#------------------------------------------------------------------------------
#$Date: 2024-01-06 11:25:31 +0200 (Sat, 06 Jan 2024) $
#$Revision: 288868 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/96/7159604.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_7159604
loop_
_publ_author_name
'Lee, Stephanie'
'Söhnel, Tilo'
'Sperry, Jonathan'
_publ_section_title
;
 Support studies toward the hicksoane alkaloids reveal cascade reactions
 of a (tryptophanamido)methylglycinate.
;
_journal_issue                   43
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              8708
_journal_page_last               8715
_journal_paper_doi               10.1039/d3ob01596c
_journal_volume                  21
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'Cl, C12 H14 N3 O, H O0.5'
_chemical_formula_sum            'C12 H15 Cl N3 O1.5'
_chemical_formula_weight         260.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-07-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-07-16 deposited with the CCDC.	2023-10-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.543(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4988(3)
_cell_length_b                   7.09306(15)
_cell_length_c                   13.9973(3)
_cell_measurement_reflns_used    3630
_cell_measurement_temperature    120(1)
_cell_measurement_theta_max      71.6460
_cell_measurement_theta_min      6.4680
_cell_volume                     1211.31(5)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     15.00  47.00   0.50    0.33    --   47.23 -83.00  74.00   64
  2  ω      1.00  27.00   0.50    0.33    --   47.23 -19.00 120.00   52
  3  ω     25.00  71.50   0.50    1.33    --   97.33 -61.00 150.00   93
  4  ω     73.00  99.00   0.50    1.33    --   97.33 -83.00  74.00   52
  5  ω     46.00 106.00   0.50    1.33    --   97.33 -77.00 -90.00  120
  6  ω     24.00  50.50   0.50    1.33    --   97.33 -45.00-150.00   53
  7  ω     20.00  46.50   0.50    1.33    --   97.33 -45.00-120.00   53
  8  ω     20.00  50.50   0.50    1.33    --   97.33 -45.00 -60.00   61
  9  ω     -1.00  37.00   0.50    0.33    --   47.23 -99.00-150.00   76
 10  ω     22.00  50.00   0.50    1.33    --   97.33 -45.00  60.00   56
 11  ω     21.00  51.00   0.50    1.33    --   97.33 -45.00 150.00   60
 12  ω    -33.00  -1.00   0.50    0.33    --   47.23 -19.00 120.00   64
 13  ω    -40.00   0.00   0.50    0.33    --  -47.23  38.00 120.00   80
 14  ω    -68.00 -28.00   0.50    1.33    --  -90.25  61.00 120.00   80
 15  ω    -66.00 -19.50   0.50    1.33    --  -90.25  61.00  30.00   93
 16  ω    -83.00 -33.00   0.50    1.33    --  -90.25 111.00 120.00  100
 17  ω     -2.00  26.00   0.50    0.33    --  -47.23  83.00-164.00   56
 18  ω    -37.00  -9.00   0.50    0.33    --  -47.23  83.00-164.00   56
 19  ω    -41.00 -14.50   0.50    1.33    --  -90.25 111.00-150.00   53
 20  ω    -66.00 -40.00   0.50    1.33    --  -90.25  83.00-164.00   52
 21  ω    -51.00 -15.00   0.50    1.33    --  -90.25  45.00-150.00   72
 22  ω    -78.00 -47.50   0.50    1.33    --  -90.25 111.00-150.00   61
 23  ω   -157.00 -81.00   0.50    1.33    --  -90.25 -83.00  74.00  152
 24  ω   -153.00 -83.50   0.50    1.33    --  -90.25 -95.00   0.00  139
 25  ω   -112.00 -73.50   0.50    0.33    --  -47.23-125.00-120.00   77
 26  ω    109.00 135.00   0.50    1.33    --   97.33  83.00-164.00   52
 27  ω     67.00 129.00   0.50    1.33    --   97.33 178.00-150.00  124
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 200K'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0995991000
_diffrn_orient_matrix_UB_12      0.1332182000
_diffrn_orient_matrix_UB_13      0.0231810000
_diffrn_orient_matrix_UB_21      0.0644034000
_diffrn_orient_matrix_UB_22      -0.1349865000
_diffrn_orient_matrix_UB_23      -0.0530193000
_diffrn_orient_matrix_UB_31      -0.0433640000
_diffrn_orient_matrix_UB_32      0.1058443000
_diffrn_orient_matrix_UB_33      -0.0967520000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4201
_diffrn_reflns_point_group_measured_fraction_full 0.842
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.156
_diffrn_reflns_theta_min         3.235
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.742
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55888
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_description       needle
_exptl_crystal_F_000             548
_exptl_crystal_recrystallization_method EtOH/MeOH
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 645 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         1911
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0281
_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)+(0.0389P)²+0.6219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0734
_refine_ls_wR_factor_ref         0.0739
_reflns_Friedel_coverage         0.540
_reflns_Friedel_fraction_full    0.657
_reflns_Friedel_fraction_max     0.613
_reflns_number_gt                1875
_reflns_number_total             1911
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob01596c2.cif
_cod_data_source_block           syl-06-23_2
_cod_depositor_comments
'Adding full bibliography for 7159603--7159605.cif.'
