# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jg153_1_100_00
_database_code_depnum_ccdc_archive 'CCDC 2109112'
loop_
_audit_author_name
_audit_author_address
'Nathan Halcovitch'
;Lancaster University
United Kingdom
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 N2 O'
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 N2 O1'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.5535(2)
_cell_length_b                   12.2303(2)
_cell_length_c                   7.24910(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1112.98(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6882
_cell_measurement_temperature    99.97(11)
_cell_measurement_theta_max      75.9280
_cell_measurement_theta_min      5.0370
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.937
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0123
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8485
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.186
_diffrn_reflns_theta_min         5.049
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00    2.00    --  -42.28 125.00  30.00   81
  2  ω   -112.00 -16.00   1.00    2.00    --  -42.28 -57.00 120.00   96
  3  ω    -69.00  28.00   1.00    2.00    --  -42.28  57.00 -90.00   97
  4  ω     61.00 146.00   1.00    8.00    --  111.00 178.00 150.00   85
  5  ω    103.00 178.00   1.00    8.00    --  111.00  77.00  90.00   75
  6  ω     87.00 178.00   1.00    8.00    --  111.00  45.00 -30.00   91
  7  ω     40.00 135.00   1.00    8.00    --  111.00 -45.00  60.00   95
  8  ω    104.00 178.00   1.00    8.00    --  111.00 111.00 120.00   74
  9  ω     61.00 146.00   1.00    8.00    --  111.00 178.00 120.00   85
 10  ω     83.00 178.00   1.00    8.00    --  111.00  61.00-120.00   95
 11  ω     87.00 178.00   1.00    8.00    --  111.00  30.00 -60.00   91
 12  ω    103.00 178.00   1.00    8.00    --  111.00  77.00-180.00   75
 13  ω   -112.00 -16.00   1.00    2.00    --  -42.28 -57.00   0.00   96
 14  ω   -115.00 -20.00   1.00    2.00    --  -42.28 -38.00 150.00   95
 15  ω   -112.00 -16.00   1.00    2.00    --  -42.28 -57.00-120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0416387000
_diffrn_orient_matrix_UB_12      -0.0773762000
_diffrn_orient_matrix_UB_13      0.1092198000
_diffrn_orient_matrix_UB_21      -0.0749983000
_diffrn_orient_matrix_UB_22      0.1672671000
_diffrn_orient_matrix_UB_23      0.0114912000
_diffrn_orient_matrix_UB_31      -0.0877697000
_diffrn_orient_matrix_UB_32      -0.1059367000
_diffrn_orient_matrix_UB_33      -0.0616022000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_full    0.960
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                2202
_reflns_number_total             2235
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.103
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 957 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(6)
_refine_ls_extinction_coef       0.0033(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2235
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0256
_refine_ls_restrained_S_all      1.057
_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)+(0.0402P)²+0.0998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0697
_refine_special_details          ?
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O3 O 0.27491(8) 0.89136(8) 0.53953(14) 0.0331(3) Uani 1 1 d . . . . .
N1 N 0.35270(9) 0.44676(10) 0.45578(16) 0.0290(3) Uani 1 1 d . . . . .
N2 N 0.43501(8) 0.41056(9) 0.53284(15) 0.0272(3) Uani 1 1 d . . . . .
C1 C 0.33520(10) 0.56048(12) 0.48235(18) 0.0267(3) Uani 1 1 d . . . . .
C2 C 0.24787(11) 0.60497(12) 0.39072(18) 0.0296(3) Uani 1 1 d . . . . .
H2 H 0.2042 0.5593 0.3165 0.035 Uiso 1 1 calc R U . . .
C3 C 0.22396(10) 0.71555(12) 0.40671(19) 0.0292(3) Uani 1 1 d . . . . .
H3 H 0.1639 0.7454 0.3448 0.035 Uiso 1 1 calc R U . . .
C4 C 0.28896(10) 0.78206(11) 0.51441(17) 0.0271(3) Uani 1 1 d . . . . .
C5 C 0.37611(10) 0.73741(12) 0.60847(18) 0.0295(3) Uani 1 1 d . . . . .
H5 H 0.4199 0.7831 0.6825 0.035 Uiso 1 1 calc R U . . .
C6 C 0.39851(10) 0.62779(12) 0.59417(18) 0.0287(3) Uani 1 1 d . . . . .
H6 H 0.4569 0.5976 0.6601 0.034 Uiso 1 1 calc R U . . .
C7 C 0.45033(10) 0.29567(11) 0.50955(17) 0.0267(3) Uani 1 1 d . . . . .
C8 C 0.53931(10) 0.25230(12) 0.59646(19) 0.0302(3) Uani 1 1 d . . . . .
H8 H 0.5855 0.2986 0.6648 0.036 Uiso 1 1 calc R U . . .
C9 C 0.56085(12) 0.14081(12) 0.5834(2) 0.0362(3) Uani 1 1 d . . . . .
H9 H 0.6218 0.1111 0.6427 0.043 Uiso 1 1 calc R U . . .
C10 C 0.49326(13) 0.07320(13) 0.4837(2) 0.0373(3) Uani 1 1 d . . . . .
H10 H 0.5075 -0.0029 0.4752 0.045 Uiso 1 1 calc R U . . .
C11 C 0.40448(13) 0.11741(13) 0.3961(2) 0.0363(3) Uani 1 1 d . . . . .
H11 H 0.3588 0.0711 0.3268 0.044 Uiso 1 1 calc R U . . .
C12 C 0.38197(11) 0.22783(12) 0.40875(19) 0.0312(3) Uani 1 1 d . . . . .
H12 H 0.3208 0.2573 0.3497 0.037 Uiso 1 1 calc R U . . .
C13 C 0.17977(12) 0.93911(13) 0.4706(2) 0.0391(4) Uani 1 1 d . . . . .
H13A H 0.1804 0.9368 0.3355 0.059 Uiso 1 1 calc R U . . .
H13B H 0.1751 1.0152 0.5120 0.059 Uiso 1 1 calc R U . . .
H13C H 0.1182 0.8982 0.5168 0.059 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O3 C4 1.3606(16) . ?
O3 C13 1.4203(17) . ?
N1 N2 1.2553(15) . ?
N1 C1 1.4211(16) . ?
N2 C7 1.4283(16) . ?
C1 C2 1.3926(18) . ?
C1 C6 1.4023(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.3918(19) . ?
C4 C5 1.4000(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.374(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3878(18) . ?
C7 C12 1.3995(18) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(2) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C4 O3 C13 117.76(11) . . ?
N2 N1 C1 114.33(11) . . ?
N1 N2 C7 113.90(11) . . ?
C2 C1 N1 116.07(12) . . ?
C2 C1 C6 119.50(13) . . ?
C6 C1 N1 124.42(12) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.69(12) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.26(12) . . ?
C4 C3 H3 120.4 . . ?
O3 C4 C3 124.98(12) . . ?
O3 C4 C5 114.79(12) . . ?
C3 C4 C5 120.22(12) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.26(12) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.03(12) . . ?
C5 C6 H6 120.0 . . ?
C8 C7 N2 115.52(12) . . ?
C8 C7 C12 120.26(13) . . ?
C12 C7 N2 124.22(12) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.96(13) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.99(14) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.71(14) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.85(14) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 120.4 . . ?
C11 C12 C7 119.23(14) . . ?
C11 C12 H12 120.4 . . ?
O3 C13 H13A 109.5 . . ?
O3 C13 H13B 109.5 . . ?
O3 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O3 C4 C5 C6 179.93(12) . . . . ?
N1 N2 C7 C8 -178.60(12) . . . . ?
N1 N2 C7 C12 0.82(17) . . . . ?
N1 C1 C2 C3 -179.70(12) . . . . ?
N1 C1 C6 C5 178.88(12) . . . . ?
N2 N1 C1 C2 176.62(11) . . . . ?
N2 N1 C1 C6 -4.15(18) . . . . ?
N2 C7 C8 C9 179.49(12) . . . . ?
N2 C7 C12 C11 -179.72(13) . . . . ?
C1 N1 N2 C7 178.38(10) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C2 C1 C6 C5 -1.92(19) . . . . ?
C2 C3 C4 O3 179.25(12) . . . . ?
C2 C3 C4 C5 -1.31(19) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C1 1.2(2) . . . . ?
C6 C1 C2 C3 1.04(19) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C7 C12 C11 -0.3(2) . . . . ?
C8 C9 C10 C11 0.4(2) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C10 C11 C12 C7 0.7(2) . . . . ?
C12 C7 C8 C9 0.0(2) . . . . ?
C13 O3 C4 C3 8.42(19) . . . . ?
C13 O3 C4 C5 -171.05(12) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Mitegen loop'
_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 1.367
_oxdiff_exptl_absorpt_empirical_full_min 0.703
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jg153_3_180_00
_database_code_depnum_ccdc_archive 'CCDC 2109114'
loop_
_audit_author_name
_audit_author_address
'Nathan Halcovitch'
;Lancaster University
United Kingdom
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 N2 O'
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 N2 O1'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.5855(2)
_cell_length_b                   12.2723(2)
_cell_length_c                   7.31060(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1129.14(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6623
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      75.9810
_cell_measurement_theta_min      5.0220
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8694
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.243
_diffrn_reflns_theta_min         5.034
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00    3.00    --  -42.28 125.00  30.00   81
  2  ω   -112.00 -16.00   1.00    3.00    --  -42.28 -57.00 120.00   96
  3  ω    -69.00  28.00   1.00    3.00    --  -42.28  57.00 -90.00   97
  4  ω     61.00 146.00   1.00   12.00    --  111.00 178.00 150.00   85
  5  ω    103.00 178.00   1.00   12.00    --  111.00  77.00  90.00   75
  6  ω     87.00 178.00   1.00   12.00    --  111.00  45.00 -30.00   91
  7  ω     40.00 135.00   1.00   12.00    --  111.00 -45.00  60.00   95
  8  ω    104.00 178.00   1.00   12.00    --  111.00 111.00 120.00   74
  9  ω     61.00 146.00   1.00   12.00    --  111.00 178.00 120.00   85
 10  ω     83.00 178.00   1.00   12.00    --  111.00  61.00-120.00   95
 11  ω     87.00 178.00   1.00   12.00    --  111.00  30.00 -60.00   91
 12  ω    103.00 178.00   1.00   12.00    --  111.00  77.00-180.00   75
 13  ω   -112.00 -16.00   1.00    3.00    --  -42.28 -57.00   0.00   96
 14  ω   -115.00 -20.00   1.00    3.00    --  -42.28 -38.00 150.00   95
 15  ω   -112.00 -16.00   1.00    3.00    --  -42.28 -57.00-120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0410145000
_diffrn_orient_matrix_UB_12      -0.0780441000
_diffrn_orient_matrix_UB_13      -0.1087926000
_diffrn_orient_matrix_UB_21      0.0747856000
_diffrn_orient_matrix_UB_22      0.1654366000
_diffrn_orient_matrix_UB_23      -0.0125131000
_diffrn_orient_matrix_UB_31      0.0877119000
_diffrn_orient_matrix_UB_32      -0.1047366000
_diffrn_orient_matrix_UB_33      0.0614289000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.931
_reflns_number_gt                2210
_reflns_number_total             2271
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.023
_refine_ls_abs_structure_details 
;
 Flack x determined using 966 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(7)
_refine_ls_extinction_coef       0.0093(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2271
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0269
_refine_ls_restrained_S_all      1.085
_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)+(0.0438P)²+0.0730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0777
_refine_special_details          ?
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.27321(9) 0.88868(9) 0.53843(16) 0.0515(3) Uani 1 1 d . . . . .
N1 N 0.35311(10) 0.44622(11) 0.45724(17) 0.0435(3) Uani 1 1 d . . . . .
N2 N 0.43490(9) 0.41044(10) 0.53299(16) 0.0412(3) Uani 1 1 d . . . . .
C1 C 0.33514(11) 0.55945(13) 0.48298(19) 0.0398(3) Uani 1 1 d . . . . .
C2 C 0.24838(12) 0.60330(14) 0.3916(2) 0.0452(4) Uani 1 1 d . . . . .
H2 H 0.2052 0.5575 0.3177 0.054 Uiso 1 1 calc R U . . .
C3 C 0.22397(11) 0.71318(13) 0.4069(2) 0.0448(4) Uani 1 1 d . . . . .
H3 H 0.1641 0.7425 0.3448 0.054 Uiso 1 1 calc R U . . .
C4 C 0.28786(11) 0.77994(13) 0.51400(18) 0.0410(3) Uani 1 1 d . . . . .
C5 C 0.37462(11) 0.73577(14) 0.6078(2) 0.0449(4) Uani 1 1 d . . . . .
H5 H 0.4178 0.7815 0.6818 0.054 Uiso 1 1 calc R U . . .
C6 C 0.39773(11) 0.62698(13) 0.5937(2) 0.0430(3) Uani 1 1 d . . . . .
H6 H 0.4562 0.5973 0.6590 0.052 Uiso 1 1 calc R U . . .
C7 C 0.45043(11) 0.29602(12) 0.51019(18) 0.0396(3) Uani 1 1 d . . . . .
C8 C 0.53892(12) 0.25286(13) 0.5958(2) 0.0472(4) Uani 1 1 d . . . . .
