamochi, Hideki; Kitagawa, Hiroshi; Konarev, Dmitri V.; CrystEngComm 25 (2023) 4620–4637; doi:10.1039/D3CE00564J

data_7247038
_publ_section_title
;
 Synthesis, structure and properties of coordination complexes of tin(ii)
 phthalocyanine and naphthalocyanine with transition metal fragments
;
_journal_issue                   33
_journal_name_full               CrystEngComm
_journal_page_first              4620
_journal_page_last               4637
_journal_paper_doi               10.1039/D3CE00564J
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety
'2(C36 H16 Fe N8 O4 Sn), 2(C18 H36 K N2 O6), 4(C6 H4 Cl2)'
_chemical_formula_sum            'C132 H120 Cl8 Fe2 K2 N20 O20 Sn2'
_chemical_formula_weight         3017.35
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-05-23
_audit_creation_method
;FinalCif V121 by Daniel Kratzert, Freiburg 2023, 
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2023-05-23 deposited with the CCDC.	2023-07-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.7101(6)
_cell_length_b                   14.5414(8)
_cell_length_c                   39.6766(16)
_cell_measurement_reflns_used    17493
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.1380
_cell_measurement_theta_min      1.7220
_cell_volume                     13102.7(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.89a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2283
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.916
_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    -35.00  89.00   1.00   75.00    --    8.58  19.00-180.00  124
  2  \w    -71.00  -3.00   1.00   75.00    --    8.58 -19.00   0.00   68
  3  \w    -60.00 -32.00   1.00   75.00    --    8.58 -19.00  90.00   28
  4  \w    -47.00 -19.00   1.00   75.00    --    8.58 -37.00 -60.00   28
  5  \w    -41.00  16.00   1.00   75.00    --   -8.74 -39.00 -75.84   57
  6  \w    -33.00  11.00   1.00   75.00    --   -8.74 -40.00 -10.69   44
  7  \w    -83.00  17.00   1.00   75.00    --   -8.74 -40.00-152.44  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0008481000
_diffrn_orient_matrix_UB_12      -0.0485144000
_diffrn_orient_matrix_UB_13      0.0018495000
_diffrn_orient_matrix_UB_21      0.0006765000
_diffrn_orient_matrix_UB_22      -0.0050626000
_diffrn_orient_matrix_UB_23      -0.0177677000
_diffrn_orient_matrix_UB_31      0.0312226000
_diffrn_orient_matrix_UB_32      -0.0011997000
_diffrn_orient_matrix_UB_33      0.0004239000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1398
_diffrn_reflns_av_unetI/netI     0.1573
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.916
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            150665
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.883
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.250
_diffrn_reflns_theta_min         1.663
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.896
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_correction_T_min  0.794
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.89a (Rigaku Oxford Diffraction, 2023)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_description       plate
_exptl_crystal_F_000             6152
_exptl_crystal_size_max          0.477
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.026
_refine_diff_density_max         1.194
_refine_diff_density_min         -0.978
_refine_diff_density_rms         0.141
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.51(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1599
_refine_ls_number_reflns         28632
_refine_ls_number_restraints     1518
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1381
_refine_ls_R_factor_gt           0.0773
_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^)+(0.0601P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1367
_refine_ls_wR_factor_ref         0.1596
_reflns_Friedel_coverage         0.901
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.849
_reflns_number_gt                18600
_reflns_number_total             28632
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00564j2.cif
_cod_data_source_block           exp_1027_int1
_cod_depositor_comments
'Adding full bibliography for 7247026--7247038.cif.'
