# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 2454333'
_audit_update_record             
;
2025-05-27 deposited with the CCDC.	2025-08-08 downloaded from the CCDC.
;
_audit_creation_date             2024-02-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C12 H12 N2), 8(H3 N)'
_chemical_formula_sum            'C36 H60 N14'
_chemical_formula_weight         688.98
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 '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      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   20.5422(7)
_cell_length_b                   20.5422(7)
_cell_length_c                   7.9574(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2908.0(3)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    3101
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      51.086
_cell_measurement_theta_min      3.744
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7501
_exptl_absorpt_correction_T_min  0.4533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1276 before and 0.0599 after correction.
The Ratio of minimum to maximum transmission is 0.6043.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1122
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8389
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.349
_diffrn_reflns_theta_max         24.349
_diffrn_reflns_theta_min         1.983
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                770
_reflns_number_total             1066
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         1066
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0684
_refine_ls_restrained_S_all      1.163
_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)+(0.1164P)²+1.9318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1910
_refine_ls_wR_factor_ref         0.2148
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All N(H,H,H) groups
2. Restrained distances
 H3A-N3 = N3-H3B
 0.9 with sigma of 0.02
 H2C-N2 = N2-H2A
 0.9 with sigma of 0.02
 H3A-N3 = N3-H3C
 0.9 with sigma of 0.02
 H3B-N3 = N3-H3C
 0.9 with sigma of 0.02
 H2C-N2 = N2-H2B
 0.9 with sigma of 0.02
 H2A-N2 = N2-H2B
 0.9 with sigma of 0.02
 H3A-H3C
 1.465 with sigma of 0.04
 H3A-H3B
 1.465 with sigma of 0.04
 H2C-H2A
 1.465 with sigma of 0.04
 H3B-H3C
 1.465 with sigma of 0.04
 H2C-H2B
 1.465 with sigma of 0.04
 H2A-H2B
 1.465 with sigma of 0.04
3. Others
 Fixed Sof: H3B(0.333333) H3C(0.333333)
4.a Everything fixed:
 H2A, H2B, H2C, H3A, H3B, H3C
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.48062(14) 0.09935(15) 0.5080(3) 0.0720(8) Uani 1 1 d . . . . .
C1 C 0.43421(17) 0.02671(19) 0.4762(4) 0.0729(8) Uani 1 1 d . . . . .
H1 H 0.405131 -0.003751 0.564220 0.087 Uiso 1 1 calc R U . . .
C2 C 0.52061(18) 0.14049(18) 0.3777(4) 0.0769(9) Uani 1 1 d . . . . .
H2 H 0.553818 0.191331 0.395940 0.092 Uiso 1 1 calc R U . . .
C3 C 0.51633(17) 0.11316(17) 0.2179(4) 0.0722(8) Uani 1 1 d . . . . .
H3 H 0.544871 0.145296 0.131497 0.087 Uiso 1 1 calc R U . . .
C4 C 0.46915(14) 0.03739(16) 0.1867(3) 0.0613(8) Uani 1 1 d . . . . .
C5 C 0.42671(15) -0.00591(17) 0.3214(4) 0.0676(8) Uani 1 1 d . . . . .
H5 H 0.393229 -0.056962 0.306832 0.081 Uiso 1 1 calc R U . . .
C6 C 0.46618(16) 0.00470(18) 0.0159(4) 0.0692(8) Uani 1 1 d . . . . .
H6A H 0.464239 0.037430 -0.069407 0.083 Uiso 1 1 calc R U . . .
H6B H 0.420695 -0.043834 0.006758 0.083 Uiso 1 1 calc R U . . .
N2 N 0.54424(17) 0.19203(17) 0.7978(4) 0.0930(10) Uani 1 1 d D . . . .
H2A H 0.571170 0.221860 0.734180 0.140 Uiso 1 1 d D U . . .
H2B H 0.520020 0.153540 0.728930 0.140 Uiso 1 1 d D U . . .
H2C H 0.513630 0.202200 0.862560 0.140 Uiso 1 1 d D U . . .
N3 N 0.666667 0.333333 0.1337(9) 0.165(3) Uani 1 3 d DS T P . .
H3A H 0.666670 0.333330 0.246130 0.248 Uiso 0.3333 1 d D U P A -1
H3B H 0.650100 0.286990 0.092160 0.248 Uiso 0.3333 1 d D U P B -1
H3C H 0.712000 0.364930 0.089450 0.248 Uiso 0.3333 1 d D U P C -1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0719(16) 0.0873(18) 0.0663(14) -0.0127(12) -0.0009(11) 0.0468(15)
C1 0.0655(17) 0.085(2) 0.0682(17) -0.0007(14) 0.0043(13) 0.0374(16)
C2 0.0772(19) 0.0693(18) 0.082(2) -0.0162(15) -0.0018(16) 0.0353(16)
C3 0.0764(19) 0.0698(18) 0.0670(17) -0.0051(13) 0.0073(13) 0.0339(15)
C4 0.0537(15) 0.0713(17) 0.0643(16) -0.0121(12) -0.0076(11) 0.0354(13)
C5 0.0576(15) 0.0690(17) 0.0734(17) -0.0054(13) -0.0030(13) 0.0296(14)
C6 0.0635(16) 0.0804(18) 0.0657(17) -0.0189(13) -0.0102(12) 0.0375(14)
N2 0.101(2) 0.103(2) 0.0872(19) -0.0424(16) -0.0253(15) 0.0603(18)
N3 0.177(5) 0.177(5) 0.143(7) 0.000 0.000 0.088(3)

_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
N1 C1 1.333(4) . ?
N1 C2 1.331(4) . ?
C1 H1 0.9300 . ?
C1 C5 1.374(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(4) . ?
C4 C5 1.387(4) . ?
C4 C6 1.504(4) . ?
C5 H5 0.9300 . ?
C6 C6 1.517(6) 10_655 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
N2 H2A 0.7738 . ?
N2 H2B 0.8829 . ?
N2 H2C 0.9144 . ?
N3 H3A 0.8945 . ?
N3 H3B 0.8986 . ?
N3 H3C 0.8990 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 115.6(2) . . ?
N1 C1 H1 118.0 . . ?
N1 C1 C5 124.0(3) . . ?
C5 C1 H1 118.0 . . ?
N1 C2 H2 117.7 . . ?
N1 C2 C3 124.6(3) . . ?
C3 C2 H2 117.7 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 116.4(2) . . ?
C3 C4 C6 120.9(3) . . ?
C5 C4 C6 122.7(3) . . ?
C1 C5 C4 119.9(3) . . ?
C1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C6 C6 111.9(3) . 10_655 ?
C4 C6 H6A 109.2 . . ?
C4 C6 H6B 109.2 . . ?
C6 C6 H6A 109.2 10_655 . ?
C6 C6 H6B 109.2 10_655 . ?
H6A C6 H6B 107.9 . . ?
H2A N2 H2B 99.4 . . ?
H2A N2 H2C 119.3 . . ?
H2B N2 H2C 114.2 . . ?
H3A N3 H3B 111.6 . . ?
H3A N3 H3C 113.1 . . ?
H3B N3 H3C 109.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C5 C4 0.2(4) . . . . ?
N1 C2 C3 C4 -1.8(5) . . . . ?
C1 N1 C2 C3 0.5(5) . . . . ?
C2 N1 C1 C5 0.3(4) . . . . ?
C2 C3 C4 C5 2.2(4) . . . . ?
C2 C3 C4 C6 -176.6(3) . . . . ?
C3 C4 C5 C1 -1.5(4) . . . . ?
C3 C4 C6 C6 76.3(4) . . . 10_655 ?
C5 C4 C6 C6 -102.4(4) . . . 10_655 ?
C6 C4 C5 C1 177.3(2) . . . . ?