H8 H 0.5851 0.2990 0.6633 0.057 Uiso 1 1 calc R U . . .
C9 C 0.56028(15) 0.14202(14) 0.5832(3) 0.0576(4) Uani 1 1 d . . . . .
H9 H 0.6210 0.1124 0.6421 0.069 Uiso 1 1 calc R U . . .
C10 C 0.49300(16) 0.07490(15) 0.4848(3) 0.0591(4) Uani 1 1 d . . . . .
H10 H 0.5073 -0.0010 0.4766 0.071 Uiso 1 1 calc R U . . .
C11 C 0.40500(15) 0.11834(15) 0.3985(3) 0.0572(4) Uani 1 1 d . . . . .
H11 H 0.3595 0.0721 0.3298 0.069 Uiso 1 1 calc R U . . .
C12 C 0.38244(13) 0.22827(14) 0.4108(2) 0.0476(4) Uani 1 1 d . . . . .
H12 H 0.3213 0.2575 0.3524 0.057 Uiso 1 1 calc R U . . .
C13 C 0.17892(15) 0.93619(16) 0.4699(3) 0.0617(5) Uani 1 1 d . . . . .
H13A H 0.1793 0.9331 0.3360 0.093 Uiso 1 1 calc R U . . .
H13B H 0.1748 1.0124 0.5096 0.093 Uiso 1 1 calc R U . . .
H13C H 0.1173 0.8961 0.5167 0.093 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C4 1.3589(18) . ?
O1 C13 1.414(2) . ?
N1 N2 1.2487(17) . ?
N1 C1 1.4204(18) . ?
N2 C7 1.4275(18) . ?
C1 C2 1.389(2) . ?
C1 C6 1.401(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
C4 C5 1.3986(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.370(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(2) . ?
C7 C12 1.397(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.390(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C4 O1 C13 118.19(13) . . ?
N2 N1 C1 114.62(12) . . ?
N1 N2 C7 114.02(12) . . ?
C2 C1 N1 116.14(13) . . ?
C2 C1 C6 119.40(14) . . ?
C6 C1 N1 124.46(13) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.78(14) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.37(13) . . ?
C4 C3 H3 120.3 . . ?
O1 C4 C3 125.07(13) . . ?
O1 C4 C5 114.97(13) . . ?
C3 C4 C5 119.97(14) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.42(13) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.04(13) . . ?
C5 C6 H6 120.0 . . ?
C8 C7 N2 115.73(13) . . ?
C8 C7 C12 120.05(14) . . ?
C12 C7 N2 124.22(13) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.04(15) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 119.94(17) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.90(17) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.77(16) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 120.4 . . ?
C11 C12 C7 119.29(16) . . ?
C11 C12 H12 120.4 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O1 C4 C5 C6 -179.85(13) . . . . ?
N1 N2 C7 C8 -178.53(13) . . . . ?
N1 N2 C7 C12 0.82(18) . . . . ?
N1 C1 C2 C3 -179.79(13) . . . . ?
N1 C1 C6 C5 179.18(14) . . . . ?
N2 N1 C1 C2 176.28(13) . . . . ?
N2 N1 C1 C6 -4.37(19) . . . . ?
N2 C7 C8 C9 179.35(15) . . . . ?
N2 C7 C12 C11 -179.70(15) . . . . ?
C1 N1 N2 C7 178.38(11) . . . . ?
C1 C2 C3 C4 0.5(2) . . . . ?
C2 C1 C6 C5 -1.5(2) . . . . ?
C2 C3 C4 O1 179.24(14) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C7 C12 C11 -0.4(2) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 -0.8(3) . . . . ?
C10 C11 C12 C7 0.8(3) . . . . ?
C12 C7 C8 C9 0.0(2) . . . . ?
C13 O1 C4 C3 8.5(2) . . . . ?
C13 O1 C4 C5 -171.06(15) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Mitegen loop'
_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 1.319
_oxdiff_exptl_absorpt_empirical_full_min 0.699
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jg154_5_260_00
_database_code_depnum_ccdc_archive 'CCDC 2109122'
loop_
_audit_author_name
_audit_author_address
'Nathan Halcovitch'
;Lancaster University
United Kingdom
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12.884 H11.651 N2 O0.882'
_chemical_formula_sum            'C12.89 H11.67 N2 O0.88'
_chemical_formula_weight         208.71
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 N2 O1'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.4470(3)
_cell_length_b                   12.3034(3)
_cell_length_c                   7.4227(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1136.72(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4240
_cell_measurement_temperature    260.00(10)
_cell_measurement_theta_max      75.4990
_cell_measurement_theta_min      5.0310
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.627
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_unetI/netI     0.0073
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8785
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.153
_diffrn_reflns_theta_min         5.055
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      260.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  28.00   1.00    3.00    --  -42.28  57.00  30.00   97
  2  ω   -112.00 -16.00   1.00    3.00    --  -42.28 -57.00-120.00   96
  3  ω    -87.00  -6.00   1.00    3.00    --  -42.28 125.00  60.00   81
  4  ω     36.00 109.00   1.00   12.00    --  111.00-111.00 -30.00   73
  5  ω    103.00 178.00   1.00   12.00    --  111.00  77.00 -60.00   75
  6  ω     41.00 139.00   1.00   12.00    --  111.00 -61.00 -60.00   98
  7  ω    103.00 178.00   1.00   12.00    --  111.00  77.00-150.00   75
  8  ω    103.00 178.00   1.00   12.00    --  111.00  77.00 -30.00   75
  9  ω    103.00 178.00   1.00   12.00    --  111.00  77.00-120.00   75
 10  ω    103.00 178.00   1.00   12.00    --  111.00  77.00  90.00   75
 11  ω     30.00 107.00   1.00   12.00    --  111.00 -94.00 150.00   77
 12  ω    103.00 178.00   1.00   12.00    --  111.00  77.00 150.00   75
 13  ω   -112.00 -16.00   1.00    3.00    --  -42.28 -57.00  60.00   96
 14  ω   -112.00 -16.00   1.00    3.00    --  -42.28 -57.00 -30.00   96
 15  ω     87.00 178.00   1.00   12.00    --  111.00  30.00  60.00   91
 16  ω     66.00 124.00   1.00   12.00    --  111.00  15.00-150.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0393935000
_diffrn_orient_matrix_UB_12      -0.0933886000
_diffrn_orient_matrix_UB_13      -0.1044611000
_diffrn_orient_matrix_UB_21      0.0512166000
_diffrn_orient_matrix_UB_22      -0.1780260000
_diffrn_orient_matrix_UB_23      0.0381635000
_diffrn_orient_matrix_UB_31      -0.1055527000
_diffrn_orient_matrix_UB_32      -0.0514808000
_diffrn_orient_matrix_UB_33      0.0575885000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.830
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                2066
_reflns_number_total             2330
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.087
_refine_diff_density_rms         0.022
_refine_ls_abs_structure_details 
;
 Flack x determined using 879 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2330
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.054
_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)+(0.0631P)²+0.0632P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1173
_refine_special_details          ?
_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
2. Others
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.27259(17) 0.11412(18) 0.4632(3) 0.0886(8) Uani 0.882(6) 1 d . . . . .
N1 N 0.35241(17) 0.55384(18) 0.5398(3) 0.0782(6) Uani 1 1 d . . . . .
N2 N 0.43373(15) 0.58889(17) 0.4669(2) 0.0752(5) Uani 1 1 d . . . . .
C1 C 0.33456(18) 0.4403(2) 0.5157(3) 0.0708(6) Uani 1 1 d . . . . .
C2 C 0.2470(2) 0.3973(2) 0.6051(3) 0.0797(6) Uani 1 1 d . . . . .
H2 H 0.2044 0.4423 0.6760 0.096 Uiso 1 1 calc R U . . .
C3 C 0.22211(19) 0.2886(2) 0.5906(3) 0.0805(7) Uani 1 1 d . . . . .
H3 H 0.1625 0.2605 0.6501 0.097 Uiso 1 1 calc R U . . .
C4 C 0.2870(2) 0.2210(2) 0.4861(3) 0.0761(6) Uani 1 1 d . . . . .
C5 C 0.3739(2) 0.2650(2) 0.3956(3) 0.0854(7) Uani 1 1 d . . . . .
H5 H 0.4170 0.2203 0.3250 0.102 Uiso 1 1 calc R U . . .
C6 C 0.3971(2) 0.3721(2) 0.4083(3) 0.0821(7) Uani 1 1 d . . . . .
H6 H 0.4551 0.4005 0.3449 0.098 Uiso 1 1 calc R U . . .
C7 C 0.44919(18) 0.70334(19) 0.4894(3) 0.0707(5) Uani 1 1 d . . . . .
C8 C 0.5390(2) 0.7468(2) 0.4081(3) 0.0826(7) Uani 1 1 d . . . . .
H8 H 0.5858 0.7016 0.3453 0.099 Uiso 1 1 calc R U . . .
C9 C 0.5601(3) 0.8562(2) 0.4192(5) 0.0988(8) Uani 1 1 d . . . . .
H9 H 0.6206 0.8848 0.3630 0.119 Uiso 1 1 calc R U . . .
C10 C 0.4925(3) 0.9230(2) 0.5124(6) 0.1001(9) Uani 1 1 d . . . . .
H10 H 0.5068 0.9971 0.5199 0.120 Uiso 1 1 calc R U . . .
C11 C 0.4031(3) 0.8803(3) 0.5950(4) 0.0980(8) Uani 1 1 d . . . . .
H11 H 0.3574 0.9260 0.6589 0.118 Uiso 1 1 calc R U . . .
C12 C 0.3803(2) 0.7716(2) 0.5847(3) 0.0843(7) Uani 1 1 d . . . . .
H12 H 0.3194 0.7437 0.6407 0.101 Uiso 1 1 calc R U . . .
C13 C 0.1777(3) 0.0670(3) 0.5277(6) 0.1026(13) Uani 0.884(8) 1 d . . P . .
H13A H 0.1170 0.1069 0.4829 0.154 Uiso 0.884(8) 1 calc R U P . .
H13B H 0.1776 0.0688 0.6570 0.154 Uiso 0.884(8) 1 calc R U P . .
H13C H 0.1734 -0.0070 0.4874 0.154 Uiso 0.884(8) 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C4 1.338(3) . ?
O1 C13 1.400(4) . ?
N1 N2 1.226(3) . ?
N1 C1 1.426(3) . ?
N2 C7 1.431(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.395(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(4) . ?
C4 C5 1.384(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.351(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(3) . ?
C7 C12 1.393(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.374(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.365(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.374(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(4) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C4 O1 C13 118.5(2) . . ?
N2 N1 C1 114.69(19) . . ?
N1 N2 C7 113.9(2) . . ?
C2 C1 N1 115.9(2) . . ?
C2 C1 C6 119.0(2) . . ?
C6 C1 N1 125.1(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
O1 C4 C3 125.4(2) . . ?
O1 C4 C5 115.3(2) . . ?
C5 C4 C3 119.3(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 H6 119.8 . . ?
C8 C7 N2 116.1(2) . . ?
C8 C7 C12 119.2(2) . . ?
C12 C7 N2 124.7(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.6(2) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
C7 C12 H12 120.4 . . ?
C11 C12 C7 119.3(3) . . ?
C11 C12 H12 120.4 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O1 C4 C5 C6 -179.9(2) . . . . ?
N1 N2 C7 C8 -179.4(2) . . . . ?
N1 N2 C7 C12 0.1(3) . . . . ?
N1 C1 C2 C3 179.7(2) . . . . ?
N1 C1 C6 C5 179.4(2) . . . . ?
N2 N1 C1 C2 176.3(2) . . . . ?
N2 N1 C1 C6 -4.7(3) . . . . ?
N2 C7 C8 C9 178.9(2) . . . . ?
N2 C7 C12 C11 -179.3(2) . . . . ?
C1 N1 N2 C7 178.79(17) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C1 C6 C5 -1.7(4) . . . . ?
C2 C3 C4 O1 179.0(2) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 1.1(4) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C7 C8 C9 C10 0.6(5) . . . . ?
C8 C7 C12 C11 0.2(4) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
C10 C11 C12 C7 0.3(5) . . . . ?
C12 C7 C8 C9 -0.7(4) . . . . ?
C13 O1 C4 C3 9.2(4) . . . . ?
