Isolation and crystal structure of 4-((2-(methoxycarbonyl)phenyl)amino)-2-methyl-4-oxobutanoic acid from Delphinium Grandiflorum, C13H15N1O5
Li, Guo-Qiang; Li, Yun-Yi; Zhao, Yi-Ting; Xu, Qing-Peng; Li, Yao-Lan; Wang, Guo-Cai; Zeitschrift für Kristallographie - New Crystal Structures 234 (2019) 521–522; doi:10.1515/ncrs-2018-0517

data_8105767
_publ_section_title
;
 Isolation and crystal structure of
 4-((2-(methoxycarbonyl)phenyl)amino)-2-methyl-4-oxobutanoic acid from
 Delphinium Grandiflorum, C13H15N1O5
;
_journal_issue                   3
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              521
_journal_page_last               522
_journal_paper_doi               10.1515/ncrs-2018-0517
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C13 H15 N O5'
_chemical_formula_sum            'C13 H15 N O5'
_chemical_formula_weight         265.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_cell_angle_alpha                100.254(8)
_cell_angle_beta                 100.036(8)
_cell_angle_gamma                94.760(8)
_cell_formula_units_Z            2
_cell_length_a                   7.9457(7)
_cell_length_b                   8.7190(9)
_cell_length_c                   9.9964(10)
_cell_measurement_reflns_used    1834
_cell_measurement_temperature    298
_cell_measurement_theta_max      62.8300
_cell_measurement_theta_min      5.2030
_cell_volume                     666.39(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)[1]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)[1]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)[2]'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)[2]'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0288
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details
;
  1 omega   16.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   57.0000  -60.0000 74

  2 omega  107.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000 -180.0000 26

  3 omega   68.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000 -180.0000 69

  4 omega  100.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  -30.0000 25

  5 omega  120.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000   90.0000 38

  6 omega  132.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000  120.0000 31

  7 omega   84.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000   60.0000 68

  8 omega   89.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  118.4536 26

  9 omega   48.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  150.0000 28

 10 omega   36.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  118.4536 36

 11 omega   27.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   60.0000 38

 12 omega   54.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000   60.0000 26

 13 omega   62.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000  120.0000 46

 14 omega   49.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -30.0000 25

 15 omega   45.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -87.0000  -26.2857 39

 16 omega   60.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -116.0000  -99.0000 32

 17 omega   84.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000 -149.5167 28

 18 omega   90.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -88.0000 -159.1718 26

 19 omega   32.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -150.0000 33

 20 omega   27.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000 -180.0000 33

 21 omega   31.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -116.0000  -99.0000 25

 22 omega   20.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  -42.6543 87

 23 omega   29.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -89.0000   57.0285 91

 24 omega   30.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   90.0000 26

 25 omega   11.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934  -99.0000  150.0000 64

 26 omega  -25.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934  -99.0000  150.0000 33

 27 omega   22.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -60.0000 54

 28 omega   26.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -150.0000 42

 29 omega   18.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   19.0000 -120.0000 88

 30 omega  -94.00  -53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.9934  178.0000  -60.0000 41

 31 omega -109.00  -84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.9934 -178.0000 -150.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Gemini S ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0433980000
_diffrn_orient_matrix_UB_12      -0.1179904000
_diffrn_orient_matrix_UB_13      0.0903460000
_diffrn_orient_matrix_UB_21      -0.1086960000
_diffrn_orient_matrix_UB_22      -0.1106563000
_diffrn_orient_matrix_UB_23      -0.1291583000
_diffrn_orient_matrix_UB_31      0.1600475000
_diffrn_orient_matrix_UB_32      -0.0807908000
_diffrn_orient_matrix_UB_33      -0.0251029000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4205
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        62.751
_diffrn_reflns_theta_max         62.751
_diffrn_reflns_theta_min         5.191
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.148
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2102
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0453
_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^)+(0.0632P)^2^+0.1591P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1243
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1836
_reflns_number_total             2102
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_ncrs-2018-0517_suppl.cif
_cod_data_source_block           lgq-fyc-m-3
_cod_original_cell_volume        666.38(11)
_cod_database_code               8105767
_reflns_odcompleteness_completeness 95.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     63.60
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4A), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C13(H13A,H13B,H13C)
;
_shelx_res_checksum              93716