_cod_original_cell_volume        1211.31(4)
_cod_original_formula_sum        'C12 H15 Cl N3 O1.50'
_cod_database_code               7159604
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C13 H14 N4 O2'
_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.
;
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.447
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O2-H2C
 0.85 with sigma of 0.02
3.a Free rotating group:
 O2(H2C)
3.b Ternary CH refined with riding coordinates:
 C9(H9)
3.c Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C8(H8A,H8B), C11(H11A,H11B)
3.d Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
3.e X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_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 1.872
_oxdiff_exptl_absorpt_empirical_full_min 0.499
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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
Cl1 Cl 0.09333(4) 0.32127(9) -0.14258(4) 0.02109(17) Uani 1 1 d . . . . .
O1 O -0.10704(15) -0.0377(3) -0.09420(13) 0.0219(4) Uani 1 1 d . . . . .
N1 N 0.32884(15) -0.1572(4) -0.22714(14) 0.0177(5) Uani 1 1 d . . . . .
H1 H 0.391147 -0.183195 -0.186255 0.021 Uiso 1 1 calc R U . . .
N2 N 0.09587(16) -0.1135(3) -0.10485(14) 0.0168(5) Uani 1 1 d . . . . .
H2A H 0.099057 0.014518 -0.107678 0.020 Uiso 1 1 calc R U . . .
H2B H 0.077034 -0.145087 -0.047673 0.020 Uiso 1 1 calc R U . . .
N3 N -0.18954(16) -0.1810(4) -0.23447(15) 0.0228(5) Uani 1 1 d . . . . .
H3A H -0.255551 -0.151059 -0.227000 0.027 Uiso 1 1 calc R U . . .
H3B H -0.181569 -0.245908 -0.286063 0.027 Uiso 1 1 calc R U . . .
C1 C 0.3168(2) -0.1084(4) -0.32462(18) 0.0179(5) Uani 1 1 d . . . . .
C2 C 0.3954(2) -0.0836(4) -0.3805(2) 0.0216(6) Uani 1 1 d . . . . .
H2 H 0.471228 -0.101407 -0.353195 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3585(2) -0.0318(5) -0.4775(2) 0.0247(6) Uani 1 1 d . . . . .
H3 H 0.409983 -0.015739 -0.517743 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2468(2) -0.0025(4) -0.51762(19) 0.0234(6) Uani 1 1 d . . . . .
H4 H 0.224212 0.034025 -0.584252 0.028 Uiso 1 1 calc R U . . .
C5 C 0.1695(2) -0.0259(4) -0.46217(19) 0.0198(6) Uani 1 1 d . . . . .
H5 H 0.094076 -0.005976 -0.490131 0.024 Uiso 1 1 calc R U . . .
C6 C 0.2034(2) -0.0795(4) -0.36389(18) 0.0164(5) Uani 1 1 d . . . . .
C7 C 0.1484(2) -0.1145(4) -0.28585(17) 0.0167(5) Uani 1 1 d . . . . .
C8 C 0.0283(2) -0.1015(4) -0.28580(17) 0.0169(5) Uani 1 1 d . . . . .
H8A H -0.014841 -0.173012 -0.341886 0.020 Uiso 1 1 calc R U . . .
H8B H 0.004326 0.031761 -0.292356 0.020 Uiso 1 1 calc R U . . .
C9 C 0.00879(17) -0.1836(5) -0.18915(15) 0.0156(5) Uani 1 1 d . . . . .
H9 H 0.013207 -0.324239 -0.191870 0.019 Uiso 1 1 calc R U . . .
C10 C -0.1020(2) -0.1284(4) -0.16792(17) 0.0170(5) Uani 1 1 d . . . . .
C11 C 0.20677(18) -0.1931(5) -0.10527(16) 0.0177(5) Uani 1 1 d . . . . .
H11A H 0.263587 -0.130238 -0.055079 0.021 Uiso 1 1 calc R U . . .
H11B H 0.208480 -0.330008 -0.091177 0.021 Uiso 1 1 calc R U . . .
C12 C 0.22677(18) -0.1581(4) -0.20500(16) 0.0165(5) Uani 1 1 d . . . . .
O2 O 0.500000 0.0769(5) 0.000000 0.0380(8) Uani 1 2 d DGS T P . .
