Synthesis of Nonracemic 1,4-Benzoxazines via Ring Opening/Cyclization of Activated Aziridines with 2-Halophenols: Formal Synthesis of Levofloxacin.
Mal, Abhijit; Wani, Imtiyaz Ahmad; Goswami, Gaurav; Ghorai, Manas K.; The Journal of organic chemistry 83 (2018) 7907–7918; doi:10.1021/acs.joc.8b00788

data_4035609
_publ_section_title
;
 Synthesis of Nonracemic 1,4-Benzoxazines via Ring Opening/Cyclization of
 Activated Aziridines with 2-Halophenols: Formal Synthesis of
 Levofloxacin.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7907
_journal_page_last               7918
_journal_paper_doi               10.1021/acs.joc.8b00788
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C21 H18 F N O3 S'
_chemical_formula_sum            'C21 H18 F N O3 S'
_chemical_formula_weight         383.42
_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
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Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
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_cell_angle_alpha                90
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_cell_volume                     1819.2(4)
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_computing_structure_solution    'SIR97(Altomare, et. al. 1999)'
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_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_Laue_measured_fraction_full 0.996
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_diffrn_reflns_theta_max         25.109
_diffrn_reflns_theta_min         2.480
_exptl_absorpt_coefficient_mu    0.210
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_exptl_crystal_colour            White
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_refine_ls_structure_factor_coef Fsqd
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'w=1/[\s^2^(Fo^2^)+(0.0601P)^2^+0.2395P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
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_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2158
_reflns_number_total             3237
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00788_si_003.cif
_cod_data_source_block           9decd
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Empirical' was
changed to 'empirical' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/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 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4035609
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C6(H6), C17(H17), C18(H18), C12(H12), C3(H3), C2(H2), C1(H1),
 C10(H10), C21(H21), C14(H14), C13(H13)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_shelx_res_checksum              92987
_shelx_hkl_checksum              85706
_olex2_submission_special_instructions 'No special instructions were received'