#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:04:30 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180167 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/63/7106380.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_7106380
loop_
_publ_author_name
'Song Yi'
'Burjor Captain'
'Angel E. Kaifer'
_publ_section_title
;
 The importance of methylation in the binding of (ferrocenylmethyl)-
 tempammonium guests by cucurbit[n]uril (n = 7, 8) hosts
;
_journal_name_full               Chem.Commun.
_journal_page_first              5500
_journal_paper_doi               10.1039/c1cc11212k
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C21 H31 Fe N2 O'
_chemical_formula_weight         383.33
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 99.3020(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6659(5)
_cell_length_b                   5.9289(2)
_cell_length_c                   28.2755(12)
_cell_measurement_reflns_used    9223
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.68
_cell_measurement_theta_min      2.47
_cell_volume                     1929.98(13)
_computing_cell_refinement       'SAINT+ V7.46A (Bruker, 2007)'
_computing_data_collection       'APEX2 v2.2-0 (Bruker, 2007)'
_computing_data_reduction        'SAINT+ V7.46A (Bruker, 2007)'
_computing_molecular_graphics    'XSHELL v4.02 (Bruker, 2000)'
_computing_publication_material  'XCIF v6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX2 CCD diffractometer'
_diffrn_measurement_method       'omega 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  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            20035
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  0.9250
_exptl_absorpt_correction_T_min  0.7023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS 2007/4 Bruker)'
_exptl_crystal_colour            Orange
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Bar
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.480
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         5096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0365
_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)+(0.0485P)²+0.5466P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                4538
_reflns_number_total             5096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc11212k.txt
_cod_data_source_block           collect_0m2
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7106380
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Fe1 Fe 0.682527(17) 1.20513(4) 0.103629(7) 0.03109(8) Uani 1 1 d . . .
O1 O 0.04827(13) 0.2329(3) 0.11748(5) 0.0577(4) Uani 1 1 d . . .
N1 N 0.42511(10) 0.8054(2) 0.16729(4) 0.0304(2) Uani 1 1 d . . .
N2 N 0.12999(11) 0.3769(2) 0.12832(4) 0.0348(3) Uani 1 1 d . . .
C1 C 0.58209(13) 1.0505(3) 0.14693(5) 0.0345(3) Uani 1 1 d . . .
C2 C 0.68673(14) 0.9288(3) 0.14697(6) 0.0402(3) Uani 1 1 d . . .
H2 H 0.6923 0.7790 0.1378 0.048 Uiso 1 1 calc R . .
C3 C 0.78175(14) 1.0746(3) 0.16334(6) 0.0435(4) Uani 1 1 d . . .
H3 H 0.8601 1.0373 0.1665 0.052 Uiso 1 1 calc R . .
C4 C 0.73615(15) 1.2851(3) 0.17384(6) 0.0414(4) Uani 1 1 d . . .
H4 H 0.7793 1.4111 0.1854 0.050 Uiso 1 1 calc R . .
C5 C 0.61269(15) 1.2725(3) 0.16377(6) 0.0365(3) Uani 1 1 d . . .
H5 H 0.5612 1.3885 0.1675 0.044 Uiso 1 1 calc R . .
C6 C 0.58827(19) 1.2322(4) 0.03640(7) 0.0522(5) Uani 1 1 d . . .
H6 H 0.5114 1.1879 0.0272 0.063 Uiso 1 1 calc R . .
C7 C 0.6871(2) 1.0969(4) 0.03559(6) 0.0550(5) Uani 1 1 d . . .
H7 H 0.6870 0.9475 0.0256 0.066 Uiso 1 1 calc R . .
C8 C 0.78672(18) 1.2275(4) 0.05265(7) 0.0540(5) Uani 1 1 d . . .
H8 H 0.8635 1.1793 0.0560 0.065 Uiso 1 1 calc R . .
C9 C 0.74871(18) 1.4431(4) 0.06363(6) 0.0518(5) Uani 1 1 d . . .
H9 H 0.7962 1.5629 0.0755 0.062 Uiso 1 1 calc R . .
C10 C 0.62686(18) 1.4472(3) 0.05365(6) 0.0509(4) Uani 1 1 d . . .
H10 H 0.5798 1.5700 0.0577 0.061 Uiso 1 1 calc R . .
C11 C 0.46116(13) 0.9607(3) 0.13187(6) 0.0404(4) Uani 1 1 d . . .
H11A H 0.4072 1.0862 0.1270 0.048 Uiso 1 1 calc R . .
H11B H 0.4574 0.8825 0.1015 0.048 Uiso 1 1 calc R . .
C12 C 0.44111(15) 0.9148(3) 0.21416(6) 0.0420(4) Uani 1 1 d . . .
H12A H 0.5214 0.9543 0.2235 0.063 Uiso 1 1 calc R . .
H12B H 0.4181 0.8134 0.2374 0.063 Uiso 1 1 calc R . .
