#------------------------------------------------------------------------------
#$Date: 2016-06-17 01:56:06 +0300 (Fri, 17 Jun 2016) $
#$Revision: 183605 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/64/4086476.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_4086476
loop_
_publ_author_name
'Korb, Marcus'
'Swarts, Pieter J.'
'Miesel, Dominique'
'Hildebrandt, Alexander'
'Swarts, Jannie C.'
'Lang, Heinrich'
_publ_section_title
;
 Nucleophilic Aromatic Substitution Reactions for the Synthesis of
 Ferrocenyl Aryl Ethers
;
_journal_issue                   9
_journal_name_full               Organometallics
_journal_page_first              1287
_journal_paper_doi               10.1021/acs.organomet.6b00157
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C6 H2 F2 N2 O4'
_chemical_formula_sum            'C6 H2 F2 N2 O4'
_chemical_formula_weight         204.10
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_Hall           'P 4nw 2abw'
_space_group_name_H-M_alt        'P 43 21 2'
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8849(2)
_cell_length_b                   5.8849(2)
_cell_length_c                   21.4266(9)
_cell_measurement_reflns_used    1434
_cell_measurement_temperature    110(5)
_cell_measurement_theta_max      25.9620
_cell_measurement_theta_min      3.5770
_cell_volume                     742.05(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      110(5)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'oxford gemini s'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0694
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3024
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.590
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 50
_diffrn_standards_interval_time  10
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 174 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         647
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0421P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0869
_reflns_Friedel_coverage         0.477
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                587
_reflns_number_total             647
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om6b00157_si_002.cif
_cod_data_source_block           MK-385
_cod_depositor_comments
'Adding full bibliography for 4086474--4086481.cif.'
_cod_original_cell_volume        742.05(6)
_cod_database_code               4086476
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+3/4'
'y+1/2, -x+1/2, z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-y, -x, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.3423(5) 0.2490(4) 0.97276(12) 0.0173(6) Uani 1 1 d . .
C2 C 0.5348(5) 0.3413(5) 0.94659(12) 0.0198(7) Uani 1 1 d . .
H2 H 0.6001 0.2770 0.9112 0.024 Uiso 1 1 calc R U
C3 C 0.6283(5) 0.5305(5) 0.97389(12) 0.0212(7) Uani 1 1 d . .
N1 N 0.2264(4) 0.0667(4) 0.93889(10) 0.0211(6) Uani 1 1 d . .
O1 O 0.3443(4) -0.0785(3) 0.91377(9) 0.0301(6) Uani 1 1 d . .
O2 O 0.0180(3) 0.0750(4) 0.93624(8) 0.0269(6) Uani 1 1 d . .
F1 F 0.8169(3) 0.6232(3) 0.94993(7) 0.0334(6) 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 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C1 120.49(16) . 7_557
C2 C1 N1 118.1(2) . .
C1 C1 N1 121.15(15) 7_557 .
C3 C2 C1 118.4(2) . .
C3 C2 H2 120.8 . .
C1 C2 H2 120.8 . .
F1 C3 C2 119.9(2) . .
F1 C3 C3 119.03(13) . 7_557
C2 C3 C3 121.02(16) . 7_557
O1 N1 O2 124.9(3) . .
O1 N1 C1 117.7(2) . .
O2 N1 C1 117.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.376(4) .
C1 C1 1.402(5) 7_557
C1 N1 1.464(3) .
C2 C3 1.373(4) .
C2 H2 0.9300 .
C3 F1 1.339(3) .
C3 C3 1.384(5) 7_557
N1 O1 1.226(3) .
N1 O2 1.229(3) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C1 C1 C2 C3 -2.1(5) 7_557 .
N1 C1 C2 C3 172.0(3) . .
C1 C2 C3 F1 179.4(2) . .
C1 C2 C3 C3 -0.7(5) . 7_557
C2 C1 N1 O1 41.0(3) . .
C1 C1 N1 O1 -144.9(3) 7_557 .
C2 C1 N1 O2 -136.8(3) . .
C1 C1 N1 O2 37.2(4) 7_557 .
