#------------------------------------------------------------------------------
#$Date: 2020-04-05 14:11:58 +0300 (Sun, 05 Apr 2020) $
#$Revision: 250366 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/73/7157380.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_7157380
loop_
_publ_author_name
'Hohlfeld, Benjamin F.'
'Gitter, Burkhard'
'Flanagan, Keith J.'
'Kingsbury, Christopher J.'
'Kulak, Nora'
'Senge, Mathias O.'
'Wiehe, Arno'
_publ_section_title
;
 Exploring the relationship between structure and activity in BODIPYs
 designed for antimicrobial phototherapy.
;
_journal_issue                   13
_journal_name_full               'Organic & 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       'ω and φ 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 λ/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/[σ²(Fo²)+(0.0416P)²+0.3296P] where P=(Fo²+2Fc²)/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 > 2σ(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_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F13 F 0.61422(8) -0.12396(7) 0.23400(6) 0.02057(14) Uani 1 1 d . . . . .
F14 F 0.91140(8) -0.11528(7) 0.22883(6) 0.01936(14) Uani 1 1 d . . . . .
O1 O 0.88704(10) 0.32689(8) 0.99366(7) 0.01839(16) Uani 1 1 d . . . . .
O2 O 0.78138(10) 0.52889(8) 1.09163(6) 0.01718(16) Uani 1 1 d . . . . .
N1 N 0.80708(10) 0.42981(9) 0.99398(7) 0.01261(16) Uani 1 1 d . . . . .
N2 N 0.60769(11) 0.66110(9) 0.97181(7) 0.01389(17) Uani 1 1 d D . . . .
H2 H 0.6590(19) 0.6713(17) 1.0428(10) 0.027(4) Uiso 1 1 d D . . . .
N10 N 0.78702(11) -0.06517(9) 0.42613(7) 0.01384(17) Uani 1 1 d . . . . .
N11 N 0.80459(11) 0.12039(9) 0.32302(7) 0.01403(17) Uani 1 1 d . . . . .
C1 C 0.71101(13) -0.02733(11) 0.62066(9) 0.01568(19) Uani 1 1 d . . . . .
H1 H 0.6748 0.0180 0.7008 0.019 Uiso 1 1 calc R . . . .
C2 C 0.74181(14) -0.17436(11) 0.56799(10) 0.0183(2) Uani 1 1 d . . . . .
H2A H 0.7344 -0.2477 0.6060 0.022 Uiso 1 1 calc R . . . .
C3 C 0.78603(14) -0.19410(11) 0.44762(9) 0.0173(2) Uani 1 1 d . . . . .
H3 H 0.8116 -0.2854 0.3898 0.021 Uiso 1 1 calc R . . . .
C5 C 0.85241(13) 0.18968(12) 0.24336(9) 0.0170(2) Uani 1 1 d . . . . .
H5 H 0.8741 0.1396 0.1601 0.020 Uiso 1 1 calc R . . . .
C6 C 0.86549(14) 0.34624(12) 0.30118(9) 0.0181(2) Uani 1 1 d . . . . .
H6 H 0.8973 0.4202 0.2652 0.022 Uiso 1 1 calc R . . . .
C7 C 0.82288(13) 0.37253(11) 0.42156(9) 0.01558(19) Uani 1 1 d . . . . .
H7 H 0.8269(18) 0.4696(16) 0.4859(13) 0.020(3) Uiso 1 1 d . . . . .
C8 C 0.74542(12) 0.19231(11) 0.53969(8) 0.01249(18) Uani 1 1 d . . . . .
C9 C 0.74352(12) 0.04294(11) 0.53289(9) 0.01333(18) Uani 1 1 d . . . . .
C12 C 0.78407(12) 0.23072(11) 0.43524(8) 0.01329(18) Uani 1 1 d . . . . .
C15 C 0.71144(12) 0.31074(10) 0.65378(8) 0.01274(18) Uani 1 1 d . . . . .
C16 C 0.61036(13) 0.42076(11) 0.64757(9) 0.01386(18) Uani 1 1 d . . . . .
H16 H 0.5627 0.4153 0.5691 0.017 Uiso 1 1 calc R . . . .
C17 C 0.57894(13) 0.53503(11) 0.75122(9) 0.01409(18) Uani 1 1 d . . . . .
H17 H 0.5124 0.6076 0.7423 0.017 Uiso 1 1 calc R . . . .
C18 C 0.64302(12) 0.54811(10) 0.87175(9) 0.01230(18) Uani 1 1 d . . . . .
C19 C 0.73959(12) 0.43380(10) 0.87667(8) 0.01202(18) Uani 1 1 d . . . . .
C20 C 0.77569(12) 0.32049(10) 0.77057(9) 0.01249(18) Uani 1 1 d . . . . .
H20 H 0.8451 0.2490 0.7782 0.015 Uiso 1 1 calc R . . . .
C21 C 0.53671(13) 0.79022(11) 0.96198(9) 0.01508(19) Uani 1 1 d . . . . .
