# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1ver0-13840_kkg-164
_database_code_depnum_ccdc_archive 'CCDC 2050683'
loop_
_audit_author_name
_audit_author_address
'Sergey Baykov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;
_audit_creation_date             2020-12-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Methyl (4--methylpyridin--2--yl)carbamate'
_chemical_formula_moiety         'C8 H10 N2 O2'
_chemical_formula_sum            'C8 H10 N2 O2'
_chemical_formula_weight         166.18
_chemical_melting_point          414
_chemical_oxdiff_formula         'C9 H13 Cl2 N3 O1 Zn1'
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      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                   5.9064(3)
_cell_length_b                   18.7809(8)
_cell_length_c                   7.4306(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.589(5)
_cell_angle_gamma                90
_cell_volume                     817.04(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1489
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.7900
_cell_measurement_theta_min      4.6910
_shelx_estimated_absorpt_T_max   0.908
_shelx_estimated_absorpt_T_min   0.866
_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65304
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3366
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.066
_diffrn_reflns_theta_min         4.709
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  28.00   1.00    1.00    --  -40.13  38.00 -90.00   27
  2  ω    -67.00 -19.00   1.00    1.00    --  -40.13  38.00 -90.00   48
  3  ω   -109.00 -14.00   1.00    1.00    --  -40.13 -38.00  90.00   95
  4  ω     92.00 130.00   1.00    1.00    --   40.13 178.00  30.00   38
  5  ω    107.00 134.00   1.00    1.00    --  113.00 112.00 120.00   27
  6  ω    151.00 176.00   1.00    1.00    --  113.00 112.00 120.00   25
  7  ω     98.00 166.00   1.00    1.00    --  113.00  45.00  60.00   68
  8  ω     86.00 178.00   1.00    1.00    --  113.00  61.00   0.00   92
  9  ω    141.00 178.00   1.00    1.00    --  113.00 112.00-150.00   37
 10  ω    103.00 150.00   1.00    1.00    --  113.00 112.00-180.00   47
 11  ω     55.00 137.00   1.00    1.00    --  113.00 -61.00-150.00   82
 12  ω     71.00 109.00   1.00    1.00    --  113.00 -95.00-180.00   38
 13  ω     82.00 108.00   1.00    1.00    --   40.13-178.00 150.00   26
 14  ω     46.00 110.00   1.00    1.00    --  113.00-112.00 150.00   64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0308340000
_diffrn_orient_matrix_UB_12      -0.0791611000
_diffrn_orient_matrix_UB_13      0.0452230000
_diffrn_orient_matrix_UB_21      -0.1601477000
_diffrn_orient_matrix_UB_22      0.0209966000
_diffrn_orient_matrix_UB_23      0.1390290000
_diffrn_orient_matrix_UB_31      -0.2065037000
_diffrn_orient_matrix_UB_32      -0.0043955000
_diffrn_orient_matrix_UB_33      -0.1495906000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1396
_reflns_number_total             1661
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         1661
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.093
_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)+(0.0695P)²+0.0757P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1159
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C7(H7A,H7B,H7C)
;
_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
O2 O 1.03982(16) 0.50191(5) 0.75347(15) 0.0211(3) Uani 1 1 d . . . . .
O1 O 1.02619(17) 0.62118(5) 0.79098(15) 0.0223(3) Uani 1 1 d . . . . .
N2 N 0.7447(2) 0.55967(6) 0.60923(16) 0.0184(3) Uani 1 1 d . . . . .
H2 H 0.705350 0.516169 0.573851 0.022 Uiso 1 1 calc R U . . .
N1 N 0.39338(19) 0.59146(6) 0.46363(16) 0.0185(3) Uani 1 1 d . . . . .
C2 C 0.5971(2) 0.61470(7) 0.54359(18) 0.0163(3) Uani 1 1 d . . . . .
C1 C 0.9445(2) 0.56722(7) 0.72326(19) 0.0173(3) Uani 1 1 d . . . . .
C3 C 0.6556(2) 0.68665(7) 0.55801(19) 0.0178(3) Uani 1 1 d . . . . .
H3 H 0.804026 0.700708 0.611075 0.021 Uiso 1 1 calc R U . . .
C4 C 0.4939(2) 0.73746(8) 0.49373(18) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.2400(2) 0.64120(8) 0.4004(2) 0.0212(3) Uani 1 1 d . . . . .
H6 H 0.095014 0.625664 0.343275 0.025 Uiso 1 1 calc R U . . .
C5 C 0.2801(2) 0.71380(8) 0.4134(2) 0.0201(3) Uani 1 1 d . . . . .
H5 H 0.164415 0.746839 0.368596 0.024 Uiso 1 1 calc R U . . .
C8 C 1.2551(2) 0.50200(8) 0.8700(2) 0.0230(3) Uani 1 1 d . . . . .
H8A H 1.369703 0.526958 0.809512 0.035 Uiso 1 1 calc R U . . .
H8B H 1.304642 0.452830 0.895705 0.035 Uiso 1 1 calc R U . . .
H8C H 1.237283 0.526287 0.984014 0.035 Uiso 1 1 calc R U . . .
C7 C 0.5505(2) 0.81519(7) 0.5117(2) 0.0212(3) Uani 1 1 d . . . . .
H7A H 0.563211 0.829078 0.639810 0.032 Uiso 1 1 calc R U . . .
H7B H 0.429435 0.843040 0.441296 0.032 Uiso 1 1 calc R U . . .
H7C H 0.696006 0.824236 0.465901 0.032 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
O2 C1 1.3560(15) . ?
O2 C8 1.4405(16) . ?
O1 C1 1.2038(17) . ?
N2 H2 0.8800 . ?
N2 C2 1.3977(18) . ?
N2 C1 1.3660(18) . ?
N1 C2 1.3427(17) . ?
N1 C6 1.3424(18) . ?
C2 C3 1.3953(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
C4 C5 1.396(2) . ?
C4 C7 1.500(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.385(2) . ?
C5 H5 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
C1 O2 C8 114.38(11) . . ?
C2 N2 H2 117.0 . . ?
C1 N2 H2 117.0 . . ?
C1 N2 C2 125.97(12) . . ?
C6 N1 C2 116.91(12) . . ?
N1 C2 N2 113.28(12) . . ?
N1 C2 C3 123.17(13) . . ?
C3 C2 N2 123.55(12) . . ?
O2 C1 N2 108.33(12) . . ?
O1 C1 O2 123.88(12) . . ?
O1 C1 N2 127.77(13) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.13(13) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 118.05(13) . . ?
C3 C4 C7 120.18(13) . . ?
C5 C4 C7 121.77(13) . . ?
N1 C6 H6 118.0 . . ?
N1 C6 C5 124.01(13) . . ?
C5 C6 H6 118.0 . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.67(13) . . ?
C6 C5 H5 120.7 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
N2 C2 C3 C4 -177.87(13) . . . . ?
N1 C2 C3 C4 2.7(2) . . . . ?
N1 C6 C5 C4 1.3(2) . . . . ?
C2 N2 C1 O2 -179.13(12) . . . . ?
C2 N2 C1 O1 2.1(2) . . . . ?
C2 N1 C6 C5 -0.1(2) . . . . ?
C2 C3 C4 C5 -1.37(19) . . . . ?
C2 C3 C4 C7 178.50(12) . . . . ?
C1 N2 C2 N1 -167.67(13) . . . . ?
C1 N2 C2 C3 12.8(2) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C6 N1 C2 N2 178.60(12) . . . . ?
C6 N1 C2 C3 -1.9(2) . . . . ?
C8 O2 C1 O1 -2.2(2) . . . . ?
C8 O2 C1 N2 179.01(12) . . . . ?
C7 C4 C5 C6 179.65(13) . . . . ?

_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 1.572
_oxdiff_exptl_absorpt_empirical_full_min 0.485
_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_15941_bsc-297
_database_code_depnum_ccdc_archive 'CCDC 2050682'
loop_
_audit_author_name
_audit_author_address
'Sergey Baykov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;
_audit_creation_date             2020-12-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'2,2,2--Trifluoroethyl (4--methylpyridin--2--yl)carbamate'
_chemical_formula_moiety         'C9 H9 F3 N2 O2'
_chemical_formula_sum            'C9 H9 F3 N2 O2'
_chemical_formula_weight         234.18
_chemical_melting_point          459
_chemical_oxdiff_formula         'C9 H9 F3 N2 O2'
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'
F F 0.0727 0.0534 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.8119(2)
_cell_length_b                   10.5336(4)
_cell_length_c                   10.7314(4)
_cell_angle_alpha                114.870(4)
_cell_angle_beta                 94.157(4)
_cell_angle_gamma                90.003(3)
_cell_volume                     491.92(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4497
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.0780
_cell_measurement_theta_min      4.5430
_shelx_estimated_absorpt_T_max   0.868
_shelx_estimated_absorpt_T_min   0.806
_exptl_absorpt_coefficient_mu    1.327
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6782
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.323
_diffrn_reflns_theta_min         4.556
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -22.00   4.00   0.50    0.06    --   47.20 -57.00  30.00   52
  2  ω      8.00  62.00   0.50    0.06    --   47.20 -57.00  30.00  108
  3  ω     32.00  72.00   0.50    0.06    --   47.20-108.00 -65.00   80
  4  ω     75.00 104.00   0.50    0.30    --  107.75-108.00 -65.00   58
  5  ω     60.00 104.00   0.50    0.30    --  107.75 -77.00   0.00   88
  6  ω     83.00 112.00   0.50    0.30    --  107.75-125.00   0.00   58
  7  ω     58.00 106.00   0.50    0.30    --  107.75 -77.00 -60.00   96
  8  ω     58.00 109.00   0.50    0.30    --  107.75-125.00-120.00  102
  9  ω     39.00  65.00   0.50    0.30    --  107.75-108.00 -65.00   52
 10  ω     36.00  80.00   0.50    0.30    --  107.75-125.00 -60.00   88
 11  ω     43.00  78.00   0.50    0.30    --  107.75 -94.00 -60.00   70
 12  ω     42.00  99.00   0.50    0.30    --  107.75 -94.00-120.00  114
 13  ω     45.00  71.00   0.50    0.30    --  107.75 -61.00-180.00   52
 14  ω      1.00  27.00   0.50    0.06    --   47.20-108.00 -65.00   52
 15  ω    -26.00  42.00   0.50    0.06    --   47.20 -37.00 -60.00  136
 16  ω    -10.00  15.00   0.50    0.06    --   47.20 -19.00-120.00   50
 17  ω     95.00 175.00   0.50    0.30    --  107.75  15.00 -30.00  160
 18  ω    108.00 133.00   0.50    0.30    --  107.75 108.00  31.00   50
 19  ω     98.00 149.00   0.50    0.30    --  107.75  45.00  60.00  102
 20  ω    102.00 178.00   0.50    0.30    --  107.75  15.00  30.00  152
 21  ω     74.00 108.00   0.50    0.06    --   47.20 125.00   0.00   68
 22  ω     35.00  71.00   0.50    0.30    --  107.75 -61.00 150.00   72
 23  ω     38.00  64.00   0.50    0.30    --  107.75 -94.00 120.00   52
 24  ω     73.00 112.00   0.50    0.30    --  107.75-125.00 150.00   78
 25  ω     36.00  62.00   0.50    0.30    --  107.75-125.00 150.00   52
 26  ω     36.00  87.00   0.50    0.30    --  107.75 -77.00 120.00  102
 27  ω    -41.00 -15.00   0.50    0.06    --  -47.20 108.00  31.00   52
 28  ω    -81.00 -55.00   0.50    0.06    --  -47.20 108.00  31.00   52
 29  ω   -115.00 -86.00   0.50    0.06    --  -47.20-125.00 -30.00   58
 30  ω   -120.00 -95.00   0.50    0.06    --  -47.20-125.00   0.00   50
 31  ω   -116.00 -77.00   0.50    0.06    --  -47.20-125.00  30.00   78
 32  ω   -149.00-110.00   0.50    0.30    -- -106.00-108.00 -65.00   78
 33  ω   -158.00-111.00   0.50    0.30    -- -106.00 -61.00 -30.00   94
 34  ω   -175.00 -95.00   0.50    0.30    -- -106.00 -15.00 120.00  160
 35  ω    -70.00 -36.00   0.50    0.30    -- -106.00  61.00 120.00   68
 36  ω    -70.00 -33.00   0.50    0.30    -- -106.00  61.00  90.00   74
 37  ω    -61.00 -35.00   0.50    0.30    -- -106.00  61.00  30.00   52
 38  ω    -62.00 -37.00   0.50    0.30    -- -106.00  61.00   0.00   50
 39  ω    -90.00 -64.00   0.50    0.30    -- -106.00 108.00  31.00   52
 40  ω    -91.00 -66.00   0.50    0.30    -- -106.00 139.00 -35.49   50
 41  ω   -122.00 -97.00   0.50    0.30    -- -106.00 139.00 -35.49   50
 42  ω   -127.00 -68.00   0.50    0.30    -- -106.00 146.00  69.05  118
 43  ω   -112.00 -57.00   0.50    0.30    -- -106.00 125.00-180.00  110
 44  ω   -159.00-100.00   0.50    0.30    -- -106.00 -15.00-180.00  118
 45  ω     74.00  99.00   0.50    0.06    --   47.20 125.00 -30.00   50
 46  ω      2.00  28.00   0.50    0.06    --   22.00  73.00  48.50   52
 47  ω     -6.00  20.00   0.50    0.06    --   26.00  96.00-161.96   52
 48  ω     17.00  42.00   0.50    0.06    --   46.00  90.00 107.69   50
 49  ω     26.00  52.00   0.50    0.06    --   47.20  77.00 -90.00   52
 50  ω     28.00  54.00   0.50    0.06    --   47.20  77.00  60.00   52
 51  ω     36.00  62.00   0.50    0.06    --   47.20  57.00   0.00   52
 52  ω     35.00  68.00   0.50    0.06    --   47.20  37.00 -30.00   66
 53  ω     41.00  68.00   0.50    0.06    --   47.20  37.00-180.00   54
 54  ω     57.00  84.00   0.50    0.06    --   47.20  19.00   0.00   54
 55  ω     29.00  60.00   0.50    0.06    --   50.00  80.00 143.22   62
 56  ω     27.00  52.00   0.50    0.06    --   50.00  77.00  37.26   50
 57  ω     33.00  59.00   0.50    0.06    --   54.00  73.00-130.58   52
 58  ω     36.00  62.00   0.50    0.06    --   58.00  76.00 162.06   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1339909000
_diffrn_orient_matrix_UB_12      -0.0824192000
_diffrn_orient_matrix_UB_13      -0.1475916000
_diffrn_orient_matrix_UB_21      -0.1346196000
_diffrn_orient_matrix_UB_22      -0.1050472000
_diffrn_orient_matrix_UB_23      0.0450653000
_diffrn_orient_matrix_UB_31      -0.2590045000
_diffrn_orient_matrix_UB_32      0.0904854000
_diffrn_orient_matrix_UB_33      0.0371960000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1872
_reflns_number_total             2033
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2033
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.093
_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)+(0.0591P)²+0.1184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_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, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_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
F1 F 0.25656(18) 0.71609(8) 0.84761(9) 0.0304(2) Uani 1 1 d . . . . .
