#------------------------------------------------------------------------------
#$Date: 2016-11-06 04:04:17 +0200 (Sun, 06 Nov 2016) $
#$Revision: 187969 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/43/1544338.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_1544338
loop_
_publ_author_name
'Li, Jin'
'Zhang, Qian'
'Yin, Jian'
'Yu, Changjiang'
'Cheng, Kai'
'Wei, Yun'
'Hao, Erhong'
'Jiao, Lijuan'
_publ_section_title
;
 Metal-Free and Versatile Synthetic Routes to Natural and Synthetic
 Prodiginines from Boron Dipyrrin.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5696
_journal_page_last               5699
_journal_paper_doi               10.1021/acs.orglett.6b02924
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C11 H9 B Br2 F2 N2 O2'
_chemical_formula_weight         409.83
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 100.474(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.1123(11)
_cell_length_b                   13.579(2)
_cell_length_c                   13.939(2)
_cell_measurement_reflns_used    4598
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.33
_cell_measurement_theta_min      2.97
_cell_volume                     1323.8(3)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0215
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9292
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.11
_exptl_absorpt_coefficient_mu    6.148
_exptl_absorpt_correction_T_max  0.5512
_exptl_absorpt_correction_T_min  0.5021
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.056
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         2.109
_refine_diff_density_min         -1.131
_refine_diff_density_rms         0.340
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0992
_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)+(0.3500P)²+0.1018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3571
_refine_ls_wR_factor_ref         0.3795
_reflns_number_gt                1972
_reflns_number_total             2339
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol6b02924_si_003.cif
_cod_data_source_block           120703b_0m
_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.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 1544337--1544338.cif.
;
_cod_original_cell_volume        1323.8(4)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               1544338
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
B1 B 0.2789(11) 0.3884(6) 0.6186(6) 0.0206(16) Uani 1 1 d .
Br1 Br 0.1004(2) 0.18080(9) 0.52245(9) 0.0649(7) Uani 1 1 d .
Br2 Br 0.46602(18) 0.48133(9) 0.83075(8) 0.0602(7) Uani 1 1 d .
C1 C 0.4065(10) 0.5472(5) 0.7157(5) 0.0229(15) Uani 1 1 d .
C2 C 0.4340(11) 0.6469(5) 0.7016(5) 0.0243(16) Uani 1 1 d .
H2 H 0.4793 0.6940 0.7487 0.029 Uiso 1 1 calc R
C3 C 0.3789(10) 0.6611(5) 0.6015(6) 0.0226(15) Uani 1 1 d .
C4 C 0.3168(10) 0.5697(5) 0.5585(5) 0.0216(15) Uani 1 1 d .
C5 C 0.2500(10) 0.5452(5) 0.4627(5) 0.0209(14) Uani 1 1 d .
H5 H 0.2416 0.5934 0.4148 0.025 Uiso 1 1 calc R
C6 C 0.1949(9) 0.4491(5) 0.4365(5) 0.0182(14) Uani 1 1 d .
C7 C 0.1265(10) 0.4066(5) 0.3443(5) 0.0211(15) Uani 1 1 d .
C8 C 0.0811(11) 0.3080(6) 0.3578(6) 0.0262(16) Uani 1 1 d .
H8 H 0.0301 0.2623 0.3105 0.031 Uiso 1 1 calc R
C9 C 0.1296(10) 0.2936(5) 0.4583(6) 0.0249(16) Uani 1 1 d .
C10 C 0.4450(17) 0.8310(5) 0.6018(8) 0.043(2) Uani 1 1 d .
H10A H 0.3525 0.8519 0.6398 0.065 Uiso 1 1 calc R
H10B H 0.4621 0.8820 0.5564 0.065 Uiso 1 1 calc R
H10C H 0.5646 0.8181 0.6442 0.065 Uiso 1 1 calc R
C11 C 0.0520(15) 0.4070(7) 0.1741(6) 0.041(2) Uani 1 1 d .
H11A H 0.1445 0.3575 0.1665 0.062 Uiso 1 1 calc R
H11B H 0.0400 0.4527 0.1208 0.062 Uiso 1 1 calc R
H11C H -0.0694 0.3764 0.1748 0.062 Uiso 1 1 calc R
F1 F 0.4367(7) 0.3295(3) 0.6468(4) 0.0327(12) Uani 1 1 d .
F2 F 0.1361(7) 0.3652(3) 0.6713(3) 0.0328(12) Uani 1 1 d .
N1 N 0.3360(9) 0.4985(4) 0.6325(4) 0.0190(13) Uani 1 1 d .
N2 N 0.1975(9) 0.3764(4) 0.5080(4) 0.0205(13) Uani 1 1 d .
O1 O 0.3784(9) 0.7422(4) 0.5488(4) 0.0346(14) Uani 1 1 d .
O2 O 0.1122(9) 0.4575(4) 0.2624(4) 0.0309(13) 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'
Br Br -0.2901 2.4595 '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
F1 B1 F2 110.7(6)
F1 B1 N1 110.1(6)
F2 B1 N1 110.6(6)
F1 B1 N2 111.1(6)
F2 B1 N2 108.8(6)
N1 B1 N2 105.4(5)
N1 C1 C2 113.3(6)
N1 C1 Br2 120.5(5)
C2 C1 Br2 126.1(6)
C1 C2 C3 104.8(6)
C1 C2 H2 127.6
C3 C2 H2 127.6
O1 C3 C2 130.0(7)
O1 C3 C4 121.7(7)
C2 C3 C4 108.3(6)
C5 C4 N1 121.2(6)
C5 C4 C3 130.6(7)
N1 C4 C3 108.2(6)
C4 C5 C6 120.9(6)
C4 C5 H5 119.5
C6 C5 H5 119.5
C5 C6 N2 120.5(6)
C5 C6 C7 131.0(6)
N2 C6 C7 108.5(6)
O2 C7 C8 129.3(7)
O2 C7 C6 122.1(6)
C8 C7 C6 108.6(6)
C9 C8 C7 104.4(6)
C9 C8 H8 127.8
C7 C8 H8 127.8
N2 C9 C8 113.3(6)
N2 C9 Br1 120.7(5)
C8 C9 Br1 125.9(6)
O1 C10 H10A 109.5
O1 C10 H10B 109.5
H10A C10 H10B 109.5
O1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
O2 C11 H11A 109.5
O2 C11 H11B 109.5
H11A C11 H11B 109.5
O2 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C1 N1 C4 105.4(6)
C1 N1 B1 128.8(6)
C4 N1 B1 125.8(6)
C9 N2 C6 105.2(6)
C9 N2 B1 128.7(6)
C6 N2 B1 125.9(6)
C3 O1 C10 116.2(7)
C7 O2 C11 117.7(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 F1 1.376(10)
B1 F2 1.393(9)
B1 N1 1.553(9)
B1 N2 1.554(9)
Br1 C9 1.805(7)
Br2 C1 1.818(7)
C1 N1 1.350(9)
C1 C2 1.388(10)
C2 C3 1.393(11)
C2 H2 0.9300
C3 O1 1.324(10)
C3 C4 1.414(10)
C4 C5 1.373(10)
C4 N1 1.402(9)
C5 C6 1.391(10)
C5 H5 0.9300
C6 N2 1.401(9)
C6 C7 1.413(10)
C7 O2 1.322(9)
C7 C8 1.399(10)
C8 C9 1.393(11)
C8 H8 0.9300
C9 N2 1.362(9)
C10 O1 1.449(10)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 O2 1.406(10)
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