_shelx_res_file                  
;
TITL 11_a.res in R-3
    11.res
    created by SHELXL-2018/3 at 11:16:28 on 23-Feb-2024
REM Old TITL 11 in R-3
REM SHELXT solution in R-3
REM R1 0.169, Rweak 0.012, Alpha 0.024, Orientation as input
REM Formula found by SHELXT: C18 N7
CELL 0.71073 20.5422 20.5422 7.9574 90 90 120
ZERR 3 0.0007 0.0007 0.0005 0 0 0
LATT 3
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SFAC C H N
UNIT 108 180 42
DFIX 0.9 H3a N3 N3 H3b
DANG 1.465 H3a H3c
DFIX 0.9 H2c N2 N2 H2a
DANG 1.465 H3a H3b
DANG 1.465 H2c H2a
DFIX 0.9 H3a N3 N3 H3c
DANG 1.465 H3b H3c
DFIX 0.9 H3b N3 N3 H3c
DFIX 0.9 H2c N2 N2 H2b
DANG 1.465 H2c H2b
DANG 1.465 H2a H2b
DFIX 0.9 H2a N2 N2 H2b

L.S. 4 0 0
PLAN  1
SIZE 0.12 0.18 0.2
TEMP 24.85
CONF
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\11.hkl">
REM </olex2.extras>

WGHT    0.116400    1.931800
FVAR       0.45601
N1    3    0.480619    0.099350    0.507980    11.00000    0.07188    0.08727 =
         0.06625   -0.01267   -0.00088    0.04675
C1    1    0.434207    0.026705    0.476215    11.00000    0.06553    0.08464 =
         0.06822   -0.00066    0.00429    0.03737
AFIX  43
H1    2    0.405131   -0.003751    0.564220    11.00000   -1.20000
AFIX   0
C2    1    0.520612    0.140487    0.377652    11.00000    0.07724    0.06933 =
         0.08220   -0.01623   -0.00178    0.03526
AFIX  43
H2    2    0.553818    0.191331    0.395940    11.00000   -1.20000
AFIX   0
C3    1    0.516327    0.113158    0.217866    11.00000    0.07639    0.06984 =
         0.06696   -0.00510    0.00730    0.03393
AFIX  43
H3    2    0.544871    0.145296    0.131497    11.00000   -1.20000
AFIX   0
C4    1    0.469146    0.037386    0.186750    11.00000    0.05370    0.07132 =
         0.06431   -0.01215   -0.00760    0.03544
C5    1    0.426715   -0.005912    0.321353    11.00000    0.05764    0.06899 =
         0.07337   -0.00537   -0.00296    0.02965
AFIX  43
H5    2    0.393229   -0.056962    0.306832    11.00000   -1.20000
AFIX   0
C6    1    0.466184    0.004705    0.015874    11.00000    0.06349    0.08039 =
         0.06568   -0.01892   -0.01024    0.03748
AFIX  23
H6A   2    0.464239    0.037430   -0.069407    11.00000   -1.20000
H6B   2    0.420695   -0.043834    0.006758    11.00000   -1.20000
AFIX   0

N2    3    0.544242    0.192026    0.797797    11.00000    0.10146    0.10281 =
         0.08716   -0.04239   -0.02530    0.06034
AFIX   1
H2A   2    0.571170    0.221860    0.734180    11.00000   -1.50000
AFIX   1
H2B   2    0.520020    0.153540    0.728930    11.00000   -1.50000
AFIX   1
H2C   2    0.513630    0.202200    0.862560    11.00000   -1.50000
AFIX   0

N3    3    0.666667    0.333333    0.133721    10.33333    0.17690    0.17690 =
         0.14250    0.00000    0.00000    0.08845
PART -1
AFIX   1
H3A   2    0.666670    0.333330    0.246130    10.33333   -1.50000
AFIX   1
H3B   2    0.650100    0.286990    0.092160    10.33333   -1.50000
AFIX   1
H3C   2    0.712000    0.364930    0.089450    10.33333   -1.50000
AFIX   0
HKLF 4




REM  11_a.res in R-3
REM wR2 = 0.2148, GooF = S = 1.117, Restrained GooF = 1.163 for all data
REM R1 = 0.0684 for 770 Fo > 4sig(Fo) and 0.0900 for all 1066 data
REM 76 parameters refined using 18 restraints

END

WGHT      0.1164      1.9400

REM Highest difference peak  0.263,  deepest hole -0.311,  1-sigma level  0.058
Q1    1   0.5753  0.1867  0.8354  11.00000  0.05    0.26
;
_shelx_res_checksum              82199
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_20241031_HG
_database_code_depnum_ccdc_archive 'CCDC 2454335'
_audit_update_record             
;
2025-05-27 deposited with the CCDC.	2025-08-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C14 H16 N2'
_chemical_formula_sum            'C14 H16 N2'
_chemical_formula_iupac          ?
_chemical_formula_weight         212.29
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           46
_space_group_name_H-M_alt        'I m a 2'
_space_group_name_Hall           'I 2 -2a'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y, z'
'-x+1/2, y, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1/2, z+1/2'
'-x+1, y+1/2, z+1/2'

_cell_length_a                   7.6005(10)
_cell_length_b                   18.3331(17)
_cell_length_c                   8.5191(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1187.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2323
_cell_measurement_theta_min      5.7269
_cell_measurement_theta_max      66.5786
_cell_measurement_temperature    298.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             456

_exptl_absorpt_coefficient_mu    0.544
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.6207
_exptl_absorpt_correction_T_max  0.7528

_exptl_special_details           
;
;

_diffrn_ambient_temperature      298.(2)

_diffrn_source                   ?
_diffrn_source_type              ?
_diffrn_source_power             0.06
_diffrn_source_current           1.1
_diffrn_source_voltage           50

_diffrn_radiation_probe          ?
_diffrn_radiation_type           Cuk\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device       ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            2469
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_theta_min         4.82
_diffrn_reflns_theta_max         66.66
_diffrn_reflns_theta_full        66.66
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10

_refine_special_details          
;

Refined as a 2-component inversion twin.
;

_reflns_number_total             1039
_reflns_number_gt                895
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_max     0.830
_reflns_Friedel_fraction_full    0.832

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1024
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_number_reflns         1039
_refine_ls_number_parameters     93
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²+0.1006P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.108
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.016(2)
_refine_ls_abs_structure_details 
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.6(15)

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'