F3 F 0.11817(17) 0.54295(9) 0.88766(8) 0.0285(2) Uani 1 1 d . . . . .
F2 F 0.52001(17) 0.54032(9) 0.81216(9) 0.0319(2) Uani 1 1 d . . . . .
O2 O 0.10320(19) 0.36240(9) 0.61134(9) 0.0214(2) Uani 1 1 d . . . . .
O1 O 0.4121(2) 0.32999(10) 0.45167(11) 0.0278(2) Uani 1 1 d . . . . .
N2 N 0.1930(2) 0.14557(11) 0.47127(11) 0.0185(2) Uani 1 1 d . . . . .
H2 H 0.067886 0.128047 0.518352 0.022 Uiso 1 1 calc R U . . .
N1 N 0.2149(2) -0.09206(11) 0.36369(11) 0.0184(2) Uani 1 1 d . . . . .
C2 C 0.3089(2) 0.02974(12) 0.36917(12) 0.0173(3) Uani 1 1 d . . . . .
C3 C 0.5001(3) 0.03959(13) 0.28142(13) 0.0193(3) Uani 1 1 d . . . . .
H3 H 0.561319 0.128426 0.288846 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5992(2) -0.08268(13) 0.18314(12) 0.0189(3) Uani 1 1 d . . . . .
C1 C 0.2552(3) 0.28156(12) 0.50425(12) 0.0186(3) Uani 1 1 d . . . . .
C5 C 0.5049(3) -0.21006(13) 0.17794(13) 0.0204(3) Uani 1 1 d . . . . .
H5 H 0.570455 -0.295850 0.113219 0.024 Uiso 1 1 calc R U . . .
C6 C 0.3144(3) -0.20947(13) 0.26843(13) 0.0202(3) Uani 1 1 d . . . . .
H6 H 0.249871 -0.296971 0.263143 0.024 Uiso 1 1 calc R U . . .
C9 C 0.2557(3) 0.57614(13) 0.80121(14) 0.0219(3) Uani 1 1 d . . . . .
C7 C 0.7993(3) -0.07710(14) 0.08422(14) 0.0229(3) Uani 1 1 d . . . . .
H7A H 0.700588 -0.104445 -0.006888 0.034 Uiso 1 1 calc R U . . .
H7B H 0.950081 -0.141588 0.077791 0.034 Uiso 1 1 calc R U . . .
H7C H 0.877773 0.018383 0.117251 0.034 Uiso 1 1 calc R U . . .
C8 C 0.1273(3) 0.50997(12) 0.65553(13) 0.0207(3) Uani 1 1 d . . . . .
H8A H -0.059290 0.547904 0.650391 0.025 Uiso 1 1 calc R U . . .
H8B H 0.245227 0.531665 0.594666 0.025 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
F1 C9 1.3430(14) . ?
F3 C9 1.3353(15) . ?
F2 C9 1.3375(16) . ?
O2 C1 1.3709(14) . ?
O2 C8 1.4236(14) . ?
O1 C1 1.2054(16) . ?
N2 H2 0.8800 . ?
N2 C2 1.4017(15) . ?
N2 C1 1.3509(16) . ?
N1 C2 1.3366(16) . ?
N1 C6 1.3459(16) . ?
C2 C3 1.3971(17) . ?
C3 H3 0.9500 . ?
C3 C4 1.3889(17) . ?
C4 C5 1.3939(17) . ?
C4 C7 1.5026(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3810(17) . ?
C6 H6 0.9500 . ?
C9 C8 1.5017(19) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

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 O2 C8 116.74(9) . . ?
C2 N2 H2 116.9 . . ?
C1 N2 H2 116.9 . . ?
C1 N2 C2 126.18(10) . . ?
C2 N1 C6 117.00(10) . . ?
N1 C2 N2 112.69(10) . . ?
N1 C2 C3 123.34(11) . . ?
C3 C2 N2 123.97(11) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 C2 118.88(11) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 118.11(11) . . ?
C3 C4 C7 120.67(11) . . ?
C5 C4 C7 121.22(11) . . ?
O1 C1 O2 123.16(11) . . ?
O1 C1 N2 128.50(11) . . ?
N2 C1 O2 108.34(10) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 C4 118.89(11) . . ?
C6 C5 H5 120.6 . . ?
N1 C6 C5 123.76(12) . . ?
N1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
F1 C9 C8 109.41(11) . . ?
F3 C9 F1 107.33(10) . . ?
F3 C9 F2 106.80(11) . . ?
F3 C9 C8 113.17(11) . . ?
F2 C9 F1 107.25(10) . . ?
F2 C9 C8 112.57(11) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C9 109.14(10) . . ?
O2 C8 H8A 109.9 . . ?
O2 C8 H8B 109.9 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?

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
F1 C9 C8 O2 -174.62(9) . . . . ?
F3 C9 C8 O2 -54.99(13) . . . . ?
F2 C9 C8 O2 66.23(13) . . . . ?
N2 C2 C3 C4 -179.45(11) . . . . ?
N1 C2 C3 C4 -0.06(19) . . . . ?
C2 N2 C1 O2 -178.47(11) . . . . ?
C2 N2 C1 O1 2.4(2) . . . . ?
C2 N1 C6 C5 -0.04(19) . . . . ?
C2 C3 C4 C5 -0.74(18) . . . . ?
C2 C3 C4 C7 178.40(11) . . . . ?
C3 C4 C5 C6 1.12(18) . . . . ?
C4 C5 C6 N1 -0.8(2) . . . . ?
C1 O2 C8 C9 -116.28(12) . . . . ?
C1 N2 C2 N1 177.51(11) . . . . ?
C1 N2 C2 C3 -3.0(2) . . . . ?
C6 N1 C2 N2 179.91(10) . . . . ?
C6 N1 C2 C3 0.46(18) . . . . ?
C7 C4 C5 C6 -178.01(11) . . . . ?
C8 O2 C1 O1 3.02(18) . . . . ?
C8 O2 C1 N2 -176.21(10) . . . . ?

_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 1.414
_oxdiff_exptl_absorpt_empirical_full_min 0.710
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_16831_ucm-26
_database_code_depnum_ccdc_archive 'CCDC 2050685'
loop_
_audit_author_name
_audit_author_address
'Sergey Baykov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;
_audit_creation_date             2020-12-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        '2--Methoxyethyl quinolin--2--ylcarbamate'
_chemical_formula_moiety         'C13 H14 N2 O3'
_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_weight         246.26
_chemical_melting_point          333
_chemical_oxdiff_formula         'C13 H14 N2  O3 '
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.9095(2)
_cell_length_b                   7.96230(10)
_cell_length_c                   25.3411(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.9570(10)
_cell_angle_gamma                90
_cell_volume                     2390.04(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    18983
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.1150
_cell_measurement_theta_min      4.2650
_shelx_estimated_absorpt_T_max   0.923
_shelx_estimated_absorpt_T_min   0.860
_exptl_absorpt_coefficient_mu    0.815
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82041
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.19
_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  0.0473
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            48959
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.841
_diffrn_reflns_theta_min         3.507
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  -1.00   0.50    3.26    --   47.20 -15.00  59.00   50
  2  ω     35.00 102.00   0.50   13.03    --  107.75 -77.00 150.00  134
  3  ω     62.00 126.00   0.50   13.03    --  107.75-144.00  43.78  128
  4  ω     77.00 118.00   0.50   13.03    --  107.75-133.00   9.18   82
  5  ω     81.00 106.00   0.50   13.03    --  107.75 -94.00-120.00   50
  6  ω     50.00 108.00   0.50   13.03    --  107.75-125.00 -90.00  116
  7  ω     39.00  95.00   0.50    3.26    --   47.20-125.00-120.00  112
  8  ω     39.00  77.00   0.50   13.03    --  107.75 -94.00-120.00   76
  9  ω     46.00 106.00   0.50   13.03    --  107.75 -77.00-120.00  120
 10  ω     41.00 121.00   0.50    3.26    --   47.20  15.00-129.00  160
 11  ω     94.00 175.00   0.50   13.03    --  107.75  15.00-129.00  162
 12  ω    120.00 175.00   0.50   13.03    --  107.75  45.00-120.00  110
 13  ω     44.00  70.00   0.50   13.03    --  107.75 -61.00  60.00   52
 14  ω     44.00  70.00   0.50   13.03    --  107.75 -61.00  90.00   52
 15  ω    100.00 178.00   0.50   13.03    --  107.75  15.00 150.00  156
 16  ω     46.00  74.00   0.50   13.03    --  107.75-133.00   9.18   56
 17  ω     50.00  75.00   0.50   13.03    --  107.75-125.00-120.00   50
 18  ω     35.00  71.00   0.50   13.03    --  107.75 -61.00-180.00   72
 19  ω     39.00  69.00   0.50   13.03    --  107.75 -61.00-120.00   60
 20  ω    -23.00  20.00   0.50    3.26    --  -47.20  15.00-129.00   86
 21  ω    -24.00  19.00   0.50    3.26    --  -47.20  37.00   0.00   86
 22  ω    -59.00 -34.00   0.50   13.03    -- -106.00  61.00  90.00   50
 23  ω    -81.00 -51.00   0.50   13.03    -- -106.00  77.00  30.00   60
 24  ω    -70.00 -35.00   0.50   13.03    -- -106.00  61.00 -30.00   70
 25  ω    -75.00 -34.00   0.50   13.03    -- -106.00 125.00-120.00   82
 26  ω   -112.00 -87.00   0.50   13.03    -- -106.00 125.00 -90.00   50
 27  ω   -120.00 -93.00   0.50   13.03    -- -106.00 137.00 -97.95   54
 28  ω   -114.00 -46.00   0.50    3.26    --  -47.20 -15.00  59.00  136
 29  ω   -124.00 -98.00   0.50   13.03    -- -106.00 -77.00 -30.00   52
 30  ω   -151.00-126.00   0.50   13.03    -- -106.00 -15.00  59.00   50
 31  ω     -7.00  19.00   0.50    3.26    --   47.20 -15.00  59.00   52
 32  ω    -55.00 -29.00   0.50    3.26    --  -47.20 -77.00 -30.00   52
 33  ω     42.00  68.00   0.50    3.26    --   47.20  57.00  60.00   52
 34  ω     41.00  68.00   0.50    3.26    --   47.20  19.00 -30.00   54
 35  ω     25.00  89.00   0.50    3.26    --   47.20  77.00 -60.00  128
 36  ω     33.00  58.00   0.50    3.26    --   47.20  57.00 -60.00   50
 37  ω     37.00  73.00   0.50    3.26    --   47.20  37.00 -30.00   72
