#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/25/7122557.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7122557
loop_
_publ_author_name
'Diaz-Rodriguez, Roberto M'
'Robertson, Katherine N.'
'Thompson, Alison'
_publ_section_title
;
 Synthesis and reactivity of aza-dipyrrin alkali metal salts.
;
_journal_issue                   93
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13139
_journal_page_last               13142
_journal_paper_doi               10.1039/c8cc07101b
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C56 H36 N6 Zn'
_chemical_formula_sum            'C56 H36 N6 Zn'
_chemical_formula_weight         858.28
_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
_audit_creation_method           SHELXL-2018/1
_audit_update_record
;
2018-08-22 deposited with the CCDC.
2018-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 108.675(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.287(4)
_cell_length_b                   11.257(2)
_cell_length_c                   16.403(3)
_cell_measurement_reflns_used    2423
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      21.78
_cell_measurement_theta_min      2.25
_cell_volume                     4073.5(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1533
_diffrn_reflns_av_unetI/netI     0.1074
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18276
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.401
_diffrn_reflns_theta_max         24.401
_diffrn_reflns_theta_min         1.846
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_description       'long thin needle'
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          0.575
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         3343
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.1263
_refine_ls_R_factor_gt           0.0558
_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/[σ²(Fo²)+(0.0348P)²+6.1937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1917
_reflns_number_total             3343
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc07101b2.cif
_cod_data_source_block           RD010_6
_cod_depositor_comments
'Adding full bibliography for 7122556--7122558.cif.'
_cod_original_cell_volume        4073.3(12)
_cod_database_code               7122557
_shelx_shelxl_version_number     2018/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.705
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Zn1 Zn 0.000000 0.56274(8) 0.250000 0.0258(3) Uani 1 2 d S T P
N1 N 0.06583(16) 0.6831(3) 0.2933(2) 0.0257(10) Uani 1 1 d . . .
N2 N 0.000000 0.8571(5) 0.250000 0.0289(14) Uani 1 2 d S T P
N3 N 0.02794(15) 0.4418(4) 0.1818(2) 0.0257(9) Uani 1 1 d . . .
N4 N 0.000000 0.2676(5) 0.250000 0.0343(16) Uani 1 2 d S T P
C1 C 0.0525(2) 0.8059(4) 0.2901(3) 0.0286(12) Uani 1 1 d . . .
C2 C 0.1076(2) 0.8709(4) 0.3307(3) 0.0277(12) Uani 1 1 d . . .
C3 C 0.1198(2) 0.9903(4) 0.3543(3) 0.0306(13) Uani 1 1 d . . .
H3 H 0.088773 1.048869 0.338623 0.037 Uiso 1 1 calc R U .
C4 C 0.1784(2) 1.0189(5) 0.4011(3) 0.0345(13) Uani 1 1 d . . .
H4 H 0.187402 1.098985 0.419000 0.041 Uiso 1 1 calc R U .
C5 C 0.2246(2) 0.9375(5) 0.4232(3) 0.0340(12) Uani 1 1 d . . .
H5 H 0.264522 0.962427 0.454820 0.041 Uiso 1 1 calc R U .
C6 C 0.2138(2) 0.8189(4) 0.3998(3) 0.0309(12) Uani 1 1 d . . .
H6 H 0.245721 0.762218 0.414798 0.037 Uiso 1 1 calc R U .
C7 C 0.1547(2) 0.7859(4) 0.3538(3) 0.0274(12) Uani 1 1 d . . .
C8 C 0.1268(2) 0.6723(4) 0.3287(3) 0.0271(12) Uani 1 1 d . . .
C9 C 0.15700(19) 0.5558(5) 0.3345(3) 0.0289(11) Uani 1 1 d . . .
C10 C 0.2097(2) 0.5468(5) 0.3118(3) 0.0361(13) Uani 1 1 d . . .
H10 H 0.227948 0.616407 0.298432 0.043 Uiso 1 1 calc R U .
C11 C 0.2354(2) 0.4370(6) 0.3086(3) 0.0489(14) Uani 1 1 d . . .
H11 H 0.271169 0.430904 0.292871 0.059 Uiso 1 1 calc R U .
C12 C 0.2088(3) 0.3360(5) 0.3284(4) 0.0515(16) Uani 1 1 d . . .
H12 H 0.225962 0.260277 0.325296 0.062 Uiso 1 1 calc R U .
C13 C 0.1581(2) 0.3444(5) 0.3524(3) 0.0428(15) Uani 1 1 d . . .
