# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_hpd289
_database_code_depnum_ccdc_archive 'CCDC 2340499'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman '
;The University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2024-03-14 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2021-02-02
_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        ?
_chemical_formula_moiety         'C18 H21 N O'
_chemical_formula_sum            'C18 H21 N O'
_chemical_formula_weight         267.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     129-7
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.75307(9)
_cell_length_b                   16.23315(13)
_cell_length_c                   18.76027(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2970.18(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11784
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.8720
_cell_measurement_theta_min      3.5980
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.889
_exptl_absorpt_coefficient_mu    0.568
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.547
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.196
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             1152
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 10 1 0.0787
-5 3 -5 0.0243
-1 -10 -2 0.1214
6 -1 5 0.0304
2 10 -1 0.0964
2 -2 -11 0.0432
-3 -9 4 0.0965
-2 3 11 0.0278

_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.074
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
-0.2262 10.4873 1.0179 -0.3175 0.0108 0.9482
-5.4644 3.3020 -4.8516 -0.9996 0.0267 -0.0090
-0.5902 -10.3696 -1.7870 0.1781 -0.0071 -0.9840
5.6542 -1.4111 5.2563 0.9808 -0.0258 0.1931
2.4082 9.7066 -0.8720 0.0107 0.3187 0.9478
2.1798 -2.1648 -11.1537 0.0247 0.9499 -0.3117
-2.9457 -8.5884 4.1755 -0.0176 -0.5882 -0.8085
-2.0948 2.5035 11.1193 -0.0243 -0.9384 0.3447

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18036
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.115
_diffrn_reflns_theta_min         4.714
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -164.00 -74.00   0.50    0.34    --  -88.50 -26.00 -99.00  180
  2  ω    -82.00 -15.00   0.50    0.34    --  -88.50 109.00 160.00  134
  3  ω    105.00 178.00   0.50    0.34    --  106.69 106.00-104.00  146
  4  ω    -34.00  29.00   0.50    0.09    --  -46.75  26.00  64.00  126
  5  ω   -119.00 -88.00   0.50    0.09    --  -46.75-125.00-180.00   62
  6  ω   -119.00 -88.00   0.50    0.09    --  -46.75-125.00  30.00   62
  7  ω   -119.00 -83.00   0.50    0.09    --  -46.75 -57.00 -30.00   72
  8  ω    -30.00  29.00   0.50    0.09    --  -46.75  19.00-150.00  118
  9  ω    -51.00 -16.00   0.50    0.34    --  -88.50  45.00 -60.00   70
 10  ω    -51.00 -16.00   0.50    0.34    --  -88.50  45.00  60.00   70
 11  ω     34.00  71.00   0.50    0.34    --  106.69 -61.00   0.00   74
 12  ω     34.00 111.00   0.50    0.34    --  106.69-125.00 150.00  154
 13  ω     34.00  71.00   0.50    0.34    --  106.69 -61.00  30.00   74
 14  ω     34.00 105.00   0.50    0.34    --  106.69 -94.00  90.00  142
 15  ω     34.00  71.00   0.50    0.34    --  106.69 -61.00  60.00   74
 16  ω     34.00  71.00   0.50    0.34    --  106.69 -61.00 -30.00   74
 17  ω   -119.00 -94.00   0.50    0.09    --  -46.75 -57.00  60.00   50
 18  ω   -121.00 -32.00   0.50    0.09    --  -46.75 -37.00  90.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1375237000
_diffrn_orient_matrix_UB_12      -0.0302686000
_diffrn_orient_matrix_UB_13      0.0305408000
_diffrn_orient_matrix_UB_21      0.0666532000
_diffrn_orient_matrix_UB_22      0.0096482000
_diffrn_orient_matrix_UB_23      -0.0740077000
_diffrn_orient_matrix_UB_31      0.0394839000
_diffrn_orient_matrix_UB_32      0.0894914000
_diffrn_orient_matrix_UB_33      0.0182925000
_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                2725
_reflns_number_total             3000
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_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         0.307
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.00061(9)
_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   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3000
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0464P)²+1.0061P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0928
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C3(H3A,H3B), C5(H5A,H5B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C8(H8), C12(H12), C10(H10), C18(H18), C14(H14), C11(H11), C17(H17),
 C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.57436(9) 0.54742(4) 0.40781(4) 0.0281(2) Uani 1 1 d . . . . .
N1 N 0.50570(9) 0.28889(5) 0.51402(4) 0.0194(2) Uani 1 1 d . . . . .
C7 C 0.49973(10) 0.22540(6) 0.39408(5) 0.0166(2) Uani 1 1 d . . . . .
C13 C 0.50885(10) 0.22541(6) 0.56317(5) 0.0178(2) Uani 1 1 d . . . . .
C2 C 0.59090(10) 0.36875(6) 0.41124(5) 0.0179(2) Uani 1 1 d . . . . .
H2 H 0.632274 0.359949 0.363067 0.021 Uiso 1 1 calc R U . . .
C1 C 0.57404(10) 0.28290(6) 0.44542(5) 0.0169(2) Uani 1 1 d . . . . .
H1A H 0.667778 0.259893 0.453793 0.020 Uiso 1 1 calc R U . . .
C9 C 0.50975(11) 0.13166(6) 0.29404(6) 0.0220(2) Uani 1 1 d . . . . .
H9 H 0.562442 0.101586 0.260322 0.026 Uiso 1 1 calc R U . . .
C8 C 0.57504(10) 0.18163(6) 0.34367(5) 0.0195(2) Uani 1 1 d . . . . .
H8 H 0.672172 0.185975 0.343204 0.023 Uiso 1 1 calc R U . . .
C12 C 0.35756(11) 0.21821(6) 0.39382(6) 0.0212(2) Uani 1 1 d . . . . .
H12 H 0.304812 0.246949 0.428374 0.025 Uiso 1 1 calc R U . . .
C10 C 0.36785(11) 0.12555(6) 0.29354(6) 0.0223(2) Uani 1 1 d . . . . .
H10 H 0.322989 0.091748 0.259412 0.027 Uiso 1 1 calc R U . . .
C6 C 0.45561(11) 0.41458(6) 0.39971(6) 0.0210(2) Uani 1 1 d . . . . .
H6A H 0.395321 0.381875 0.368066 0.025 Uiso 1 1 calc R U . . .
H6B H 0.408223 0.421793 0.445956 0.025 Uiso 1 1 calc R U . . .
C18 C 0.56087(11) 0.14709(6) 0.54678(6) 0.0215(2) Uani 1 1 d . . . . .
H18 H 0.595917 0.136272 0.500465 0.026 Uiso 1 1 calc R U . . .
C14 C 0.45742(11) 0.23914(7) 0.63212(6) 0.0217(2) Uani 1 1 d . . . . .
H14 H 0.421557 0.291716 0.644237 0.026 Uiso 1 1 calc R U . . .
C11 C 0.29213(11) 0.16933(6) 0.34344(6) 0.0242(2) Uani 1 1 d . . . . .
H11 H 0.194900 0.165843 0.343131 0.029 Uiso 1 1 calc R U . . .
C3 C 0.68981(11) 0.42403(6) 0.45280(6) 0.0224(2) Uani 1 1 d . . . . .
H3A H 0.654882 0.432364 0.501816 0.027 Uiso 1 1 calc R U . . .
H3B H 0.780675 0.397100 0.456016 0.027 Uiso 1 1 calc R U . . .
C17 C 0.56132(12) 0.08521(7) 0.59807(6) 0.0275(3) Uani 1 1 d . . . . .
H17 H 0.597070 0.032459 0.586434 0.033 Uiso 1 1 calc R U . . .
C5 C 0.48269(13) 0.49838(7) 0.36634(6) 0.0266(3) Uani 1 1 d . . . . .
H5A H 0.522027 0.490472 0.318177 0.032 Uiso 1 1 calc R U . . .
H5B H 0.394648 0.528086 0.360965 0.032 Uiso 1 1 calc R U . . .
C4 C 0.70409(13) 0.50682(7) 0.41567(6) 0.0286(3) Uani 1 1 d . . . . .
H4A H 0.766596 0.542395 0.443614 0.034 Uiso 1 1 calc R U . . .
H4B H 0.745411 0.498434 0.368016 0.034 Uiso 1 1 calc R U . . .
C15 C 0.45841(13) 0.17697(7) 0.68258(6) 0.0294(3) Uani 1 1 d . . . . .
H15 H 0.423373 0.187271 0.728982 0.035 Uiso 1 1 calc R U . . .
C16 C 0.51034(14) 0.09946(7) 0.66590(7) 0.0328(3) Uani 1 1 d . . . . .
H16 H 0.510827 0.056838 0.700598 0.039 Uiso 1 1 calc R U . . .
H1 H 0.4891(16) 0.3386(10) 0.5307(8) 0.039 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.4277(14) . ?
O1 C4 1.4343(15) . ?
N1 C13 1.3832(13) . ?
N1 C1 1.4526(13) . ?
N1 H1 0.881(16) . ?
C7 C1 1.5244(13) . ?
C7 C8 1.3925(14) . ?
C7 C12 1.3915(14) . ?
C13 C18 1.4031(14) . ?
C13 C14 1.4051(15) . ?
C2 H2 1.0000 . ?
C2 C1 1.5427(13) . ?
C2 C6 1.5302(14) . ?
C2 C3 1.5309(14) . ?
C1 H1A 1.0000 . ?
C9 H9 0.9500 . ?
C9 C8 1.3893(14) . ?
C9 C10 1.3876(15) . ?
C8 H8 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.3894(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3880(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.5205(14) . ?
C18 H18 0.9500 . ?
C18 C17 1.3910(15) . ?
C14 H14 0.9500 . ?
C14 C15 1.3837(15) . ?
C11 H11 0.9500 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5201(15) . ?
C17 H17 0.9500 . ?
C17 C16 1.3856(18) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C15 H15 0.9500 . ?
