# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

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

data_79_HCl
_database_code_depnum_ccdc_archive 'CCDC 2127766'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-02-03 deposited with the CCDC.	2022-07-10 downloaded from the CCDC.
;
_audit_creation_date             2020-09-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 N2 O, Cl'
_chemical_formula_sum            'C15 H17 Cl N2 O'
_chemical_formula_weight         276.75
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   4.8798(3)
_cell_length_b                   17.8602(9)
_cell_length_c                   15.7045(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.206(3)
_cell_angle_gamma                90
_cell_volume                     1368.70(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3237
_cell_measurement_temperature    170
_cell_measurement_theta_max      27.878
_cell_measurement_theta_min      0.407
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.942
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0916 before and 0.0792 after correction. The Ratio of minimum to maximum transmission is 0.8139. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0877
_diffrn_reflns_av_unetI/netI     0.1030
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9378
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.334
_diffrn_reflns_theta_min         1.727
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1526
_reflns_number_total             2490
_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_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1287
_refine_ls_R_factor_gt           0.0712
_refine_ls_restrained_S_all      1.027
_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)+(0.0367P)²+2.3299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1286
_refine_ls_wR_factor_ref         0.1510
_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, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15)
2.c Idealised Me refined as rotating group:
 N17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2853(8) 0.5301(2) 0.2495(2) 0.0263(10) Uani 1 1 d . . . . .
C2 C -0.4086(8) 0.4815(2) 0.1924(2) 0.0283(10) Uani 1 1 d . . . . .
H2 H -0.3569 0.4302 0.1931 0.034 Uiso 1 1 calc R . . . .
C3 C -0.6049(9) 0.5050(2) 0.1341(3) 0.0329(10) Uani 1 1 d . . . . .
C4 C -0.6774(9) 0.5805(2) 0.1337(3) 0.0387(12) Uani 1 1 d . . . . .
H4 H -0.8114 0.5980 0.0945 0.046 Uiso 1 1 calc R . . . .
C5 C -0.5564(10) 0.6300(2) 0.1899(3) 0.0402(12) Uani 1 1 d . . . . .
H5 H -0.6076 0.6813 0.1889 0.048 Uiso 1 1 calc R . . . .
C6 C -0.3609(9) 0.6056(2) 0.2478(3) 0.0343(11) Uani 1 1 d . . . . .
H6 H -0.2786 0.6400 0.2862 0.041 Uiso 1 1 calc R . . . .
C7 C -0.0721(8) 0.5073(2) 0.3135(3) 0.0276(10) Uani 1 1 d . . . . .
O8 O 0.0194(6) 0.55183(14) 0.36606(18) 0.0360(8) Uani 1 1 d . . . . .
N9 N 0.0134(7) 0.43488(17) 0.3099(2) 0.0261(8) Uani 1 1 d . . . . .
H9 H -0.039(8) 0.409(2) 0.270(3) 0.031 Uiso 1 1 d R . . . .
C10 C 0.2172(8) 0.4002(2) 0.3613(2) 0.0256(9) Uani 1 1 d . . . . .
C11 C 0.2901(9) 0.4250(2) 0.4417(2) 0.0290(10) Uani 1 1 d . . . . .
H11 H 0.2062 0.4684 0.4649 0.035 Uiso 1 1 calc R . . . .
C12 C 0.4866(9) 0.3862(2) 0.4888(3) 0.0315(10) Uani 1 1 d . . . . .
H12 H 0.5355 0.4037 0.5439 0.038 Uiso 1 1 calc R . . . .
C13 C 0.6115(8) 0.3230(2) 0.4570(3) 0.0269(10) Uani 1 1 d . . . . .
C14 C 0.5356(9) 0.2982(2) 0.3761(3) 0.0295(10) Uani 1 1 d . . . . .
H14 H 0.6183 0.2545 0.3530 0.035 Uiso 1 1 calc R . . . .
C15 C 0.3414(8) 0.3365(2) 0.3292(2) 0.0279(10) Uani 1 1 d . . . . .
H15 H 0.2921 0.3190 0.2742 0.034 Uiso 1 1 calc R . . . .
C16 C 0.8325(9) 0.2793(2) 0.5035(3) 0.0328(11) Uani 1 1 d . . . . .
