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#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/98/4509896.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_4509896
loop_
_publ_author_name
'Liu, Zun-qi'
'Kubo, Kazuya'
'Noro, Shin-ichiro'
'Akutagawa, Tomoyuki'
'Nakamura, Takayoshi'
_publ_section_title
;
 Design of Crystalline Spaces for Molecular Rotations in Crystals
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              537
_journal_paper_doi               10.1021/cg4013262
_journal_volume                  14
_journal_year                    2014
_chemical_formula_sum            'C16.5 H16 F0.5 N0.5 Ni0.5 O3 S5'
_chemical_formula_weight         468.45
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 132.2109(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.4415(11)
_cell_length_b                   9.1090(3)
_cell_length_c                   20.1583(9)
_cell_measurement_temperature    296(2)
_cell_volume                     4004.2(3)
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita,Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0335
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            18921
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    1.054
_exptl_absorpt_correction_T_max  0.9204
_exptl_absorpt_correction_T_min  0.6901
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1928
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.751
_refine_diff_density_min         -0.823
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.158
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0434
_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)+(0.0545P)²+13.9390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1635
_reflns_number_gt                2899
_reflns_number_total             4556
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg4013262_si_007.cif
_cod_data_source_block           3f4me
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_original_formula_sum        'C16.50 H16 F0.50 N0.50 Ni0.50 O3 S5'
_cod_database_code               4509896
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
S1 S 0.31169(6) -0.13433(17) 0.89026(11) 0.0793(5) Uani 1 1 d .
S2 S 0.21707(5) 0.03919(14) 0.72493(8) 0.0567(3) Uani 1 1 d .
S3 S 0.08514(5) 0.10329(13) 0.55448(8) 0.0516(3) Uani 1 1 d .
S4 S -0.04466(5) 0.15162(13) 0.38913(8) 0.0543(3) Uani 1 1 d .
S5 S -0.17914(5) 0.20075(14) 0.22757(9) 0.0628(4) Uani 1 1 d .
O1 O -0.01814(16) -0.3383(4) 0.3642(2) 0.0592(8) Uani 1 1 d .
O2 O 0.10229(16) -0.3159(4) 0.4308(2) 0.0593(8) Uani 1 1 d .
O3 O 0.12051(16) -0.3194(3) 0.3203(2) 0.0594(8) Uani 1 1 d .
C1 C 0.13740(18) 0.0051(5) 0.6505(3) 0.0483(10) Uani 1 1 d .
C2 C -0.1208(2) 0.1065(5) 0.3249(3) 0.0515(10) Uani 1 1 d .
C3 C 0.0000 0.4255(6) 0.2500 0.0494(15) Uani 1 2 d S
C4 C 0.2402(2) -0.0991(5) 0.8009(4) 0.0620(13) Uani 1 1 d .
C5 C 0.1557(2) -0.2213(5) 0.3906(3) 0.0549(11) Uani 1 1 d .
C6 C 0.0339(3) -0.4002(6) 0.4482(3) 0.0642(13) Uani 1 1 d .
H1 H 0.0411 -0.4994 0.4395 0.077 Uiso 1 1 calc R
H2 H 0.0268 -0.4037 0.4887 0.077 Uiso 1 1 calc R
C7 C 0.1247(3) -0.3107(6) 0.2534(4) 0.0662(13) Uani 1 1 d .
H3 H 0.1646 -0.3454 0.2780 0.079 Uiso 1 1 calc R
H4 H 0.1200 -0.2097 0.2345 0.079 Uiso 1 1 calc R
C8 C 0.0881(2) -0.3058(6) 0.4865(3) 0.0607(12) Uani 1 1 d .
H5 H 0.0791 -0.2047 0.4893 0.073 Uiso 1 1 calc R
H6 H 0.1230 -0.3379 0.5468 0.073 Uiso 1 1 calc R
C9 C 0.1456(2) -0.2197(5) 0.4491(3) 0.0563(11) Uani 1 1 d .
C10 C 0.0000 0.1210(7) 0.2500 0.0621(18) Uani 1 2 d S
C11 C 0.0530(3) 0.1999(5) 0.3127(4) 0.0682(14) Uani 1 1 d .
C12 C 0.2209(3) -0.0285(7) 0.5333(4) 0.0805(17) Uani 1 1 d .