C15 C16 1.3920(18) . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O1 C4 110.62(8) . . ?
C13 N1 C1 122.05(8) . . ?
C13 N1 H1 116.7(10) . . ?
C1 N1 H1 117.4(10) . . ?
C8 C7 C1 119.39(9) . . ?
C12 C7 C1 121.83(9) . . ?
C12 C7 C8 118.71(9) . . ?
N1 C13 C18 122.48(9) . . ?
N1 C13 C14 119.19(9) . . ?
C18 C13 C14 118.33(9) . . ?
C1 C2 H2 106.8 . . ?
C6 C2 H2 106.8 . . ?
C6 C2 C1 113.96(8) . . ?
C6 C2 C3 109.29(8) . . ?
C3 C2 H2 106.8 . . ?
C3 C2 C1 112.64(8) . . ?
N1 C1 C7 112.49(8) . . ?
N1 C1 C2 110.89(8) . . ?
N1 C1 H1A 107.8 . . ?
C7 C1 C2 109.95(8) . . ?
C7 C1 H1A 107.8 . . ?
C2 C1 H1A 107.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C10 C9 C8 120.22(9) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.75(10) . . ?
C9 C8 H8 119.6 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.53(9) . . ?
C11 C12 H12 119.7 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.31(9) . . ?
C11 C10 H10 120.3 . . ?
C2 C6 H6A 109.6 . . ?
C2 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?
C5 C6 C2 110.09(9) . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.26(10) . . ?
C17 C18 H18 119.9 . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.77(10) . . ?
C15 C14 H14 119.6 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.45(10) . . ?
C10 C11 H11 119.8 . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 C2 110.04(9) . . ?
C4 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C18 C17 H17 119.5 . . ?
C16 C17 C18 120.91(11) . . ?
C16 C17 H17 119.5 . . ?
O1 C5 C6 112.54(9) . . ?
O1 C5 H5A 109.1 . . ?
O1 C5 H5B 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
O1 C4 C3 111.87(9) . . ?
O1 C4 H4A 109.2 . . ?
O1 C4 H4B 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.53(11) . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 119.20(10) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C13 C18 C17 -179.79(10) . . . . ?
N1 C13 C14 C15 179.74(10) . . . . ?
C7 C12 C11 C10 1.38(16) . . . . ?
C13 N1 C1 C7 73.12(12) . . . . ?
C13 N1 C1 C2 -163.29(9) . . . . ?
C13 C18 C17 C16 0.21(17) . . . . ?
C13 C14 C15 C16 -0.08(17) . . . . ?
C2 C6 C5 O1 -56.60(12) . . . . ?
C2 C3 C4 O1 57.65(11) . . . . ?
C1 N1 C13 C18 -9.24(15) . . . . ?
C1 N1 C13 C14 171.19(9) . . . . ?
C1 C7 C8 C9 -177.03(9) . . . . ?
C1 C7 C12 C11 175.87(9) . . . . ?
C1 C2 C6 C5 179.67(8) . . . . ?
C1 C2 C3 C4 178.87(8) . . . . ?
C9 C10 C11 C12 -0.59(16) . . . . ?
C8 C7 C1 N1 -149.03(9) . . . . ?
C8 C7 C1 C2 86.85(11) . . . . ?
C8 C7 C12 C11 -1.05(15) . . . . ?
C8 C9 C10 C11 -0.49(16) . . . . ?
C12 C7 C1 N1 34.07(13) . . . . ?
C12 C7 C1 C2 -90.04(11) . . . . ?
C12 C7 C8 C9 -0.03(15) . . . . ?
C10 C9 C8 C7 0.80(15) . . . . ?
C6 C2 C1 N1 -58.37(11) . . . . ?
C6 C2 C1 C7 66.67(10) . . . . ?
C6 C2 C3 C4 -53.38(11) . . . . ?
C18 C13 C14 C15 0.15(15) . . . . ?
C18 C17 C16 C15 -0.14(18) . . . . ?
C14 C13 C18 C17 -0.21(15) . . . . ?
C14 C15 C16 C17 0.08(19) . . . . ?
C3 C2 C1 N1 66.88(11) . . . . ?
C3 C2 C1 C7 -168.08(8) . . . . ?
C3 C2 C6 C5 52.66(11) . . . . ?
C5 O1 C4 C3 -60.19(11) . . . . ?
C4 O1 C5 C6 59.78(12) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.868
####################################################################### 
# 
# 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_hpd291
_database_code_depnum_ccdc_archive 'CCDC 2340500'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman '
;The University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2024-03-14 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2021-02-02
_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        ?
_chemical_formula_moiety         'C20 H25 N'
_chemical_formula_sum            'C20 H25 N'
_chemical_formula_weight         279.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     'Sample 123-4'
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'

_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                   5.64642(5)
_cell_length_b                   20.42415(18)
_cell_length_c                   13.59672(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.2646(7)
_cell_angle_gamma                90
_cell_volume                     1566.79(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20513
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3620
_cell_measurement_theta_min      3.8730
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.884
_exptl_absorpt_coefficient_mu    0.507
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.465
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.63a (Rigaku Oxford Diffraction, 2019)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             608
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 1 -4 0.0576
-1 11 -5 0.0193
0 -11 5 0.0160
0 -13 2 0.0234
-4 -2 2 0.0441
0 13 -2 0.0176

_exptl_crystal_size_max          0.249
_exptl_crystal_size_mid          0.122
_exptl_crystal_size_min          0.043
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
3.3481 0.8069 -3.8651 -0.4888 -0.3332 0.8062
-0.6230 10.8343 -4.8006 -0.7164 -0.4932 -0.4935
0.1071 -10.6473 5.2397 0.7688 0.5288 0.3595
0.2366 -12.8471 2.0844 0.4623 0.7513 0.4710
-3.5573 -2.1096 1.9343 0.3048 0.5005 -0.8103
-0.4507 12.8023 -1.9820 -0.4470 -0.7261 -0.5224

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35340
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.664
_diffrn_reflns_theta_min         3.908
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_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 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00  26.00   0.50    0.17    --  -46.75  88.00 -47.00  202
  2  ω    -21.00  76.00   0.50    0.17    --   46.75 -88.00-164.00  194
  3  ω   -117.00 -15.00   0.50    0.66    --  -88.50  88.00 -47.00  204
  4  ω   -160.00 -79.00   0.50    0.66    --  -88.50 -88.00-164.00  162
  5  ω    101.00 178.00   0.50    0.66    --  106.69  88.00 -47.00  154
  6  ω     34.00 135.00   0.50    0.66    --  106.69 -88.00-164.00  202
  7  ω   -121.00 -32.00   0.50    0.17    --  -46.75 -37.00  60.00  178
  8  ω   -119.00 -83.00   0.50    0.17    --  -46.75 -57.00   0.00   72
  9  ω    -70.00  26.00   0.50    0.17    --  -46.75  77.00  60.00  192
 10  ω   -119.00 -83.00   0.50    0.17    --  -46.75 -57.00 -90.00   72
 11  ω   -119.00 -83.00   0.50    0.17    --  -46.75 -57.00 -60.00   72
 12  ω     83.00 119.00   0.50    0.17    --   46.75  57.00 -30.00   72
 13  ω     83.00 119.00   0.50    0.17    --   46.75  57.00 -60.00   72
 14  ω    -29.00  30.00   0.50    0.17    --   46.75 -19.00-180.00  118
 15  ω    -51.00 -16.00   0.50    0.66    --  -88.50  45.00  30.00   70
 16  ω   -160.00-100.00   0.50    0.66    --  -88.50 -94.00-150.00  120
 17  ω   -160.00-100.00   0.50    0.66    --  -88.50 -94.00 150.00  120
 18  ω    -51.00 -16.00   0.50    0.66    --  -88.50  45.00-120.00   70
 19  ω   -160.00-101.00   0.50    0.66    --  -88.50 -77.00-150.00  118
 20  ω    -51.00 -16.00   0.50    0.66    --  -88.50  45.00 150.00   70
 21  ω    -71.00 -15.00   0.50    0.66    --  -88.50  61.00-120.00  112
 22  ω    -51.00 -16.00   0.50    0.66    --  -88.50  45.00 -30.00   70
 23  ω    -51.00 -16.00   0.50    0.66    --  -88.50  45.00  90.00   70
 24  ω   -163.00 -73.00   0.50    0.66    --  -88.50 -30.00  30.00  180
 25  ω     34.00  71.00   0.50    0.66    --  106.69 -61.00-150.00   74
 26  ω     34.00 105.00   0.50    0.66    --  106.69 -94.00 -90.00  142
 27  ω     34.00 101.00   0.50    0.66    --  106.69 -77.00  90.00  134
 28  ω     92.00 178.00   0.50    0.66    --  106.69  45.00   0.00  172
 29  ω     91.00 178.00   0.50    0.66    --  106.69  30.00 -90.00  174
 30  ω     92.00 178.00   0.50    0.66    --  106.69  45.00 -90.00  172
 31  ω     91.00 178.00   0.50    0.66    --  106.69  30.00  60.00  174
 32  ω     91.00 178.00   0.50    0.66    --  106.69  30.00  90.00  174
 33  ω     34.00 101.00   0.50    0.66    --  106.69 -77.00 -30.00  134
 34  ω     34.00 101.00   0.50    0.66    --  106.69 -77.00 150.00  134
 35  ω     34.00 105.00   0.50    0.66    --  106.69 -94.00 150.00  142
 36  ω     34.00 105.00   0.50    0.66    --  106.69 -94.00 120.00  142
 37  ω     34.00 105.00   0.50    0.66    --  106.69 -94.00 -60.00  142
 38  ω     34.00  71.00   0.50    0.66    --  106.69 -61.00  30.00   74
 39  ω   -121.00 -32.00   0.50    0.17    --  -46.75 -37.00 150.00  178
 40  ω     32.00 121.00   0.50    0.17    --   46.75  37.00-150.00  178
 41  ω     32.00 121.00   0.50    0.17    --   46.75  37.00 150.00  178
 42  ω     32.00 121.00   0.50    0.17    --   46.75  37.00  90.00  178
 43  ω     32.00 121.00   0.50    0.17    --   46.75  37.00 -30.00  178
 44  ω     32.00 121.00   0.50    0.17    --   46.75  37.00-120.00  178
 45  ω     32.00 121.00   0.50    0.17    --   46.75  37.00 -60.00  178
 46  ω     32.00 121.00   0.50    0.17    --   46.75  37.00  30.00  178
 47  ω     91.00 130.00   0.50    0.66    --  106.69  30.00 -30.00   78
 48  ω     91.00 178.00   0.50    0.66    --  106.69  30.00-150.00  174
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0152136000
_diffrn_orient_matrix_UB_12      -0.0185065000
_diffrn_orient_matrix_UB_13      0.1094334000
_diffrn_orient_matrix_UB_21      -0.1180164000
_diffrn_orient_matrix_UB_22      -0.0654718000
_diffrn_orient_matrix_UB_23      -0.0296982000
_diffrn_orient_matrix_UB_31      0.2456949000
_diffrn_orient_matrix_UB_32      -0.0325554000
_diffrn_orient_matrix_UB_33      -0.0025631000
_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                3003
_reflns_number_total             3256
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.63a (Rigaku OD, 2019)'
_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         0.321
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.0017(3)
_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   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.7000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0995
_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 Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C12(H12), C9(H9), C15(H15), C20(H20), C14(H14), C18(H18), C10(H10),
 C17(H17), C11(H11)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.58218(16) 0.28020(4) 0.56498(7) 0.0165(2) Uani 1 1 d . . . . .