C13 O1 C4 C5 -170.5(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Mitegen loop'
_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 1.135
_oxdiff_exptl_absorpt_empirical_full_min 0.858
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jg154_4_220_00
_database_code_depnum_ccdc_archive 'CCDC 2109121'
loop_
_audit_author_name
_audit_author_address
'Nathan Halcovitch'
;Lancaster University
United Kingdom
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12.868 H11.604 N2 O0.878'
_chemical_formula_sum            'C12.87 H11.61 N2 O0.88'
_chemical_formula_weight         208.30
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 N2 O1'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.4276(3)
_cell_length_b                   12.2735(2)
_cell_length_c                   7.37630(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1125.11(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4934
_cell_measurement_temperature    220.01(10)
_cell_measurement_theta_max      75.3170
_cell_measurement_theta_min      5.0540
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             439
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0122
_diffrn_reflns_av_unetI/netI     0.0085
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8657
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.815
_diffrn_reflns_theta_min         5.065
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  28.00   1.00    3.00    --  -42.28  57.00  30.00   97
  2  ω   -112.00 -16.00   1.00    3.00    --  -42.28 -57.00-120.00   96
  3  ω    -87.00  -6.00   1.00    3.00    --  -42.28 125.00  60.00   81
  4  ω     36.00 109.00   1.00   12.00    --  111.00-111.00 -30.00   73
  5  ω    103.00 178.00   1.00   12.00    --  111.00  77.00 -60.00   75
  6  ω     41.00 139.00   1.00   12.00    --  111.00 -61.00 -60.00   98
  7  ω    103.00 178.00   1.00   12.00    --  111.00  77.00-150.00   75
  8  ω    103.00 178.00   1.00   12.00    --  111.00  77.00 -30.00   75
  9  ω    103.00 178.00   1.00   12.00    --  111.00  77.00-120.00   75
 10  ω    103.00 178.00   1.00   12.00    --  111.00  77.00  90.00   75
 11  ω     30.00 107.00   1.00   12.00    --  111.00 -94.00 150.00   77
 12  ω    103.00 178.00   1.00   12.00    --  111.00  77.00 150.00   75
 13  ω   -112.00 -16.00   1.00    3.00    --  -42.28 -57.00  60.00   96
 14  ω   -112.00 -16.00   1.00    3.00    --  -42.28 -57.00 -30.00   96
 15  ω     87.00 178.00   1.00   12.00    --  111.00  30.00  60.00   91
 16  ω     66.00 124.00   1.00   12.00    --  111.00  15.00-150.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0457456000
_diffrn_orient_matrix_UB_12      -0.0941223000
_diffrn_orient_matrix_UB_13      -0.1020978000
_diffrn_orient_matrix_UB_21      0.0492379000
_diffrn_orient_matrix_UB_22      -0.1811089000
_diffrn_orient_matrix_UB_23      0.0376932000
_diffrn_orient_matrix_UB_31      -0.1041458000
_diffrn_orient_matrix_UB_32      -0.0443883000
_diffrn_orient_matrix_UB_33      0.0625304000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.829
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                2128
_reflns_number_total             2303
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.093
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details 
;
 Flack x determined using 920 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2303
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.076
_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)+(0.0584P)²+0.0566P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1039
_refine_special_details          ?
_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
2. Others
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.27327(14) 0.11277(15) 0.4627(2) 0.0745(6) Uani 0.878(5) 1 d . . . . .
N1 N 0.35218(15) 0.55352(15) 0.5407(2) 0.0662(4) Uani 1 1 d . . . . .
N2 N 0.43426(13) 0.58916(15) 0.4670(2) 0.0634(4) Uani 1 1 d . . . . .
C1 C 0.33430(15) 0.43999(18) 0.5162(2) 0.0611(5) Uani 1 1 d . . . . .
C2 C 0.24644(17) 0.39652(19) 0.6057(3) 0.0675(5) Uani 1 1 d . . . . .
H2 H 0.2030 0.4420 0.6775 0.081 Uiso 1 1 calc R U . . .
C3 C 0.22191(16) 0.28742(19) 0.5908(3) 0.0684(5) Uani 1 1 d . . . . .
H3 H 0.1615 0.2588 0.6509 0.082 Uiso 1 1 calc R U . . .
C4 C 0.28724(16) 0.21969(18) 0.4861(2) 0.0647(5) Uani 1 1 d . . . . .
C5 C 0.37455(18) 0.2641(2) 0.3949(3) 0.0741(6) Uani 1 1 d . . . . .
H5 H 0.4184 0.2189 0.3233 0.089 Uiso 1 1 calc R U . . .
C6 C 0.39750(17) 0.37199(19) 0.4079(3) 0.0705(5) Uani 1 1 d . . . . .
H6 H 0.4562 0.4011 0.3436 0.085 Uiso 1 1 calc R U . . .
C7 C 0.44948(15) 0.70352(16) 0.4896(2) 0.0603(4) Uani 1 1 d . . . . .
C8 C 0.53956(16) 0.74724(19) 0.4073(3) 0.0705(5) Uani 1 1 d . . . . .
H8 H 0.5869 0.7016 0.3432 0.085 Uiso 1 1 calc R U . . .
C9 C 0.5605(2) 0.8574(2) 0.4188(4) 0.0828(6) Uani 1 1 d . . . . .
H9 H 0.6215 0.8867 0.3615 0.099 Uiso 1 1 calc R U . . .
C10 C 0.4921(2) 0.9245(2) 0.5138(5) 0.0846(7) Uani 1 1 d . . . . .
H10 H 0.5065 0.9995 0.5225 0.102 Uiso 1 1 calc R U . . .
C11 C 0.4025(2) 0.8811(2) 0.5960(4) 0.0832(7) Uani 1 1 d . . . . .
H11 H 0.3558 0.9271 0.6606 0.100 Uiso 1 1 calc R U . . .
C12 C 0.38014(18) 0.7717(2) 0.5855(3) 0.0714(5) Uani 1 1 d . . . . .
H12 H 0.3186 0.7431 0.6424 0.086 Uiso 1 1 calc R U . . .
C13 C 0.1781(2) 0.0651(2) 0.5274(5) 0.0849(10) Uani 0.868(7) 1 d . . P . .
H13A H 0.1167 0.1058 0.4830 0.127 Uiso 0.868(7) 1 calc R U P . .
H13B H 0.1783 0.0661 0.6589 0.127 Uiso 0.868(7) 1 calc R U P . .
H13C H 0.1736 -0.0096 0.4851 0.127 Uiso 0.868(7) 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C4 1.335(3) . ?
O1 C13 1.403(3) . ?
N1 N2 1.236(2) . ?
N1 C1 1.422(3) . ?
N2 C7 1.426(3) . ?
C1 C2 1.383(3) . ?
C1 C6 1.397(3) . ?
C2 H2 0.9400 . ?
C2 C3 1.378(3) . ?
C3 H3 0.9400 . ?
C3 C4 1.395(3) . ?
C4 C5 1.388(3) . ?
C5 H5 0.9400 . ?
C5 C6 1.358(3) . ?
C6 H6 0.9400 . ?
C7 C8 1.382(3) . ?
C7 C12 1.394(3) . ?
C8 H8 0.9400 . ?
C8 C9 1.380(3) . ?
C9 H9 0.9400 . ?
C9 C10 1.375(4) . ?
C10 H10 0.9400 . ?
C10 C11 1.375(4) . ?
C11 H11 0.9400 . ?
C11 C12 1.373(3) . ?
C12 H12 0.9400 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?

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
C4 O1 C13 118.4(2) . . ?
N2 N1 C1 114.83(16) . . ?
N1 N2 C7 113.99(16) . . ?
C2 C1 N1 116.14(18) . . ?
C2 C1 C6 119.1(2) . . ?
C6 C1 N1 124.74(18) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.77(19) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.63(18) . . ?
C4 C3 H3 120.2 . . ?
O1 C4 C3 125.57(19) . . ?
O1 C4 C5 115.17(19) . . ?
C5 C4 C3 119.3(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.90(19) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.30(18) . . ?
C5 C6 H6 119.9 . . ?
C8 C7 N2 116.00(17) . . ?
C8 C7 C12 119.4(2) . . ?
C12 C7 N2 124.62(19) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.4(2) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C7 C12 H12 120.3 . . ?
C11 C12 C7 119.4(2) . . ?
C11 C12 H12 120.3 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O1 C4 C5 C6 -179.9(2) . . . . ?
N1 N2 C7 C8 -179.16(18) . . . . ?
N1 N2 C7 C12 0.2(2) . . . . ?
N1 C1 C2 C3 179.90(18) . . . . ?
N1 C1 C6 C5 179.2(2) . . . . ?
N2 N1 C1 C2 176.41(17) . . . . ?
N2 N1 C1 C6 -4.6(3) . . . . ?
N2 C7 C8 C9 178.9(2) . . . . ?
N2 C7 C12 C11 -179.16(19) . . . . ?
C1 N1 N2 C7 178.66(15) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C1 C6 C5 -1.8(3) . . . . ?
C2 C3 C4 O1 179.0(2) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C7 C8 C9 C10 0.6(4) . . . . ?
C8 C7 C12 C11 0.2(3) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 C7 0.0(4) . . . . ?
C12 C7 C8 C9 -0.5(3) . . . . ?
C13 O1 C4 C3 8.9(3) . . . . ?
C13 O1 C4 C5 -170.5(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Mitegen loop'
_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 1.128
_oxdiff_exptl_absorpt_empirical_full_min 0.850
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jg153_2_140_00
_database_code_depnum_ccdc_archive 'CCDC 2109113'
loop_
_audit_author_name
_audit_author_address
'Nathan Halcovitch'
;Lancaster University
United Kingdom
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 N2 O'
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 N2 O1'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.5682(2)
_cell_length_b                   12.2501(2)
_cell_length_c                   7.27780(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1120.50(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6694
_cell_measurement_temperature    140.01(10)
_cell_measurement_theta_max      75.4930
_cell_measurement_theta_min      5.0280
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.938
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0146
_diffrn_reflns_av_unetI/netI     0.0101
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8600
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.789
_diffrn_reflns_theta_min         5.042
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00    2.00    --  -42.28 125.00  30.00   81
  2  ω   -112.00 -16.00   1.00    2.00    --  -42.28 -57.00 120.00   96
  3  ω    -69.00  28.00   1.00    2.00    --  -42.28  57.00 -90.00   97
  4  ω     61.00 146.00   1.00    8.00    --  111.00 178.00 150.00   85
  5  ω    103.00 178.00   1.00    8.00    --  111.00  77.00  90.00   75
  6  ω     87.00 178.00   1.00    8.00    --  111.00  45.00 -30.00   91
  7  ω     40.00 135.00   1.00    8.00    --  111.00 -45.00  60.00   95
  8  ω    104.00 178.00   1.00    8.00    --  111.00 111.00 120.00   74
  9  ω     61.00 146.00   1.00    8.00    --  111.00 178.00 120.00   85
 10  ω     83.00 178.00   1.00    8.00    --  111.00  61.00-120.00   95
 11  ω     87.00 178.00   1.00    8.00    --  111.00  30.00 -60.00   91
 12  ω    103.00 178.00   1.00    8.00    --  111.00  77.00-180.00   75
 13  ω   -112.00 -16.00   1.00    2.00    --  -42.28 -57.00   0.00   96
 14  ω   -115.00 -20.00   1.00    2.00    --  -42.28 -38.00 150.00   95
 15  ω   -112.00 -16.00   1.00    2.00    --  -42.28 -57.00-120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0411616000
_diffrn_orient_matrix_UB_12      -0.0779031000
_diffrn_orient_matrix_UB_13      -0.1090400000
_diffrn_orient_matrix_UB_21      0.0749264000
_diffrn_orient_matrix_UB_22      0.1662864000
_diffrn_orient_matrix_UB_23      -0.0121998000
_diffrn_orient_matrix_UB_31      0.0877974000
_diffrn_orient_matrix_UB_32      -0.1053929000
_diffrn_orient_matrix_UB_33      0.0614741000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.794
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                2198
_reflns_number_total             2253
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 963 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_coef       0.0048(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2253
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0267
_refine_ls_restrained_S_all      1.058
_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)+(0.0464P)²+0.0725P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0751
_refine_special_details          ?
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.27402(8) 0.89008(8) 0.53907(15) 0.0407(3) Uani 1 1 d . . . . .
N1 N 0.35291(10) 0.44646(10) 0.45636(16) 0.0347(3) Uani 1 1 d . . . . .
N2 N 0.43508(9) 0.41055(9) 0.53290(16) 0.0329(3) Uani 1 1 d . . . . .
C1 C 0.33522(10) 0.55998(12) 0.48257(18) 0.0320(3) Uani 1 1 d . . . . .
C2 C 0.24813(11) 0.60417(13) 0.39100(19) 0.0360(3) Uani 1 1 d . . . . .
H2 H 0.2047 0.5584 0.3168 0.043 Uiso 1 1 calc R U . . .
C3 C 0.22391(10) 0.71442(12) 0.40682(19) 0.0356(3) Uani 1 1 d . . . . .
H3 H 0.1640 0.7440 0.3448 0.043 Uiso 1 1 calc R U . . .
C4 C 0.28831(10) 0.78102(12) 0.51428(17) 0.0325(3) Uani 1 1 d . . . . .
C5 C 0.37540(10) 0.73670(12) 0.60825(19) 0.0356(3) Uani 1 1 d . . . . .
H5 H 0.4189 0.7824 0.6822 0.043 Uiso 1 1 calc R U . . .
C6 C 0.39822(10) 0.62735(12) 0.59395(19) 0.0344(3) Uani 1 1 d . . . . .
H6 H 0.4567 0.5974 0.6595 0.041 Uiso 1 1 calc R U . . .
C7 C 0.45039(10) 0.29586(11) 0.50988(18) 0.0320(3) Uani 1 1 d . . . . .
C8 C 0.53921(11) 0.25257(12) 0.5962(2) 0.0372(3) Uani 1 1 d . . . . .
