#------------------------------------------------------------------------------
#$Date: 2019-06-05 06:55:19 +0300 (Wed, 05 Jun 2019) $
#$Revision: 215708 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/28/7232867.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_7232867
loop_
_publ_author_name
'Dong, Jun-Liang'
'Zhu, Peng-Yin'
'Du, Jia-Qiang'
'Xie, Fei'
'Lan, Hai-Ming'
'Yang, Ru-Xia'
'Yang, Li-Zheng'
'Wang, Duo-Zhi'
_publ_section_title
;
 Syntheses, structures, and magnetic properties of mixed-ligand complexes
 based on 3,6-bis(benzimidazol-1-yl)pyridazine
;
_journal_issue                   31
_journal_name_full               'RSC Advances'
_journal_page_first              17560
_journal_paper_doi               10.1039/C9RA03082D
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C30 H18 Mn N6 O4'
_chemical_formula_sum            'C30 H18 Mn N6 O4'
_chemical_formula_weight         581.44
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-11-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-10-18 deposited with the CCDC.    2019-05-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.215(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.035(3)
_cell_length_b                   9.024(2)
_cell_length_c                   24.497(6)
_cell_measurement_reflns_used    1403
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      21.885
_cell_measurement_theta_min      2.408
_cell_volume                     2420.1(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_av_unetI/netI     0.0923
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            21200
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_min         1.676
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0827 before and 0.0702 after correction. The Ratio of minimum to maximum transmission is 0.8904. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_description       block
_exptl_crystal_F_000             1188
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         5518
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0502
_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)+(0.0359P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1143
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3768
_reflns_number_total             5518
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9ra03082d2.cif
_cod_data_source_block           mo_2017970-yby-2_0m
_cod_original_cell_volume        2420.2(10)
_cod_database_code               7232867
_shelx_shelxl_version_number     2014/7
_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   0.905
_shelx_estimated_absorpt_t_min   0.875
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C14(H14),
 C15(H15), C16(H16), C17(H17), C21(H21), C22(H22), C26(H26), C27(H27), C28(H28),
  C29(H29)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Mn1 Mn 0.36437(3) 0.48144(5) 0.22029(2) 0.01376(12) Uani 1 1 d .
O1 O 0.55887(17) 0.5137(2) 0.22648(8) 0.0230(5) Uani 1 1 d .
O2 O 0.33369(16) 0.6972(2) 0.25185(8) 0.0186(4) Uani 1 1 d .
O3 O 0.98895(17) 0.7867(2) 0.30158(8) 0.0261(5) Uani 1 1 d .
O4 O 0.17601(16) 0.4140(2) 0.20569(8) 0.0190(4) Uani 1 1 d .
N1 N 0.3748(2) 0.3822(3) 0.30465(9) 0.0168(5) Uani 1 1 d .
N2 N 0.3368(2) 0.5352(3) 0.12933(9) 0.0198(5) Uani 1 1 d .
N3 N 0.2575(2) 0.5094(3) 0.04121(9) 0.0179(5) Uani 1 1 d .
N4 N 0.1190(2) 0.3298(3) 0.01045(9) 0.0262(6) Uani 1 1 d .
N5 N 0.0410(2) 0.2605(3) -0.02798(10) 0.0264(6) Uani 1 1 d .
N6 N -0.0545(2) 0.2300(3) -0.11647(9) 0.0169(5) Uani 1 1 d .
C1 C 0.2480(2) 0.4784(3) 0.09532(11) 0.0176(6) Uani 1 1 d .
H1 H 0.1835 0.4215 0.1069 0.021 Uiso 1 1 calc R
C2 C 0.3650(2) 0.5936(3) 0.04044(11) 0.0178(6) Uani 1 1 d .
C3 C 0.4237(3) 0.6499(3) -0.00151(12) 0.0230(7) Uani 1 1 d .
H3 H 0.3912 0.6382 -0.0391 0.028 Uiso 1 1 calc R
C4 C 0.5320(3) 0.7243(3) 0.01385(13) 0.0271(7) Uani 1 1 d .
H4 H 0.5752 0.7650 -0.0138 0.033 Uiso 1 1 calc R
C5 C 0.5796(3) 0.7412(3) 0.06888(13) 0.0281(7) Uani 1 1 d .
H5 H 0.6541 0.7935 0.0778 0.034 Uiso 1 1 calc R
C6 C 0.5209(3) 0.6835(3) 0.11115(13) 0.0252(7) Uani 1 1 d .
H6 H 0.5536 0.6953 0.1487 0.030 Uiso 1 1 calc R
C7 C 0.4126(2) 0.6083(3) 0.09614(11) 0.0176(6) Uani 1 1 d .
C8 C 0.1773(2) 0.4486(3) -0.00344(11) 0.0171(6) Uani 1 1 d .
C9 C 0.1613(3) 0.5116(3) -0.05555(12) 0.0235(7) Uani 1 1 d .
