Synthesis and characterization of hydrazine-appended BODIPY dyes and the related aminomethyl complexes
Hanson, Tanner B.; Chudomelka, Drayko D.; Heiden, Zachariah M.; New Journal of Chemistry 43 (2019) 13103–; doi:10.1039/C9NJ02859E

data_7058721
_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       '\f and \w 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 \l/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/[\s^2^(Fo^2^)+(0.0370P)^2^+0.4760P] where P=(Fo^2^+2Fc^2^)/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'