H8 H 0.5855 0.2988 0.6640 0.045 Uiso 1 1 calc R U . . .
C9 C 0.56064(13) 0.14132(13) 0.5833(2) 0.0452(4) Uani 1 1 d . . . . .
H9 H 0.6215 0.1116 0.6425 0.054 Uiso 1 1 calc R U . . .
C10 C 0.49314(14) 0.07383(13) 0.4842(3) 0.0466(4) Uani 1 1 d . . . . .
H10 H 0.5074 -0.0022 0.4759 0.056 Uiso 1 1 calc R U . . .
C11 C 0.40469(13) 0.11782(13) 0.3972(2) 0.0452(4) Uani 1 1 d . . . . .
H11 H 0.3590 0.0716 0.3282 0.054 Uiso 1 1 calc R U . . .
C12 C 0.38211(12) 0.22809(13) 0.4097(2) 0.0381(3) Uani 1 1 d . . . . .
H12 H 0.3210 0.2574 0.3509 0.046 Uiso 1 1 calc R U . . .
C13 C 0.17931(13) 0.93766(14) 0.4703(3) 0.0489(4) Uani 1 1 d . . . . .
H13A H 0.1800 0.9352 0.3357 0.073 Uiso 1 1 calc R U . . .
H13B H 0.1747 1.0137 0.5112 0.073 Uiso 1 1 calc R U . . .
H13C H 0.1177 0.8969 0.5163 0.073 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C4 1.3600(17) . ?
O1 C13 1.4168(18) . ?
N1 N2 1.2531(16) . ?
N1 C1 1.4212(17) . ?
N2 C7 1.4279(16) . ?
C1 C2 1.3911(19) . ?
C1 C6 1.4017(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
C4 C5 1.4002(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.374(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.3863(19) . ?
C7 C12 1.3991(19) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.383(2) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C4 O1 C13 117.92(12) . . ?
N2 N1 C1 114.38(11) . . ?
N1 N2 C7 113.85(11) . . ?
C2 C1 N1 116.07(12) . . ?
C2 C1 C6 119.50(13) . . ?
C6 C1 N1 124.42(12) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.73(13) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.31(12) . . ?
C4 C3 H3 120.3 . . ?
O1 C4 C3 125.05(12) . . ?
O1 C4 C5 114.79(12) . . ?
C3 C4 C5 120.16(13) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.28(12) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 119.99(12) . . ?
C5 C6 H6 120.0 . . ?
C8 C7 N2 115.58(12) . . ?
C8 C7 C12 120.20(13) . . ?
C12 C7 N2 124.22(12) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 119.99(13) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.00(15) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.71(15) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 120.90(15) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 H12 120.4 . . ?
C11 C12 C7 119.19(14) . . ?
C11 C12 H12 120.4 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O1 C4 C5 C6 -179.91(12) . . . . ?
N1 N2 C7 C8 -178.59(12) . . . . ?
N1 N2 C7 C12 0.88(17) . . . . ?
N1 C1 C2 C3 -179.81(12) . . . . ?
N1 C1 C6 C5 179.07(13) . . . . ?
N2 N1 C1 C2 176.44(12) . . . . ?
N2 N1 C1 C6 -4.29(18) . . . . ?
N2 C7 C8 C9 179.44(13) . . . . ?
N2 C7 C12 C11 -179.75(14) . . . . ?
C1 N1 N2 C7 178.34(10) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C2 C1 C6 C5 -1.7(2) . . . . ?
C2 C3 C4 O1 179.15(13) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C6 C1 C2 C3 0.9(2) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C8 C7 C12 C11 -0.3(2) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C10 C11 C12 C7 0.7(2) . . . . ?
C12 C7 C8 C9 -0.1(2) . . . . ?
C13 O1 C4 C3 8.5(2) . . . . ?
C13 O1 C4 C5 -171.12(13) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Mitegen loop'
_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 1.333
_oxdiff_exptl_absorpt_empirical_full_min 0.696
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jg153_5_260_00
_database_code_depnum_ccdc_archive 'CCDC 2109116'
loop_
_audit_author_name
_audit_author_address
'Nathan Halcovitch'
;Lancaster University
United Kingdom
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 N2 O'
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 N2 O1'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.6100(2)
_cell_length_b                   12.3302(3)
_cell_length_c                   7.39190(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1149.32(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5808
_cell_measurement_temperature    260.00(10)
_cell_measurement_theta_max      75.9580
_cell_measurement_theta_min      5.0020
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8868
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.177
_diffrn_reflns_theta_min         5.017
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      260.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00    4.00    --  -42.28 125.00  30.00   81
  2  ω   -112.00 -16.00   1.00    4.00    --  -42.28 -57.00 120.00   96
  3  ω    -69.00  28.00   1.00    4.00    --  -42.28  57.00 -90.00   97
  4  ω     61.00 146.00   1.00   16.00    --  111.00 178.00 150.00   85
  5  ω    103.00 178.00   1.00   16.00    --  111.00  77.00  90.00   75
  6  ω     87.00 178.00   1.00   16.00    --  111.00  45.00 -30.00   91
  7  ω     40.00 135.00   1.00   16.00    --  111.00 -45.00  60.00   95
  8  ω    104.00 178.00   1.00   16.00    --  111.00 111.00 120.00   74
  9  ω     61.00 146.00   1.00   16.00    --  111.00 178.00 120.00   85
 10  ω     83.00 178.00   1.00   16.00    --  111.00  61.00-120.00   95
 11  ω     87.00 178.00   1.00   16.00    --  111.00  30.00 -60.00   91
 12  ω    103.00 178.00   1.00   16.00    --  111.00  77.00-180.00   75
 13  ω   -112.00 -16.00   1.00    4.00    --  -42.28 -57.00   0.00   96
 14  ω   -115.00 -20.00   1.00    4.00    --  -42.28 -38.00 150.00   95
 15  ω   -112.00 -16.00   1.00    4.00    --  -42.28 -57.00-120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0413156000
_diffrn_orient_matrix_UB_12      0.0776041000
_diffrn_orient_matrix_UB_13      -0.1080130000
_diffrn_orient_matrix_UB_21      -0.0746280000
_diffrn_orient_matrix_UB_22      -0.1636800000
_diffrn_orient_matrix_UB_23      -0.0124530000
_diffrn_orient_matrix_UB_31      -0.0874253000
_diffrn_orient_matrix_UB_32      0.1030490000
_diffrn_orient_matrix_UB_33      0.0616133000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.796
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                2190
_reflns_number_total             2319
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.101
_refine_diff_density_min         -0.098
_refine_diff_density_rms         0.020
_refine_ls_abs_structure_details 
;
 Flack x determined using 945 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(8)
_refine_ls_extinction_coef       0.0071(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2319
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.070
_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)+(0.0567P)²+0.0406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0944
_refine_special_details          ?
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.27164(11) 0.88571(11) 0.46287(19) 0.0769(4) Uani 1 1 d . . . . .
N1 N 0.35340(12) 0.44580(13) 0.5412(2) 0.0646(4) Uani 1 1 d . . . . .
N2 N 0.43444(11) 0.41055(12) 0.46682(17) 0.0612(4) Uani 1 1 d . . . . .
C1 C 0.33529(12) 0.55851(14) 0.5165(2) 0.0578(4) Uani 1 1 d . . . . .
C2 C 0.24889(14) 0.60141(17) 0.6073(2) 0.0675(5) Uani 1 1 d . . . . .
H2 H 0.2071 0.5566 0.6790 0.081 Uiso 1 1 calc R U . . .
C3 C 0.22422(13) 0.71053(17) 0.5924(2) 0.0667(5) Uani 1 1 d . . . . .
H3 H 0.1658 0.7387 0.6533 0.080 Uiso 1 1 calc R U . . .
C4 C 0.28694(13) 0.77740(15) 0.4865(2) 0.0608(4) Uani 1 1 d . . . . .
C5 C 0.37320(13) 0.73389(16) 0.3935(2) 0.0669(4) Uani 1 1 d . . . . .
H5 H 0.4150 0.7786 0.3214 0.080 Uiso 1 1 calc R U . . .
C6 C 0.39676(13) 0.62631(15) 0.4073(2) 0.0639(4) Uani 1 1 d . . . . .
H6 H 0.4540 0.5979 0.3438 0.077 Uiso 1 1 calc R U . . .
C7 C 0.45013(13) 0.29664(14) 0.4893(2) 0.0588(4) Uani 1 1 d . . . . .
C8 C 0.53807(14) 0.25388(16) 0.4053(3) 0.0703(5) Uani 1 1 d . . . . .
H8 H 0.5833 0.2990 0.3405 0.084 Uiso 1 1 calc R U . . .
C9 C 0.5595(2) 0.14420(18) 0.4169(4) 0.0868(6) Uani 1 1 d . . . . .
H9 H 0.6187 0.1156 0.3591 0.104 Uiso 1 1 calc R U . . .
C10 C 0.4932(2) 0.07722(18) 0.5140(4) 0.0883(6) Uani 1 1 d . . . . .
H10 H 0.5077 0.0034 0.5224 0.106 Uiso 1 1 calc R U . . .
C11 C 0.40546(19) 0.11993(19) 0.5985(3) 0.0856(6) Uani 1 1 d . . . . .
H11 H 0.3609 0.0746 0.6643 0.103 Uiso 1 1 calc R U . . .
C12 C 0.38299(16) 0.22865(17) 0.5868(2) 0.0713(5) Uani 1 1 d . . . . .
H12 H 0.3232 0.2567 0.6436 0.086 Uiso 1 1 calc R U . . .
C13 C 0.1785(2) 0.9329(2) 0.5306(4) 0.0917(7) Uani 1 1 d . . . . .
H13A H 0.1181 0.8938 0.4858 0.137 Uiso 1 1 calc R U . . .
H13B H 0.1744 1.0071 0.4919 0.137 Uiso 1 1 calc R U . . .
H13C H 0.1792 0.9300 0.6603 0.137 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C4 1.361(2) . ?
O1 C13 1.403(3) . ?
N1 N2 1.2390(19) . ?
N1 C1 1.420(2) . ?
N2 C7 1.428(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.397(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.385(2) . ?
C4 C5 1.394(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.363(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(2) . ?
C7 C12 1.392(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.373(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C4 O1 C13 118.66(17) . . ?
N2 N1 C1 114.76(13) . . ?
N1 N2 C7 114.06(14) . . ?
C2 C1 N1 115.97(15) . . ?
C2 C1 C6 119.22(17) . . ?
C6 C1 N1 124.81(14) . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.61(16) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.65(15) . . ?
C4 C3 H3 120.2 . . ?
O1 C4 C3 125.16(15) . . ?
O1 C4 C5 115.14(15) . . ?
C3 C4 C5 119.69(16) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.48(16) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.33(15) . . ?
C5 C6 H6 119.8 . . ?
C8 C7 N2 115.84(15) . . ?
C8 C7 C12 119.52(17) . . ?
C12 C7 N2 124.63(16) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.29(18) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.7(2) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 120.2 . . ?
C11 C12 C7 119.68(19) . . ?
C11 C12 H12 120.2 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O1 C4 C5 C6 179.69(16) . . . . ?
N1 N2 C7 C8 178.61(16) . . . . ?
N1 N2 C7 C12 -0.7(2) . . . . ?
N1 C1 C2 C3 179.98(16) . . . . ?
N1 C1 C6 C5 -179.56(16) . . . . ?
N2 N1 C1 C2 -176.15(15) . . . . ?
N2 N1 C1 C6 4.7(2) . . . . ?
N2 C7 C8 C9 -179.13(19) . . . . ?
N2 C7 C12 C11 179.55(17) . . . . ?
C1 N1 N2 C7 -178.57(13) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C2 C1 C6 C5 1.3(3) . . . . ?
C2 C3 C4 O1 -179.23(17) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 -0.6(3) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C6 C1 C2 C3 -0.8(3) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C8 C7 C12 C11 0.2(3) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 C7 -0.5(3) . . . . ?
C12 C7 C8 C9 0.2(3) . . . . ?
C13 O1 C4 C3 -8.6(3) . . . . ?