H13 H 0.140287 0.274548 0.366349 0.051 Uiso 1 1 calc R U .
C14 C 0.1324(2) 0.4538(5) 0.3567(3) 0.0358(13) Uani 1 1 d . . .
H14 H 0.097652 0.458994 0.374897 0.043 Uiso 1 1 calc R U .
C15 C 0.0263(2) 0.3203(4) 0.1999(3) 0.0272(12) Uani 1 1 d . . .
C16 C 0.0605(2) 0.2566(5) 0.1560(3) 0.0324(13) Uani 1 1 d . . .
C17 C 0.0723(2) 0.1347(5) 0.1515(3) 0.0398(14) Uani 1 1 d . . .
H17 H 0.055550 0.077635 0.180196 0.048 Uiso 1 1 calc R U .
C18 C 0.1086(2) 0.1010(5) 0.1046(3) 0.0439(15) Uani 1 1 d . . .
H18 H 0.118681 0.019467 0.103132 0.053 Uiso 1 1 calc R U .
C19 C 0.1310(2) 0.1821(5) 0.0592(3) 0.0469(16) Uani 1 1 d . . .
H19 H 0.154559 0.154601 0.025229 0.056 Uiso 1 1 calc R U .
C20 C 0.1198(2) 0.3030(5) 0.0623(3) 0.0389(14) Uani 1 1 d . . .
H20 H 0.135328 0.358525 0.031022 0.047 Uiso 1 1 calc R U .
C21 C 0.0849(2) 0.3403(5) 0.1129(3) 0.0315(13) Uani 1 1 d . . .
C22 C 0.06314(19) 0.4550(4) 0.1304(3) 0.0283(12) Uani 1 1 d . . .
C23 C 0.0741(2) 0.5701(5) 0.0980(3) 0.0299(12) Uani 1 1 d . . .
C24 C 0.1304(2) 0.5957(5) 0.0883(3) 0.0381(14) Uani 1 1 d . . .
H24 H 0.161678 0.537721 0.104318 0.046 Uiso 1 1 calc R U .
C25 C 0.1413(3) 0.7020(6) 0.0564(3) 0.0480(16) Uani 1 1 d . . .
H25 H 0.179846 0.717871 0.050556 0.058 Uiso 1 1 calc R U .
C26 C 0.0957(3) 0.7873(5) 0.0324(3) 0.0525(17) Uani 1 1 d . . .
H26 H 0.102362 0.860131 0.007473 0.063 Uiso 1 1 calc R U .
C27 C 0.0409(3) 0.7657(5) 0.0449(3) 0.0470(15) Uani 1 1 d . . .
H27 H 0.010480 0.825335 0.031374 0.056 Uiso 1 1 calc R U .
C28 C 0.0300(2) 0.6571(5) 0.0772(3) 0.0358(13) Uani 1 1 d . . .
H28 H -0.008096 0.642602 0.085094 0.043 Uiso 1 1 calc R U .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
N3 Zn1 N3 94.1(2) . 2
N3 Zn1 N1 108.11(14) . .
N3 Zn1 N1 127.81(14) 2 .
N3 Zn1 N1 127.81(14) . 2
N3 Zn1 N1 108.11(14) 2 2
N1 Zn1 N1 94.6(2) . 2
C8 N1 C1 107.0(4) . .
C8 N1 Zn1 132.0(3) . .
C1 N1 Zn1 121.0(3) . .
C1 N2 C1 128.2(6) . 2
C22 N3 C15 107.5(4) . .
C22 N3 Zn1 129.9(3) . .
C15 N3 Zn1 120.6(3) . .
C15 N4 C15 126.3(6) . 2
N2 C1 N1 127.1(5) . .
N2 C1 C2 123.6(5) . .
N1 C1 C2 109.1(4) . .
C3 C2 C7 120.2(5) . .
C3 C2 C1 133.3(5) . .
C7 C2 C1 106.3(4) . .
C4 C3 C2 117.1(5) . .
C4 C3 H3 121.4 . .
C2 C3 H3 121.4 . .
C5 C4 C3 123.1(5) . .
C5 C4 H4 118.4 . .
C3 C4 H4 118.4 . .
C4 C5 C6 120.8(5) . .
C4 C5 H5 119.6 . .
C6 C5 H5 119.6 . .
C5 C6 C7 117.8(4) . .
C5 C6 H6 121.1 . .
C7 C6 H6 121.1 . .
C6 C7 C2 120.9(5) . .
C6 C7 C8 132.2(5) . .
C2 C7 C8 106.6(4) . .
