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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/4/50/98/4509893.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_4509893
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                 131.4924(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   28.969(2)
_cell_length_b                   9.0811(6)
_cell_length_c                   20.0477(13)
_cell_measurement_temperature    173(2)
_cell_volume                     3950.4(5)
_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      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0846
_diffrn_reflns_av_sigmaI/netI    0.0729
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18514
_diffrn_reflns_theta_full        27.44
_diffrn_reflns_theta_max         27.44
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    1.069
_exptl_absorpt_correction_T_max  0.9006
_exptl_absorpt_correction_T_min  0.6745
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1928
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.963
_refine_diff_density_min         -1.063
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       0.0018(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4500
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0650
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1398P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1732
_refine_ls_wR_factor_ref         0.2388
_reflns_number_gt                2767
_reflns_number_total             4500
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg4013262_si_004.cif
_cod_data_source_block           2f4me
_cod_original_cell_volume        3950.5(5)
_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               4509893
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
O1 O 1.0206(2) -0.3463(4) 0.6385(3) 0.0486(10) Uani 1 1 d .
O2 O 0.8989(2) -0.3180(4) 0.5714(3) 0.0514(10) Uani 1 1 d .
O3 O 0.8781(2) -0.3265(4) 0.6799(3) 0.0514(10) Uani 1 1 d .
S1 S 0.68779(8) -0.13158(17) 0.11084(11) 0.0575(5) Uani 1 1 d .
S2 S 0.78203(7) 0.04144(15) 0.27616(10) 0.0446(4) Uani 1 1 d .
S3 S 0.91459(7) 0.10540(14) 0.44582(10) 0.0421(4) Uani 1 1 d .
S4 S 1.04390(7) 0.15105(14) 0.61056(10) 0.0430(4) Uani 1 1 d .
S5 S 1.17867(7) 0.19933(15) 0.77179(10) 0.0485(4) Uani 1 1 d .
C1 C 1.0000 0.4021(7) 0.7500 0.0384(16) Uani 1 2 d S
C2 C 0.9466(3) 0.3263(6) 0.6866(4) 0.0458(13) Uani 1 1 d .
C3 C 0.9467(3) 0.1731(6) 0.6867(4) 0.0487(14) Uani 1 1 d .
H13 H 0.9095 0.1214 0.6426 0.058 Uiso 1 1 calc R
C4 C 1.0000 0.0954(7) 0.7500 0.0461(19) Uani 1 2 d S
C5 C 1.0000 -0.0698(8) 0.7500 0.073(3) Uani 1 2 d S
H14 H 1.0359 -0.1058 0.7597 0.110 Uiso 0.50 1 calc PR
H15 H 0.9623 -0.1058 0.6925 0.110 Uiso 0.50 1 calc PR
H16 H 1.0018 -0.1058 0.7978 0.110 Uiso 0.50 1 calc PR
C6 C 1.0781(3) -0.4138(6) 0.6771(4) 0.0563(17) Uani 1 1 d .
H1 H 1.0832 -0.4195 0.6329 0.068 Uiso 1 1 calc R
H2 H 1.0801 -0.5147 0.6975 0.068 Uiso 1 1 calc R
C7 C 0.9679(3) -0.4036(6) 0.5534(4) 0.0512(16) Uani 1 1 d .
H3 H 0.9589 -0.5050 0.5602 0.061 Uiso 1 1 calc R
H4 H 0.9761 -0.4067 0.5127 0.061 Uiso 1 1 calc R
C8 C 0.9144(3) -0.3061(6) 0.5161(4) 0.0497(15) Uani 1 1 d .
H5 H 0.9250 -0.2029 0.5152 0.060 Uiso 1 1 calc R
H6 H 0.8788 -0.3359 0.4543 0.060 Uiso 1 1 calc R
C9 C 0.8547(3) -0.2210(6) 0.5526(4) 0.0484(14) Uani 1 1 d .
C10 C 0.8241(3) -0.1208(7) 0.4839(4) 0.0556(16) Uani 1 1 d .
H7 H 0.8317 -0.1174 0.4445 0.067 Uiso 1 1 calc R
C11 C 0.7818(4) -0.0241(7) 0.4723(5) 0.0650(18) Uani 1 1 d .