 38  ω     29.00  55.00   0.50    3.26    --   47.20  77.00 -90.00   52
 39  ω     32.00  75.00   0.50    3.26    --   47.20  57.00  30.00   86
 40  ω   -110.00 -85.00   0.50   13.03    -- -106.00 -74.00  18.15   50
 41  ω   -116.00 -89.00   0.50   13.03    -- -106.00 -63.00  -2.51   54
 42  ω   -120.00 -87.00   0.50   13.03    -- -106.00 -68.00 -76.30   66
 43  ω   -116.00 -90.00   0.50   13.03    -- -106.00 -70.00 -49.59   52
 44  ω   -127.00 -86.00   0.50   13.03    -- -106.00 -70.00 -55.85   82
 45  ω   -159.00 -88.00   0.50   13.03    -- -106.00 -64.00 -10.21  142
 46  ω   -114.00 -89.00   0.50   13.03    -- -106.00 -61.00   0.00   50
 47  ω   -107.00 -81.00   0.50   13.03    -- -106.00 -84.00 -75.69   52
 48  ω   -108.00 -83.00   0.50   13.03    -- -106.00 -77.00 -60.00   50
 49  ω   -171.00-146.00   0.50   13.03    -- -106.00 -81.00  54.00   50
 50  ω   -108.00 -83.00   0.50   13.03    -- -106.00 -77.00 -80.85   50
 51  ω   -111.00 -86.00   0.50   13.03    -- -106.00 -69.00 -20.90   50
 52  ω   -115.00 -81.00   0.50   13.03    -- -106.00 -81.00  54.00   68
 53  ω   -109.00 -81.00   0.50   13.03    -- -106.00 -82.00 -88.49   56
 54  ω   -155.00-130.00   0.50   13.03    -- -106.00 -82.00-106.78   50
 55  ω   -168.00-142.00   0.50   13.03    -- -106.00 -77.00  30.00   52
 56  ω   -116.00 -83.00   0.50   13.03    -- -106.00 -77.00  30.00   66
 57  ω   -163.00-137.00   0.50   13.03    -- -106.00 -70.00 -55.85   52
 58  ω   -114.00 -89.00   0.50   13.03    -- -106.00 -61.00 -60.00   50
 59  ω   -146.00 -83.00   0.50   13.03    -- -106.00 -78.00  37.65  126
 60  ω   -151.00-125.00   0.50   13.03    -- -106.00 -45.00 -30.00   52
 61  ω   -109.00 -83.00   0.50   13.03    -- -106.00 -77.00 -90.00   52
 62  ω   -119.00 -89.00   0.50   13.03    -- -106.00 -61.00 -90.00   60
 63  ω    -68.00 -42.00   0.50   13.03    -- -106.00  61.00 150.00   52
 64  ω   -109.00 -84.00   0.50   13.03    -- -106.00 -77.00   0.00   50
 65  ω   -114.00 -89.00   0.50   13.03    -- -106.00 -61.00 -36.23   50
 66  ω   -176.00 -91.00   0.50   13.03    -- -106.00 -56.00 -30.48  170
 67  ω   -137.00 -93.00   0.50   13.03    -- -106.00 -49.00 -82.91   88
 68  ω   -168.00-142.00   0.50   13.03    -- -106.00 -77.00   0.00   52
 69  ω   -114.00 -89.00   0.50   13.03    -- -106.00 -61.00 -57.03   50
 70  ω   -114.00 -89.00   0.50   13.03    -- -106.00 -62.00  -8.07   50
 71  ω   -175.00-147.00   0.50   13.03    -- -106.00 -68.00 -80.81   56
 72  ω   -113.00 -88.00   0.50   13.03    -- -106.00 -68.00 -80.81   50
 73  ω   -117.00 -87.00   0.50   13.03    -- -106.00 -68.00 -87.32   60
 74  ω   -136.00 -85.00   0.50   13.03    -- -106.00 -72.00  17.48  102
 75  ω   -161.00-135.00   0.50   13.03    -- -106.00 -77.00  60.00   52
 76  ω   -110.00 -84.00   0.50   13.03    -- -106.00 -77.00  60.00   52
 77  ω   -176.00-150.00   0.50   13.03    -- -106.00 -61.00 -36.23   52
 78  ω   -108.00 -83.00   0.50   13.03    -- -106.00 -77.00 -30.00   50
 79  ω   -106.00 -81.00   0.50   13.03    -- -106.00 -82.00-106.78   50
 80  ω   -122.00 -93.00   0.50   13.03    -- -106.00 -45.00  30.00   58
 81  ω   -164.00-138.00   0.50   13.03    -- -106.00 -82.00 -88.49   52
 82  ω   -118.00 -93.00   0.50   13.03    -- -106.00 -50.00 -52.98   50
 83  ω   -138.00 -93.00   0.50   13.03    -- -106.00 -51.00 -62.55   90
 84  ω   -115.00 -90.00   0.50   13.03    -- -106.00 -60.00 -45.51   50
 85  ω   -105.00 -80.00   0.50   13.03    -- -106.00 -90.00 -86.81   50
 86  ω   -115.00 -86.00   0.50   13.03    -- -106.00 -71.00  34.43   58
 87  ω    114.00 139.00   0.50   13.03    --  107.75  77.00 -60.00   50
 88  ω     85.00 111.00   0.50   13.03    --  107.75  77.00 -60.00   52
 89  ω     90.00 115.00   0.50   13.03    --  107.75  66.00  24.12   50
 90  ω     86.00 112.00   0.50   13.03    --  107.75  77.00   0.00   52
 91  ω     87.00 113.00   0.50   13.03    --  107.75  77.00 -90.00   52
 92  ω     95.00 121.00   0.50   13.03    --  107.75  77.00 -30.00   52
 93  ω     83.00 111.00   0.50   13.03    --  107.75  81.00-113.50   56
 94  ω     35.00  60.00   0.50   13.03    --  107.75 -61.00 -60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1268503000
_diffrn_orient_matrix_UB_12      -0.0336250000
_diffrn_orient_matrix_UB_13      -0.0143887000
_diffrn_orient_matrix_UB_21      0.0153859000
_diffrn_orient_matrix_UB_22      0.0204078000
_diffrn_orient_matrix_UB_23      -0.0592871000
_diffrn_orient_matrix_UB_31      0.0241695000
_diffrn_orient_matrix_UB_32      -0.1894253000
_diffrn_orient_matrix_UB_33      -0.0038535000
_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              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4637
_reflns_number_total             4990
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     327
_refine_ls_number_reflns         4990
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.068
_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)+(0.0473P)²+0.9359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.0992
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11A(H11A,H11B), C12A(H12A,H12B), C12(H12C,H12D), C11(H11C,H11D)
2.b Aromatic/amide H refined with riding coordinates:
 N2A(H2A), N2(H2), C4(H4), C9(H9), C3(H3), C8(H8), C6(H6), C9A(H9A), C3A(H3A),
 C7(H7), C6A(H6A), C4A(H4A), C8A(H8A), C7A(H7A)
2.c Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C13(H13D,H13E,H13F)
;
_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
O2A O 0.37054(7) 0.93912(10) 0.53600(3) 0.02152(19) Uani 1 1 d . . . . .
O2 O 0.25320(7) 0.48672(12) 0.71878(3) 0.02432(19) Uani 1 1 d . . . . .
O1A O 0.46173(8) 1.08722(11) 0.60359(4) 0.0288(2) Uani 1 1 d . . . . .
O3A O 0.17378(7) 1.04842(11) 0.45356(4) 0.0267(2) Uani 1 1 d . . . . .
O1 O 0.09008(7) 0.47974(13) 0.66423(4) 0.0290(2) Uani 1 1 d . . . . .
O3 O 0.30065(8) 0.38181(12) 0.83085(4) 0.0317(2) Uani 1 1 d . . . . .
N1 N 0.31067(8) 0.52726(12) 0.54938(4) 0.0192(2) Uani 1 1 d . . . . .
N2A N 0.44784(8) 0.79832(13) 0.60533(4) 0.0205(2) Uani 1 1 d . . . . .
H2A H 0.422304 0.713193 0.585433 0.025 Uiso 1 1 calc R U . . .
N1A N 0.48751(8) 0.60228(13) 0.66964(4) 0.0196(2) Uani 1 1 d . . . . .
N2 N 0.26496(8) 0.47329(13) 0.63279(4) 0.0209(2) Uani 1 1 d . . . . .
H2 H 0.337618 0.473595 0.643564 0.025 Uiso 1 1 calc R U . . .
C2A C 0.50257(9) 0.75918(15) 0.65535(4) 0.0194(2) Uani 1 1 d . . . . .
C1A C 0.43000(10) 0.95458(15) 0.58426(5) 0.0205(2) Uani 1 1 d . . . . .
C10 C 0.28975(10) 0.51817(14) 0.49519(4) 0.0193(2) Uani 1 1 d . . . . .
C2 C 0.23450(10) 0.46587(14) 0.57838(5) 0.0193(2) Uani 1 1 d . . . . .
C5 C 0.18844(10) 0.44900(14) 0.46972(5) 0.0209(2) Uani 1 1 d . . . . .
C1 C 0.19203(10) 0.48017(15) 0.67115(5) 0.0221(2) Uani 1 1 d . . . . .
C10A C 0.53896(10) 0.54836(16) 0.71751(5) 0.0207(2) Uani 1 1 d . . . . .
C4 C 0.11014(10) 0.38346(15) 0.50269(5) 0.0225(2) Uani 1 1 d . . . . .
H4 H 0.042042 0.333869 0.487144 0.027 Uiso 1 1 calc R U . . .
C9 C 0.37157(10) 0.58150(15) 0.46386(5) 0.0216(2) Uani 1 1 d . . . . .
H9 H 0.439355 0.629037 0.480522 0.026 Uiso 1 1 calc R U . . .
C11A C 0.35533(10) 1.09428(15) 0.50640(5) 0.0229(2) Uani 1 1 d . . . . .
H11A H 0.429778 1.144427 0.501837 0.027 Uiso 1 1 calc R U . . .
H11B H 0.312193 1.175283 0.526014 0.027 Uiso 1 1 calc R U . . .
C3 C 0.13146(10) 0.39076(15) 0.55656(5) 0.0224(2) Uani 1 1 d . . . . .
H3 H 0.079137 0.347039 0.578878 0.027 Uiso 1 1 calc R U . . .
C12A C 0.29229(10) 1.05837(16) 0.45283(5) 0.0239(3) Uani 1 1 d . . . . .
H12A H 0.309578 1.147956 0.427817 0.029 Uiso 1 1 calc R U . . .
H12B H 0.319831 0.950872 0.439357 0.029 Uiso 1 1 calc R U . . .
C5A C 0.60442(10) 0.65725(17) 0.75257(5) 0.0236(3) Uani 1 1 d . . . . .
C8 C 0.35379(11) 0.57485(15) 0.40944(5) 0.0243(3) Uani 1 1 d . . . . .
H8 H 0.409433 0.617418 0.388703 0.029 Uiso 1 1 calc R U . . .
C6 C 0.17162(11) 0.44482(15) 0.41356(5) 0.0239(3) Uani 1 1 d . . . . .
H6 H 0.103563 0.400146 0.396226 0.029 Uiso 1 1 calc R U . . .
C9A C 0.52480(10) 0.37920(17) 0.73187(5) 0.0248(3) Uani 1 1 d . . . . .
H9A H 0.483585 0.304590 0.707841 0.030 Uiso 1 1 calc R U . . .
C3A C 0.57002(11) 0.87605(16) 0.68679(5) 0.0246(3) Uani 1 1 d . . . . .
H3A H 0.580689 0.987257 0.674673 0.030 Uiso 1 1 calc R U . . .
