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_7229360
_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     direct
_audit_creation_date             2017-08-19
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-08-19 deposited with the CCDC.
2017-10-09 downloaded from the CCDC.
;
_cell_angle_alpha                98.989(5)
_cell_angle_beta                 90.256(4)
_cell_angle_gamma                98.291(6)
_cell_formula_units_Z            4
_cell_length_a                   5.6166(3)
_cell_length_b                   10.8878(9)
_cell_length_c                   16.1616(7)
_cell_measurement_reflns_used    3354
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.9150
_cell_measurement_theta_min      4.6190
_cell_volume                     965.61(11)
_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      100.01(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 0.993
_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    -66.00  18.00   1.00   15.39    --  -42.56  57.00 120.00   84
  2  \w    -64.00  27.00   1.00   15.39    --  -42.56  57.00 -30.00   91
  3  \w      9.00  48.00   1.00   15.39    --   42.56 -99.00  30.00   39
  4  \w     44.00 109.00   1.00   61.53    --  106.63 -94.00 -30.00   65
  5  \w     55.00 130.00   1.00   61.53    --  106.63 -30.00-150.00   75
  6  \w     40.00 115.00   1.00   61.53    --  106.63 -61.00 -30.00   75
  7  \w     62.00 170.00   1.00   61.53    --  106.63  15.00  90.00  108
  8  \w    149.00 174.00   1.00   61.53    --  106.63  30.00 150.00   25
  9  \w     90.00 125.00   1.00   61.53    --  106.63  30.00 150.00   35
 10  \w     46.00 130.00   1.00   61.53    --  106.63 -30.00  90.00   84
 11  \w     77.00 104.00   1.00   61.53    --  106.63-113.00 134.00   27
 12  \w     43.00 125.00   1.00   61.53    --  106.63 -77.00 120.00   82
 13  \w     35.00  73.00   1.00   61.53    --  106.63-113.00 134.00   38
 14  \w     36.00 107.00   1.00   61.53    --  106.63-125.00 -60.00   71
 15  \w   -113.00 -18.00   1.00   15.39    --  -42.56 -57.00-180.00   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      -0.0584387000
_diffrn_orient_matrix_UB_12      -0.0239544000
_diffrn_orient_matrix_UB_13      -0.0948880000
_diffrn_orient_matrix_UB_21      0.0358927000
_diffrn_orient_matrix_UB_22      0.1428069000
_diffrn_orient_matrix_UB_23      -0.0006873000
_diffrn_orient_matrix_UB_31      0.2686762000
_diffrn_orient_matrix_UB_32      -0.0023612000
_diffrn_orient_matrix_UB_33      -0.0177946000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6140
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.072
_diffrn_reflns_theta_min         4.156
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.970
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.851
_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    1.570
_exptl_crystal_description       needle
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         3634
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0451
_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^)+(0.0530P)^2^+0.7340P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1247
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3101
_reflns_number_total             3634
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ra10483a2.cif
_cod_data_source_block           9
_cod_original_cell_volume        965.60(11)
_cod_database_code               7229360
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C12 H8 N2 O3'
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              95418
_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 1.404
_oxdiff_exptl_absorpt_empirical_full_min 0.809