#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/87/7058721.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_7058721
loop_
_publ_author_name
'Hanson, Tanner B.'
'Chudomelka, Drayko D.'
'Heiden, Zachariah M.'
_publ_section_title
;
 Synthesis and characterization of hydrazine-appended BODIPY dyes and the
 related aminomethyl complexes
;
_journal_issue                   33
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              13103
_journal_paper_doi               10.1039/C9NJ02859E
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C9 H9 B F2 N4'
_chemical_formula_sum            'C9 H9 B F2 N4'
_chemical_formula_weight         222.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-05-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_audit_update_record
;
2019-07-25 deposited with the CCDC.    2019-07-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.876(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2353(4)
_cell_length_b                   13.4196(9)
_cell_length_c                   11.5682(7)
_cell_measurement_reflns_used    5567
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      3.04
_cell_volume                     953.63(11)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.9995
_diffrn_measured_fraction_theta_max 0.9990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15161
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         3.04
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0431 before and 0.0405 after correction.
The Ratio of minimum to maximum transmission is 0.9391.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.5462
_exptl_crystal_description       plate
_exptl_crystal_F_000             456.2504
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.3144
_refine_diff_density_min         -0.2499
_refine_diff_density_rms         0.0565
_refine_ls_d_res_high            0.7987
_refine_ls_d_res_low             6.7098
_refine_ls_goodness_of_fit_ref   1.0563
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     149
_refine_ls_number_reflns         1966
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0563
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0370P)²+0.4760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0776
_refine_ls_wR_factor_ref         0.0825
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1688
_reflns_number_total             1966
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c9nj02859e2.cif
_cod_data_source_block           WSU_ZH37
_cod_depositor_comments
'Adding full bibliography for 7058720--7058721.cif.'
_cod_database_code               7058721
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Rotating group:
 N4(H4a)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), N3(H3a), C7(H7), C8(H8), C9(H9)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-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_refinement_flags_posn
F1 F 0.79876(13) 0.73098(6) 0.29802(7) 0.0202(2) Uani 1.000000 .
C1 C 0.6632(2) 0.65424(10) 0.04132(12) 0.0179(3) Uani 1.000000 .
H1 H 0.7785(2) 0.61014(10) 0.06174(12) 0.0215(4) Uiso 1.000000 R
N1 N 0.64494(18) 0.74338(8) 0.09252(9) 0.0144(2) Uani 1.000000 .
B1 B 0.8082(2) 0.78535(11) 0.19641(13) 0.0155(3) Uani 1.000000 .
F2 F 1.01961(13) 0.77852(6) 0.17264(7) 0.0222(2) Uani 1.000000 .
N2 N 0.74432(17) 0.89438(8) 0.21137(9) 0.0145(2) Uani 1.000000 .
C2 C 0.4853(2) 0.63790(10) -0.04603(12) 0.0186(3) Uani 1.000000 .
H2 H 0.4607(2) 0.58206(10) -0.09409(12) 0.0224(4) Uiso 1.000000 R
C3 C 0.3507(2) 0.72030(10) -0.04848(12) 0.0167(3) Uani 1.000000 .
H3 H 0.2188(2) 0.72999(10) -0.09849(12) 0.0200(3) Uiso 1.000000 R
N3 N 0.21402(17) 0.93019(8) 0.03337(10) 0.0150(2) Uani 1.000000 .
H3a H 0.20118(17) 0.99011(8) 0.05767(10) 0.0180(3) Uiso 1.000000 R
N4 N 0.03760(18) 0.89224(9) -0.04690(10) 0.0172(3) Uani 1.000000 .
H4a H -0.00074(18) 0.83551(9) -0.02249(10) 0.0207(3) Uiso 1.000000 GR
C4 C 0.4504(2) 0.78663(10) 0.03865(11) 0.0135(3) Uani 1.000000 .
