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_7229361
_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 H8 N2 O3'
_chemical_formula_sum            'C12 H8 N2 O3'
_chemical_formula_weight         228.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_audit_update_record
;
2017-08-19 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                95.529(8)
_cell_angle_beta                 103.372(9)
_cell_angle_gamma                115.216(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2887(8)
_cell_length_b                   7.9722(7)
_cell_length_c                   9.8335(10)
_cell_measurement_reflns_used    5384
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.2070
_cell_measurement_theta_min      4.0090
_cell_volume                     490.45(10)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9832
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_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    -83.00   3.00   1.00    2.50    --  -16.31 -63.00 -83.15   86
  2  \w    -84.00   0.00   1.00    2.50    --  -16.31 -57.00-180.00   84
  3  \w    -84.00   0.00   1.00    2.50    --  -16.31 -57.00   0.00   84
  4  \w    -83.00   1.00   1.00    2.50    --  -16.31 -60.00 107.64   84
  5  \w    -51.00  33.00   1.00    2.50    --   16.39 -53.00-169.19   84
  6  \w      0.00  84.00   1.00    2.50    --   16.39  57.00 120.00   84
  7  \w    -51.00  33.00   1.00    2.50    --   16.39 -57.00-120.00   84
  8  \w    -53.00  36.00   1.00    2.50    --   16.39 -37.00 120.00   89
  9  \w    -51.00  33.00   1.00    2.50    --   16.39 -57.00 -60.00   84
 10  \w    -51.00  33.00   1.00    2.50    --   16.39 -57.00   0.00   84
 11  \w    -50.00  36.00   1.00    2.50    --   16.39 -65.00  86.52   86
 12  \w    -51.00  33.00   1.00    2.50    --   16.39 -57.00 120.00   84
 13  \w    -51.00  33.00   1.00    2.50    --   16.39 -58.00  40.91   84
 14  \w    -55.00  46.00   1.00    2.50    --   16.39 -19.00 150.00  101
 15  \w    -51.00  33.00   1.00    2.50    --   16.39 -57.00-180.00   84
 16  \w    -51.00  33.00   1.00    2.50    --   16.39 -57.00 150.00   84
 17  \w    -51.00  33.00   1.00    2.50    --   16.39 -56.00 -14.63   84
 18  \w    -53.00  14.00   1.00    2.50    --   16.39 -37.00  30.00   67
 19  \w    -53.00  36.00   1.00    2.50    --   16.39 -37.00 -60.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0872321000
_diffrn_orient_matrix_UB_12      0.0163778000
_diffrn_orient_matrix_UB_13      -0.0310373000
_diffrn_orient_matrix_UB_21      0.0695790000
_diffrn_orient_matrix_UB_22      0.0989059000
_diffrn_orient_matrix_UB_23      0.0148119000
_diffrn_orient_matrix_UB_31      0.0168616000
_diffrn_orient_matrix_UB_32      -0.0109287000
_diffrn_orient_matrix_UB_33      -0.0678060000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0644
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16711
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.194
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.936
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.545
_exptl_crystal_description       irregular
_exptl_crystal_F_000             236
_exptl_crystal_preparation       'Fragment cut from larger crystal'
_exptl_crystal_size_max          0.777
_exptl_crystal_size_mid          0.586
_exptl_crystal_size_min          0.447
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2245
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0592
_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^)+(0.1000P)^2^+0.1910P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1652
_refine_ls_wR_factor_ref         0.1690
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2079
_reflns_number_total             2245
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra10483a2.cif
_cod_data_source_block           slb_jones_3
_cod_original_cell_volume        490.45(9)
_cod_database_code               7229361
_chemical_oxdiff_formula         C12H8N2O3
_chemical_oxdiff_usercomment     'Alan Jones 1'
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C9(H9)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_shelx_res_checksum              33105
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method Loop
_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 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.756