#------------------------------------------------------------------------------
#$Date: 2022-03-05 00:24:00 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273419 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158493.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_7158493
loop_
_publ_author_name
'Liyu, Jessica'
'Kim, Shi-Wei'
'Söhnel, Tilo'
'Sperry, Jonathan'
_publ_section_title
;
 Progress toward a biomimetic synthesis of pegaharmaline A.
;
_journal_issue                   6
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1275
_journal_page_last               1283
_journal_paper_doi               10.1039/d1ob02372a
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C13 H12 N2 O2'
_chemical_formula_sum            'C13 H12 N2 O2'
_chemical_formula_weight         228.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2021-12-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-12-02 deposited with the CCDC.	2022-01-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.211(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7052(8)
_cell_length_b                   5.0360(2)
_cell_length_c                   13.3544(6)
_cell_measurement_reflns_used    4020
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      75.3350
_cell_measurement_theta_min      5.6320
_cell_volume                     1056.21(8)
_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 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      99.9(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            'Pilatus 200K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00 120.00   0.50    0.27    --   46.98  77.00 -30.00  192
  2  ω    106.00 138.00   0.50    1.06    --  103.64 178.00-180.00   64
  3  ω     60.00  94.00   0.50    1.06    --  103.64 178.00-180.00   68
  4  ω     84.00 173.00   0.50    1.06    --  103.64  45.00  30.00  178
  5  ω     77.00 123.00   0.50    1.06    --  103.64 -61.00  30.00   92
  6  ω     34.00  64.00   0.50    1.06    --  103.64 -61.00  30.00   60
  7  ω    -88.00 -11.00   0.50    1.06    --  -90.25 111.00  30.00  154
  8  ω   -105.00 -15.00   0.50    1.06    --  -90.25  77.00 -90.00  180
  9  ω    -72.00 -16.00   0.50    0.27    --  -46.98  77.00 -90.00  112
 10  ω     27.00  68.00   0.50    1.06    --  103.64 -15.00 150.00   82
 11  ω     86.00 113.00   0.50    1.06    --  103.64-111.00 150.00   54
 12  ω     35.00 112.00   0.50    1.06    --  103.64-111.00   0.00  154
 13  ω     46.00 103.00   0.50    1.06    --  103.64 -95.00   0.00  114
 14  ω     69.00 104.00   0.50    1.06    --  103.64-111.00 -60.00   70
 15  ω     32.00  58.00   0.50    1.06    --  103.64-111.00-180.00   52
 16  ω     73.00 111.00   0.50    1.06    --  103.64-111.00-180.00   76
 17  ω     42.00  68.00   0.50    0.27    --   46.98-125.00 -90.00   52
 18  ω     42.00  98.00   0.50    0.27    --   46.98-125.00  60.00  112
 19  ω     87.00 131.00   0.50    1.06    --  103.64 -15.00 150.00   88
 20  ω   -103.00 -22.00   0.50    0.27    --  -46.98 -77.00  60.00  162
 21  ω   -159.00 -70.00   0.50    1.06    --  -90.25 -61.00 150.00  178
 22  ω   -158.00-109.00   0.50    1.06    --  -90.25 -45.00 -30.00   98
 23  ω   -155.00-128.00   0.50    1.06    --  -90.25 -45.00-150.00   54
 24  ω   -158.00 -70.00   0.50    1.06    --  -90.25 -61.00-180.00  176
 25  ω   -106.00 -79.00   0.50    1.06    --  -90.25 -45.00-150.00   54
 26  ω     38.00  63.00   0.50    1.06    --  103.64-111.00 -90.00   50
 27  ω     64.00  90.00   0.50    1.06    --  103.64 -95.00 -60.00   52
 28  ω     30.00  60.00   0.50    1.06    --  103.64-111.00 150.00   60
;
_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      0.0235429000
_diffrn_orient_matrix_UB_12      -0.2349835000
_diffrn_orient_matrix_UB_13      0.0685224000
_diffrn_orient_matrix_UB_21      -0.0856472000
_diffrn_orient_matrix_UB_22      -0.1339949000
_diffrn_orient_matrix_UB_23      -0.0252539000
_diffrn_orient_matrix_UB_31      0.0417670000
_diffrn_orient_matrix_UB_32      -0.1425481000
_diffrn_orient_matrix_UB_33      -0.0892805000
_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  0.0308
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8761
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.718
_diffrn_reflns_theta_min         5.634
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77944
_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_density_diffrn    1.435
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1894
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0544
_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)+(0.0910P)²+0.8516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1545
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1785
_reflns_number_total             1894
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02372a2.cif
_cod_data_source_block           jl3_12b
_cod_depositor_comments
'Adding full bibliography for 7158492--7158494.cif.'