_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.75 0.69455(15) 0.5418(6) 0.0714(11) Uani d T P S 1 . .
C C1 0.75 0.19942(16) 0.5645(4) 0.0492(10) Uani d T P S 1 . .
N N2 0.75 0.05378(14) 0.4618(5) 0.0672(11) Uani d T P S 1 . .
C C2 0.5956(4) 0.16230(12) 0.5367(4) 0.0589(8) Uani d . . . 1 . .
H H2 0.487803 0.185291 0.551857 0.071 Uiso calc U . R 1 . .
C C3 0.6016(4) 0.09081(13) 0.4863(4) 0.0665(9) Uani d . . . 1 . .
H H3 0.495467 0.066967 0.46835 0.08 Uiso calc U . R 1 . .
C C4 0.75 0.27782(14) 0.6202(5) 0.0588(10) Uani d T P S 1 . .
H H4A 0.853135 0.286106 0.684901 0.071 Uiso calc U P R 0.5 . .
H H4AB 0.646865 0.286106 0.684901 0.071 Uiso calc U P R 0.5 . .
C C5 0.75 0.33219(15) 0.4852(4) 0.0482(10) Uani d T P S 1 . .
H H5A 0.646794 0.324132 0.420469 0.058 Uiso calc U P R 0.5 . .
H H5AB 0.853206 0.324132 0.420469 0.058 Uiso calc U P R 0.5 . .
C C9 0.75 0.59980(19) 0.3485(5) 0.0641(12) Uani d T P S 1 . .
H H9 0.75 0.587969 0.242329 0.077 Uiso calc U P R 1 . .
C C8 0.75 0.54520(15) 0.4614(5) 0.0482(10) Uani d T P S 1 . .
C C7 0.75 0.46574(16) 0.4127(4) 0.0506(9) Uani d T P S 1 . .
H H7A 0.647165 0.457101 0.347863 0.061 Uiso calc U P R 0.5 . .
H H7AB 0.852835 0.457101 0.347863 0.061 Uiso calc U P R 0.5 . .
C C6 0.75 0.41072(16) 0.5437(4) 0.0490(9) Uani d T P S 1 . .
H H6A 0.646896 0.418473 0.608729 0.059 Uiso calc U P R 0.5 . .
H H6AB 0.853104 0.418473 0.608729 0.059 Uiso calc U P R 0.5 . .
C C10 0.75 0.67163(19) 0.3954(7) 0.0743(14) Uani d T P S 1 . .
H H10 0.75 0.706959 0.317085 0.089 Uiso calc U P R 1 . .
C C11 0.75 0.64197(18) 0.6489(6) 0.0703(13) Uani d T P S 1 . .
H H11 0.75 0.65586 0.753892 0.084 Uiso calc U P R 1 . .
C C12 0.75 0.56823(16) 0.6162(6) 0.0587(10) Uani d T P S 1 . .
H H12 0.75 0.534321 0.697435 0.07 Uiso calc U P R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.076(2) 0.0353(15) 0.103(3) 0 0 -0.0022(19)
C1 0.075(3) 0.0349(16) 0.0378(19) 0 0 0.0021(14)
N2 0.096(3) 0.0378(15) 0.067(2) 0 0 -0.0008(18)
C2 0.0721(18) 0.0411(12) 0.0634(18) 0.0016(10) 0.0021(15) 0.0032(12)
C3 0.084(2) 0.0437(10) 0.072(2) -0.0109(11) -0.0075(18) 0.0010(14)
C4 0.091(3) 0.0341(14) 0.052(2) 0 0 -0.0028(16)
C5 0.059(2) 0.0361(15) 0.050(2) 0 0 -0.0037(15)
C9 0.078(3) 0.0456(17) 0.069(3) 0 0 0.0133(19)
C8 0.046(2) 0.0338(15) 0.065(2) 0 0 0.0029(17)
C7 0.062(2) 0.0373(15) 0.053(2) 0 0 0.0007(15)
C6 0.060(2) 0.0337(14) 0.054(2) 0 0 -0.0011(15)
C10 0.086(4) 0.0403(17) 0.097(4) 0 0 0.020(2)
C11 0.086(3) 0.0436(16) 0.081(3) 0 0 -0.010(2)
C12 0.074(3) 0.0367(14) 0.065(3) 0 0 -0.0026(18)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C10 . 1.316(7) ?
N1 C11 . 1.327(6) ?
C1 C2 . 1.377(3) ?
C1 C2 4_655 1.377(3) ?
C1 C4 . 1.514(4) ?
N2 C3 . 1.333(3) ?
N2 C3 4_655 1.333(3) ?
C2 C3 . 1.380(3) ?
C4 C5 . 1.522(5) ?
C5 C6 . 1.524(3) ?
C9 C10 . 1.376(6) ?
C9 C8 . 1.388(5) ?
C8 C12 . 1.385(7) ?
C8 C7 . 1.515(4) ?
C7 C6 . 1.505(5) ?
C11 C12 . 1.380(4) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 N1 C11 . . 114.8(3) ?
C2 C1 C2 . 4_655 116.9(3) ?
C2 C1 C4 . . 121.54(15) ?
C2 C1 C4 4_655 . 121.54(15) ?
C3 N2 C3 . 4_655 115.6(3) ?
C1 C2 C3 . . 119.6(3) ?
N2 C3 C2 . . 124.1(3) ?
C1 C4 C5 . . 112.6(4) ?
C4 C5 C6 . . 111.8(3) ?
C10 C9 C8 . . 119.3(5) ?
C12 C8 C9 . . 116.1(3) ?
C12 C8 C7 . . 123.6(3) ?
C9 C8 C7 . . 120.3(4) ?
C6 C7 C8 . . 116.2(3) ?
C7 C6 C5 . . 113.0(3) ?
N1 C10 C9 . . 125.5(4) ?
N1 C11 C12 . . 125.0(5) ?
C11 C12 C8 . . 119.4(4) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C2 C1 C2 C3 4_655 . . . 1.2(5) ?
C4 C1 C2 C3 . . . . -179.9(3) ?
C3 N2 C3 C2 4_655 . . . -1.2(7) ?
C1 C2 C3 N2 . . . . 0.0(4) ?
C2 C1 C4 C5 . . . . -89.4(3) ?
C2 C1 C4 C5 4_655 . . . 89.4(3) ?
C1 C4 C5 C6 . . . . 180.0000(10) ?
C10 C9 C8 C12 . . . . 0.000(2) ?
C10 C9 C8 C7 . . . . 180.000(2) ?
C12 C8 C7 C6 . . . . 0.000(2) ?
C9 C8 C7 C6 . . . . 180.0000(10) ?
C8 C7 C6 C5 . . . . 180.0000(10) ?
C4 C5 C6 C7 . . . . 180.0000(10) ?
C11 N1 C10 C9 . . . . 0.000(3) ?
C8 C9 C10 N1 . . . . 0.000(3) ?
C10 N1 C11 C12 . . . . 0.000(3) ?
N1 C11 C12 C8 . . . . 0.000(3) ?
C9 C8 C12 C11 . . . . 0.000(2) ?
C7 C8 C12 C11 . . . . 180.000(2) ?

