Fusarochromene, a novel tryptophan-derived metabolite from <i>Fusarium sacchari</i>.
Marshall, James W.; de Mattos-Shipley, Kate M J; Ghannam, Iman A. Y.; Munawar, Asifa; Killen, Jonathan C.; Lazarus, Colin M.; Cox, Russell J.; Willis, Christine L.; Simpson, Thomas J.; Organic & biomolecular chemistry 19 (2021) 182–187; doi:10.1039/d0ob02031a

data_7157837
_publ_section_title
;
 Fusarochromene, a novel tryptophan-derived metabolite from <i>Fusarium
 sacchari</i>.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              182
_journal_page_last               187
_journal_paper_doi               10.1039/d0ob02031a
_journal_volume                  19
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H25 Br N2 O5'
_chemical_formula_sum            'C24 H25 Br N2 O5'
_chemical_formula_weight         501.37
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2020-08-10
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2020-08-10 deposited with the CCDC.	2020-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.9355(4)
_cell_length_b                   9.9998(8)
_cell_length_c                   44.492(3)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.36
_cell_measurement_theta_min      4.53
_cell_volume                     2195.9(3)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-1997  (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker Pt135 CCD area detector'
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'Bruker Mircostar Rotating anode'
_diffrn_measurement_device_type  'Rotating anode'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            15300
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        66.358
_diffrn_reflns_theta_max         66.358
_diffrn_reflns_theta_min         3.974
_diffrn_source                   'micro-focus rotating anode'
_diffrn_source_current           60.0
_diffrn_source_power             2.7
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    2.885
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_description       plate
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.004
_refine_diff_density_min         -1.311
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Flack x determined using 1392 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.229
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         3778
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.229
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0487
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0161P)^2^+7.3549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                3679
_reflns_number_total             3778
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob02031a2.cif
_cod_data_source_block           jwmvi60a
_cod_original_cell_volume        2195.8(3)
_cod_database_code               7157837
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B
 0.99 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C14(H14)
3.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C7(H7), C8(H8), C18(H18), C19(H19), C21(H21), C22(H22)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              94768
_shelx_hkl_checksum              91638
_olex2_submission_special_instructions 'No special instructions were received'