C7 C 0.25309(12) 0.50494(16) 0.38418(5) 0.0260(3) Uani 1 1 d . . . . .
H7 H 0.241871 0.499633 0.346551 0.031 Uiso 1 1 calc R U . . .
C6A C 0.65080(11) 0.59436(18) 0.80259(5) 0.0292(3) Uani 1 1 d . . . . .
H6A H 0.694209 0.666208 0.826713 0.035 Uiso 1 1 calc R U . . .
C4A C 0.61903(11) 0.82339(17) 0.73498(5) 0.0274(3) Uani 1 1 d . . . . .
H4A H 0.663678 0.899622 0.757062 0.033 Uiso 1 1 calc R U . . .
C8A C 0.57055(11) 0.32219(18) 0.78057(5) 0.0281(3) Uani 1 1 d . . . . .
H8A H 0.559833 0.208561 0.790325 0.034 Uiso 1 1 calc R U . . .
C7A C 0.63336(12) 0.43135(19) 0.81620(5) 0.0302(3) Uani 1 1 d . . . . .
H7A H 0.663796 0.391002 0.849968 0.036 Uiso 1 1 calc R U . . .
C13A C 0.13295(11) 0.88538(17) 0.46290(5) 0.0278(3) Uani 1 1 d . . . . .
H13A H 0.152056 0.809562 0.434712 0.042 Uiso 1 1 calc R U . . .
H13B H 0.050782 0.889269 0.463239 0.042 Uiso 1 1 calc R U . . .
H13C H 0.167736 0.844388 0.497240 0.042 Uiso 1 1 calc R U . . .
C12 C 0.26949(12) 0.54378(18) 0.81174(5) 0.0303(3) Uani 1 1 d . . . . .
H12C H 0.337728 0.606623 0.804162 0.036 Uiso 1 1 calc R U . . .
H12D H 0.233005 0.606127 0.839143 0.036 Uiso 1 1 calc R U . . .
C13 C 0.37101(13) 0.3911(2) 0.87929(5) 0.0338(3) Uani 1 1 d . . . . .
H13D H 0.439455 0.454474 0.873947 0.051 Uiso 1 1 calc R U . . .
H13E H 0.391757 0.277408 0.891515 0.051 Uiso 1 1 calc R U . . .
H13F H 0.330569 0.447798 0.905963 0.051 Uiso 1 1 calc R U . . .
C11 C 0.18968(12) 0.5305(2) 0.76228(5) 0.0350(3) Uani 1 1 d . . . . .
H11C H 0.132104 0.443415 0.766716 0.042 Uiso 1 1 calc R U . . .
H11D H 0.150555 0.639049 0.754946 0.042 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
O2A C1A 1.3538(14) . ?
O2A C11A 1.4470(14) . ?
O2 C1 1.3445(15) . ?
O2 C11 1.4430(15) . ?
O1A C1A 1.2082(15) . ?
O3A C12A 1.4157(15) . ?
O3A C13A 1.4148(16) . ?
O1 C1 1.2087(15) . ?
O3 C12 1.4135(17) . ?
O3 C13 1.4146(16) . ?
N1 C10 1.3719(15) . ?
N1 C2 1.3193(15) . ?
N2A H2A 0.8800 . ?
N2A C2A 1.3989(15) . ?
N2A C1A 1.3619(16) . ?
N1A C2A 1.3182(16) . ?
N1A C10A 1.3700(15) . ?
N2 H2 0.8800 . ?
N2 C2 1.3901(15) . ?
N2 C1 1.3703(15) . ?
C2A C3A 1.4189(17) . ?
C10 C5 1.4191(17) . ?
C10 C9 1.4122(17) . ?
C2 C3 1.4242(17) . ?
C5 C4 1.4147(17) . ?
C5 C6 1.4169(17) . ?
C10A C5A 1.4159(17) . ?
C10A C9A 1.4099(18) . ?
C4 H4 0.9500 . ?
C4 C3 1.3637(17) . ?
C9 H9 0.9500 . ?
C9 C8 1.3744(17) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C11A C12A 1.5087(17) . ?
C3 H3 0.9500 . ?
C12A H12A 0.9900 . ?
C12A H12B 0.9900 . ?
C5A C6A 1.4205(17) . ?
C5A C4A 1.4124(19) . ?
C8 H8 0.9500 . ?
C8 C7 1.4137(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.3693(19) . ?
C9A H9A 0.9500 . ?
C9A C8A 1.3736(17) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.3638(18) . ?
C7 H7 0.9500 . ?
C6A H6A 0.9500 . ?
C6A C7A 1.364(2) . ?
C4A H4A 0.9500 . ?
C8A H8A 0.9500 . ?
C8A C7A 1.411(2) . ?
C7A H7A 0.9500 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C12 C11 1.496(2) . ?
C13 H13D 0.9800 . ?
C13 H13E 0.9800 . ?
C13 H13F 0.9800 . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?

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
C1A O2A C11A 114.60(9) . . ?
C1 O2 C11 114.65(10) . . ?
C13A O3A C12A 114.46(10) . . ?
C12 O3 C13 111.12(11) . . ?
C2 N1 C10 118.30(10) . . ?
C2A N2A H2A 116.6 . . ?
C1A N2A H2A 116.6 . . ?
C1A N2A C2A 126.71(10) . . ?
C2A N1A C10A 118.64(10) . . ?
C2 N2 H2 117.1 . . ?
C1 N2 H2 117.1 . . ?
C1 N2 C2 125.88(10) . . ?
N2A C2A C3A 123.09(11) . . ?
N1A C2A N2A 113.34(10) . . ?
N1A C2A C3A 123.54(11) . . ?
O2A C1A N2A 108.47(10) . . ?
O1A C1A O2A 123.92(11) . . ?
O1A C1A N2A 127.60(11) . . ?
N1 C10 C5 122.22(11) . . ?
N1 C10 C9 118.66(11) . . ?
C9 C10 C5 119.12(11) . . ?
N1 C2 N2 114.40(10) . . ?
N1 C2 C3 123.64(11) . . ?
N2 C2 C3 121.90(11) . . ?
C4 C5 C10 117.14(11) . . ?
C4 C5 C6 123.46(11) . . ?
C6 C5 C10 119.39(11) . . ?
O2 C1 N2 108.31(10) . . ?
O1 C1 O2 124.95(11) . . ?
O1 C1 N2 126.74(11) . . ?
N1A C10A C5A 122.01(11) . . ?
N1A C10A C9A 118.26(11) . . ?
C9A C10A C5A 119.73(11) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.65(11) . . ?
C3 C4 H4 119.7 . . ?
C10 C9 H9 119.8 . . ?
C8 C9 C10 120.45(12) . . ?
C8 C9 H9 119.8 . . ?
O2A C11A H11A 109.8 . . ?
O2A C11A H11B 109.8 . . ?
O2A C11A C12A 109.18(10) . . ?
H11A C11A H11B 108.3 . . ?
C12A C11A H11A 109.8 . . ?
C12A C11A H11B 109.8 . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 118.03(11) . . ?
C4 C3 H3 121.0 . . ?
O3A C12A C11A 113.75(10) . . ?
O3A C12A H12A 108.8 . . ?
O3A C12A H12B 108.8 . . ?
C11A C12A H12A 108.8 . . ?
C11A C12A H12B 108.8 . . ?
H12A C12A H12B 107.7 . . ?
C10A C5A C6A 118.81(12) . . ?
C4A C5A C10A 116.96(11) . . ?
C4A C5A C6A 124.23(12) . . ?
C9 C8 H8 119.8 . . ?
C9 C8 C7 120.31(12) . . ?
C7 C8 H8 119.8 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.24(11) . . ?
C7 C6 H6 119.9 . . ?
C10A C9A H9A 120.0 . . ?
C8A C9A C10A 120.04(12) . . ?
C8A C9A H9A 120.0 . . ?
C2A C3A H3A 121.1 . . ?
C4A C3A C2A 117.77(12) . . ?
C4A C3A H3A 121.1 . . ?
C8 C7 H7 119.8 . . ?
C6 C7 C8 120.47(11) . . ?
C6 C7 H7 119.8 . . ?
C5A C6A H6A 119.8 . . ?
C7A C6A C5A 120.37(13) . . ?
C7A C6A H6A 119.8 . . ?
C5A C4A H4A 119.5 . . ?
C3A C4A C5A 121.01(12) . . ?
C3A C4A H4A 119.5 . . ?
C9A C8A H8A 119.8 . . ?
C9A C8A C7A 120.40(13) . . ?
C7A C8A H8A 119.8 . . ?
C6A C7A C8A 120.59(12) . . ?
C6A C7A H7A 119.7 . . ?
C8A C7A H7A 119.7 . . ?
O3A C13A H13A 109.5 . . ?
O3A C13A H13B 109.5 . . ?
O3A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
O3 C12 H12C 109.6 . . ?
O3 C12 H12D 109.6 . . ?
O3 C12 C11 110.12(12) . . ?
H12C C12 H12D 108.1 . . ?
C11 C12 H12C 109.6 . . ?
C11 C12 H12D 109.6 . . ?
O3 C13 H13D 109.5 . . ?
O3 C13 H13E 109.5 . . ?
O3 C13 H13F 109.5 . . ?
H13D C13 H13E 109.5 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
O2 C11 C12 108.61(11) . . ?
O2 C11 H11C 110.0 . . ?
O2 C11 H11D 110.0 . . ?
C12 C11 H11C 110.0 . . ?
C12 C11 H11D 110.0 . . ?
H11C C11 H11D 108.3 . . ?

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
O2A C11A C12A O3A 82.32(12) . . . . ?
O3 C12 C11 O2 -76.44(15) . . . . ?
N1 C10 C5 C4 -2.13(17) . . . . ?
N1 C10 C5 C6 179.40(11) . . . . ?
N1 C10 C9 C8 -179.96(11) . . . . ?
N1 C2 C3 C4 -0.62(18) . . . . ?
N2A C2A C3A C4A 179.88(11) . . . . ?
N1A C2A C3A C4A -1.88(18) . . . . ?
N1A C10A C5A C6A 177.07(11) . . . . ?
N1A C10A C5A C4A -2.87(17) . . . . ?
N1A C10A C9A C8A -176.94(11) . . . . ?
N2 C2 C3 C4 -177.67(11) . . . . ?
C2A N2A C1A O2A -177.73(10) . . . . ?
C2A N2A C1A O1A 3.3(2) . . . . ?
C2A N1A C10A C5A 2.07(17) . . . . ?
C2A N1A C10A C9A -178.37(11) . . . . ?
C2A C3A C4A C5A 0.95(19) . . . . ?
C1A O2A C11A C12A 177.70(10) . . . . ?
C1A N2A C2A N1A 166.80(11) . . . . ?
C1A N2A C2A C3A -14.80(18) . . . . ?
C10 N1 C2 N2 177.15(10) . . . . ?
C10 N1 C2 C3 -0.11(17) . . . . ?
C10 C5 C4 C3 1.36(17) . . . . ?
C10 C5 C6 C7 0.87(18) . . . . ?
C10 C9 C8 C7 0.22(18) . . . . ?
C2 N1 C10 C5 1.52(17) . . . . ?
C2 N1 C10 C9 -179.13(11) . . . . ?
C2 N2 C1 O2 -179.77(11) . . . . ?
C2 N2 C1 O1 0.6(2) . . . . ?
C5 C10 C9 C8 -0.60(17) . . . . ?
C5 C4 C3 C2 -0.07(18) . . . . ?
C5 C6 C7 C8 -1.27(18) . . . . ?
C1 O2 C11 C12 -176.38(11) . . . . ?
C1 N2 C2 N1 153.68(11) . . . . ?
C1 N2 C2 C3 -29.01(18) . . . . ?
C10A N1A C2A N2A 178.76(10) . . . . ?
C10A N1A C2A C3A 0.37(17) . . . . ?
C10A C5A C6A C7A 0.70(19) . . . . ?
C10A C5A C4A C3A 1.27(18) . . . . ?
C10A C9A C8A C7A -0.98(19) . . . . ?
C4 C5 C6 C7 -177.49(12) . . . . ?
C9 C10 C5 C4 178.53(11) . . . . ?
C9 C10 C5 C6 0.06(17) . . . . ?
C9 C8 C7 C6 0.73(19) . . . . ?
C11A O2A C1A O1A 5.13(16) . . . . ?
C11A O2A C1A N2A -173.87(9) . . . . ?
C5A C10A C9A C8A 2.63(18) . . . . ?
C5A C6A C7A C8A 0.9(2) . . . . ?
