Bis(napthobipyrrolyl)methene derived Hexapyrrolic BODIPY as a Single Molecule Helicate with Near Infrared Emission
Sahoo, Sipra Sucharita; Panda, Pradeepta; Chemical Communications  (2023) –; doi:10.1039/D3CC02336B

data_7131839
_publ_section_title
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 Bis(napthobipyrrolyl)methene derived Hexapyrrolic BODIPY as a Single
 Molecule Helicate with Near Infrared Emission
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC02336B
_journal_year                    2023
_chemical_formula_moiety         'C61 H69 N6 O4, Cl, 1[CHCl3]'
_chemical_formula_sum            'C62 H70 Cl4 N6 O4'
_chemical_formula_weight         1105.095
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_Int_Tables_number      15
_audit_creation_date             2023-06-30
_audit_creation_method
;
Olex2 1.5-dev
(compiled 2023.04.26 svn.r751481ca for OlexSys, GUI svn.r6697)
;
_audit_update_record
;
2023-07-05 deposited with the CCDC.	2023-07-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 117.007(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.345(2)
_cell_length_b                   29.544(3)
_cell_length_c                   13.7892(17)
_cell_measurement_reflns_used    3556
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      18.2
_cell_measurement_theta_min      2.8
_cell_volume                     5932.6(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5-dev (Bourhis et al., 2015)'
_computing_structure_solution    'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.9852
_diffrn_measured_fraction_theta_max 0.9852
_diffrn_measurement_device_type
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       '\w and \f scan'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2902
_diffrn_reflns_av_unetI/netI     0.0973
_diffrn_reflns_Laue_measured_fraction_full 0.9852
_diffrn_reflns_Laue_measured_fraction_max 0.9852
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            44117
_diffrn_reflns_point_group_measured_fraction_full 0.9852
_diffrn_reflns_point_group_measured_fraction_max 0.9852
_diffrn_reflns_theta_full        20.9807
_diffrn_reflns_theta_max         20.98
_diffrn_reflns_theta_min         1.75
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  0.95
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_description       block
_exptl_crystal_F_000             2339.586
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.5278
_refine_diff_density_min         -0.5242
_refine_diff_density_rms         0.1042
_refine_ls_d_res_high            0.9925
_refine_ls_d_res_low             11.6168
_refine_ls_goodness_of_fit_ref   1.0520
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    72
_refine_ls_number_parameters     414
_refine_ls_number_reflns         3132
_refine_ls_number_restraints     237
_refine_ls_restrained_S_all      1.0089
_refine_ls_R_factor_all          0.1304
_refine_ls_R_factor_gt           0.0763
_refine_ls_shift/su_max          -0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0960P)^2^+8.1840P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.1985
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -16
_reflns_limit_k_max              29
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                1902
_reflns_number_total             3132
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            d3cc02336b2.cif
_cod_data_source_block           PKPHCl
_cod_original_cell_volume        5932.6(13)
_cod_database_code               7131839
_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. Shared sites
{C16, C16'}
3. Restrained distances
 N3-H3 = N2-H2 = N1-H1
 0.9 with sigma of 0.03
 C3-C5 = C3'-C5' = C5-C6 = C5-C7 = C5'-C6' = C5'-C7'
 1.53 with sigma of 0.03
 C6-C7 = C6'-C7'
 2.49 with sigma of 0.03
 C16-C19 = C19-C20 = C19-C21 = C16'-C19' = C19'-C20' = C19'-C21'
 1.52 with sigma of 0.03
 C20-C21 = C20'-C21'
 2.49 with sigma of 0.02
 C2-C3 \\sim C4-C3 \\sim C2-C3' \\sim C4-C3'
 with sigma of 0.02
 C15-C16 \\sim C17-C16 \\sim C15-C16' \\sim C17-C16'
 with sigma of 0.03
4. Uiso/Uaniso restraints and constraints
N2 \\sim H2: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 2A
N3 \\sim H3: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 2A
N1 \\sim H1: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 2A
C3 \\sim C5 \\sim C6 \\sim C7 \\sim C3' \\sim C5' \\sim C6' \\sim C7': within
3A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 3A
C16 \\sim C19 \\sim C20 \\sim C21 \\sim C16' \\sim C19' \\sim C20' \\sim C21':
within 3A with sigma of 0.02 and sigma for terminal atoms of 0.04 within 3A
Uanis(C26) \\sim Ueq, Uanis(C7') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C16) = Uanis(C16')
5. Others
 Sof(C3')=Sof(C5')=Sof(H5')=Sof(C6')=Sof(H6'a)=Sof(H6'b)=Sof(H6'c)=Sof(C7')=
 Sof(H7'a)=Sof(H7'b)=Sof(H7'c)=1-FVAR(1)
 Sof(C3)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6a)=Sof(H6b)=Sof(H6c)=Sof(C7)=Sof(H7a)=
 Sof(H7b)=Sof(H7c)=FVAR(1)
 Sof(C16')=Sof(C19')=Sof(H19')=Sof(C20')=Sof(H20d)=Sof(H20e)=Sof(H20f)=
 Sof(C21')=Sof(H21d)=Sof(H21e)=Sof(H21f)=1-FVAR(2)
 Sof(C16)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20a)=Sof(H20b)=Sof(H20c)=Sof(C21)=
 Sof(H21a)=Sof(H21b)=Sof(H21c)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C5(H5), C5'(H5'), C19(H19), C19'(H19')
6.b Secondary CH2 refined with riding coordinates:
 C22(H22a,H22b), C31(H31a,H31b)
6.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C10(H10), C11(H11), C12(H12), C13(H13)
6.d Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c), C7(H7a,H7b,H7c), C6'(H6'a,H6'b,H6'c), C7'(H7'a,H7'b,H7'c),
 C20(H20a,H20b,H20c), C21(H21a,H21b,H21c), C20'(H20d,H20e,H20f), C21'(H21d,H21e,
 H21f), C27(H27a,H27b,H27c), C28(H28a,H28b,H28c), C32(H32a,H32b,H32c)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 250 electrons were 
found in a volume of 1014\%A^3^ in 1 void per unit cell. 
This is consistent with the presence of 1[CHCl3] per Formula Unit 
which account for 232 electrons per unit cell.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'