Synthesis of 24 Bacteriochlorin Isotopologues, Each Containing a Symmetrical Pair of (13)C or (15)N Atoms in the Inner Core of the Macrocycle.
Chen, Chih-Yuan; Bocian, David F.; Lindsey, Jonathan S.; The Journal of organic chemistry 79 (2014) 1001–; doi:10.1021/jo402488n

data_4029013
_publ_section_title
;
 Synthesis of 24 Bacteriochlorin Isotopologues, Each Containing a
 Symmetrical Pair of (13)C or (15)N Atoms in the Inner Core of the
 Macrocycle.
;
_journal_issue                   3
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1001
_journal_paper_doi               10.1021/jo402488n
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C11 H9 N O3 S'
_chemical_formula_weight         235.25
_chemical_melting_point          428
_chemical_name_common            10-NA
_chemical_name_systematic
; 
4-Benzenesulfonyl-2-formylpyrrole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 98.1280(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5682(4)
_cell_length_b                   7.3873(2)
_cell_length_c                   11.2454(4)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    110.(2)
_cell_measurement_theta_max      33.2029
_cell_measurement_theta_min      3.2071
_cell_volume                     1033.59(6)
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS Inc., 2009)'
_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS Inc., 2009)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker-Nonius X8 Kappa APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0158
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23042
_diffrn_reflns_theta_full        32.03
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         1.64
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.302
_exptl_absorpt_correction_T_max  0.93
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.371
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     11
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0462P)^2^+0.4245P]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0914
_reflns_number_gt                3261
_reflns_number_total             3584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo402488n_si_002.cif
_cod_data_source_block           x05063
_cod_database_code               4029013