C6 C5 C4 C3 179.75(11) . . . . ?
C9A C10A C5A C6A -2.48(18) . . . . ?
C9A C10A C5A C4A 177.58(11) . . . . ?
C9A C8A C7A C6A -0.8(2) . . . . ?
C6A C5A C4A C3A -178.66(13) . . . . ?
C4A C5A C6A C7A -179.36(13) . . . . ?
C13A O3A C12A C11A -90.28(13) . . . . ?
C13 O3 C12 C11 -176.62(11) . . . . ?
C11 O2 C1 O1 -13.03(19) . . . . ?
C11 O2 C1 N2 167.29(11) . . . . ?

_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 2.481
_oxdiff_exptl_absorpt_empirical_full_min 0.658
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,2-dichloroethane'
####################################################################### 
# 
# 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_bsc-296
_database_code_depnum_ccdc_archive 'CCDC 2050680'
loop_
_audit_author_name
_audit_author_address
'Sergey Baykov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;
_audit_creation_date             2020-12-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Cyclohexyl (4--methylpyridin--2--yl)carbamate'
_chemical_formula_moiety         'C13 H18 N2 O2'
_chemical_formula_sum            'C13 H18 N2 O2'
_chemical_formula_weight         234.29
_chemical_melting_point          444
_chemical_oxdiff_formula         'C9 H9 F3 N2 O2 '
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.3092(2)
_cell_length_b                   12.0788(4)
_cell_length_c                   11.8379(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.429(3)
_cell_angle_gamma                90
_cell_volume                     1187.05(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3524
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0200
_cell_measurement_theta_min      5.2220
_shelx_estimated_absorpt_T_max   0.919
_shelx_estimated_absorpt_T_min   0.887
_exptl_absorpt_coefficient_mu    0.719
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0425
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10645
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.149
_diffrn_reflns_theta_min         5.234
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -65.00  33.00   1.00    9.63    --  -41.44  38.00 150.00   98
  2  ω      3.00  29.00   1.00    9.63    --  -41.44  77.00-150.00   26
  3  ω    -73.00 -11.00   1.00    9.63    --  -41.44  77.00-150.00   62
  4  ω    -93.00 -40.00   1.00    9.63    --  -41.44 178.00-180.00   53
  5  ω    104.00 175.00   1.00   38.52    --  112.00  77.00-150.00   71
  6  ω     42.00  89.00   1.00   38.52    --  112.00 -77.00-120.00   47
  7  ω     46.00 103.00   1.00   38.52    --  112.00-126.00   0.00   57
  8  ω     42.00  96.00   1.00   38.52    --  112.00-126.00 150.00   54
  9  ω     85.00 178.00   1.00   38.52    --  112.00  30.00 -60.00   93
 10  ω     41.00 107.00   1.00   38.52    --  112.00 -61.00 150.00   66
 11  ω     63.00  88.00   1.00   38.52    --  112.00 -61.00  30.00   25
 12  ω    106.00 136.00   1.00   38.52    --  112.00 -61.00  30.00   30
 13  ω     88.00 113.00   1.00   38.52    --  112.00-126.00-180.00   25
 14  ω    120.00 145.00   1.00   38.52    --  112.00 -77.00-120.00   25
 15  ω     46.00  72.00   1.00   38.52    --  112.00-126.00-180.00   26
 16  ω    -90.00 -63.00   1.00    9.63    --  -41.44 -38.00   0.00   27
 17  ω    -51.00 -23.00   1.00    9.63    --  -41.44 -38.00   0.00   28
 18  ω   -115.00 -39.00   1.00    9.63    --  -41.44 -38.00  90.00   76
 19  ω     83.00 130.00   1.00    9.63    --   41.44 178.00  90.00   47
 20  ω     79.00 105.00   1.00    9.63    --   41.44 178.00-180.00   26
 21  ω     61.00  87.00   1.00    9.63    --   41.44 178.00 -30.00   26
 22  ω     88.00 114.00   1.00   38.52    --  112.00  61.00-120.00   26
 23  ω    104.00 130.00   1.00   38.52    --  112.00  77.00 -60.00   26
 24  ω    139.00 173.00   1.00   38.52    --  112.00  77.00 -30.00   34
 25  ω    126.00 174.00   1.00   38.52    --  112.00  77.00   0.00   48
 26  ω    144.00 177.00   1.00   38.52    --  112.00  77.00  60.00   33
 27  ω    141.00 174.00   1.00   38.52    --  112.00  77.00 -60.00   33
 28  ω     61.00 100.00   1.00   38.52    --  112.00 -95.00-180.00   39
 29  ω    130.00 157.00   1.00   38.52    --  112.00 126.00  30.00   27
 30  ω    137.00 175.00   1.00   38.52    --  112.00  61.00  30.00   38
 31  ω     88.00 132.00   1.00   38.52    --  112.00  61.00  30.00   44
 32  ω     86.00 169.00   1.00   38.52    --  112.00  30.00  90.00   83
 33  ω     80.00 113.00   1.00   38.52    --  112.00-126.00 -30.00   33
 34  ω     60.00 104.00   1.00   38.52    --  112.00  15.00  60.00   44
 35  ω     88.00 113.00   1.00   38.52    --  112.00-126.00 -60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1429448000
_diffrn_orient_matrix_UB_12      -0.0662596000
_diffrn_orient_matrix_UB_13      0.0437761000
_diffrn_orient_matrix_UB_21      0.0211199000
_diffrn_orient_matrix_UB_22      -0.0869691000
_diffrn_orient_matrix_UB_23      -0.0934461000
_diffrn_orient_matrix_UB_31      0.1163797000
_diffrn_orient_matrix_UB_32      -0.0656992000
_diffrn_orient_matrix_UB_33      0.0795051000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2093
_reflns_number_total             2462
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     73.59
_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 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2462
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.047
_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)+(0.0544P)²+0.2470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0975
_refine_ls_wR_factor_ref         0.1032
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_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
O2 O 0.39016(11) 0.74402(8) 0.37247(7) 0.0184(2) Uani 1 1 d . . . . .
O1 O 0.23697(11) 0.70527(8) 0.52212(8) 0.0205(2) Uani 1 1 d . . . . .
N2 N 0.40981(13) 0.85419(9) 0.52130(9) 0.0176(2) Uani 1 1 d . . . . .
H2 H 0.474142 0.890854 0.477488 0.021 Uiso 1 1 calc R U . . .
N1 N 0.42214(12) 1.00377(9) 0.64104(9) 0.0173(2) Uani 1 1 d . . . . .
C1 C 0.33584(15) 0.76178(11) 0.47684(10) 0.0164(3) Uani 1 1 d . . . . .
C8 C 0.33433(15) 0.64386(10) 0.31336(10) 0.0159(3) Uani 1 1 d . . . . .
H8 H 0.214369 0.638350 0.314944 0.019 Uiso 1 1 calc R U . . .
C2 C 0.39177(14) 0.89527(11) 0.63056(10) 0.0160(3) Uani 1 1 d . . . . .
C3 C 0.35509(14) 0.82738(11) 0.72170(10) 0.0167(3) Uani 1 1 d . . . . .
H3 H 0.333755 0.750819 0.710410 0.020 Uiso 1 1 calc R U . . .
C5 C 0.37915(15) 0.98729(11) 0.84035(11) 0.0187(3) Uani 1 1 d . . . . .
H5 H 0.374771 1.022335 0.911998 0.022 Uiso 1 1 calc R U . . .
C6 C 0.41419(15) 1.04772(11) 0.74514(11) 0.0185(3) Uani 1 1 d . . . . .
H6 H 0.433807 1.124803 0.753781 0.022 Uiso 1 1 calc R U . . .
C4 C 0.35031(14) 0.87369(11) 0.82910(10) 0.0169(3) Uani 1 1 d . . . . .
C9 C 0.41171(15) 0.54223(11) 0.36845(10) 0.0183(3) Uani 1 1 d . . . . .
H9A H 0.369525 0.532017 0.444720 0.022 Uiso 1 1 calc R U . . .
H9B H 0.529596 0.553489 0.377139 0.022 Uiso 1 1 calc R U . . .
C11 C 0.43403(16) 0.45330(11) 0.17742(11) 0.0215(3) Uani 1 1 d . . . . .
H11A H 0.407270 0.386372 0.132156 0.026 Uiso 1 1 calc R U . . .
H11B H 0.552448 0.462912 0.179756 0.026 Uiso 1 1 calc R U . . .
C12 C 0.35334(16) 0.55453(11) 0.12175(11) 0.0207(3) Uani 1 1 d . . . . .
H12A H 0.395240 0.565182 0.045459 0.025 Uiso 1 1 calc R U . . .
H12B H 0.235788 0.541718 0.113076 0.025 Uiso 1 1 calc R U . . .
C13 C 0.38509(16) 0.65896(11) 0.19236(10) 0.0189(3) Uani 1 1 d . . . . .
H13A H 0.501314 0.677071 0.192807 0.023 Uiso 1 1 calc R U . . .
H13B H 0.324881 0.721768 0.157345 0.023 Uiso 1 1 calc R U . . .
C10 C 0.37697(16) 0.43829(11) 0.29750(11) 0.0209(3) Uani 1 1 d . . . . .
H10A H 0.432707 0.374045 0.333341 0.025 Uiso 1 1 calc R U . . .
H10B H 0.259806 0.423026 0.294638 0.025 Uiso 1 1 calc R U . . .
C7 C 0.32018(16) 0.80306(12) 0.93065(11) 0.0211(3) Uani 1 1 d . . . . .
H7A H 0.265140 0.734829 0.906285 0.032 Uiso 1 1 calc R U . . .
H7B H 0.252620 0.843792 0.982316 0.032 Uiso 1 1 calc R U . . .
H7C H 0.423141 0.784533 0.969519 0.032 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
O2 C1 1.3504(15) . ?
O2 C8 1.4632(15) . ?
O1 C1 1.2105(16) . ?
N2 H2 0.8800 . ?
N2 C1 1.3687(16) . ?
N2 C2 1.3992(16) . ?
N1 C2 1.3394(17) . ?
N1 C6 1.3460(17) . ?
C8 H8 1.0000 . ?
C8 C9 1.5199(17) . ?
C8 C13 1.5212(16) . ?
C2 C3 1.3990(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.3912(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3841(18) . ?
C5 C4 1.3983(19) . ?
C6 H6 0.9500 . ?
C4 C7 1.5037(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5311(18) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5302(19) . ?
C11 C10 1.5282(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5298(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 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
C1 O2 C8 117.22(10) . . ?
C1 N2 H2 117.2 . . ?
C1 N2 C2 125.50(11) . . ?
C2 N2 H2 117.2 . . ?
C2 N1 C6 117.03(11) . . ?
O2 C1 N2 108.62(10) . . ?
O1 C1 O2 125.10(12) . . ?
O1 C1 N2 126.27(12) . . ?
O2 C8 H8 110.0 . . ?
O2 C8 C9 110.05(10) . . ?
O2 C8 C13 104.85(10) . . ?
C9 C8 H8 110.0 . . ?
C9 C8 C13 111.83(10) . . ?
C13 C8 H8 110.0 . . ?
N1 C2 N2 113.92(11) . . ?
N1 C2 C3 123.25(11) . . ?
C3 C2 N2 122.71(12) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.00(12) . . ?
C4 C3 H3 120.5 . . ?
C6 C5 H5 120.6 . . ?
C6 C5 C4 118.76(12) . . ?
C4 C5 H5 120.6 . . ?
N1 C6 C5 123.90(12) . . ?
N1 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
C3 C4 C5 118.05(12) . . ?
C3 C4 C7 120.98(12) . . ?
C5 C4 C7 120.95(12) . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C8 C9 C10 111.12(10) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C10 C11 C12 110.36(11) . . ?
C11 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C13 C12 C11 111.18(10) . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
C8 C13 C12 111.55(11) . . ?
C8 C13 H13A 109.3 . . ?
C8 C13 H13B 109.3 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 C10 C9 110.75(11) . . ?
C11 C10 H10A 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 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
O2 C8 C9 C10 -170.93(10) . . . . ?
O2 C8 C13 C12 173.18(10) . . . . ?
N2 C2 C3 C4 175.56(11) . . . . ?
N1 C2 C3 C4 -0.34(18) . . . . ?
C1 O2 C8 C9 -71.18(13) . . . . ?
C1 O2 C8 C13 168.41(10) . . . . ?
C1 N2 C2 N1 -155.63(12) . . . . ?
C1 N2 C2 C3 28.12(19) . . . . ?
C8 O2 C1 O1 -5.01(18) . . . . ?
