Synthesis of the Reported Pyranonaphthoquinone Structure of the Indoleamine-2,3-dioxygenase Inhibitor Annulin B by Regioselective Diels-Alder Reaction.
Inman, Martyn; Carvalho, Catarina; Lewis, William; Moody, Christopher J.; The Journal of organic chemistry 81 (2016) 7924–7930; doi:10.1021/acs.joc.6b01622

data_4037160
_publ_section_title
;
 Synthesis of the Reported Pyranonaphthoquinone Structure of the
 Indoleamine-2,3-dioxygenase Inhibitor Annulin B by Regioselective
 Diels-Alder Reaction.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7924
_journal_page_last               7930
_journal_paper_doi               10.1021/acs.joc.6b01622
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C21 H22 O7'
_chemical_formula_sum            'C21 H22 O7'
_chemical_formula_weight         386.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-01-20
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.438(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.7940(4)
_cell_length_b                   10.8229(5)
_cell_length_c                   22.0776(14)
_cell_measurement_reflns_used    6988
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.6910
_cell_measurement_theta_min      4.5250
_cell_volume                     1850.58(17)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(2)
_diffrn_crystal_treatment        'flash frozen in gaseous N2'
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 5.2349
_diffrn_detector_type            'Agilent Diffraction Atlas S2 detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w   -109.00 -13.00   2.00    2.00    --  -38.50 -57.00-120.00   48
  2  \w    -94.00  -2.00   2.00    2.00    --  -38.50 125.00  90.00   46
  3  \w    -50.00  34.00   2.00    2.00    --  -38.50  38.00  30.00   42
  4  \w     33.00  97.00   2.00    2.00    --  104.50 -45.00 120.00   32
  5  \w     30.00  90.00   2.00    2.00    --  104.50 -30.00  60.00   30
  6  \w     23.00 109.00   2.00    2.00    --  104.50 -94.00-120.00   43
  7  \w     30.00  90.00   2.00    2.00    --  104.50 -30.00 150.00   30
  8  \w     33.00 121.00   2.00    2.00    --  104.50-125.00  90.00   44
  9  \w     30.00  90.00   2.00    2.00    --  104.50 -30.00 -90.00   30
 10  \w     30.00  90.00   2.00    2.00    --  104.50 -30.00-180.00   30
 11  \w     31.00 135.00   2.00    2.00    --  104.50 -77.00   0.00   52
 12  \w     73.00 177.00   2.00    2.00    --  104.50  77.00  60.00   52
;
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'SuperNova, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1859706000
_diffrn_orient_matrix_UB_12      0.0505541000
_diffrn_orient_matrix_UB_13      -0.0082156000
_diffrn_orient_matrix_UB_21      -0.0068313000
_diffrn_orient_matrix_UB_22      -0.0078922000
_diffrn_orient_matrix_UB_23      0.0693480000
_diffrn_orient_matrix_UB_31      0.0702245000
_diffrn_orient_matrix_UB_32      0.1328761000
_diffrn_orient_matrix_UB_33      0.0071509000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_wavelength_determination fundamental
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10836
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.622
_diffrn_reflns_theta_min         4.556
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           0.8
_diffrn_source_power             0.04
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.871
_exptl_absorpt_correction_T_max  0.832
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.738
_exptl_crystal_size_mid          0.513
_exptl_crystal_size_min          0.237
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0058(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0371
_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^)+(0.0506P)^2^+0.8258P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1000
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3410
_reflns_number_total             3631
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01622_si_002.cif
_cod_data_source_block           micjmn
_cod_original_cell_volume        1850.59(18)
_cod_database_code               4037160
_nottingham_internal_coll_name   MICJMN
_nottingham_internal_coll_number 15479
_nottingham_internal_coll_client MI/CJM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'ofand \w scans'
_nottingham_internal_coll_frame_time 'degrees,, 2.00'
_nottingham_internal_coll_frame_width 'in, 2.00'
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   15/01/2016
_nottingham_internal_coll_location NOTTS
_nottingham_internal_coll_instrument 'GVB, PL13110001'
_nottingham_internal_process_date 18/01/2016
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 20/1/2016
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 20/1/2016
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 20/1/2016
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 20/1/2016
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C21 H22 O7'
_chemical_oxdiff_usercomment
'MICJMN #15479 GVB-851 IN FOMBLIN FILM ON MICROMOUNT FOR MI/CJM'
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,
 H22C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              64849
_shelx_hkl_checksum              87258
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.623
_oxdiff_exptl_absorpt_empirical_full_min 0.577