H21A H 0.4935 0.8464 1.0417 0.018 Uiso 1 1 calc R . . . .
H21B H 0.4342 0.7536 0.8980 0.018 Uiso 1 1 calc R . . . .
C22 C 0.67223(14) 0.89267(11) 0.92961(9) 0.0164(2) Uani 1 1 d . . . . .
C23 C 0.78917(15) 0.97329(12) 0.90756(10) 0.0199(2) Uani 1 1 d . . . . .
H23 H 0.8826 1.0377 0.8900 0.024 Uiso 1 1 calc R . . . .
B4 B 0.78026(15) -0.05052(12) 0.29803(10) 0.0148(2) 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'
F F 0.0171 0.0103 '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'
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
_geom_angle_publ_flag
O1 N1 O2 121.78(8) . . ?
O1 N1 C19 118.89(8) . . ?
O2 N1 C19 119.33(8) . . ?
C18 N2 H2 117.4(10) . . ?
C18 N2 C21 122.22(8) . . ?
C21 N2 H2 117.5(10) . . ?
C3 N10 C9 107.94(8) . . ?
C3 N10 B4 125.79(8) . . ?
C9 N10 B4 123.93(8) . . ?
C5 N11 C12 108.12(8) . . ?
C5 N11 B4 126.99(8) . . ?
C12 N11 B4 124.87(8) . . ?
C2 C1 H1 126.3 . . ?
C2 C1 C9 107.38(9) . . ?
C9 C1 H1 126.3 . . ?
C1 C2 H2A 126.6 . . ?
C1 C2 C3 106.86(9) . . ?
C3 C2 H2A 126.6 . . ?
N10 C3 C2 110.17(9) . . ?
N10 C3 H3 124.9 . . ?
C2 C3 H3 124.9 . . ?
N11 C5 H5 124.9 . . ?
N11 C5 C6 110.13(9) . . ?
C6 C5 H5 124.9 . . ?
C5 C6 H6 126.7 . . ?
C7 C6 C5 106.68(9) . . ?
C7 C6 H6 126.7 . . ?
C6 C7 H7 126.5(8) . . ?
C6 C7 C12 107.54(9) . . ?
C12 C7 H7 125.9(8) . . ?
C9 C8 C12 119.33(8) . . ?
C9 C8 C15 121.55(8) . . ?
C12 C8 C15 119.11(8) . . ?
N10 C9 C1 107.60(8) . . ?
N10 C9 C8 120.43(8) . . ?
C8 C9 C1 131.91(9) . . ?
N11 C12 C7 107.53(8) . . ?
N11 C12 C8 120.95(9) . . ?
C7 C12 C8 131.32(9) . . ?
C16 C15 C8 120.16(8) . . ?
C20 C15 C8 122.57(8) . . ?
C20 C15 C16 117.27(8) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 C15 122.11(9) . . ?
C17 C16 H16 118.9 . . ?
C16 C17 H17 119.0 . . ?
C16 C17 C18 121.91(9) . . ?
C18 C17 H17 119.0 . . ?
N2 C18 C17 120.27(9) . . ?
N2 C18 C19 124.43(9) . . ?
C17 C18 C19 115.28(8) . . ?
C18 C19 N1 121.23(8) . . ?
C20 C19 N1 116.31(8) . . ?
C20 C19 C18 122.46(8) . . ?
C15 C20 C19 120.90(9) . . ?
C15 C20 H20 119.6 . . ?
C19 C20 H20 119.5 . . ?
N2 C21 H21A 109.3 . . ?
N2 C21 H21B 109.3 . . ?
N2 C21 C22 111.59(8) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C23 C22 C21 176.04(11) . . ?
C22 C23 H23 180.0 . . ?
F13 B4 N10 108.66(8) . . ?
F13 B4 N11 110.79(8) . . ?
F14 B4 F13 108.50(8) . . ?
F14 B4 N10 111.98(8) . . ?
F14 B4 N11 111.02(8) . . ?
N10 B4 N11 105.87(8) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F13 B4 1.3988(12) . ?
F14 B4 1.3869(12) . ?
O1 N1 1.2329(11) . ?
O2 N1 1.2419(11) . ?
N1 C19 1.4537(12) . ?
N2 H2 0.867(9) . ?
N2 C18 1.3498(12) . ?
N2 C21 1.4597(12) . ?
N10 C3 1.3441(13) . ?
N10 C9 1.3968(12) . ?
N10 B4 1.5425(13) . ?
N11 C5 1.3481(13) . ?
N11 C12 1.3922(12) . ?
N11 B4 1.5428(13) . ?
C1 H1 0.9500 . ?
C1 C2 1.3857(14) . ?
C1 C9 1.4170(13) . ?
C2 H2A 0.9500 . ?
C2 C3 1.4042(14) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C5 C6 1.3999(14) . ?
C6 H6 0.9500 . ?
C6 C7 1.3907(14) . ?
C7 H7 0.963(14) . ?
C7 C12 1.4148(13) . ?
