#------------------------------------------------------------------------------
#$Date: 2021-01-07 08:26:44 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260773 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/40/7704048.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_7704048
loop_
_publ_author_name
'Braun, Jason D.'
'Gray, Paul A.'
'Sidhu, Baldeep K.'
'Nemez, Dion B.'
'Herbert, David E.'
_publ_section_title
;
 Zn-Templated synthesis of substituted (2,6-diimine)pyridine proligands
 and evaluation of their iron complexes as anolytes for flow battery
 applications.
;
_journal_issue                   45
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              16175
_journal_page_last               16183
_journal_paper_doi               10.1039/d0dt00543f
_journal_volume                  49
_journal_year                    2020
_chemical_formula_moiety         'C23 H17 Cl2 N5 Zn, C2 H3 N'
_chemical_formula_sum            'C25 H20 Cl2 N6 Zn'
_chemical_formula_weight         540.74
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-18
_audit_creation_method
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-02-10 deposited with the CCDC.	2020-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.628(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7284(7)
_cell_length_b                   14.8601(13)
_cell_length_c                   22.4323(19)
_cell_measurement_reflns_used    9127
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.642
_cell_measurement_theta_min      2.659
_cell_volume                     2553.4(4)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 Quest ECO CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0966
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            66904
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.055
_diffrn_reflns_theta_min         2.659
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.196
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1015 before and 0.0767 after correction.
The Ratio of minimum to maximum transmission is 0.7681.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.854
_refine_diff_density_min         -1.036
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.219
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     310
_refine_ls_number_reflns         6121
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.219
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0656
_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)+(0.0190P)²+10.1397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1495
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4385
_reflns_number_total             6121
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0dt00543f2.cif
_cod_data_source_block           1d
_cod_depositor_comments
'Adding full bibliography for 7704046--7704050.cif.'
_cod_database_code               7704048
_shelx_shelxl_version_number     2018/3
_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_max   0.880
_shelx_estimated_absorpt_t_min   0.731
_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
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15), C18(H18),
 C19(H19), C21(H21), C22(H22)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C9(H9A,H9B,H9C), C24(H24A,H24B,H24C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4659(6) 0.4907(3) 0.1927(2) 0.0304(10) Uani 1 1 d . . . . .
C2 C 0.5309(7) 0.5568(4) 0.1512(2) 0.0413(12) Uani 1 1 d . . . . .
H2A H 0.431552 0.586053 0.127148 0.062 Uiso 1 1 calc GR . . . .
H2B H 0.601806 0.525635 0.124555 0.062 Uiso 1 1 calc GR . . . .
H2C H 0.602218 0.602317 0.174665 0.062 Uiso 1 1 calc GR . . . .
C3 C 0.3339(6) 0.5226(3) 0.2317(2) 0.0294(10) Uani 1 1 d . . . . .
C4 C 0.2574(6) 0.6067(4) 0.2273(2) 0.0388(12) Uani 1 1 d . . . . .
H4 H 0.286804 0.648865 0.198416 0.047 Uiso 1 1 calc R . . . .
C5 C 0.1375(7) 0.6288(4) 0.2654(3) 0.0441(13) Uani 1 1 d . . . . .
H5 H 0.081038 0.685675 0.262307 0.053 Uiso 1 1 calc R . . . .
C6 C 0.1007(6) 0.5669(3) 0.3081(2) 0.0364(12) Uani 1 1 d . . . . .
H6 H 0.018594 0.580989 0.334649 0.044 Uiso 1 1 calc R . . . .
C7 C 0.1853(5) 0.4835(3) 0.3118(2) 0.0297(10) Uani 1 1 d . . . . .
C8 C 0.1676(5) 0.4140(3) 0.3580(2) 0.0296(10) Uani 1 1 d . . . . .
C9 C 0.0574(6) 0.4342(4) 0.4061(2) 0.0362(11) Uani 1 1 d . . . . .
H9A H 0.087110 0.493952 0.422941 0.054 Uiso 1 1 calc GR . . . .
H9B H 0.078743 0.388907 0.438020 0.054 Uiso 1 1 calc GR . . . .
H9C H -0.066108 0.432984 0.389083 0.054 Uiso 1 1 calc GR . . . .
C10 C 0.6386(6) 0.3690(3) 0.1677(2) 0.0319(10) Uani 1 1 d . . . . .
