#------------------------------------------------------------------------------
#$Date: 2022-09-13 12:33:29 +0300 (Tue, 13 Sep 2022) $
#$Revision: 277804 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/57/8105767.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105767
loop_
_publ_author_name
'Li, Guo-Qiang'
'Li, Yun-Yi'
'Zhao, Yi-Ting'
'Xu, Qing-Peng'
'Li, Yao-Lan'
'Wang, Guo-Cai'
_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 für 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
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   16.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   57.0000  -60.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega  107.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   68.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   45.0000 -180.0000 69

#__ type_ start__ end____ width___ exp.time_
  4 omega  100.00  125.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega  120.00  158.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
  6 omega  132.00  163.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega   84.00  152.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000   60.0000 68

#__ type_ start__ end____ width___ exp.time_
  8 omega   89.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  118.4536 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   48.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  150.0000 28

#__ type_ start__ end____ width___ exp.time_
 10 omega   36.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  118.4536 36

#__ type_ start__ end____ width___ exp.time_
 11 omega   27.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
 12 omega   54.00   80.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   15.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   62.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   30.0000  120.0000 46

#__ type_ start__ end____ width___ exp.time_
 14 omega   49.00   74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   45.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -87.0000  -26.2857 39

#__ type_ start__ end____ width___ exp.time_
 16 omega   60.00   92.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -116.0000  -99.0000 32

#__ type_ start__ end____ width___ exp.time_
 17 omega   84.00  112.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000 -149.5167 28

#__ type_ start__ end____ width___ exp.time_
 18 omega   90.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -88.0000 -159.1718 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   32.00   65.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -30.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
 20 omega   27.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -77.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 21 omega   31.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000 -116.0000  -99.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega   20.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  -42.6543 87

#__ type_ start__ end____ width___ exp.time_
 23 omega   29.00  120.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -89.0000   57.0285 91

#__ type_ start__ end____ width___ exp.time_
 24 omega   30.00   56.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -94.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   11.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934  -99.0000  150.0000 64

#__ type_ start__ end____ width___ exp.time_
 26 omega  -25.00    8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934  -99.0000  150.0000 33

#__ type_ start__ end____ width___ exp.time_
 27 omega   22.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
 28 omega   26.00   68.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000 -150.0000 42

#__ type_ start__ end____ width___ exp.time_
 29 omega   18.00  106.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       32.9934   19.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
 30 omega  -94.00  -53.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -32.9934  178.0000  -60.0000 41