_shelx_res_file                  
;

TITL 20241031_HG_0m_a.res in Ima2
    20241031_HG_0m_a.res
    created by SHELXL-2018/3 at 15:54:11 on 31-Oct-2024
REM Old TITL 20241031_HG_0m in Imma
REM SHELXT solution in Ima2: R1 0.168, Rweak 0.012, Alpha 0.004
REM <I/s>   0.362 for   18 systematic absences,  Orientation a'=-a, b'=c, c'=b
REM Flack x = -9.990 ( 9.990 ) from   350 Parsons' quotients
REM Formula found by SHELXT:  C8
CELL  1.54178   7.6005  18.3331   8.5191   90.000   90.000   90.000
ZERR   4.000   0.0010   0.0017   0.0011    0.000    0.000    0.000
LATT -2
SYMM -X, -Y, Z
SYMM 1/2+X, -Y, Z
SYMM 1/2-X, Y, Z
SFAC C H N
UNIT 56 64 8
TEMP 24.850
L.S. 10
BOND
HTAB
CONF
ACTA
TWIN
LIST 4
FMAP 2
PLAN 20
WGHT    0.049400    0.100600
EXTI    0.015944
BASF   0.58698
FVAR       1.23777
N1    3    0.750000    0.694553    0.541813    10.50000    0.07588    0.03526 =
         0.10302   -0.00219    0.00000    0.00000
C1    1    0.750000    0.199422    0.564513    10.50000    0.07485    0.03486 =
         0.03783    0.00212    0.00000    0.00000
N2    3    0.750000    0.053782    0.461802    10.50000    0.09640    0.03783 =
         0.06741   -0.00082    0.00000    0.00000
C2    1    0.595551    0.162302    0.536732    11.00000    0.07209    0.04109 =
         0.06340    0.00316    0.00213    0.00157
AFIX  43
H2    2    0.487803    0.185291    0.551857    11.00000   -1.20000
AFIX   0
C3    1    0.601579    0.090805    0.486328    11.00000    0.08374    0.04368 =
         0.07204    0.00103   -0.00750   -0.01095
AFIX  43
H3    2    0.495467    0.066967    0.468350    11.00000   -1.20000
AFIX   0
C4    1    0.750000    0.277824    0.620246    10.50000    0.09089    0.03405 =
         0.05154   -0.00284    0.00000    0.00000
AFIX  23
H4A   2    0.853135    0.286106    0.684901    10.50000   -1.20000
H4AB  2    0.646865    0.286106    0.684901    10.50000   -1.20000
AFIX   0
C5    1    0.750000    0.332185    0.485167    10.50000    0.05871    0.03606 =
         0.04988   -0.00367    0.00000    0.00000
AFIX  23
H5A   2    0.646794    0.324132    0.420469    10.50000   -1.20000
H5AB  2    0.853206    0.324132    0.420469    10.50000   -1.20000
AFIX   0
C9    1    0.750000    0.599795    0.348488    10.50000    0.07782    0.04559 =
         0.06887    0.01327    0.00000    0.00000
AFIX  43
H9    2    0.750000    0.587969    0.242329    10.50000   -1.20000
AFIX   0
C8    1    0.750000    0.545202    0.461366    10.50000    0.04617    0.03376 =
         0.06465    0.00294    0.00000    0.00000
C7    1    0.750000    0.465740    0.412682    10.50000    0.06151    0.03727 =
         0.05288    0.00073    0.00000    0.00000
AFIX  23
H7A   2    0.647165    0.457101    0.347863    10.50000   -1.20000
H7AB  2    0.852835    0.457101    0.347863    10.50000   -1.20000
AFIX   0
C6    1    0.750000    0.410721    0.543732    10.50000    0.05954    0.03373 =
         0.05360   -0.00109    0.00000    0.00000
AFIX  23
H6A   2    0.646896    0.418473    0.608729    10.50000   -1.20000
H6AB  2    0.853104    0.418473    0.608729    10.50000   -1.20000
AFIX   0
C10   1    0.750000    0.671635    0.395433    10.50000    0.08580    0.04026 =
         0.09671    0.01964    0.00000    0.00000
AFIX  43
H10   2    0.750000    0.706959    0.317085    10.50000   -1.20000
AFIX   0
C11   1    0.750000    0.641967    0.648899    10.50000    0.08613    0.04363 =
         0.08104   -0.00993    0.00000    0.00000
AFIX  43
H11   2    0.750000    0.655860    0.753892    10.50000   -1.20000
AFIX   0
C12   1    0.750000    0.568228    0.616237    10.50000    0.07403    0.03672 =
         0.06536   -0.00265    0.00000    0.00000
AFIX  43
H12   2    0.750000    0.534321    0.697435    10.50000   -1.20000
AFIX   0
HKLF 4




REM  20241031_HG_0m_a.res in Ima2
REM wR2 = 0.102367, GooF = S = 1.05836, Restrained GooF = 1.05780 for all data
REM R1 = 0.038075 for 895 Fo > 4sig(Fo) and 0.046059 for all 1039 data
REM 93 parameters refined using 1 restraints

END

WGHT      0.0494      0.1006

REM No hydrogen bonds found for HTAB generation

REM Highest difference peak  0.144,  deepest hole -0.108,  1-sigma level  0.029
Q1    1   0.7500  0.5128  0.4536  10.50000  0.05    0.14
Q2    1   0.7500  0.2917  0.7420  10.50000  0.05    0.13
Q3    1   0.7500  0.7471  0.6041  10.50000  0.05    0.13
Q4    1   0.7500  0.5768  0.4021  10.50000  0.05    0.12
Q5    1   0.7500  0.4348  0.2974  10.50000  0.05    0.11
Q6    1   0.5230  0.0626  0.3897  11.00000  0.05    0.10
Q7    1   0.7500  0.4407  0.4800  10.50000  0.05    0.10
Q8    1   0.7500 -0.0017  0.4175  10.50000  0.05    0.10
Q9    1   0.4938  0.0565  0.5363  11.00000  0.05    0.10
Q10   1   0.7500  0.4225  0.6777  10.50000  0.05    0.09
Q11   1   0.7500  0.3595  0.5562  10.50000  0.05    0.09
Q12   1   0.7500  0.2293  0.5700  10.50000  0.05    0.09
Q13   1   0.7500  0.5517  0.5523  10.50000  0.05    0.09
Q14   1   0.7500  0.3305  0.3515  10.50000  0.05    0.08
Q15   1   0.4937  0.1793  0.6352  11.00000  0.05    0.08
Q16   1   0.7500  0.3487  0.2475  10.50000  0.05    0.08
Q17   1   0.7500  0.3341  0.5263  10.50000  0.05    0.08
Q18   1   0.7500  0.4564  0.6356  10.50000  0.05    0.08
Q19   1   0.7500  0.7082  0.1407  10.50000  0.05    0.07
Q20   1   0.7500  0.6716  0.5890  10.50000  0.05    0.07
;
_shelx_res_checksum              3243
####################################################################### 
# 
# 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_11_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2454334'
_audit_update_record             
;
2025-05-27 deposited with the CCDC.	2025-08-08 downloaded from the CCDC.
;
_audit_creation_date             2024-03-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(H2 O), C10 H8 N4'
_chemical_formula_sum            'C10 H12 N4 O2'
_chemical_formula_weight         220.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.9196(19)
_cell_length_b                   4.7031(8)
_cell_length_c                   11.861(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.888(8)
_cell_angle_gamma                90
_cell_volume                     549.34(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4141
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      57.034
_cell_measurement_theta_min      3.905
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1774 before and 0.0508 after correction.
The Ratio of minimum to maximum transmission is 0.8301.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0332
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6029
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.482
_diffrn_reflns_theta_min         2.068
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1007
_reflns_number_total             1122
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         1122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.095
_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)+(0.0555P)²+0.0899P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1000
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_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 0.46366(9) 0.96142(17) 0.29952(7) 0.0351(3) Uani 1 1 d G . . . .
H1A H 0.500450 1.104004 0.267846 0.053 Uiso 1 1 d G U . . .
H1B H 0.412553 1.039800 0.345516 0.053 Uiso 1 1 d G U . . .
N1 N 0.04552(9) 0.94898(18) 0.53499(7) 0.0256(3) Uani 1 1 d . . . . .
N2 N 0.29414(9) 0.3200(2) 0.41229(8) 0.0287(3) Uani 1 1 d . . . . .
C1 C 0.30685(11) 0.4012(2) 0.52033(10) 0.0305(3) Uani 1 1 d . . . . .
H1 H 0.374667 0.312860 0.572044 0.037 Uiso 1 1 calc R U . . .
C2 C 0.22581(11) 0.6092(2) 0.56154(9) 0.0283(3) Uani 1 1 d . . . . .
H2 H 0.238185 0.661155 0.639499 0.034 Uiso 1 1 calc R U . . .
C3 C 0.12696(10) 0.7386(2) 0.48679(8) 0.0243(3) Uani 1 1 d . . . . .
C4 C 0.11332(10) 0.6590(2) 0.37327(9) 0.0271(3) Uani 1 1 d . . . . .
H4 H 0.047034 0.745277 0.319541 0.033 Uiso 1 1 calc R U . . .
C5 C 0.19916(11) 0.4502(2) 0.34063(9) 0.0283(3) Uani 1 1 d . . . . .
H5 H 0.190123 0.396252 0.262906 0.034 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0454(5) 0.0240(4) 0.0389(5) 0.0029(3) 0.0174(4) 0.0078(3)
N1 0.0254(4) 0.0225(5) 0.0290(5) -0.0001(3) 0.0029(3) 0.0020(3)
N2 0.0283(5) 0.0234(5) 0.0354(5) 0.0004(4) 0.0083(4) 0.0034(3)
C1 0.0284(5) 0.0281(6) 0.0344(6) 0.0013(4) 0.0015(4) 0.0060(4)
C2 0.0291(5) 0.0265(6) 0.0289(5) -0.0021(4) 0.0016(4) 0.0028(4)
C3 0.0234(5) 0.0191(5) 0.0309(5) -0.0003(4) 0.0060(4) -0.0005(4)
C4 0.0271(5) 0.0247(6) 0.0294(5) 0.0026(4) 0.0025(4) 0.0028(4)
C5 0.0319(5) 0.0260(6) 0.0279(5) -0.0009(4) 0.0072(4) 0.0008(4)