H16A H 0.7956 0.2251 0.4970 0.039 Uiso 1 1 calc R . . . .
H16B H 1.0117 0.2900 0.4767 0.039 Uiso 1 1 calc R . . . .
N17 N 0.8505(7) 0.29737(18) 0.5955(2) 0.0330(9) Uani 1 1 d . . . . .
H17A H 0.8725 0.3476 0.6022 0.040 Uiso 1 1 calc GR . . . .
H17B H 0.9961 0.2730 0.6190 0.040 Uiso 1 1 calc GR . . . .
H17C H 0.6938 0.2826 0.6219 0.040 Uiso 1 1 calc GR . . . .
C18 C -0.7329(10) 0.4500(2) 0.0733(3) 0.0441(13) Uani 1 1 d . . . . .
H18A H -0.6223 0.4043 0.0717 0.066 Uiso 1 1 calc GR . . . .
H18B H -0.7412 0.4721 0.0162 0.066 Uiso 1 1 calc GR . . . .
H18C H -0.9187 0.4379 0.0923 0.066 Uiso 1 1 calc GR . . . .
Cl19 Cl 0.3473(2) 0.20703(6) 0.66062(7) 0.0370(3) Uani 1 1 d . . . . .


_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
C1 C2 1.384(5) . ?
C1 C6 1.397(5) . ?
C1 C7 1.501(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(5) . ?
C3 C4 1.394(6) . ?
C3 C18 1.504(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.380(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(6) . ?
C6 H6 0.9500 . ?
C7 O8 1.229(4) . ?
C7 N9 1.360(5) . ?
N9 H9 0.82(4) . ?
N9 C10 1.421(5) . ?
C10 C11 1.383(5) . ?
C10 C15 1.385(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.378(5) . ?
C13 C14 1.394(5) . ?
C13 C16 1.516(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(5) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 N17 1.483(5) . ?
N17 H17A 0.9100 . ?
N17 H17B 0.9100 . ?
N17 H17C 0.9100 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C2 C1 C6 118.6(4) . . ?
C2 C1 C7 124.2(3) . . ?
C6 C1 C7 117.2(3) . . ?
C1 C2 H2 118.8 . . ?
C1 C2 C3 122.3(4) . . ?
C3 C2 H2 118.8 . . ?
C2 C3 C4 118.0(4) . . ?
C2 C3 C18 120.4(4) . . ?
C4 C3 C18 121.6(4) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.6(4) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 120.1 . . ?
C5 C6 C1 119.8(4) . . ?
C5 C6 H6 120.1 . . ?
O8 C7 C1 121.5(3) . . ?
O8 C7 N9 122.2(3) . . ?
N9 C7 C1 116.2(3) . . ?
C7 N9 H9 119(3) . . ?
C7 N9 C10 127.2(3) . . ?
C10 N9 H9 114(3) . . ?
C11 C10 N9 123.9(3) . . ?
C11 C10 C15 118.9(3) . . ?
C15 C10 N9 117.2(3) . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.0(4) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.3 . . ?
C13 C12 C11 121.3(4) . . ?
C13 C12 H12 119.3 . . ?
C12 C13 C14 118.3(4) . . ?
C12 C13 C16 124.2(4) . . ?
C14 C13 C16 117.5(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.5(4) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 121.0(4) . . ?
C14 C15 H15 119.5 . . ?
C13 C16 H16A 108.9 . . ?
C13 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
N17 C16 C13 113.4(3) . . ?
N17 C16 H16A 108.9 . . ?
N17 C16 H16B 108.9 . . ?
C16 N17 H17A 109.5 . . ?
C16 N17 H17B 109.5 . . ?
C16 N17 H17C 109.5 . . ?
H17A N17 H17B 109.5 . . ?
H17A N17 H17C 109.5 . . ?
H17B N17 H17C 109.5 . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_84
_database_code_depnum_ccdc_archive 'CCDC 2127765'
loop_
_audit_author_name
_audit_author_address
'Kari Rissanen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-02-03 deposited with the CCDC.	2022-07-10 downloaded from the CCDC.