C13 O1 C4 C5 171.11(19) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Mitegen loop'
_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.692
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jg154_3_180_00
_database_code_depnum_ccdc_archive 'CCDC 2109120'
loop_
_audit_author_name
_audit_author_address
'Nathan Halcovitch'
;Lancaster University
United Kingdom
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12.855 H11.565 N2 O0.873'
_chemical_formula_sum            'C12.86 H11.57 N2 O0.87'
_chemical_formula_weight         208.03
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 N2 O1'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.4062(3)
_cell_length_b                   12.2515(3)
_cell_length_c                   7.33650(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1115.11(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4913
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      75.6890
_cell_measurement_theta_min      5.0760
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.637
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             439
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_unetI/netI     0.0102
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8613
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.108
_diffrn_reflns_theta_min         5.074
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  28.00   1.00    2.00    --  -42.28  57.00  30.00   97
  2  ω   -112.00 -16.00   1.00    2.00    --  -42.28 -57.00-120.00   96
  3  ω    -87.00  -6.00   1.00    2.00    --  -42.28 125.00  60.00   81
  4  ω     36.00 109.00   1.00    8.00    --  111.00-111.00 -30.00   73
  5  ω    103.00 178.00   1.00    8.00    --  111.00  77.00 -60.00   75
  6  ω     41.00 139.00   1.00    8.00    --  111.00 -61.00 -60.00   98
  7  ω    103.00 178.00   1.00    8.00    --  111.00  77.00-150.00   75
  8  ω    103.00 178.00   1.00    8.00    --  111.00  77.00 -30.00   75
  9  ω    103.00 178.00   1.00    8.00    --  111.00  77.00-120.00   75
 10  ω    103.00 178.00   1.00    8.00    --  111.00  77.00  90.00   75
 11  ω     30.00 107.00   1.00    8.00    --  111.00 -94.00 150.00   77
 12  ω    103.00 178.00   1.00    8.00    --  111.00  77.00 150.00   75
 13  ω   -112.00 -16.00   1.00    2.00    --  -42.28 -57.00  60.00   96
 14  ω   -112.00 -16.00   1.00    2.00    --  -42.28 -57.00 -30.00   96
 15  ω     87.00 178.00   1.00    8.00    --  111.00  30.00  60.00   91
 16  ω     66.00 124.00   1.00    8.00    --  111.00  15.00-150.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0473585000
_diffrn_orient_matrix_UB_12      0.0952276000
_diffrn_orient_matrix_UB_13      -0.1013564000
_diffrn_orient_matrix_UB_21      -0.0490894000
_diffrn_orient_matrix_UB_22      0.1822582000
_diffrn_orient_matrix_UB_23      0.0378579000
_diffrn_orient_matrix_UB_31      0.1037342000
_diffrn_orient_matrix_UB_32      0.0427437000
_diffrn_orient_matrix_UB_33      0.0640715000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                2144
_reflns_number_total             2284
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.104
_refine_diff_density_min         -0.104
_refine_diff_density_rms         0.022
_refine_ls_abs_structure_details 
;
 Flack x determined using 937 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2284
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.041
_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)+(0.0515P)²+0.0840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0946
_refine_special_details          ?
_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
2. Others
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C6(H6), C2(H2), C8(H8), C12(H12), C9(H9), C11(H11), C10(H10)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72587(13) 0.88849(14) 0.5377(2) 0.0636(6) Uani 0.873(5) 1 d . . . . .
N2 N 0.56550(12) 0.41078(14) 0.53265(19) 0.0551(4) Uani 1 1 d . . . . .
N1 N 0.64818(14) 0.44679(14) 0.4583(2) 0.0575(4) Uani 1 1 d . . . . .
C1 C 0.66595(15) 0.56037(17) 0.4831(2) 0.0538(4) Uani 1 1 d . . . . .
C7 C 0.55039(15) 0.29623(16) 0.5100(2) 0.0523(4) Uani 1 1 d . . . . .
C4 C 0.71245(16) 0.78143(17) 0.5137(2) 0.0562(5) Uani 1 1 d . . . . .
C5 C 0.62485(17) 0.73667(19) 0.6052(3) 0.0650(5) Uani 1 1 d . . . . .
H5 H 0.5803 0.7823 0.6779 0.078 Uiso 1 1 calc R U . . .
C3 C 0.77831(15) 0.71397(18) 0.4088(2) 0.0590(5) Uani 1 1 d . . . . .
H3 H 0.8395 0.7432 0.3481 0.071 Uiso 1 1 calc R U . . .
C6 C 0.60203(16) 0.62830(18) 0.5921(3) 0.0619(5) Uani 1 1 d . . . . .
H6 H 0.5426 0.5987 0.6570 0.074 Uiso 1 1 calc R U . . .
C2 C 0.75398(16) 0.60431(18) 0.3937(3) 0.0577(5) Uani 1 1 d . . . . .
H2 H 0.7983 0.5585 0.3209 0.069 Uiso 1 1 calc R U . . .
C8 C 0.45992(15) 0.25233(18) 0.5928(3) 0.0609(5) Uani 1 1 d . . . . .
H8 H 0.4120 0.2985 0.6580 0.073 Uiso 1 1 calc R U . . .
C12 C 0.62010(17) 0.22821(19) 0.4133(3) 0.0618(5) Uani 1 1 d . . . . .
H12 H 0.6824 0.2574 0.3559 0.074 Uiso 1 1 calc R U . . .
C9 C 0.43901(19) 0.14156(19) 0.5808(3) 0.0701(6) Uani 1 1 d . . . . .
H9 H 0.3771 0.1118 0.6385 0.084 Uiso 1 1 calc R U . . .
C11 C 0.5978(2) 0.1183(2) 0.4019(3) 0.0711(6) Uani 1 1 d . . . . .
H11 H 0.6450 0.0720 0.3355 0.085 Uiso 1 1 calc R U . . .
C10 C 0.5082(2) 0.07436(19) 0.4852(4) 0.0722(6) Uani 1 1 d . . . . .
H10 H 0.4941 -0.0017 0.4768 0.087 Uiso 1 1 calc R U . . .
C13 C 0.8216(2) 0.9364(2) 0.4729(4) 0.0714(9) Uani 0.855(7) 1 d . . P . .
H13A H 0.8219 0.9349 0.3393 0.107 Uiso 0.855(7) 1 calc R U P . .
H13B H 0.8837 0.8954 0.5191 0.107 Uiso 0.855(7) 1 calc R U P . .
H13C H 0.8258 1.0122 0.5151 0.107 Uiso 0.855(7) 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C4 1.334(3) . ?
O1 C13 1.408(3) . ?
N2 N1 1.243(2) . ?
N2 C7 1.426(2) . ?
N1 C1 1.421(2) . ?
C1 C6 1.400(3) . ?
C1 C2 1.383(3) . ?
C7 C8 1.385(3) . ?
C7 C12 1.395(3) . ?
C4 C5 1.390(3) . ?
C4 C3 1.394(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.361(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.381(3) . ?
C6 H6 0.9500 . ?
C2 H2 0.9500 . ?
C8 H8 0.9500 . ?
C8 C9 1.384(3) . ?
C12 H12 0.9500 . ?
C12 C11 1.377(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(3) . ?
C11 H11 0.9500 . ?
C11 C10 1.378(4) . ?
C10 H10 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C4 O1 C13 118.1(2) . . ?
N1 N2 C7 114.01(16) . . ?
N2 N1 C1 114.80(16) . . ?
C6 C1 N1 124.58(17) . . ?
C2 C1 N1 116.28(17) . . ?
C2 C1 C6 119.13(19) . . ?
C8 C7 N2 115.96(17) . . ?
C8 C7 C12 119.57(19) . . ?
C12 C7 N2 124.46(18) . . ?
O1 C4 C5 114.94(18) . . ?
O1 C4 C3 125.64(18) . . ?
C5 C4 C3 119.41(19) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.89(18) . . ?
C6 C5 H5 119.6 . . ?
C4 C3 H3 120.2 . . ?
C2 C3 C4 119.52(18) . . ?
C2 C3 H3 120.2 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.15(18) . . ?
C5 C6 H6 119.9 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.86(19) . . ?
C3 C2 H2 119.6 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.32(19) . . ?
C9 C8 H8 119.8 . . ?
C7 C12 H12 120.3 . . ?
C11 C12 C7 119.4(2) . . ?
C11 C12 H12 120.3 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C12 C11 H11 119.4 . . ?
C12 C11 C10 121.1(2) . . ?
C10 C11 H11 119.4 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O1 C4 C5 C6 179.93(19) . . . . ?
O1 C4 C3 C2 -179.08(19) . . . . ?
N2 N1 C1 C6 4.4(3) . . . . ?
N2 N1 C1 C2 -176.49(16) . . . . ?
N2 C7 C8 C9 -179.07(18) . . . . ?
N2 C7 C12 C11 179.39(19) . . . . ?
N1 N2 C7 C8 179.18(17) . . . . ?
N1 N2 C7 C12 -0.3(2) . . . . ?
N1 C1 C6 C5 -179.10(19) . . . . ?
N1 C1 C2 C3 179.96(17) . . . . ?
C7 N2 N1 C1 -178.55(14) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C7 C12 C11 C10 -0.4(3) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C3 C2 C1 -0.8(3) . . . . ?
C5 C4 C3 C2 1.6(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C6 C1 C2 C3 -0.9(3) . . . . ?
C2 C1 C6 C5 1.8(3) . . . . ?
C8 C7 C12 C11 -0.1(3) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C12 C7 C8 C9 0.4(3) . . . . ?
C12 C11 C10 C9 0.4(4) . . . . ?
C13 O1 C4 C5 170.4(2) . . . . ?
C13 O1 C4 C3 -8.9(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Mitegen loop'
_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 1.141
_oxdiff_exptl_absorpt_empirical_full_min 0.856
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jg154_6_290_00
_database_code_depnum_ccdc_archive 'CCDC 2109123'
loop_
_audit_author_name
_audit_author_address
'Nathan Halcovitch'
;Lancaster University
United Kingdom
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12.902 H11.705 N2 O0.885'
_chemical_formula_sum            'C12.90 H11.70 N2 O0.88'
_chemical_formula_weight         208.94
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 N2 O1'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.4634(5)
_cell_length_b                   12.3362(5)
_cell_length_c                   7.4618(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1147.26(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3852
_cell_measurement_temperature    290.00(10)
_cell_measurement_theta_max      74.4490
_cell_measurement_theta_min      5.0370
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             441
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0133
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8831
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.265
_diffrn_reflns_theta_min         5.044
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  28.00   1.00    4.00    --  -42.28  57.00  30.00   97
  2  ω   -112.00 -16.00   1.00    4.00    --  -42.28 -57.00-120.00   96
  3  ω    -87.00  -6.00   1.00    4.00    --  -42.28 125.00  60.00   81
  4  ω     36.00 109.00   1.00   16.00    --  111.00-111.00 -30.00   73
  5  ω    103.00 178.00   1.00   16.00    --  111.00  77.00 -60.00   75
  6  ω     41.00 139.00   1.00   16.00    --  111.00 -61.00 -60.00   98
  7  ω    103.00 178.00   1.00   16.00    --  111.00  77.00-150.00   75
  8  ω    103.00 178.00   1.00   16.00    --  111.00  77.00 -30.00   75
  9  ω    103.00 178.00   1.00   16.00    --  111.00  77.00-120.00   75
 10  ω    103.00 178.00   1.00   16.00    --  111.00  77.00  90.00   75
 11  ω     30.00 107.00   1.00   16.00    --  111.00 -94.00 150.00   77
 12  ω    103.00 178.00   1.00   16.00    --  111.00  77.00 150.00   75
 13  ω   -112.00 -16.00   1.00    4.00    --  -42.28 -57.00  60.00   96
 14  ω   -112.00 -16.00   1.00    4.00    --  -42.28 -57.00 -30.00   96
 15  ω     87.00 178.00   1.00   16.00    --  111.00  30.00  60.00   91
 16  ω     66.00 124.00   1.00   16.00    --  111.00  15.00-150.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0325973000
_diffrn_orient_matrix_UB_12      0.0929226000
_diffrn_orient_matrix_UB_13      -0.1065851000
_diffrn_orient_matrix_UB_21      -0.0526333000
_diffrn_orient_matrix_UB_22      0.1750374000
_diffrn_orient_matrix_UB_23      0.0394200000
_diffrn_orient_matrix_UB_31      0.1069302000
_diffrn_orient_matrix_UB_32      0.0578729000
_diffrn_orient_matrix_UB_33      0.0519077000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                1966
_reflns_number_total             2344
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.082
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 
;
 Flack x determined using 808 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.25(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0417
_refine_ls_restrained_S_all      1.037
_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)+(0.0805P)²+0.0528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1401
_refine_special_details          ?
_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
2. Others
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72825(19) 0.8846(2) 0.5366(3) 0.1008(10) Uani 0.885(7) 1 d . . . . .
N1 N 0.6471(2) 0.4458(2) 0.4609(3) 0.0892(7) Uani 1 1 d . . . . .
N2 N 0.56659(18) 0.4115(2) 0.5333(3) 0.0857(6) Uani 1 1 d . . . . .
C1 C 0.6652(2) 0.5592(2) 0.4847(3) 0.0793(6) Uani 1 1 d . . . . .
C2 C 0.7525(2) 0.6019(3) 0.3955(4) 0.0909(8) Uani 1 1 d . . . . .
H2 H 0.7951 0.5570 0.3252 0.109 Uiso 1 1 calc R U . . .
C3 C 0.7772(2) 0.7105(3) 0.4096(4) 0.0919(8) Uani 1 1 d . . . . .
H3 H 0.8364 0.7386 0.3498 0.110 Uiso 1 1 calc R U . . .
C4 C 0.7130(2) 0.7776(2) 0.5139(3) 0.0860(7) Uani 1 1 d . . . . .
C5 C 0.6265(2) 0.7343(3) 0.6041(4) 0.0957(8) Uani 1 1 d . . . . .
H5 H 0.5838 0.7791 0.6746 0.115 Uiso 1 1 calc R U . . .
C6 C 0.6030(2) 0.6278(3) 0.5917(4) 0.0929(8) Uani 1 1 d . . . . .
H6 H 0.5449 0.5998 0.6548 0.111 Uiso 1 1 calc R U . . .
