Crystalline salts of anionic free-base tetrapyrazinoporphyrazines with alkyl-substituents or an extended π-electron system
Faraonov, Maxim A.; Osipov, Nikita G.; Romanenko, Nikita R.; Kuzmin, Alexey V.; Kornev, Alexey B.; Stuzhin, Pavel A.; Khasanov, Salavat S.; Konarev, Dmitri V.; New Journal of Chemistry 46 (2022) 22195–22202; doi:10.1039/D2NJ04578H

data_7062016
_publ_section_title
;
 Crystalline salts of anionic free-base tetrapyrazinoporphyrazines with
 alkyl-substituents or an extended \p-electron system
;
_journal_issue                   46
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              22195
_journal_page_last               22202
_journal_paper_doi               10.1039/D2NJ04578H
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C36 H30 N P2, 8(C3 H2 Cl), C20 H21 N8'
_chemical_formula_sum            'C80 H67 Cl8 N9 P2'
_chemical_formula_weight         1499.96
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2022-09-14
_audit_creation_method
;FinalCif V110 by Daniel Kratzert, Freiburg 2022,
https://dkratzert.de/finalcif.html
;
_audit_update_record
;
2022-09-14 deposited with the CCDC.	2022-10-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.537(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.0879(11)
_cell_length_b                   21.1652(10)
_cell_length_c                   32.4886(12)
_cell_measurement_reflns_used    10192
_cell_measurement_temperature    108(7)
_cell_measurement_theta_max      24.0640
_cell_measurement_theta_min      1.9160
_cell_volume                     14433.0(12)
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      108.15
_diffrn_detector_area_resol_mean 5.2283
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.939
_diffrn_measured_fraction_theta_max 0.940
_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    -18.00  20.00   1.00  130.00    --   16.58  47.00-160.00   38
  2  \w    -94.00  -4.00   0.50  130.00    --  -16.73 -62.00  55.11  180
  3  \w    -75.00  12.00   0.50  130.00    --  -16.73 -65.00 -54.82  174
  4  \w    -44.00  -8.00   1.00  130.00    --   16.58 -37.00 -90.00   36
  5  \w    -51.00  59.00   1.00  130.00    --  -16.73  57.00-150.00  110
  6  \w    -23.00 -22.00   1.00  130.00    --  -16.73 -64.00-166.61    1
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_av_unetI/netI     0.1569
_diffrn_reflns_Laue_measured_fraction_full 0.939
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            30857
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        24.499
_diffrn_reflns_theta_max         24.499
_diffrn_reflns_theta_min         1.794
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.925
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
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    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             6208
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.000
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.152
_refine_ls_extinction_coef       0.00040(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     897
_refine_ls_number_reflns         11290
_refine_ls_number_restraints     534
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.2478
_refine_ls_R_factor_gt           0.1805
_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^)+(0.0877P)^2^+850.2062P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3983
_refine_ls_wR_factor_ref         0.4348
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6520
_reflns_number_total             11290
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2nj04578h2.cif
_cod_data_source_block           exp_1706_int1
_cod_depositor_comments
'Adding full bibliography for 7062016--7062018.cif.'