H9 H 0.2023 0.6001 -0.0635 0.028 Uiso 1 1 calc R
C10 C 0.0833(3) 0.4395(3) -0.09500(12) 0.0239(7) Uani 1 1 d .
H10 H 0.0690 0.4751 -0.1317 0.029 Uiso 1 1 calc R
C11 C 0.0265(2) 0.3130(3) -0.07907(11) 0.0175(6) Uani 1 1 d .
C12 C -0.0458(2) 0.2120(3) -0.17161(12) 0.0190(6) Uani 1 1 d .
H12 H 0.0120 0.2628 -0.1904 0.023 Uiso 1 1 calc R
C13 C -0.1497(2) 0.1368(3) -0.10391(11) 0.0162(6) Uani 1 1 d .
C14 C -0.1997(3) 0.1085(3) -0.05595(12) 0.0218(7) Uani 1 1 d .
H14 H -0.1694 0.1546 -0.0221 0.026 Uiso 1 1 calc R
C15 C -0.2966(3) 0.0092(3) -0.05973(12) 0.0262(7) Uani 1 1 d .
H15 H -0.3346 -0.0120 -0.0279 0.031 Uiso 1 1 calc R
C16 C -0.3394(3) -0.0603(3) -0.10943(12) 0.0232(7) Uani 1 1 d .
H16 H -0.4048 -0.1290 -0.1103 0.028 Uiso 1 1 calc R
C17 C -0.2895(2) -0.0320(3) -0.15733(11) 0.0173(6) Uani 1 1 d .
H17 H -0.3192 -0.0797 -0.1909 0.021 Uiso 1 1 calc R
C18 C -0.1935(2) 0.0695(3) -0.15420(11) 0.0159(6) Uani 1 1 d .
C19 C 0.3819(2) 0.8090(3) 0.27491(11) 0.0138(6) Uani 1 1 d .
C20 C 0.5193(2) 0.8271(3) 0.28060(11) 0.0141(6) Uani 1 1 d .
C21 C 0.5715(2) 0.9181(3) 0.24561(12) 0.0223(7) Uani 1 1 d .
H21 H 0.5208 0.9713 0.2181 0.027 Uiso 1 1 calc R
C22 C 0.6983(2) 0.9342(3) 0.24968(12) 0.0210(7) Uani 1 1 d .
H22 H 0.7320 0.9988 0.2249 0.025 Uiso 1 1 calc R
C23 C 0.7758(2) 0.8591(3) 0.28850(11) 0.0157(6) Uani 1 1 d .
C24 C 0.7252(2) 0.7639(3) 0.32627(11) 0.0139(6) Uani 1 1 d .
C25 C 0.5951(2) 0.7498(3) 0.32303(11) 0.0128(6) Uani 1 1 d .
C26 C 0.5441(3) 0.6658(3) 0.36325(11) 0.0187(6) Uani 1 1 d .
H26 H 0.4578 0.6597 0.3618 0.022 Uiso 1 1 calc R
C27 C 0.6164(3) 0.5933(3) 0.40432(12) 0.0231(7) Uani 1 1 d .
H27 H 0.5808 0.5377 0.4311 0.028 Uiso 1 1 calc R
C28 C 0.7446(3) 0.6024(3) 0.40628(12) 0.0225(7) Uani 1 1 d .
H28 H 0.7951 0.5500 0.4341 0.027 Uiso 1 1 calc R
C29 C 0.7973(2) 0.6850(3) 0.36894(11) 0.0182(6) Uani 1 1 d .
H29 H 0.8838 0.6900 0.3715 0.022 Uiso 1 1 calc R
C30 C 0.9108(2) 0.8860(3) 0.28866(11) 0.0187(6) 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'
Mn Mn 0.3368 0.7283 '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'
O O 0.0106 0.0060 '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
O1 Mn1 O3 56.08(7) . 2_645
O1 Mn1 N1 93.10(8) . .
O1 Mn1 N2 92.85(8) . .
O2 Mn1 O1 93.04(7) . .
O2 Mn1 O3 148.93(7) . 2_645
O2 Mn1 O4 97.13(7) . .
O2 Mn1 N1 91.29(8) . .
O2 Mn1 N2 98.81(8) . .
O4 Mn1 O1 169.64(8) . .
O4 Mn1 O3 113.87(7) . 2_645
O4 Mn1 N1 88.68(8) . .
O4 Mn1 N2 83.65(8) . .
N1 Mn1 O3 87.55(8) . 2_645
N1 Mn1 N2 167.98(9) . .
N2 Mn1 O3 87.13(8) . 2_645
C30 O1 Mn1 98.84(16) 2_645 .
C19 O2 Mn1 145.63(17) . .
C30 O3 Mn1 83.49(17) . 2_655
C19 O4 Mn1 132.11(16) 2_545 .
C12 N1 Mn1 128.7(2) 4_666 .
C12 N1 C18 105.9(2) 4_666 4_666
C18 N1 Mn1 124.70(17) 4_666 .
C1 N2 Mn1 122.70(19) . .
C1 N2 C7 105.6(2) . .
