Fused bis-azacalixphyrin that reaches NIR-II absorptions.
Lavaud, Lucien; Azarias, Cloé; Canard, Gabriel; Pascal, Simon; Galiana, Joachim; Giorgi, Michel; Chen, Zhongrui; Jacquemin, Denis; Siri, Olivier; Chemical communications (Cambridge, England) 56 (2020) 896–899; doi:10.1039/c9cc09021e

data_7125847
_publ_section_title
;
 Fused bis-azacalixphyrin that reaches NIR-II absorptions.
;
_journal_issue                   6
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              896
_journal_page_last               899
_journal_paper_doi               10.1039/c9cc09021e
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety
'C30 H14 F4 N12 O16, 4(C2 H6 O S), C H3 O0.3 S0.3, C H3 O0.7 S0.7'
_chemical_formula_sum            'C40 H44 F4 N12 O21 S5'
_chemical_formula_weight         1265.17
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-12-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-03-25 deposited with the CCDC.	2019-12-06 downloaded from the CCDC.
;
_cell_angle_alpha                81.9569(7)
_cell_angle_beta                 83.7579(7)
_cell_angle_gamma                84.127(2)
_cell_formula_units_Z            2
_cell_length_a                   12.8294(2)
_cell_length_b                   12.9628(2)
_cell_length_c                   17.3033(5)
_cell_measurement_reflns_used    32846
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.77
_cell_measurement_theta_min      2.39
_cell_measurement_wavelength     0.71073
_cell_volume                     2821.31(10)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'Omega + Phi scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.054
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            13720
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.772
_diffrn_reflns_theta_min         2.388
_exptl_absorpt_coefficient_mu    0.303
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1304
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DMSO, Et2O'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.881
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     796
_refine_ls_number_reflns         13720
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1416
_refine_ls_R_factor_gt           0.0891
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1250P)^2^+2.3717P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2328
_refine_ls_wR_factor_ref         0.2752
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8142
_reflns_number_total             13720
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09021e2.cif
_cod_data_source_block           zc2x29
_cod_database_code               7125847
_shelx_shelxl_version_number     2016/4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Shared sites
{C31A, C31B}
{C32A, C32B}
{C33A, C33B}
{C34A, C34B}
{C35A, C35B}
{C36A, C36B}
{C39A, C39B}
{C40A, C40B}
3. Uiso/Uaniso restraints and constraints
S2A \\sim C34A \\sim S2B \\sim C34B: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.02
S1A \\sim C32A \\sim S1B \\sim C32B: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.02
S4A \\sim C38A \\sim S4B \\sim C38B: within 1.7A with sigma of 0.005 and sigma
for terminal atoms of 0.01
S4A \\sim S4B \\sim C37: within 1.7A with sigma of 0.005 and sigma for terminal
atoms of 0.01
Uanis(C31A) = Uanis(C31B)
Uanis(C32A) = Uanis(C32B)
Uanis(C33A) = Uanis(C33B)
Uanis(C34A) = Uanis(C34B)
Uanis(C35A) = Uanis(C35B)
Uanis(C36A) = Uanis(C36B)
Uanis(C39A) = Uanis(C39B)
Uanis(C40A) = Uanis(C40B)
Uanis(C38A) = Uanis(C38B)
4. Others
 Fixed Sof: S1A(0.5) C31A(0.5) H31A(0.5) H31B(0.5) H31C(0.5) C32A(0.5)
 H32A(0.5) H32B(0.5) H32C(0.5) S1B(0.5) C31B(0.5) H31D(0.5) H31E(0.5) H31F(0.5)
 C32B(0.5) H32D(0.5) H32E(0.5) H32F(0.5) S2A(0.5) C33A(0.5) H33A(0.5) H33B(0.5)
 H33C(0.5) C34A(0.5) H34A(0.5) H34B(0.5) H34C(0.5) S2B(0.5) C33B(0.5) H33D(0.5)
 H33E(0.5) H33F(0.5) C34B(0.5) H34D(0.5) H34E(0.5) H34F(0.5) S3A(0.5) C35A(0.5)
 H35A(0.5) H35B(0.5) H35C(0.5) C36A(0.5) H36A(0.5) H36B(0.5) H36C(0.5) S3B(0.5)
 C35B(0.5) H35D(0.5) H35E(0.5) H35F(0.5) C36B(0.5) H36D(0.5) H36E(0.5)
 H36F(0.5) S4A(0.3) C38B(0.7) H38A(0.7) H38B(0.7) H38C(0.7) S4B(0.7) S5A(0.3)
 C39A(0.5) H39A(0.5) H39B(0.5) H39C(0.5) C40A(0.5) H40A(0.5) H40B(0.5)
 H40C(0.5) O21A(0.3) S5B(0.7) C39B(0.5) H39D(0.5) H39E(0.5) H39F(0.5) C40B(0.5)
 H40D(0.5) H40E(0.5) H40F(0.5) O21B(0.7) C38A(0.3) H38D(0.3) H38E(0.3)
 H38F(0.3) H37A(0.3) H37B(0.3) H37C(0.3) H37D(0.7) H37E(0.7) H37F(0.7)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C9(H9), C12(H12), C15(H15), C18(H18), C20(H20), C23(H23),
 C27(H27), C30(H30), N1(H1A), N2(H2), N3(H3), N4(H4A)
5.b Idealised Me refined with riding coordinates:
 C31A(H31A,H31B,H31C), C32A(H32A,H32B,H32C), C31B(H31D,H31E,H31F), C32B(H32D,
 H32E,H32F), C33A(H33A,H33B,H33C), C34A(H34A,H34B,H34C), C33B(H33D,H33E,H33F),
 C34B(H34D,H34E,H34F), C35A(H35A,H35B,H35C), C36A(H36A,H36B,H36C), C35B(H35D,
 H35E,H35F), C36B(H36D,H36E,H36F), C38B(H38A,H38B,H38C), C39A(H39A,H39B,H39C),
 C40A(H40A,H40B,H40C), C39B(H39D,H39E,H39F), C40B(H40D,H40E,H40F), C38A(H38D,
 H38E,H38F), C37(H37A,H37B,H37C), C37(H37D,H37E,H37F)
;
_olex2_submission_special_instructions 'No special instructions were received'