H12C H 0.3944 1.0488 0.2124 0.063 Uiso 1 1 calc R . .
C13 C 0.30316(12) 0.7299(2) 0.15193(5) 0.0284(3) Uani 1 1 d . . .
H13 H 0.2516 0.8612 0.1471 0.034 Uiso 1 1 calc R . .
C14 C 0.26619(13) 0.5755(3) 0.18983(5) 0.0342(3) Uani 1 1 d . . .
H14A H 0.2704 0.6600 0.2194 0.041 Uiso 1 1 calc R . .
H14B H 0.3214 0.4525 0.1957 0.041 Uiso 1 1 calc R . .
C15 C 0.14418(13) 0.4758(3) 0.17714(5) 0.0353(3) Uani 1 1 d . . .
C16 C 0.17420(13) 0.4896(3) 0.08754(5) 0.0335(3) Uani 1 1 d . . .
C17 C 0.29364(12) 0.5949(3) 0.10539(5) 0.0322(3) Uani 1 1 d . . .
H17A H 0.3510 0.4750 0.1100 0.039 Uiso 1 1 calc R . .
H17B H 0.3133 0.6935 0.0805 0.039 Uiso 1 1 calc R . .
C18 C 0.04938(17) 0.6530(4) 0.17963(8) 0.0557(5) Uani 1 1 d . . .
H18A H 0.0642 0.7835 0.1614 0.083 Uiso 1 1 calc R . .
H18B H 0.0497 0.6955 0.2124 0.083 Uiso 1 1 calc R . .
H18C H -0.0250 0.5909 0.1666 0.083 Uiso 1 1 calc R . .
C19 C 0.13089(19) 0.2850(3) 0.21231(7) 0.0511(5) Uani 1 1 d . . .
H19A H 0.0528 0.2283 0.2061 0.077 Uiso 1 1 calc R . .
H19B H 0.1474 0.3414 0.2445 0.077 Uiso 1 1 calc R . .
H19C H 0.1841 0.1657 0.2083 0.077 Uiso 1 1 calc R . .
C20 C 0.08668(16) 0.6659(3) 0.06429(7) 0.0478(4) Uani 1 1 d . . .
H20A H 0.0110 0.5986 0.0571 0.072 Uiso 1 1 calc R . .
H20B H 0.1098 0.7195 0.0352 0.072 Uiso 1 1 calc R . .
H20C H 0.0844 0.7899 0.0860 0.072 Uiso 1 1 calc R . .
C21 C 0.18804(18) 0.3080(3) 0.05051(6) 0.0469(4) Uani 1 1 d . . .
H21A H 0.2347 0.1870 0.0658 0.070 Uiso 1 1 calc R . .
H21B H 0.2252 0.3718 0.0257 0.070 Uiso 1 1 calc R . .
H21C H 0.1129 0.2512 0.0368 0.070 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'
O O 0.0106 0.0060 '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'
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
_geom_angle_publ_flag
C8 Fe1 C9 40.34(9) . . ?
C8 Fe1 C7 40.66(9) . . ?
C9 Fe1 C7 67.88(8) . . ?
C8 Fe1 C4 123.39(8) . . ?
C9 Fe1 C4 107.18(7) . . ?
C7 Fe1 C4 160.44(9) . . ?
C8 Fe1 C3 106.69(8) . . ?
C9 Fe1 C3 120.49(7) . . ?
C7 Fe1 C3 124.37(8) . . ?
C4 Fe1 C3 40.38(8) . . ?
C8 Fe1 C5 160.47(8) . . ?
C9 Fe1 C5 124.43(8) . . ?
C7 Fe1 C5 157.50(8) . . ?
C4 Fe1 C5 40.87(7) . . ?
C3 Fe1 C5 68.53(7) . . ?
C8 Fe1 C2 121.23(8) . . ?
C9 Fe1 C2 156.16(8) . . ?
C7 Fe1 C2 108.21(8) . . ?
C4 Fe1 C2 68.19(7) . . ?
C3 Fe1 C2 40.81(7) . . ?
C5 Fe1 C2 68.35(7) . . ?
C8 Fe1 C6 68.22(9) . . ?
C9 Fe1 C6 67.92(8) . . ?
C7 Fe1 C6 40.37(9) . . ?
C4 Fe1 C6 157.25(9) . . ?
C3 Fe1 C6 161.53(8) . . ?
C5 Fe1 C6 122.20(8) . . ?
C2 Fe1 C6 125.35(8) . . ?
C8 Fe1 C1 156.91(8) . . ?
C9 Fe1 C1 161.62(8) . . ?
C7 Fe1 C1 121.99(8) . . ?
C4 Fe1 C1 68.67(6) . . ?
C3 Fe1 C1 68.74(6) . . ?
C5 Fe1 C1 40.85(6) . . ?
C2 Fe1 C1 40.62(6) . . ?
C6 Fe1 C1 108.56(7) . . ?