H2C H 0.525660 -0.000758 -0.035471 0.057 Uiso 1 1 d DG U . . .
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'
Cl Cl 0.3639 0.7018 '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
_geom_angle_publ_flag
C1 N1 H1 125.8 . . ?
C12 N1 H1 125.8 . . ?
C12 N1 C1 108.38(18) . . ?
H2A N2 H2B 107.8 . . ?
C9 N2 H2A 109.1 . . ?
C9 N2 H2B 109.1 . . ?
C11 N2 H2A 109.1 . . ?
C11 N2 H2B 109.1 . . ?
C11 N2 C9 112.6(2) . . ?
H3A N3 H3B 120.0 . . ?
C10 N3 H3A 120.0 . . ?
C10 N3 H3B 120.0 . . ?
N1 C1 C2 130.2(2) . . ?
N1 C1 C6 107.7(2) . . ?
C2 C1 C6 122.1(2) . . ?
C1 C2 H2 121.4 . . ?
C3 C2 C1 117.2(2) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.5(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.5 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.2(2) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 106.5(2) . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 134.6(2) . . ?
C6 C7 C8 129.4(2) . . ?
C12 C7 C6 107.2(2) . . ?
C12 C7 C8 123.5(2) . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
C7 C8 C9 109.01(19) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
N2 C9 C8 109.8(2) . . ?
N2 C9 H9 108.8 . . ?
N2 C9 C10 107.1(2) . . ?
C8 C9 H9 108.8 . . ?
C10 C9 C8 113.4(2) . . ?
C10 C9 H9 108.8 . . ?
O1 C10 N3 123.5(2) . . ?
O1 C10 C9 120.8(2) . . ?
N3 C10 C9 115.8(2) . . ?
N2 C11 H11A 110.4 . . ?
N2 C11 H11B 110.4 . . ?
H11A C11 H11B 108.6 . . ?
C12 C11 N2 106.50(19) . . ?
C12 C11 H11A 110.4 . . ?
C12 C11 H11B 110.4 . . ?
N1 C12 C11 124.28(19) . . ?
C7 C12 N1 110.3(2) . . ?
C7 C12 C11 125.4(2) . . ?
H2C O2 H2C 99.1 . 2_655 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.229(3) . ?
N1 H1 0.8800 . ?
N1 C1 1.384(3) . ?
N1 C12 1.377(3) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 C9 1.506(3) . ?
N2 C11 1.498(3) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C10 1.328(3) . ?
C1 C2 1.394(4) . ?
C1 C6 1.419(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.402(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.401(4) . ?
C6 C7 1.433(4) . ?
C7 C8 1.504(3) . ?
C7 C12 1.362(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.540(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.529(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.491(3) . ?
O2 H2C 0.85(5) 2_655 ?
O2 H2C 0.8499 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -179.3(3) . . . . ?
N1 C1 C6 C5 179.2(2) . . . . ?
N1 C1 C6 C7 -0.4(3) . . . . ?
N2 C9 C10 O1 2.1(4) . . . . ?
N2 C9 C10 N3 -179.2(2) . . . . ?
N2 C11 C12 N1 159.6(3) . . . . ?
N2 C11 C12 C7 -17.3(4) . . . . ?
C1 N1 C12 C7 1.1(3) . . . . ?
C1 N1 C12 C11 -176.2(3) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C1 C6 C7 C8 178.9(3) . . . . ?
C1 C6 C7 C12 1.0(3) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
C2 C1 C6 C7 -179.0(3) . . . . ?
C2 C3 C4 C5 -0.6(5) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C4 C5 C6 C7 179.3(3) . . . . ?
C5 C6 C7 C8 -0.6(5) . . . . ?
C5 C6 C7 C12 -178.5(3) . . . . ?
C6 C1 C2 C3 -1.0(4) . . . . ?
C6 C7 C8 C9 171.0(3) . . . . ?
C6 C7 C12 N1 -1.3(3) . . . . ?
C6 C7 C12 C11 176.0(3) . . . . ?
C7 C8 C9 N2 43.9(3) . . . . ?
C7 C8 C9 C10 163.6(2) . . . . ?
C8 C7 C12 N1 -179.3(3) . . . . ?
C8 C7 C12 C11 -2.0(4) . . . . ?
C8 C9 C10 O1 -119.1(3) . . . . ?
C8 C9 C10 N3 59.6(3) . . . . ?
C9 N2 C11 C12 51.7(3) . . . . ?
C11 N2 C9 C8 -68.8(3) . . . . ?
C11 N2 C9 C10 167.7(2) . . . . ?
C12 N1 C1 C2 178.1(3) . . . . ?
C12 N1 C1 C6 -0.4(3) . . . . ?
C12 C7 C8 C9 -11.5(4) . . . . ?
