#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/72/2237254.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2237254
loop_
_publ_author_name
'Zhang, Yuan'
_publ_section_title
;
 Butan-1-aminium tetrachloridoferrate(III)--18-crown-6 (1/1)
;
_journal_coeditor_code           XU5660
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m38
_journal_paper_doi               10.1107/S160053681204994X
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          '(C4 H12 N) [Fe Cl4], C12 H24 O6'
_chemical_formula_moiety         'C4 H12 N +, Cl4 Fe -, C12 H24 O6'
_chemical_formula_sum            'C16 H36 Cl4 Fe N O6'
_chemical_formula_weight         536.11
_chemical_name_common
;
Butan-1-aminium tetrachloridoferrate(III)--18-crown-6 (1/1)
;
_chemical_name_systematic
;
Butan-1-aminium tetrachloridoferrate(III)--1,4,7,10,13,16-
hexaoxacyclooctadecane (1/1)
;
_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                   9.3109(19)
_cell_length_b                   11.431(2)
_cell_length_c                   24.718(5)
_cell_measurement_reflns_used    3160
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.480
_cell_measurement_theta_min      2.3755
_cell_volume                     2630.8(9)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku SCXmini'
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0899
_diffrn_reflns_av_sigmaI/netI    0.0553
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            24682
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    1.007
_exptl_absorpt_correction_T_max  0.820
_exptl_absorpt_correction_T_min  0.665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.737
_refine_diff_density_min         -0.396
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         3160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.1500
_refine_ls_R_factor_gt           0.0788
_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)+(0.0881P)²+3.1745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1965
_refine_ls_wR_factor_ref         0.2340
_reflns_number_gt                1649
_reflns_number_total             3160
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5660.cif
_cod_data_source_block           I
_cod_database_code               2237254
_cod_database_fobs_code          2237254
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Fe Fe1 0.22073(9) 0.2500 0.88238(3) 0.0713(3) Uani d S 1 2
Cl Cl1 0.4469(2) 0.2500 0.86376(15) 0.1792(13) Uani d S 1 2
Cl Cl2 0.0976(2) 0.2500 0.80773(6) 0.0961(6) Uani d S 1 2
Cl Cl3 0.1710(3) 0.40675(17) 0.92687(8) 0.1835(8) Uani d . 1 1
N N1 0.3475(4) 0.7500 0.65867(15) 0.0562(11) Uani d S 1 2
H H1A 0.3430 0.7500 0.6950 0.084 Uiso d SR 1 2
H H1B 0.3034 0.8143 0.6457 0.084 Uiso d R 1 1
C C8 0.5254(9) 0.7500 0.5846(4) 0.133(3) Uani d S 1 2
H H8A 0.4780 0.6824 0.5700 0.159 Uiso d R 1 1
C C9 0.6662(8) 0.7500 0.5629(4) 0.129(3) Uani d S 1 2
H H9A 0.7139 0.6822 0.5771 0.155 Uiso d R 1 1
C C7 0.4966(7) 0.7500 0.6410(3) 0.131(4) Uani d S 1 2
H H7A 0.5430 0.6822 0.6559 0.157 Uiso d R 1 1
C C10 0.6838(10) 0.7500 0.5070(4) 0.175(5) Uani d S 1 2
H H10A 0.7837 0.7500 0.4973 0.262 Uiso d SR 1 2
H H10B 0.6384 0.6814 0.4925 0.262 Uiso d R 1 1
O O4 0.1585(5) 0.7500 0.56513(17) 0.0986(16) Uani d S 1 2
C C6 0.0868(5) 0.8539(6) 0.54992(19) 0.121(2) Uani d . 1 1
H H6A -0.0039 0.8575 0.5683 0.145 Uiso d R 1 1
