#------------------------------------------------------------------------------
#$Date: 2016-03-21 08:23:24 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178605 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/16/4071644.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_4071644
loop_
_publ_author_name
'Banide, Emilie V.'
'Ortin, Yannick'
'Chamiot, Bénédicte'
'Cassidy, Andrew'
'Niehaus, Jan'
'Moore, Angela'
'Seward, Corey M.'
'Müller-Bunz, Helge'
'McGlinchey, Michael J.'
_publ_section_title
;
 Syntheses, Structures, and Dimerizations of Ferrocenyl- and
 Fluorenylideneallenes: Push−Pull Multiple Bonds?
;
_journal_issue                   16
_journal_name_full               Organometallics
_journal_page_first              4173
_journal_paper_doi               10.1021/om800293m
_journal_volume                  27
_journal_year                    2008
_chemical_formula_moiety         'C7 H4 N2 O2, C7 H5 N2 O2, B F4'
_chemical_formula_sum            'C14 H9 B F4 N4 O4'
_chemical_formula_weight         384.06
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.0970(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.0959(10)
_cell_length_b                   7.1079(4)
_cell_length_c                   14.3430(9)
_cell_measurement_reflns_used    6975
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.32
_cell_volume                     1550.65(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and 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  0.0139
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11493
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.68
_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_T_max  0.9145
_exptl_absorpt_correction_T_min  0.8078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.645
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.80
_exptl_crystal_size_min          0.60
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         3042
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0405P)²+0.6686P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0808
_reflns_number_gt                2822
_reflns_number_total             3042
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om800293m-file002.cif
_cod_data_source_block           mjm32
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4071644
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
C1 C 0.58273(8) 0.08100(16) 0.24945(9) 0.0164(2) Uani 1 1 d .
C7 C 0.58007(8) 0.05314(17) 0.14469(9) 0.0168(2) Uani 1 1 d .
O1 O 0.64912(5) 0.02572(13) 0.12825(6) 0.0202(2) Uani 1 1 d .
O2 O 0.50280(6) 0.05843(14) 0.08106(6) 0.0234(2) Uani 1 1 d .
H1O2 H 0.5000 0.0000 0.0000 0.035 Uiso 1 2 d S
C2 C 0.66206(8) 0.08041(17) 0.32760(9) 0.0165(2) Uani 1 1 d .
N1 N 0.74244(7) 0.05728(14) 0.30899(7) 0.0165(2) Uani 1 1 d .
N2 N 0.80955(7) 0.04052(16) 0.30760(8) 0.0214(2) Uani 1 1 d .
C3 C 0.66941(9) 0.09776(18) 0.42590(9) 0.0208(3) Uani 1 1 d .
H3 H 0.7276(11) 0.095(2) 0.4749(12) 0.028(4) Uiso 1 1 d .
C4 C 0.59261(9) 0.11943(19) 0.44827(10) 0.0230(3) Uani 1 1 d .
H4 H 0.5949(10) 0.135(2) 0.5149(12) 0.024(4) Uiso 1 1 d .
C5 C 0.51220(9) 0.12147(19) 0.37313(10) 0.0225(3) Uani 1 1 d .
H5 H 0.4600(10) 0.135(2) 0.3889(11) 0.020(4) Uiso 1 1 d .
C6 C 0.50731(8) 0.10166(18) 0.27514(9) 0.0199(3) Uani 1 1 d .
H6 H 0.4521(10) 0.102(2) 0.2233(11) 0.023(4) Uiso 1 1 d .
C8 C 0.08309(8) 0.39531(17) 0.42299(8) 0.0168(2) Uani 1 1 d .
C14 C 0.07909(8) 0.20284(18) 0.46554(8) 0.0173(2) Uani 1 1 d .
O3 O 0.14823(6) 0.11890(13) 0.50544(7) 0.0226(2) Uani 1 1 d .
O4 O 0.00144(6) 0.14591(13) 0.45548(7) 0.0245(2) Uani 1 1 d .
H1O4 H 0.0000 0.0000 0.5000 0.037 Uiso 1 2 d S
C9 C 0.16317(8) 0.47607(18) 0.42699(8) 0.0168(2) Uani 1 1 d .
N3 N 0.24220(7) 0.37775(16) 0.47400(8) 0.0204(2) Uani 1 1 d .
N4 N 0.30813(7) 0.32032(18) 0.50856(9) 0.0310(3) Uani 1 1 d .
C10 C 0.17302(8) 0.65126(18) 0.38965(9) 0.0184(3) Uani 1 1 d .
H10 H 0.2298(10) 0.693(2) 0.3928(11) 0.022(4) Uiso 1 1 d .
C11 C 0.09735(8) 0.75425(18) 0.34634(9) 0.0201(3) Uani 1 1 d .
H11 H 0.1008(9) 0.874(2) 0.3212(11) 0.021(4) Uiso 1 1 d .
C12 C 0.01606(8) 0.68060(19) 0.34097(9) 0.0216(3) Uani 1 1 d .
H12 H -0.0373(10) 0.755(2) 0.3111(11) 0.026(4) Uiso 1 1 d .
C13 C 0.00901(8) 0.50291(18) 0.37836(9) 0.0193(3) Uani 1 1 d .
H13 H -0.0473(10) 0.454(2) 0.3747(11) 0.021(4) Uiso 1 1 d .
B B 0.25110(9) 0.0566(2) 0.24069(11) 0.0211(3) Uani 1 1 d .
