#------------------------------------------------------------------------------
#$Date: 2019-10-17 02:57:29 +0200 (jue 17 de oct de 2019) $
#$Revision: 219390 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/13/7701384.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_7701384
loop_
_publ_author_name
'Mo, Kai-Qiang'
'Zhu, Zhonghong'
'Wang, Hai-Ling'
'Ma, Xiong-Feng'
'Peng, Jin-Mei'
'Zou, Hua-Hong'
'Bai, Juan'
'Liang, Fu-Pei'
_publ_section_title
;
 Substituents Lead to Differences in the Formation of Two Different
 Butterfly-shaped NiⅡ2DyⅢ2 Clusters: Structures and
 Multistep Assembly Mechanisms
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/C9DT03795K
_journal_year                    2019
_chemical_formula_moiety         'C40 H48 N16 Na2 Ni2 O8'
_chemical_formula_sum            'C40 H48 N16 Na2 Ni2 O8'
_chemical_formula_weight         1044.34
_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
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-15 deposited with the CCDC.    2019-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 123.044(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   24.989(6)
_cell_length_b                   11.319(3)
_cell_length_c                   20.032(5)
_cell_measurement_reflns_used    6290
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.77
_cell_measurement_theta_min      2.43
_cell_volume                     4750(2)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            26872
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.94
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'red brown'
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stripe
_exptl_crystal_F_000             2168
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4645
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.365
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0718P)²+7.7188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1383
_reflns_number_gt                3543
_reflns_number_total             4645
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c9dt03795k2.cif
_cod_data_source_block           1
_cod_database_code               7701384
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1-Na1
 2 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C9(H9a,H9b), C19(H19a,H19b)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C13(H13), C14(H14), C15(H15), C17(H17)
3.c Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C10(H10a,H10b,H10c), C18(H18a,H18b,H18c), C20(H20a,H20b,H20c)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 '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_calc_flag
_atom_site_refinement_flags_posn
Ni1 Ni 0.62655(2) 0.19857(5) 0.27409(3) 0.0344(2) Uani 1 d .
Na1 Na 0.53423(7) 0.27180(15) 0.34058(9) 0.0369(4) Uani 1 d D
O1 O 0.62496(13) 0.1748(2) 0.36781(16) 0.0345(6) Uani 1 d .
O2 O 0.58457(14) 0.1622(3) 0.46326(17) 0.0469(8) Uani 1 d .
O3 O 0.57155(12) 0.3334(2) 0.25239(16) 0.0327(6) Uani 1 d .
O4 O 0.47785(13) 0.4783(3) 0.15082(16) 0.0394(7) Uani 1 d .
N1 N 0.67459(16) 0.0550(4) 0.2907(2) 0.0438(9) Uani 1 d .
N2 N 0.70337(15) 0.2932(3) 0.3398(2) 0.0405(9) Uani 1 d .
N3 N 0.61920(19) 0.2326(4) 0.1745(2) 0.0511(10) Uani 1 d .
N6 N 0.54565(15) 0.1117(3) 0.2129(2) 0.0393(8) Uani 1 d .
N7 N 0.54254(17) 0.0215(4) 0.1820(2) 0.0500(10) Uani 1 d .
N8 N 0.5374(3) -0.0655(5) 0.1486(4) 0.099(2) Uani 1 d .
C1 C 0.63355(18) 0.0746(4) 0.4045(2) 0.0349(9) Uani 1 d D
C2 C 0.6141(2) 0.0621(4) 0.4585(2) 0.0418(10) Uani 1 d .
C3 C 0.6242(3) -0.0420(5) 0.5010(3) 0.0594(14) Uani 1 d .
H3 H 0.6102 -0.0482 0.5355 0.071 Uiso 1 calc R
C4 C 0.6553(3) -0.1371(5) 0.4917(3) 0.0692(16) Uani 1 d .
H4 H 0.6626 -0.2061 0.5207 0.083 Uiso 1 calc R
C5 C 0.6746(3) -0.1292(5) 0.4409(3) 0.0625(15) Uani 1 d .