H1 H 0.447396 0.291146 0.534644 0.020 Uiso 1 1 calc R U . . .
C13 C 0.73864(18) 0.32991(5) 0.59159(7) 0.0144(2) Uani 1 1 d . . . . .
C8 C 0.64554(18) 0.19440(5) 0.69328(8) 0.0148(2) Uani 1 1 d . . . . .
C12 C 0.82616(19) 0.15388(5) 0.73046(8) 0.0170(2) Uani 1 1 d . . . . .
H12 H 0.950018 0.141126 0.689213 0.020 Uiso 1 1 calc R U . . .
C1 C 0.62592(18) 0.21117(5) 0.58385(8) 0.0147(2) Uani 1 1 d . . . . .
H1A H 0.778290 0.198885 0.553613 0.018 Uiso 1 1 calc R U . . .
C9 C 0.4694(2) 0.19211(5) 0.85282(8) 0.0183(2) Uani 1 1 d . . . . .
H9 H 0.347539 0.205561 0.894609 0.022 Uiso 1 1 calc R U . . .
C15 C 1.10800(19) 0.37008(5) 0.66596(8) 0.0170(2) Uani 1 1 d . . . . .
H15 H 1.256540 0.360881 0.698251 0.020 Uiso 1 1 calc R U . . .
C20 C 0.47024(19) 0.21446(5) 0.75632(8) 0.0164(2) Uani 1 1 d . . . . .
H20 H 0.350057 0.243748 0.732936 0.020 Uiso 1 1 calc R U . . .
C16 C 1.04493(19) 0.43497(5) 0.64795(8) 0.0171(2) Uani 1 1 d . . . . .
C14 C 0.95972(19) 0.31816(5) 0.63803(8) 0.0161(2) Uani 1 1 d . . . . .
H14 H 1.009444 0.274421 0.650682 0.019 Uiso 1 1 calc R U . . .
C2 C 0.42344(18) 0.17115(5) 0.53247(8) 0.0150(2) Uani 1 1 d . . . . .
H2 H 0.270129 0.189224 0.554963 0.018 Uiso 1 1 calc R U . . .
C18 C 0.67554(19) 0.39530(5) 0.57167(8) 0.0168(2) Uani 1 1 d . . . . .
H18 H 0.527719 0.404709 0.538924 0.020 Uiso 1 1 calc R U . . .
C10 C 0.6469(2) 0.15001(5) 0.88833(8) 0.0184(2) Uani 1 1 d . . . . .
H10 H 0.644455 0.133841 0.953791 0.022 Uiso 1 1 calc R U . . .
C17 C 0.8262(2) 0.44620(5) 0.59921(8) 0.0189(2) Uani 1 1 d . . . . .
H17 H 0.779579 0.489921 0.584551 0.023 Uiso 1 1 calc R U . . .
C7 C 0.4334(2) 0.09871(5) 0.56186(8) 0.0184(2) Uani 1 1 d . . . . .
H7A H 0.587424 0.080097 0.543543 0.022 Uiso 1 1 calc R U . . .
H7B H 0.423207 0.095064 0.634179 0.022 Uiso 1 1 calc R U . . .
C3 C 0.4207(2) 0.17734(6) 0.41964(8) 0.0178(2) Uani 1 1 d . . . . .
H3A H 0.404731 0.224031 0.400975 0.021 Uiso 1 1 calc R U . . .
H3B H 0.572648 0.161039 0.395221 0.021 Uiso 1 1 calc R U . . .
C11 C 0.8273(2) 0.13182(5) 0.82755(8) 0.0190(2) Uani 1 1 d . . . . .
H11 H 0.951693 0.104298 0.852096 0.023 Uiso 1 1 calc R U . . .
C4 C 0.2156(2) 0.13830(6) 0.37140(8) 0.0197(2) Uani 1 1 d . . . . .
H4A H 0.063123 0.156792 0.391909 0.024 Uiso 1 1 calc R U . . .
H4B H 0.220712 0.142289 0.298949 0.024 Uiso 1 1 calc R U . . .
C6 C 0.2325(2) 0.05901(5) 0.51207(8) 0.0203(2) Uani 1 1 d . . . . .
H6A H 0.252073 0.012241 0.529715 0.024 Uiso 1 1 calc R U . . .
H6B H 0.078957 0.074030 0.536629 0.024 Uiso 1 1 calc R U . . .
C5 C 0.2293(2) 0.06614(6) 0.40024(8) 0.0216(3) Uani 1 1 d . . . . .
H5A H 0.374672 0.046477 0.374531 0.026 Uiso 1 1 calc R U . . .
H5B H 0.090893 0.042504 0.370707 0.026 Uiso 1 1 calc R U . . .
C19 C 1.2017(2) 0.49132(6) 0.68058(9) 0.0239(3) Uani 1 1 d . . . . .
H19A H 1.130488 0.514135 0.735505 0.036 Uiso 1 1 calc R U . . .
H19B H 1.218312 0.521804 0.625625 0.036 Uiso 1 1 calc R U . . .
H19C H 1.358228 0.474627 0.701816 0.036 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
N1 H1 0.8800 . ?
N1 C13 1.3845(14) . ?
N1 C1 1.4525(13) . ?
C13 C14 1.3973(15) . ?
C13 C18 1.4058(15) . ?
C8 C12 1.3927(15) . ?
C8 C1 1.5267(14) . ?
C8 C20 1.3961(15) . ?
C12 H12 0.9500 . ?
C12 C11 1.3946(15) . ?
C1 H1A 1.0000 . ?
C1 C2 1.5492(14) . ?
C9 H9 0.9500 . ?
C9 C20 1.3894(15) . ?
C9 C10 1.3922(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.3914(15) . ?
C15 C14 1.3946(15) . ?
C20 H20 0.9500 . ?
C16 C17 1.3971(16) . ?
C16 C19 1.5080(15) . ?
C14 H14 0.9500 . ?
C2 H2 1.0000 . ?
C2 C7 1.5331(14) . ?
C2 C3 1.5387(14) . ?
C18 H18 0.9500 . ?
C18 C17 1.3855(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3875(16) . ?
C17 H17 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.5303(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5321(15) . ?
C11 H11 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5263(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.5269(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C13 N1 H1 117.9 . . ?
C13 N1 C1 124.29(9) . . ?
C1 N1 H1 117.9 . . ?
N1 C13 C14 122.79(10) . . ?
N1 C13 C18 119.48(10) . . ?
C14 C13 C18 117.73(10) . . ?
C12 C8 C1 120.72(9) . . ?
C12 C8 C20 118.57(10) . . ?
C20 C8 C1 120.44(9) . . ?
C8 C12 H12 119.6 . . ?
C8 C12 C11 120.75(10) . . ?
C11 C12 H12 119.6 . . ?
N1 C1 C8 113.28(9) . . ?
N1 C1 H1A 108.3 . . ?
N1 C1 C2 108.37(8) . . ?
C8 C1 H1A 108.3 . . ?
C8 C1 C2 110.18(8) . . ?
C2 C1 H1A 108.3 . . ?
C20 C9 H9 120.0 . . ?
C20 C9 C10 120.07(10) . . ?
C10 C9 H9 120.0 . . ?
C16 C15 H15 119.0 . . ?
C16 C15 C14 121.98(10) . . ?
C14 C15 H15 119.0 . . ?
C8 C20 H20 119.6 . . ?
C9 C20 C8 120.82(10) . . ?
C9 C20 H20 119.6 . . ?
C15 C16 C17 117.07(10) . . ?
C15 C16 C19 122.13(10) . . ?
C17 C16 C19 120.79(10) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.56(10) . . ?
C15 C14 H14 119.7 . . ?
C1 C2 H2 107.4 . . ?
C7 C2 C1 111.89(9) . . ?
C7 C2 H2 107.4 . . ?
C7 C2 C3 109.75(9) . . ?
C3 C2 C1 112.61(8) . . ?
C3 C2 H2 107.4 . . ?
C13 C18 H18 119.6 . . ?
C17 C18 C13 120.83(10) . . ?
C17 C18 H18 119.6 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.61(10) . . ?
