#------------------------------------------------------------------------------
#$Date: 2017-07-12 04:24:22 +0200 (Wed 12 de Jul de 2017) $
#$Revision: 198658 $
#$URL: svn://www.crystallography.net/cod/cif/7/04/35/7043574.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_7043574
loop_
_publ_author_name
'Liu, Zhipeng'
'Liu, Yi'
'Duan, Jicheng'
'Qi, Fen'
'Tian, Dan'
'Wang, Xiaoqing'
'Huang, Wei'
_publ_section_title
;
 Optical Properties and Mechanofluorochromism of New BODIPY Dyes Based on
 Pyridine-Pyrimidine-Hybrid Structure
;
_journal_name_full               'Dalton Trans.'
_journal_paper_doi               10.1039/C7DT02259J
_journal_year                    2017
_chemical_formula_sum            'C11 H6 B Cl F2 N4'
_chemical_formula_weight         278.46
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2017-06-04 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.8410(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4083(9)
_cell_length_b                   5.5521(5)
_cell_length_c                   19.6438(17)
_cell_measurement_reflns_used    1805
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.19
_cell_measurement_theta_min      3.5515
_cell_volume                     1132.62(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(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  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5351
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.57
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  0.9394
_exptl_absorpt_correction_T_min  0.9266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2000
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0365
_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)+(0.0431P)²+0.1181P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0934
_reflns_number_gt                1430
_reflns_number_total             2000
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7dt02259j2.cif
_cod_data_source_block           150527h
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_sg_symbol_H-M      'P2(1)/n  '
_cod_database_code               7043574
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Cl1 Cl 0.43255(6) 1.26833(12) 0.04841(3) 0.0564(2) Uani 1 1 d .
F2 F 0.07709(12) 0.8210(3) 0.26183(5) 0.0527(4) Uani 1 1 d .
F1 F 0.11618(11) 0.4618(2) 0.21230(6) 0.0516(4) Uani 1 1 d .
N3 N 0.15452(14) 0.8234(3) 0.15018(8) 0.0317(4) Uani 1 1 d .
N2 N -0.07012(15) 0.6889(3) 0.17179(8) 0.0328(4) Uani 1 1 d .
C5 C -0.11786(18) 0.8660(4) 0.12925(9) 0.0320(5) Uani 1 1 d .
N4 N 0.36644(16) 0.8999(4) 0.11920(9) 0.0418(5) Uani 1 1 d .
C8 C 0.10350(19) 1.0056(4) 0.10929(9) 0.0306(5) Uani 1 1 d .
C11 C 0.31819(19) 1.0927(4) 0.08443(10) 0.0368(5) Uani 1 1 d .
C10 C 0.19211(19) 1.1510(4) 0.07626(10) 0.0355(5) Uani 1 1 d .
H10 H 0.1644 1.2823 0.0498 0.043 Uiso 1 1 calc R
C6 C -0.03027(18) 1.0318(4) 0.10191(10) 0.0319(5) Uani 1 1 d .
C4 C -0.1496(2) 0.5182(4) 0.19589(10) 0.0413(5) Uani 1 1 d .
H4 H -0.1144 0.3975 0.2242 0.050 Uiso 1 1 calc R
N1 N -0.12822(19) 1.3649(4) 0.02373(10) 0.0528(5) Uani 1 1 d .
C9 C 0.28223(19) 0.7772(4) 0.15087(10) 0.0380(5) Uani 1 1 d .
H9 H 0.3127 0.6454 0.1764 0.046 Uiso 1 1 calc R
C7 C -0.0830(2) 1.2192(4) 0.05855(10) 0.0368(5) Uani 1 1 d .
C1 C -0.25164(19) 0.8718(4) 0.11337(11) 0.0409(5) Uani 1 1 d .
H1 H -0.2870 0.9936 0.0855 0.049 Uiso 1 1 calc R
C3 C -0.2780(2) 0.5192(5) 0.17986(12) 0.0497(6) Uani 1 1 d .
H3 H -0.3306 0.4003 0.1964 0.060 Uiso 1 1 calc R
B1 B 0.0726(2) 0.6921(5) 0.20169(12) 0.0356(6) Uani 1 1 d .
C2 C -0.3296(2) 0.7019(5) 0.13814(11) 0.0485(6) Uani 1 1 d .
H2 H -0.4179 0.7077 0.1272 0.058 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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'
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
C9 N3 C8 119.06(17)
C9 N3 B1 119.19(17)
C8 N3 B1 121.32(16)
C5 N2 C4 120.66(17)
C5 N2 B1 121.44(17)
C4 N2 B1 117.48(17)
N2 C5 C1 117.85(19)
N2 C5 C6 118.74(17)
C1 C5 C6 123.39(19)
C9 N4 C11 114.72(18)
N3 C8 C6 118.68(18)
N3 C8 C10 116.68(17)
C6 C8 C10 124.63(18)
N4 C11 C10 125.2(2)
N4 C11 Cl1 114.35(15)
C10 C11 Cl1 120.47(17)
C11 C10 C8 117.82(19)
C8 C6 C5 123.46(18)
C8 C6 C7 118.52(18)
C5 C6 C7 117.65(17)
C3 C4 N2 121.9(2)
N4 C9 N3 126.1(2)
N1 C7 C6 178.1(2)
C2 C1 C5 120.8(2)
C4 C3 C2 118.5(2)
F1 B1 F2 111.27(18)
F1 B1 N3 110.38(18)
F2 B1 N3 109.07(18)
F1 B1 N2 110.15(18)
F2 B1 N2 107.75(18)
N3 B1 N2 108.14(15)
C1 C2 C3 120.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C11 1.727(2)
F2 B1 1.380(3)
F1 B1 1.368(3)
N3 C9 1.353(2)
N3 C8 1.376(2)
N3 B1 1.548(3)
N2 C5 1.363(3)
N2 C4 1.363(3)
N2 B1 1.561(3)
C5 C1 1.407(3)
C5 C6 1.426(3)
N4 C9 1.301(3)
N4 C11 1.348(3)
C8 C6 1.398(3)
C8 C10 1.415(3)
C11 C10 1.351(3)
C6 C7 1.430(3)
C4 C3 1.352(3)
N1 C7 1.140(3)
C1 C2 1.356(3)
C3 C2 1.389(3)