H5 H 0.6951 -0.1932 0.4352 0.075 Uiso 1 calc R
C6 C 0.6642(2) -0.0255(4) 0.3961(3) 0.0432(10) Uani 1 d .
C7 C 0.6846(2) -0.0248(4) 0.3413(3) 0.0461(11) Uani 1 d .
H7 H 0.7078 -0.0903 0.3429 0.055 Uiso 1 calc R
C8 C 0.6996(3) 0.0314(6) 0.2403(4) 0.0743(18) Uani 1 d .
H8A H 0.6651 0.0313 0.1853 0.111 Uiso 1 calc GR
H8B H 0.7204 -0.0442 0.2538 0.111 Uiso 1 calc GR
H8C H 0.7297 0.0917 0.2488 0.111 Uiso 1 calc GR
C9 C 0.5583(3) 0.1561(6) 0.5118(3) 0.0701(17) Uani 1 d .
H9A H 0.5920 0.1409 0.5668 0.084 Uiso 1 calc R
H9B H 0.5273 0.0926 0.4935 0.084 Uiso 1 calc R
C10 C 0.5272(3) 0.2711(8) 0.5051(4) 0.093(2) Uani 1 d .
H10A H 0.4957 0.2874 0.4501 0.139 Uiso 1 calc GR
H10B H 0.5588 0.3326 0.5265 0.139 Uiso 1 calc GR
H10C H 0.5070 0.2676 0.5343 0.139 Uiso 1 calc GR
C11 C 0.58764(18) 0.4431(4) 0.2464(2) 0.0331(9) Uani 1 d .
C12 C 0.53878(19) 0.5252(4) 0.1971(2) 0.0366(9) Uani 1 d .
C13 C 0.5528(2) 0.6431(4) 0.1970(3) 0.0493(11) Uani 1 d .
H13 H 0.5200 0.6967 0.1667 0.059 Uiso 1 calc R
C14 C 0.6163(3) 0.6826(4) 0.2423(3) 0.0602(14) Uani 1 d .
H14 H 0.6255 0.7620 0.2415 0.072 Uiso 1 calc R
C15 C 0.6644(2) 0.6049(4) 0.2875(3) 0.0540(12) Uani 1 d .
H15 H 0.7064 0.6316 0.3171 0.065 Uiso 1 calc R
C16 C 0.6512(2) 0.4841(4) 0.2896(3) 0.0398(10) Uani 1 d .
C17 C 0.70387(19) 0.4064(4) 0.3390(3) 0.0442(11) Uani 1 d .
H17 H 0.7428 0.4425 0.3746 0.053 Uiso 1 calc R
C18 C 0.7633(2) 0.2337(5) 0.4009(3) 0.0637(15) Uani 1 d .
H18A H 0.7556 0.1864 0.4345 0.096 Uiso 1 calc GR
H18B H 0.7952 0.2920 0.4325 0.096 Uiso 1 calc GR
H18C H 0.7780 0.1841 0.3752 0.096 Uiso 1 calc GR
C19 C 0.4269(2) 0.5576(4) 0.0983(3) 0.0540(12) Uani 1 d .
H19A H 0.4383 0.6015 0.0662 0.065 Uiso 1 calc R
H19B H 0.4194 0.6135 0.1291 0.065 Uiso 1 calc R
C20 C 0.3676(2) 0.4851(5) 0.0455(3) 0.0607(14) Uani 1 d .
H20A H 0.3741 0.4356 0.0116 0.091 Uiso 1 calc GR
H20B H 0.3321 0.5369 0.0134 0.091 Uiso 1 calc GR
H20C H 0.3589 0.4368 0.0779 0.091 Uiso 1 calc GR
N4 N 0.6544(3) 0.2851(5) 0.1654(3) 0.0713(15) Uani 1 d .
N5 N 0.6888(4) 0.3307(8) 0.1520(5) 0.158(4) Uani 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Na Na 0.0362 0.0249 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 '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 Ni1 Na1 92.70(9) . 2_655
O1 Ni1 O3 86.54(12) . .