C11 C 0.8127(6) 0.3962(4) 0.1782(2) 0.0412(13) Uani 1 1 d . . . . .
H11 H 0.847040 0.443287 0.205901 0.049 Uiso 1 1 calc R . . . .
C12 C 0.9345(7) 0.3542(4) 0.1481(3) 0.0464(14) Uani 1 1 d . . . . .
H12 H 1.053230 0.372533 0.155082 0.056 Uiso 1 1 calc R . . . .
C13 C 0.8848(7) 0.2853(4) 0.1077(2) 0.0407(12) Uani 1 1 d . . . . .
C14 C 0.7115(7) 0.2575(4) 0.0976(2) 0.0418(12) Uani 1 1 d . . . . .
H14 H 0.677436 0.210198 0.070044 0.050 Uiso 1 1 calc R . . . .
C15 C 0.5885(6) 0.2993(4) 0.1281(2) 0.0381(12) Uani 1 1 d . . . . .
H15 H 0.470280 0.280044 0.121843 0.046 Uiso 1 1 calc R . . . .
C16 C 1.0126(7) 0.2397(4) 0.0770(3) 0.0506(15) Uani 1 1 d . . . . .
C17 C 0.2488(6) 0.2688(3) 0.3937(2) 0.0304(10) Uani 1 1 d . . . . .
C18 C 0.0969(6) 0.2180(4) 0.3919(2) 0.0369(12) Uani 1 1 d . . . . .
H18 H -0.003213 0.233101 0.364447 0.044 Uiso 1 1 calc R . . . .
C19 C 0.0922(6) 0.1460(4) 0.4300(3) 0.0446(14) Uani 1 1 d . . . . .
H19 H -0.011152 0.111060 0.428901 0.054 Uiso 1 1 calc R . . . .
C20 C 0.2389(7) 0.1243(4) 0.4699(3) 0.0449(13) Uani 1 1 d . . . . .
C21 C 0.3915(6) 0.1743(4) 0.4711(2) 0.0385(12) Uani 1 1 d . . . . .
H21 H 0.492133 0.158600 0.498199 0.046 Uiso 1 1 calc R . . . .
C22 C 0.3965(6) 0.2465(3) 0.4330(2) 0.0333(11) Uani 1 1 d . . . . .
H22 H 0.500424 0.280851 0.433610 0.040 Uiso 1 1 calc R . . . .
C23 C 0.2344(8) 0.0505(6) 0.5112(4) 0.078(3) Uani 1 1 d . . . . .
Cl1 Cl 0.68198(13) 0.32456(9) 0.32822(5) 0.0360(3) Uani 1 1 d . . . . .
Cl2 Cl 0.28977(15) 0.21585(9) 0.22847(6) 0.0375(3) Uani 1 1 d . . . . .
N1 N 0.5104(5) 0.4080(3) 0.19958(17) 0.0309(9) Uani 1 1 d . . . . .
N2 N 0.2979(4) 0.4626(3) 0.27284(17) 0.0274(8) Uani 1 1 d . . . . .
N3 N 0.2563(4) 0.3420(3) 0.35350(17) 0.0292(8) Uani 1 1 d . . . . .
N4 N 1.1128(7) 0.2024(4) 0.0531(3) 0.0679(16) Uani 1 1 d . . . . .
N5 N 0.2313(8) -0.0068(6) 0.5443(4) 0.143(4) Uani 1 1 d . . . . .
Zn1 Zn 0.41353(6) 0.33572(4) 0.27661(2) 0.02745(15) Uani 1 1 d . . . . .
C24 C 1.4021(8) 0.0382(5) 0.0946(3) 0.0610(18) Uani 1 1 d . . . . .
H24A H 1.320165 0.088867 0.091841 0.092 Uiso 1 1 calc GR . . . .
H24B H 1.520194 0.060728 0.092242 0.092 Uiso 1 1 calc GR . . . .
H24C H 1.399899 0.006895 0.132897 0.092 Uiso 1 1 calc GR . . . .
C25 C 1.3518(8) -0.0235(5) 0.0454(3) 0.0553(16) Uani 1 1 d . . . . .
N6 N 1.3128(8) -0.0729(5) 0.0060(3) 0.0736(17) Uani 1 1 d . . . . .
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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
C2 C1 C3 117.8(4) . . ?
N1 C1 C2 127.0(5) . . ?
N1 C1 C3 115.1(4) . . ?