C8 Fe1 C10 67.91(9) . . ?
C9 Fe1 C10 40.24(8) . . ?
C7 Fe1 C10 67.80(9) . . ?
C4 Fe1 C10 121.52(8) . . ?
C3 Fe1 C10 155.92(8) . . ?
C5 Fe1 C10 108.27(8) . . ?
C2 Fe1 C10 162.19(8) . . ?
C6 Fe1 C10 40.43(8) . . ?
C1 Fe1 C10 125.46(7) . . ?
C12 N1 C11 109.34(13) . . ?
C12 N1 C13 112.00(12) . . ?
C11 N1 C13 110.79(11) . . ?
O1 N2 C15 116.94(12) . . ?
O1 N2 C16 116.76(12) . . ?
C15 N2 C16 122.70(12) . . ?
C2 C1 C5 107.51(14) . . ?
C2 C1 C11 126.01(15) . . ?
C5 C1 C11 126.47(15) . . ?
C2 C1 Fe1 69.64(9) . . ?
C5 C1 Fe1 69.46(9) . . ?
C11 C1 Fe1 126.28(10) . . ?
C1 C2 C3 108.43(15) . . ?
C1 C2 Fe1 69.74(9) . . ?
C3 C2 Fe1 69.49(9) . . ?
C4 C3 C2 107.84(15) . . ?
C4 C3 Fe1 69.79(9) . . ?
C2 C3 Fe1 69.70(9) . . ?
C3 C4 C5 108.41(15) . . ?
C3 C4 Fe1 69.82(10) . . ?
C5 C4 Fe1 69.63(9) . . ?
C4 C5 C1 107.80(15) . . ?
C4 C5 Fe1 69.50(9) . . ?
C1 C5 Fe1 69.68(9) . . ?
C7 C6 C10 107.67(18) . . ?
C7 C6 Fe1 69.60(11) . . ?
C10 C6 Fe1 69.88(10) . . ?
C6 C7 C8 108.21(19) . . ?
C6 C7 Fe1 70.03(11) . . ?
C8 C7 Fe1 69.58(11) . . ?
C9 C8 C7 107.59(18) . . ?
C9 C8 Fe1 69.91(10) . . ?
C7 C8 Fe1 69.76(11) . . ?
C8 C9 C10 108.49(18) . . ?
C8 C9 Fe1 69.75(11) . . ?
C10 C9 Fe1 70.20(10) . . ?
C9 C10 C6 108.03(19) . . ?
C9 C10 Fe1 69.56(10) . . ?
C6 C10 Fe1 69.69(11) . . ?
N1 C11 C1 112.79(12) . . ?
N1 C13 C14 109.98(11) . . ?
N1 C13 C17 109.98(11) . . ?
C14 C13 C17 107.56(12) . . ?
C13 C14 C15 115.19(12) . . ?
N2 C15 C14 109.30(11) . . ?
N2 C15 C19 107.74(13) . . ?
C14 C15 C19 108.75(14) . . ?
N2 C15 C18 109.89(14) . . ?
C14 C15 C18 112.00(14) . . ?
C19 C15 C18 109.06(15) . . ?
N2 C16 C21 107.53(13) . . ?
N2 C16 C20 110.29(13) . . ?
C21 C16 C20 108.85(14) . . ?
N2 C16 C17 109.64(11) . . ?
C21 C16 C17 108.70(13) . . ?
C20 C16 C17 111.72(13) . . ?
C13 C17 C16 115.55(12) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C8 2.0346(18) . ?
Fe1 C9 2.0367(17) . ?
Fe1 C7 2.0369(18) . ?
Fe1 C4 2.0388(16) . ?
Fe1 C3 2.0391(16) . ?
Fe1 C5 2.0405(16) . ?
Fe1 C2 2.0420(16) . ?
Fe1 C6 2.0427(18) . ?
Fe1 C1 2.0434(14) . ?
Fe1 C10 2.0451(18) . ?
O1 N2 1.2796(17) . ?
N1 C12 1.460(2) . ?
N1 C11 1.4708(19) . ?
N1 C13 1.4877(17) . ?
N2 C15 1.4843(19) . ?
N2 C16 1.4946(19) . ?
C1 C2 1.418(2) . ?
C1 C5 1.425(2) . ?
C1 C11 1.504(2) . ?
C2 C3 1.423(2) . ?
C3 C4 1.407(3) . ?
C4 C5 1.424(2) . ?
C6 C7 1.408(3) . ?
C6 C10 1.412(3) . ?
C7 C8 1.415(3) . ?
C8 C9 1.404(3) . ?
C9 C10 1.404(3) . ?
C13 C14 1.5234(19) . ?
C13 C17 1.529(2) . ?
C14 C15 1.530(2) . ?
C15 C19 1.530(2) . ?
C15 C18 1.535(2) . ?
C16 C21 1.529(2) . ?
C16 C20 1.533(2) . ?
C16 C17 1.5357(19) . ?