O1 Ni1 N1 93.17(14) . .
O1 Ni1 N2 87.43(14) . .
O1 Ni1 N3 173.49(15) . .
O1 Ni1 N6 88.66(14) . .
O3 Ni1 Na1 40.53(8) . 2_655
O3 Ni1 N1 174.80(14) . .
O3 Ni1 N2 92.02(13) . .
O3 Ni1 N3 87.41(16) . .
O3 Ni1 N6 83.78(13) . .
N1 Ni1 Na1 134.35(11) . 2_655
N1 Ni1 N2 93.16(15) . .
N1 Ni1 N3 92.63(18) . .
N1 Ni1 N6 91.02(15) . .
N2 Ni1 Na1 132.32(11) . 2_655
N2 Ni1 N6 174.43(15) . .
N3 Ni1 Na1 81.12(12) . 2_655
N3 Ni1 N2 95.20(16) . .
N3 Ni1 N6 88.27(16) . .
N6 Ni1 Na1 43.94(11) . 2_655
O1 Na1 O2 67.24(11) . .
O1 Na1 O3 66.59(10) . .
O1 Na1 O3 149.62(12) . 2_655
O1 Na1 O4 126.90(12) . 2_655
O1 Na1 N6 102.21(12) . 2_655
O2 Na1 O3 132.51(11) . .
O2 Na1 N6 85.04(12) . 2_655
O3 Na1 O2 134.02(12) 2_655 .
O3 Na1 O3 92.79(11) 2_655 .
O3 Na1 O4 68.56(10) 2_655 2_655
O3 Na1 N6 65.27(11) 2_655 2_655
O4 Na1 O2 116.71(13) 2_655 .
O4 Na1 O3 83.56(11) 2_655 .
O4 Na1 N6 130.53(12) 2_655 2_655
N6 Na1 O3 115.00(12) 2_655 .
Ni1 O1 Na1 104.15(12) . .
C1 O1 Ni1 126.1(3) . .
C1 O1 Na1 112.7(2) . .
C2 O2 Na1 110.7(2) . .
C2 O2 C9 117.6(4) . .
C9 O2 Na1 122.5(3) . .
Ni1 O3 Na1 96.52(11) . .
Ni1 O3 Na1 107.22(12) . 2_655
Na1 O3 Na1 77.69(10) 2_655 .
C11 O3 Ni1 122.9(2) . .
C11 O3 Na1 124.8(2) . .
C11 O3 Na1 117.9(2) . 2_655
C12 O4 Na1 117.7(2) . 2_655
C12 O4 C19 117.4(3) . .
C19 O4 Na1 124.8(3) . 2_655
C7 N1 Ni1 124.4(3) . .
C7 N1 C8 116.3(4) . .
C8 N1 Ni1 119.2(3) . .
C17 N2 Ni1 123.6(3) . .
C17 N2 C18 116.9(4) . .
C18 N2 Ni1 119.1(3) . .
N4 N3 Ni1 127.7(4) . .
Ni1 N6 Na1 102.54(15) . 2_655
N7 N6 Ni1 120.9(3) . .
N7 N6 Na1 127.2(3) . 2_655
N8 N7 N6 177.1(5) . .
O1 C1 C2 119.9(4) . .
O1 C1 C6 123.9(4) . .
C2 C1 C6 116.2(4) . .
O2 C2 C1 112.9(4) . .
O2 C2 C3 125.2(4) . .
C3 C2 C1 121.9(5) . .
C2 C3 H3 120.0 . .
C2 C3 C4 119.9(5) . .
C4 C3 H3 120.0 . .
C3 C4 H4 119.9 . .
C5 C4 C3 120.2(5) . .
C5 C4 H4 119.9 . .
C4 C5 H5 119.4 . .
C4 C5 C6 121.2(5) . .
C6 C5 H5 119.4 . .
C1 C6 C7 121.4(4) . .
C5 C6 C1 120.6(5) . .
C5 C6 C7 118.0(5) . .
