Extension of nature's NIR-I chromophore into the NIR-II region.
Siwawannapong, Kittipan; Diers, James R.; Magdaong, Nikki Cecil M.; Nalaoh, Phattananawee; Kirmaier, Christine; Lindsey, Jonathan S.; Holten, Dewey; Bocian, David F.; Physical chemistry chemical physics : PCCP 26 (2024) 14228–14243; doi:10.1039/d4cp00779d

data_7248577
_publ_section_title
;
 Extension of nature's NIR-I chromophore into the NIR-II region.
;
_journal_issue                   19
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              14228
_journal_page_last               14243
_journal_paper_doi               10.1039/d4cp00779d
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C27 H29 Br N2 O4'
_chemical_formula_sum            'C27 H29 Br N2 O4'
_chemical_formula_weight         525.43
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-12-08
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-23 deposited with the CCDC.	2024-04-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.0750(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.7636(4)
_cell_length_b                   11.7049(3)
_cell_length_c                   15.5223(5)
_cell_measurement_reflns_used    9449
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.121
_cell_measurement_theta_min      2.373
_cell_volume                     2467.75(12)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0552
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            37538
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.128
_diffrn_reflns_theta_min         2.297
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.702
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.5247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1440 before and 0.0741 after correction.
The Ratio of minimum to maximum transmission is 0.7038.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.723
_exptl_crystal_size_mid          0.575
_exptl_crystal_size_min          0.334
_refine_diff_density_max         0.368
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         5441
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.191
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0349
_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^)+(0.0084P)^2^+2.6272P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0820
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5020
_reflns_number_total             5441
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cp00779d2.cif
_cod_data_source_block           mo_ncsu_pn66_chcl3cyhx_0m_a
_cod_depositor_comments
'Adding full bibliography for 7248575--7248577.cif.'
_cod_original_cell_volume        2467.74(12)
_cod_database_code               7248577
_shelx_shelxl_version_number     2019/1
_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
 Br1-C8 \\sim Br1A-C8A
 with sigma of 0.02
 C1-C3 \\sim C1A-C3A
 with sigma of 0.02
 C1-C10 \\sim C1A-C10A
 with sigma of 0.02
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C2-C7 \\sim C2A-C7A
 with sigma of 0.02
 C2-C8 \\sim C2A-C8A
 with sigma of 0.02
 C3-C4 \\sim C3A-C4A
 with sigma of 0.02
 C4-C5 \\sim C4A-C5A
 with sigma of 0.02
 C5-C6 \\sim C5A-C6A
 with sigma of 0.02
 C6-C7 \\sim C6A-C7A
 with sigma of 0.02
 C8-C9 \\sim C8A-C9A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
 C9-C11 \\sim C9A-C11
 with sigma of 0.02
 Br1-C2 \\sim Br1A-C2A
 with sigma of 0.04
 Br1-C9 \\sim Br1A-C9A
 with sigma of 0.04
 C1-C2 \\sim C1A-C2A
 with sigma of 0.04
 C1-C4 \\sim C1A-C4A
 with sigma of 0.04
 C1-C9 \\sim C1A-C9A
 with sigma of 0.04
 C2-C4 \\sim C2A-C4A
 with sigma of 0.04
 C2-C6 \\sim C2A-C6A
 with sigma of 0.04
 C2-C9 \\sim C2A-C9A
 with sigma of 0.04
 C3-C5 \\sim C3A-C5A
 with sigma of 0.04
 C3-C7 \\sim C3A-C7A
 with sigma of 0.04
 C3-C8 \\sim C3A-C8A
 with sigma of 0.04
 C3-C10 \\sim C3A-C10A
 with sigma of 0.04
 C4-C6 \\sim C4A-C6A
 with sigma of 0.04
 C5-C7 \\sim C5A-C7A
 with sigma of 0.04
 C7-C8 \\sim C7A-C8A
 with sigma of 0.04
 C8-C10 \\sim C8A-C10A
 with sigma of 0.04
 C8-C11 \\sim C8A-C11
 with sigma of 0.04
 C10-C11 \\sim C10A-C11
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C2A) = Uanis(C3A)
Uanis(C5) = Uanis(C5A)
Uanis(C6) = Uanis(C4A)
Uanis(C7) = Uanis(C10)
Uanis(C9A) = Uanis(C2A)
Uanis(C1) = Uanis(C10A)
Uanis(C5) = Uanis(C6A)
4. Others
 Sof(C10A)=Sof(H10A)=Sof(C7A)=Sof(H7A)=Sof(C5A)=Sof(H5A)=Sof(C3A)=Sof(C8A)=
 Sof(C2A)=Sof(C6A)=Sof(H6A)=Sof(C9A)=Sof(C4A)=Sof(H4A)=Sof(C1A)=Sof(H1AA)=
 Sof(Br1A)=1-FVAR(1)
 Sof(Br1)=Sof(C1)=Sof(H1A)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=
 Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(C9)=Sof(C10)=Sof(H10)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C25(H25)
5.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C21(H21A,H21B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C14(H14), C18(H18),
 C10A(H10A), C7A(H7A), C5A(H5A), C6A(H6A), C4A(H4A), C1A(H1AA)
5.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C)
;
_shelx_res_checksum              60630
_olex2_submission_special_instructions 'No special instructions were received'