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_7125848
_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         'C37 H47 N10 O8'
_chemical_formula_sum            'C37 H47 N10 O8'
_chemical_formula_weight         759.84
_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             2019-01-22
_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                94.206(3)
_cell_angle_beta                 106.083(3)
_cell_angle_gamma                103.833(3)
_cell_formula_units_Z            2
_cell_length_a                   10.9930(3)
_cell_length_b                   12.9694(4)
_cell_length_c                   14.3295(7)
_cell_measurement_reflns_used    9539
_cell_measurement_temperature    223.00(10)
_cell_measurement_theta_max      71.1470
_cell_measurement_theta_min      4.3180
_cell_volume                     1884.65(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      223.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     -8.00  17.00   1.00    2.00    --   34.00 101.00-139.09   25
  2  \w   -114.00 -20.00   1.00    2.00    --  -39.69 -38.00 150.00   94
  3  \w   -112.00 -13.00   1.00    2.00    --  -39.69 -57.00 -30.00   99
  4  \w    -60.00  35.00   1.00    2.00    --  -39.69  38.00 120.00   95
  5  \w    -79.00 -14.00   1.00    2.00    --  -39.69 -57.00  60.00   65
  6  \w   -128.00 -36.00   1.00    2.00    --  -39.69-178.00  60.00   92
  7  \w     60.00 128.00   1.00    2.00    --   39.69 178.00  90.00   68
  8  \w      6.00  31.00   1.00    2.00    --   42.00  88.00  36.92   25
  9  \w     12.00  38.00   1.00    2.00    --   46.00  82.00 102.26   26
 10  \w     11.00  36.00   1.00    2.00    --   46.00  84.00 -69.41   25
 11  \w     11.00  36.00   1.00    2.00    --   46.00  84.00 166.48   25
 12  \w     18.00  43.00   1.00    2.00    --   50.00  79.00  -9.20   25
 13  \w     17.00  43.00   1.00    2.00    --   50.00  80.00  43.40   26
 14  \w     16.00  41.00   1.00    2.00    --   50.00  81.00-116.70   25
 15  \w    100.00 128.00   1.00    2.00    --   62.00  77.00-176.72   28
 16  \w     29.00  57.00   1.00    2.00    --   62.00  77.00 129.40   28
 17  \w     30.00  68.00   1.00    2.00    --   62.00  75.00 -33.76   38
 18  \w     30.00  70.00   1.00    2.00    --   62.00  74.00  22.40   40
 19  \w     30.00  62.00   1.00    2.00    --   62.00  77.00-176.72   32
 20  \w     30.00  60.00   1.00    2.00    --   62.00  75.00  97.78   30
 21  \w     77.00 120.00   1.00    2.00    --   62.00  74.00  22.40   43
 22  \w     35.00  70.00   1.00    2.00    --   66.00  75.00 -68.32   35
 23  \w     33.00  60.00   1.00    2.00    --   66.00  77.00 -94.02   27
 24  \w     33.00  62.00   1.00    2.00    --   66.00  77.00-131.97   29
 25  \w     42.00 150.00   1.00   20.00    --   74.00  76.00  44.57  108
 26  \w     41.00  99.00   1.00   20.00    --   74.00  77.00 128.53   58
 27  \w     89.00 118.00   1.00   20.00    --  102.66-125.00-120.00   29
 28  \w     70.00 162.00   1.00   20.00    --  102.66  77.00 -30.00   92
 29  \w    145.00 173.00   1.00   20.00    --  102.66  77.00 -90.00   28
 30  \w    135.00 174.00   1.00   20.00    --  102.66 125.00   0.00   39
 31  \w     70.00  97.00   1.00   20.00    --  102.66  77.00 -90.00   27
 32  \w     76.00 111.00   1.00   20.00    --  102.66  61.00  90.00   35
 33  \w     70.00 178.00   1.00   20.00    --  102.66  77.00  90.00  108
 34  \w     76.00 162.00   1.00   20.00    --  102.66  61.00 -90.00   86
 35  \w     70.00 177.00   1.00   20.00    --  102.66  77.00-180.00  107
 36  \w     71.00 171.00   1.00   20.00    --  102.66  77.00   0.00  100
 37  \w    129.00 157.00   1.00   20.00    --  102.66  77.00 150.00   28
 38  \w     37.00 135.00   1.00   20.00    --  102.66 -77.00  90.00   98
 39  \w     70.00  97.00   1.00   20.00    --  102.66  77.00 150.00   27
 40  \w     70.00 178.00   1.00   20.00    --  102.66  77.00 120.00  108
 41  \w    113.00 144.00   1.00   20.00    --  102.66  77.00  60.00   31
 42  \w    106.00 174.00   1.00   20.00    --  102.66  77.00-150.00   68
 43  \w     74.00 102.00   1.00   20.00    --  102.66  61.00-150.00   28
 44  \w     24.00 109.00   1.00   20.00    --  102.66 -94.00 -60.00   85
 45  \w     74.00 102.00   1.00   20.00    --  102.66  61.00-120.00   28
 46  \w     74.00 129.00   1.00   20.00    --  102.66  61.00-180.00   55
 47  \w     70.00  97.00   1.00   20.00    --  102.66  77.00  60.00   27
 48  \w     70.00  98.00   1.00   20.00    --  102.66  77.00-150.00   28
 49  \w     75.00 101.00   1.00   20.00    --  102.66  61.00 -60.00   26
 50  \w    112.00 137.00   1.00   20.00    --  102.66  77.00-120.00   25
 51  \w     70.00  99.00   1.00   20.00    --  102.66  77.00-120.00   29
 52  \w     70.00 174.00   1.00   20.00    --  102.66  77.00  30.00  104
 53  \w     70.00 171.00   1.00   20.00    --  102.66  77.00 -60.00  101
 54  \w     35.00 108.00   1.00   20.00    --  102.66 -94.00  30.00   73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0040283000
_diffrn_orient_matrix_UB_12      -0.0059171000
_diffrn_orient_matrix_UB_13      -0.1086249000
_diffrn_orient_matrix_UB_21      -0.1514019000
_diffrn_orient_matrix_UB_22      -0.0302506000
_diffrn_orient_matrix_UB_23      -0.0314477000
_diffrn_orient_matrix_UB_31      0.0039279000
_diffrn_orient_matrix_UB_32      0.1198242000
_diffrn_orient_matrix_UB_33      0.0041780000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28530
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.479
_diffrn_reflns_theta_min         3.246
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80607
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       prism
_exptl_crystal_F_000             806
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: DCM, Acetone'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.520
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         7214
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0652
_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^)+(0.0854P)^2^+1.6120P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1735
_refine_ls_wR_factor_ref         0.1824
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6065
_reflns_number_total             7214
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc09021e2.cif
_cod_data_source_block           oligoacac8
_cod_database_code               7125848
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.819
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C26(H26A,
 H26B), C27(H27A,H27B), C28(H28A,H28B), C30(H30A,H30B), C31(H31A,H31B),
 C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N8(H8), N9(H9), N10(H10), C1(H1A), C5(H5), C8(H8A),
 C12(H12), C15(H15), C17(H17), C20(H20)
2.c Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C37(H37A,H37B,H37C)
;