Managing nucleophilic addition reactions to tune the physical properties of 2-substituted pentamethylBODIPY derivatives
Sritharan, S. R.; Hussein, B. A.; Machin, D. D.; El-Aooiti, M. A.; Adjei, J. A.; Singh, J. K.; Pau, J. T. H.; Dhindsa, J. S.; Lough, A. J.; Koivisto, B. D.; RSC Adv. 7 (2017) 8922–; doi:10.1039/C6RA28114A

data_7227556
_publ_section_title
;
 Managing nucleophilic addition reactions to tune the physical properties
 of 2-substituted pentamethylBODIPY derivatives
;
_journal_issue                   15
_journal_name_full               'RSC Adv.'
_journal_page_first              8922
_journal_paper_doi               10.1039/C6RA28114A
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C19 H22 B F2 N3 O2'
_chemical_formula_sum            'C19 H22 B F2 N3 O2'
_chemical_formula_weight         373.20
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-12-12 deposited with the CCDC.
2017-01-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.7917(19)
_cell_length_b                   11.2285(10)
_cell_length_c                   7.3897(6)
_cell_measurement_reflns_used    2083
_cell_measurement_temperature    147(2)
_cell_measurement_theta_max      21.90
_cell_measurement_theta_min      3.30
_cell_volume                     1808.2(3)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      147(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0956
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11348
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         2.040
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6423
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
; 
 Flack x determined using 855 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4098
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0474P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.1116
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                2437
_reflns_number_total             4098
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra28114a2.cif
_cod_data_source_block           d1471_a
_cod_database_code               7227556
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.993
_shelxl_version_number           2013-4
_shelx_res_checksum              42838