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_4032767
_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         'C35 H41 N3 O4'
_chemical_formula_sum            'C35 H41 N3 O4'
_chemical_formula_weight         567.71
_chemical_name_systematic
;
8,12,13,17-tetraethyl-2,2-di(methoxycarbonyl)-7,18-dimethyl-
2,3-dihydro-21-carbaporphyrin
;
_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   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                66.264(7)
_cell_angle_beta                 71.517(8)
_cell_angle_gamma                61.662(7)
_cell_formula_units_Z            2
_cell_length_a                   12.093(2)
_cell_length_b                   12.1052(19)
_cell_length_c                   12.739(2)
_cell_measurement_reflns_used    9490
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.82
_cell_measurement_theta_min      3.05
_cell_volume                     1484.0(4)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
A total of 2165 frames were collected.  
The total exposure time was 144.33 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  0.0708
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            41857
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         1.768
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'APEX3 v2016.9-0 (Bruker, 2016)'
_exptl_crystal_colour            bronze
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.025
_refine_diff_density_max         0.458
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     633
_refine_ls_number_reflns         5832
_refine_ls_number_restraints     808
_refine_ls_restrained_S_all      0.981
_refine_ls_R_factor_all          0.1258
_refine_ls_R_factor_gt           0.0715
_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^)+(0.1228P)^2^+0.6298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1872
_refine_ls_wR_factor_ref         0.2245
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3364
_reflns_number_total             5832
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01831_si_002.cif
_cod_data_source_block           GMF17023_0m_compound_32
_cod_depositor_comments
'Adding full bibliography for 4032764--4032767.cif.'
_cod_original_cell_volume        1484.1(4)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4032767
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.977
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              84590
_shelx_hkl_checksum              16507