C11 C10 H10 120.2 . . ?
C16 C17 H17 119.1 . . ?
C18 C17 C16 121.79(10) . . ?
C18 C17 H17 119.1 . . ?
C2 C7 H7A 109.2 . . ?
C2 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
C6 C7 C2 112.16(9) . . ?
C6 C7 H7A 109.2 . . ?
C6 C7 H7B 109.2 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.22(9) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 C12 120.09(10) . . ?
C10 C11 H11 120.0 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 C3 111.26(9) . . ?
C5 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C5 C6 C7 111.68(9) . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C4 C5 C6 110.27(9) . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
N1 C13 C14 C15 -178.09(9) . . . . ?
N1 C13 C18 C17 178.67(10) . . . . ?
N1 C1 C2 C7 -170.93(8) . . . . ?
N1 C1 C2 C3 64.88(11) . . . . ?
C13 N1 C1 C8 63.91(13) . . . . ?
C13 N1 C1 C2 -173.51(9) . . . . ?
C13 C18 C17 C16 -0.32(17) . . . . ?
C8 C12 C11 C10 0.18(17) . . . . ?
C8 C1 C2 C7 -46.49(11) . . . . ?
C8 C1 C2 C3 -170.67(9) . . . . ?
C12 C8 C1 N1 -134.76(10) . . . . ?
C12 C8 C1 C2 103.67(11) . . . . ?
C12 C8 C20 C9 -2.96(16) . . . . ?
C1 N1 C13 C14 1.47(16) . . . . ?
C1 N1 C13 C18 -178.51(9) . . . . ?
C1 C8 C12 C11 -171.82(10) . . . . ?
C1 C8 C20 C9 171.22(10) . . . . ?
C1 C2 C7 C6 179.49(9) . . . . ?
C1 C2 C3 C4 -178.88(9) . . . . ?
C9 C10 C11 C12 -2.12(17) . . . . ?
C15 C16 C17 C18 1.36(16) . . . . ?
C20 C8 C12 C11 2.34(16) . . . . ?
C20 C8 C1 N1 51.19(13) . . . . ?
C20 C8 C1 C2 -70.38(12) . . . . ?
C20 C9 C10 C11 1.52(16) . . . . ?
C16 C15 C14 C13 -0.87(16) . . . . ?
C14 C13 C18 C17 -1.31(15) . . . . ?
C14 C15 C16 C17 -0.77(16) . . . . ?
C14 C15 C16 C19 178.24(10) . . . . ?
C2 C7 C6 C5 55.30(12) . . . . ?
C2 C3 C4 C5 -57.63(12) . . . . ?
C18 C13 C14 C15 1.89(15) . . . . ?
C10 C9 C20 C8 1.05(16) . . . . ?
C7 C2 C3 C4 55.76(12) . . . . ?
C7 C6 C5 C4 -55.26(13) . . . . ?
C3 C2 C7 C6 -54.74(12) . . . . ?
C3 C4 C5 C6 56.59(12) . . . . ?
C19 C16 C17 C18 -177.66(10) . . . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.379
_oxdiff_exptl_absorpt_empirical_full_min 0.770
####################################################################### 
# 
# 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_hpd800_auto
_database_code_depnum_ccdc_archive 'CCDC 2340502'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman '
;The University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2024-03-14 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2023-11-01
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H12 O2, C18 H22 N2'
_chemical_formula_sum            'C25 H34 N2 O2'
_chemical_formula_weight         394.54
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     'sample 4'
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                   9.2584(2)
_cell_length_b                   9.9261(2)
_cell_length_c                   11.8278(3)
_cell_angle_alpha                93.448(2)
_cell_angle_beta                 90.414(2)
_cell_angle_gamma                96.639(2)
_cell_volume                     1077.62(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10436
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3830
_cell_measurement_theta_min      3.7360
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.667
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             428
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -1 7 0.0511
-1 6 1 0.0511
2 1 -7 0.0545
1 -6 -1 0.0736
0 1 7 0.0462
6 -1 0 0.0177
0 -1 -7 0.0450
-6 1 0 0.0504

_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.071
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
-1.8696 -0.9063 7.2551 -0.0902 -0.3840 0.9189
-0.6239 6.3673 0.7119 0.2158 0.8932 0.3945
1.8862 0.7300 -7.2720 0.0842 0.3592 -0.9294
0.7358 -6.3009 -1.1493 -0.2099 -0.8684 -0.4493
0.2800 1.4033 7.3499 0.3620 -0.0892 0.9279
6.0076 -0.9039 0.0368 0.9197 -0.2205 -0.3248
0.1857 -1.4748 -7.3542 -0.2910 0.0721 -0.9540
-5.9956 0.8171 -0.4688 -0.9366 0.2247 0.2687

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20191
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.849
_diffrn_reflns_theta_min         3.744
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00 119.00   0.50    0.05    --   46.64  55.00-161.62  176
  2  ω     31.00 119.00   0.50    0.05    --   46.64  54.00-111.67  176
  3  ω     31.00 119.00   0.50    0.05    --   46.64  53.00 -38.00  176
  4  ω     32.00 121.00   0.50    0.05    --   46.64  31.00-148.00  178
  5  ω     33.00 119.00   0.50    0.05    --   46.64  44.00  50.50  172
  6  ω     31.00 119.00   0.50    0.05    --   46.64  53.00 103.67  176
  7  ω     31.00 119.00   0.50    0.05    --   46.64  53.00 148.93  176
  8  ω     34.00 101.00   0.50    0.15    --  106.92 -77.00  90.00  134
  9  ω     34.00  71.00   0.50    0.15    --  106.92 -61.00  90.00   74
 10  ω     34.00  71.00   0.50    0.15    --  106.92 -61.00   0.00   74
 11  ω     34.00  71.00   0.50    0.15    --  106.92 -61.00-150.00   74
 12  ω     34.00  71.00   0.50    0.15    --  106.92 -61.00-180.00   74
 13  ω     34.00  93.00   0.50    0.05    --   46.64-125.00 -90.00  118
 14  ω     37.00 112.00   0.50    0.15    --  106.92-125.00-180.00  150
 15  ω     37.00 112.00   0.50    0.15    --  106.92-125.00-150.00  150
 16  ω     37.00 112.00   0.50    0.15    --  106.92-125.00-120.00  150
 17  ω     37.00 112.00   0.50    0.15    --  106.92-125.00 -60.00  150
 18  ω     34.00 106.00   0.50    0.15    --  106.92 -94.00 -60.00  144
 19  ω     34.00 106.00   0.50    0.15    --  106.92 -94.00   0.00  144
 20  ω     37.00 112.00   0.50    0.15    --  106.92-125.00  90.00  150
 21  ω    -25.00  63.00   0.50    0.05    --   46.64 -57.00  30.00  176
 22  ω    -28.00  38.00   0.50    0.05    --   46.64 -31.00  51.00  132
 23  ω     92.00 178.00   0.50    0.15    --  106.92  31.00-148.00  172
 24  ω   -121.00 -31.00   0.50    0.05    --  -46.64 -31.00  51.00  180
 25  ω   -118.00 -83.00   0.50    0.05    --  -46.64 -57.00  60.00   70
 26  ω   -118.00 -31.00   0.50    0.05    --  -46.64 -52.00 -25.24  174
 27  ω    -85.00 -22.00   0.50    0.15    --  -91.75 125.00 -90.00  126
 28  ω   -101.00 -19.00   0.50    0.15    --  -91.75  77.00 -60.00  164
 29  ω    -71.00 -19.00   0.50    0.15    --  -91.75  61.00-120.00  104
 30  ω    -71.00 -19.00   0.50    0.15    --  -91.75  61.00-150.00  104
 31  ω    -38.00  28.00   0.50    0.05    --  -46.64  31.00-148.00  132
 32  ω    -51.00 -19.00   0.50    0.15    --  -91.75  45.00  30.00   64
 33  ω    -71.00 -19.00   0.50    0.15    --  -91.75  61.00  30.00  104
 34  ω   -167.00 -74.00   0.50    0.15    --  -91.75 -15.00 -90.00  186
 35  ω   -164.00 -77.00   0.50    0.15    --  -91.75 -45.00 -65.95  174
 36  ω   -164.00-101.00   0.50    0.15    --  -91.75 -77.00   0.00  126
 37  ω   -164.00-101.00   0.50    0.15    --  -91.75 -77.00  30.00  126
 38  ω   -166.00 -76.00   0.50    0.15    --  -91.75 -31.00  51.00  180
 39  ω   -164.00-100.00   0.50    0.15    --  -91.75 -94.00 150.00  128
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1597575000
_diffrn_orient_matrix_UB_12      0.0456902000
_diffrn_orient_matrix_UB_13      0.0344423000
_diffrn_orient_matrix_UB_21      -0.0149236000
_diffrn_orient_matrix_UB_22      0.1431657000
_diffrn_orient_matrix_UB_23      -0.0388962000
_diffrn_orient_matrix_UB_31      -0.0482017000
_diffrn_orient_matrix_UB_32      0.0438486000
_diffrn_orient_matrix_UB_33      0.1197113000
_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                3797
_reflns_number_total             4297
_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 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0017(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   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     296
_refine_ls_number_reflns         4297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      1.022
_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)+(0.0500P)²+0.7500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1297
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H6 of C6, H5 of C5, H19B of C19B, H19A of C19A, H4 of C4,
   H9 of C9, H13 of C13, H1A of C1, H3 of C3, H10 of C10, H11 of C11, H7 of C7,
  H12 of C12, All C(H,H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  H1B of C22B
2. Others
 Fixed Sof: H20A(0.55) H20B(0.55) H20C(0.45) H20D(0.45) H23C(0.5) H23D(0.5)
 H23A(0.5) H23B(0.5) H21A(0.5) H21B(0.5) H21C(0.5) H21D(0.5) C24A(0.55)
 H24A(0.55) H24B(0.55) C24B(0.45) H24C(0.45) H24D(0.45) C22A(0.5) H22A(0.5)
 H22B(0.5) C22B(0.5) H22C(0.5) H22D(0.5) C19A(0.55) H19A(0.55) C19B(0.45)
 H19B(0.45)
3.a Ternary CH refined with riding coordinates:
 C1(H1A), C13(H13), C19A(H19A), C19B(H19B)
3.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C20(H20A,H20B), C20(H20C,H20D), C16(H16A,
 H16B), C14(H14A,H14B), C15(H15A,H15B), C23(H23C,H23D), C23(H23A,H23B),
 C21(H21A,H21B), C21(H21C,H21D), C24A(H24A,H24B), C24B(H24C,H24D), C22A(H22A,
 H22B), C22B(H22C,H22D)
3.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C9(H9), C3(H3), C4(H4), C10(H10), C7(H7), C6(H6), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69970(13) 0.15414(11) 0.75216(10) 0.0311(3) Uani 1 1 d . . . . .
