#------------------------------------------------------------------------------
#$Date: 2017-04-05 13:03:48 +0300 (Wed, 05 Apr 2017) $
#$Revision: 195156 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/59/7055981.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_7055981
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 Br2 Cl2 Fe N4'
_chemical_formula_weight         502.86
_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                 92.4070(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1777(13)
_cell_length_b                   8.7316(9)
_cell_length_c                   17.3452(18)
_cell_measurement_temperature    296(2)
_cell_volume                     1842.7(3)
_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_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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0353
_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       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            19914
_diffrn_reflns_theta_full        27.09
_diffrn_reflns_theta_max         27.09
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    5.443
_exptl_absorpt_correction_T_max  0.3110
_exptl_absorpt_correction_T_min  0.1932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            light-blue
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.531
_refine_diff_density_min         -1.016
_refine_diff_density_rms         0.125
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         4050
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0412
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0457P)²+2.1565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1018
_reflns_number_gt                3201
_reflns_number_total             4050
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6nj03822k2.cif
_cod_data_source_block           evg084_0m
_cod_depositor_comments
'Adding full bibliography for 7055976--7055983.cif.'
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7055981
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 0.17276(4) 0.21480(6) 0.44846(3) 0.03743(15) Uani 1 1 d .
Br1 Br -0.17048(4) 0.42458(6) 0.21701(3) 0.06252(16) Uani 1 1 d .
Br2 Br 0.61254(3) 0.47407(6) 0.37903(3) 0.05735(15) Uani 1 1 d .
Cl1 Cl 0.20580(13) 0.00902(14) 0.37417(11) 0.0887(5) Uani 1 1 d .
Cl2 Cl 0.13636(10) 0.20965(17) 0.57340(7) 0.0682(4) Uani 1 1 d .
N1 N 0.0662(2) 0.3539(3) 0.38239(15) 0.0313(6) Uani 1 1 d .
N2 N 0.0966(2) 0.4943(3) 0.35429(15) 0.0290(6) Uani 1 1 d .
N3 N 0.3015(2) 0.3666(3) 0.43028(16) 0.0318(6) Uani 1 1 d .
N4 N 0.2869(2) 0.5025(3) 0.39205(16) 0.0293(6) Uani 1 1 d .
C1 C -0.0805(4) 0.1640(5) 0.3542(3) 0.0529(10) Uani 1 1 d .
H1A H -0.0574 0.0920 0.3164 0.079 Uiso 1 1 calc R
H1B H -0.1587 0.1770 0.3492 0.079 Uiso 1 1 calc R
H1C H -0.0608 0.1264 0.4049 0.079 Uiso 1 1 calc R
C2 C -0.0254(3) 0.3145(4) 0.34205(19) 0.0347(8) Uani 1 1 d .
C3 C -0.0535(3) 0.4302(4) 0.29000(19) 0.0349(8) Uani 1 1 d .
C4 C 0.0243(3) 0.5447(4) 0.29875(19) 0.0341(7) Uani 1 1 d .
C5 C 0.0337(4) 0.6947(5) 0.2596(2) 0.0546(11) Uani 1 1 d .
H5A H 0.0338 0.7752 0.2973 0.082 Uiso 1 1 calc R
H5B H -0.0275 0.7080 0.2235 0.082 Uiso 1 1 calc R
H5C H 0.1009 0.6979 0.2326 0.082 Uiso 1 1 calc R
C6 C 0.4569(4) 0.1967(5) 0.4679(3) 0.0543(11) Uani 1 1 d .
H6A H 0.4155 0.1704 0.5120 0.082 Uiso 1 1 calc R
H6B H 0.5321 0.2151 0.4841 0.082 Uiso 1 1 calc R
H6C H 0.4534 0.1140 0.4315 0.082 Uiso 1 1 calc R
C7 C 0.4097(3) 0.3377(4) 0.43106(19) 0.0351(8) Uani 1 1 d .
C8 C 0.4624(3) 0.4562(4) 0.39487(19) 0.0341(7) Uani 1 1 d .
C9 C 0.3840(3) 0.5607(4) 0.36990(19) 0.0322(7) Uani 1 1 d .
C10 C 0.3950(4) 0.7067(5) 0.3270(3) 0.0525(10) Uani 1 1 d .
H10A H 0.3593 0.6973 0.2769 0.079 Uiso 1 1 calc R
H10B H 0.4714 0.7293 0.3216 0.079 Uiso 1 1 calc R
H10C H 0.3614 0.7880 0.3549 0.079 Uiso 1 1 calc R
C11 C 0.1824(3) 0.5825(4) 0.39409(19) 0.0294(7) Uani 1 1 d .
H11 H 0.1900 0.6787 0.3657 0.035 Uiso 1 1 calc R
C12 C 0.1525(3) 0.6236(5) 0.4760(2) 0.0417(8) Uani 1 1 d .
H12A H 0.0844 0.6792 0.4745 0.063 Uiso 1 1 calc R
H12B H 0.2095 0.6859 0.4996 0.063 Uiso 1 1 calc R
H12C H 0.1447 0.5316 0.5056 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'
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'
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 90.06(11)
N1 Fe1 Cl2 113.65(9)
N3 Fe1 Cl2 109.92(9)
N1 Fe1 Cl1 105.77(9)
N3 Fe1 Cl1 105.45(9)
Cl2 Fe1 Cl1 125.88(6)
C2 N1 N2 106.0(3)
C2 N1 Fe1 128.6(2)
N2 N1 Fe1 122.9(2)
C4 N2 N1 111.5(3)
C4 N2 C11 127.0(3)
N1 N2 C11 120.3(2)
C7 N3 N4 106.0(3)
C7 N3 Fe1 128.5(2)
N4 N3 Fe1 122.8(2)
C9 N4 N3 111.5(3)
C9 N4 C11 127.0(3)
N3 N4 C11 120.0(3)
N1 C2 C3 109.3(3)
N1 C2 C1 121.5(3)
C3 C2 C1 129.2(3)
C4 C3 C2 107.8(3)
C4 C3 Br1 126.5(3)
C2 C3 Br1 125.6(3)
N2 C4 C3 105.4(3)
N2 C4 C5 123.7(3)
C3 C4 C5 130.9(3)
N3 C7 C8 109.3(3)
N3 C7 C6 121.3(3)
C8 C7 C6 129.4(3)
C9 C8 C7 108.0(3)
C9 C8 Br2 124.7(3)
C7 C8 Br2 127.3(3)
N4 C9 C8 105.3(3)
N4 C9 C10 124.2(3)
C8 C9 C10 130.5(3)
N2 C11 N4 110.4(3)
N2 C11 C12 111.9(3)
N4 C11 C12 112.3(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Fe1 N1 2.085(3)
Fe1 N3 2.086(3)
Fe1 Cl2 2.2307(13)
Fe1 Cl1 2.2571(14)
Br1 C3 1.867(3)
Br2 C8 1.866(3)
N1 C2 1.336(4)
N1 N2 1.375(4)
N2 C4 1.351(4)
N2 C11 1.450(4)
N3 C7 1.341(4)
N3 N4 1.367(4)
N4 C9 1.356(4)
N4 C11 1.454(4)
C1 C2 1.495(5)
C2 C3 1.388(5)
C3 C4 1.381(5)
C4 C5 1.482(5)
C6 C7 1.491(5)
C7 C8 1.382(5)
C8 C9 1.378(5)
C9 C10 1.485(5)
C11 C12 1.525(5)
