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_7248576
_publ_section_title
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 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         'C19 H17 Br N2 O4'
_chemical_formula_sum            'C19 H17 Br N2 O4'
_chemical_formula_weight         417.25
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-18
_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                 93.804(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.445(3)
_cell_length_b                   12.529(3)
_cell_length_c                   11.461(2)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.41
_cell_volume                     1783.1(7)
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0535
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29690
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.386
_diffrn_reflns_theta_min         2.309
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.333
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1573 before and 0.0731 after correction.
The Ratio of minimum to maximum transmission is 0.7961.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_description       prism
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.602
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.066
_refine_diff_density_max         1.244
_refine_diff_density_min         -0.408
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3650
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0388P)^2^+2.8303P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0909
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3237
_reflns_number_total             3650
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cp00779d2.cif
_cod_data_source_block           pn60_a
_cod_depositor_comments
'Adding full bibliography for 7248575--7248577.cif.'
_cod_original_cell_volume        1783.1(6)
_cod_database_code               7248576
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_max   0.861
_shelx_estimated_absorpt_t_min   0.334
_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. Restrained distances
 O3-N3 \\sim O3A-N3
 with sigma of 0.02
 O5-N3 \\sim O5A-N3
 with sigma of 0.02
 Br1-C7 \\sim Br1-C7A
 with sigma of 0.02
 C1-C2 \\sim C1A-C2A
 with sigma of 0.02
 C1-C6 \\sim C1A-C6A
 with sigma of 0.02
 C1-C7 \\sim C1A-C7A
 with sigma of 0.02
 C2-C3 \\sim C2A-C3A
 with sigma of 0.02
 C2-C10 \\sim C2A-C10A
 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
 C7-C8 \\sim C7A-C8
 with sigma of 0.02
 C8-C9 \\sim C8-C9A
 with sigma of 0.02
 C9-C10 \\sim C9A-C10A
 with sigma of 0.02
 Br1-C1 \\sim Br1-C1A
 with sigma of 0.04
 C1-C3 \\sim C1A-C3A
 with sigma of 0.04
 C1-C5 \\sim C1A-C5A
 with sigma of 0.04
 C1-C8 \\sim C1A-C8
 with sigma of 0.04
 C1-C10 \\sim C1A-C10A
 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-C7 \\sim C2A-C7A
 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-C10 \\sim C3A-C10A
 with sigma of 0.04
 C4-C6 \\sim C4A-C6A
 with sigma of 0.04
 C6-C7 \\sim C6A-C7A
 with sigma of 0.04
 C8-C10 \\sim C8-C10A
 with sigma of 0.04
 C7-C8 \\sim C7-C8A
 with sigma of 0.02
 C8-C9 \\sim C8A-C9
 with sigma of 0.02
 C8-C11 \\sim C8A-C11
 with sigma of 0.02
 C8-C9A \\sim C8A-C9A
 with sigma of 0.02
 C8-C7A \\sim C8A-C7A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C11) = Uanis(C9)
Uanis(C1A) = Uanis(C10A)
Uanis(C12) = Uanis(C1A)
Uanis(C18) = Uanis(C10)
Uanis(C2A) = Uanis(C3A)
Uanis(C4A) = Uanis(C7A)
Uanis(C16) = Uanis(C6)
Uanis(C8) = Uanis(C8A)
Uanis(C12) = Uanis(C8)
Uanis(C4A) = Uanis(C5)
Uanis(C13) = Uanis(C9A)
Uanis(C14) = Uanis(C7)
Uanis(O5) = Uanis(O3A)
Uanis(C10A) = Uanis(C9A)
4. Others
 Fixed Sof: O3(0.5) O5(0.5) C1(0.5) C2(0.5) C3(0.5) H3(0.5) C4(0.5) H4(0.5)
 C5(0.5) H5(0.5) C6(0.5) H6(0.5) C7(0.5) C8(0.5) C9(0.5) H9(0.5) C10(0.5)
 H10(0.5) O5A(0.5) O3A(0.5) C6A(0.5) H6A(0.5) C5A(0.5) H5A(0.5) C4A(0.5)
 H4A(0.5) C3A(0.5) H3A(0.5) C2A(0.5) C10A(0.5) H10A(0.5) C9A(0.5) H9A(0.5)
 C1A(0.5) C7A(0.5) C8A(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B), C19(H19A,H19B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C14(H14), C6A(H6A),
 C5A(H5A), C4A(H4A), C3A(H3A), C10A(H10A), C9A(H9A)
5.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              68706
_olex2_submission_special_instructions 'No special instructions were received'