N1 C8 C7 110.9(4) . .
N1 C8 C9 121.3(4) . .
C7 C8 C9 127.7(4) . .
C14 C9 C10 118.9(5) . .
C14 C9 C8 121.7(4) . .
C10 C9 C8 119.2(5) . .
C11 C10 C9 120.3(5) . .
C11 C10 H10 119.9 . .
C9 C10 H10 119.9 . .
C10 C11 C12 119.6(5) . .
C10 C11 H11 120.2 . .
C12 C11 H11 120.2 . .
C13 C12 C11 120.4(5) . .
C13 C12 H12 119.8 . .
C11 C12 H12 119.8 . .
C12 C13 C14 120.4(5) . .
C12 C13 H13 119.8 . .
C14 C13 H13 119.8 . .
C13 C14 C9 120.3(5) . .
C13 C14 H14 119.8 . .
C9 C14 H14 119.8 . .
N4 C15 N3 128.5(4) . .
N4 C15 C16 122.5(5) . .
N3 C15 C16 109.0(4) . .
C21 C16 C17 120.9(5) . .
C21 C16 C15 107.4(4) . .
C17 C16 C15 131.7(5) . .
C18 C17 C16 117.7(5) . .
C18 C17 H17 121.1 . .
C16 C17 H17 121.1 . .
C17 C18 C19 122.0(5) . .
C17 C18 H18 119.0 . .
C19 C18 H18 119.0 . .
C18 C19 C20 121.3(5) . .
C18 C19 H19 119.4 . .
C20 C19 H19 119.4 . .
C19 C20 C21 117.8(5) . .
C19 C20 H20 121.1 . .
C21 C20 H20 121.1 . .
C20 C21 C16 120.2(5) . .
C20 C21 C22 133.8(5) . .
C16 C21 C22 105.9(4) . .
N3 C22 C21 110.1(4) . .
N3 C22 C23 122.4(4) . .
C21 C22 C23 127.4(4) . .
C28 C23 C24 118.4(5) . .
C28 C23 C22 121.2(4) . .
C24 C23 C22 120.4(5) . .
C25 C24 C23 121.4(5) . .
C25 C24 H24 119.3 . .
C23 C24 H24 119.3 . .
C24 C25 C26 119.8(5) . .
C24 C25 H25 120.1 . .
C26 C25 H25 120.1 . .
C27 C26 C25 119.6(5) . .
C27 C26 H26 120.2 . .
C25 C26 H26 120.2 . .
C26 C27 C28 120.4(5) . .
C26 C27 H27 119.8 . .
C28 C27 H27 119.8 . .
C23 C28 C27 120.4(5) . .
C23 C28 H28 119.8 . .
C27 C28 H28 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N3 1.998(4) .
Zn1 N3 1.998(4) 2
Zn1 N1 1.999(4) .
Zn1 N1 1.999(4) 2
N1 C8 1.357(5) .
N1 C1 1.414(6) .
N2 C1 1.321(5) .
N2 C1 1.321(5) 2
N3 C22 1.359(5) .
N3 C15 1.403(6) .
N4 C15 1.313(5) .
N4 C15 1.313(5) 2
C1 C2 1.441(6) .
C2 C3 1.403(6) .
C2 C7 1.413(6) .
C3 C4 1.374(6) .
C3 H3 0.9500 .
C4 C5 1.371(6) .
C4 H4 0.9500 .
C5 C6 1.389(7) .
C5 H5 0.9500 .
C6 C7 1.393(6) .
C6 H6 0.9500 .
C7 C8 1.433(6) .
C8 C9 1.476(6) .
C9 C14 1.383(6) .
C9 C10 1.396(6) .
C10 C11 1.382(7) .
C10 H10 0.9500 .
C11 C12 1.382(7) .
C11 H11 0.9500 .
C12 C13 1.362(7) .
C12 H12 0.9500 .
C13 C14 1.380(7) .
C13 H13 0.9500 .
C14 H14 0.9500 .
C15 C16 1.427(6) .
C16 C21 1.402(7) .
C16 C17 1.406(7) .
C17 C18 1.367(6) .
C17 H17 0.9500 .
C18 C19 1.381(7) .
C18 H18 0.9500 .
C19 C20 1.390(7) .
C19 H19 0.9500 .
C20 C21 1.399(6) .
C20 H20 0.9500 .
C21 C22 1.449(6) .
C22 C23 1.454(7) .
C23 C28 1.382(6) .
C23 C24 1.400(6) .
C24 C25 1.362(7) .
C24 H24 0.9500 .
