Use of the Nascent Isocyclic Ring to Anchor Assembly of the Full Skeleton of Model Chlorophylls
Wang, Pengzhi; Lu, Futai; Lindsey, Jonathan S.; The Journal of Organic Chemistry  (2019) –; doi:10.1021/acs.joc.9b02770

data_4037746
_publ_section_title
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 Use of the Nascent Isocyclic Ring to Anchor Assembly of the Full Skeleton
 of Model Chlorophylls
;
_journal_name_full               'The Journal of Organic Chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02770
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C13 H12 Br N O'
_chemical_formula_sum            'C13 H12 Br N O'
_chemical_formula_weight         278.15
_chemical_name_common            Br-py-Ar
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   3.9928(2)
_cell_length_b                   20.0972(6)
_cell_length_c                   28.7175(10)
_cell_measurement_reflns_used    4275
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      24.4715
_cell_measurement_theta_min      2.4739
_cell_volume                     2304.41(16)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_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 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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  0.0579
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_limit_h_max       4
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_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            16291
_diffrn_reflns_theta_full        25.41
_diffrn_reflns_theta_max         25.41
_diffrn_reflns_theta_min         1.42
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.544
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.161
_exptl_crystal_size_mid          0.047
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_refine_diff_density_max         0.724
_refine_diff_density_min         -0.583
_refine_ls_abs_structure_details
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.110(14)
_refine_ls_extinction_method     none
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_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4241
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0288P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0721
_reflns_number_gt                3670
_reflns_number_total             4241
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02770_si_004.cif
_cod_data_source_block           rds734
_cod_depositor_comments
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The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
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_cod_database_code               4037746
_shelx_res_checksum              65743
_shelx_hkl_checksum              42061