H8 H 0.7607 0.0452 0.4249 0.078 Uiso 1 1 calc R
C12 C 0.7703(4) -0.0282(7) 0.5284(5) 0.0606(17) Uani 1 1 d .
H9 H 0.7414 0.0377 0.5200 0.073 Uiso 1 1 calc R
C13 C 0.8017(3) -0.1305(6) 0.5984(4) 0.0538(16) Uani 1 1 d .
H10 H 0.7936 -0.1346 0.6372 0.065 Uiso 1 1 calc R
C14 C 0.8438(3) -0.2244(6) 0.6110(4) 0.0471(14) Uani 1 1 d .
C15 C 0.8732(3) -0.3205(7) 0.7467(4) 0.0554(16) Uani 1 1 d .
H11 H 0.8321 -0.3564 0.7215 0.066 Uiso 1 1 calc R
H12 H 0.8779 -0.2176 0.7667 0.066 Uiso 1 1 calc R
C16 C 0.7598(3) -0.0980(6) 0.2006(4) 0.0460(13) Uani 1 1 d .
C17 C 0.8620(3) 0.0078(5) 0.3491(4) 0.0386(11) Uani 1 1 d .
C18 C 1.1203(3) 0.1045(6) 0.6739(4) 0.0433(13) Uani 1 1 d .
Ni1 Ni 1.0000 0.0000 0.5000 0.0373(3) Uani 1 2 d S
N1 N 1.0000 0.5640(6) 0.7500 0.0517(19) Uani 1 2 d S
H1A H 0.9613 0.5974 0.7041 0.078 Uiso 0.50 1 calc PR
H1B H 1.0264 0.5974 0.7435 0.078 Uiso 0.50 1 calc PR
H1C H 1.0123 0.5974 0.8024 0.078 Uiso 0.50 1 calc PR
F1 F 0.8916(4) 0.3850(7) 0.6245(5) 0.066(2) 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
C6 O1 C7 115.4(4) . .
C9 O2 C8 116.3(4) . .
C14 O3 C15 116.9(5) . .
C16 S2 C17 97.0(3) . .
C17 S3 Ni1 101.69(18) . .
C18 S4 Ni1 101.32(19) . .
C16 S5 C18 97.0(3) 5_756 .
C2 C1 C2 119.7(7) 2_756 .
C2 C1 N1 120.1(3) 2_756 .
C2 C1 N1 120.1(3) . .
F1 C2 C1 126.0(6) . .
F1 C2 C3 113.9(6) . .
C1 C2 C3 120.0(6) . .
C4 C3 C2 121.0(6) . .
C3 C4 C3 118.3(7) . 2_756
C3 C4 C5 120.8(3) . .
C3 C4 C5 120.8(3) 2_756 .
O1 C6 C15 106.6(5) . 2_756
O1 C7 C8 108.4(4) . .
O2 C8 C7 108.6(4) . .
C10 C9 O2 124.1(5) . .
C10 C9 C14 119.9(6) . .
O2 C9 C14 116.0(5) . .
C9 C10 C11 119.7(6) . .
C12 C11 C10 120.6(6) . .
C11 C12 C13 119.5(7) . .
C14 C13 C12 120.2(6) . .
C13 C14 O3 124.2(5) . .
C13 C14 C9 120.0(5) . .
O3 C14 C9 115.8(5) . .
O3 C15 C6 109.0(5) . 2_756
S1 C16 S2 123.9(4) . .
S1 C16 S5 122.6(3) . 5_756
S2 C16 S5 113.5(3) . 5_756
C18 C17 S3 121.4(5) 5_756 .
C18 C17 S2 115.8(4) 5_756 .
S3 C17 S2 122.8(3) . .
C17 C18 S4 121.7(5) 5_756 .
C17 C18 S5 116.8(5) 5_756 .
S4 C18 S5 121.5(3) . .
S3 Ni1 S3 180.0 5_756 .
S3 Ni1 S4 93.78(5) 5_756 .
S3 Ni1 S4 86.22(5) . .
