BODIPY atropisomer interconversion, face discrimination, and superstructure appending.
Doulain, Pierre-Emmanuel; Goze, Christine; Bodio, Ewen; Richard, Philippe; Decréau, Richard A; Chemical communications (Cambridge, England) 52 (2016) 4474–4477; doi:10.1039/c5cc10526a

data_7118794
_publ_section_title
;
 BODIPY atropisomer interconversion, face discrimination, and
 superstructure appending.
;
_journal_issue                   24
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              4474
_journal_page_last               4477
_journal_paper_doi               10.1039/c5cc10526a
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         '2(C24 H21 B F2 N4 O), 1.5(C4 H8 O2)'
_chemical_formula_sum            'C54 H54 B2 F4 N8 O5'
_chemical_formula_weight         992.67
_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_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-12-17
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2015-12-17 deposited with the CCDC.
2016-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.671(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3756(19)
_cell_length_b                   14.865(2)
_cell_length_c                   24.544(3)
_cell_measurement_reflns_used    5428
_cell_measurement_temperature    115
_cell_measurement_theta_max      22.95
_cell_measurement_theta_min      2.29
_cell_volume                     4878.0(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      115
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean '512 x 512'
_diffrn_detector_type            APEX2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       '\f and \w scans''
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1119
_diffrn_reflns_av_unetI/netI     0.1139
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            55917
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.512
_diffrn_reflns_theta_min         2.665
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0707 before and 0.0613 after correction.
The Ratio of minimum to maximum transmission is 0.8991.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_description       needle
_exptl_crystal_F_000             2080
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     693
_refine_ls_number_reflns         11178
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.1503
_refine_ls_R_factor_gt           0.0533
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0539P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1349
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5522
_reflns_number_total             11178
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5cc10526a2.cif
_cod_data_source_block           pe18052014_0m_a
_cod_depositor_comments          'Adding full bibliography for 7118794.cif.'
_cod_original_cell_volume        4877.8(12)
_cod_database_code               7118794
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 C53, C54, C55, C56, O5, O6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: C53(0.5) H53A(0.5) H53B(0.5) H53C(0.5) C54(0.5) H54A(0.5)
 H54B(0.5) C55(0.5) C56(0.5) H56A(0.5) H56B(0.5) H56C(0.5) O5(0.5) O6(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C50(H50A,H50B), C54(H54A,H54B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C18(H18), C19(H19), C21(H21), C22(H22), N3(H3A), C25(H25), C26(H26),
 C27(H27), C31(H31), C32(H32), C33(H33), C35(H35), C36(H36), C37(H37), C38(H38),
  C42(H42), C43(H43), C45(H45), C46(H46), N7(H7A)
4.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C47(H47A,H47B,H47C), C48(H48A,H48B,
 H48C), C49(H49A,H49B,H49C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C56(H56A,
 H56B,H56C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'