C8 O2 C1 N2 175.62(10) . . . . ?
C8 C9 C10 C11 56.59(14) . . . . ?
C2 N2 C1 O2 -176.05(11) . . . . ?
C2 N2 C1 O1 4.6(2) . . . . ?
C2 N1 C6 C5 0.94(18) . . . . ?
C2 C3 C4 C5 1.41(17) . . . . ?
C2 C3 C4 C7 -176.71(11) . . . . ?
C6 N1 C2 N2 -177.06(11) . . . . ?
C6 N1 C2 C3 -0.83(18) . . . . ?
C6 C5 C4 C3 -1.31(18) . . . . ?
C6 C5 C4 C7 176.81(11) . . . . ?
C4 C5 C6 N1 0.13(19) . . . . ?
C9 C8 C13 C12 53.96(14) . . . . ?
C11 C12 C13 C8 -54.78(14) . . . . ?
C12 C11 C10 C9 -57.34(14) . . . . ?
C13 C8 C9 C10 -54.82(14) . . . . ?
C10 C11 C12 C13 56.47(14) . . . . ?

_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 2.070
_oxdiff_exptl_absorpt_empirical_full_min 0.510
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform'
####################################################################### 
# 
# 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_16831_ucm-32
_database_code_depnum_ccdc_archive 'CCDC 2050687'
loop_
_audit_author_name
_audit_author_address
'Sergey Baykov'
;Saint Petersburg State University
Russia
;
_audit_update_record             
;
2020-12-16 deposited with the CCDC.	2021-06-10 downloaded from the CCDC.
;
_audit_creation_date             2020-12-08
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Ethyl (4--methoxyquinolin--2--yl)carbamate'
_chemical_formula_moiety         'C13 H14 N2 O3'
_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_weight         246.26
_chemical_melting_point          429
_chemical_oxdiff_formula         'C13 H14 N2 O3 '
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9429(2)
_cell_length_b                   12.4375(2)
_cell_length_c                   12.8747(3)
_cell_angle_alpha                87.653(2)
_cell_angle_beta                 74.488(2)
_cell_angle_gamma                87.068(2)
_cell_volume                     1223.46(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16854
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.3370
_cell_measurement_theta_min      3.5430
_shelx_estimated_absorpt_T_max   0.918
_shelx_estimated_absorpt_T_min   0.890
_exptl_absorpt_coefficient_mu    0.796
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.71a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24817
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.829
_diffrn_reflns_theta_min         3.560
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.998
_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   -104.00 -78.00   0.50    0.20    --  -38.95-158.00   8.00   52
  2  ω    -32.00  -6.00   0.50    0.20    --  -38.95 118.00-111.00   52
  3  ω    -80.00 -48.00   0.50    0.20    --  -38.95 118.00-111.00   64
  4  ω     59.00  85.00   0.50    0.20    --   38.95-118.00 162.00   52
  5  ω     70.00  98.00   0.50    0.20    --   38.95-158.00   8.00   56
  6  ω     62.00 102.00   0.50    0.20    --   38.95 158.00  42.00   80
  7  ω    104.00 129.00   0.50    0.28    --  100.00 118.00-111.00   50
  8  ω     83.00 133.00   0.50    0.28    --  100.00-158.00   8.00  100
  9  ω     41.00 106.00   0.50    0.28    --  100.00-118.00 162.00  130
 10  ω     87.00 112.00   0.50    0.28    --  100.00 158.00  42.00   50
 11  ω    -68.00 -19.00   0.50    0.20    --  -38.95 -21.00-120.00   98
 12  ω    -66.00 -24.00   0.50    0.20    --  -38.95 -54.00 150.00   84
 13  ω   -103.00 -69.00   0.50    0.20    --  -38.95 -54.00 150.00   68
 14  ω    -88.00 -62.00   0.50    0.20    --  -38.95 158.00  42.00   52
 15  ω    -14.00  17.00   0.50    0.20    --  -38.95  54.00  60.00   62
 16  ω    -59.00 -20.00   0.50    0.20    --  -38.95  54.00  60.00   78
 17  ω   -107.00 -81.00   0.50    0.20    --  -38.95 -21.00-120.00   52
 18  ω     29.00  55.00   0.50    0.20    --   38.95  43.00-150.00   52
 19  ω     70.00 102.00   0.50    0.20    --   38.95  43.00-150.00   64
 20  ω    -26.00   2.00   0.50    0.20    --   38.95 -43.00-180.00   56
 21  ω     27.00  52.00   0.50    0.20    --   38.95 -65.00  60.00   50
 22  ω     27.00  52.00   0.50    0.20    --   38.95  32.00-180.00   50
 23  ω     28.00 104.00   0.50    0.20    --   38.95  21.00 -60.00  152
 24  ω     18.00  89.00   0.50    0.20    --   38.95-138.00  90.00  142
 25  ω      7.00  53.00   0.50    0.20    --   38.95 -43.00-180.00   92
 26  ω     23.00  98.00   0.50    0.20    --   38.95  43.00  30.00  150
 27  ω     37.00  62.00   0.50    0.20    --   38.95-138.00 -60.00   50
 28  ω     77.00 102.00   0.50    0.20    --   38.95  32.00-180.00   50
 29  ω     20.00  97.00   0.50    0.20    --   38.95  54.00 120.00  154
 30  ω    -26.00  11.00   0.50    0.20    --   38.95 -65.00  60.00   74
 31  ω     31.00  57.00   0.50    0.28    --  100.00 -93.00 -90.00   52
 32  ω     30.00 129.00   0.50    0.28    --  100.00 -86.00 150.00  198
 33  ω    125.00 151.00   0.50    0.28    --  100.00 133.00-150.00   52
 34  ω     39.00  68.00   0.50    0.28    --  100.00-133.00  90.00   58
 35  ω    120.00 146.00   0.50    0.28    --  100.00  77.00  90.00   52
 36  ω     37.00 114.00   0.50    0.28    --  100.00 -30.00 -90.00  154
 37  ω     35.00  61.00   0.50    0.28    --  100.00 -61.00   0.00   52
 38  ω     86.00 127.00   0.50    0.28    --  100.00  37.00 -90.00   82
 39  ω     79.00 108.00   0.50    0.28    --  100.00-111.00  30.00   58
 40  ω     81.00 112.00   0.50    0.28    --  100.00  53.00-150.00   62
 41  ω     91.00 116.00   0.50    0.28    --  100.00  77.00  90.00   50
 42  ω     51.00 108.00   0.50    0.28    --  100.00-111.00 -30.00  114
 43  ω     74.00 112.00   0.50    0.28    --  100.00 -22.00 120.00   76
 44  ω     90.00 118.00   0.50    0.28    --  100.00 133.00-150.00   56
 45  ω    119.00 151.00   0.50    0.28    --  100.00  15.00  30.00   64
 46  ω     81.00 114.00   0.50    0.28    --  100.00  22.00  90.00   66
 47  ω     71.00 122.00   0.50    0.28    --  100.00 -61.00-180.00  102
 48  ω     28.00  64.00   0.50    0.28    --  100.00 -22.00 120.00   72
 49  ω     72.00 125.00   0.50    0.28    --  100.00 -77.00   0.00  106
 50  ω    124.00 156.00   0.50    0.28    --  100.00  30.00 120.00   64
 51  ω     86.00 115.00   0.50    0.28    --  100.00  30.00 120.00   58
 52  ω     44.00 109.00   0.50    0.28    --  100.00-133.00 120.00  130
 53  ω     27.00  95.00   0.50    0.28    --  100.00 -93.00 -30.00  136
 54  ω     56.00 115.00   0.50    0.28    --  100.00 -53.00 120.00  118
 55  ω     79.00 157.00   0.50    0.28    --  100.00  69.00 -90.00  156
 56  ω    131.00 156.00   0.50    0.28    --  100.00  22.00  90.00   50
 57  ω     52.00  77.00   0.50    0.28    --  100.00-111.00-120.00   50
 58  ω    106.00 133.00   0.50    0.28    --  100.00 111.00 150.00   54
 59  ω    125.00 152.00   0.50    0.28    --  100.00  22.00-180.00   54
 60  ω     92.00 132.00   0.50    0.28    --  100.00  93.00  30.00   80
 61  ω     41.00 115.00   0.50    0.28    --  100.00-133.00 150.00  148
 62  ω     35.00  62.00   0.50    0.28    --  100.00 -93.00-180.00   54
 63  ω     77.00 102.00   0.50    0.28    --  100.00 -93.00-180.00   50
 64  ω     88.00 116.00   0.50    0.28    --  100.00  22.00-180.00   56
 65  ω     69.00  94.00   0.50    0.28    --  100.00 -61.00  60.00   50
 66  ω     91.00 117.00   0.50    0.28    --  100.00 -61.00   0.00   52
 67  ω     97.00 123.00   0.50    0.28    --  100.00 178.00  90.00   52
 68  ω     58.00  84.00   0.50    0.28    --  100.00-111.00-180.00   52
 69  ω    117.00 142.00   0.50    0.28    --  100.00  53.00-150.00   50
 70  ω     64.00 118.00   0.50    0.28    --  100.00-133.00 -30.00  108
 71  ω     73.00 108.00   0.50    0.28    --  100.00 -22.00-120.00   70
 72  ω     42.00  68.00   0.50    0.28    --  100.00 178.00  90.00   52
 73  ω    104.00 154.00   0.50    0.28    --  100.00  77.00 -60.00  100
 74  ω     49.00 122.00   0.50    0.28    --  100.00 -61.00 -60.00  146
 75  ω     78.00 103.00   0.50    0.28    --  100.00  15.00  30.00   50
 76  ω      4.00  29.00   0.50    0.20    --   38.95-118.00 162.00   50
 77  ω    -30.00  -5.00   0.50    0.20    --   12.00 111.00 -28.76   50
 78  ω    -23.00   2.00   0.50    0.20    --   20.00 113.00 138.68   50
 79  ω    -17.00   9.00   0.50    0.20    --   20.00 106.00-148.08   52
 80  ω    -43.00 -18.00   0.50    0.20    --   24.00 150.00   0.48   50
 81  ω      2.00  27.00   0.50    0.20    --   32.00  86.00  56.06   50
 82  ω      1.00  26.00   0.50    0.20    --   32.00  88.00-137.10   50
 83  ω      1.00  26.00   0.50    0.20    --   32.00  88.00 -53.68   50
 84  ω      1.00  26.00   0.50    0.20    --   32.00  88.00-179.55   50
 85  ω      8.00  34.00   0.50    0.20    --   36.00  82.00  12.54   52
 86  ω      7.00  32.00   0.50    0.20    --   36.00  83.00 -59.68   50
 87  ω     12.00  37.00   0.50    0.20    --   38.95  79.00-136.83   50
 88  ω     -8.00  36.00   0.50    0.20    --   38.95 -43.00 150.00   88
 89  ω     12.00  38.00   0.50    0.20    --   40.00  82.00 168.69   52
 90  ω     16.00  41.00   0.50    0.20    --   44.00  81.00  89.24   50
 91  ω     16.00  41.00   0.50    0.20    --   44.00  81.00 132.42   50
 92  ω     16.00  41.00   0.50    0.20    --   44.00  82.00 -34.40   50
 93  ω     16.00  41.00   0.50    0.20    --   44.00  82.00-105.31   50
 94  ω     16.00  41.00   0.50    0.20    --   44.00  81.00  99.75   50
 95  ω     16.00  41.00   0.50    0.20    --   44.00  80.00 -89.81   50
 96  ω     16.00  41.00   0.50    0.20    --   44.00  81.00  56.58   50
 97  ω     23.00  55.00   0.50    0.20    --   48.00  73.00 146.75   64
 98  ω     91.00 117.00   0.50    0.20    --   52.00  73.00   3.43   52
 99  ω     28.00  54.00   0.50    0.20    --   52.00  73.00   3.43   52
100  ω     28.00  54.00   0.50    0.20    --   52.00  70.00-139.72   52
