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_4038915
_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_absolute_configuration ukn
_chemical_formula_sum            'C38 H54 N4 O2'
_chemical_formula_weight         598.85
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3711(5)
_cell_length_b                   12.8050(5)
_cell_length_c                   20.1366(7)
_cell_measurement_reflns_used    9781
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      33.7377
_cell_measurement_theta_min      2.4235
_cell_volume                     3447.7(2)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       'Apex3 v2019.1-0 (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_structure_refinement
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev1117 (H\"ubschle et al., 2011)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker AXS D8 Quest diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_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  0.0558
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            98276
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.774
_diffrn_reflns_theta_min         2.423
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6401
_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            green
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_description       plate
_exptl_crystal_F_000             1304
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 4940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(3)
_refine_ls_extinction_coef       0.0049(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         13744
_refine_ls_number_restraints     679
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0550P)^2^+0.4599P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1085
_refine_ls_wR_factor_ref         0.1157
_reflns_Friedel_coverage         0.946
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                11570
_reflns_number_total             13744
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01989_si_003.cif
_cod_data_source_block           10-(OMe)7_17-Z
_cod_database_code               4038915
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.996
_shelx_res_checksum              43432
_shelx_hkl_checksum              88665