Synthesis of a tethered dibenzotetramethyltetraaza[14]annulene macrocycle and the di-nickel(ii) derivative
Dey, Soumyajit; Dewey, Jacob R.; Wayland, Bradford B.; Zdilla, Michael J.; New Journal of Chemistry 42 (2018) 19369–; doi:10.1039/C8NJ03154A

data_7057749
_publ_section_title
;
 Synthesis of a tethered dibenzotetramethyltetraaza[14]annulene macrocycle
 and the di-nickel(ii) derivative
;
_journal_issue                   24
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              19369
_journal_paper_doi               10.1039/C8NJ03154A
_journal_volume                  42
_journal_year                    2018
_chemical_formula_moiety         'C52 H50 N8 O2, 0.5(C5 H12)'
_chemical_formula_sum            'C54.5 H56 N8 O2'
_chemical_formula_weight         855.07
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-09-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-09-06 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                62.50(5)
_cell_angle_beta                 82.90(3)
_cell_angle_gamma                73.44(3)
_cell_formula_units_Z            2
_cell_length_a                   11.74(2)
_cell_length_b                   14.45(3)
_cell_length_c                   15.40(3)
_cell_measurement_reflns_used    477
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.73
_cell_measurement_theta_min      2.74
_cell_volume                     2221(7)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (Bruker AXS)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.797
_diffrn_measured_fraction_theta_max 0.797
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1086
_diffrn_reflns_av_unetI/netI     0.2102
_diffrn_reflns_Laue_measured_fraction_full 0.797
_diffrn_reflns_Laue_measured_fraction_max 0.797
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6369
_diffrn_reflns_point_group_measured_fraction_full 0.797
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_theta_full        23.256
_diffrn_reflns_theta_max         23.256
_diffrn_reflns_theta_min         1.645
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.3824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1753 before and 0.0532 after correction.
The Ratio of minimum to maximum transmission is 0.5132.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             910
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       0.013(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     613
_refine_ls_number_reflns         5073
_refine_ls_number_restraints     548
_refine_ls_restrained_S_all      0.913
_refine_ls_R_factor_all          0.1988
_refine_ls_R_factor_gt           0.0875
_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^)+(0.0860P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1863
_refine_ls_wR_factor_ref         0.2453
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2149
_reflns_number_total             5073
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8nj03154a2.cif
_cod_data_source_block           rev
_cod_depositor_comments          'Adding full bibliography for 7057749.cif.'
_cod_original_formula_sum        'C54.50 H56 N8 O2'
_cod_database_code               7057749
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.986
_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
 C2-C3 \\sim C3-C4 \\sim C4-C1 \\sim C1-C1A
 with sigma of 0.02
 C2-C4 \\sim C4-C1A \\sim C3-C1
 with sigma of 0.04
3. Restrained planarity
 C2, C3, C4, C1, C1A
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C2 \\sim C3 \\sim C4 \\sim C1 \\sim C1A: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
5. Rigid body (RIGU) restrains
 C51, N1, C2AA, C7, C1AA, C20, C8, C12, C0AA, C23, C9, N2, C11, N4, C19, O1,
 C10, C3AA, C18, C50, C52, C5, C21, C13, C17, C49, C47, C6, N3, C14, C16, C48,
 C24, C22, C15, O2, C26, C25, C27, N8, C43, N5, C44, C42, C31, C37, C41, C32,
 C36, N7, C38, C40, C33, N6, C35, C30, C39, C34, C28, C29, C46, C45
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C2, C3, C4, C1, C1A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4, C2, C3, C1, C1A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C43, C25, N8, C26
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Fixed Sof: C2(0.5) H2A(0.5) H2B(0.5) H2C(0.5) C3(0.5) H3A(0.5) H3B(0.5)
 C4(0.5) H4A(0.5) H4B(0.5) C1(0.5) H1A(0.5) H1B(0.5) C1A(0.5) H1AA(0.5)
 H1AB(0.5) H1AC(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C1(H1A,H1B)
7.b Me refined with riding coordinates:
 C2(H2A,H2B,H2C), C1A(H1AA,H1AB,H1AC)
7.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4), N5(H5), N7(H7), C5(H5A), C8(H8), C9(H9), C10(H10), C11(H11),
 C14(H14), C15(H15), C16(H16), C17(H17), C29(H29), C32(H32), C33(H33), C34(H34),
  C35(H35), C38(H38), C39(H39), C40(H40), C41(H41), C48(H48), C49(H49),
 C50(H50), C52(H52)
7.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C46(H46A,
 H46B,H46C)
;
_shelx_res_checksum              63729
_olex2_submission_special_instructions 'No special instructions were received'