_cod_database_code               7158493
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C13H12N2O2
_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   0.924
_shelx_estimated_absorpt_t_min   0.882
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.62
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_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 1.354
_oxdiff_exptl_absorpt_empirical_full_min 0.755
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C 0.68477(12) 0.5388(4) 0.30516(14) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.65537(12) 0.7277(4) 0.23672(15) 0.0260(5) Uani 1 1 d . . . . .
H2 H 0.679996 0.737839 0.173614 0.031 Uiso 1 1 calc R U . . .
C3 C 0.59049(13) 0.8991(4) 0.26133(15) 0.0268(5) Uani 1 1 d . . . . .
H3 H 0.572273 1.025167 0.215113 0.032 Uiso 1 1 calc R U . . .
C4 C 0.55157(12) 0.8850(4) 0.35567(15) 0.0277(5) Uani 1 1 d . . . . .
H4 H 0.507234 0.999761 0.371557 0.033 Uiso 1 1 calc R U . . .
C5 C 0.57929(12) 0.7011(4) 0.42439(14) 0.0255(5) Uani 1 1 d . . . . .
H5 H 0.553725 0.692117 0.487004 0.031 Uiso 1 1 calc R U . . .
C6 C 0.64576(12) 0.5269(4) 0.40080(14) 0.0233(4) Uani 1 1 d . . . . .
C7 C 0.67610(12) 0.3358(4) 0.47513(14) 0.0248(5) Uani 1 1 d . . . . .
C8 C 0.79188(12) -0.0020(4) 0.50324(14) 0.0246(5) Uani 1 1 d . . . . .
H8 H 0.753611 -0.145573 0.523821 0.030 Uiso 1 1 calc R U . . .
C9 C 0.85694(12) -0.1034(4) 0.42902(14) 0.0249(5) Uani 1 1 d . . . . .
C10 C 0.92046(13) -0.3051(4) 0.46233(15) 0.0302(5) Uani 1 1 d . . . . .
H10A H 0.953995 -0.360515 0.406122 0.045 Uiso 1 1 calc R U . . .
H10B H 0.891307 -0.455760 0.489847 0.045 Uiso 1 1 calc R U . . .
H10C H 0.956982 -0.228937 0.512465 0.045 Uiso 1 1 calc R U . . .
C11 C 0.84785(12) 0.0150(4) 0.34001(14) 0.0243(5) Uani 1 1 d . . . . .
C12 C 0.89596(13) -0.0329(5) 0.24533(15) 0.0311(5) Uani 1 1 d . . . . .
H12A H 0.945968 -0.135843 0.259739 0.047 Uiso 1 1 calc R U . . .
H12B H 0.912339 0.134213 0.216639 0.047 Uiso 1 1 calc R U . . .
H12C H 0.860487 -0.127668 0.198828 0.047 Uiso 1 1 calc R U . . .
C13 C 0.77842(12) 0.2095(4) 0.34620(14) 0.0225(4) Uani 1 1 d . . . . .
N1 N 0.75147(10) 0.3697(3) 0.27751(12) 0.0235(4) Uani 1 1 d . . . . .
N2 N 0.74592(10) 0.1941(3) 0.44246(11) 0.0237(4) Uani 1 1 d . . . . .
O1 O 0.64692(9) 0.3008(3) 0.55925(10) 0.0301(4) Uani 1 1 d . . . . .
O2 O 0.83228(9) 0.1086(3) 0.58613(10) 0.0271(4) Uani 1 1 d . . . . .
H2A H 0.799448 0.109723 0.633733 0.041 Uiso 1 1 calc R 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'
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
C2 C1 C6 118.34(18) . . ?
C2 C1 N1 119.17(17) . . ?
N1 C1 C6 122.49(18) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.95(18) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.53(19) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.70(19) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.45(18) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C7 119.88(18) . . ?