H7 H 0.2424 0.0371 0.5810 0.097 Uiso 1 1 calc R
C13 C 0.1793(3) -0.1240(6) 0.5210(4) 0.0719(15) Uani 1 1 d .
H8 H 0.1739 -0.1238 0.5615 0.086 Uiso 1 1 calc R
C14 C -0.0754(3) -0.4034(6) 0.3247(4) 0.0656(13) Uani 1 1 d .
H9 H -0.0801 -0.4078 0.3679 0.079 Uiso 1 1 calc R
H10 H -0.0776 -0.5025 0.3051 0.079 Uiso 1 1 calc R
C15 C 0.0538(2) 0.3528(5) 0.3137(4) 0.0623(13) Uani 1 1 d .
H11 H 0.0901 0.4040 0.3565 0.075 Uiso 1 1 calc R
C16 C 0.1988(2) -0.1272(6) 0.4051(4) 0.0667(13) Uani 1 1 d .
H12 H 0.2061 -0.1299 0.3668 0.080 Uiso 1 1 calc R
C17 C 0.2308(3) -0.0295(6) 0.4761(4) 0.0772(16) Uani 1 1 d .
H13 H 0.2589 0.0350 0.4848 0.093 Uiso 1 1 calc R
C18 C 0.0000 -0.0454(8) 0.2500 0.093(3) Uani 1 2 d S
H14 H -0.0109 -0.0805 0.2826 0.140 Uiso 0.50 1 calc PR
H15 H 0.0401 -0.0805 0.2779 0.140 Uiso 0.50 1 calc PR
H16 H -0.0292 -0.0805 0.1894 0.140 Uiso 0.50 1 calc PR
Ni1 Ni 0.0000 0.0000 0.5000 0.0450(2) Uani 1 2 d S
N1 N 0.0000 0.5877(5) 0.2500 0.0556(14) Uani 1 2 d S
H1A H 0.0008 0.6202 0.2092 0.083 Uiso 0.50 1 calc PR
H1B H 0.0329 0.6202 0.3039 0.083 Uiso 0.50 1 calc PR
H1C H -0.0337 0.6202 0.2370 0.083 Uiso 0.50 1 calc PR
F1 F 0.1015(3) 0.1346(7) 0.3687(5) 0.106(3) Uani 0.50 1 d P
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
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
C4 S2 C1 97.6(2) . .
C1 S3 Ni1 101.66(15) . .
C2 S4 Ni1 101.81(16) . .
C2 S5 C4 97.4(2) . 5_556
C14 O1 C6 115.0(4) . .
C9 O2 C8 116.8(4) . .
C5 O3 C7 116.7(4) . .
C2 C1 S3 122.4(3) 5_556 .
C2 C1 S2 114.8(3) 5_556 .
S3 C1 S2 122.8(3) . .
C1 C2 S4 120.7(4) 5_556 .
C1 C2 S5 117.2(3) 5_556 .
S4 C2 S5 122.1(3) . .
C15 C3 C15 122.0(6) . 2
C15 C3 N1 119.0(3) . .
C15 C3 N1 119.0(3) 2 .
S1 C4 S2 124.5(3) . .
S1 C4 S5 122.5(3) . 5_556
S2 C4 S5 113.0(3) . 5_556
O3 C5 C16 124.3(5) . .
O3 C5 C9 115.8(4) . .
C16 C5 C9 119.9(5) . .
O1 C6 C8 108.0(4) . .
O3 C7 C14 108.8(4) . 2
O2 C8 C6 109.2(4) . .
O2 C9 C13 124.4(5) . .
O2 C9 C5 116.8(4) . .
C13 C9 C5 118.8(5) . .
C11 C10 C11 117.1(6) 2 .
C11 C10 C18 121.4(3) 2 .
C11 C10 C18 121.4(3) . .
F1 C11 C10 119.5(5) . .
F1 C11 C15 118.3(6) . .
C10 C11 C15 122.2(5) . .
C17 C12 C13 120.8(6) . .
C12 C13 C9 120.6(6) . .
O1 C14 C7 107.6(4) . 2
C3 C15 C11 118.3(5) . .
C17 C16 C5 120.4(5) . .
C12 C17 C16 119.5(6) . .