F1 F 0.30431(5) 0.18322(11) 0.21297(6) 0.02689(19) Uani 1 1 d .
F2 F 0.19174(5) 0.15394(12) 0.27487(6) 0.0318(2) Uani 1 1 d .
F3 F 0.30233(6) -0.06169(13) 0.31389(7) 0.0386(2) Uani 1 1 d .
F4 F 0.20545(5) -0.05143(12) 0.15875(7) 0.0346(2) 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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C6 C1 C2 115.91(11)
C6 C1 C7 122.59(11)
C2 C1 C7 121.45(11)
O1 C7 O2 126.76(11)
O1 C7 C1 118.87(10)
O2 C7 C1 114.35(10)
C7 O2 H1O2 113.17(9)
C3 C2 C1 124.71(11)
C3 C2 N1 115.15(10)
C1 C2 N1 120.12(11)
N2 N1 C2 170.70(11)
C2 C3 C4 117.51(12)
C2 C3 H3 118.5(9)
C4 C3 H3 124.0(9)
C3 C4 C5 119.89(12)
C3 C4 H4 120.1(9)
C5 C4 H4 120.0(9)
C4 C5 C6 120.98(12)
C4 C5 H5 119.5(9)
C6 C5 H5 119.5(9)
C1 C6 C5 120.98(12)
C1 C6 H6 117.9(9)
C5 C6 H6 121.1(9)
C13 C8 C9 115.85(11)
C13 C8 C14 122.96(11)
C9 C8 C14 121.19(11)
O3 C14 O4 127.14(12)
O3 C14 C8 118.54(10)
O4 C14 C8 114.31(10)
H1O4 O4 C14 113.28(9)
C14 O4 H1O4 113.28(9)
C10 C9 C8 125.12(11)
C10 C9 N3 115.45(11)
C8 C9 N3 119.42(11)
N4 N3 C9 171.63(12)
C11 C10 C9 117.03(11)
C11 C10 H10 123.3(9)
C9 C10 H10 119.6(9)
C10 C11 C12 120.09(12)
C10 C11 H11 120.1(9)
C12 C11 H11 119.8(9)
C11 C12 C13 121.02(12)
C11 C12 H12 119.8(9)
C13 C12 H12 119.2(9)
C8 C13 C12 120.88(12)
C8 C13 H13 118.9(9)
C12 C13 H13 120.3(9)
F3 B F1 109.90(10)
F3 B F2 109.96(12)
F1 B F2 109.74(11)
F3 B F4 108.84(11)
F1 B F4 108.67(11)
F2 B F4 109.71(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C6 1.3869(17)
C1 C2 1.3965(16)
C1 C7 1.5022(17)
C7 O1 1.2249(15)
C7 O2 1.2801(15)
O2 H1O2 1.2214(9)
C2 C3 1.3813(17)
C2 N1 1.4135(15)
N1 N2 1.0934(15)
C3 C4 1.3835(19)
C3 H3 0.971(16)
C4 C5 1.3872(19)
C4 H4 0.950(16)
C5 C6 1.3889(18)
C5 H5 0.945(15)
C6 H6 0.954(15)
C8 C13 1.3845(17)
C8 C9 1.3950(17)
C8 C14 1.5079(17)
C14 O3 1.2268(15)
C14 O4 1.2763(15)
O4 H1O4 1.2222(9)
O4 H1O4 1.2222(9)
C9 C10 1.3849(18)
C9 N3 1.4142(16)
N3 N4 1.0928(15)
C10 C11 1.3821(18)
C10 H10 0.947(16)
C11 C12 1.3879(18)
C11 H11 0.934(16)
C12 C13 1.3912(19)
C12 H12 0.978(16)
C13 H13 0.955(15)
B F3 1.3866(17)
B F1 1.3872(16)
B F2 1.3922(17)
B F4 1.3950(17)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H1O4 O4 1.22 1.22 2.4443(18) 180 3_556
O2 H1O2 O2 1.22 1.22 2.4428(17) 180 3_655
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
C6 C1 C7 O1 -176.08(12)
C2 C1 C7 O1 1.45(18)
C6 C1 C7 O2 2.92(17)
C2 C1 C7 O2 -179.55(11)
C6 C1 C2 C3 0.32(19)
C7 C1 C2 C3 -177.36(12)
C6 C1 C2 N1 179.05(11)
C7 C1 C2 N1 1.37(17)
C1 C2 C3 C4 -0.77(19)
N1 C2 C3 C4 -179.56(11)
C2 C3 C4 C5 0.53(19)
C3 C4 C5 C6 0.1(2)
C2 C1 C6 C5 0.37(18)
C7 C1 C6 C5 178.03(12)
C4 C5 C6 C1 -0.6(2)
C13 C8 C14 O3 -178.63(11)
C9 C8 C14 O3 1.11(17)
C13 C8 C14 O4 1.12(17)
C9 C8 C14 O4 -179.14(11)
O3 C14 O4 H1O4 7.58(18)
C8 C14 O4 H1O4 -172.14(8)
C13 C8 C9 C10 -0.47(18)
C14 C8 C9 C10 179.78(11)
C13 C8 C9 N3 178.13(11)
C14 C8 C9 N3 -1.63(17)
C8 C9 C10 C11 0.91(18)
N3 C9 C10 C11 -177.74(11)
C9 C10 C11 C12 -0.51(18)
C10 C11 C12 C13 -0.26(19)
C9 C8 C13 C12 -0.36(17)
C14 C8 C13 C12 179.39(11)
C11 C12 C13 C8 0.72(19)