C5 C6 C1 120.03(18) . . ?
C5 C6 C7 120.08(17) . . ?
N2 C7 C6 112.54(16) . . ?
O1 C7 C6 126.47(18) . . ?
O1 C7 N2 120.97(18) . . ?
C9 C8 H8 110.5 . . ?
N2 C8 H8 110.5 . . ?
N2 C8 C9 101.33(15) . . ?
O2 C8 H8 110.5 . . ?
O2 C8 C9 110.43(15) . . ?
O2 C8 N2 113.13(16) . . ?
C10 C9 C8 119.12(17) . . ?
C11 C9 C8 111.20(18) . . ?
C11 C9 C10 129.67(18) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 C12 128.86(19) . . ?
C9 C11 C13 108.92(17) . . ?
C13 C11 C12 122.20(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N1 C13 C11 128.18(17) . . ?
N1 C13 N2 124.92(18) . . ?
N2 C13 C11 106.89(16) . . ?
C13 N1 C1 115.84(16) . . ?
C7 N2 C8 124.27(16) . . ?
C7 N2 C13 124.01(17) . . ?
C13 N2 C8 111.63(16) . . ?
C8 O2 H2A 109.5 . . ?
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
C1 C2 1.397(3) . ?
C1 C6 1.420(3) . ?
C1 N1 1.401(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.376(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.404(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.374(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.400(3) . ?
C6 C7 1.461(3) . ?
C7 N2 1.380(3) . ?
C7 O1 1.228(2) . ?
C8 H8 0.9800 . ?
C8 C9 1.515(3) . ?
C8 N2 1.467(3) . ?
C8 O2 1.391(2) . ?
C9 C10 1.491(3) . ?
C9 C11 1.337(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.495(3) . ?
C11 C13 1.468(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 N1 1.292(3) . ?
C13 N2 1.387(2) . ?
O2 H2A 0.8200 . ?
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
C1 C2 C3 C4 -0.9(3) . . . . ?
C1 C6 C7 N2 3.6(3) . . . . ?
C1 C6 C7 O1 -178.19(19) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C1 C6 C7 -178.64(18) . . . . ?
C2 C1 N1 C13 176.48(18) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C4 C5 C6 C7 178.64(18) . . . . ?
C5 C6 C7 N2 -175.30(17) . . . . ?
C5 C6 C7 O1 2.9(3) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C1 N1 C13 -3.2(3) . . . . ?
C6 C7 N2 C8 177.10(17) . . . . ?
C6 C7 N2 C13 -6.5(3) . . . . ?
C8 C9 C11 C12 -177.4(2) . . . . ?
C8 C9 C11 C13 1.5(2) . . . . ?
C9 C8 N2 C7 176.63(17) . . . . ?
C9 C8 N2 C13 -0.1(2) . . . . ?
C9 C11 C13 N1 177.77(19) . . . . ?
C9 C11 C13 N2 -1.5(2) . . . . ?
C10 C9 C11 C12 4.1(4) . . . . ?
C10 C9 C11 C13 -177.1(2) . . . . ?
C11 C13 N1 C1 -178.73(18) . . . . ?
C11 C13 N2 C7 -175.80(17) . . . . ?
C11 C13 N2 C8 1.0(2) . . . . ?
C12 C11 C13 N1 -3.3(3) . . . . ?
C12 C11 C13 N2 177.43(18) . . . . ?
N1 C1 C2 C3 -179.41(18) . . . . ?
N1 C1 C6 C5 179.98(17) . . . . ?
N1 C1 C6 C7 1.0(3) . . . . ?
N1 C13 N2 C7 4.9(3) . . . . ?
N1 C13 N2 C8 -178.35(18) . . . . ?
N2 C8 C9 C10 177.87(17) . . . . ?
N2 C8 C9 C11 -0.9(2) . . . . ?
N2 C13 N1 C1 0.4(3) . . . . ?
O1 C7 N2 C8 -1.2(3) . . . . ?
O1 C7 N2 C13 175.19(18) . . . . ?
O2 C8 C9 C10 57.7(2) . . . . ?
O2 C8 C9 C11 -120.99(19) . . . . ?
O2 C8 N2 C7 -65.2(2) . . . . ?
O2 C8 N2 C13 118.06(17) . . . . ?