#__ type_ start__ end____ width___ exp.time_
 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       'ω 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/[σ²(Fo²)+(0.0632P)²+0.1591P] where P=(Fo²+2Fc²)/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 > 2σ(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
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_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)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2853(3) -0.0576(2) -0.36828(15) 0.0879(6) Uani 1 1 d . . . . .
O2 O 0.1968(2) 0.13506(19) -0.23470(15) 0.0832(5) Uani 1 1 d . . . . .
O3 O 0.1965(3) 0.13901(18) 0.25536(14) 0.0884(6) Uani 1 1 d . . . . .
O4 O 0.27762(19) 0.46201(19) 0.51114(14) 0.0700(4) Uani 1 1 d . . . . .
H4 H 0.394(5) 0.484(5) 0.563(4) 0.161(14) Uiso 1 1 d . . . . .
O5 O 0.40732(17) 0.49284(18) 0.33690(14) 0.0664(4) Uani 1 1 d . . . . .
N1 N 0.19438(18) 0.11165(15) 0.02634(14) 0.0452(4) Uani 1 1 d . . . . .
H1 H 0.1655 0.1568 -0.0427 0.054 Uiso 1 1 calc R . . . .
C1 C 0.2869(2) -0.0849(2) -0.14020(17) 0.0448(4) Uani 1 1 d . . . . .
C2 C 0.26012(19) -0.03218(18) -0.00531(17) 0.0412(4) Uani 1 1 d . . . . .
C3 C 0.3020(2) -0.1243(2) 0.09368(18) 0.0490(4) Uani 1 1 d . . . . .
H3 H 0.2846 -0.0914 0.1834 0.059 Uiso 1 1 calc R . . . .
C4 C 0.3691(2) -0.2636(2) 0.0594(2) 0.0544(5) Uani 1 1 d . . . . .
H4A H 0.3974 -0.3232 0.1267 0.065 Uiso 1 1 calc R . . . .
C5 C 0.3946(2) -0.3157(2) -0.0724(2) 0.0579(5) Uani 1 1 d . . . . .
H5 H 0.4390 -0.4103 -0.0947 0.070 Uiso 1 1 calc R . . . .
C6 C 0.3538(2) -0.2266(2) -0.1711(2) 0.0542(5) Uani 1 1 d . . . . .
H6 H 0.3713 -0.2618 -0.2605 0.065 Uiso 1 1 calc R . . . .
C7 C 0.2502(2) 0.0096(2) -0.24936(19) 0.0539(5) Uani 1 1 d . . . . .
C8 C 0.2589(5) 0.0282(4) -0.4805(3) 0.1086(11) Uani 1 1 d . . . . .
H8A H 0.2872 -0.0323 -0.5619 0.163 Uiso 1 1 calc GR . . . .
H8B H 0.3313 0.1266 -0.4542 0.163 Uiso 1 1 calc GR . . . .
H8C H 0.1406 0.0471 -0.4996 0.163 Uiso 1 1 calc GR . . . .
C9 C 0.1701(2) 0.1891(2) 0.14937(17) 0.0473(4) Uani 1 1 d . . . . .
C10 C 0.1076(2) 0.3475(2) 0.14634(18) 0.0488(4) Uani 1 1 d . . . . .
H10A H -0.0062 0.3335 0.0885 0.059 Uiso 1 1 calc R . . . .
H10B H 0.1842 0.4096 0.1054 0.059 Uiso 1 1 calc R . . . .
C11 C 0.1002(2) 0.4355(2) 0.29040(19) 0.0506(4) Uani 1 1 d . . . . .
H11 H 0.0240 0.3710 0.3312 0.061 Uiso 1 1 calc R . . . .
C12 C 0.2758(2) 0.4640(2) 0.38131(18) 0.0503(4) Uani 1 1 d . . . . .
C13 C 0.0291(3) 0.5926(2) 0.2852(2) 0.0688(6) Uani 1 1 d . . . . .
H13A H 0.1050 0.6587 0.2488 0.103 Uiso 1 1 calc GR . . . .
H13B H 0.0205 0.6428 0.3770 0.103 Uiso 1 1 calc GR . . . .
H13C H -0.0828 0.5747 0.2266 0.103 Uiso 1 1 calc GR . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C7 O1 C8 116.81(18) . .
C9 N1 C2 129.23(14) . .
C2 C1 C7 121.39(15) . .
C6 C1 C2 119.22(15) . .
C6 C1 C7 119.37(16) . .
C1 C2 N1 119.28(14) . .
C3 C2 N1 122.11(15) . .
C3 C2 C1 118.61(15) . .
C4 C3 C2 120.48(17) . .
C5 C4 C3 121.02(16) . .
C4 C5 C6 119.24(17) . .
C5 C6 C1 121.42(18) . .
O1 C7 C1 112.66(16) . .
O2 C7 O1 121.66(17) . .
O2 C7 C1 125.67(17) . .
O3 C9 N1 123.93(16) . .
O3 C9 C10 121.44(16) . .
N1 C9 C10 114.63(14) . .
C9 C10 C11 111.95(14) . .
C10 C11 C13 111.42(16) . .
C12 C11 C10 110.54(14) . .
C12 C11 C13 109.30(15) . .
O4 C12 C11 115.01(16) . .
O5 C12 O4 122.58(17) . .
O5 C12 C11 122.36(16) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C7 1.315(2) .
O1 C8 1.451(3) .
O2 C7 1.199(2) .
O3 C9 1.208(2) .
O4 C12 1.299(2) .
O5 C12 1.229(2) .
N1 C2 1.404(2) .
N1 C9 1.347(2) .
C1 C2 1.404(2) .
C1 C6 1.391(2) .
C1 C7 1.485(2) .
C2 C3 1.395(2) .
C3 C4 1.378(3) .
C4 C5 1.370(3) .
C5 C6 1.373(3) .
C9 C10 1.510(2) .
C10 C11 1.520(2) .
C11 C12 1.502(3) .
C11 C13 1.530(3) .