;
_audit_creation_date             2020-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H19 N3 O'
_chemical_formula_sum            'C21 H19 N3 O'
_chemical_formula_weight         329.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   8.7084(3)
_cell_length_b                   10.2040(5)
_cell_length_c                   19.0448(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.691(4)
_cell_angle_gamma                90
_cell_volume                     1690.46(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2300
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      76.0290
_cell_measurement_theta_min      4.6420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.644
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.579
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43c (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             696
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -4 7 0.0185
-3 4 -7 0.0095
-4 -5 -2 0.1285
4 3 -8 0.0908
1 -2 -12 0.0890
-1 1 12 0.0917
-3 -1 10 0.1180
4 4 -2 0.1234
-1 2 12 0.0959
4 -5 -1 0.0633
-3 3 9 0.0886
-5 1 -5 0.0778
6 -1 0 0.0784
5 -1 6 0.0767

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.192
_exptl_crystal_size_min          0.028
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
2.9946 -3.9821 6.9855 -0.0434 0.9386 0.3282
-2.9946 3.9821 -6.9855 0.0434 -0.9386 -0.3282
-3.9873 -5.0029 -2.0046 1.0340 0.0747 -0.1802
3.9891 3.0032 -7.9992 -0.8042 -0.0899 -0.6536
0.9995 -1.9976 -12.0053 0.1015 0.0458 -1.0198
-0.9989 0.9994 12.0030 -0.0045 0.0656 0.9898
-2.9928 -1.0033 10.0019 0.4676 0.0234 0.8373
3.9881 4.0034 -1.9974 -0.9227 -0.0585 -0.1593
-0.9995 1.9976 12.0053 -0.1015 -0.0458 1.0198
3.9932 -4.9801 -1.0178 -0.0532 0.9682 -0.3520
-2.9950 2.9892 9.0111 0.0831 -0.4462 0.8799
-4.9881 0.9825 -4.9891 0.5982 -0.7741 -0.2012
5.9860 -0.9813 -0.0122 -0.7157 0.7637 -0.2169
4.9881 -0.9822 5.9891 -0.6017 0.7979 0.2786

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6340
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.683
_diffrn_reflns_theta_min         4.649
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -17.00   1.00    2.50    --  -41.40 -37.00 150.00   98
  2  ω      1.00  62.00   1.00    2.50    --   41.40 -99.00  30.00   61
  3  ω     19.00  72.00   1.00    2.50    --   41.40 -99.00-180.00   53
  4  ω    116.00 176.00   1.00   10.00    --  112.00  61.00 120.00   60
  5  ω     31.00 105.00   1.00   10.00    --  112.00 -94.00  60.00   74
  6  ω     40.00 104.00   1.00   10.00    --  112.00-111.00  30.00   64
  7  ω    108.00 169.00   1.00   10.00    --  112.00 111.00 150.00   61
  8  ω     52.00 141.00   1.00   10.00    --  112.00 -61.00  90.00   89
  9  ω     85.00 175.00   1.00   10.00    --  112.00  30.00 -90.00   90
;
_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      -0.1355132000
_diffrn_orient_matrix_UB_12      -0.0972464000
_diffrn_orient_matrix_UB_13      -0.0035554000
_diffrn_orient_matrix_UB_21      0.1093368000
_diffrn_orient_matrix_UB_22      -0.1116290000
_diffrn_orient_matrix_UB_23      0.0238582000
_diffrn_orient_matrix_UB_31      -0.0311755000
_diffrn_orient_matrix_UB_32      0.0298646000
_diffrn_orient_matrix_UB_33      0.0773777000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                2754
_reflns_number_total             3428
_reflns_odcompleteness_completeness 98.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43c (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.262
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.028
_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)+(0.0564P)²+0.3244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1178
_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:
 C2(H2), C4(H4), C5(H5), C6(H6), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
2.b Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.21349(16) 0.83145(15) 0.24347(7) 0.0229(3) Uani 1 1 d . . . . .
C2 C 0.10738(17) 0.81295(15) 0.18713(7) 0.0235(3) Uani 1 1 d . . . . .
H2 H 0.0792 0.7283 0.1737 0.028 Uiso 1 1 calc R . . . .
C3 C 0.04284(18) 0.91989(16) 0.15062(7) 0.0257(3) Uani 1 1 d . . . . .
