#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/60/1506087.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_1506087
loop_
_publ_author_name
'Williams, Iwan'
'Kariuki, Benson M.'
'Reeves, Keith'
'Cox, Liam R.'
_publ_section_title
;
 Stereoselective synthesis of 2-dienyl-substituted pyrrolidines using an
 eta4-dienetricarbonyliron complex as the stereodirecting element:
 Elaboration to the pyrrolizidine skeleton.
;
_journal_issue                   20
_journal_name_full               'Organic letters'
_journal_page_first              4389
_journal_page_last               4392
_journal_paper_doi               10.1021/ol061132l
_journal_volume                  8
_journal_year                    2006
_chemical_formula_moiety         'C16 H20 Br Fe N O3'
_chemical_formula_sum            'C16 H20 Br Fe N O3'
_chemical_formula_weight         410.09
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                69.1110(10)
_cell_angle_beta                 86.3010(10)
_cell_angle_gamma                87.8730(10)
_cell_formula_units_Z            2
_cell_length_a                   7.3427(2)
_cell_length_b                   10.3573(2)
_cell_length_c                   12.6116(3)
_cell_measurement_reflns_used    2337
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      70.61
_cell_measurement_theta_min      3.76
_cell_volume                     894.11(4)
_computing_cell_refinement       SAINTPLUS
_computing_data_collection       SMART
_computing_data_reduction        SAINTPLUS
_computing_structure_refinement  SHELXTL
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.843
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_device_type  'Bruker Smart 6000 CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5410
_diffrn_reflns_theta_full        70.61
_diffrn_reflns_theta_max         70.61
_diffrn_reflns_theta_min         3.76
_exptl_absorpt_coefficient_mu    9.470
_exptl_absorpt_correction_T_max  0.5179
_exptl_absorpt_correction_T_min  0.1063
_exptl_absorpt_correction_type   semiempirical
_exptl_absorpt_process_details   Sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.775
_refine_diff_density_min         -0.728
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2897
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.118
_refine_ls_R_factor_all          0.0716
_refine_ls_R_factor_gt           0.0608
_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)+(0.1096P)²+0.3883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1790
_refine_ls_wR_factor_ref         0.1929
_reflns_number_gt                2337
_reflns_number_total             2897
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol061132lsi20060509_121051.cif
_cod_data_source_block           iwii
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1506087
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
C1 C 0.1295(11) 0.7416(9) 0.3490(6) 0.084(2) Uani 1 1 d .
H1A H 0.0487 0.6846 0.3286 0.127 Uiso 1 1 calc R
H1B H 0.2330 0.7647 0.2955 0.127 Uiso 1 1 calc R
H1C H 0.0662 0.8247 0.3481 0.127 Uiso 1 1 calc R
C2 C 0.1937(7) 0.6638(6) 0.4672(5) 0.0569(13) Uani 1 1 d .
H2 H 0.3039 0.6149 0.4757 0.068 Uiso 1 1 calc R
C3 C 0.0877(7) 0.6648(6) 0.5646(5) 0.0573(13) Uani 1 1 d .
H3 H -0.0307 0.7008 0.5587 0.069 Uiso 1 1 calc R
C4 C 0.1667(7) 0.6098(6) 0.6707(5) 0.0535(12) Uani 1 1 d .
H4 H 0.1005 0.6067 0.7369 0.064 Uiso 1 1 calc R
C5 C 0.3497(6) 0.5591(5) 0.6745(4) 0.0473(11) Uani 1 1 d .
H5 H 0.4107 0.5540 0.6091 0.057 Uiso 1 1 calc R
C6 C 0.4449(6) 0.5134(6) 0.7850(4) 0.0488(11) Uani 1 1 d .
H6 H 0.3897 0.5617 0.8335 0.059 Uiso 1 1 calc R
C7 C 0.6525(8) 0.5380(8) 0.7696(5) 0.0666(16) Uani 1 1 d .
H7A H 0.7033 0.5241 0.7015 0.080 Uiso 1 1 calc R
H7B H 0.6796 0.6308 0.7651 0.080 Uiso 1 1 calc R
C8 C 0.7277(8) 0.4293(9) 0.8769(6) 0.0748(18) Uani 1 1 d .
H8A H 0.8273 0.3767 0.8568 0.090 Uiso 1 1 calc R
H8B H 0.7717 0.4733 0.9264 0.090 Uiso 1 1 calc R
C9 C 0.5682(8) 0.3361(7) 0.9350(5) 0.0643(14) Uani 1 1 d .
H9A H 0.6067 0.2397 0.9617 0.077 Uiso 1 1 calc R
H9B H 0.5160 0.3585 0.9991 0.077 Uiso 1 1 calc R
C10 C 0.2524(7) 0.3169(6) 0.8920(5) 0.0601(13) Uani 1 1 d .