C8 C9 1.4051(13) . ?
C8 C12 1.4154(13) . ?
C8 C15 1.4724(12) . ?
C15 C16 1.4144(13) . ?
C15 C20 1.3918(13) . ?
C16 H16 0.9500 . ?
C16 C17 1.3710(13) . ?
C17 H17 0.9500 . ?
C17 C18 1.4220(13) . ?
C18 C19 1.4230(13) . ?
C19 C20 1.3956(13) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.4728(14) . ?
C22 C23 1.1896(16) . ?
C23 H23 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2 F13 0.867(9) 2.468(14) 3.0127(10) 121.4(12) 1_566
N2 H2 O2 0.867(9) 1.984(13) 2.6256(11) 129.9(13) .
C20 H20 F14 0.95 2.40 3.3097(11) 161.3 2_756
C21 H21A F13 0.99 2.29 2.9835(11) 126.3 1_566
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C19 C18 178.62(8) . . . . ?
O1 N1 C19 C20 -1.69(13) . . . . ?
O2 N1 C19 C18 -0.69(13) . . . . ?
O2 N1 C19 C20 179.00(8) . . . . ?
N1 C19 C20 C15 177.60(8) . . . . ?
N2 C18 C19 N1 0.82(14) . . . . ?
N2 C18 C19 C20 -178.85(9) . . . . ?
N11 C5 C6 C7 -0.19(12) . . . . ?
C1 C2 C3 N10 1.29(12) . . . . ?
C2 C1 C9 N10 2.27(11) . . . . ?
C2 C1 C9 C8 -174.80(10) . . . . ?
C3 N10 C9 C1 -1.48(11) . . . . ?
C3 N10 C9 C8 175.99(9) . . . . ?
C3 N10 B4 F13 66.82(12) . . . . ?
C3 N10 B4 F14 -53.01(13) . . . . ?
C3 N10 B4 N11 -174.13(9) . . . . ?
C5 N11 C12 C7 -0.41(11) . . . . ?
C5 N11 C12 C8 -175.79(9) . . . . ?
C5 N11 B4 F13 -80.54(12) . . . . ?
C5 N11 B4 F14 40.09(13) . . . . ?
C5 N11 B4 N10 161.82(9) . . . . ?
C5 C6 C7 C12 -0.07(11) . . . . ?
C6 C7 C12 N11 0.29(11) . . . . ?
C6 C7 C12 C8 175.01(10) . . . . ?
C8 C15 C16 C17 -178.47(9) . . . . ?
C8 C15 C20 C19 -179.54(8) . . . . ?
C9 N10 C3 C2 0.14(11) . . . . ?
C9 N10 B4 F13 -93.70(10) . . . . ?
C9 N10 B4 F14 146.47(9) . . . . ?
C9 N10 B4 N11 25.35(12) . . . . ?
C9 C1 C2 C3 -2.16(11) . . . . ?
C9 C8 C12 N11 5.72(14) . . . . ?
C9 C8 C12 C7 -168.41(10) . . . . ?
C9 C8 C15 C16 -141.20(9) . . . . ?
C9 C8 C15 C20 38.94(13) . . . . ?
C12 N11 C5 C6 0.38(11) . . . . ?
C12 N11 B4 F13 101.05(10) . . . . ?
C12 N11 B4 F14 -138.32(9) . . . . ?
C12 N11 B4 N10 -16.59(12) . . . . ?
C12 C8 C9 N10 2.83(13) . . . . ?
C12 C8 C9 C1 179.59(10) . . . . ?
C12 C8 C15 C16 39.96(13) . . . . ?
C12 C8 C15 C20 -139.89(9) . . . . ?
C15 C8 C9 N10 -176.01(8) . . . . ?
C15 C8 C9 C1 0.75(16) . . . . ?
C15 C8 C12 N11 -175.42(8) . . . . ?
C15 C8 C12 C7 10.46(15) . . . . ?
C15 C16 C17 C18 -1.36(15) . . . . ?
C16 C15 C20 C19 0.60(14) . . . . ?
C16 C17 C18 N2 -179.20(9) . . . . ?
C16 C17 C18 C19 -0.65(14) . . . . ?
C17 C18 C19 N1 -177.66(8) . . . . ?
C17 C18 C19 C20 2.66(13) . . . . ?
C18 N2 C21 C22 -72.46(11) . . . . ?
C18 C19 C20 C15 -2.71(14) . . . . ?
C20 C15 C16 C17 1.39(14) . . . . ?
C21 N2 C18 C17 -12.82(14) . . . . ?
C21 N2 C18 C19 168.77(9) . . . . ?
B4 N10 C3 C2 -162.96(9) . . . . ?
B4 N10 C9 C1 162.00(9) . . . . ?
B4 N10 C9 C8 -20.53(13) . . . . ?
B4 N11 C5 C6 -178.25(9) . . . . ?
B4 N11 C12 C7 178.25(9) . . . . ?
B4 N11 C12 C8 2.88(14) . . . . ?