_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 H1A 0.8700 . ?
O1 H1B 0.8700 . ?
N1 N1 1.2469(18) 3_576 ?
N1 C3 1.4384(13) . ?
N2 C1 1.3286(15) . ?
N2 C5 1.3391(14) . ?
C1 H1 0.9500 . ?
C1 C2 1.3915(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3819(15) . ?
C3 C4 1.3883(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.3851(15) . ?
C5 H5 0.9500 . ?

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
H1A O1 H1B 104.5 . . ?
N1 N1 C3 113.36(11) 3_576 . ?
C1 N2 C5 117.30(9) . . ?
N2 C1 H1 118.4 . . ?
N2 C1 C2 123.30(10) . . ?
C2 C1 H1 118.4 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 C1 118.66(10) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 N1 115.92(9) . . ?
C2 C3 C4 118.85(9) . . ?
C4 C3 N1 125.23(9) . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.07(9) . . ?
C5 C4 H4 121.0 . . ?
N2 C5 C4 123.80(10) . . ?
N2 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?

_shelx_res_file                  
;
TITL 11_a.res in P2(1)/c
    11.res
    created by SHELXL-2018/3 at 17:12:13 on 12-Mar-2024
REM Old TITL 11 in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.103, Rweak 0.001, Alpha 0.012, Orientation as input
REM Formula found by SHELXT: C5 N2 O
CELL 0.71073 9.9196 4.7031 11.8606 90 96.888 90
ZERR 2 0.0019 0.0008 0.0022 0 0.008 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 20 24 8 4

L.S. 4 0 0
PLAN  5
TEMP -123.15
BOND $H
list 4
fmap 2 53
MORE -1
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\11.hkl">
REM </olex2.extras>

WGHT    0.055500    0.089900
FVAR       1.24745
AFIX   6
O1    4    0.463664    0.961418    0.299524    11.00000    0.04539    0.02395 =
         0.03893    0.00288    0.01742    0.00784
H1A   2    0.500450    1.104004    0.267846    11.00000   -1.50000
H1B   2    0.412553    1.039800    0.345516    11.00000   -1.50000
AFIX   0

N1    3    0.045516    0.948981    0.534990    11.00000    0.02536    0.02251 =
         0.02896   -0.00006    0.00295    0.00205
N2    3    0.294142    0.319961    0.412288    11.00000    0.02833    0.02337 =
         0.03541    0.00041    0.00835    0.00341
C1    1    0.306845    0.401205    0.520328    11.00000    0.02839    0.02808 =
         0.03442    0.00125    0.00154    0.00604
AFIX  43
H1    2    0.374667    0.312860    0.572044    11.00000   -1.20000
AFIX   0
C2    1    0.225806    0.609187    0.561542    11.00000    0.02908    0.02648 =
         0.02893   -0.00206    0.00157    0.00283
AFIX  43
H2    2    0.238185    0.661155    0.639499    11.00000   -1.20000
AFIX   0
C3    1    0.126957    0.738618    0.486788    11.00000    0.02345    0.01912 =
         0.03091   -0.00034    0.00595   -0.00054
C4    1    0.113318    0.659022    0.373272    11.00000    0.02707    0.02471 =
         0.02937    0.00261    0.00253    0.00281
AFIX  43
H4    2    0.047034    0.745277    0.319541    11.00000   -1.20000
AFIX   0
C5    1    0.199157    0.450206    0.340634    11.00000    0.03186    0.02603 =
         0.02785   -0.00088    0.00717    0.00078
AFIX  43
H5    2    0.190123    0.396252    0.262906    11.00000   -1.20000
AFIX   0
HKLF 4




REM  11_a.res in P2(1)/c
REM wR2 = 0.1000, GooF = S = 1.095, Restrained GooF = 1.095 for all data
REM R1 = 0.0349 for 1007 Fo > 4sig(Fo) and 0.0393 for all 1122 data
REM 76 parameters refined using 0 restraints