O2 O 0.75524(14) 0.37709(11) 0.78243(11) 0.0380(3) Uani 1 1 d . . . . .
N2 N 0.46231(15) 0.19852(15) 0.64049(12) 0.0332(3) Uani 1 1 d . . . . .
N1 N 0.29232(15) 0.34220(15) 0.27303(14) 0.0363(4) Uani 1 1 d . . . . .
C1 C 0.20235(16) 0.25611(15) 0.34595(13) 0.0256(3) Uani 1 1 d . . . . .
H1A H 0.175639 0.165949 0.304187 0.031 Uiso 1 1 calc R U . . .
C8 C 0.28910(16) 0.23387(15) 0.45175(13) 0.0250(3) Uani 1 1 d . . . . .
C12 C 0.30309(17) 0.10543(15) 0.48783(13) 0.0261(3) Uani 1 1 d . . . . .
H12 H 0.253329 0.027095 0.448629 0.031 Uiso 1 1 calc R U . . .
C11 C 0.39002(17) 0.09226(16) 0.58132(14) 0.0291(3) Uani 1 1 d . . . . .
H11 H 0.398792 0.003579 0.604580 0.035 Uiso 1 1 calc R U . . .
C17 C -0.17904(17) 0.27876(16) 0.47911(14) 0.0296(3) Uani 1 1 d . . . . .
H17A H -0.241730 0.211021 0.520353 0.036 Uiso 1 1 calc R U . . .
H17B H -0.157516 0.361658 0.530016 0.036 Uiso 1 1 calc R U . . .
C25 C 0.78731(17) 0.26281(16) 0.78741(14) 0.0283(3) Uani 1 1 d . . . . .
C18 C -0.03684(17) 0.22176(16) 0.44826(14) 0.0293(3) Uani 1 1 d . . . . .
H18A H -0.059334 0.132747 0.405684 0.035 Uiso 1 1 calc R U . . .
H18B H 0.016085 0.206872 0.518615 0.035 Uiso 1 1 calc R U . . .
C13 C 0.06075(16) 0.31729(16) 0.37661(14) 0.0285(3) Uani 1 1 d . . . . .
H13 H 0.087515 0.404417 0.422838 0.034 Uiso 1 1 calc R U . . .
C2 C 0.39711(16) 0.29222(18) 0.20375(14) 0.0312(4) Uani 1 1 d . . . . .
C9 C 0.36081(18) 0.34417(17) 0.51558(16) 0.0347(4) Uani 1 1 d . . . . .
H9 H 0.351831 0.434108 0.495536 0.042 Uiso 1 1 calc R U . . .
C3 C 0.42425(17) 0.15676(17) 0.20067(14) 0.0317(4) Uani 1 1 d . . . . .
H3 H 0.371090 0.095583 0.248166 0.038 Uiso 1 1 calc R U . . .
C4 C 0.52778(19) 0.11071(19) 0.12913(15) 0.0362(4) Uani 1 1 d . . . . .
H4 H 0.544175 0.017891 0.127505 0.043 Uiso 1 1 calc R U . . .
C20 C 0.99242(19) 0.32651(17) 0.92787(15) 0.0329(4) Uani 1 1 d . . . . .
H20A H 0.930373 0.344648 0.993584 0.039 Uiso 0.55 1 calc R U P A 1
H20B H 1.005854 0.409758 0.885206 0.039 Uiso 0.55 1 calc R U P A 1
H20C H 0.995354 0.425591 0.920367 0.039 Uiso 0.45 1 calc R U P B 2
H20D H 0.918172 0.300244 0.984785 0.039 Uiso 0.45 1 calc R U P B 2
C16 C -0.25989(18) 0.31311(18) 0.37404(15) 0.0345(4) Uani 1 1 d . . . . .
H16A H -0.347720 0.355474 0.396964 0.041 Uiso 1 1 calc R U . . .
H16B H -0.291498 0.228668 0.327215 0.041 Uiso 1 1 calc R U . . .
C10 C 0.44502(19) 0.32270(18) 0.60806(17) 0.0385(4) Uani 1 1 d . . . . .
H10 H 0.492861 0.399437 0.650627 0.046 Uiso 1 1 calc R U . . .
C7 C 0.47943(18) 0.38059(19) 0.13366(16) 0.0377(4) Uani 1 1 d . . . . .
H7 H 0.463946 0.473629 0.135007 0.045 Uiso 1 1 calc R U . . .
C14 C -0.02350(18) 0.3489(2) 0.27132(16) 0.0369(4) Uani 1 1 d . . . . .
H14A H -0.048845 0.264303 0.223095 0.044 Uiso 1 1 calc R U . . .
H14B H 0.038643 0.413575 0.226814 0.044 Uiso 1 1 calc R U . . .
C6 C 0.58283(19) 0.3326(2) 0.06277(17) 0.0439(5) Uani 1 1 d . . . . .
H6 H 0.637357 0.393072 0.015450 0.053 Uiso 1 1 calc R U . . .
C5 C 0.6077(2) 0.1976(2) 0.06001(16) 0.0426(5) Uani 1 1 d . . . . .
H5 H 0.678868 0.165167 0.011216 0.051 Uiso 1 1 calc R U . . .
C15 C -0.16275(19) 0.4102(2) 0.30459(17) 0.0416(4) Uani 1 1 d . . . . .
H15A H -0.137259 0.497306 0.349383 0.050 Uiso 1 1 calc R U . . .
H15B H -0.215870 0.428974 0.235401 0.050 Uiso 1 1 calc R U . . .
C23 C 1.1407(2) 0.0994(2) 0.83425(18) 0.0500(5) Uani 1 1 d . . . . .
H23C H 1.167239 0.005479 0.829465 0.060 Uiso 0.5 1 calc R U P C 2
H23D H 1.195250 0.150899 0.775875 0.060 Uiso 0.5 1 calc R U P C 2
H23A H 1.206034 0.057322 0.780249 0.060 Uiso 0.5 1 calc R U P D 1
H23B H 1.097964 0.029338 0.884255 0.060 Uiso 0.5 1 calc R U P D 1
C21 C 1.1379(3) 0.2970(3) 0.9702(3) 0.0956(13) Uani 1 1 d . . . . .
H21A H 1.193719 0.386050 0.991983 0.115 Uiso 0.5 1 calc R U P E 1
H21B H 1.119758 0.250097 1.041210 0.115 Uiso 0.5 1 calc R U P E 1
H21C H 1.212911 0.361400 0.936756 0.115 Uiso 0.5 1 calc R U P F 2
H21D H 1.141743 0.318039 1.053174 0.115 Uiso 0.5 1 calc R U P F 2
C24A C 1.0207(4) 0.1588(4) 0.7704(3) 0.0354(7) Uani 0.55 1 d . . P G 1
H24A H 1.064307 0.231908 0.723577 0.042 Uiso 0.55 1 calc R U P G 1
H24B H 0.966883 0.087081 0.719466 0.042 Uiso 0.55 1 calc R U P G 1
C24B C 0.9698(4) 0.0976(4) 0.8132(4) 0.0311(8) Uani 0.45 1 d . . P G 2
H24C H 0.939038 0.045442 0.741437 0.037 Uiso 0.45 1 calc R U P G 2
H24D H 0.914586 0.055799 0.876104 0.037 Uiso 0.45 1 calc R U P G 2
C22A C 1.2294(4) 0.2242(4) 0.9081(3) 0.0358(8) Uani 0.5 1 d . . P G 1
H22A H 1.298640 0.188569 0.959616 0.043 Uiso 0.5 1 calc R U P G 1
H22B H 1.286193 0.284729 0.856824 0.043 Uiso 0.5 1 calc R U P G 1
C22B C 1.1785(4) 0.1658(4) 0.9500(4) 0.0389(8) Uani 0.5 1 d . . P G 2
H22C H 1.131488 0.106896 1.007151 0.047 Uiso 0.5 1 calc R U P G 2
H22D H 1.284963 0.170320 0.961828 0.047 Uiso 0.5 1 calc R U P G 2
H1 H 0.265(2) 0.426(2) 0.2588(18) 0.047 Uiso 1 1 d . U . . .
H1B H 0.609(3) 0.181(2) 0.716(2) 0.058 Uiso 1 1 d . U . . .
C19A C 0.9174(4) 0.2154(4) 0.8546(3) 0.0277(7) Uani 0.55 1 d . . P G 1
H19A H 0.878033 0.141038 0.903205 0.033 Uiso 0.55 1 calc R U P G 1
C19B C 0.9434(4) 0.2482(4) 0.8074(4) 0.0221(8) Uani 0.45 1 d . . P G 2
H19B H 1.003090 0.290045 0.745620 0.027 Uiso 0.45 1 calc R U P G 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C25 1.3168(19) . ?
O2 C25 1.2100(19) . ?
N2 C11 1.338(2) . ?
N2 C10 1.339(2) . ?
N1 C1 1.450(2) . ?