C7 N2 Mn1 130.95(17) . .
C1 N3 C2 106.8(2) . .
C1 N3 C8 123.2(2) . .
C2 N3 C8 129.6(2) . .
C8 N4 N5 119.1(2) . .
C11 N5 N4 118.9(2) . .
C12 N6 C11 125.7(2) . .
C12 N6 C13 106.8(2) . .
C13 N6 C11 127.1(2) . .
N2 C1 N3 113.2(2) . .
C3 C2 N3 133.1(2) . .
C3 C2 C7 122.4(3) . .
C7 C2 N3 104.5(2) . .
C2 C3 C4 116.6(3) . .
C3 C4 C5 121.6(3) . .
C6 C5 C4 121.8(3) . .
C7 C6 C5 117.0(3) . .
N2 C7 C2 109.9(2) . .
C6 C7 N2 129.4(3) . .
C6 C7 C2 120.6(3) . .
N4 C8 N3 113.0(2) . .
N4 C8 C9 124.2(2) . .
C9 C8 N3 122.8(2) . .
C10 C9 C8 116.6(3) . .
C9 C10 C11 117.3(3) . .
N5 C11 N6 114.4(2) . .
N5 C11 C10 123.7(2) . .
C10 C11 N6 121.8(2) . .
N1 C12 N6 112.9(3) 4_565 .
C14 C13 N6 133.1(2) . .
C14 C13 C18 122.4(3) . .
C18 C13 N6 104.5(2) . .
C13 C14 C15 116.7(3) . .
C14 C15 C16 121.3(3) . .
C17 C16 C15 122.0(3) . .
C16 C17 C18 117.1(2) . .
N1 C18 C13 109.9(2) 4_565 .
C17 C18 N1 129.6(2) . 4_565
C17 C18 C13 120.5(3) . .
O2 C19 O4 124.7(2) . 2
O2 C19 C20 119.8(2) . .
O4 C19 C20 115.5(2) 2 .
C21 C20 C19 120.2(2) . .
C21 C20 C25 119.6(2) . .
C25 C20 C19 120.1(2) . .
C20 C21 C22 121.0(3) . .
C23 C22 C21 121.9(3) . .
C22 C23 C24 119.1(2) . .
C22 C23 C30 116.7(3) . .
C24 C23 C30 124.2(2) . .
C23 C24 C25 119.2(2) . .
C29 C24 C23 123.3(2) . .
C29 C24 C25 117.4(3) . .
C20 C25 C24 119.1(2) . .
C26 C25 C20 121.3(2) . .
C26 C25 C24 119.5(2) . .
C27 C26 C25 121.4(3) . .
C26 C27 C28 119.1(3) . .
C29 C28 C27 121.2(3) . .
C28 C29 C24 121.3(3) . .
O1 C30 C23 116.2(2) 2_655 .
O3 C30 O1 121.6(3) . 2_655
O3 C30 C23 122.1(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Mn1 O1 2.152(2) .
Mn1 O2 2.1380(19) .
Mn1 O3 2.493(2) 2_645
Mn1 O4 2.1521(18) .
Mn1 N1 2.242(2) .
Mn1 N2 2.263(2) .
O1 C30 1.269(3) 2_645
O2 C19 1.243(3) .
O3 Mn1 2.493(2) 2_655
O3 C30 1.256(3) .
O4 C19 1.269(3) 2_545
N1 C12 1.304(3) 4_666
N1 C18 1.401(3) 4_666
N2 C1 1.308(3) .
N2 C7 1.402(4) .
N3 C1 1.372(3) .
N3 C2 1.411(3) .
N3 C8 1.428(3) .
N4 N5 1.347(3) .
N4 C8 1.317(4) .
N5 C11 1.329(4) .
N6 C11 1.412(3) .
N6 C12 1.376(3) .
N6 C13 1.410(3) .
C2 C3 1.379(4) .
C2 C7 1.405(4) .
C3 C4 1.382(4) .
C4 C5 1.392(4) .
C5 C6 1.390(4) .
C6 C7 1.383(4) .
C8 C9 1.388(4) .
C9 C10 1.375(4) .
C10 C11 1.382(4) .
C12 N1 1.304(3) 4_565
C13 C14 1.384(4) .
C13 C18 1.403(4) .
C14 C15 1.389(4) .
C15 C16 1.398(4) .
C16 C17 1.381(4) .
C17 C18 1.396(4) .
C18 N1 1.401(3) 4_565
C19 O4 1.269(3) 2
C19 C20 1.513(4) .
C20 C21 1.366(4) .
C20 C25 1.431(3) .
C21 C22 1.399(4) .
C22 C23 1.375(4) .
C23 C24 1.427(4) .
C23 C30 1.510(4) .
C24 C25 1.433(4) .
C24 C29 1.422(4) .
C25 C26 1.415(4) .
C26 C27 1.370(4) .
C27 C28 1.412(4) .
C28 C29 1.366(4) .
C30 O1 1.269(3) 2_655