H H6B 0.0687 0.8537 0.5117 0.145 Uiso d R 1 1
O O1 0.3486(5) 0.7500 0.77856(16) 0.0929(15) Uani d S 1 2
C C1 0.4203(6) 0.8546(6) 0.79449(19) 0.127(2) Uani d . 1 1
H H1C 0.5134 0.8572 0.7778 0.152 Uiso d R 1 1
H H1D 0.4331 0.8557 0.8330 0.152 Uiso d R 1 1
O O2 0.3379(3) 0.9612(3) 0.71993(14) 0.0964(10) Uani d . 1 1
O O3 0.1868(3) 0.9589(3) 0.62119(14) 0.0938(10) Uani d . 1 1
C C4 0.2686(6) 1.0561(5) 0.6389(3) 0.121(2) Uani d . 1 1
H H4A 0.2304 1.1272 0.6240 0.145 Uiso d R 1 1
H H4B 0.3662 1.0480 0.6270 0.145 Uiso d R 1 1
C C5 0.1737(6) 0.9561(6) 0.5645(2) 0.127(2) Uani d . 1 1
H H5A 0.1275 1.0264 0.5524 0.153 Uiso d R 1 1
H H5B 0.2662 0.9511 0.5475 0.153 Uiso d R 1 1
C C3 0.2649(6) 1.0613(4) 0.6980(3) 0.121(2) Uani d . 1 1
H H3A 0.3112 1.1312 0.7106 0.145 Uiso d R 1 1
H H3B 0.1668 1.0626 0.7100 0.145 Uiso d R 1 1
C C2 0.3375(6) 0.9578(6) 0.7762(2) 0.129(2) Uani d . 1 1
H H2A 0.3783 1.0284 0.7906 0.154 Uiso d R 1 1
H H2B 0.2407 0.9508 0.7891 0.154 Uiso d R 1 1
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 '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'
H H 0.0000 0.0000 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
Cl3 Fe1 Cl3 . 8_565 112.68(13)
Cl3 Fe1 Cl1 . . 108.61(8)
Cl3 Fe1 Cl1 8_565 . 108.61(8)
Cl3 Fe1 Cl2 . . 108.69(6)
Cl3 Fe1 Cl2 8_565 . 108.69(6)
Cl1 Fe1 Cl2 . . 109.52(12)
C7 N1 H1A . . 110.2
C7 N1 H1B . . 109.1
H1A N1 H1B . . 109.5
C9 C8 C7 . . 123.1(8)
C9 C8 H8A . . 106.4
C7 C8 H8A . . 106.5
C10 C9 C8 . . 119.0(9)
C10 C9 H9A . . 107.9
C8 C9 H9A . . 106.9
C8 C7 N1 . . 118.4(6)
C8 C7 H7A . . 106.9
N1 C7 H7A . . 108.3
C9 C10 H10A . . 111.2
C9 C10 H10B . . 108.6
H10A C10 H10B . . 109.5
C6 O4 C6 8_575 . 114.4(6)
O4 C6 C5 . . 110.1(4)
O4 C6 H6A . . 109.0
C5 C6 H6A . . 109.6
O4 C6 H6B . . 110.1
C5 C6 H6B . . 109.9
H6A C6 H6B . . 108.2
C1 O1 C1 . 8_575 114.1(6)
O1 C1 C2 . . 109.9(4)
O1 C1 H1C . . 109.3
C2 C1 H1C . . 108.3
O1 C1 H1D . . 110.1
C2 C1 H1D . . 110.9
H1C C1 H1D . . 108.3
C2 O2 C3 . . 113.4(5)
C5 O3 C4 . . 111.9(4)
O3 C4 C3 . . 109.1(4)
O3 C4 H4A . . 110.3
C3 C4 H4A . . 109.9
O3 C4 H4B . . 109.8
C3 C4 H4B . . 109.4
H4A C4 H4B . . 108.3
O3 C5 C6 . . 108.2(4)
O3 C5 H5A . . 109.2
C6 C5 H5A . . 110.0
O3 C5 H5B . . 111.1
C6 C5 H5B . . 109.9
H5A C5 H5B . . 108.4
O2 C3 C4 . . 109.5(4)
O2 C3 H3A . . 109.2
C4 C3 H3A . . 110.3
O2 C3 H3B . . 110.2
C4 C3 H3B . . 109.3
H3A C3 H3B . . 108.3
O2 C2 C1 . . 109.0(5)
O2 C2 H2A . . 110.3
C1 C2 H2A . . 110.5
O2 C2 H2B . . 109.7
C1 C2 H2B . . 108.7
H2A C2 H2B . . 108.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Fe1 Cl3 . 2.1528(18)
Fe1 Cl3 8_565 2.1528(18)
Fe1 Cl1 . 2.155(2)
Fe1 Cl2 . 2.1723(18)
N1 C7 . 1.456(8)
N1 H1A . 0.9000
N1 H1B . 0.9001
C8 C9 . 1.416(10)
C8 C7 . 1.419(10)
C8 H8A . 0.9600
C9 C10 . 1.392(12)
C9 H9A . 0.9600
C7 H7A . 0.9600
C10 H10A . 0.9601
C10 H10B . 0.9601
O4 C6 8_575 1.413(6)
O4 C6 . 1.413(6)
C6 C5 . 1.466(9)
C6 H6A . 0.9600
C6 H6B . 0.9599
O1 C1 . 1.425(6)
O1 C1 8_575 1.425(6)
C1 C2 . 1.480(9)
C1 H1C . 0.9600
C1 H1D . 0.9601
O2 C2 . 1.391(6)
O2 C3 . 1.437(6)
O3 C5 . 1.406(6)
O3 C4 . 1.416(7)
C4 C3 . 1.463(9)
C4 H4A . 0.9601
C4 H4B . 0.9600
C5 H5A . 0.9600
C5 H5B . 0.9600
C3 H3A . 0.9599
C3 H3B . 0.9600
C2 H2A . 0.9601
C2 H2B . 0.9601
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O1 0.90 2.07 2.963(5) 176
N1 H1B O3 0.90 2.07 2.966(4) 175
