Regioselective β-pyrrolic electrophilic substitution of hydrodipyrrin–dialkylboron complexes facilitates access to synthetic models for chlorophyll f
Liu, Mengran; Ptaszek, Marcin; Mass, Olga; Minkler, Daniel F.; Sommer, Roger D.; Bhaumik, Jayeeta; Lindsey, Jonathan S.; New Journal of Chemistry 38 (2014) 1717–; doi:10.1039/c3nj01508d

data_7054034
_publ_section_title
;
 Regioselective \b-pyrrolic electrophilic substitution of
 hydrodipyrrin--dialkylboron complexes facilitates access to synthetic
 models for chlorophyll f
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1717
_journal_paper_doi               10.1039/c3nj01508d
_journal_volume                  38
_journal_year                    2014
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H34 B Br1 N2 O'
_chemical_formula_sum            'C21 H34 B Br N2 O'
_chemical_formula_weight         421.24
_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'
_audit_creation_date             2013-11-25
_audit_creation_method
;
  Olex2 1.2
  (compiled 2013.03.22 svn.r2654, GUI svn.r4446)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.5208(3)
_cell_length_b                   16.5255(3)
_cell_length_c                   15.1765(3)
_cell_volume                     4394.20(14)
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_diffrn_measured_fraction_theta_full 0.9623
_diffrn_measured_fraction_theta_max 0.9623
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            77149
_diffrn_reflns_theta_full        27.3167
_diffrn_reflns_theta_max         27.32
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    1.882
_exptl_crystal_density_diffrn    1.2734
_exptl_crystal_F_000             1774.3418
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.09
_refine_diff_density_max         2.1896
_refine_diff_density_min         -0.5229
_refine_diff_density_rms         0.0966
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.038(8)
_refine_ls_d_res_high            0.7744
_refine_ls_d_res_low             12.0218
_refine_ls_goodness_of_fit_ref   1.0686
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    106
_refine_ls_number_parameters     499
_refine_ls_number_reflns         9523
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.0685
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0455
_refine_ls_shift/su_max          0.1049
_refine_ls_shift/su_mean         0.0035
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0440P)^2^+6.0120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1119
_reflns_Friedel_coverage         0.924
_reflns_limit_h_max              22
_reflns_limit_h_min              -22
_reflns_limit_k_max              21
_reflns_limit_k_min              -21
_reflns_limit_l_max              17
_reflns_limit_l_min              -19
_reflns_number_gt                8768
_reflns_number_total             9523
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            c3nj01508d2.cif
_cod_data_source_block           rds011
_cod_database_code               7054034
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C41-C40
 0.009 with sigma of 1.54
 C19-C20
 1.54 with sigma of 0.009
3. Others
 Sof(Br2)=1-Sof(Br2A)=1-Sof(Br2A)=Sof(H30)
 Sof(Br1)=1-Sof(Br1A)=1-Sof(Br1A)=Sof(H9)
4.a Ternary CH refined with riding coordinates:
 C4(H4), C25(H25)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C5(H5a,H5b), C13(H13a,H13b), C14(H14a,H14b), C15(H15a,H15b),
 C17(H17a,H17b), C18(H18a,H18b), C19(H19a,H19b), C23(H23a,H23b), C26(H26a,H26b),
  C34(H34a,H34b), C35(H35a,H35b), C36(H36a,H36b), C38(H38a,H38b), C39(H39a,
 H39b), C40(H40a,H40b)
4.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C21(H21), C29(H29), C30(H30), C42(H42)
4.d Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C12(H12a,H12b,H12c), C16(H16a,H16b,
 H16c), C20(H20a,H20b,H20c), C31(H31a,H31b,H31c), C32(H32a,H32b,H32c), C33(H33a,
 H33b,H33c), C37(H37a,H37b,H37c), C41(H41a,H41b,H41c)
;