_cod_original_cell_volume        14433.0(11)
_cod_database_code               7062016
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C109) \\sim Ueq, Uanis(C111) \\sim Ueq, Uanis(C129) \\sim Ueq,
Uanis(C130) \\sim Ueq, Uanis(C102) \\sim Ueq, Uanis(C134) \\sim Ueq,
Uanis(C127) \\sim Ueq, Uanis(C117) \\sim Ueq, Uanis(C118) \\sim Ueq,
Uanis(C126) \\sim Ueq, Uanis(C123) \\sim Ueq, Uanis(C135) \\sim Ueq,
Uanis(C122) \\sim Ueq, Uanis(C112) \\sim Ueq, Uanis(C115) \\sim Ueq,
Uanis(C131) \\sim Ueq, Uanis(C119) \\sim Ueq, Uanis(C113) \\sim Ueq,
Uanis(C107) \\sim Ueq, Uanis(C120) \\sim Ueq, Uanis(C124) \\sim Ueq,
Uanis(C128) \\sim Ueq, Uanis(C136) \\sim Ueq, Uanis(C114) \\sim Ueq,
Uanis(C106) \\sim Ueq, Uanis(C132) \\sim Ueq, Uanis(C108) \\sim Ueq,
Uanis(C110) \\sim Ueq, Uanis(C121) \\sim Ueq, Uanis(C133) \\sim Ueq,
Uanis(C116) \\sim Ueq, Uanis(C104) \\sim Ueq, Uanis(C101) \\sim Ueq,
Uanis(C105) \\sim Ueq, Uanis(C103) \\sim Ueq, Uanis(C125) \\sim Ueq, Uanis(C62)
\\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C61) \\sim Ueq, Uanis(C217) \\sim Ueq,
Uanis(C207) \\sim Ueq, Uanis(C215) \\sim Ueq, Uanis(C214) \\sim Ueq,
Uanis(C204) \\sim Ueq, Uanis(C206) \\sim Ueq, Uanis(C219) \\sim Ueq,
Uanis(C220) \\sim Ueq, Uanis(C201) \\sim Ueq, Uanis(C218) \\sim Ueq,
Uanis(C208) \\sim Ueq, Uanis(C211) \\sim Ueq, Uanis(C212) \\sim Ueq,
Uanis(C203) \\sim Ueq, Uanis(C205) \\sim Ueq, Uanis(C213) \\sim Ueq,
Uanis(C209) \\sim Ueq, Uanis(C210) \\sim Ueq, Uanis(C216) \\sim Ueq,
Uanis(C202) \\sim Ueq, Uanis(C73) \\sim Ueq, Uanis(C71) \\sim Ueq, Uanis(C72)
\\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C31) \\sim Ueq,
Uanis(C33) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C44)
\\sim Ueq, Uanis(C43) \\sim Ueq, Uanis(C45) \\sim Ueq, Uanis(C42) \\sim Ueq,
Uanis(C41) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C54) \\sim Ueq, Uanis(C53)
\\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C55) \\sim Ueq, Uanis(C56) \\sim Ueq,
Uanis(C52) \\sim Ueq, Uanis(N101) \\sim Ueq, Uanis(N203) \\sim Ueq, Uanis(N202)
\\sim Ueq, Uanis(N201) \\sim Ueq, Uanis(N204) \\sim Ueq, Uanis(N208) \\sim Ueq,
Uanis(N206) \\sim Ueq, Uanis(N207) \\sim Ueq, Uanis(N205) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C207(H20A,H20B), C215(H21D,H21E), C218(H21F,H21G), C210(H21H,H21I)
3.b Aromatic/amide H refined with riding coordinates:
 C109(H109), C111(H111), C129(H129), C130(H130), C102(H102), C134(H134),
 C127(H127), C117(H117), C118(H118), C126(H126), C123(H123), C135(H135),
 C122(H122), C112(H112), C115(H115), C120(H120), C124(H124), C128(H128),
 C136(H136), C114(H114), C106(H106), C132(H132), C108(H108), C110(H110),
 C121(H121), C133(H133), C116(H116), C104(H104), C105(H105), C103(H103),
 C62(H62), C63(H63), N201(H201), C73(H73), C72(H72), C35(H35), C33(H33),
 C34(H34), C36(H36), C44(H44), C43(H43), C45(H45), C46(H46), C54(H54), C53(H53),
  C55(H55), C56(H56)
3.c Idealised Me refined as rotating group:
 C217(H21A,H21B,H21C), C208(H20C,H20D,H20E), C209(H20F,H20G,H20H), C216(H21J,
 H21K,H21L)
;
_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
;
_shelx_estimated_absorpt_t_min   0.901
_shelx_estimated_absorpt_t_max   0.960
_shelx_res_checksum              25078