Elucidation of naphthalene diimide metallomacrocycles and catenanes by solvent dependent excimer and exciplex emission
Boer, Stephanie A.; Cox, Rosalind P.; Beards, Michael; Wang, Huixin; Donald, William; Bell, Toby D. M.; Turner, David Roger; Chemical Communications  (2018) –; doi:10.1039/C8CC09191A

data_7122684
_publ_section_title
;
 Elucidation of naphthalene diimide metallomacrocycles and catenanes by
 solvent dependent excimer and exciplex emission
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC09191A
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_moiety         '2(C36 H34 Cd N4 O9)'
_chemical_formula_sum            'C72 H68 Cd2 N8 O18'
_chemical_formula_weight         1558.14
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_symmetry_space_group_name_Hall  'C 2c 2'
_symmetry_space_group_name_H-M   'C 2 2 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-03-10 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.463(4)
_cell_length_b                   30.555(6)
_cell_length_c                   30.775(6)
_cell_measurement_reflns_used    176547
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.375
_cell_measurement_theta_min      1.323
_cell_volume                     16421(6)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_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 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.7108
_diffrn_reflns_av_R_equivalents  0.1271
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            176547
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.375
_diffrn_reflns_theta_min         1.323
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'XScale within XDS'
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             6368
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.523
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.088
_refine_ls_abs_structure_details
;
 Flack x determined using 4326 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
_platon_squeeze_void_probe_radius                  1.20
_platon_squeeze_details                           SQUEEZE shows total voids containing 262 electrons per formula unit, which may contain 5 water and 2 DMF molecules which could not be modelled in the structure. 
;
_refine_ls_abs_structure_Flack   0.062(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     890
_refine_ls_number_reflns         16752
_refine_ls_number_restraints     178
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0865
_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^)+(0.1735P)^2^+14.0349P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2371
_refine_ls_wR_factor_ref         0.2682
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                11910
_reflns_number_total             16752
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc09191a2.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-Scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               7122684
_shelx_shelxl_version_number     2016/6
_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, All O(H,H) groups
2. Restrained distances
 N8-C73
 1.39 with sigma of 0.02
 C2-C1
 1.5 with sigma of 0.02
 C66-C65 = C67-C68 = C70-C71 = C72-C71
 1.39 with sigma of 0.02
 C18-C17
 1.5 with sigma of 0.02
 C15-C14
 1.5 with sigma of 0.02
 O19-H19D = O19-H19E
 0.82 with sigma of 0.02
 O18-H18A = O18-H18B
 0.82 with sigma of 0.001
 C43-C41 = C42-C41 = C40-C39 = C53-C52 = C54-C53 = C56-C54 = C4-C3
 1.5 with sigma of 0.02
 C18-C18_$1
 3.6 with sigma of 0.04
 H19D-H19E
 1.38 with sigma of 0.04
 H19E-Cd2
 2.8 with sigma of 0.04
 C3-C5
 2.5 with sigma of 0.04
 H19E_$2-H19E
 2.1 with sigma of 0.04
 H18A-H18B
 1.38 with sigma of 0.04
 C56-C55
 2.5 with sigma of 0.04
 Cd2-H19D \\sim Cd2-H19E
 with sigma of 0.02
 H35_$3-H56A \\sim H56C-H35_$3
 with sigma of 0.02
3. Rigid bond restraints
 N8, C69, C70, C71, C72, C73
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C3, C4, C5, C6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C40, C41, C42, C43
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N3, C27, C28, C29, C30, C31
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
 C53, C54, C55, C56
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C65) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C42) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C55) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C38) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C5) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C29) \\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C33)
\\sim Ueq, Uanis(N32) \\sim Ueq: with sigma of 0.05 and sigma for terminal
atoms of 0.1
Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36) \\sim Ueq, Uanis(C37)
\\sim Ueq: with sigma of 0.05 and sigma for terminal atoms of 0.1
5. Rigid body (RIGU) restrains
 C15, C16, C17, C18, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C15(H15), C17(H17), C39(H39), C41(H41), C52(H52), C54(H54)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C16(H16A,H16B), C40(H40A,H40B), C53(H53A,H53B)
6.c Me refined with riding coordinates:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C18(H18C,H18D,H18E), C19(H19A,H19B,H19C),
 C42(H42A,H42B,H42C), C43(H43A,H43B,H43C), C55(H55A,H55B,H55C)
6.d Aromatic/amide H refined with riding coordinates:
 C27(H27), C28(H28), C29(H29), C30(H30), C9(H9), C13(H13), C22(H22), C26(H26),
 C34(H34), C35(H35), C36(H36), C37(H37), C46(H46), C50(H50), C59(H59), C63(H63),
  C64(H64), C65(H65), C66(H66), C67(H67), C70(H70), C71(H71), C72(H72), C73(H73)
6.e Fitted hexagon refined as free rotating group:
 N3(C27,C28,C29,C30,C31), N32(C33,C34,C35,C36,C37)
6.f Idealised Me refined as rotating group:
 C56(H56A,H56B,H56C)
;
_shelx_res_checksum              61285
_shelx_fab_checksum              91292
_olex2_submission_special_instructions 'No special instructions were received'