N1 C7 C6 127.7(4) . .
N1 C7 H7 116.2 . .
C6 C7 H7 116.2 . .
N1 C8 H8A 109.5 . .
N1 C8 H8B 109.5 . .
N1 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
O2 C9 H9A 110.1 . .
O2 C9 H9B 110.1 . .
O2 C9 C10 107.8(5) . .
H9A C9 H9B 108.5 . .
C10 C9 H9A 110.1 . .
C10 C9 H9B 110.1 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10B 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
O3 C11 C12 119.1(3) . .
O3 C11 C16 123.1(4) . .
C16 C11 C12 117.7(4) . .
O4 C12 C11 115.4(3) . .
C13 C12 O4 123.8(4) . .
C13 C12 C11 120.8(4) . .
C12 C13 H13 119.8 . .
C12 C13 C14 120.4(5) . .
C14 C13 H13 119.8 . .
C13 C14 H14 119.9 . .
C15 C14 C13 120.1(4) . .
C15 C14 H14 119.9 . .
C14 C15 H15 119.7 . .
C14 C15 C16 120.6(4) . .
C16 C15 H15 119.7 . .
C11 C16 C15 120.2(4) . .
C11 C16 C17 121.6(4) . .
C15 C16 C17 118.1(4) . .
N2 C17 C16 127.5(4) . .
N2 C17 H17 116.3 . .
C16 C17 H17 116.3 . .
N2 C18 H18A 109.5 . .
N2 C18 H18B 109.5 . .
N2 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
O4 C19 H19A 110.1 . .
O4 C19 H19B 110.1 . .
O4 C19 C20 108.2(4) . .
H19A C19 H19B 108.4 . .
C20 C19 H19A 110.1 . .
C20 C19 H19B 110.1 . .
C19 C20 H20A 109.5 . .
C19 C20 H20B 109.5 . .
C19 C20 H20C 109.5 . .
H20A C20 H20B 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
N5 N4 N3 174.5(6) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ni1 Na1 3.4700(18) 2_655
Ni1 O1 1.918(3) .
Ni1 O3 1.938(3) .
Ni1 N1 1.938(4) .
Ni1 N2 1.952(3) .
Ni1 N3 1.940(4) .
Ni1 N6 1.963(3) .
Na1 O1 2.301(3) .
Na1 O2 2.406(3) .
Na1 O3 2.505(3) .
Na1 O3 2.361(3) 2_655
Na1 O4 2.375(3) 2_655
Na1 N6 2.467(4) 2_655
O1 C1 1.303(5) .
O2 C2 1.383(6) .
O2 C9 1.440(5) .
O3 Na1 2.361(3) 2_655
O3 C11 1.330(5) .
O4 Na1 2.375(3) 2_655
O4 C12 1.386(5) .
O4 C19 1.439(5) .
N1 C7 1.276(6) .
N1 C8 1.475(6) .
N2 C17 1.281(6) .
N2 C18 1.483(6) .
N3 N4 1.155(6) .
N6 Na1 2.467(4) 2_655
N6 N7 1.175(5) .
N7 N8 1.157(6) .
C1 C2 1.415(6) .
C1 C6 1.429(6) .
C2 C3 1.394(7) .
C3 H3 0.9300 .
C3 C4 1.398(8) .
C4 H4 0.9300 .
C4 C5 1.346(8) .
C5 H5 0.9300 .
C5 C6 1.413(7) .
C6 C7 1.441(7) .
C7 H7 0.9300 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C9 C10 1.484(10) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 C12 1.420(6) .
C11 C16 1.409(5) .
C12 C13 1.380(6) .
C13 H13 0.9300 .
C13 C14 1.403(7) .
C14 H14 0.9300 .
C14 C15 1.361(7) .
C15 H15 0.9300 .
C15 C16 1.414(6) .
C16 C17 1.437(6) .
C17 H17 0.9300 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9700 .
C19 H19B 0.9700 .
C19 C20 1.510(7) .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
N4 N5 1.154(7) .