C7 C 0.5510(2) 0.2968(2) 0.5107(3) 0.0807(6) Uani 1 1 d . . . . .
C8 C 0.4614(2) 0.2538(3) 0.5916(4) 0.0943(8) Uani 1 1 d . . . . .
H8 H 0.4148 0.2989 0.6542 0.113 Uiso 1 1 calc R U . . .
C9 C 0.4403(3) 0.1451(3) 0.5808(6) 0.1116(10) Uani 1 1 d . . . . .
H9 H 0.3798 0.1168 0.6369 0.134 Uiso 1 1 calc R U . . .
C10 C 0.5075(3) 0.0781(3) 0.4880(7) 0.1129(11) Uani 1 1 d . . . . .
H10 H 0.4928 0.0043 0.4805 0.135 Uiso 1 1 calc R U . . .
C11 C 0.5966(3) 0.1201(3) 0.4061(5) 0.1125(11) Uani 1 1 d . . . . .
H11 H 0.6424 0.0744 0.3431 0.135 Uiso 1 1 calc R U . . .
C12 C 0.6192(3) 0.2287(3) 0.4159(4) 0.0956(8) Uani 1 1 d . . . . .
H12 H 0.6798 0.2566 0.3594 0.115 Uiso 1 1 calc R U . . .
C13 C 0.8225(3) 0.9313(4) 0.4723(7) 0.1193(17) Uani 0.902(10) 1 d . . P . .
H13A H 0.8236 0.9272 0.3438 0.179 Uiso 0.902(10) 1 calc R U P . .
H13B H 0.8832 0.8930 0.5200 0.179 Uiso 0.902(10) 1 calc R U P . .
H13C H 0.8257 1.0058 0.5088 0.179 Uiso 0.902(10) 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C4 1.344(4) . ?
O1 C13 1.394(4) . ?
N1 N2 1.216(3) . ?
N1 C1 1.428(3) . ?
N2 C7 1.438(3) . ?
C1 C2 1.380(4) . ?
C1 C6 1.398(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(4) . ?
C4 C5 1.378(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.349(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(4) . ?
C7 C12 1.389(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.368(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.366(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.370(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.371(5) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C4 O1 C13 118.8(3) . . ?
N2 N1 C1 114.6(2) . . ?
N1 N2 C7 113.7(2) . . ?
C2 C1 N1 116.0(2) . . ?
C2 C1 C6 118.8(3) . . ?
C6 C1 N1 125.2(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
O1 C4 C3 125.0(3) . . ?
O1 C4 C5 115.5(3) . . ?
C5 C4 C3 119.5(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.7 . . ?
C8 C7 N2 115.9(2) . . ?
C8 C7 C12 119.2(3) . . ?
C12 C7 N2 124.9(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.9(3) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 120.3 . . ?
C11 C12 C7 119.5(3) . . ?
C11 C12 H12 120.3 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O1 C4 C5 C6 179.9(3) . . . . ?
N1 N2 C7 C8 179.4(2) . . . . ?
N1 N2 C7 C12 -0.2(3) . . . . ?
N1 C1 C2 C3 -179.9(3) . . . . ?
N1 C1 C6 C5 -179.5(3) . . . . ?
N2 N1 C1 C2 -176.4(2) . . . . ?
N2 N1 C1 C6 4.7(4) . . . . ?
N2 C7 C8 C9 -178.9(3) . . . . ?
N2 C7 C12 C11 179.0(3) . . . . ?
C1 N1 N2 C7 -178.8(2) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C1 C6 C5 1.5(4) . . . . ?
C2 C3 C4 O1 -179.3(3) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C1 -0.9(5) . . . . ?
C6 C1 C2 C3 -0.9(4) . . . . ?
C7 C8 C9 C10 -0.6(6) . . . . ?
C8 C7 C12 C11 -0.6(4) . . . . ?
C8 C9 C10 C11 0.2(7) . . . . ?
C9 C10 C11 C12 -0.1(7) . . . . ?
C10 C11 C12 C7 0.3(5) . . . . ?
C12 C7 C8 C9 0.8(5) . . . . ?
C13 O1 C4 C3 -9.2(5) . . . . ?
C13 O1 C4 C5 170.5(3) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Mitegen loop'
_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 1.167
_oxdiff_exptl_absorpt_empirical_full_min 0.855
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jg153_6_290_00
_database_code_depnum_ccdc_archive 'CCDC 2109117'
loop_
_audit_author_name
_audit_author_address
'Nathan Halcovitch'
;Lancaster University
United Kingdom
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 N2 O'
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 N2 O1'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.6139(3)
_cell_length_b                   12.3565(4)
_cell_length_c                   7.4286(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1157.85(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5186
_cell_measurement_temperature    290.00(10)
_cell_measurement_theta_max      75.5440
_cell_measurement_theta_min      4.9960
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8938
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.079
_diffrn_reflns_theta_min         5.010
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00    4.00    --  -42.28 125.00  30.00   81
  2  ω   -112.00 -16.00   1.00    4.00    --  -42.28 -57.00 120.00   96
  3  ω    -69.00  28.00   1.00    4.00    --  -42.28  57.00 -90.00   97
  4  ω     61.00 146.00   1.00   16.00    --  111.00 178.00 150.00   85
  5  ω    103.00 178.00   1.00   16.00    --  111.00  77.00  90.00   75
  6  ω     87.00 178.00   1.00   16.00    --  111.00  45.00 -30.00   91
  7  ω     40.00 135.00   1.00   16.00    --  111.00 -45.00  60.00   95
  8  ω    104.00 178.00   1.00   16.00    --  111.00 111.00 120.00   74
  9  ω     61.00 146.00   1.00   16.00    --  111.00 178.00 120.00   85
 10  ω     83.00 178.00   1.00   16.00    --  111.00  61.00-120.00   95
 11  ω     87.00 178.00   1.00   16.00    --  111.00  30.00 -60.00   91
 12  ω    103.00 178.00   1.00   16.00    --  111.00  77.00-180.00   75
 13  ω   -112.00 -16.00   1.00    4.00    --  -42.28 -57.00   0.00   96
 14  ω   -115.00 -20.00   1.00    4.00    --  -42.28 -38.00 150.00   95
 15  ω   -112.00 -16.00   1.00    4.00    --  -42.28 -57.00-120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0422608000
_diffrn_orient_matrix_UB_12      -0.0772611000
_diffrn_orient_matrix_UB_13      0.1073151000
_diffrn_orient_matrix_UB_21      -0.0750105000
_diffrn_orient_matrix_UB_22      0.1623944000
_diffrn_orient_matrix_UB_23      0.0113935000
_diffrn_orient_matrix_UB_31      -0.0864934000
_diffrn_orient_matrix_UB_32      -0.1032900000
_diffrn_orient_matrix_UB_33      -0.0626162000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.800
_reflns_Friedel_fraction_full    0.959
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                2153
_reflns_number_total             2351
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.098
_refine_diff_density_min         -0.082
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details 
;
 Flack x determined using 922 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(10)
_refine_ls_extinction_coef       0.0040(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2351
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0333
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0562P)²+0.0503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1033
_refine_special_details          ?
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.27113(13) 0.88444(14) 0.5366(2) 0.0898(5) Uani 1 1 d . . . . .
N1 N 0.35365(14) 0.44559(15) 0.4597(2) 0.0749(5) Uani 1 1 d . . . . .
N2 N 0.43403(12) 0.41089(14) 0.5334(2) 0.0712(4) Uani 1 1 d . . . . .
C1 C 0.33538(14) 0.55824(17) 0.4841(3) 0.0665(5) Uani 1 1 d . . . . .
C2 C 0.24931(17) 0.6007(2) 0.3933(3) 0.0786(6) Uani 1 1 d . . . . .
H2 H 0.2077 0.5558 0.3217 0.094 Uiso 1 1 calc R U . . .
C3 C 0.22441(15) 0.7095(2) 0.4081(3) 0.0773(6) Uani 1 1 d . . . . .
H3 H 0.1660 0.7376 0.3475 0.093 Uiso 1 1 calc R U . . .
C4 C 0.28680(15) 0.77618(17) 0.5134(2) 0.0702(5) Uani 1 1 d . . . . .
C5 C 0.37265(16) 0.73329(19) 0.6060(3) 0.0773(5) Uani 1 1 d . . . . .
H5 H 0.4142 0.7780 0.6779 0.093 Uiso 1 1 calc R U . . .
C6 C 0.39648(15) 0.62607(18) 0.5923(3) 0.0737(5) Uani 1 1 d . . . . .
H6 H 0.4538 0.5980 0.6556 0.088 Uiso 1 1 calc R U . . .
C7 C 0.44984(15) 0.29688(16) 0.5107(2) 0.0679(5) Uani 1 1 d . . . . .
C8 C 0.53764(17) 0.25441(19) 0.5944(3) 0.0811(6) Uani 1 1 d . . . . .
H8 H 0.5827 0.2995 0.6591 0.097 Uiso 1 1 calc R U . . .
C9 C 0.5593(2) 0.1452(2) 0.5829(4) 0.0995(8) Uani 1 1 d . . . . .
H9 H 0.6187 0.1169 0.6402 0.119 Uiso 1 1 calc R U . . .
C10 C 0.4935(3) 0.0783(2) 0.4872(5) 0.1019(8) Uani 1 1 d . . . . .
H10 H 0.5082 0.0047 0.4790 0.122 Uiso 1 1 calc R U . . .
C11 C 0.4055(2) 0.1206(2) 0.4032(4) 0.0993(8) Uani 1 1 d . . . . .
H11 H 0.3607 0.0752 0.3384 0.119 Uiso 1 1 calc R U . . .
C12 C 0.38317(18) 0.2290(2) 0.4143(3) 0.0825(6) Uani 1 1 d . . . . .
H12 H 0.3235 0.2570 0.3572 0.099 Uiso 1 1 calc R U . . .
C13 C 0.1783(2) 0.9314(2) 0.4694(5) 0.1063(9) Uani 1 1 d . . . . .
H13A H 0.1777 0.9258 0.3405 0.159 Uiso 1 1 calc R U . . .
H13B H 0.1758 1.0063 0.5036 0.159 Uiso 1 1 calc R U . . .
H13C H 0.1179 0.8944 0.5179 0.159 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C4 1.363(2) . ?
O1 C13 1.398(3) . ?
N1 N2 1.230(2) . ?
N1 C1 1.422(2) . ?
N2 C7 1.433(2) . ?
C1 C2 1.381(3) . ?
C1 C6 1.394(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(3) . ?
C4 C5 1.388(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.362(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(3) . ?
C7 C12 1.387(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.370(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.372(4) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C4 O1 C13 118.9(2) . . ?
N2 N1 C1 114.71(16) . . ?
N1 N2 C7 113.90(16) . . ?
C2 C1 N1 115.90(18) . . ?
C2 C1 C6 119.2(2) . . ?
C6 C1 N1 124.91(17) . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.54(19) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.62(18) . . ?
C4 C3 H3 120.2 . . ?
O1 C4 C3 125.02(18) . . ?
O1 C4 C5 115.15(18) . . ?
C3 C4 C5 119.83(19) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.41(19) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.39(18) . . ?
C5 C6 H6 119.8 . . ?
C8 C7 N2 115.75(17) . . ?
C8 C7 C12 119.4(2) . . ?
C12 C7 N2 124.81(19) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.3(2) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.7(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.7 . . ?
C12 C11 C10 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C7 C12 H12 120.1 . . ?
C11 C12 C7 119.8(2) . . ?
C11 C12 H12 120.1 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O1 C4 C5 C6 -179.6(2) . . . . ?
N1 N2 C7 C8 -178.66(18) . . . . ?
N1 N2 C7 C12 0.5(3) . . . . ?
N1 C1 C2 C3 179.91(19) . . . . ?
N1 C1 C6 C5 179.67(19) . . . . ?
N2 N1 C1 C2 176.08(18) . . . . ?
N2 N1 C1 C6 -4.7(3) . . . . ?
N2 C7 C8 C9 179.1(2) . . . . ?
N2 C7 C12 C11 -179.2(2) . . . . ?
C1 N1 N2 C7 178.69(15) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C3 C4 O1 179.2(2) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C1 0.4(3) . . . . ?
C6 C1 C2 C3 0.6(3) . . . . ?
C7 C8 C9 C10 0.3(4) . . . . ?
C8 C7 C12 C11 0.0(3) . . . . ?
C8 C9 C10 C11 -0.3(5) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C7 0.0(4) . . . . ?
C12 C7 C8 C9 -0.1(4) . . . . ?
C13 O1 C4 C3 8.6(3) . . . . ?