C4 C 0.08904(19) 1.04563(16) 0.17137(8) 0.0287(3) Uani 1 1 d . . . . .
H4 H 0.0484 1.1179 0.1472 0.034 Uiso 1 1 calc R . . . .
C5 C 0.1944(2) 1.06466(16) 0.22731(8) 0.0303(3) Uani 1 1 d . . . . .
H5 H 0.2237 1.1492 0.2403 0.036 Uiso 1 1 calc R . . . .
C6 C 0.25627(18) 0.95788(15) 0.26398(8) 0.0264(3) Uani 1 1 d . . . . .
H6 H 0.3258 0.9707 0.3019 0.032 Uiso 1 1 calc R . . . .
C7 C 0.28117(16) 0.72014(15) 0.28567(7) 0.0228(3) Uani 1 1 d . . . . .
O8 O 0.31821(13) 0.73234(11) 0.34823(5) 0.0277(2) Uani 1 1 d . . . . .
N9 N 0.29796(15) 0.60591(12) 0.24905(6) 0.0238(3) Uani 1 1 d . . . . .
H9 H 0.271(2) 0.6110(19) 0.2042(10) 0.029 Uiso 1 1 d R . . . .
C10 C 0.35561(16) 0.48308(15) 0.27256(7) 0.0230(3) Uani 1 1 d . . . . .
N11 N 0.34755(15) 0.37994(12) 0.23389(6) 0.0242(3) Uani 1 1 d . . . . .
C12 C 0.25947(18) 0.37956(14) 0.16942(7) 0.0232(3) Uani 1 1 d . . . . .
C13 C 0.10505(18) 0.41594(15) 0.16454(7) 0.0248(3) Uani 1 1 d . . . . .
H13 H 0.0586 0.4475 0.2041 0.030 Uiso 1 1 calc R . . . .
C14 C 0.01947(19) 0.40558(16) 0.10112(8) 0.0288(3) Uani 1 1 d . . . . .
H14 H -0.0834 0.4305 0.0986 0.035 Uiso 1 1 calc R . . . .
C15 C 0.0873(2) 0.35816(17) 0.04156(8) 0.0302(3) Uani 1 1 d . . . . .
H15 H 0.0305 0.3517 -0.0009 0.036 Uiso 1 1 calc R . . . .
C16 C 0.2408(2) 0.32044(16) 0.04611(8) 0.0291(3) Uani 1 1 d . . . . .
H16 H 0.2867 0.2885 0.0065 0.035 Uiso 1 1 calc R . . . .
C17 C 0.32656(18) 0.33006(15) 0.10944(8) 0.0254(3) Uani 1 1 d . . . . .
H17 H 0.4288 0.3035 0.1120 0.031 Uiso 1 1 calc R . . . .
N18 N 0.42783(15) 0.48711(13) 0.33766(6) 0.0250(3) Uani 1 1 d . . . . .
H18 H 0.429(2) 0.567(2) 0.3558(10) 0.030 Uiso 1 1 d R . . . .
C19 C 0.49541(17) 0.38367(15) 0.37709(7) 0.0235(3) Uani 1 1 d . . . . .
C20 C 0.59558(19) 0.41828(17) 0.43357(8) 0.0292(3) Uani 1 1 d . . . . .
H20 H 0.6173 0.5062 0.4424 0.035 Uiso 1 1 calc R . . . .
C21 C 0.6628(2) 0.32264(19) 0.47652(8) 0.0342(4) Uani 1 1 d . . . . .
H21 H 0.7285 0.3470 0.5142 0.041 Uiso 1 1 calc R . . . .
C22 C 0.6331(2) 0.19099(18) 0.46396(8) 0.0334(4) Uani 1 1 d . . . . .
H22 H 0.6791 0.1269 0.4926 0.040 Uiso 1 1 calc R . . . .
C23 C 0.5337(2) 0.15665(17) 0.40811(8) 0.0307(3) Uani 1 1 d . . . . .
H23 H 0.5127 0.0686 0.3995 0.037 Uiso 1 1 calc R . . . .
C24 C 0.46467(19) 0.25137(16) 0.36459(8) 0.0287(3) Uani 1 1 d . . . . .