H10A H 0.1687 0.3503 0.8313 0.072 Uiso 1 1 calc R
H10B H 0.2143 0.3565 0.9491 0.072 Uiso 1 1 calc R
C11 C 0.2411(8) 0.1637(6) 0.9437(5) 0.0602(13) Uani 1 1 d .
C12 C 0.1648(10) 0.0977(8) 1.0438(5) 0.0746(17) Uani 1 1 d .
H12 H 0.1642 0.0018 1.0674 0.090 Uiso 1 1 calc R
C13 C 0.3190(12) 0.0847(9) 0.8715(7) 0.087(2) Uani 1 1 d .
H13A H 0.4488 0.0964 0.8609 0.131 Uiso 1 1 calc R
H13B H 0.2655 0.1188 0.7990 0.131 Uiso 1 1 calc R
H13C H 0.2924 -0.0116 0.9085 0.131 Uiso 1 1 calc R
C14 C 0.2421(8) 0.9354(7) 0.4809(5) 0.0623(14) Uani 1 1 d .
C15 C 0.5357(7) 0.7557(7) 0.4878(5) 0.0571(13) Uani 1 1 d .
C16 C 0.3896(8) 0.8328(7) 0.6676(5) 0.0611(14) Uani 1 1 d .
N1 N 0.4360(5) 0.3639(5) 0.8465(3) 0.0508(10) Uani 1 1 d .
O1 O 0.1903(7) 1.0423(6) 0.4313(5) 0.0917(15) Uani 1 1 d .
O2 O 0.6677(6) 0.7444(6) 0.4400(4) 0.0871(16) Uani 1 1 d .
O3 O 0.4342(7) 0.8773(6) 0.7324(5) 0.0914(15) Uani 1 1 d .
Fe1 Fe 0.32530(9) 0.76457(8) 0.56363(6) 0.0475(3) Uani 1 1 d .
Br1 Br 0.05542(15) 0.17855(12) 1.14536(7) 0.1082(4) Uani 1 1 d .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C3 C2 C1 120.7(5)
C3 C2 Fe1 66.8(3)
C1 C2 Fe1 122.5(5)
C4 C3 C2 118.1(5)
C4 C3 Fe1 69.0(3)
C2 C3 Fe1 74.1(3)
C3 C4 C5 118.7(5)
C3 C4 Fe1 70.7(3)
C5 C4 Fe1 72.3(3)
C4 C5 C6 119.9(4)
C4 C5 Fe1 67.5(3)
C6 C5 Fe1 124.8(4)
N1 C6 C5 112.7(4)
N1 C6 C7 102.2(4)
C5 C6 C7 113.8(4)
C8 C7 C6 103.7(5)
C9 C8 C7 105.5(5)
N1 C9 C8 104.5(5)
N1 C10 C11 112.8(5)
C12 C11 C10 124.1(6)
C12 C11 C13 119.9(7)
C10 C11 C13 116.0(6)
C11 C12 Br1 126.1(6)
O1 C14 Fe1 178.6(6)
O2 C15 Fe1 177.0(6)
O3 C16 Fe1 178.4(5)
C10 N1 C6 113.2(4)
C10 N1 C9 113.1(4)
C6 N1 C9 104.5(4)
C15 Fe1 C16 103.3(3)
C15 Fe1 C14 101.5(3)
C16 Fe1 C14 88.4(3)
C15 Fe1 C4 129.9(3)
C16 Fe1 C4 96.9(2)
C14 Fe1 C4 124.7(2)
C15 Fe1 C3 127.0(2)
C16 Fe1 C3 127.2(2)
C14 Fe1 C3 95.5(3)
C4 Fe1 C3 40.3(2)
C15 Fe1 C5 92.8(2)
C16 Fe1 C5 93.1(3)
C14 Fe1 C5 164.9(2)
C4 Fe1 C5 40.21(19)
C3 Fe1 C5 71.7(2)
C15 Fe1 C2 89.4(2)
C16 Fe1 C2 166.3(2)
C14 Fe1 C2 94.3(3)
C4 Fe1 C2 70.6(2)
C3 Fe1 C2 39.2(2)
C5 Fe1 C2 80.8(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.516(8)
C2 C3 1.414(8)
C2 Fe1 2.153(5)
C3 C4 1.408(8)
C3 Fe1 2.057(5)
C4 C5 1.422(7)
C4 Fe1 2.035(6)
C5 C6 1.512(7)
C5 Fe1 2.097(5)
C6 N1 1.466(7)
C6 C7 1.543(7)
C7 C8 1.538(9)
C8 C9 1.520(10)
C9 N1 1.471(6)
C10 N1 1.460(7)
C10 C11 1.488(9)
C11 C12 1.302(9)
C11 C13 1.502(9)
C12 Br1 1.889(7)
C14 O1 1.126(8)
C14 Fe1 1.810(6)
C15 O2 1.133(7)
C15 Fe1 1.781(5)
C16 O3 1.140(7)
C16 Fe1 1.791(6)
