#------------------------------------------------------------------------------
#$Date: 2017-04-05 13:03:48 +0300 (Wed, 05 Apr 2017) $
#$Revision: 195156 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/59/7055982.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_7055982
loop_
_publ_author_name
'Govor, Evgen V.'
'Sanakis, Yiannis'
'Raptis, Raphael G.'
_publ_section_title
;
 Synthesis of pyrazole (hemi)aminals via the cleavage of saturated
 aliphatic ether C--O bonds in the presence of ferric halides
;
_journal_issue                   6
_journal_name_full               'New J. Chem.'
_journal_page_first              2220
_journal_paper_doi               10.1039/C6NJ03822K
_journal_volume                  41
_journal_year                    2017
_chemical_formula_sum            'C12 H16 Br4 Fe N4'
_chemical_formula_weight         591.78
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2013-06-02 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.930(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.247(4)
_cell_length_b                   8.932(3)
_cell_length_c                   17.420(5)
_cell_measurement_temperature    296(2)
_cell_volume                     1904.5(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0492
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18641
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    9.181
_exptl_absorpt_correction_T_max  0.2487
_exptl_absorpt_correction_T_min  0.1168
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.064
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.725
_refine_diff_density_min         -1.018
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         3870
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0458P)²+4.4370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1049
_reflns_number_gt                3148
_reflns_number_total             3870
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6nj03822k2.cif
_cod_data_source_block           evg085_2_abs_cor
_cod_depositor_comments
'Adding full bibliography for 7055976--7055983.cif.'
_cod_original_cell_volume        1904.6(9)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7055982
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
Fe1 Fe 0.32640(5) 0.72106(7) 0.05312(4) 0.03497(17) Uani 1 1 d .
Br1 Br -0.11477(4) 0.96618(8) 0.12003(4) 0.05931(19) Uani 1 1 d .
Br2 Br 0.66566(4) 0.92918(8) 0.28199(3) 0.06146(19) Uani 1 1 d .
Br3 Br 0.29202(6) 0.50617(7) 0.13137(5) 0.0776(2) Uani 1 1 d .
Br4 Br 0.36471(5) 0.71044(8) -0.07900(3) 0.0624(2) Uani 1 1 d .
N1 N 0.1969(3) 0.8656(4) 0.0706(2) 0.0316(8) Uani 1 1 d .
N2 N 0.2091(3) 0.9979(4) 0.1097(2) 0.0285(8) Uani 1 1 d .
N3 N 0.4315(3) 0.8581(4) 0.1182(2) 0.0312(8) Uani 1 1 d .
N4 N 0.3986(3) 0.9926(4) 0.1477(2) 0.0284(7) Uani 1 1 d .
C1 C 0.0445(4) 0.7000(6) 0.0304(3) 0.0510(13) Uani 1 1 d .
H1A H 0.0826 0.6810 -0.0158 0.076 Uiso 1 1 calc R
H1B H -0.0318 0.7145 0.0181 0.076 Uiso 1 1 calc R
H1C H 0.0534 0.6163 0.0646 0.076 Uiso 1 1 calc R
C2 C 0.0896(4) 0.8367(5) 0.0682(2) 0.0340(10) Uani 1 1 d .
C3 C 0.0352(3) 0.9508(5) 0.1048(2) 0.0337(10) Uani 1 1 d .
C4 C 0.1117(3) 1.0537(5) 0.1307(2) 0.0317(9) Uani 1 1 d .
C5 C 0.0980(4) 1.1962(6) 0.1734(3) 0.0517(13) Uani 1 1 d .
H5A H 0.1399 1.1921 0.2210 0.078 Uiso 1 1 calc R
H5B H 0.0222 1.2104 0.1838 0.078 Uiso 1 1 calc R
H5C H 0.1231 1.2781 0.1430 0.078 Uiso 1 1 calc R
C6 C 0.5813(4) 0.6773(6) 0.1434(3) 0.0518(13) Uani 1 1 d .