N1 C2 1.390(2) . ?
C1 C8 1.523(2) . ?
C1 C13 1.544(2) . ?
C8 C12 1.388(2) . ?
C8 C9 1.391(2) . ?
C12 C11 1.384(2) . ?
C17 C18 1.530(2) . ?
C17 C16 1.522(2) . ?
C25 C19A 1.570(4) . ?
C25 C19B 1.488(4) . ?
C18 C13 1.531(2) . ?
C13 C14 1.532(2) . ?
C2 C3 1.395(2) . ?
C2 C7 1.407(2) . ?
C9 C10 1.380(2) . ?
C3 C4 1.382(2) . ?
C4 C5 1.381(3) . ?
C20 C21 1.500(3) . ?
C20 C19A 1.466(4) . ?
C20 C19B 1.618(4) . ?
C16 C15 1.522(2) . ?
C7 C6 1.384(3) . ?
C14 C15 1.532(2) . ?
C6 C5 1.385(3) . ?
C23 C24A 1.531(4) . ?
C23 C24B 1.598(4) . ?
C23 C22A 1.610(4) . ?
C23 C22B 1.504(4) . ?
C21 C22A 1.367(4) . ?
C21 C22B 1.404(4) . ?
C24A C19A 1.515(5) . ?
C24B C19B 1.547(5) . ?

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
C11 N2 C10 117.36(14) . . ?
C2 N1 C1 122.07(14) . . ?
N1 C1 C8 109.45(12) . . ?
N1 C1 C13 111.28(12) . . ?
C8 C1 C13 111.31(13) . . ?
C12 C8 C1 122.60(14) . . ?
C12 C8 C9 117.09(14) . . ?
C9 C8 C1 120.30(14) . . ?
C11 C12 C8 119.55(14) . . ?
N2 C11 C12 123.13(15) . . ?
C16 C17 C18 111.42(13) . . ?
O1 C25 C19A 108.23(17) . . ?
O1 C25 C19B 118.34(19) . . ?
O2 C25 O1 122.90(15) . . ?
O2 C25 C19A 127.85(18) . . ?
O2 C25 C19B 117.0(2) . . ?
C17 C18 C13 112.06(13) . . ?
C18 C13 C1 110.71(12) . . ?
C18 C13 C14 109.71(13) . . ?
C14 C13 C1 112.17(14) . . ?
N1 C2 C3 122.45(15) . . ?
N1 C2 C7 119.31(16) . . ?
C3 C2 C7 118.24(16) . . ?
C10 C9 C8 119.88(15) . . ?
C4 C3 C2 120.59(16) . . ?
C5 C4 C3 120.98(17) . . ?
C21 C20 C19B 113.8(2) . . ?
C19A C20 C21 113.29(19) . . ?
C17 C16 C15 110.64(14) . . ?
N2 C10 C9 122.93(16) . . ?
C6 C7 C2 120.32(17) . . ?
C13 C14 C15 110.88(15) . . ?
C7 C6 C5 120.77(16) . . ?
C4 C5 C6 119.09(17) . . ?
C16 C15 C14 110.56(15) . . ?
C24A C23 C22A 106.5(2) . . ?
C22B C23 C24B 108.3(2) . . ?
C22A C21 C20 123.7(3) . . ?
C22B C21 C20 119.0(2) . . ?
C19A C24A C23 109.4(3) . . ?
C19B C24B C23 105.7(3) . . ?
C21 C22A C23 111.4(3) . . ?
C21 C22B C23 115.7(3) . . ?
C20 C19A C25 111.7(2) . . ?
C20 C19A C24A 111.1(3) . . ?
C24A C19A C25 108.5(3) . . ?
C25 C19B C20 108.0(2) . . ?
C25 C19B C24B 111.9(3) . . ?
C24B C19B C20 108.0(3) . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.128
_oxdiff_exptl_absorpt_empirical_full_min 0.893
####################################################################### 
# 
# 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_hpd805_auto
_database_code_depnum_ccdc_archive 'CCDC 2340501'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman '
;The University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2024-03-14 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2023-11-07
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 N O'
_chemical_formula_sum            'C21 H23 N O'
_chemical_formula_weight         305.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'MCR 3'
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                   5.71447(11)
_cell_length_b                   17.9506(3)
_cell_length_c                   16.3618(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.380(2)
_cell_angle_gamma                90
_cell_volume                     1655.93(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9444
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.7690
_cell_measurement_theta_min      3.6670
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.903
_exptl_absorpt_coefficient_mu    0.575
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.536
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 7 -1 0.0955
0 5 -9 0.0519
3 -5 -2 0.0754
0 -5 9 0.0335
0 4 10 0.0252
2 9 -1 0.0661
0 -4 -10 0.0438
-2 -9 2 0.0524

_exptl_crystal_size_max          0.182
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.071
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
-2.9085 6.7028 -1.0895 0.2337 0.9710 0.0497
0.4219 5.3069 -9.4444 0.0973 0.4133 -0.9054
3.2967 -5.2745 -2.3173 -0.2163 -0.8956 -0.3886
-0.3684 -5.3880 9.3998 -0.1007 -0.4275 0.8984
-0.2335 4.1333 9.8811 0.6566 -0.1596 0.7372
2.2736 9.2090 -1.1978 0.8485 -0.2030 -0.4888
0.3243 -3.8072 -10.0094 -0.6288 0.1530 -0.7624
-2.3429 -8.9368 2.2970 -0.7934 0.1895 0.5785

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15461
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.736
_diffrn_reflns_theta_min         3.682
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     34.00 101.00   0.50    1.04    --  106.92 -77.00 -60.00  134
  2  ω     34.00  71.00   0.50    1.04    --  106.92 -61.00 -60.00   74
  3  ω     34.00 101.00   0.50    1.04    --  106.92 -77.00  30.00  134
  4  ω     34.00  71.00   0.50    1.04    --  106.92 -61.00  60.00   74
  5  ω     34.00  71.00   0.50    1.04    --  106.92 -61.00 120.00   74
  6  ω    -26.00  49.00   0.50    0.26    --   46.89 -43.00  59.00  150
  7  ω     32.00  95.00   0.50    0.26    --   46.89  37.00 -60.00  126
  8  ω     92.00 178.00   0.50    1.04    --  106.92  43.00-149.00  172
  9  ω     33.00 120.00   0.50    0.26    --   46.89  43.00-149.00  174
 10  ω    -51.00 -19.00   0.50    1.04    --  -91.75  45.00-180.00   64
 11  ω    -51.00 -19.00   0.50    1.04    --  -91.75  45.00 -60.00   64
 12  ω    -49.00 -18.00   0.50    1.04    --  -91.75  43.00-149.00   62
 13  ω    -49.00  27.00   0.50    0.26    --  -46.89  43.00-149.00  152
 14  ω    -51.00 -19.00   0.50    1.04    --  -91.75  45.00  30.00   64
 15  ω    -71.00 -19.00   0.50    1.04    --  -91.75  61.00  30.00  104
 16  ω    -51.00 -19.00   0.50    1.04    --  -91.75  45.00 150.00   64
 17  ω   -164.00 -76.00   0.50    1.04    --  -91.75 -43.00  59.00  176
 18  ω   -164.00-101.00   0.50    1.04    --  -91.75 -77.00 120.00  126
 19  ω   -164.00-101.00   0.50    1.04    --  -91.75 -77.00 150.00  126
 20  ω   -119.00 -32.00   0.50    0.26    --  -46.89 -43.00  59.00  174
 21  ω   -164.00 -91.00   0.50    1.04    --  -91.75 -61.00   0.00  146
 22  ω   -164.00-101.00   0.50    1.04    --  -91.75 -77.00-180.00  126
 23  ω    -85.00 -13.00   0.50    0.26    --  -46.89 125.00 -90.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0823881000
_diffrn_orient_matrix_UB_12      0.0765273000
_diffrn_orient_matrix_UB_13      0.0363804000
_diffrn_orient_matrix_UB_21      -0.2434548000
_diffrn_orient_matrix_UB_22      0.0333977000
_diffrn_orient_matrix_UB_23      -0.0358722000
_diffrn_orient_matrix_UB_31      -0.0927028000
_diffrn_orient_matrix_UB_32      -0.0196948000
_diffrn_orient_matrix_UB_33      0.0806554000
_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                2778
_reflns_number_total             3206
_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 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.570
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.051
_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)+(0.0450P)²+0.6768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1053
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C21(H21A,H21B), C20(H20A,H20B), C19(H19A,H19B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C11(H11), C14(H14), C13(H13), C5(H5), C15(H15), C12(H12),
 C6(H6), C8(H8), C7(H7)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.81309(16) 0.68538(5) 0.38984(6) 0.0234(2) Uani 1 1 d . . . . .
N1 N 0.6470(2) 0.76980(6) 0.51811(7) 0.0233(3) Uani 1 1 d . . . . .
H1 H 0.766851 0.789714 0.551584 0.028 Uiso 1 1 calc R U . . .
C10 C 0.4811(2) 0.81674(7) 0.47175(8) 0.0215(3) Uani 1 1 d . . . . .
C2 C 0.6206(2) 0.66252(7) 0.42525(8) 0.0214(3) Uani 1 1 d . . . . .
C9 C 0.7664(2) 0.66300(7) 0.30824(8) 0.0225(3) Uani 1 1 d . . . . .
C3 C 0.4613(2) 0.62571(7) 0.37018(8) 0.0239(3) Uani 1 1 d . . . . .
H3 H 0.316873 0.604262 0.380416 0.029 Uiso 1 1 calc R U . . .
C11 C 0.2519(2) 0.79316(7) 0.43964(8) 0.0234(3) Uani 1 1 d . . . . .
H11 H 0.207278 0.742866 0.446559 0.028 Uiso 1 1 calc R U . . .
C4 C 0.5507(2) 0.62489(7) 0.29277(8) 0.0233(3) Uani 1 1 d . . . . .