S3 Ni1 S4 86.22(5) 5_756 5_756
S3 Ni1 S4 93.78(5) . 5_756
S4 Ni1 S4 179.996(1) . 5_756
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C6 1.429(8) .
O1 C7 1.436(7) .
O2 C9 1.385(7) .
O2 C8 1.450(6) .
O3 C14 1.391(7) .
O3 C15 1.439(7) .
S1 C16 1.646(6) .
S2 C16 1.738(6) .
S2 C17 1.764(6) .
S3 C17 1.718(6) .
S3 Ni1 2.1580(14) .
S4 C18 1.721(6) .
S4 Ni1 2.1626(13) .
S5 C16 1.739(6) 5_756
S5 C18 1.748(6) .
C1 C2 1.370(7) 2_756
C1 C2 1.370(7) .
C1 N1 1.470(8) .
C2 F1 1.320(9) .
C2 C3 1.391(7) .
C3 C4 1.377(7) .
C4 C3 1.377(7) 2_756
C4 C5 1.500(10) .
C6 C15 1.479(9) 2_756
C7 C8 1.486(9) .
C9 C10 1.376(8) .
C9 C14 1.401(8) .
C10 C11 1.395(10) .
C11 C12 1.369(9) .
C12 C13 1.403(9) .
C13 C14 1.368(9) .
C15 C6 1.479(9) 2_756
C16 S5 1.739(6) 5_756
C17 C18 1.353(8) 5_756
C18 C17 1.353(8) 5_756
Ni1 S3 2.1579(14) 5_756
Ni1 S4 2.1626(14) 5_756
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
C2 C1 C2 F1 176.7(8) 2_756 .
N1 C1 C2 F1 -3.3(8) . .
C2 C1 C2 C3 0.0(4) 2_756 .
N1 C1 C2 C3 180.0(4) . .
F1 C2 C3 C4 -177.0(6) . .
C1 C2 C3 C4 0.0(8) . .
C2 C3 C4 C3 0.0(4) . 2_756
C2 C3 C4 C5 180.0(4) . .
C7 O1 C6 C15 168.5(5) . 2_756
C6 O1 C7 C8 -170.5(4) . .
C9 O2 C8 C7 172.5(5) . .
O1 C7 C8 O2 -66.6(6) . .
C8 O2 C9 C10 2.6(8) . .
C8 O2 C9 C14 -174.7(5) . .
O2 C9 C10 C11 -177.8(6) . .
C14 C9 C10 C11 -0.7(9) . .
C9 C10 C11 C12 -0.2(10) . .
C10 C11 C12 C13 0.2(11) . .
C11 C12 C13 C14 0.7(10) . .
C12 C13 C14 O3 178.3(6) . .
C12 C13 C14 C9 -1.5(9) . .
C15 O3 C14 C13 -6.9(8) . .
C15 O3 C14 C9 172.9(5) . .
C10 C9 C14 C13 1.5(9) . .
O2 C9 C14 C13 178.9(5) . .
C10 C9 C14 O3 -178.3(5) . .
O2 C9 C14 O3 -0.9(8) . .
C14 O3 C15 C6 -168.2(5) . 2_756
C17 S2 C16 S1 -179.7(4) . .
C17 S2 C16 S5 -0.3(3) . 5_756
Ni1 S3 C17 C18 0.7(5) . 5_756
Ni1 S3 C17 S2 178.2(3) . .
C16 S2 C17 C18 0.2(5) . 5_756
C16 S2 C17 S3 -177.4(3) . .
Ni1 S4 C18 C17 -3.3(5) . 5_756
Ni1 S4 C18 S5 177.2(3) . .
C16 S5 C18 C17 0.1(5) 5_756 5_756
C16 S5 C18 S4 179.7(3) 5_756 .
C17 S3 Ni1 S3 -80(5) . 5_756
C17 S3 Ni1 S4 -178.92(18) . .
C17 S3 Ni1 S4 1.08(18) . 5_756
C18 S4 Ni1 S3 2.15(19) . 5_756
C18 S4 Ni1 S3 -177.85(19) . .
C18 S4 Ni1 S4 -54(5) . 5_756
