Studying the reactivity of alkyl substituted BODIPYs: first enantioselective addition of BODIPY to MBH carbonates
Meazza, Marta; Cruz, Carlos M.; Ortuño, Ana M.; Cuerva, Juan M.; Crovetto, Luis; Rios, Ramon; Chemical Science 12 (2021) 4503–4508; doi:10.1039/D0SC06574A

data_1560298
_publ_section_title
;
 Studying the reactivity of alkyl substituted BODIPYs: first
 enantioselective addition of BODIPY to MBH carbonates
;
_journal_issue                   12
_journal_name_full               'Chemical Science'
_journal_page_first              4503
_journal_page_last               4508
_journal_paper_doi               10.1039/D0SC06574A
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C22 H21 B F2 N2 O2'
_chemical_formula_sum            'C22 H21 B F2 N2 O2'
_chemical_formula_weight         394.22
_chemical_name_systematic
'methyl 4-(5,5-difluoro-5H-4l4,5l4-dipyrrolo[1,2-c:2',1'-f][1,3,2]diazaborinin-10-yl)-2-methylene-3-phenylpentanoate'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-30
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-06-30 deposited with the CCDC.	2021-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6493(2)
_cell_length_b                   9.2440(2)
_cell_length_c                   18.0005(3)
_cell_measurement_reflns_used    12610
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.7850
_cell_measurement_theta_min      3.5330
_cell_volume                     2104.80(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9g (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -37.00  37.00   1.00   10.00    --  -19.00 -19.00  30.00   74
  2  \w    -93.00  10.00   1.00   10.00    --  -19.00 -38.00 -60.00  103
  3  \w    -35.00  11.00   1.00   10.00    --  -19.00  38.00   0.00   46
  4  \w     17.00  69.00   1.00   10.00    --  -19.00  38.00   0.00   52
  5  \w    -45.00   7.00   1.00   10.00    --  -19.00  38.00-180.00   52
  6  \w     10.00  49.00   1.00   10.00    --  -19.00  38.00-180.00   39
  7  \w    -42.00  69.00   1.00   10.00    --  -19.00  38.00 -90.00  111
  8  \w    -34.00   0.00   1.00   10.00    --  -19.00  38.00 -30.00   34
  9  \w    -92.00 -43.00   1.00   10.00    --  -19.00 -19.00  30.00   49
;
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RCD3): Kappa single'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0353772000
_diffrn_orient_matrix_UB_12      0.0310350000
_diffrn_orient_matrix_UB_13      0.0261044000
_diffrn_orient_matrix_UB_21      -0.0233466000
_diffrn_orient_matrix_UB_22      0.0688045000
_diffrn_orient_matrix_UB_23      -0.0059405000
_diffrn_orient_matrix_UB_31      -0.0366745000
_diffrn_orient_matrix_UB_32      -0.0137226000
_diffrn_orient_matrix_UB_33      0.0289461000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28599
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.735
_diffrn_reflns_theta_min         3.159
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.9g (Rigaku Oxford Diffraction, 2015) Empirical 
absorption correction using spherical harmonics, implemented in SCALE3 
ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description       irregular
_exptl_crystal_F_000             824
_exptl_crystal_preparation       'crystallization from chloroform'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Chloroform'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1897 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         6184
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0612
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0910P)^2^+0.1000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.1622
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.917
_reflns_number_gt                5151
_reflns_number_total             6184
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0sc06574a2.cif
_cod_data_source_block           2019-mm04
_cod_depositor_comments          'Adding full bibliography for 1560298.cif.'
_cod_database_code               1560298
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C22H21BF2N2O2
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.64
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C12(H12)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C1(H1), C5(H5), C2(H2), C6(H6), C17(H17), C21(H21), C18(H18),
 C20(H20), C19(H19)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C00L(H00A,H00B,H00C)
;
_shelx_res_checksum              6824
_shelx_hkl_checksum              65517
_olex2_date_sample_completion    2019-12-11
_olex2_date_sample_data_collection 2019-12-11
_olex2_date_sample_submission    2019-12-11
_olex2_submission_original_sample_id mm-8943-36
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.664
_oxdiff_exptl_absorpt_empirical_full_min 0.495