#------------------------------------------------------------------------------
#$Date: 2021-04-16 10:46:56 +0200 (vie 16 de abr de 2021) $
#$Revision: 264242 $
#$URL: svn://www.crystallography.net/cod/cif/4/12/16/4121654.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_4121654
loop_
_publ_author_name
'Tamgho, Ingrid-Suzy'
'Hasheminasab, Abed'
'Engle, James T.'
'Nemykin, Victor N.'
'Ziegler, Christopher J.'
_publ_section_title
;
 A New Highly Fluorescent and Symmetric Pyrrole-BF2 Chromophore: BOPHY.
;
_journal_issue                   15
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5623
_journal_paper_doi               10.1021/ja502477a
_journal_volume                  136
_journal_year                    2014
_chemical_formula_sum            'C10 H8 B2 F4 N4'
_chemical_formula_weight         281.82
_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                 105.850(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.1963(16)
_cell_length_b                   6.6666(12)
_cell_length_c                   7.0140(11)
_cell_measurement_reflns_used    975
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      62.67
_cell_measurement_theta_min      6.56
_cell_volume                     548.61(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.933
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            1345
_diffrn_reflns_theta_full        59.96
_diffrn_reflns_theta_max         59.96
_diffrn_reflns_theta_min         6.56
_exptl_absorpt_coefficient_mu    1.338
_exptl_absorpt_correction_T_max  0.8005
_exptl_absorpt_correction_T_min  0.5750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.276
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.276
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0508
_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)+(0.1164P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1556
_refine_ls_wR_factor_ref         0.1578
_reflns_number_gt                394
_reflns_number_total             418
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja502477a_si_002.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' 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 4121654--4121656.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

2021-04-11
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C5 H4 B F2 N2'
_cod_original_formula_weight         140.91
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               4121654
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
B1 B 0.3833(3) 0.0000 0.2225(5) 0.0271(11) Uani 1 2 d S
C1 C 0.1690(2) 0.0000 0.2253(5) 0.0233(9) Uani 1 2 d S
H1 H 0.1350 0.0000 0.0862 0.028 Uiso 1 2 calc SR
C2 C 0.1100(2) 0.0000 0.3689(4) 0.0250(10) Uani 1 2 d S
H2 H 0.0295 0.0000 0.3456 0.030 Uiso 1 2 calc SR
C3 C 0.1901(3) 0.0000 0.5530(5) 0.0233(9) Uani 1 2 d S
H3 H 0.1752 0.0000 0.6790 0.028 Uiso 1 2 calc SR
C4 C 0.2968(3) 0.0000 0.5161(4) 0.0203(9) Uani 1 2 d S
C5 C 0.5942(3) 0.0000 0.3512(4) 0.0211(9) Uani 1 2 d S
H5 H 0.5898 0.0000 0.2139 0.025 Uiso 1 2 calc SR
F1 F 0.38460(10) 0.1689(2) 0.10950(19) 0.0387(8) Uani 1 1 d .
N1 N 0.2830(2) 0.0000 0.3144(4) 0.0206(8) Uani 1 2 d S
N2 N 0.4978(2) 0.0000 0.3986(4) 0.0193(8) Uani 1 2 d S
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
B1 0.029(2) 0.027(3) 0.025(2) 0.000 0.0066(15) 0.000
C1 0.0271(16) 0.014(2) 0.0272(18) 0.000 0.0039(13) 0.000
C2 0.0246(17) 0.017(2) 0.0323(18) 0.000 0.0057(13) 0.000
C3 0.0281(17) 0.0146(19) 0.0297(17) 0.000 0.0120(12) 0.000
C4 0.0266(16) 0.009(2) 0.0256(17) 0.000 0.0078(12) 0.000
C5 0.0273(18) 0.013(2) 0.0242(16) 0.000 0.0090(13) 0.000
F1 0.0319(10) 0.0449(14) 0.0389(10) 0.0165(7) 0.0089(7) 0.0007(6)
N1 0.0255(15) 0.0134(17) 0.0234(15) 0.000 0.0076(11) 0.000
N2 0.0253(14) 0.0131(18) 0.0203(14) 0.000 0.0076(10) 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 '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
F1 B1 F1 109.4(3) 6 .
F1 B1 N1 112.19(17) 6 .
F1 B1 N1 112.19(17) . .
F1 B1 N2 107.51(17) 6 .
F1 B1 N2 107.51(17) . .
N1 B1 N2 107.8(3) . .
N1 C1 C2 109.5(3) . .
C1 C2 C3 107.5(3) . .
C2 C3 C4 106.4(3) . .
N1 C4 C3 109.4(3) . .
N1 C4 C5 120.7(3) . 5_656
C3 C4 C5 129.9(3) . 5_656
N2 C5 C4 126.0(3) . 5_656
C1 N1 C4 107.2(2) . .
C1 N1 B1 129.8(2) . .
C4 N1 B1 123.0(2) . .
C5 N2 N2 117.9(3) . 5_656
C5 N2 B1 117.5(3) . .
N2 N2 B1 124.6(3) 5_656 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F1 1.379(3) 6
B1 F1 1.379(3) .
B1 N1 1.531(4) .
B1 N2 1.592(4) .
C1 N1 1.359(4) .
C1 C2 1.389(4) .
C2 C3 1.391(4) .
C3 C4 1.394(4) .
C4 N1 1.378(4) .
C4 C5 1.399(5) 5_656
C5 N2 1.306(4) .
C5 C4 1.399(5) 5_656
N2 N2 1.408(5) 5_656