END

WGHT      0.0555      0.0898

REM Highest difference peak  0.131,  deepest hole -0.240,  1-sigma level  0.051
Q1    1   0.3597  0.2364  0.3809  11.00000  0.05    0.13
Q2    1   0.0755  0.5336  0.5844  11.00000  0.05    0.12
Q3    1   0.3417  0.1839  0.3859  11.00000  0.05    0.12
Q4    1   0.6231  1.0475  0.2757  11.00000  0.05    0.12
Q5    1   0.1449  0.6013  0.5353  11.00000  0.05    0.11
;
_shelx_res_checksum              97561
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_11_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2454336'
_audit_update_record             
;
2025-05-27 deposited with the CCDC.	2025-08-08 downloaded from the CCDC.
;
_audit_creation_date             2024-03-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 N2, H2 O'
_chemical_formula_sum            'C12 H12 N2 O'
_chemical_formula_weight         200.24
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   9.2232(10)
_cell_length_b                   14.7495(15)
_cell_length_c                   7.6284(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1037.75(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8958
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      57.043
_cell_measurement_theta_min      4.920
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1579 before and 0.0623 after correction.
The Ratio of minimum to maximum transmission is 0.7117.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11895
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.413
_diffrn_reflns_theta_min         2.605
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.685
_reflns_Friedel_fraction_full    0.845
_reflns_Friedel_fraction_max     0.797
_reflns_number_gt                1795
_reflns_number_total             1926
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 685 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.7(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1926
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.068
_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)+(0.0611P)²+0.1299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0976
_refine_ls_wR_factor_ref         0.1006
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11),
 C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.5968(2) 0.05568(11) 0.4757(3) 0.0337(5) Uani 1 1 d . . . . .
N2 N 0.6054(2) 0.69436(12) 0.4830(3) 0.0369(5) Uani 1 1 d . . . . .
C1 C 0.4979(2) 0.09427(14) 0.5804(3) 0.0329(5) Uani 1 1 d . . . . .
H1 H 0.436315 0.055766 0.646886 0.040 Uiso 1 1 calc R U . . .
C2 C 0.4802(2) 0.18723(14) 0.5971(3) 0.0302(5) Uani 1 1 d . . . . .
H2 H 0.407382 0.210892 0.672377 0.036 Uiso 1 1 calc R U . . .
C3 C 0.56978(19) 0.24583(14) 0.5031(3) 0.0264(5) Uani 1 1 d . . . . .
C4 C 0.6732(2) 0.20550(13) 0.3931(3) 0.0293(5) Uani 1 1 d . . . . .
H4 H 0.736896 0.242073 0.325455 0.035 Uiso 1 1 calc R U . . .
C5 C 0.6815(2) 0.11266(14) 0.3840(3) 0.0326(5) Uani 1 1 d . . . . .
H5 H 0.751810 0.086991 0.307789 0.039 Uiso 1 1 calc R U . . .
C6 C 0.5529(2) 0.34422(13) 0.5220(3) 0.0271(5) Uani 1 1 d . . . . .
H6 H 0.477194 0.365577 0.595661 0.032 Uiso 1 1 calc R U . . .
C7 C 0.6360(2) 0.40569(13) 0.4434(3) 0.0267(5) Uani 1 1 d . . . . .
H7 H 0.712116 0.383661 0.371127 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6208(2) 0.50413(13) 0.4580(3) 0.0261(4) Uani 1 1 d . . . . .
C9 C 0.4959(2) 0.54767(14) 0.5189(3) 0.0318(5) Uani 1 1 d . . . . .
H9 H 0.413507 0.513340 0.553215 0.038 Uiso 1 1 calc R U . . .
C10 C 0.4937(3) 0.64112(15) 0.5286(3) 0.0351(5) Uani 1 1 d . . . . .
H10 H 0.407829 0.669461 0.570083 0.042 Uiso 1 1 calc R U . . .
C11 C 0.7360(2) 0.55973(13) 0.4062(3) 0.0308(5) Uani 1 1 d . . . . .
H11 H 0.821980 0.533550 0.360014 0.037 Uiso 1 1 calc R U . . .
C12 C 0.7246(3) 0.65233(14) 0.4222(3) 0.0358(5) Uani 1 1 d . . . . .
H12 H 0.805123 0.688488 0.388593 0.043 Uiso 1 1 calc R U . . .
O1 O 0.8649(2) 0.37541(10) 0.1170(3) 0.0479(5) Uani 1 1 d G . . . .
H1A H 0.881623 0.327307 0.054091 0.072 Uiso 1 1 d G U . . .
H1B H 0.878110 0.420447 0.045094 0.072 Uiso 1 1 d G U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0462(9) 0.0222(8) 0.0328(11) -0.0002(8) -0.0087(9) 0.0002(7)
N2 0.0573(11) 0.0235(9) 0.0300(11) 0.0004(8) 0.0006(9) -0.0003(8)
C1 0.0408(11) 0.0266(10) 0.0314(13) 0.0028(9) -0.0037(9) -0.0053(9)
C2 0.0349(10) 0.0269(10) 0.0288(11) 0.0014(9) -0.0005(9) -0.0010(8)
C3 0.0301(9) 0.0231(9) 0.0260(12) -0.0009(9) -0.0058(8) -0.0006(8)
C4 0.0331(10) 0.0255(10) 0.0293(12) -0.0010(9) -0.0019(9) -0.0007(7)
C5 0.0388(11) 0.0270(10) 0.0320(12) -0.0029(10) -0.0046(10) 0.0050(8)
C6 0.0314(10) 0.0234(10) 0.0264(11) -0.0011(8) -0.0012(9) 0.0018(8)
C7 0.0305(9) 0.0233(9) 0.0262(13) -0.0022(9) -0.0003(8) 0.0002(7)
C8 0.0345(10) 0.0235(9) 0.0202(11) 0.0004(9) -0.0025(8) -0.0007(7)
C9 0.0384(10) 0.0268(11) 0.0301(12) 0.0000(9) 0.0036(9) 0.0007(8)
C10 0.0479(12) 0.0262(11) 0.0311(13) 0.0009(10) 0.0045(10) 0.0060(9)
C11 0.0361(10) 0.0279(10) 0.0283(12) 0.0014(9) 0.0009(9) -0.0020(8)
C12 0.0469(12) 0.0297(10) 0.0307(14) 0.0035(9) -0.0020(10) -0.0085(9)
O1 0.0692(12) 0.0276(8) 0.0468(12) -0.0008(8) 0.0187(10) 0.0010(8)

_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
N1 C1 1.339(3) . ?
N1 C5 1.344(3) . ?
N2 C10 1.341(3) . ?
N2 C12 1.344(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.387(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(3) . ?
C3 C4 1.403(3) . ?
C3 C6 1.467(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.330(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.463(3) . ?
C8 C9 1.398(3) . ?
C8 C11 1.399(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.380(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C11 C12 1.375(3) . ?
C12 H12 0.9500 . ?
O1 H1A 0.8701 . ?
O1 H1B 0.8699 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 116.13(17) . . ?
C10 N2 C12 116.58(18) . . ?
N1 C1 H1 118.1 . . ?
N1 C1 C2 123.7(2) . . ?
C2 C1 H1 118.1 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.7(2) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 116.60(19) . . ?
C2 C3 C6 119.99(18) . . ?
C4 C3 C6 123.41(17) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.40(19) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 124.4(2) . . ?
N1 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C3 C6 H6 117.7 . . ?
C7 C6 C3 124.68(19) . . ?
C7 C6 H6 117.7 . . ?
C6 C7 H7 117.0 . . ?
C6 C7 C8 125.94(19) . . ?
C8 C7 H7 117.0 . . ?
C9 C8 C7 124.06(18) . . ?
C9 C8 C11 116.75(18) . . ?
C11 C8 C7 119.18(18) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 C8 119.2(2) . . ?
C10 C9 H9 120.4 . . ?
N2 C10 C9 124.0(2) . . ?
N2 C10 H10 118.0 . . ?
C9 C10 H10 118.0 . . ?
C8 C11 H11 120.0 . . ?
C12 C11 C8 119.9(2) . . ?
C12 C11 H11 120.0 . . ?
N2 C12 C11 123.5(2) . . ?
N2 C12 H12 118.3 . . ?
C11 C12 H12 118.3 . . ?
H1A O1 H1B 104.5 . . ?

