Biomimetic synthesis of the pyrrolobenzoxazine core of paeciloxazine
Schwaebisch, Dirk; Tchabanenko, Kirill; Adlington, Robert M.; Cowley, Andrew M.; Baldwin, Jack E.; Chemical Communications  (2004) 2552–2553; doi:10.1039/b412300j

data_7111480
_publ_section_title
;
 Biomimetic synthesis of the pyrrolobenzoxazine core of paeciloxazine
;
_journal_issue                   22
_journal_name_full               'Chemical Communications'
_journal_page_first              2552
_journal_page_last               2553
_journal_paper_doi               10.1039/b412300j
_journal_year                    2004
_chemical_absolute_configuration syn
_chemical_compound_source
;
synthesis as described
;
_chemical_formula_moiety         ' C27 H20 N6 O14 '
_chemical_formula_sum            'C27 H20 N6 O14'
_chemical_formula_weight         652.49
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 102.9509(11)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.4739(2)
_cell_length_b                   8.0449(2)
_cell_length_c                   14.3256(3)
_cell_measurement_reflns_used    12972
_cell_measurement_temperature    150
_cell_measurement_theta_max      28
_cell_measurement_theta_min      5
_cell_volume                     1401.02(5)
_computing_cell_refinement
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_data_collection
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_publication_material
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_refinement
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
;
Nonius KappaCCD
;
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12972
_diffrn_reflns_theta_full        27.481
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         5.221
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_crystal_colour            ' yellow '
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_description       ' block '
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.16
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1631
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         2833
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.001450
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.424 0.110 0.134
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0419
_refine_ls_wR_factor_gt          0.0350
_refine_ls_wR_factor_ref         0.0350
_reflns_limit_h_max              15
_reflns_limit_h_min              -16
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                2833
_reflns_number_total             3394
_reflns_threshold_expression     I>3.00u(I)
_cod_data_source_file            b412300jsup1.cif
_cod_data_source_block           ARC889
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'P 1 21 1 '
_cod_original_formula_sum        ' C27 H20 N6 O14 '
_cod_database_code               7111480