Synthesis and absolute configuration assignment of albucidin: a late-stage reductive deiodination by visible light photocatalysis.
Zhang, Hu; Liu, Peng-Fei; Chen, Qiong; Wu, Qiong-You; Seville, Anne; Gu, Yu-Cheng; Clough, John; Zhou, Shao-Lin; Yang, Guang-Fu; Organic & biomolecular chemistry 14 (2016) 3482–3485; doi:10.1039/c6ob00371k

data_7155018
_publ_section_title
;
 Synthesis and absolute configuration assignment of albucidin: a
 late-stage reductive deiodination by visible light photocatalysis.
;
_journal_issue                   13
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3482
_journal_page_last               3485
_journal_paper_doi               10.1039/c6ob00371k
_journal_volume                  14
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C11 H13 N5 O4'
_chemical_formula_sum            'C11 H13 N5 O4'
_chemical_formula_weight         279.26
_chemical_melting_point          495.0(10)
_chemical_name_systematic        'Compound 10'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2016-03-08 deposited with the CCDC.
2016-03-08 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.4773(10)
_cell_length_b                   8.2931(11)
_cell_length_c                   20.419(3)
_cell_measurement_reflns_used    7409
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      31.62
_cell_measurement_theta_min      2.65
_cell_volume                     1266.2(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.0362
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            12797
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.9730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick,2008'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(9)
_refine_ls_extinction_coef       0.009(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3689
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0376
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.0802P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1079
_refine_ls_wR_factor_ref         0.1122
_reflns_number_gt                3413
_reflns_number_total             3689
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6ob00371k2.cif
_cod_data_source_block           mo_130227b_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '494-496' was changed to '495.0(10)'
- the average value was taken and precision was estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7155018--7155020.cif.
;
_cod_database_code               7155018
_solvent_exptl_crystal_recrystallization_method 'CH2Cl2, CH3OH'