_shelx_res_file                  
;
TITL 11_a.res in Pna2(1)
    11.res
    created by SHELXL-2018/3 at 17:08:39 on 12-Mar-2024
REM Old TITL 11 in Pna2(1)
REM SHELXT solution in Pna2(1)
REM R1 0.112, Rweak 0.004, Alpha 0.001, Orientation as input
REM Flack x = -1.546 ( 0.926 ) from Parsons' quotients
REM Formula found by SHELXT: C13 N O
CELL 0.71073 9.2232 14.7495 7.6284 90 90 90
ZERR 4 0.001 0.0015 0.0008 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,+Z
SYMM 0.5-X,0.5+Y,0.5+Z
SFAC C H N O
UNIT 48 48 8 4

L.S. 10
PLAN  5
TEMP -123.15
BOND $H
LIST 4
MORE -1
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\11.hkl">
REM </olex2.extras>

WGHT    0.061100    0.129900
FVAR       1.70718
N1    3    0.596830    0.055681    0.475739    11.00000    0.04619    0.02223 =
         0.03281   -0.00022   -0.00873    0.00017
N2    3    0.605447    0.694356    0.482980    11.00000    0.05729    0.02351 =
         0.03004    0.00036    0.00058   -0.00031
C1    1    0.497888    0.094270    0.580369    11.00000    0.04081    0.02662 =
         0.03139    0.00276   -0.00369   -0.00534
AFIX  43
H1    2    0.436315    0.055766    0.646886    11.00000   -1.20000
AFIX   0
C2    1    0.480211    0.187230    0.597129    11.00000    0.03494    0.02692 =
         0.02881    0.00138   -0.00046   -0.00101
AFIX  43
H2    2    0.407382    0.210892    0.672377    11.00000   -1.20000
AFIX   0
C3    1    0.569775    0.245831    0.503077    11.00000    0.03008    0.02314 =
         0.02598   -0.00091   -0.00578   -0.00062
C4    1    0.673182    0.205496    0.393078    11.00000    0.03310    0.02545 =
         0.02925   -0.00096   -0.00192   -0.00069
AFIX  43
H4    2    0.736896    0.242073    0.325455    11.00000   -1.20000
AFIX   0
C5    1    0.681474    0.112663    0.384035    11.00000    0.03880    0.02705 =
         0.03203   -0.00286   -0.00459    0.00498
AFIX  43
H5    2    0.751810    0.086991    0.307789    11.00000   -1.20000
AFIX   0
C6    1    0.552893    0.344224    0.521987    11.00000    0.03139    0.02341 =
         0.02644   -0.00107   -0.00118    0.00178
AFIX  43
H6    2    0.477194    0.365577    0.595661    11.00000   -1.20000
AFIX   0
C7    1    0.635974    0.405687    0.443377    11.00000    0.03049    0.02332 =
         0.02624   -0.00218   -0.00033    0.00018
AFIX  43
H7    2    0.712116    0.383661    0.371127    11.00000   -1.20000
AFIX   0
C8    1    0.620794    0.504130    0.458025    11.00000    0.03451    0.02351 =
         0.02022    0.00038   -0.00251   -0.00069
C9    1    0.495907    0.547671    0.518905    11.00000    0.03837    0.02681 =
         0.03010   -0.00004    0.00360    0.00071
AFIX  43
H9    2    0.413507    0.513340    0.553215    11.00000   -1.20000
AFIX   0
C10   1    0.493717    0.641118    0.528585    11.00000    0.04792    0.02621 =
         0.03112    0.00094    0.00445    0.00605
AFIX  43
H10   2    0.407829    0.669461    0.570083    11.00000   -1.20000
AFIX   0
C11   1    0.735978    0.559730    0.406213    11.00000    0.03610    0.02790 =
         0.02830    0.00145    0.00085   -0.00204
AFIX  43
H11   2    0.821980    0.533550    0.360014    11.00000   -1.20000
AFIX   0
C12   1    0.724557    0.652328    0.422239    11.00000    0.04688    0.02973 =
         0.03072    0.00351   -0.00201   -0.00850
AFIX  43
H12   2    0.805123    0.688488    0.388593    11.00000   -1.20000
AFIX   6

O1    4    0.864904    0.375406    0.116963    11.00000    0.06923    0.02763 =
         0.04684   -0.00081    0.01868    0.00101
H1A   2    0.881623    0.327307    0.054091    11.00000   -1.50000
H1B   2    0.878110    0.420447    0.045094    11.00000   -1.50000
AFIX   0
HKLF 4




REM  11_a.res in Pna2(1)
REM wR2 = 0.1006, GooF = S = 1.069, Restrained GooF = 1.068 for all data
REM R1 = 0.0376 for 1795 Fo > 4sig(Fo) and 0.0402 for all 1926 data
REM 139 parameters refined using 1 restraints

END

WGHT      0.0611      0.1299

REM Highest difference peak  0.138,  deepest hole -0.239,  1-sigma level  0.044
Q1    1   0.7458  0.3763 -0.0990  11.00000  0.05    0.14
Q2    1   0.8003  0.3852 -0.0800  11.00000  0.05    0.14
Q3    1   0.6063 -0.0156  0.4584  11.00000  0.05    0.13
Q4    1   0.3147  0.3780  0.6507  11.00000  0.05    0.13
Q5    1   0.6280  0.4564  0.5328  11.00000  0.05    0.13
;
_shelx_res_checksum              78012
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_240913lu_lgpz100798_0m
_database_code_depnum_ccdc_archive 'CCDC 2472459'
_audit_update_record             
;
2025-07-14 deposited with the CCDC.	2025-08-08 downloaded from the CCDC.
;
_audit_creation_date             2024-09-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 N2'
_chemical_formula_sum            'C12 H12 N2'
_chemical_formula_weight         184.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.5682(10)
_cell_length_b                   8.1745(12)
_cell_length_c                   11.3622(16)
_cell_angle_alpha                90
_cell_angle_beta                 100.698(5)
_cell_angle_gamma                90
_cell_volume                     508.19(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1606
_cell_measurement_temperature    293.00
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      3.09
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0764 before and 0.0494 after correction.
The Ratio of minimum to maximum transmission is 0.8527.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             196
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4439
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.032
_diffrn_reflns_theta_min         3.089
_diffrn_ambient_temperature      293.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE TXS PHOTON II'
_diffrn_measurement_method       'ω and φ shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_monochromator  'Helios Multi-layer Optic'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   TXS
_diffrn_source_current           40.0
_diffrn_source_power             1.8
_diffrn_source_type              'Rotaing Anode'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                812
_reflns_number_total             1105
_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       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX5 V2023.9-2 (Bruker, 2023)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0725
_refine_ls_R_factor_gt           0.0514
_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)+(0.0594P)²+0.1065P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1455
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C1(H1)
;
_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
N1 N 0.9306(3) 0.6477(2) 0.87512(13) 0.0681(5) Uani 1 1 d . . . . .
C3 C 0.6186(3) 0.59773(19) 0.65416(14) 0.0511(5) Uani 1 1 d . . . . .
C2 C 0.8311(3) 0.6875(2) 0.66324(14) 0.0557(5) Uani 1 1 d . . . . .
H2 H 0.874837 0.732852 0.595177 0.067 Uiso 1 1 calc R U . . .
C6 C 0.4528(4) 0.5677(2) 0.53502(15) 0.0666(6) Uani 1 1 d . . . . .
H6A H 0.438508 0.667613 0.488209 0.080 Uiso 1 1 calc R U . . .
H6B H 0.291108 0.538835 0.548508 0.080 Uiso 1 1 calc R U . . .
C4 C 0.5685(3) 0.5333(2) 0.75935(16) 0.0612(5) Uani 1 1 d . . . . .
H4 H 0.427418 0.472069 0.758487 0.073 Uiso 1 1 calc R U . . .
C5 C 0.7280(4) 0.5602(2) 0.86536(15) 0.0693(6) Uani 1 1 d . . . . .
H5 H 0.691060 0.513950 0.934626 0.083 Uiso 1 1 calc R U . . .
C1 C 0.9781(4) 0.7094(2) 0.77386(15) 0.0620(5) Uani 1 1 d . . . . .
H1 H 1.119420 0.771422 0.777773 0.074 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0774(12) 0.0788(10) 0.0434(8) -0.0042(7) -0.0009(7) -0.0066(8)
C3 0.0528(10) 0.0506(8) 0.0464(8) -0.0084(6) -0.0002(7) 0.0104(7)
C2 0.0631(12) 0.0596(10) 0.0433(8) 0.0030(7) 0.0069(7) 0.0010(8)
C6 0.0622(12) 0.0723(11) 0.0569(10) -0.0156(8) -0.0107(8) 0.0167(9)
C4 0.0585(11) 0.0637(10) 0.0620(10) -0.0057(8) 0.0130(8) -0.0081(9)
C5 0.0865(15) 0.0777(12) 0.0455(9) 0.0021(8) 0.0170(9) -0.0058(10)
C1 0.0597(12) 0.0678(11) 0.0557(10) -0.0039(8) 0.0031(8) -0.0103(9)

