Synthesis of the Ring C Pyrrole of Native Chlorophylls and Bacteriochlorophylls.
Wang, Pengzhi; Chau Nguyen, Khiem; Lindsey, Jonathan S.; The Journal of organic chemistry 84 (2019) 11286–11293; doi:10.1021/acs.joc.9b01650

data_4033889
_publ_section_title
;
 Synthesis of the Ring C Pyrrole of Native Chlorophylls and
 Bacteriochlorophylls.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11286
_journal_page_last               11293
_journal_paper_doi               10.1021/acs.joc.9b01650
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C12 H12 Br N O2 S'
_chemical_formula_sum            'C12 H12 Br N O2 S'
_chemical_formula_weight         314.20
_chemical_name_common            Py-Ts-Me-Br
_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'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 94.671(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.1467(9)
_cell_length_b                   6.1735(4)
_cell_length_c                   15.7907(11)
_cell_measurement_reflns_used    255
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      29.5758
_cell_measurement_theta_min      2.5981
_cell_volume                     1277.33(15)
_computing_cell_refinement       'APEX3 v2018.1-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 882)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0362
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12231
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.59
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.370
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.418
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.598
_refine_diff_density_min         -0.442
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         3172
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0296P)^2^+0.6908P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0707
_reflns_number_gt                2424
_reflns_number_total             3172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01650_si_002.cif
_cod_data_source_block           rds816
_cod_database_code               4033889
_shelx_res_checksum              65984
_shelx_hkl_checksum              50543