Synthesis of unsymmetrical 2,3,7,8-tetrabromo <i>meso</i>-5,10,11,16-tetraaryl- triphyrin(2.1.1) and its use in the synthesis of sterically crowded 2,3,5,7,8,10,11,16-octaarylated triphyrin(2.1.1)s.
Sharma, Akrti; Kaur, Gurpreet; Ravikanth, Mangalampalli; Organic & biomolecular chemistry 22 (2024) 838–849; doi:10.1039/d3ob01886e

data_7159749
_publ_section_title
;
 Synthesis of unsymmetrical 2,3,7,8-tetrabromo
 <i>meso</i>-5,10,11,16-tetraaryl- triphyrin(2.1.1) and its use in the
 synthesis of sterically crowded 2,3,5,7,8,10,11,16-octaarylated
 triphyrin(2.1.1)s.
;
_journal_issue                   4
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              838
_journal_page_last               849
_journal_paper_doi               10.1039/d3ob01886e
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C44 H31 Br4 N3'
_chemical_formula_sum            'C44 H31 Br4 N3'
_chemical_formula_weight         921.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2023-11-13
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-11-14 deposited with the CCDC.	2023-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.027(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   41.29(3)
_cell_length_b                   8.552(7)
_cell_length_c                   23.83(2)
_cell_measurement_reflns_used    7372
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      25.681
_cell_measurement_theta_min      2.144
_cell_volume                     7744(11)
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      301.00
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1477
_diffrn_reflns_av_unetI/netI     0.1152
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       50
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            43561
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         2.144
_exptl_absorpt_coefficient_mu    4.192
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.378
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       block
_exptl_crystal_F_000             3648
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.201
_exptl_crystal_size_min          0.013
_refine_diff_density_max         0.772
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     464
_refine_ls_number_reflns         7330
_refine_ls_number_restraints     469
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.1683
_refine_ls_R_factor_gt           0.0586
_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^)+(0.0316P)^2^+16.5819P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1273
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3308
_reflns_number_total             7330
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01886e2.cif
_cod_data_source_block           MR_AS_BR4
_cod_depositor_comments          'Adding full bibliography for 7159749.cif.'
_cod_original_cell_volume        7746(12)
_cod_database_code               7159749
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H3(0.059) H13(0.064) H14(0.066) H18(0.097) H19(0.117) H21(0.107)
 H22(0.089) H23A(0.216) H23B(0.216) H23C(0.216) H25(0.06) H26(0.069) H28(0.076)
 H29(0.065) H30A(0.14) H30B(0.14) H30C(0.14) H32(0.058) H33(0.072) H35(0.08)
 H36(0.067) H37A(0.155) H37B(0.155) H37C(0.155) H39(0.083) H40(0.114) H42(0.15)
 H43(0.122) H44A(0.303) H44B(0.303) H44C(0.303)
 Fixed X: H3(0.661202) H13(0.717209) H14(0.655402) H18(0.566636) H19(0.540868)
 H21(0.600172) H22(0.630922) H23A(0.565141) H23B(0.541885) H23C(0.528786)
 H25(0.776003) H26(0.832402) H28(0.83439) H29(0.778051) H30A(0.893385)
 H30B(0.884531) H30C(0.879963) H32(0.785351) H33(0.832332) H35(0.799675)
 H36(0.751556) H37A(0.853088) H37B(0.850161) H37C(0.873781) H39(0.612973)
 H40(0.579134) H42(0.520355) H43(0.552637) H44A(0.500769) H44B(0.518826)
 H44C(0.534728)
 Fixed Y: H3(0.624892) H13(0.33205) H14(0.253716) H18(1.091496) H19(1.24825)
 H21(1.059547) H22(0.92002) H23A(1.292034) H23B(1.367632) H23C(1.217322)
 H25(0.784021) H26(0.878905) H28(0.959894) H29(0.868654) H30A(0.895706)
 H30B(1.037482) H30C(1.053297) H32(0.461702) H33(0.331853) H35(0.476999)
 H36(0.592956) H37A(0.200673) H37B(0.310636) H37C(0.359203) H39(0.133916) H40(-
 0.06693) H42(0.23484) H43(0.441485) H44A(-0.072166) H44B(-0.060054) H44C(-
 0.169912)
 Fixed Z: H3(0.55654) H13(0.684289) H14(0.65034) H18(0.418894) H19(0.334815)
 H21(0.255758) H22(0.34559) H23A(0.211588) H23B(0.242901) H23C(0.202705)
 H25(0.54231) H26(0.573471) H28(0.738871) H29(0.708574) H30A(0.685627)
 H30B(0.718854) H30C(0.650637) H32(0.62018) H33(0.693707) H35(0.822164)
 H36(0.749026) H37A(0.802043) H37B(0.852474) H37C(0.817448) H39(0.541524)
 H40(0.552626) H42(0.597844) H43(0.584329) H44A(0.547388) H44B(0.618602)
 H44C(0.583233)
;
_shelx_res_checksum              84765
_olex2_submission_special_instructions 'No special instructions were received'