Phyllostictine A: total synthesis, structural verification and determination of substructure responsible for plant growth inhibition.
Riemer, Martin; Uzunova, Veselina V.; Riemer, Nastja; Clarkson, Guy J.; Pereira, Nicole; Napier, Richard; Shipman, Michael; Chemical communications (Cambridge, England) 54 (2018) 7211–7214; doi:10.1039/c8cc03349h

data_7121835
_publ_section_title
;
 Phyllostictine A: total synthesis, structural verification and
 determination of substructure responsible for plant growth inhibition.
;
_journal_issue                   52
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              7211
_journal_page_last               7214
_journal_paper_doi               10.1039/c8cc03349h
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C7 H11 N O4'
_chemical_formula_sum            'C7 H11 N O4'
_chemical_formula_weight         173.17
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-04-20 deposited with the CCDC.
2018-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.086(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7222(3)
_cell_length_b                   7.91107(17)
_cell_length_c                   11.6743(3)
_cell_measurement_reflns_used    3668
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      77.2920
_cell_measurement_theta_min      3.8760
_cell_volume                     878.00(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.44a (Rigaku OD, 2018)'
_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(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_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   -118.00  40.00   1.00    2.25    --  -42.21   0.00 -30.00  158
  2  \w     -3.00  75.00   1.00    2.25    --   42.21 -99.00 120.00   78
  3  \w     18.00  63.00   1.00    2.25    --   42.21  57.00 120.00   45
  4  \w     55.00 111.00   1.00    2.25    --   42.21  57.00 -90.00   56
  5  \w     33.00  86.00   1.00    2.25    --   42.21-125.00 -90.00   53
  6  \w     87.00 112.00   1.00    2.25    --   42.21  57.00 120.00   25
  7  \w    101.00 131.00   1.00    9.00    --  114.00 111.00 -60.00   30
  8  \w     43.00 105.00   1.00    9.00    --  114.00 -61.00 -90.00   62
  9  \w     90.00 172.00   1.00    9.00    --  114.00  30.00 -90.00   82
 10  \w    135.00 166.00   1.00    9.00    --  114.00 -15.00 -30.00   31
 11  \w    111.00 144.00   1.00    9.00    --  114.00 111.00  60.00   33
 12  \w     41.00 139.00   1.00    9.00    --  114.00 -45.00  90.00   98
 13  \w     54.00 116.00   1.00    9.00    --  114.00-111.00 -90.00   62
 14  \w     59.00 119.00   1.00    9.00    --  114.00 178.00 120.00   60
 15  \w     32.00 106.00   1.00    9.00    --  114.00 -95.00 120.00   74
 16  \w    101.00 159.00   1.00    9.00    --  114.00 111.00  30.00   58
 17  \w    116.00 142.00   1.00    9.00    --  114.00 178.00 -60.00   26
 18  \w     89.00 114.00   1.00    9.00    --  114.00  77.00-150.00   25
 19  \w    118.00 167.00   1.00    9.00    --  114.00  77.00-150.00   49
 20  \w     74.00 108.00   1.00    9.00    --  114.00 -95.00   0.00   34
 21  \w     49.00  84.00   1.00    9.00    --  114.00-102.00  73.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1184105000
_diffrn_orient_matrix_UB_12      0.1062756000
_diffrn_orient_matrix_UB_13      -0.0336372000
_diffrn_orient_matrix_UB_21      0.0440176000
_diffrn_orient_matrix_UB_22      -0.1526208000
_diffrn_orient_matrix_UB_23      -0.0659728000
_diffrn_orient_matrix_UB_31      -0.1015467000
_diffrn_orient_matrix_UB_32      0.0576600000
_diffrn_orient_matrix_UB_33      -0.1127893000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6016
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.334
_diffrn_reflns_theta_min         6.655
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.923
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.44a (Rigaku Oxford Diffraction, 2018)
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    1.310
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1844
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0382
_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^)+(0.0650P)^2^+0.1427P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1716
_reflns_number_total             1844
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc03349h2.cif
_cod_data_source_block           mr2
_cod_depositor_comments          'Adding full bibliography for 7121835.cif.'
_cod_database_code               7121835
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C20 H20 N2 O2'
_shelx_estimated_absorpt_t_max   0.947
_shelx_estimated_absorpt_t_min   0.687
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_olex2_refinement_description
;
The OH was located in a difference map but placed at a calculated position for refinement.
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C1(H1A,H1B,H1C), C9(H9A,H9B,H9C)
2.c Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_shelx_res_checksum              33799
_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 1.376
_oxdiff_exptl_absorpt_empirical_full_min 0.758