#------------------------------------------------------------------------------
#$Date: 2016-03-22 21:12:29 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179015 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/13/4121311.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_4121311
loop_
_publ_author_name
'Wesley Sattler'
'Serge Ruccolo'
'Gerard Parkin'
_publ_section_title
;
 Synthesis, Structure, and Reactivity of a Terminal Organozinc Fluoride
 Compound: Hydrogen Bonding, Halogen Bonding, and Donor-Acceptor
 Interactions
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18714
_journal_page_last               18717
_journal_paper_doi               10.1021/ja408733f
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C16 H12 F N3 S3 Zn'
_chemical_formula_weight         426.84
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.3162(9)
_cell_length_b                   13.2855(8)
_cell_length_c                   9.0351(6)
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      32.34
_cell_measurement_theta_min      2.67
_cell_volume                     1718.46(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0178
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            28202
_diffrn_reflns_theta_full        32.67
_diffrn_reflns_theta_max         32.67
_diffrn_reflns_theta_min         2.67
_exptl_absorpt_coefficient_mu    1.806
_exptl_absorpt_correction_T_max  0.5394
_exptl_absorpt_correction_T_min  0.4207
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.650
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.39
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         3151
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0230
_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)+(0.0321P)²+0.5357P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0602
_refine_ls_wR_factor_ref         0.0623
_reflns_number_gt                2773
_reflns_number_total             3151
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja408733f_si_003.cif
_cod_data_source_block           zfs10
_cod_database_code               4121311
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -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
Zn Zn 0.343810(12) 0.2500 0.525659(19) 0.01583(5) Uani 1 2 d S
S1 S 0.55010(3) 0.2500 0.37081(5) 0.03083(11) Uani 1 2 d S
S2 S 0.53100(2) 0.13849(3) 0.64722(4) 0.03259(8) Uani 1 1 d .
F F 0.20899(7) 0.2500 0.49974(11) 0.02208(19) Uani 1 2 d S
N1 N 0.36838(9) 0.2500 0.29752(15) 0.0202(2) Uani 1 2 d S
N2 N 0.34369(7) 0.12313(8) 0.66021(11) 0.02032(18) Uani 1 1 d .
C C 0.49820(11) 0.2500 0.54940(17) 0.0201(3) Uani 1 2 d S
C11 C 0.45579(11) 0.2500 0.24668(17) 0.0207(3) Uani 1 2 d S
C12 C 0.47649(13) 0.2500 0.09460(19) 0.0264(3) Uani 1 2 d S
H12A H 0.5380 0.2500 0.0614 0.032 Uiso 1 2 calc SR
C13 C 0.40309(15) 0.2500 -0.00381(19) 0.0292(4) Uani 1 2 d S
H13A H 0.4146 0.2500 -0.1051 0.035 Uiso 1 2 calc SR
C14 C 0.31150(15) 0.2500 0.0484(2) 0.0318(4) Uani 1 2 d S
H14A H 0.2614 0.2500 -0.0171 0.038 Uiso 1 2 calc SR
C15 C 0.29676(12) 0.2500 0.19948(19) 0.0268(3) Uani 1 2 d S
H15A H 0.2358 0.2500 0.2350 0.032 Uiso 1 2 calc SR
C21 C 0.42486(8) 0.08410(9) 0.70454(13) 0.0234(2) Uani 1 1 d .
C22 C 0.42898(10) 0.00103(10) 0.79971(16) 0.0338(3) Uani 1 1 d .
H22A H 0.4863 -0.0256 0.8285 0.041 Uiso 1 1 calc R
C23 C 0.34672(11) -0.04063(11) 0.84991(18) 0.0384(3) Uani 1 1 d .
H23A H 0.3478 -0.0966 0.9117 0.046 Uiso 1 1 calc R
C24 C 0.26221(11) 0.00186(10) 0.80717(17) 0.0354(3) Uani 1 1 d .
H24A H 0.2060 -0.0240 0.8421 0.042 Uiso 1 1 calc R
C25 C 0.26306(9) 0.08298(9) 0.71210(14) 0.0262(2) Uani 1 1 d .
H25A H 0.2065 0.1111 0.6826 0.031 Uiso 1 1 calc R
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'
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'
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
F Zn N2 93.99(3) . 7_565
F Zn N2 93.99(3) . .
N2 Zn N2 108.40(5) 7_565 .
F Zn N1 92.77(5) . .
N2 Zn N1 125.22(3) 7_565 .
N2 Zn N1 125.22(3) . .
F Zn C 178.63(5) . .
N2 Zn C 86.81(4) 7_565 .
N2 Zn C 86.81(4) . .
N1 Zn C 85.86(5) . .
C11 S1 C 104.99(7) . .
C21 S2 C 105.00(6) . .
C11 N1 C15 119.02(14) . .
C11 N1 Zn 119.84(11) . .
C15 N1 Zn 121.14(11) . .
C21 N2 C25 119.02(10) . .
C21 N2 Zn 119.35(8) . .
C25 N2 Zn 121.48(8) . .
S1 C S2 109.83(6) . 7_565
S1 C S2 109.83(6) . .
S2 C S2 111.92(9) 7_565 .
S1 C Zn 109.18(8) . .
S2 C Zn 108.01(6) 7_565 .
S2 C Zn 108.01(6) . .
N1 C11 C12 122.32(15) . .
N1 C11 S1 120.13(12) . .
C12 C11 S1 117.55(13) . .
C13 C12 C11 118.07(17) . .
C12 C13 C14 119.99(16) . .
C15 C14 C13 118.56(17) . .
N1 C15 C14 122.04(17) . .
N2 C21 C22 121.83(12) . .
N2 C21 S2 120.26(9) . .
C22 C21 S2 117.89(10) . .
C23 C22 C21 118.86(13) . .
C22 C23 C24 119.30(12) . .
C25 C24 C23 118.89(13) . .
N2 C25 C24 122.07(12) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn F 1.9443(10) .
Zn N2 2.0782(10) 7_565
Zn N2 2.0782(10) .
Zn N1 2.0911(14) .
Zn C 2.2207(16) .
S1 C11 1.7551(17) .
S1 C 1.7764(16) .
S2 C21 1.7604(13) .
S2 C 1.7878(9) .
N1 C11 1.333(2) .
N1 C15 1.355(2) .
N2 C21 1.3340(15) .
N2 C25 1.3553(15) .
C S2 1.7877(9) 7_565
C11 C12 1.406(2) .
C12 C13 1.377(3) .
C13 C14 1.393(3) .
C14 C15 1.381(2) .
C21 C22 1.4003(17) .
C22 C23 1.378(2) .
C23 C24 1.390(2) .
C24 C25 1.3782(18) .
