#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/61/1516172.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_1516172
loop_
_publ_author_name
'Yu, Changjiang'
'Jiao, Lijuan'
'Zhang, Ping'
'Feng, Zeya'
'Cheng, Chi'
'Wei, Yun'
'Mu, Xiaolong'
'Hao, Erhong'
_publ_section_title
;
 Highly Fluorescent BF2 Complexes of Hydrazine-Schiff Base Linked
 Bispyrrole.
;
_journal_issue                   11
_journal_name_full               'Organic letters'
_journal_page_first              3048
_journal_page_last               3051
_journal_paper_doi               10.1021/ol501162f
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C10 H9 B F2 N4'
_chemical_formula_weight         234.02
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.306(3)
_cell_length_b                   9.480(2)
_cell_length_c                   18.766(4)
_cell_measurement_reflns_used    2238
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.00
_cell_measurement_theta_min      0.00
_cell_volume                     2189.3(8)
_computing_cell_refinement       'Bruker SMART'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0964
_diffrn_reflns_av_sigmaI/netI    0.0677
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17153
_diffrn_reflns_theta_full        27.59
_diffrn_reflns_theta_max         27.59
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_correction_T_min  0.9855
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0051(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.947
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2536
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.947
_refine_ls_R_factor_all          0.1470
_refine_ls_R_factor_gt           0.0474
_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)+(0.0531P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1272
_reflns_number_gt                1098
_reflns_number_total             2536
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501162f_si_002.cif
_cod_data_source_block           140324a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1516169--1516173.cif.
;
_cod_original_cell_volume        2189.4(8)
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               1516172
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-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
B1 B 0.0855(2) 0.1695(3) 0.40653(16) 0.0599(7) Uani 1 1 d .
C1 C 0.0545(2) 0.3363(3) 0.29837(15) 0.0833(8) Uani 1 1 d .
H1 H -0.0196 0.3215 0.2923 0.100 Uiso 1 1 calc R
C2 C 0.1166(3) 0.4273(3) 0.25886(15) 0.0917(9) Uani 1 1 d .
H2 H 0.0924 0.4844 0.2218 0.110 Uiso 1 1 calc R
C3 C 0.2227(3) 0.4187(3) 0.28430(14) 0.0827(8) Uani 1 1 d .
H3 H 0.2824 0.4690 0.2677 0.099 Uiso 1 1 calc R
C4 C 0.2223(2) 0.3208(2) 0.33895(13) 0.0641(7) Uani 1 1 d .
C5 C 0.30609(19) 0.2678(2) 0.38315(14) 0.0634(7) Uani 1 1 d .
H5 H 0.3753 0.3030 0.3742 0.076 Uiso 1 1 calc R
C6 C 0.18615(16) 0.0350(2) 0.49909(12) 0.0554(6) Uani 1 1 d .
H6 H 0.1163 0.0012 0.5073 0.066 Uiso 1 1 calc R
C7 C 0.26549(17) -0.0207(2) 0.54431(12) 0.0537(6) Uani 1 1 d .
C8 C 0.2514(2) -0.1244(3) 0.59523(13) 0.0724(7) Uani 1 1 d .
H8 H 0.1862 -0.1690 0.6060 0.087 Uiso 1 1 calc R
C9 C 0.3496(2) -0.1506(3) 0.62725(14) 0.0767(8) Uani 1 1 d .
H9 H 0.3632 -0.2160 0.6631 0.092 Uiso 1 1 calc R
C10 C 0.4238(2) -0.0616(3) 0.59617(13) 0.0669(7) Uani 1 1 d .
H10 H 0.4972 -0.0563 0.6079 0.080 Uiso 1 1 calc R
F1 F 0.01566(10) 0.23106(14) 0.45576(8) 0.0815(5) Uani 1 1 d .
F2 F 0.03632(11) 0.04866(14) 0.38111(8) 0.0888(5) Uani 1 1 d .
N1 N 0.11805(16) 0.27041(19) 0.34820(10) 0.0633(6) Uani 1 1 d .
N2 N 0.29914(14) 0.17677(19) 0.43430(11) 0.0585(5) Uani 1 1 d .
N3 N 0.19322(13) 0.12642(18) 0.44716(10) 0.0522(5) Uani 1 1 d .
N4 N 0.37389(15) 0.0163(2) 0.54628(11) 0.0554(5) Uani 1 1 d .
H4 H 0.398(2) 0.087(3) 0.5158(13) 0.101(10) Uiso 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'
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
F2 B1 F1 107.8(2)
F2 B1 N1 113.1(2)
F1 B1 N1 112.3(2)
F2 B1 N3 108.65(18)
F1 B1 N3 107.8(2)
N1 B1 N3 106.9(2)
N1 C1 C2 109.7(3)
N1 C1 H1 125.1
C2 C1 H1 125.1
C1 C2 C3 107.5(3)
C1 C2 H2 126.3
C3 C2 H2 126.3
C4 C3 C2 106.9(3)
C4 C3 H3 126.6
C2 C3 H3 126.6
N1 C4 C3 109.2(2)
N1 C4 C5 118.7(2)
C3 C4 C5 132.1(3)
N2 C5 C4 128.6(2)
N2 C5 H5 115.7
C4 C5 H5 115.7
N3 C6 C7 131.1(2)
N3 C6 H6 114.5
C7 C6 H6 114.5
N4 C7 C8 106.4(2)
N4 C7 C6 126.6(2)
C8 C7 C6 127.0(2)
C9 C8 C7 108.8(2)
C9 C8 H8 125.6
C7 C8 H8 125.6
C8 C9 C10 106.8(2)
C8 C9 H9 126.6
C10 C9 H9 126.6
N4 C10 C9 109.3(2)
N4 C10 H10 125.4
C9 C10 H10 125.4
C1 N1 C4 106.7(2)
C1 N1 B1 129.3(2)
C4 N1 B1 123.89(19)
C5 N2 N3 114.47(18)
C6 N3 N2 114.46(17)
C6 N3 B1 118.33(19)
N2 N3 B1 127.21(19)
C10 N4 C7 108.8(2)
C10 N4 H4 132.7(17)
C7 N4 H4 118.5(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 F2 1.381(3)
B1 F1 1.390(3)
B1 N1 1.508(3)
B1 N3 1.582(3)
C1 N1 1.370(3)
C1 C2 1.371(4)
C1 H1 0.9300
C2 C3 1.392(4)
C2 H2 0.9300
C3 C4 1.383(3)
C3 H3 0.9300
C4 N1 1.380(3)
C4 C5 1.416(3)
C5 N2 1.293(3)
C5 H5 0.9300
C6 N3 1.307(3)
C6 C7 1.397(3)
C6 H6 0.9300
C7 N4 1.380(3)
C7 C8 1.382(3)
C8 C9 1.372(3)
C8 H8 0.9300
C9 C10 1.373(3)
C9 H9 0.9300
C10 N4 1.342(3)
C10 H10 0.9300
N2 N3 1.409(2)
N4 H4 0.93(2)