H6A H 0.5513 0.6310 0.0977 0.078 Uiso 1 1 calc R
H6B H 0.5728 0.6114 0.1863 0.078 Uiso 1 1 calc R
H6C H 0.6576 0.6971 0.1372 0.078 Uiso 1 1 calc R
C7 C 0.5231(3) 0.8204(5) 0.1574(3) 0.0335(10) Uani 1 1 d .
C8 C 0.5489(3) 0.9328(5) 0.2107(2) 0.0344(10) Uani 1 1 d .
C9 C 0.4696(3) 1.0420(5) 0.2035(2) 0.0308(9) Uani 1 1 d .
C10 C 0.4576(4) 1.1855(6) 0.2446(3) 0.0492(13) Uani 1 1 d .
H10A H 0.4596 1.2667 0.2086 0.074 Uiso 1 1 calc R
H10B H 0.5163 1.1965 0.2821 0.074 Uiso 1 1 calc R
H10C H 0.3891 1.1866 0.2698 0.074 Uiso 1 1 calc R
C11 C 0.3127(3) 1.0783(5) 0.1086(2) 0.0290(9) Uani 1 1 d .
H11 H 0.3037 1.1712 0.1376 0.035 Uiso 1 1 calc R
C12 C 0.3433(4) 1.1220(6) 0.0277(3) 0.0421(11) Uani 1 1 d .
H12A H 0.4122 1.1734 0.0297 0.063 Uiso 1 1 calc R
H12B H 0.2881 1.1866 0.0056 0.063 Uiso 1 1 calc R
H12C H 0.3490 1.0336 -0.0032 0.063 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'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
N1 Fe1 N3 90.91(14)
N1 Fe1 Br4 110.17(11)
N3 Fe1 Br4 114.42(11)
N1 Fe1 Br3 105.37(11)
N3 Fe1 Br3 106.14(11)
Br4 Fe1 Br3 124.39(4)
C2 N1 N2 105.8(3)
C2 N1 Fe1 129.0(3)
N2 N1 Fe1 122.6(3)
C4 N2 N1 111.7(3)
C4 N2 C11 126.6(4)
N1 N2 C11 119.9(3)
C7 N3 N4 106.3(3)
C7 N3 Fe1 128.5(3)
N4 N3 Fe1 122.3(3)
C9 N4 N3 111.4(3)
C9 N4 C11 127.0(4)
N3 N4 C11 120.1(3)
N1 C2 C3 109.3(4)
N1 C2 C1 121.5(4)
C3 C2 C1 129.2(4)
C4 C3 C2 108.0(4)
C4 C3 Br1 124.4(4)
C2 C3 Br1 127.6(3)
N2 C4 C3 105.1(4)
N2 C4 C5 124.4(4)
C3 C4 C5 130.4(4)
N3 C7 C8 109.1(4)
N3 C7 C6 122.1(4)
C8 C7 C6 128.8(4)
C9 C8 C7 107.7(4)
C9 C8 Br2 126.6(3)
C7 C8 Br2 125.6(3)
N4 C9 C8 105.6(4)
N4 C9 C10 123.9(4)
C8 C9 C10 130.5(4)
N4 C11 N2 110.5(3)
N4 C11 C12 111.9(4)
N2 C11 C12 112.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Fe1 N1 2.075(4)
Fe1 N3 2.083(4)
Fe1 Br4 2.3662(11)
Fe1 Br3 2.3997(10)
Br1 C3 1.869(4)
Br2 C8 1.861(4)
N1 C2 1.339(5)
N1 N2 1.369(5)
N2 C4 1.355(5)
N2 C11 1.460(5)
N3 C7 1.336(5)
N3 N4 1.373(5)
N4 C9 1.355(5)
N4 C11 1.452(5)
C1 C2 1.484(7)
C2 C3 1.385(7)
C3 C4 1.378(6)
C4 C5 1.486(7)
C6 C7 1.488(7)
C7 C8 1.397(6)
C8 C9 1.379(6)
C9 C10 1.479(7)
C11 C12 1.520(6)
