Total synthesis and structural revision of a mangrove alkaloid
Green, Michael T.; Peczkowski, Gary R.; Al-Ani, Aneesa J.; Benjamin, Sophie L.; Simpkins, Nigel S.; Jones, Alan M.; RSC Adv. 7 (2017) 48754–; doi:10.1039/C7RA10483A

data_7229362
_publ_section_title
;
 Total synthesis and structural revision of a mangrove alkaloid
;
_journal_issue                   77
_journal_name_full               'RSC Adv.'
_journal_page_first              48754
_journal_paper_doi               10.1039/C7RA10483A
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C12 H10 N2 O4'
_chemical_formula_sum            'C12 H10 N2 O4'
_chemical_formula_weight         246.22
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2017-08-19 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.229(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.8352(11)
_cell_length_b                   7.7514(3)
_cell_length_c                   11.3697(4)
_cell_measurement_reflns_used    8503
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      28.7050
_cell_measurement_theta_min      3.7630
_cell_volume                     2225.22(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1768
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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      7.00  33.00   1.00   10.82    --   14.54 -57.00  30.00   26
  2  \w    -19.00  30.00   1.00   10.82    --  -13.60 -99.00 -90.00   49
  3  \w    -17.00  50.00   1.00   10.82    --   14.54  19.00  60.00   67
  4  \w     38.00  93.00   1.00   10.82    --   14.54  38.00 150.00   55
  5  \w     35.00 106.00   1.00   10.82    --   14.54 178.00 150.00   71
  6  \w     -8.00  93.00   1.00   10.82    --   14.54  38.00-120.00  101
  7  \w    -69.00  26.00   1.00   10.82    --   14.54 -77.00 -90.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0066866000
_diffrn_orient_matrix_UB_12      -0.0763776000
_diffrn_orient_matrix_UB_13      -0.0341863000
_diffrn_orient_matrix_UB_21      -0.0272850000
_diffrn_orient_matrix_UB_22      0.0187393000
_diffrn_orient_matrix_UB_23      -0.0054747000
_diffrn_orient_matrix_UB_31      -0.0000368000
_diffrn_orient_matrix_UB_32      0.0468024000
_diffrn_orient_matrix_UB_33      -0.0536257000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            22129
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.204
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.793
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_description       block
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.128
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4550
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0392P)^2^+1.8760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3925
_reflns_number_total             4550
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra10483a2.cif
_cod_data_source_block           AMJ_001
_cod_original_cell_volume        2225.20(15)
_cod_database_code               7229362
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C11 H10 N O'
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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:
 C2(H2), C102(H102)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C111(H11C,H11D)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C105(H105), C106(H106), C107(H107), C108(H108)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C112(H11E,H11F,H11G)
;
_shelx_res_checksum              7750
_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 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.814