C25 C26 1.391(8) .
C25 H25 0.9500 .
C26 C27 1.378(7) .
C26 H26 0.9500 .
C27 C28 1.387(7) .
C27 H27 0.9500 .
C28 H28 0.9500 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
C1 N2 C1 N1 5.7(3) 2
C1 N2 C1 C2 178.9(5) 2
C8 N1 C1 N2 170.0(4) .
Zn1 N1 C1 N2 -9.9(6) .
C8 N1 C1 C2 -4.0(5) .
Zn1 N1 C1 C2 176.1(3) .
N2 C1 C2 C3 14.4(8) .
N1 C1 C2 C3 -171.3(5) .
N2 C1 C2 C7 -170.9(4) .
N1 C1 C2 C7 3.4(5) .
C7 C2 C3 C4 -1.0(7) .
C1 C2 C3 C4 173.1(5) .
C2 C3 C4 C5 1.6(7) .
C3 C4 C5 C6 -1.0(7) .
C4 C5 C6 C7 -0.3(7) .
C5 C6 C7 C2 0.9(7) .
C5 C6 C7 C8 -171.8(5) .
C3 C2 C7 C6 -0.2(7) .
C1 C2 C7 C6 -175.8(4) .
C3 C2 C7 C8 174.1(4) .
C1 C2 C7 C8 -1.4(5) .
C1 N1 C8 C7 3.1(5) .
Zn1 N1 C8 C7 -177.0(3) .
C1 N1 C8 C9 -174.5(4) .
Zn1 N1 C8 C9 5.4(6) .
C6 C7 C8 N1 172.4(5) .
C2 C7 C8 N1 -1.1(5) .
C6 C7 C8 C9 -10.2(8) .
C2 C7 C8 C9 176.3(4) .
N1 C8 C9 C14 -40.7(6) .
C7 C8 C9 C14 142.1(5) .
N1 C8 C9 C10 135.1(5) .
C7 C8 C9 C10 -42.1(7) .
C14 C9 C10 C11 2.3(7) .
C8 C9 C10 C11 -173.6(4) .
C9 C10 C11 C12 -0.3(7) .
C10 C11 C12 C13 -1.1(8) .
C11 C12 C13 C14 0.5(8) .
C12 C13 C14 C9 1.6(7) .
C10 C9 C14 C13 -2.9(7) .
C8 C9 C14 C13 172.9(4) .
C15 N4 C15 N3 -6.4(4) 2
C15 N4 C15 C16 171.8(5) 2
C22 N3 C15 N4 176.7(4) .
Zn1 N3 C15 N4 11.0(6) .
C22 N3 C15 C16 -1.6(5) .
Zn1 N3 C15 C16 -167.3(3) .
N4 C15 C16 C21 -176.5(4) .
N3 C15 C16 C21 1.9(5) .
N4 C15 C16 C17 2.6(8) .
N3 C15 C16 C17 -178.9(5) .
C21 C16 C17 C18 0.5(7) .
C15 C16 C17 C18 -178.5(5) .
C16 C17 C18 C19 -3.1(8) .
C17 C18 C19 C20 2.9(8) .
C18 C19 C20 C21 0.0(8) .
C19 C20 C21 C16 -2.4(7) .
C19 C20 C21 C22 -178.5(5) .
C17 C16 C21 C20 2.2(7) .
C15 C16 C21 C20 -178.5(4) .
C17 C16 C21 C22 179.3(4) .
C15 C16 C21 C22 -1.4(5) .
C15 N3 C22 C21 0.7(5) .
Zn1 N3 C22 C21 164.6(3) .
C15 N3 C22 C23 179.1(4) .
Zn1 N3 C22 C23 -16.9(6) .
C20 C21 C22 N3 177.0(5) .
C16 C21 C22 N3 0.5(5) .
C20 C21 C22 C23 -1.4(9) .
C16 C21 C22 C23 -177.9(4) .
N3 C22 C23 C28 -34.4(7) .
C21 C22 C23 C28 143.8(5) .
N3 C22 C23 C24 144.7(4) .
C21 C22 C23 C24 -37.1(7) .
C28 C23 C24 C25 -2.2(7) .
C22 C23 C24 C25 178.6(4) .
C23 C24 C25 C26 -0.3(8) .
C24 C25 C26 C27 3.1(8) .
C25 C26 C27 C28 -3.3(8) .
C24 C23 C28 C27 2.0(7) .
C22 C23 C28 C27 -178.8(4) .
C26 C27 C28 C23 0.7(8) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189282