H24 H 0.3982 0.2265 0.3273 0.034 Uiso 1 1 calc R . . . .
C25 C -0.0714(2) 0.89961(18) 0.09007(8) 0.0332(4) Uani 1 1 d . . . . .
H25A H -0.0178 0.8894 0.0475 0.050 Uiso 1 1 calc GR . . . .
H25B H -0.1385 0.9741 0.0859 0.050 Uiso 1 1 calc GR . . . .
H25C H -0.1308 0.8223 0.0981 0.050 Uiso 1 1 calc GR . . . .


_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
C1 C2 1.396(2) . ?
C1 C6 1.394(2) . ?
C1 C7 1.496(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.398(2) . ?
C3 C4 1.396(2) . ?
C3 C25 1.501(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(2) . ?
C6 H6 0.9300 . ?
C7 O8 1.2259(18) . ?
C7 N9 1.3696(19) . ?
N9 H9 0.877(19) . ?
N9 C10 1.4151(19) . ?
C10 N11 1.285(2) . ?
C10 N18 1.3642(19) . ?
N11 C12 1.4169(18) . ?
C12 C13 1.394(2) . ?
C12 C17 1.401(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.393(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.390(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.392(2) . ?
C17 H17 0.9300 . ?
N18 H18 0.88(2) . ?
N18 C19 1.4082(19) . ?
C19 C20 1.398(2) . ?
C19 C24 1.395(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.387(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.384(2) . ?
C23 H23 0.9300 . ?
C23 C24 1.391(2) . ?
C24 H24 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C7 122.69(13) . . ?
C6 C1 C2 119.96(14) . . ?
C6 C1 C7 117.31(13) . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.87(14) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C25 120.72(14) . . ?
C4 C3 C2 118.22(14) . . ?
C4 C3 C25 121.05(14) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.18(14) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.23(15) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.52(14) . . ?
C5 C6 H6 120.2 . . ?
O8 C7 C1 121.59(13) . . ?
O8 C7 N9 123.49(14) . . ?
N9 C7 C1 114.92(12) . . ?
C7 N9 H9 114.6(13) . . ?
C7 N9 C10 129.60(12) . . ?
C10 N9 H9 115.8(13) . . ?
N11 C10 N9 122.36(13) . . ?
N11 C10 N18 123.80(14) . . ?
N18 C10 N9 113.73(13) . . ?
C10 N11 C12 120.79(13) . . ?
C13 C12 N11 122.57(13) . . ?
C13 C12 C17 118.65(13) . . ?
C17 C12 N11 118.55(14) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.85(14) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.23(15) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.31(14) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.64(14) . . ?
C17 C16 H16 119.7 . . ?
C12 C17 H17 119.8 . . ?
C16 C17 C12 120.31(14) . . ?
C16 C17 H17 119.8 . . ?
C10 N18 H18 112.3(13) . . ?
C10 N18 C19 128.71(13) . . ?
C19 N18 H18 119.0(13) . . ?
C20 C19 N18 116.81(14) . . ?
C24 C19 N18 124.23(14) . . ?
C24 C19 C20 118.93(14) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.49(16) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.69(16) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.6 . . ?
C23 C22 C21 118.85(15) . . ?
C23 C22 H22 120.6 . . ?
C22 C23 H23 119.4 . . ?
C22 C23 C24 121.26(16) . . ?
C24 C23 H23 119.4 . . ?
C19 C24 H24 120.1 . . ?
C23 C24 C19 119.78(15) . . ?
C23 C24 H24 120.1 . . ?
C3 C25 H25A 109.5 . . ?
C3 C25 H25B 109.5 . . ?
C3 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?


_ins_header                      
;
TITL OHD113-2-CD068_auto in P2(1)/c 
REM P2(1)/c (#14 in standard setting)
CELL 1.54184   8.708372  10.204010  19.044763  90.0000  92.6911  90.0000
ZERR    4.00   0.000346   0.000464   0.000668   0.0000   0.0036   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2 
SFAC C H N O
UNIT 84.00 76.00 12.00 4.00
TREF
HKLF 4
END
;
_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 1.282
_oxdiff_exptl_absorpt_empirical_full_min 0.799