C4 C3 C1 124.1(5) . . ?
N2 C3 C1 114.2(4) . . ?
N2 C3 C4 121.7(4) . . ?
C5 C4 C3 119.2(5) . . ?
C4 C5 C6 119.1(5) . . ?
C5 C6 C7 119.5(5) . . ?
C6 C7 C8 125.0(4) . . ?
N2 C7 C6 120.1(5) . . ?
N2 C7 C8 114.9(4) . . ?
C7 C8 C9 118.7(4) . . ?
N3 C8 C7 115.3(4) . . ?
N3 C8 C9 125.9(5) . . ?
C11 C10 N1 121.2(5) . . ?
C15 C10 C11 120.4(5) . . ?
C15 C10 N1 118.3(4) . . ?
C12 C11 C10 119.5(5) . . ?
C11 C12 C13 120.4(5) . . ?
C12 C13 C14 120.2(5) . . ?
C12 C13 C16 120.7(5) . . ?
C14 C13 C16 119.1(5) . . ?
C15 C14 C13 119.6(5) . . ?
C10 C15 C14 119.9(5) . . ?
N4 C16 C13 178.9(7) . . ?
C18 C17 N3 120.2(4) . . ?
C22 C17 C18 120.6(5) . . ?
C22 C17 N3 119.2(4) . . ?
C19 C18 C17 119.8(4) . . ?
C18 C19 C20 119.7(5) . . ?
C19 C20 C21 120.5(5) . . ?
C19 C20 C23 120.4(5) . . ?
C21 C20 C23 119.2(5) . . ?
C22 C21 C20 119.9(5) . . ?
C21 C22 C17 119.5(4) . . ?
N5 C23 C20 179.1(11) . . ?
C1 N1 C10 121.7(4) . . ?
C1 N1 Zn1 116.1(3) . . ?
C10 N1 Zn1 121.3(3) . . ?
C3 N2 C7 120.4(4) . . ?
C3 N2 Zn1 120.2(3) . . ?
C7 N2 Zn1 119.4(3) . . ?
C8 N3 C17 121.5(4) . . ?
C8 N3 Zn1 116.5(3) . . ?
C17 N3 Zn1 121.9(3) . . ?
Cl1 Zn1 N1 93.02(10) . . ?
Cl2 Zn1 Cl1 119.88(5) . . ?
Cl2 Zn1 N1 100.05(11) . . ?
Cl2 Zn1 N3 99.47(11) . . ?
N2 Zn1 Cl1 116.75(10) . . ?
N2 Zn1 Cl2 123.28(10) . . ?
N2 Zn1 N1 73.80(15) . . ?
N2 Zn1 N3 73.72(15) . . ?
N3 Zn1 Cl1 99.49(10) . . ?
N3 Zn1 N1 147.44(15) . . ?
N6 C25 C24 179.5(7) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.486(7) . ?
C1 C3 1.504(6) . ?
C1 N1 1.280(6) . ?
C3 C4 1.381(7) . ?
C3 N2 1.339(6) . ?
C4 C5 1.380(7) . ?
C5 C6 1.384(8) . ?
C6 C7 1.399(7) . ?
C7 C8 1.481(7) . ?
C7 N2 1.348(6) . ?
C8 C9 1.492(6) . ?
C8 N3 1.281(6) . ?
C10 C11 1.395(7) . ?
C10 C15 1.386(7) . ?
C10 N1 1.421(6) . ?
C11 C12 1.379(7) . ?
C12 C13 1.387(8) . ?
C13 C14 1.392(7) . ?
C13 C16 1.446(7) . ?
C14 C15 1.388(7) . ?
C16 N4 1.142(7) . ?
C17 C18 1.392(6) . ?
C17 C22 1.387(6) . ?
C17 N3 1.419(6) . ?
C18 C19 1.372(7) . ?
C19 C20 1.387(7) . ?
C20 C21 1.391(7) . ?
C20 C23 1.438(9) . ?
C21 C22 1.376(7) . ?
C23 N5 1.132(9) . ?
Cl1 Zn1 2.2437(11) . ?
Cl2 Zn1 2.2316(13) . ?
N1 Zn1 2.245(4) . ?
N2 Zn1 2.084(4) . ?
N3 Zn1 2.240(4) . ?
C24 C25 1.448(10) . ?
C25 N6 1.157(9) . ?