_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
N1 C5 1.323(2) . ?
N1 C1 1.327(2) . ?
C3 C2 1.380(2) . ?
C3 C6 1.510(2) . ?
C3 C4 1.381(2) . ?
C2 H2 0.9300 . ?
C2 C1 1.378(2) . ?
C6 C6 1.513(3) 3_666 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9300 . ?
C1 H1 0.9300 . ?

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
C5 N1 C1 115.90(15) . . ?
C2 C3 C6 121.77(16) . . ?
C2 C3 C4 116.51(15) . . ?
C4 C3 C6 121.70(17) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 C3 119.56(16) . . ?
C1 C2 H2 120.2 . . ?
C3 C6 C6 112.09(18) . 3_666 ?
C3 C6 H6A 109.2 . . ?
C3 C6 H6B 109.2 . . ?
C6 C6 H6A 109.2 3_666 . ?
C6 C6 H6B 109.2 3_666 . ?
H6A C6 H6B 107.9 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.71(18) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 124.19(17) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
N1 C1 C2 124.11(18) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?

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
C3 C2 C1 N1 0.7(3) . . . . ?
C3 C4 C5 N1 1.0(3) . . . . ?
C2 C3 C6 C6 79.3(3) . . . 3_666 ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C6 C3 C2 C1 -179.05(15) . . . . ?
C6 C3 C4 C5 178.26(16) . . . . ?
C4 C3 C2 C1 -0.6(2) . . . . ?
C4 C3 C6 C6 -99.1(3) . . . 3_666 ?
C5 N1 C1 C2 0.1(3) . . . . ?
C1 N1 C5 C4 -1.0(3) . . . . ?

_shelx_res_file                  
;
TITL 240913lu_lgpz100798_0m_a.res in P2(1)/c
    240913lu_lgpz100798_0m.res
    created by SHELXL-2019/3 at 16:57:16 on 14-Sep-2024
REM Old TITL 240913LU_LGPZ100798_0m in P2(1)/c
REM SHELXT solution in P2(1)/c: R1 0.188, Rweak 0.013, Alpha 0.042
REM <I/s> 0.631 for 80 systematic absences, Orientation as input
REM Formula found by SHELXT: C6 N
CELL 0.71073 5.5682 8.1745 11.3622 90 100.698 90
ZERR 2 0.001 0.0012 0.0016 0 0.005 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N
UNIT 24 24 4

L.S. 10
PLAN  5
SIZE 0.08 0.11 0.13
TEMP 19.85
CONF
BOND
list 4
fmap 2
MORE -1
BOND $H
ACTA
SIZE 0.08 0.11 0.13
REM <olex2.extras>
REM <HklSrc "%.\\240913LU_LGPZ100798_0m.hkl">
REM </olex2.extras>

WGHT    0.059400    0.106500
FVAR       2.94057
N1    3    0.930624    0.647712    0.875120    11.00000    0.07737    0.07875 =
         0.04344   -0.00425   -0.00089   -0.00658
C3    1    0.618596    0.597728    0.654163    11.00000    0.05275    0.05065 =
         0.04637   -0.00840   -0.00022    0.01043
C2    1    0.831083    0.687478    0.663238    11.00000    0.06311    0.05960 =
         0.04330    0.00305    0.00687    0.00103
AFIX  43
H2    2    0.874837    0.732852    0.595177    11.00000   -1.20000
AFIX   0
C6    1    0.452799    0.567672    0.535017    11.00000    0.06215    0.07234 =
         0.05687   -0.01557   -0.01066    0.01668
AFIX  23
H6A   2    0.438508    0.667613    0.488209    11.00000   -1.20000
H6B   2    0.291108    0.538835    0.548508    11.00000   -1.20000
AFIX   0
C4    1    0.568458    0.533344    0.759346    11.00000    0.05849    0.06370 =
         0.06202   -0.00570    0.01301   -0.00812
AFIX  43
H4    2    0.427418    0.472069    0.758487    11.00000   -1.20000
AFIX   0
C5    1    0.727980    0.560228    0.865356    11.00000    0.08653    0.07773 =
         0.04553    0.00215    0.01703   -0.00584
AFIX  43
H5    2    0.691060    0.513950    0.934626    11.00000   -1.20000
AFIX   0
C1    1    0.978094    0.709447    0.773857    11.00000    0.05975    0.06775 =
         0.05570   -0.00389    0.00311   -0.01028
AFIX  43
H1    2    1.119420    0.771422    0.777773    11.00000   -1.20000
AFIX   0
HKLF 4




REM  240913lu_lgpz100798_0m_a.res in P2(1)/c
REM wR2 = 0.1455, GooF = S = 1.076, Restrained GooF = 1.076 for all data
REM R1 = 0.0514 for 812 Fo > 4sig(Fo) and 0.0725 for all 1105 data
REM 64 parameters refined using 0 restraints

END

WGHT      0.0594      0.1065

REM Highest difference peak  0.133,  deepest hole -0.157,  1-sigma level  0.028
Q1    1   0.5286  0.6029  0.6033  11.00000  0.05    0.13
Q2    1   0.2946  0.6278  0.5144  11.00000  0.05    0.13
Q3    1   0.6347  0.5320  0.6973  11.00000  0.05    0.12
Q4    1   0.6617  0.6795  0.6604  11.00000  0.05    0.11
Q5    1   0.2882  0.4491  0.5755  11.00000  0.05    0.11
;
_shelx_res_checksum              35942
_olex2_submission_special_instructions 'No special instructions were received'
_site                            XU