C5 C 0.3970(2) 0.88342(9) 0.07523(11) 0.0129(3) Uani 1.000000 .
C6 C 0.5492(2) 0.93729(9) 0.16122(11) 0.0132(3) Uani 1.000000 .
C7 C 0.5404(2) 1.03343(10) 0.20479(11) 0.0157(3) Uani 1.000000 .
H7 H 0.4272(2) 1.07880(10) 0.18537(11) 0.0188(3) Uiso 1.000000 R
C8 C 0.7347(2) 1.04897(10) 0.28355(12) 0.0184(3) Uani 1.000000 .
H8 H 0.7751(2) 1.10667(10) 0.32629(12) 0.0220(4) Uiso 1.000000 R
C9 C 0.8547(2) 0.96238(10) 0.28570(12) 0.0185(3) Uani 1.000000 .
H9 H 0.9909(2) 0.95214(10) 0.33129(12) 0.0222(4) Uiso 1.000000 R
H4b H 0.081(3) 0.8816(14) -0.1177(17) 0.033(5) Uiso 1.000000 .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
B 0.00141 0.00067 2.05450 1.33260 1.09790 0.70680 23.21850 1.02100 60.34980
0.14030 -0.193200007081
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 H1 124.94(8)
C2 C1 H1 124.94(8)
C2 C1 N1 110.12(12)
B1 N1 C1 124.91(11)
C4 N1 C1 107.82(11)
C4 N1 B1 127.20(11)
N1 B1 F1 110.39(11)
F2 B1 F1 108.06(11)
F2 B1 N1 110.00(11)
N2 B1 F1 110.80(11)
N2 B1 N1 106.67(10)
N2 B1 F2 110.94(11)
C6 N2 B1 125.28(11)
C9 N2 B1 126.83(11)
C9 N2 C6 107.47(11)
H2 C2 C1 126.41(8)
C3 C2 C1 107.17(12)
C3 C2 H2 126.41(8)
H3 C3 C2 126.31(8)
C4 C3 C2 107.38(12)
C4 C3 H3 126.31(8)
N4 N3 H3a 116.61(6)
C5 N3 H3a 116.61(7)
C5 N3 N4 126.78(11)
H4a N4 N3 109.5
H4b N4 N3 109.3(11)
H4b N4 H4a 107.2(11)
C3 C4 N1 107.51(11)
C5 C4 N1 118.54(11)
C5 C4 C3 133.90(12)
C4 C5 N3 123.82(12)
C6 C5 N3 116.04(11)
C6 C5 C4 120.13(11)
C5 C6 N2 120.51(11)
C7 C6 N2 108.75(11)
C7 C6 C5 130.71(12)
H7 C7 C6 126.55(8)
C8 C7 C6 106.90(12)
C8 C7 H7 126.55(8)
H8 C8 C7 126.51(8)
C9 C8 C7 106.99(12)
C9 C8 H8 126.51(8)
C8 C9 N2 109.89(12)
H9 C9 N2 125.06(7)
H9 C9 C8 125.06(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
F1 B1 1.3932(17)
C1 H1 0.9300
C1 N1 1.3482(17)
C1 C2 1.384(2)
N1 B1 1.5422(18)
N1 C4 1.3919(17)
B1 F2 1.3950(17)
B1 N2 1.5339(18)
N2 C6 1.3808(16)
N2 C9 1.3575(17)
C2 H2 0.9300
C2 C3 1.3853(19)
C3 H3 0.9300
C3 C4 1.4069(18)
N3 H3a 0.8600
N3 N4 1.4076(15)
N3 C5 1.3195(17)
N4 H4a 0.8600
N4 H4b 0.915(19)
C4 C5 1.4231(18)
C5 C6 1.4450(18)
C6 C7 1.3896(18)
C7 H7 0.9300
C7 C8 1.4008(19)
C8 H8 0.9300
C8 C9 1.380(2)
C9 H9 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168349433