C1 C 0.6282(2) 0.68848(7) 0.51287(8) 0.0217(3) Uani 1 1 d . . . . .
H1A H 0.475707 0.673655 0.530831 0.026 Uiso 1 1 calc R U . . .
C14 C 0.3771(3) 0.94020(8) 0.41852(9) 0.0266(3) Uani 1 1 d . . . . .
H14 H 0.420745 0.990546 0.411301 0.032 Uiso 1 1 calc R U . . .
C13 C 0.1487(3) 0.91659(8) 0.38697(9) 0.0277(3) Uani 1 1 d . . . . .
H13 H 0.035759 0.950401 0.358618 0.033 Uiso 1 1 calc R U . . .
C5 C 0.4730(3) 0.59872(8) 0.21209(9) 0.0273(3) Uani 1 1 d . . . . .
H5 H 0.327001 0.572675 0.198807 0.033 Uiso 1 1 calc R U . . .
C16 C 0.8330(2) 0.65384(7) 0.57408(8) 0.0232(3) Uani 1 1 d . . . . .
H16 H 0.985582 0.672460 0.559257 0.028 Uiso 1 1 calc R U . . .
C15 C 0.5417(2) 0.89130(7) 0.46034(8) 0.0241(3) Uani 1 1 d . . . . .
H15 H 0.697168 0.908359 0.481507 0.029 Uiso 1 1 calc R U . . .
C12 C 0.0886(2) 0.84286(8) 0.39757(9) 0.0260(3) Uani 1 1 d . . . . .
H12 H -0.066659 0.826021 0.375764 0.031 Uiso 1 1 calc R U . . .
C6 C 0.6138(3) 0.61170(8) 0.15235(9) 0.0297(3) Uani 1 1 d . . . . .
H6 H 0.563680 0.593896 0.097619 0.036 Uiso 1 1 calc R U . . .
C17 C 0.8226(3) 0.67802(8) 0.66359(8) 0.0265(3) Uani 1 1 d . . . . .
H17A H 0.835036 0.732956 0.667556 0.032 Uiso 1 1 calc R U . . .
H17B H 0.667757 0.663264 0.678262 0.032 Uiso 1 1 calc R U . . .
C8 C 0.9092(2) 0.67690(8) 0.24980(9) 0.0275(3) Uani 1 1 d . . . . .
H8 H 1.054886 0.703126 0.262967 0.033 Uiso 1 1 calc R U . . .
C21 C 0.8329(3) 0.56885(8) 0.56765(9) 0.0267(3) Uani 1 1 d . . . . .
H21A H 0.679562 0.549255 0.579096 0.032 Uiso 1 1 calc R U . . .
H21B H 0.849749 0.554158 0.510575 0.032 Uiso 1 1 calc R U . . .
C7 C 0.8282(3) 0.65047(9) 0.17074(9) 0.0306(3) Uani 1 1 d . . . . .
H7 H 0.920099 0.658819 0.128168 0.037 Uiso 1 1 calc R U . . .
C20 C 1.0352(3) 0.53472(8) 0.62885(9) 0.0305(3) Uani 1 1 d . . . . .
H20A H 1.026874 0.479728 0.624741 0.037 Uiso 1 1 calc R U . . .
H20B H 1.189000 0.550810 0.614369 0.037 Uiso 1 1 calc R U . . .
C19 C 1.0214(3) 0.55824(8) 0.71719(9) 0.0321(3) Uani 1 1 d . . . . .
H19A H 1.158524 0.537464 0.755134 0.039 Uiso 1 1 calc R U . . .
H19B H 0.874751 0.537964 0.733603 0.039 Uiso 1 1 calc R U . . .
C18 C 1.0217(3) 0.64295(8) 0.72495(9) 0.0308(3) Uani 1 1 d . . . . .
H18A H 1.002356 0.656862 0.782021 0.037 Uiso 1 1 calc R U . . .
H18B H 1.176095 0.662669 0.714730 0.037 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3860(16) . ?
O1 C9 1.3781(16) . ?
N1 C10 1.3967(17) . ?
N1 C1 1.4650(17) . ?
C10 C11 1.3948(18) . ?
C10 C15 1.4025(19) . ?
C2 C3 1.3454(18) . ?
C2 C1 1.5014(18) . ?
C9 C4 1.3962(19) . ?
C9 C8 1.377(2) . ?
C3 C4 1.441(2) . ?
C11 C12 1.3898(19) . ?
C4 C5 1.4034(19) . ?
C1 C16 1.5418(17) . ?
C14 C13 1.389(2) . ?
C14 C15 1.3835(19) . ?
C13 C12 1.385(2) . ?
C5 C6 1.383(2) . ?
C16 C17 1.5378(19) . ?
C16 C21 1.5293(19) . ?
C6 C7 1.399(2) . ?
C17 C18 1.5251(19) . ?
C8 C7 1.385(2) . ?
C21 C20 1.5288(18) . ?
C20 C19 1.520(2) . ?
C19 C18 1.526(2) . ?

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
C9 O1 C2 106.09(10) . . ?
C10 N1 C1 122.17(10) . . ?
N1 C10 C15 119.16(12) . . ?
C11 C10 N1 122.29(12) . . ?
C11 C10 C15 118.47(12) . . ?
O1 C2 C1 113.95(11) . . ?
C3 C2 O1 111.22(12) . . ?
C3 C2 C1 134.66(13) . . ?
O1 C9 C4 110.13(12) . . ?
C8 C9 O1 125.23(12) . . ?
C8 C9 C4 124.63(13) . . ?
C2 C3 C4 107.18(12) . . ?
C12 C11 C10 120.35(13) . . ?
C9 C4 C3 105.35(11) . . ?
C9 C4 C5 117.99(13) . . ?
C5 C4 C3 136.62(13) . . ?
N1 C1 C2 110.83(11) . . ?
N1 C1 C16 108.85(10) . . ?
C2 C1 C16 113.32(11) . . ?
C15 C14 C13 120.81(13) . . ?
C12 C13 C14 118.82(13) . . ?
C6 C5 C4 118.48(13) . . ?
C17 C16 C1 111.21(11) . . ?
C21 C16 C1 111.47(11) . . ?
C21 C16 C17 110.34(11) . . ?
C14 C15 C10 120.55(12) . . ?
C13 C12 C11 121.00(13) . . ?
C5 C6 C7 121.47(13) . . ?
C18 C17 C16 111.72(12) . . ?
C9 C8 C7 116.16(13) . . ?
C20 C21 C16 111.28(11) . . ?
C8 C7 C6 121.27(14) . . ?
C19 C20 C21 111.14(12) . . ?
C20 C19 C18 110.88(12) . . ?
C17 C18 C19 111.47(12) . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.630
_oxdiff_exptl_absorpt_empirical_full_min 0.639
####################################################################### 
# 
# 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_hpd801b_auto
_database_code_depnum_ccdc_archive 'CCDC 2340503'
loop_
_audit_author_name
_audit_author_address
'Hadi D. Arman '
;The University of Texas at San Antonio
United States of America
;
_audit_update_record             
;
2024-03-14 deposited with the CCDC.	2024-05-21 downloaded from the CCDC.