101  ω     34.00  60.00   0.50    0.20    --   56.00  67.00-103.86   52
102  ω     31.00  57.00   0.50    0.20    --   56.00  74.00  45.25   52
103  ω     36.00  62.00   0.50    0.20    --   60.00  68.00 -32.06   52
104  ω     36.00  70.00   0.50    0.20    --   60.00  71.00 -95.38   68
105  ω     34.00  60.00   0.50    0.20    --   60.00  74.00 -64.02   52
106  ω     86.00 112.00   0.50    0.20    --   60.00  71.00 -95.38   52
107  ω     86.00 124.00   0.50    0.20    --   60.00  74.00 -64.02   76
108  ω     41.00  69.00   0.50    0.20    --   64.00  66.00  77.89   56
109  ω     99.00 125.00   0.50    0.20    --   64.00  66.00  77.89   52
110  ω     45.00  96.00   0.50    0.20    --   64.00  58.00  46.28  102
111  ω     98.00 129.00   0.50    0.20    --   68.00  72.00 115.92   62
112  ω     43.00  87.00   0.50    0.20    --   68.00  72.00 115.92   88
113  ω     50.00  75.00   0.50    0.28    --   72.00  61.00  12.63   50
114  ω     55.00  81.00   0.50    0.28    --   76.00  69.00-131.13   52
115  ω     52.00  78.00   0.50    0.28    --   76.00  70.00-166.06   52
116  ω    106.00 132.00   0.50    0.28    --   76.00  69.00-131.13   52
117  ω    115.00 142.00   0.50    0.28    --   76.00  68.00 -55.41   54
118  ω     55.00  80.00   0.50    0.28    --   76.00  58.00 158.99   50
119  ω     53.00  78.00   0.50    0.28    --   76.00  70.00 -32.93   50
120  ω     52.00  78.00   0.50    0.28    --   76.00  68.00 -55.41   52
121  ω     92.00 118.00   0.50    0.28    --   76.00  58.00 158.99   52
122  ω     55.00  86.00   0.50    0.28    --   80.00  72.00  96.37   62
123  ω     54.00  80.00   0.50    0.28    --   80.00  74.00-158.97   52
124  ω     90.00 115.00   0.50    0.28    --   84.00  73.00 155.12   50
125  ω     59.00 103.00   0.50    0.28    --   84.00  71.00  58.54   88
126  ω     59.00  85.00   0.50    0.28    --   84.00  73.00 155.12   52
127  ω     82.00 108.00   0.50    0.28    --  100.00  53.00-180.00   52
128  ω     76.00 106.00   0.50    0.28    --  100.00  69.00  30.00   60
129  ω    105.00 131.00   0.50    0.28    --  100.00  69.00  90.00   52
130  ω     76.00 139.00   0.50    0.28    --  100.00  69.00 -30.00  126
131  ω     76.00 102.00   0.50    0.28    --  100.00  69.00  90.00   52
132  ω    131.00 157.00   0.50    0.28    --  100.00  69.00 120.00   52
133  ω     76.00 102.00   0.50    0.28    --  100.00  69.00 120.00   52
134  ω    124.00 150.00   0.50    0.28    --  100.00  69.00-180.00   52
135  ω     76.00 101.00   0.50    0.28    --  100.00  69.00-180.00   50
136  ω     77.00 103.00   0.50    0.28    --  100.00  67.00 105.13   52
137  ω    132.00 157.00   0.50    0.28    --  100.00  67.00 105.13   50
138  ω    125.00 150.00   0.50    0.28    --  100.00  69.00-102.16   50
139  ω     76.00 101.00   0.50    0.28    --  100.00  69.00-102.16   50
140  ω     85.00 140.00   0.50    0.28    --  100.00 111.00 -90.00  110
141  ω     76.00 106.00   0.50    0.28    --  100.00 -37.00   0.00   60
142  ω     33.00  63.00   0.50    0.28    --  100.00 -37.00   0.00   60
143  ω    109.00 135.00   0.50    0.28    --  100.00  93.00 120.00   52
144  ω    121.00 156.00   0.50    0.28    --  100.00  73.00-142.20   70
145  ω     36.00  66.00   0.50    0.28    --  100.00-133.00-120.00   60
146  ω     83.00 108.00   0.50    0.28    --  100.00  77.00 120.00   50
147  ω    125.00 155.00   0.50    0.28    --  100.00  61.00  30.00   60
148  ω    109.00 135.00   0.50    0.28    --  100.00 111.00-180.00   52
149  ω    108.00 134.00   0.50    0.28    --  100.00  61.00-120.00   52
150  ω     78.00 103.00   0.50    0.28    --  100.00  61.00  30.00   50
151  ω     75.00 100.00   0.50    0.28    --  100.00  73.00-142.20   50
152  ω     78.00 104.00   0.50    0.28    --  100.00  61.00-120.00   52
153  ω     80.00 115.00   0.50    0.28    --  100.00  53.00  30.00   70
154  ω     83.00 118.00   0.50    0.28    --  100.00  77.00 -90.00   70
155  ω     28.00  66.00   0.50    0.28    --  100.00 -22.00-150.00   76
156  ω     76.00 101.00   0.50    0.28    --  100.00  69.00-120.00   50
157  ω     78.00 115.00   0.50    0.28    --  100.00 -37.00 150.00   74
158  ω    106.00 151.00   0.50    0.28    --  100.00  93.00  90.00   90
159  ω    120.00 146.00   0.50    0.28    --  100.00  69.00-150.00   52
160  ω     44.00  70.00   0.50    0.28    --  100.00 -37.00 150.00   52
161  ω    132.00 157.00   0.50    0.28    --  100.00  61.00   0.00   50
162  ω     76.00 115.00   0.50    0.28    --  100.00  69.00-150.00   78
163  ω     76.00 127.00   0.50    0.28    --  100.00  69.00  60.00  102
164  ω    124.00 150.00   0.50    0.28    --  100.00  69.00 150.00   52
165  ω     77.00 114.00   0.50    0.28    --  100.00  69.00 150.00   74
166  ω     77.00 122.00   0.50    0.28    --  100.00  69.00   0.00   90
167  ω     76.00 103.00   0.50    0.28    --  100.00  69.00 -60.00   54
168  ω    123.00 149.00   0.50    0.28    --  100.00  53.00-180.00   52
169  ω     78.00 109.00   0.50    0.28    --  100.00  61.00   0.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'SuperNova, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0652973000
_diffrn_orient_matrix_UB_12      -0.1107261000
_diffrn_orient_matrix_UB_13      -0.0480486000
_diffrn_orient_matrix_UB_21      -0.0598811000
_diffrn_orient_matrix_UB_22      -0.0535068000
_diffrn_orient_matrix_UB_23      0.1131411000
_diffrn_orient_matrix_UB_31      -0.1809361000
_diffrn_orient_matrix_UB_32      -0.0164834000
_diffrn_orient_matrix_UB_33      -0.0180006000
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4265
_reflns_number_total             4672
_reflns_odcompleteness_completeness 98.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.71a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4672
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0368
_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)+(0.0547P)²+0.2813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1021
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11A(H11A,H11B), C11(H11C,H11D)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N2A(H2A), C3(H3), C3A(H3A), C9A(H9A), C6A(H6A), C9(H9), C8(H8),
 C7A(H7A), C6(H6), C8A(H8A), C7(H7)
2.c Idealised Me refined as rotating group:
 C13A(H13A,H13B,H13C), C13(H13D,H13E,H13F), C12A(H12A,H12B,H12C), C12(H12D,
 H12E,H12F)
;
_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
O2A O 0.85578(10) 0.21477(7) 0.20308(6) 0.0245(2) Uani 1 1 d . . . . .
O3A O 0.55387(11) 0.02649(6) 0.70782(6) 0.0240(2) Uani 1 1 d . . . . .
O3 O 0.25423(11) 0.50349(7) -0.00512(6) 0.0257(2) Uani 1 1 d . . . . .
O2 O 0.26954(12) 0.47028(7) 0.50915(6) 0.0269(2) Uani 1 1 d . . . . .
O1A O 0.92129(11) 0.13893(8) 0.35141(7) 0.0318(2) Uani 1 1 d . . . . .
O1 O 0.25389(15) 0.58047(7) 0.36768(7) 0.0391(3) Uani 1 1 d . . . . .
N1 N 0.43252(12) 0.29397(8) 0.20615(7) 0.0201(2) Uani 1 1 d . . . . .
N2 N 0.31356(13) 0.39748(8) 0.35126(7) 0.0221(2) Uani 1 1 d . . . . .
H2 H 0.319013 0.338625 0.390761 0.026 Uiso 1 1 calc R U . . .
N1A N 0.38260(13) 0.20969(8) 0.47626(7) 0.0207(2) Uani 1 1 d . . . . .
N2A N 0.63942(13) 0.18899(8) 0.34805(7) 0.0215(2) Uani 1 1 d . . . . .
H2A H 0.579232 0.213613 0.303181 0.026 Uiso 1 1 calc R U . . .
C2 C 0.34403(15) 0.38423(9) 0.24066(9) 0.0198(2) Uani 1 1 d . . . . .
C10A C 0.27539(15) 0.19206(9) 0.57790(9) 0.0206(2) Uani 1 1 d . . . . .
C2A C 0.54338(15) 0.16730(9) 0.45426(9) 0.0203(2) Uani 1 1 d . . . . .
C4A C 0.50656(16) 0.08626(9) 0.62937(9) 0.0204(2) Uani 1 1 d . . . . .
C10 C 0.46166(15) 0.27233(9) 0.09886(9) 0.0206(2) Uani 1 1 d . . . . .
C5 C 0.40401(15) 0.34329(9) 0.02525(9) 0.0210(2) Uani 1 1 d . . . . .
C3 C 0.27816(15) 0.46055(9) 0.17489(9) 0.0210(2) Uani 1 1 d . . . . .
H3 H 0.214456 0.523971 0.204257 0.025 Uiso 1 1 calc R U . . .
C3A C 0.61417(15) 0.10507(9) 0.52812(9) 0.0207(2) Uani 1 1 d . . . . .
H3A H 0.731719 0.077345 0.508397 0.025 Uiso 1 1 calc R U . . .
C1 C 0.27614(16) 0.49193(10) 0.40499(9) 0.0238(3) Uani 1 1 d . . . . .
C4 C 0.30949(15) 0.43973(9) 0.06771(9) 0.0210(2) Uani 1 1 d . . . . .
C9A C 0.10358(16) 0.23791(9) 0.60241(10) 0.0241(3) Uani 1 1 d . . . . .
H9A H 0.063615 0.277323 0.548219 0.029 Uiso 1 1 calc R U . . .
C5A C 0.33169(15) 0.13106(9) 0.65853(9) 0.0203(2) Uani 1 1 d . . . . .
C6A C 0.21568(16) 0.11887(9) 0.76236(9) 0.0242(3) Uani 1 1 d . . . . .
H6A H 0.252075 0.077615 0.816834 0.029 Uiso 1 1 calc R U . . .
C1A C 0.81580(15) 0.17624(9) 0.30630(9) 0.0217(2) Uani 1 1 d . . . . .
C9 C 0.55085(15) 0.17441(9) 0.06055(10) 0.0245(3) Uani 1 1 d . . . . .
H9 H 0.589659 0.125536 0.108780 0.029 Uiso 1 1 calc R U . . .
C8 C 0.58160(16) 0.14971(10) -0.04629(10) 0.0276(3) Uani 1 1 d . . . . .
H8 H 0.640383 0.083372 -0.070985 0.033 Uiso 1 1 calc R U . . .
C7A C 0.05100(17) 0.16631(10) 0.78471(10) 0.0265(3) Uani 1 1 d . . . . .
H7A H -0.025384 0.159010 0.855106 0.032 Uiso 1 1 calc R U . . .
C6 C 0.43909(16) 0.31640(10) -0.08427(9) 0.0253(3) Uani 1 1 d . . . . .
H6 H 0.401551 0.364317 -0.133765 0.030 Uiso 1 1 calc R U . . .
C8A C -0.00596(16) 0.22586(10) 0.70407(10) 0.0257(3) Uani 1 1 d . . . . .
H8A H -0.120868 0.257829 0.720204 0.031 Uiso 1 1 calc R U . . .
C11A C 1.03903(15) 0.20774(10) 0.14491(9) 0.0239(3) Uani 1 1 d . . . . .
H11A H 1.111703 0.206846 0.196582 0.029 Uiso 1 1 calc R U . . .
H11B H 1.067949 0.271663 0.096118 0.029 Uiso 1 1 calc R U . . .
C13A C 0.72901(16) -0.01997(10) 0.68370(10) 0.0253(3) Uani 1 1 d . . . . .
H13A H 0.747984 -0.067470 0.622382 0.038 Uiso 1 1 calc R U . . .
H13B H 0.745709 -0.061667 0.746697 0.038 Uiso 1 1 calc R U . . .
H13C H 0.812718 0.037552 0.665583 0.038 Uiso 1 1 calc R U . . .
C7 C 0.52716(16) 0.22133(11) -0.11935(10) 0.0280(3) Uani 1 1 d . . . . .
