Stepwise Reduction of Octaethyl-β,β′-dioxochlorin Isomers: Access to Structurally and Electronically Diverse Hydroporphyrins
Chaudhri, Nivedita; Zeller, Matthias; Brückner, Christian; The Journal of Organic Chemistry  (2020) –; doi:10.1021/acs.joc.0c01989

data_4038918
_publ_section_title
;
 Stepwise Reduction of Octaethyl-\b,\b&#x2032;-dioxochlorin Isomers:
 Access to Structurally and Electronically Diverse Hydroporphyrins
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01989
_journal_year                    2020
_chemical_formula_sum            'C36 H48 N4 O2'
_chemical_formula_weight         568.78
_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   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 120.870(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.938(2)
_cell_length_b                   15.8655(9)
_cell_length_c                   16.4572(11)
_cell_measurement_reflns_used    9901
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.0450
_cell_measurement_theta_min      2.3697
_cell_volume                     6485.4(7)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'Apex3 v2018.7-2 (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_structure_refinement
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1030 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            160260
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.251
_diffrn_reflns_theta_min         2.369
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_description       plate
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     791
_refine_ls_number_reflns         12438
_refine_ls_number_restraints     1534
_refine_ls_restrained_S_all      1.109
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0671
_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^)+(0.0668P)^2^+5.3598P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1789
_refine_ls_wR_factor_ref         0.1887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9870
_reflns_number_total             12438
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01989_si_003.cif
_cod_data_source_block           9-O7-(OH)18-rac
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4038918
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.989
_shelx_res_checksum              60921
_shelx_hkl_checksum              99874