S3 Ni1 S3 179.999(1) . 5_556
S3 Ni1 S4 93.47(4) . 5_556
S3 Ni1 S4 86.53(4) 5_556 5_556
S3 Ni1 S4 86.53(4) . .
S3 Ni1 S4 93.47(4) 5_556 .
S4 Ni1 S4 180.0 5_556 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C4 1.638(5) .
S2 C4 1.731(6) .
S2 C1 1.767(4) .
S3 C1 1.707(5) .
S3 Ni1 2.1623(10) .
S4 C2 1.723(5) .
S4 Ni1 2.1640(12) .
S5 C2 1.735(5) .
S5 C4 1.741(5) 5_556
O1 C14 1.422(6) .
O1 C6 1.430(6) .
O2 C9 1.377(6) .
O2 C8 1.441(6) .
O3 C5 1.381(6) .
O3 C7 1.438(6) .
C1 C2 1.358(6) 5_556
C2 C1 1.358(6) 5_556
C3 C15 1.366(6) .
C3 C15 1.366(6) 2
C3 N1 1.477(7) .
C4 S5 1.741(5) 5_556
C5 C16 1.390(7) .
C5 C9 1.397(7) .
C6 C8 1.492(7) .
C7 C14 1.493(7) 2
C9 C13 1.383(7) .
C10 C11 1.378(6) 2
C10 C11 1.378(6) .
C10 C18 1.516(9) .
C11 F1 1.226(8) .
C11 C15 1.393(7) .
C12 C17 1.366(9) .
C12 C13 1.383(8) .
C14 C7 1.494(7) 2
C16 C17 1.384(8) .
Ni1 S3 2.1624(10) 5_556
Ni1 S4 2.1640(12) 5_556
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
_geom_torsion_site_symmetry_4
Ni1 S3 C1 C2 0.2(4) . 5_556
Ni1 S3 C1 S2 179.5(2) . .
C4 S2 C1 C2 1.2(4) . 5_556
C4 S2 C1 S3 -178.1(3) . .
Ni1 S4 C2 C1 -2.4(4) . 5_556
Ni1 S4 C2 S5 177.2(2) . .
C4 S5 C2 C1 -1.2(4) 5_556 5_556
C4 S5 C2 S4 179.2(3) 5_556 .
C1 S2 C4 S1 178.9(3) . .
C1 S2 C4 S5 -0.4(3) . 5_556
C7 O3 C5 C16 -6.9(7) . .
C7 O3 C5 C9 172.8(4) . .
C14 O1 C6 C8 -171.5(4) . .
C5 O3 C7 C14 -169.3(4) . 2
C9 O2 C8 C6 171.0(4) . .
O1 C6 C8 O2 -66.5(5) . .
C8 O2 C9 C13 5.4(7) . .
C8 O2 C9 C5 -174.9(4) . .
O3 C5 C9 O2 0.4(6) . .
C16 C5 C9 O2 -180.0(4) . .
O3 C5 C9 C13 -180.0(4) . .
C16 C5 C9 C13 -0.3(7) . .
C11 C10 C11 F1 -178.6(8) 2 .
C18 C10 C11 F1 1.4(8) . .
C11 C10 C11 C15 0.0(4) 2 .
C18 C10 C11 C15 180.0(4) . .
C17 C12 C13 C9 -1.8(9) . .
O2 C9 C13 C12 -178.5(5) . .
C5 C9 C13 C12 1.9(8) . .
C6 O1 C14 C7 170.9(4) . 2
C15 C3 C15 C11 0.0(4) 2 .
N1 C3 C15 C11 180.0(4) . .
F1 C11 C15 C3 178.6(7) . .
C10 C11 C15 C3 0.0(8) . .
O3 C5 C16 C17 178.2(5) . .
C9 C5 C16 C17 -1.4(8) . .
C13 C12 C17 C16 0.0(10) . .
C5 C16 C17 C12 1.5(9) . .
C1 S3 Ni1 S3 70(14) . 5_556
C1 S3 Ni1 S4 1.03(16) . 5_556
C1 S3 Ni1 S4 -178.97(16) . .
C2 S4 Ni1 S3 -178.26(17) . .
C2 S4 Ni1 S3 1.74(17) . 5_556
C2 S4 Ni1 S4 -40(8) . 5_556
