Functionalization of 3,5,8-Trichlorinated BODIPY Dyes.
Wang, Haijun; Fronczek, Frank R.; Vicente, M Graça H; Smith, Kevin M.; The Journal of organic chemistry 79 (2014) 10342–; doi:10.1021/jo501969z

data_4030036
_publ_section_title
;
 Functionalization of 3,5,8-Trichlorinated BODIPY Dyes.
;
_journal_issue                   21
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10342
_journal_paper_doi               10.1021/jo501969z
_journal_volume                  79
_journal_year                    2014
_chemical_formula_moiety         'C23 H23 B Cl2 F2 N2 O4 S'
_chemical_formula_sum            'C23 H23 B Cl2 F2 N2 O4 S'
_chemical_formula_weight         543.20
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yc'
_symmetry_space_group_name_H-M   'P 1 c 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
_cell_angle_beta                 104.362(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.9869(9)
_cell_length_b                   9.9485(7)
_cell_length_c                   20.9771(15)
_cell_measurement_reflns_used    6528
_cell_measurement_temperature    100.0(5)
_cell_measurement_theta_max      60.94
_cell_measurement_theta_min      3.81
_cell_volume                     2423.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(5)
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'QUAZAR multilayer optics'
_diffrn_radiation_source         'I\mS microfocus'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_sigmaI/netI    0.0559
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14337
_diffrn_reflns_theta_full        61.38
_diffrn_reflns_theta_max         61.38
_diffrn_reflns_theta_min         3.81
_exptl_absorpt_coefficient_mu    3.653
_exptl_absorpt_correction_T_max  0.9305
_exptl_absorpt_correction_T_min  0.3451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.984
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 'Flack (1983) '
_refine_ls_abs_structure_Flack   0.49(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     654
_refine_ls_number_reflns         6294
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0640
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1067P)^2^+3.5575P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1704
_refine_ls_wR_factor_ref         0.1804
_reflns_number_gt                5424
_reflns_number_total             6294
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo501969z_si_002.cif
_cod_data_source_block           Compound11
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--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 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 4030032--4030045.cif.
;
_cod_original_sg_symbol_Hall     'P -2yc '
_cod_original_sg_symbol_H-M      'P c   '
_cod_database_code               4030036