_cod_database_code               7247038
_chemical_oxdiff_formula         'C528  N80  O80  Cl32  K8  Fe8  Sn8  '
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.49(3)
 0.51(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Restrained distances
 O403-C409 \\sim O403-C419
 with sigma of 0.02
 O404-C410 \\sim O404-C420
 with sigma of 0.02
 C409-C410 \\sim C419-C420
 with sigma of 0.02
 O403-C410 \\sim O403-C420
 with sigma of 0.04
 O404-C409 \\sim O404-C419
 with sigma of 0.04
4. Uiso/Uaniso restraints and constraints
C124 \\sim C135 \\sim C133 \\sim C102 \\sim C128 \\sim C125 \\sim C134 \\sim
C103 \\sim C113 \\sim C109 \\sim C118 \\sim C110 \\sim C114 \\sim C122 \\sim
C127 \\sim C131 \\sim C136 \\sim C104 \\sim C115 \\sim C116 \\sim C117 \\sim
C107 \\sim C106 \\sim C132 \\sim C111 \\sim C123 \\sim C130 \\sim C105 \\sim
C121 \\sim C126 \\sim C112 \\sim C120 \\sim C101 \\sim C119 \\sim C108 \\sim
C129: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002
within 2A
N104 \\sim N106 \\sim N101 \\sim N105 \\sim N107 \\sim N103 \\sim N102 \\sim
N00O: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002
within 2A
C233 \\sim C220 \\sim C219 \\sim C234 \\sim C203 \\sim C235 \\sim C204 \\sim
C236 \\sim C226 \\sim C201 \\sim C211 \\sim C208 \\sim C227 \\sim C209 \\sim
C212 \\sim C216 \\sim C228 \\sim C217 \\sim C231 \\sim C224 \\sim C206 \\sim
C225 \\sim C214 \\sim C232 \\sim C222 \\sim C202 \\sim C230 \\sim C207 \\sim
C205 \\sim C210 \\sim C213 \\sim C215 \\sim C221 \\sim C218 \\sim C223 \\sim
C229: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002
within 2A
N201 \\sim N208 \\sim N204 \\sim N203 \\sim N202 \\sim N205 \\sim N207 \\sim
N206: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002
within 2A
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(C409) = Uanis(C419)
Uanis(C420) = Uanis(C410)
Uanis(N103) = Uanis(N107) = Uanis(N00O) = Uanis(N101) = Uanis(N102) =
Uanis(N104) = Uanis(N105) = Uanis(N106)
Uanis(N201) = Uanis(N208) = Uanis(N204) = Uanis(N203) = Uanis(N202) =
Uanis(N205) = Uanis(N207) = Uanis(N206)
5. Others
 Sof(C419)=Sof(H41S)=Sof(H41T)=Sof(C420)=Sof(H42A)=Sof(H42B)=1-FVAR(1)
 Sof(C409)=Sof(H40Q)=Sof(H40R)=Sof(C410)=Sof(H41A)=Sof(H41B)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C301(H30A,H30B), C302(H30C,H30D), C303(H30E,H30F), C304(H30G,H30H), C305(H30I,
 H30J), C306(H30K,H30L), C307(H30M,H30N), C308(H30O,H30P), C309(H30Q,H30R),
 C310(H31A,H31B), C311(H31C,H31D), C312(H31E,H31F), C313(H31G,H31H), C314(H31I,
 H31J), C315(H31K,H31L), C316(H31M,H31N), C317(H31O,H31P), C318(H31Q,H31R),
 C401(H40A,H40B), C402(H40C,H40D), C403(H40E,H40F), C404(H40G,H40H), C405(H40I,
 H40J), C406(H40K,H40L), C407(H40M,H40N), C408(H40O,H40P), C409(H40Q,H40R),
 C410(H41A,H41B), C411(H41C,H41D), C412(H41E,H41F), C413(H41G,H41H), C414(H41I,
 H41J), C415(H41K,H41L), C416(H41M,H41N), C417(H41O,H41P), C418(H41Q,H41R),
 C419(H41S,H41T), C420(H42A,H42B)
6.b Aromatic/amide H refined with riding coordinates:
 C103(H103), C104(H104), C105(H105), C106(H106), C111(H111), C112(H112),
 C113(H113), C114(H114), C119(H119), C120(H120), C121(H121), C122(H122),
 C127(H127), C128(H128), C129(H129), C130(H130), C203(H203), C204(H204),
 C205(H205), C206(H206), C211(H211), C212(H212), C213(H213), C214(H214),
 C219(H219), C220(H220), C221(H221), C222(H222), C227(H227), C228(H228),
 C229(H229), C230(H230), C53(H53), C54(H54), C55(H55), C56(H56), C63(H63),
 C64(H64), C65(H65), C66(H66), C73(H73), C74(H74), C75(H75), C76(H76), C83(H83),
  C84(H84), C85(H85), C86(H86)
;
_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 1.108
_oxdiff_exptl_absorpt_empirical_full_min 0.897
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.674
_shelx_estimated_absorpt_t_max   0.977
_shelx_res_checksum              15827