C13 O1 C4 C5 -171.1(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Mitegen loop'
_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 1.329
_oxdiff_exptl_absorpt_empirical_full_min 0.690
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jg154_1_100_00
_database_code_depnum_ccdc_archive 'CCDC 2109118'
loop_
_audit_author_name
_audit_author_address
'Nathan Halcovitch'
;Lancaster University
United Kingdom
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12.843 H11.528 N2 O0.871'
_chemical_formula_sum            'C12.84 H11.53 N2 O0.87'
_chemical_formula_weight         207.80
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 N2 O1'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.3562(4)
_cell_length_b                   12.2190(3)
_cell_length_c                   7.2704(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1097.69(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5214
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1550
_cell_measurement_theta_min      5.0750
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8429
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.183
_diffrn_reflns_theta_min         5.091
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  28.00   1.00    2.00    --  -42.28  57.00  30.00   97
  2  ω   -112.00 -16.00   1.00    2.00    --  -42.28 -57.00-120.00   96
  3  ω    -87.00  -6.00   1.00    2.00    --  -42.28 125.00  60.00   81
  4  ω     36.00 109.00   1.00    8.00    --  111.00-111.00 -30.00   73
  5  ω    103.00 178.00   1.00    8.00    --  111.00  77.00 -60.00   75
  6  ω     41.00 139.00   1.00    8.00    --  111.00 -61.00 -60.00   98
  7  ω    103.00 178.00   1.00    8.00    --  111.00  77.00-150.00   75
  8  ω    103.00 178.00   1.00    8.00    --  111.00  77.00 -30.00   75
  9  ω    103.00 178.00   1.00    8.00    --  111.00  77.00-120.00   75
 10  ω    103.00 178.00   1.00    8.00    --  111.00  77.00  90.00   75
 11  ω     30.00 107.00   1.00    8.00    --  111.00 -94.00 150.00   77
 12  ω    103.00 178.00   1.00    8.00    --  111.00  77.00 150.00   75
 13  ω   -112.00 -16.00   1.00    2.00    --  -42.28 -57.00  60.00   96
 14  ω   -112.00 -16.00   1.00    2.00    --  -42.28 -57.00 -30.00   96
 15  ω     87.00 178.00   1.00    8.00    --  111.00  30.00  60.00   91
 16  ω     66.00 124.00   1.00    8.00    --  111.00  15.00-150.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0543650000
_diffrn_orient_matrix_UB_12      0.0965144000
_diffrn_orient_matrix_UB_13      0.0978379000
_diffrn_orient_matrix_UB_21      0.0474737000
_diffrn_orient_matrix_UB_22      0.1853790000
_diffrn_orient_matrix_UB_23      -0.0377408000
_diffrn_orient_matrix_UB_31      -0.1016502000
_diffrn_orient_matrix_UB_32      0.0347875000
_diffrn_orient_matrix_UB_33      -0.0700397000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.827
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                2183
_reflns_number_total             2247
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 962 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.097
_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)+(0.0562P)²+0.1033P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1018
_refine_special_details          ?
_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
2. Others
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72396(13) 0.10950(15) 0.5389(2) 0.0498(6) Uani 0.871(5) 1 d . . . . .
N1 N 0.64890(14) 0.55271(16) 0.4575(2) 0.0471(4) Uani 1 1 d . . . . .
N2 N 0.56541(13) 0.58943(15) 0.5332(2) 0.0451(4) Uani 1 1 d . . . . .
C1 C 0.66612(16) 0.43898(19) 0.4828(2) 0.0453(5) Uani 1 1 d . . . . .
C2 C 0.75480(16) 0.39401(19) 0.3935(3) 0.0466(5) Uani 1 1 d . . . . .
H2 H 0.7999 0.4396 0.3205 0.056 Uiso 1 1 calc R U . . .
C3 C 0.77862(15) 0.28394(19) 0.4091(3) 0.0479(5) Uani 1 1 d . . . . .
H3 H 0.8402 0.2543 0.3488 0.057 Uiso 1 1 calc R U . . .
C4 C 0.71150(16) 0.21669(18) 0.5143(2) 0.0465(5) Uani 1 1 d . . . . .
C5 C 0.62343(18) 0.2623(2) 0.6060(3) 0.0537(5) Uani 1 1 d . . . . .
H5 H 0.5780 0.2168 0.6785 0.064 Uiso 1 1 calc R U . . .
C6 C 0.60142(17) 0.3712(2) 0.5932(3) 0.0518(5) Uani 1 1 d . . . . .
H6 H 0.5421 0.4013 0.6592 0.062 Uiso 1 1 calc R U . . .
C7 C 0.55065(15) 0.70400(17) 0.5098(2) 0.0432(4) Uani 1 1 d . . . . .
C8 C 0.45957(15) 0.74841(19) 0.5939(3) 0.0481(5) Uani 1 1 d . . . . .
H8 H 0.4116 0.7023 0.6605 0.058 Uiso 1 1 calc R U . . .
C9 C 0.43846(17) 0.85961(19) 0.5812(3) 0.0529(5) Uani 1 1 d . . . . .
H9 H 0.3762 0.8895 0.6390 0.064 Uiso 1 1 calc R U . . .
C10 C 0.50836(19) 0.9272(2) 0.4841(4) 0.0553(5) Uani 1 1 d . . . . .
H10 H 0.4944 1.0035 0.4754 0.066 Uiso 1 1 calc R U . . .
C11 C 0.59885(19) 0.8824(2) 0.3997(3) 0.0551(5) Uani 1 1 d . . . . .
H11 H 0.6463 0.9286 0.3323 0.066 Uiso 1 1 calc R U . . .
C12 C 0.62108(17) 0.77241(19) 0.4118(3) 0.0494(5) Uani 1 1 d . . . . .
H12 H 0.6837 0.7430 0.3543 0.059 Uiso 1 1 calc R U . . .
C13 C 0.8208(2) 0.0612(2) 0.4745(4) 0.0529(8) Uani 0.843(7) 1 d . . P . .
H13A H 0.8222 0.0636 0.3398 0.079 Uiso 0.843(7) 1 calc R U P . .
H13B H 0.8243 -0.0151 0.5156 0.079 Uiso 0.843(7) 1 calc R U P . .
H13C H 0.8830 0.1015 0.5234 0.079 Uiso 0.843(7) 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C4 1.331(3) . ?
O1 C13 1.414(3) . ?
N1 N2 1.252(2) . ?
N1 C1 1.418(3) . ?
N2 C7 1.422(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.403(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(3) . ?
C4 C5 1.393(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.361(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(3) . ?
C7 C12 1.401(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.388(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.375(3) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C4 O1 C13 117.67(19) . . ?
N2 N1 C1 114.69(17) . . ?
N1 N2 C7 113.94(17) . . ?
C2 C1 N1 116.48(18) . . ?
C2 C1 C6 118.9(2) . . ?
C6 C1 N1 124.58(18) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.04(19) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.44(18) . . ?
C4 C3 H3 120.3 . . ?
O1 C4 C3 125.76(19) . . ?
O1 C4 C5 114.83(19) . . ?
C5 C4 C3 119.4(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.99(19) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.15(18) . . ?
C5 C6 H6 119.9 . . ?
C8 C7 N2 115.79(18) . . ?
C8 C7 C12 119.6(2) . . ?
C12 C7 N2 124.65(18) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.34(19) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0(2) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.5(2) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C7 C12 H12 120.3 . . ?
C11 C12 C7 119.5(2) . . ?
C11 C12 H12 120.3 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O1 C4 C5 C6 179.79(19) . . . . ?
N1 N2 C7 C8 -179.14(17) . . . . ?
N1 N2 C7 C12 0.1(2) . . . . ?
N1 C1 C2 C3 -179.92(17) . . . . ?
N1 C1 C6 C5 178.7(2) . . . . ?
N2 N1 C1 C2 176.88(17) . . . . ?
N2 N1 C1 C6 -4.4(3) . . . . ?
N2 C7 C8 C9 179.26(17) . . . . ?
N2 C7 C12 C11 -179.48(19) . . . . ?
C1 N1 N2 C7 178.69(14) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C1 C6 C5 -2.5(3) . . . . ?
C2 C3 C4 O1 179.03(19) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C1 1.6(3) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C7 C12 C11 -0.3(3) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C11 C12 C7 0.6(3) . . . . ?
C12 C7 C8 C9 0.0(3) . . . . ?
C13 O1 C4 C3 9.0(3) . . . . ?
C13 O1 C4 C5 -170.1(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Mitegen loop'
_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 1.155
_oxdiff_exptl_absorpt_empirical_full_min 0.841
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jg154_2_140_00
_database_code_depnum_ccdc_archive 'CCDC 2109119'
loop_
_audit_author_name
_audit_author_address
'Nathan Halcovitch'
;Lancaster University
United Kingdom
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12.844 H11.533 N2 O0.872'
_chemical_formula_sum            'C12.85 H11.53 N2 O0.87'
_chemical_formula_weight         207.87
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 N2 O1'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.3815(3)
_cell_length_b                   12.2324(3)
_cell_length_c                   7.30180(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1105.90(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5195
_cell_measurement_temperature    140.01(10)
_cell_measurement_theta_max      75.9480
_cell_measurement_theta_min      3.5580
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             438
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0145
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8527
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.178
_diffrn_reflns_theta_min         5.083
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      140.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  28.00   1.00    2.00    --  -42.28  57.00  30.00   97
  2  ω   -112.00 -16.00   1.00    2.00    --  -42.28 -57.00-120.00   96
  3  ω    -87.00  -6.00   1.00    2.00    --  -42.28 125.00  60.00   81
  4  ω     36.00 109.00   1.00    8.00    --  111.00-111.00 -30.00   73
  5  ω    103.00 178.00   1.00    8.00    --  111.00  77.00 -60.00   75
  6  ω     41.00 139.00   1.00    8.00    --  111.00 -61.00 -60.00   98
  7  ω    103.00 178.00   1.00    8.00    --  111.00  77.00-150.00   75
  8  ω    103.00 178.00   1.00    8.00    --  111.00  77.00 -30.00   75
  9  ω    103.00 178.00   1.00    8.00    --  111.00  77.00-120.00   75
 10  ω    103.00 178.00   1.00    8.00    --  111.00  77.00  90.00   75
 11  ω     30.00 107.00   1.00    8.00    --  111.00 -94.00 150.00   77
 12  ω    103.00 178.00   1.00    8.00    --  111.00  77.00 150.00   75
 13  ω   -112.00 -16.00   1.00    2.00    --  -42.28 -57.00  60.00   96
 14  ω   -112.00 -16.00   1.00    2.00    --  -42.28 -57.00 -30.00   96
 15  ω     87.00 178.00   1.00    8.00    --  111.00  30.00  60.00   91
 16  ω     66.00 124.00   1.00    8.00    --  111.00  15.00-150.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0521798000
_diffrn_orient_matrix_UB_12      -0.0963751000
_diffrn_orient_matrix_UB_13      0.0987751000
_diffrn_orient_matrix_UB_21      -0.0480041000
_diffrn_orient_matrix_UB_22      -0.1840055000
_diffrn_orient_matrix_UB_23      -0.0379912000
_diffrn_orient_matrix_UB_31      0.1022712000
_diffrn_orient_matrix_UB_32      -0.0371003000
_diffrn_orient_matrix_UB_33      -0.0682132000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.826
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                2167
_reflns_number_total             2270
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.096
_refine_diff_density_min         -0.122
_refine_diff_density_rms         0.024
_refine_ls_abs_structure_details 
;
 Flack x determined using 962 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2270
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0313
_refine_ls_restrained_S_all      1.064
_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)+(0.0512P)²+0.0848P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0927
_refine_special_details          ?
_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
2. Others
 Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
3.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.72497(12) 0.11038(13) 0.4619(2) 0.0545(5) Uani 0.872(5) 1 d . . . . .
N1 N 0.64854(14) 0.55289(14) 0.5425(2) 0.0503(4) Uani 1 1 d . . . . .
N2 N 0.56536(12) 0.58932(13) 0.46735(19) 0.0481(4) Uani 1 1 d . . . . .
C1 C 0.66601(15) 0.43924(17) 0.5173(2) 0.0478(4) Uani 1 1 d . . . . .
C2 C 0.75451(15) 0.39475(17) 0.6067(2) 0.0503(4) Uani 1 1 d . . . . .
H2 H 0.7993 0.4405 0.6795 0.060 Uiso 1 1 calc R U . . .
C3 C 0.77849(15) 0.28473(17) 0.5915(2) 0.0514(4) Uani 1 1 d . . . . .
H3 H 0.8398 0.2552 0.6523 0.062 Uiso 1 1 calc R U . . .
C4 C 0.71211(15) 0.21756(16) 0.4864(2) 0.0496(4) Uani 1 1 d . . . . .
C5 C 0.62416(16) 0.26255(18) 0.3946(2) 0.0575(5) Uani 1 1 d . . . . .
H5 H 0.5792 0.2168 0.3222 0.069 Uiso 1 1 calc R U . . .
C6 C 0.60174(16) 0.37146(17) 0.4075(3) 0.0550(5) Uani 1 1 d . . . . .
H6 H 0.5425 0.4014 0.3418 0.066 Uiso 1 1 calc R U . . .
C7 C 0.55048(14) 0.70400(15) 0.4903(2) 0.0462(4) Uani 1 1 d . . . . .
C8 C 0.45972(15) 0.74804(17) 0.4068(2) 0.0526(4) Uani 1 1 d . . . . .
H8 H 0.4118 0.7019 0.3409 0.063 Uiso 1 1 calc R U . . .
C9 C 0.43856(17) 0.85920(18) 0.4192(3) 0.0594(5) Uani 1 1 d . . . . .
H9 H 0.3764 0.8891 0.3617 0.071 Uiso 1 1 calc R U . . .