H7 H 0.551409 0.203870 -0.193183 0.034 Uiso 1 1 calc R U . . .
C13 C 0.15494(17) 0.60036(10) 0.03250(10) 0.0286(3) Uani 1 1 d . . . . .
H13D H 0.138489 0.644274 -0.029270 0.043 Uiso 1 1 calc R U . . .
H13E H 0.217805 0.641041 0.072793 0.043 Uiso 1 1 calc R U . . .
H13F H 0.040626 0.582007 0.079683 0.043 Uiso 1 1 calc R U . . .
C12A C 1.07903(17) 0.10736(11) 0.08032(10) 0.0310(3) Uani 1 1 d . . . . .
H12A H 0.999830 0.105326 0.033757 0.046 Uiso 1 1 calc R U . . .
H12B H 1.063135 0.044041 0.129280 0.046 Uiso 1 1 calc R U . . .
H12C H 1.200240 0.107195 0.035771 0.046 Uiso 1 1 calc R U . . .
C12 C 0.2393(2) 0.51647(12) 0.68954(10) 0.0359(3) Uani 1 1 d . . . . .
H12D H 0.352591 0.479706 0.686260 0.054 Uiso 1 1 calc R U . . .
H12E H 0.146133 0.465186 0.714017 0.054 Uiso 1 1 calc R U . . .
H12F H 0.219721 0.575461 0.740156 0.054 Uiso 1 1 calc R U . . .
C11 C 0.2382(2) 0.56113(11) 0.57920(10) 0.0364(3) Uani 1 1 d . . . . .
H11C H 0.123871 0.597741 0.580967 0.044 Uiso 1 1 calc R U . . .
H11D H 0.330985 0.613650 0.553581 0.044 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
O2A C1A 1.3542(14) . ?
O2A C11A 1.4479(14) . ?
O3A C4A 1.3517(13) . ?
O3A C13A 1.4377(14) . ?
O3 C4 1.3508(14) . ?
O3 C13 1.4333(14) . ?
O2 C1 1.3445(14) . ?
O2 C11 1.4446(14) . ?
O1A C1A 1.2055(14) . ?
O1 C1 1.2070(15) . ?
N1 C2 1.3209(14) . ?
N1 C10 1.3737(14) . ?
N2 H2 0.8800 . ?
N2 C2 1.3944(14) . ?
N2 C1 1.3666(15) . ?
N1A C10A 1.3730(15) . ?
N1A C2A 1.3187(15) . ?
N2A H2A 0.8800 . ?
N2A C2A 1.3990(14) . ?
N2A C1A 1.3631(15) . ?
C2 C3 1.4185(16) . ?
C10A C9A 1.4113(16) . ?
C10A C5A 1.4150(16) . ?
C2A C3A 1.4145(16) . ?
C4A C3A 1.3727(16) . ?
C4A C5A 1.4282(16) . ?
C10 C5 1.4174(16) . ?
C10 C9 1.4151(16) . ?
C5 C4 1.4295(16) . ?
C5 C6 1.4130(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3682(16) . ?
C3A H3A 0.9500 . ?
C9A H9A 0.9500 . ?
C9A C8A 1.3714(17) . ?
C5A C6A 1.4135(16) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.3695(17) . ?
C9 H9 0.9500 . ?
C9 C8 1.3760(17) . ?
C8 H8 0.9500 . ?
C8 C7 1.4052(18) . ?
C7A H7A 0.9500 . ?
C7A C8A 1.4090(17) . ?
C6 H6 0.9500 . ?
C6 C7 1.3718(18) . ?
C8A H8A 0.9500 . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C11A C12A 1.5013(17) . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C7 H7 0.9500 . ?
C13 H13D 0.9800 . ?
C13 H13E 0.9800 . ?
C13 H13F 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C12 H12D 0.9800 . ?
C12 H12E 0.9800 . ?
C12 H12F 0.9800 . ?
C12 C11 1.5060(19) . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?

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
C1A O2A C11A 115.98(9) . . ?
C4A O3A C13A 117.75(9) . . ?
C4 O3 C13 117.66(9) . . ?
C1 O2 C11 116.57(9) . . ?
C2 N1 C10 117.46(10) . . ?
C2 N2 H2 116.5 . . ?
C1 N2 H2 116.5 . . ?
C1 N2 C2 127.07(10) . . ?
C2A N1A C10A 117.93(10) . . ?
C2A N2A H2A 116.4 . . ?
C1A N2A H2A 116.4 . . ?
C1A N2A C2A 127.28(10) . . ?
N1 C2 N2 113.69(10) . . ?
N1 C2 C3 124.76(10) . . ?
N2 C2 C3 121.51(10) . . ?
N1A C10A C9A 118.30(10) . . ?
N1A C10A C5A 122.44(10) . . ?
C9A C10A C5A 119.25(10) . . ?
N1A C2A N2A 112.90(10) . . ?
N1A C2A C3A 124.69(10) . . ?
N2A C2A C3A 122.40(10) . . ?
O3A C4A C3A 124.40(11) . . ?
O3A C4A C5A 115.11(10) . . ?
C3A C4A C5A 120.49(10) . . ?
N1 C10 C5 122.75(10) . . ?
N1 C10 C9 118.62(10) . . ?
C9 C10 C5 118.62(10) . . ?
C10 C5 C4 116.97(10) . . ?
C6 C5 C10 119.89(11) . . ?
C6 C5 C4 123.13(11) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 C2 117.74(10) . . ?
C4 C3 H3 121.1 . . ?
C2A C3A H3A 121.3 . . ?
C4A C3A C2A 117.46(10) . . ?
C4A C3A H3A 121.3 . . ?
O2 C1 N2 108.02(10) . . ?
O1 C1 O2 124.66(11) . . ?
O1 C1 N2 127.32(11) . . ?
O3 C4 C5 114.69(10) . . ?
O3 C4 C3 125.00(11) . . ?
C3 C4 C5 120.30(10) . . ?
C10A C9A H9A 119.8 . . ?
C8A C9A C10A 120.34(11) . . ?
C8A C9A H9A 119.8 . . ?
C10A C5A C4A 116.96(10) . . ?
C6A C5A C10A 119.31(11) . . ?
C6A C5A C4A 123.73(10) . . ?
C5A C6A H6A 119.9 . . ?
C7A C6A C5A 120.24(11) . . ?
C7A C6A H6A 119.9 . . ?
O2A C1A N2A 107.97(9) . . ?
O1A C1A O2A 124.59(11) . . ?
O1A C1A N2A 127.43(11) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 C10 120.27(11) . . ?
C8 C9 H9 119.9 . . ?
C9 C8 H8 119.6 . . ?
C9 C8 C7 120.86(11) . . ?
C7 C8 H8 119.6 . . ?
C6A C7A H7A 119.8 . . ?
C6A C7A C8A 120.48(11) . . ?
C8A C7A H7A 119.8 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.21(11) . . ?
C7 C6 H6 119.9 . . ?
C9A C8A C7A 120.35(11) . . ?
C9A C8A H8A 119.8 . . ?
C7A C8A H8A 119.8 . . ?
O2A C11A H11A 109.6 . . ?
O2A C11A H11B 109.6 . . ?
O2A C11A C12A 110.30(10) . . ?
H11A C11A H11B 108.1 . . ?
C12A C11A H11A 109.6 . . ?
C12A C11A H11B 109.6 . . ?
O3A C13A H13A 109.5 . . ?
O3A C13A H13B 109.5 . . ?
O3A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C8 C7 H7 119.9 . . ?
C6 C7 C8 120.13(11) . . ?
C6 C7 H7 119.9 . . ?
O3 C13 H13D 109.5 . . ?
O3 C13 H13E 109.5 . . ?
O3 C13 H13F 109.5 . . ?
H13D C13 H13E 109.5 . . ?
H13D C13 H13F 109.5 . . ?
H13E C13 H13F 109.5 . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
H12D C12 H12E 109.5 . . ?
H12D C12 H12F 109.5 . . ?
H12E C12 H12F 109.5 . . ?
C11 C12 H12D 109.5 . . ?
C11 C12 H12E 109.5 . . ?
C11 C12 H12F 109.5 . . ?
O2 C11 C12 106.33(11) . . ?
O2 C11 H11C 110.5 . . ?
O2 C11 H11D 110.5 . . ?
C12 C11 H11C 110.5 . . ?
C12 C11 H11D 110.5 . . ?
H11C C11 H11D 108.7 . . ?

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
O3A C4A C3A C2A 178.49(10) . . . . ?
O3A C4A C5A C10A -178.51(9) . . . . ?
O3A C4A C5A C6A 2.43(16) . . . . ?
N1 C2 C3 C4 -0.50(18) . . . . ?
N1 C10 C5 C4 -1.08(17) . . . . ?
N1 C10 C5 C6 179.68(10) . . . . ?
N1 C10 C9 C8 179.65(11) . . . . ?
N2 C2 C3 C4 -178.03(11) . . . . ?
N1A C10A C9A C8A -177.53(11) . . . . ?
N1A C10A C5A C4A -0.94(16) . . . . ?
N1A C10A C5A C6A 178.17(10) . . . . ?
N1A C2A C3A C4A 1.04(17) . . . . ?
N2A C2A C3A C4A -178.17(10) . . . . ?
C2 N1 C10 C5 1.26(16) . . . . ?
C2 N1 C10 C9 -177.84(10) . . . . ?
C2 N2 C1 O2 -175.31(11) . . . . ?
C2 N2 C1 O1 4.0(2) . . . . ?
C2 C3 C4 O3 179.25(10) . . . . ?
C2 C3 C4 C5 0.67(17) . . . . ?
C10A N1A C2A N2A 178.99(9) . . . . ?
C10A N1A C2A C3A -0.28(17) . . . . ?
C10A C9A C8A C7A -0.89(19) . . . . ?
C10A C5A C6A C7A -0.46(17) . . . . ?
C2A N1A C10A C9A 179.47(10) . . . . ?
C2A N1A C10A C5A 0.25(16) . . . . ?
C2A N2A C1A O2A -175.10(10) . . . . ?
C2A N2A C1A O1A 4.0(2) . . . . ?
C4A C5A C6A C7A 178.59(11) . . . . ?
C10 N1 C2 N2 177.25(9) . . . . ?
C10 N1 C2 C3 -0.45(17) . . . . ?
C10 C5 C4 O3 -178.65(10) . . . . ?
C10 C5 C4 C3 0.07(17) . . . . ?
C10 C5 C6 C7 0.68(18) . . . . ?
C10 C9 C8 C7 0.73(18) . . . . ?
C5 C10 C9 C8 0.52(17) . . . . ?
C5 C6 C7 C8 0.58(18) . . . . ?
C3A C4A C5A C10A 1.70(16) . . . . ?
C3A C4A C5A C6A -177.37(11) . . . . ?
C1 O2 C11 C12 -179.24(11) . . . . ?
C1 N2 C2 N1 158.40(11) . . . . ?
C1 N2 C2 C3 -23.82(18) . . . . ?
C4 C5 C6 C7 -178.52(11) . . . . ?
C9A C10A C5A C4A 179.85(10) . . . . ?
C9A C10A C5A C6A -1.04(16) . . . . ?
C5A C10A C9A C8A 1.72(18) . . . . ?
C5A C4A C3A C2A -1.73(16) . . . . ?
C5A C6A C7A C8A 1.31(19) . . . . ?
C6A C7A C8A C9A -0.64(19) . . . . ?
C1A O2A C11A C12A 95.16(12) . . . . ?
C1A N2A C2A N1A 165.71(11) . . . . ?
C1A N2A C2A C3A -15.00(18) . . . . ?
C9 C10 C5 C4 178.03(10) . . . . ?
C9 C10 C5 C6 -1.21(17) . . . . ?
C9 C8 C7 C6 -1.30(19) . . . . ?
C6 C5 C4 O3 0.56(16) . . . . ?
C6 C5 C4 C3 179.28(11) . . . . ?
C11A O2A C1A O1A 1.02(17) . . . . ?
C11A O2A C1A N2A -179.84(9) . . . . ?
C13A O3A C4A C3A 0.36(16) . . . . ?
C13A O3A C4A C5A -179.42(9) . . . . ?
C13 O3 C4 C5 178.56(10) . . . . ?
C13 O3 C4 C3 -0.10(17) . . . . ?
C11 O2 C1 O1 -1.78(19) . . . . ?
C11 O2 C1 N2 177.59(11) . . . . ?

_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 1.375
_oxdiff_exptl_absorpt_empirical_full_min 0.720
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1,2-dichloroethane'
