Synthesis and Properties of Carbaporphyrin and Carbachlorin Dimethyl Esters Derived from Cyclopentanedialdehydes.
Sahota, Navneet; Ferrence, Gregory M.; Lash, Timothy D.; The Journal of organic chemistry 82 (2017) 9715–9730; doi:10.1021/acs.joc.7b01831

data_4032766
_publ_section_title
;
 Synthesis and Properties of Carbaporphyrin and Carbachlorin Dimethyl
 Esters Derived from Cyclopentanedialdehydes.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9715
_journal_page_last               9730
_journal_paper_doi               10.1021/acs.joc.7b01831
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C36 H39 N3 Ni O4'
_chemical_formula_sum            'C36 H39 N3 Ni O4'
_chemical_formula_weight         636.39
_chemical_name_systematic
;
(8,12,13,17-tetraethyl-2,3-di(methoxycarbonyl)-7,18,21-trimethyl-
21-carbaporphyrinato)nickel(II)
;
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                91.141(3)
_cell_angle_beta                 90.468(3)
_cell_angle_gamma                94.066(3)
_cell_formula_units_Z            4
_cell_length_a                   9.3067(4)
_cell_length_b                   14.4582(6)
_cell_length_c                   23.3519(9)
_cell_measurement_reflns_used    9962
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.95
_cell_measurement_theta_min      2.19
_cell_volume                     3133.5(2)
_computing_cell_refinement       'Bruker SAINT (Bruker, 2016)'
_computing_data_collection       'Bruker APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT (Bruker, 2016)'
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and 
<i>Mercury CSD</i> (Macrae et al., 2008)
;
_computing_publication_material
;
<i>WinGX</i> (Farrugia, 1999)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
A total of 3672 frames were collected.  
The total exposure time was 61.20 hours.
;
_diffrn_measurement_device_type  'Bruker APEX-II CCD diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1130
_diffrn_reflns_av_unetI/netI     0.0916
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            73929
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.081
_diffrn_reflns_theta_min         1.412
_exptl_absorpt_coefficient_mu    0.663
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX3 v2016.9-0 (Bruker, 2016)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       long
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.285
_exptl_crystal_size_mid          0.058
_exptl_crystal_size_min          0.015
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.883
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     810
_refine_ls_number_reflns         12386
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.883
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0438P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0925
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7825
_reflns_number_total             12386
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01831_si_002.cif
_cod_data_source_block           GMF17025_0m_compound_31
_cod_depositor_comments
'Adding full bibliography for 4032764--4032767.cif.'
_cod_database_code               4032766
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.833
_shelx_estimated_absorpt_t_max   0.990
_shelx_res_checksum              24717
_shelx_hkl_checksum              34281