Synthesis and structural characterisation of bulky heptaaromatic (hetero)aryl o-substituted s-aryltetrazines
Mboyi, Clève D.; Daher, Ahmad; Khirzada, Neelab; Devillers, Charles H.; Cattey, Hélène; Fleurat-Lessard, Paul; Roger, Julien; Hierso, Jean-Cyrille; New Journal of Chemistry 44 (2020) 15235–15243; doi:10.1039/D0NJ02338H

data_7059894
_publ_section_title
;
 Synthesis and structural characterisation of bulky heptaaromatic
 (hetero)aryl o-substituted s-aryltetrazines
;
_journal_issue                   35
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              15235
_journal_page_last               15243
_journal_paper_doi               10.1039/D0NJ02338H
_journal_volume                  44
_journal_year                    2020
_chemical_formula_moiety         'C54 H58 N4, C H2 Cl2'
_chemical_formula_sum            'C55 H60 Cl2 N4'
_chemical_formula_weight         847.97
_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
_atom_sites_solution_primary     dual
_audit_update_record
;
2020-03-19 deposited with the CCDC.	2020-07-27 downloaded from the CCDC.
;
_cell_angle_alpha                77.642(2)
_cell_angle_beta                 74.455(2)
_cell_angle_gamma                88.158(2)
_cell_formula_units_Z            2
_cell_length_a                   11.4912(6)
_cell_length_b                   12.8803(8)
_cell_length_c                   17.1913(9)
_cell_measurement_reflns_used    9441
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.52
_cell_volume                     2393.7(2)
_computing_cell_refinement       'SAINT V8.40A (bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT V8.40A (bruker, 2016)'
_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      100.0
_diffrn_detector                 CMOS
_diffrn_detector_area_resol_mean '1024 x 1024'
_diffrn_detector_type            'Photon 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '\k-geometry diffractometer triump Mo'
_diffrn_measurement_device_type  'Bruker D8 Venture triumph Mo'
_diffrn_measurement_method       '\f and \w scans''
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  'TRIUMPH curved crystal'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0782
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            105384
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_min         2.376
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-90C'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6769
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0748 before and 0.0638 after correction. The Ratio of minimum to maximum transmission is 0.9079. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_recrystallization_method
'The material was recrystallised from a mixture of ether and dichloromethane  by slow evaporation'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.579
_refine_diff_density_min         -1.249
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     593
_refine_ls_number_reflns         11025
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0653
_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^)+(0.0586P)^2^+3.8275P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1641
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8080
_reflns_number_total             11025
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj02338h2.cif
_cod_data_source_block           Compound_4
_cod_depositor_comments
'Adding full bibliography for 7059892--7059896.cif.'
_cod_original_cell_volume        2393.8(2)
_cod_database_code               7059894
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.949
_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
2. Others
 Sof(C27A)=Sof(H27D)=Sof(H27E)=Sof(H27F)=Sof(C26A)=Sof(H26D)=Sof(H26E)=
 Sof(H26F)=Sof(C25A)=Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(1)
 Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C26)=Sof(H26A)=Sof(H26B)=Sof(H26C)=
 Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C55(H55A,H55B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C12(H12), C13(H13), C19(H19),
 C20(H20), C22(H22), C23(H23), C31(H31), C32(H32), C33(H33), C36(H36), C37(H37),
  C39(H39), C40(H40), C46(H46), C47(H47), C49(H49), C50(H50)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C42(H42A,H42B,H42C), C43(H43A,
 H43B,H43C), C44(H44A,H44B,H44C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C),
 C54(H54A,H54B,H54C), C27A(H27D,H27E,H27F), C26A(H26D,H26E,H26F), C25A(H25D,
 H25E,H25F)
;
_shelx_res_checksum              93854
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a mylar loop with oil'
_olex2_submission_special_instructions 'No special instructions were received'