#------------------------------------------------------------------------------
#$Date: 2016-03-21 09:44:17 +0100 (lun 21 de mar de 2016) $
#$Revision: 178665 $
#$URL: svn://www.crystallography.net/cod/cif/4/07/76/4077649.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_4077649
loop_
_publ_author_name
'Ding, Li'
'Fabrizi de Biani, Fabrizia'
'Bolte, Michael'
'Zanello, Piero'
'Wagner, Matthias'
_publ_section_title
;
 Reactivity of Ferrocenylboranes:  Rearrangements versus Electron
 Transfer Reactions
;
_journal_issue                   26
_journal_name_full               Organometallics
_journal_page_first              5763
_journal_paper_doi               10.1021/om000727w
_journal_volume                  19
_journal_year                    2000
_chemical_formula_sum            'C12 H8 N4 O2'
_chemical_formula_weight         240.22
_chemical_name_systematic        ?
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.08(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.000(1)
_cell_length_b                   6.363(1)
_cell_length_c                   10.242(1)
_cell_measurement_reflns_used    2334
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      1
_cell_volume                     514.83(12)
_computing_cell_refinement       'Siemens SMART'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SAINT'
_computing_molecular_graphics    'XP (Siemens XTL-Plus)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Siemens CCD three-circle diffractometer'
_diffrn_measurement_method       ω
_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  0.0605
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4943
_diffrn_reflns_theta_full        28.69
_diffrn_reflns_theta_max         28.69
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  840
_diffrn_standards_number         67
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9890
_exptl_absorpt_correction_T_min  0.9568
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.025(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     56
_refine_ls_number_reflns         725
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0405
_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)+(0.0732P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1146
_reflns_number_gt                523
_reflns_number_total             725
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            om000727w.cif
_cod_data_source_block           1_(wa1)
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

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 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        514.83(11)
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               4077649
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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
C11 C 0.4124(2) 0.0000 0.36537(17) 0.0196(4) Uani 1 2 d S
O1 O 0.33546(15) 0.0000 0.25247(12) 0.0272(4) Uani 1 2 d S
C12 C 0.60306(19) 0.0000 0.39604(17) 0.0195(4) Uani 1 2 d S
C13 C 0.6798(2) 0.0000 0.52165(17) 0.0205(4) Uani 1 2 d S
H13 H 0.8000 0.0000 0.5387 0.025 Uiso 1 2 calc SR
N21 N 0.69618(17) 0.0000 0.29013(15) 0.0218(4) Uani 1 2 d S
N22 N 0.87078(17) 0.0000 0.32019(16) 0.0258(4) Uani 1 2 d S
C23 C 0.9213(2) 0.0000 0.20317(19) 0.0272(4) Uani 1 2 d S
H23 H 1.0368 0.0000 0.1916 0.033 Uiso 1 2 calc SR
C24 C 0.7861(2) 0.0000 0.09837(19) 0.0339(5) Uani 1 2 d S
H24 H 0.7917 0.0000 0.0064 0.041 Uiso 1 2 calc SR
C25 C 0.6443(2) 0.0000 0.15687(19) 0.0343(5) Uani 1 2 d S
H25 H 0.5305 0.0000 0.1129 0.041 Uiso 1 2 calc SR
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C11 0.0172(8) 0.0223(8) 0.0187(10) 0.000 0.0014(7) 0.000
O1 0.0195(6) 0.0453(9) 0.0155(7) 0.000 -0.0011(5) 0.000
C12 0.0157(7) 0.0239(8) 0.0194(9) 0.000 0.0040(6) 0.000
C13 0.0141(7) 0.0266(9) 0.0207(9) 0.000 0.0023(6) 0.000
N21 0.0142(7) 0.0336(8) 0.0177(8) 0.000 0.0030(6) 0.000
N22 0.0138(7) 0.0416(9) 0.0221(9) 0.000 0.0027(6) 0.000
C23 0.0201(9) 0.0404(11) 0.0226(10) 0.000 0.0077(8) 0.000
C24 0.0262(9) 0.0579(13) 0.0186(10) 0.000 0.0068(8) 0.000
C25 0.0209(9) 0.0650(14) 0.0163(10) 0.000 0.0011(7) 0.000
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'
O O 0.0106 0.0060 '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
O1 C11 C13 120.40(15) . 5_656
O1 C11 C12 122.64(15) . .
C13 C11 C12 116.96(15) 5_656 .
C13 C12 N21 121.55(15) . .
C13 C12 C11 119.78(15) . .
N21 C12 C11 118.67(15) . .
C12 C13 C11 123.26(15) . 5_656
C25 N21 N22 111.13(14) . .
C25 N21 C12 131.04(15) . .
N22 N21 C12 117.83(15) . .
C23 N22 N21 103.92(15) . .
N22 C23 C24 112.64(17) . .
C25 C24 C23 105.01(18) . .
N21 C25 C24 107.29(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C11 O1 1.221(2) .
C11 C13 1.467(2) 5_656
C11 C12 1.508(2) .
C12 C13 1.335(2) .
C12 N21 1.409(2) .
C13 C11 1.467(2) 5_656
N21 C25 1.362(2) .
N21 N22 1.382(2) .
N22 C23 1.324(3) .
C23 C24 1.399(3) .
C24 C25 1.364(3) .
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
C13 H13 N22 0.95 2.39 2.755(2) 102.1 .
C25 H25 O1 0.95 2.28 2.798(2) 113.7 .
C23 H23 O1 0.95 2.37 3.272(2) 157.9 1_655
C24 H24 O1 0.95 2.69 3.571(2) 155.3 5_655
C13 H13 N22 0.95 2.80 3.703(2) 159.8 5_756
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
O1 C11 C12 C13 180.0 . .
C13 C11 C12 C13 0.0 5_656 .
O1 C11 C12 N21 0.0 . .
C13 C11 C12 N21 180.0 5_656 .
N21 C12 C13 C11 180.0 . 5_656
C11 C12 C13 C11 0.0 . 5_656
C13 C12 N21 C25 180.0 . .
C11 C12 N21 C25 0.0 . .
C13 C12 N21 N22 0.0 . .
C11 C12 N21 N22 180.0 . .
C25 N21 N22 C23 0.0 . .
C12 N21 N22 C23 180.0 . .
N21 N22 C23 C24 0.0 . .
N22 C23 C24 C25 0.0 . .
N22 N21 C25 C24 0.0 . .
C12 N21 C25 C24 180.0 . .
C23 C24 C25 N21 0.0 . .
