Exploring the relationship between structure and activity in BODIPYs designed for antimicrobial phototherapy.
Hohlfeld, Benjamin F.; Gitter, Burkhard; Flanagan, Keith J.; Kingsbury, Christopher J.; Kulak, Nora; Senge, Mathias O.; Wiehe, Arno; Organic & biomolecular chemistry 18 (2020) 2416–2431; doi:10.1039/d0ob00188k

data_7157380
_publ_section_title
;
 Exploring the relationship between structure and activity in BODIPYs
 designed for antimicrobial phototherapy.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2416
_journal_page_last               2431
_journal_paper_doi               10.1039/d0ob00188k
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C18 H13 B F2 N4 O2'
_chemical_formula_sum            'C18 H13 B F2 N4 O2'
_chemical_formula_weight         366.13
_chemical_name_systematic
8-(4-N-Propargylamino-3-nitrophenyl)-bordipyrromethane
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-01-02 deposited with the CCDC.	2020-03-06 downloaded from the CCDC.
;
_cell_angle_alpha                110.5569(10)
_cell_angle_beta                 92.1349(11)
_cell_angle_gamma                98.3717(10)
_cell_formula_units_Z            2
_cell_length_a                   7.6304(2)
_cell_length_b                   9.5936(2)
_cell_length_c                   11.6142(3)
_cell_measurement_reflns_used    9381
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.81
_cell_measurement_theta_min      2.71
_cell_volume                     783.98(3)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'APEX 3 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Kappa diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0062
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            98665
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.900
_diffrn_reflns_theta_min         1.881
_diffrn_source                   'standard sealed X-ray tube'
_diffrn_source_type              'Siemens, KFF Mo 2K -90 C'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0449 before and 0.0420 after correction. The Ratio of minimum to maximum transmission is 0.9550. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.325
_exptl_crystal_size_min          0.234
_refine_diff_density_max         0.367
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0310
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+0.3296P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0824
_refine_ls_wR_factor_ref         0.0845
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3527
_reflns_number_total             3744
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00188k2.cif
_cod_data_source_block           kjf202
_cod_depositor_comments
'Adding full bibliography for 7157379--7157380.cif.'
_cod_database_code               7157380
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N2-H2
 0.86 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2A), C3(H3), C5(H5), C6(H6), C16(H16), C17(H17), C20(H20)
3.c :
 C23(H23)
;
_shelx_res_checksum              79663
_olex2_submission_special_instructions 'No special instructions were received'