C10 C 0.50832(19) 0.92651(18) 0.5157(3) 0.0616(5) Uani 1 1 d . . . . .
H10 H 0.4944 1.0027 0.5241 0.074 Uiso 1 1 calc R U . . .
C11 C 0.59839(18) 0.88212(19) 0.5997(3) 0.0607(5) Uani 1 1 d . . . . .
H11 H 0.6457 0.9284 0.6667 0.073 Uiso 1 1 calc R U . . .
C12 C 0.62060(16) 0.77195(18) 0.5877(2) 0.0536(5) Uani 1 1 d . . . . .
H12 H 0.6830 0.7425 0.6452 0.064 Uiso 1 1 calc R U . . .
C13 C 0.8213(2) 0.0624(2) 0.5265(4) 0.0598(8) Uani 0.844(6) 1 d . . P . .
H13A H 0.8834 0.1028 0.4782 0.090 Uiso 0.844(6) 1 calc R U P . .
H13B H 0.8250 -0.0138 0.4855 0.090 Uiso 0.844(6) 1 calc R U P . .
H13C H 0.8224 0.0648 0.6606 0.090 Uiso 0.844(6) 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C4 1.333(2) . ?
O1 C13 1.410(3) . ?
N1 N2 1.249(2) . ?
N1 C1 1.419(2) . ?
N2 C7 1.425(2) . ?
C1 C2 1.387(3) . ?
C1 C6 1.401(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.393(3) . ?
C4 C5 1.392(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.364(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(3) . ?
C7 C12 1.397(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.388(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.378(3) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C4 O1 C13 117.76(18) . . ?
N2 N1 C1 114.74(15) . . ?
N1 N2 C7 113.97(15) . . ?
C2 C1 N1 116.36(17) . . ?
C2 C1 C6 119.08(18) . . ?
C6 C1 N1 124.55(16) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.92(18) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.46(17) . . ?
C4 C3 H3 120.3 . . ?
O1 C4 C3 125.72(17) . . ?
O1 C4 C5 114.69(17) . . ?
C5 C4 C3 119.59(18) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.82(17) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.10(17) . . ?
C5 C6 H6 119.9 . . ?
C8 C7 N2 115.80(16) . . ?
C8 C7 C12 119.75(18) . . ?
C12 C7 N2 124.44(17) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.31(18) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 H12 120.3 . . ?
C11 C12 C7 119.35(19) . . ?
C11 C12 H12 120.3 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O1 C4 C5 C6 -179.86(18) . . . . ?
N1 N2 C7 C8 179.17(16) . . . . ?
N1 N2 C7 C12 -0.3(2) . . . . ?
N1 C1 C2 C3 179.85(16) . . . . ?
N1 C1 C6 C5 -178.86(18) . . . . ?
N2 N1 C1 C2 -176.73(16) . . . . ?
N2 N1 C1 C6 4.4(2) . . . . ?
N2 C7 C8 C9 -179.25(17) . . . . ?
N2 C7 C12 C11 179.50(18) . . . . ?
C1 N1 N2 C7 -178.57(14) . . . . ?
C1 C2 C3 C4 -0.7(3) . . . . ?
C2 C1 C6 C5 2.3(3) . . . . ?
C2 C3 C4 O1 -179.14(18) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C6 C1 C2 C3 -1.2(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 C12 0.6(4) . . . . ?
C10 C11 C12 C7 -0.5(3) . . . . ?
C12 C7 C8 C9 0.2(3) . . . . ?
C13 O1 C4 C3 -9.1(3) . . . . ?
C13 O1 C4 C5 170.28(19) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Mitegen loop'
_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 1.147
_oxdiff_exptl_absorpt_empirical_full_min 0.847
_exptl_crystal_recrystallization_method 'From the Melt'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_jg153_4_220_00
_database_code_depnum_ccdc_archive 'CCDC 2109115'
loop_
_audit_author_name
_audit_author_address
'Nathan Halcovitch'
;Lancaster University
United Kingdom
;
_audit_update_record             
;
2021-09-10 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_audit_creation_date             2021-08-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6383)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H12 N2 O'
_chemical_formula_sum            'C13 H12 N2 O'
_chemical_formula_weight         212.25
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C13 H12 N2 O1'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.6025(2)
_cell_length_b                   12.2998(2)
_cell_length_c                   7.35020(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1139.34(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6122
_cell_measurement_temperature    220.00(10)
_cell_measurement_theta_max      75.9380
_cell_measurement_theta_min      5.0140
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.939
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_unetI/netI     0.0127
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8765
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.284
_diffrn_reflns_theta_min         5.024
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2282
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00    3.00    --  -42.28 125.00  30.00   81
  2  ω   -112.00 -16.00   1.00    3.00    --  -42.28 -57.00 120.00   96
  3  ω    -69.00  28.00   1.00    3.00    --  -42.28  57.00 -90.00   97
  4  ω     61.00 146.00   1.00   12.00    --  111.00 178.00 150.00   85
  5  ω    103.00 178.00   1.00   12.00    --  111.00  77.00  90.00   75
  6  ω     87.00 178.00   1.00   12.00    --  111.00  45.00 -30.00   91
  7  ω     40.00 135.00   1.00   12.00    --  111.00 -45.00  60.00   95
  8  ω    104.00 178.00   1.00   12.00    --  111.00 111.00 120.00   74
  9  ω     61.00 146.00   1.00   12.00    --  111.00 178.00 120.00   85
 10  ω     83.00 178.00   1.00   12.00    --  111.00  61.00-120.00   95
 11  ω     87.00 178.00   1.00   12.00    --  111.00  30.00 -60.00   91
 12  ω    103.00 178.00   1.00   12.00    --  111.00  77.00-180.00   75
 13  ω   -112.00 -16.00   1.00    3.00    --  -42.28 -57.00   0.00   96
 14  ω   -115.00 -20.00   1.00    3.00    --  -42.28 -38.00 150.00   95
 15  ω   -112.00 -16.00   1.00    3.00    --  -42.28 -57.00-120.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0413294000
_diffrn_orient_matrix_UB_12      0.0779344000
_diffrn_orient_matrix_UB_13      0.1084006000
_diffrn_orient_matrix_UB_21      0.0746895000
_diffrn_orient_matrix_UB_22      -0.1645715000
_diffrn_orient_matrix_UB_23      0.0124546000
_diffrn_orient_matrix_UB_31      0.0875145000
_diffrn_orient_matrix_UB_32      0.1037469000
_diffrn_orient_matrix_UB_33      -0.0615071000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    0.962
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                2216
_reflns_number_total             2297
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.095
_refine_diff_density_rms         0.022
_refine_ls_abs_structure_details 
;
 Flack x determined using 965 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(7)
_refine_ls_extinction_coef       0.0089(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2297
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0283
_refine_ls_restrained_S_all      1.034
_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)+(0.0496P)²+0.0636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0835
_refine_special_details          ?
_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
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.27238(10) 0.11279(10) 0.46215(17) 0.0633(4) Uani 1 1 d . . . . .
N1 N 0.35329(11) 0.55396(11) 0.54194(18) 0.0532(3) Uani 1 1 d . . . . .
N2 N 0.43472(10) 0.58960(11) 0.46702(17) 0.0505(3) Uani 1 1 d . . . . .
C1 C 0.33514(12) 0.44109(13) 0.5168(2) 0.0481(3) Uani 1 1 d . . . . .
C2 C 0.24866(13) 0.39761(15) 0.6079(2) 0.0554(4) Uani 1 1 d . . . . .
H2 H 0.2063 0.4429 0.6809 0.067 Uiso 1 1 calc R U . . .
C3 C 0.22401(12) 0.28820(15) 0.5927(2) 0.0548(4) Uani 1 1 d . . . . .
H3 H 0.1649 0.2595 0.6541 0.066 Uiso 1 1 calc R U . . .
C4 C 0.28732(12) 0.22130(13) 0.48620(19) 0.0502(4) Uani 1 1 d . . . . .
C5 C 0.37384(12) 0.26513(14) 0.3927(2) 0.0552(4) Uani 1 1 d . . . . .
H5 H 0.4163 0.2199 0.3197 0.066 Uiso 1 1 calc R U . . .
C6 C 0.39722(12) 0.37338(14) 0.4067(2) 0.0527(4) Uani 1 1 d . . . . .
H6 H 0.4551 0.4024 0.3423 0.063 Uiso 1 1 calc R U . . .
C7 C 0.45029(12) 0.70366(12) 0.48966(19) 0.0486(3) Uani 1 1 d . . . . .
C8 C 0.53848(13) 0.74672(14) 0.4045(2) 0.0582(4) Uani 1 1 d . . . . .
H8 H 0.5841 0.7011 0.3380 0.070 Uiso 1 1 calc R U . . .
C9 C 0.55987(17) 0.85707(15) 0.4170(3) 0.0712(5) Uani 1 1 d . . . . .
H9 H 0.6200 0.8862 0.3590 0.085 Uiso 1 1 calc R U . . .
C10 C 0.49296(18) 0.92406(16) 0.5145(4) 0.0729(5) Uani 1 1 d . . . . .
H10 H 0.5072 0.9989 0.5226 0.088 Uiso 1 1 calc R U . . .
C11 C 0.40526(16) 0.88085(16) 0.5999(3) 0.0705(5) Uani 1 1 d . . . . .
H11 H 0.3602 0.9266 0.6673 0.085 Uiso 1 1 calc R U . . .
C12 C 0.38272(14) 0.77158(15) 0.5878(2) 0.0587(4) Uani 1 1 d . . . . .
H12 H 0.3222 0.7430 0.6453 0.070 Uiso 1 1 calc R U . . .
C13 C 0.17866(17) 0.06541(17) 0.5304(3) 0.0759(6) Uani 1 1 d . . . . .
H13A H 0.1176 0.1041 0.4827 0.114 Uiso 1 1 calc R U . . .
H13B H 0.1786 0.0697 0.6621 0.114 Uiso 1 1 calc R U . . .
H13C H 0.1753 -0.0102 0.4933 0.114 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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 C4 1.3595(19) . ?
O1 C13 1.409(2) . ?
N1 N2 1.2444(18) . ?
N1 C1 1.4192(19) . ?
N2 C7 1.4263(19) . ?
C1 C2 1.387(2) . ?
C1 C6 1.400(2) . ?
C2 H2 0.9400 . ?
C2 C3 1.386(2) . ?
C3 H3 0.9400 . ?
C3 C4 1.388(2) . ?
C4 C5 1.397(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.368(2) . ?
C6 H6 0.9400 . ?
C7 C8 1.381(2) . ?
C7 C12 1.394(2) . ?
C8 H8 0.9400 . ?
C8 C9 1.387(2) . ?
C9 H9 0.9400 . ?
C9 C10 1.380(3) . ?
C10 H10 0.9400 . ?
C10 C11 1.378(3) . ?
C11 H11 0.9400 . ?
C11 C12 1.377(3) . ?
C12 H12 0.9400 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?

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
C4 O1 C13 118.41(15) . . ?
N2 N1 C1 114.82(12) . . ?
N1 N2 C7 114.09(13) . . ?
C2 C1 N1 116.17(14) . . ?
C2 C1 C6 119.27(15) . . ?
C6 C1 N1 124.55(13) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.79(15) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.50(14) . . ?
C4 C3 H3 120.3 . . ?
O1 C4 C3 125.16(13) . . ?
O1 C4 C5 115.02(14) . . ?
C3 C4 C5 119.82(14) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.45(14) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.15(14) . . ?
C5 C6 H6 119.9 . . ?
C8 C7 N2 115.79(14) . . ?
C8 C7 C12 119.75(15) . . ?
C12 C7 N2 124.46(14) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.13(16) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.00(19) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.78(18) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.84(18) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 120.2 . . ?
C11 C12 C7 119.51(17) . . ?
C11 C12 H12 120.2 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O1 C4 C5 C6 -179.75(15) . . . . ?
N1 N2 C7 C8 -178.44(14) . . . . ?
N1 N2 C7 C12 0.7(2) . . . . ?
N1 C1 C2 C3 -179.93(14) . . . . ?
N1 C1 C6 C5 179.34(15) . . . . ?
N2 N1 C1 C2 176.12(14) . . . . ?
N2 N1 C1 C6 -4.5(2) . . . . ?
N2 C7 C8 C9 179.35(16) . . . . ?
N2 C7 C12 C11 -179.65(16) . . . . ?
C1 N1 N2 C7 178.44(12) . . . . ?
C1 C2 C3 C4 0.6(2) . . . . ?
C2 C1 C6 C5 -1.3(2) . . . . ?
C2 C3 C4 O1 179.14(15) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C6 C1 C2 C3 0.7(2) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C8 C7 C12 C11 -0.5(3) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?
C9 C10 C11 C12 -0.7(4) . . . . ?
C10 C11 C12 C7 0.8(3) . . . . ?
C12 C7 C8 C9 0.1(3) . . . . ?
C13 O1 C4 C3 8.5(2) . . . . ?
C13 O1 C4 C5 -171.12(17) . . . . ?

_olex2_exptl_crystal_mounting_method 'mounted on a Mitegen loop'
_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 1.318
_oxdiff_exptl_absorpt_empirical_full_min 0.699
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