;
_audit_creation_date             2023-11-21
_audit_creation_method           
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H29 N O3'
_chemical_formula_sum            'C23 H29 N O3'
_chemical_formula_weight         367.47
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'MCR -11'
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                   8.8935(2)
_cell_length_b                   14.9861(4)
_cell_length_c                   16.6162(3)
_cell_angle_alpha                112.739(2)
_cell_angle_beta                 90.306(2)
_cell_angle_gamma                103.676(2)
_cell_volume                     1972.96(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14708
_cell_measurement_temperature    100.01(15)
_cell_measurement_theta_max      76.2220
_cell_measurement_theta_min      2.9160
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.876
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.648
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             792
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -1 9 0.0653
-2 10 -3 0.0349
3 2 -9 0.0994
2 -10 3 0.0545
-5 0 -1 0.1272
0 1 9 0.0344
5 1 4 0.0323
0 -1 -9 0.0595

_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.114
_exptl_crystal_size_min          0.09
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
-3.2821 -1.2762 8.8828 0.1805 0.1265 0.9754
-2.2615 9.5584 -3.0599 -0.7965 -0.5463 0.2591
3.0170 2.3662 -9.2149 -0.2712 -0.1887 -0.9439
2.2849 -9.5460 2.9936 0.7950 0.5452 -0.2661
-5.4788 -0.2239 -0.6857 0.4980 -0.7233 0.4784
0.4447 1.1089 9.1776 -0.4025 0.5890 0.7008
4.8358 0.5511 3.5619 -0.5569 0.8103 -0.1826
-0.3203 -1.1109 -9.2214 0.3936 -0.5760 -0.7164

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            37064
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.326
_diffrn_reflns_theta_min         2.900
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(15)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  26.00   0.50    3.00    --  -46.89  53.00   6.00  172
  2  ω   -119.00 -31.00   0.50    3.00    --  -46.89 -53.00-138.00  176
  3  ω     32.00 119.00   0.50    3.00    --   46.89  53.00   6.00  174
  4  ω   -164.00 -76.00   0.50   12.00    --  -91.75 -53.00-138.00  176
  5  ω    -60.00 -19.00   0.50   12.00    --  -91.75  53.00   6.00   82
  6  ω     34.00  60.00   0.50   12.00    --  106.92 -53.00-138.00   52
  7  ω     92.00 178.00   0.50   12.00    --  106.92  53.00   6.00  172
  8  ω    -85.00 -13.00   0.50    3.00    --  -46.89 125.00-180.00  144
  9  ω     83.00 119.00   0.50    3.00    --   46.89  57.00 -30.00   72
 10  ω    -25.00  60.00   0.50    3.00    --   46.89 -53.00-138.00  170
 11  ω     34.00  94.00   0.50    3.00    --   46.89-125.00-120.00  120
 12  ω    -28.00  30.00   0.50    3.00    --   46.89 -19.00 -90.00  116
 13  ω     83.00 119.00   0.50    3.00    --   46.89  57.00-180.00   72
 14  ω    -51.00 -19.00   0.50   12.00    --  -91.75  45.00 120.00   64
 15  ω   -164.00 -78.00   0.50   12.00    --  -91.75 -56.00 -75.14  172
 16  ω   -101.00 -19.00   0.50   12.00    --  -91.75  77.00-180.00  164
 17  ω   -164.00-101.00   0.50   12.00    --  -91.75 -77.00-180.00  126
 18  ω   -164.00 -83.00   0.50   12.00    --  -91.75 -57.00 -87.57  162
 19  ω   -164.00-101.00   0.50   12.00    --  -91.75 -77.00 -30.00  126
 20  ω    -71.00 -19.00   0.50   12.00    --  -91.75  61.00-180.00  104
 21  ω     34.00 106.00   0.50   12.00    --  106.92 -94.00 150.00  144
 22  ω     34.00  71.00   0.50   12.00    --  106.92 -61.00  90.00   74
 23  ω     34.00 106.00   0.50   12.00    --  106.92 -94.00   0.00  144
 24  ω     34.00 101.00   0.50   12.00    --  106.92 -77.00   0.00  134
 25  ω     34.00  71.00   0.50   12.00    --  106.92 -61.00  30.00   74
 26  ω     37.00 112.00   0.50   12.00    --  106.92-125.00 -90.00  150
 27  ω     37.00 112.00   0.50   12.00    --  106.92-125.00 120.00  150
 28  ω     34.00 106.00   0.50   12.00    --  106.92 -94.00-120.00  144
 29  ω     34.00 106.00   0.50   12.00    --  106.92 -94.00 -60.00  144
 30  ω     34.00  71.00   0.50   12.00    --  106.92 -61.00-150.00   74
 31  ω     92.00 178.00   0.50   12.00    --  106.92  30.00-150.00  172
 32  ω     38.00 109.00   0.50   12.00    --  106.92-116.00   9.29  142
 33  ω    101.00 178.00   0.50   12.00    --  106.92  77.00 -60.00  154
 34  ω     93.00 178.00   0.50   12.00    --  106.92  45.00  90.00  170
 35  ω     37.00 112.00   0.50   12.00    --  106.92-125.00 150.00  150
 36  ω     37.00 112.00   0.50   12.00    --  106.92-125.00   0.00  150
 37  ω     34.00 106.00   0.50   12.00    --  106.92 -94.00-180.00  144
 38  ω     34.00  71.00   0.50   12.00    --  106.92 -61.00   0.00   74
 39  ω   -119.00 -83.00   0.50    3.00    --  -46.89 -57.00 -30.00   72
 40  ω     31.00 119.00   0.50    3.00    --   46.89  55.00-178.70  176
 41  ω     31.00 119.00   0.50    3.00    --   46.89  55.00 102.38  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0830345000
_diffrn_orient_matrix_UB_12      -0.1114223000
_diffrn_orient_matrix_UB_13      -0.0263716000
_diffrn_orient_matrix_UB_21      0.1249626000
_diffrn_orient_matrix_UB_22      -0.0086435000
_diffrn_orient_matrix_UB_23      0.0591676000
_diffrn_orient_matrix_UB_31      -0.0982193000
_diffrn_orient_matrix_UB_32      0.0287201000
_diffrn_orient_matrix_UB_33      0.0776451000
_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                6789
_reflns_number_total             8018
_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 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     497
_refine_ls_number_reflns         8018
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0783
_refine_ls_restrained_S_all      1.073
_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)+(0.0100P)²+5.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1685
_refine_ls_wR_factor_ref         0.1732
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H11,H1,H2} of C11, All C(H,H) groups
 At 1.5 times of:
  {H23A,H23B,H23C} of C23, {H39A,H39B,H39C} of C39, {H16A,H16B,H16C} of C16,
  {H46A,H46B,H46C} of C46
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C30(H30A,H30B), C27(H27A,H27B), C7(H7A,H7B), C28(H28A,H28B),
 C3(H3A,H3B), C15(H15A,H15B), C38(H38A,H38B), C4(H4A,H4B), C6(H6A,H6B),
 C29(H29A,H29B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C45(H45), C21(H21), C18(H18), C41(H41), C42(H42), C44(H44),
 C36(H36), C19(H19), C32(H32), C9(H9), C13(H13), C35(H35), C33(H33), C34(H34),
 C12(H12), C10(H10), C11(H11)
2.d Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C16(H16A,H16B,H16C), C46(H46A,H46B,H46C), C23(H23A,H23B,
 H23C)
;
_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
O5 O 0.4816(2) 0.60863(16) 0.45360(13) 0.0278(4) Uani 1 1 d . . . . .
O1 O 0.9071(2) 0.61278(16) 0.25219(13) 0.0302(5) Uani 1 1 d . . . . .
O2 O 0.9771(2) 0.60886(16) 0.12068(13) 0.0282(4) Uani 1 1 d . . . . .
O4 O 0.4102(2) 0.61963(16) 0.32759(13) 0.0303(5) Uani 1 1 d . . . . .
O6 O 0.0305(3) 0.14035(16) 0.20623(15) 0.0362(5) Uani 1 1 d . . . . .
O3 O 0.5194(2) 0.14377(16) 0.05557(16) 0.0389(5) Uani 1 1 d . . . . .
N2 N 0.0943(3) 0.55267(18) 0.36719(16) 0.0242(5) Uani 1 1 d . . . . .
N1 N 0.5913(3) 0.55570(18) 0.17079(16) 0.0244(5) Uani 1 1 d . . . . .
C43 C 0.0393(3) 0.2406(2) 0.24319(19) 0.0275(6) Uani 1 1 d . . . . .
C40 C 0.0790(3) 0.4503(2) 0.32658(18) 0.0239(6) Uani 1 1 d . . . . .
C37 C 0.3810(3) 0.6152(2) 0.39697(18) 0.0241(6) Uani 1 1 d . . . . .
C22 C 0.4533(3) 0.3946(2) 0.16791(18) 0.0257(6) Uani 1 1 d . . . . .
H22 H 0.384663 0.426255 0.205687 0.031 Uiso 1 1 calc R U . . .
C45 C -0.0451(3) 0.3884(2) 0.26177(18) 0.0255(6) Uani 1 1 d . . . . .
H45 H -0.117178 0.417850 0.245578 0.031 Uiso 1 1 calc R U . . .
C25 C 0.2104(3) 0.7272(2) 0.47919(18) 0.0235(6) Uani 1 1 d . . . . .
C14 C 0.8773(3) 0.6125(2) 0.18108(18) 0.0244(6) Uani 1 1 d . . . . .
C1 C 0.7191(3) 0.6179(2) 0.14791(18) 0.0235(6) Uani 1 1 d . . . . .
H1A H 0.712385 0.590600 0.082376 0.028 Uiso 1 1 calc R U . . .
C17 C 0.5743(3) 0.4534(2) 0.14201(18) 0.0231(6) Uani 1 1 d . . . . .
C21 C 0.4306(3) 0.2927(2) 0.14047(19) 0.0282(6) Uani 1 1 d . . . . .
H21 H 0.346987 0.255264 0.159054 0.034 Uiso 1 1 calc R U . . .
C18 C 0.6730(3) 0.4028(2) 0.08578(18) 0.0256(6) Uani 1 1 d . . . . .
H18 H 0.756323 0.439718 0.066516 0.031 Uiso 1 1 calc R U . . .
C41 C 0.1835(3) 0.4028(2) 0.34786(18) 0.0251(6) Uani 1 1 d . . . . .
H41 H 0.269574 0.441894 0.391103 0.030 Uiso 1 1 calc R U . . .
C31 C 0.3526(3) 0.7834(2) 0.54908(19) 0.0256(6) Uani 1 1 d . . . . .
C2 C 0.7121(3) 0.7295(2) 0.18051(18) 0.0238(6) Uani 1 1 d . . . . .
C24 C 0.2226(3) 0.6168(2) 0.43347(18) 0.0238(6) Uani 1 1 d . . . . .
H24 H 0.219677 0.589555 0.479851 0.029 Uiso 1 1 calc R U . . .
C42 C 0.1625(3) 0.3009(2) 0.30701(19) 0.0264(6) Uani 1 1 d . . . . .
H42 H 0.234288 0.271078 0.322958 0.032 Uiso 1 1 calc R U . . .
C20 C 0.5308(3) 0.2441(2) 0.0851(2) 0.0279(6) Uani 1 1 d . . . . .
C44 C -0.0660(3) 0.2860(2) 0.22071(19) 0.0276(6) Uani 1 1 d . . . . .
H44 H -0.151657 0.246277 0.177279 0.033 Uiso 1 1 calc R U . . .
C26 C 0.0566(3) 0.7250(2) 0.52218(19) 0.0267(6) Uani 1 1 d . . . . .
H26A H -0.031735 0.683164 0.476452 0.032 Uiso 1 1 calc R U . . .
H26B H 0.057527 0.693950 0.564991 0.032 Uiso 1 1 calc R U . . .
C30 C 0.2015(3) 0.7758(2) 0.41331(19) 0.0276(6) Uani 1 1 d . . . . .
H30A H 0.299658 0.780286 0.385495 0.033 Uiso 1 1 calc R U . . .
H30B H 0.115411 0.732669 0.366534 0.033 Uiso 1 1 calc R U . . .
C27 C 0.0332(3) 0.8301(2) 0.5690(2) 0.0300(6) Uani 1 1 d . . . . .
H27A H -0.065563 0.825830 0.596244 0.036 Uiso 1 1 calc R U . . .
H27B H 0.119320 0.871469 0.616239 0.036 Uiso 1 1 calc R U . . .
C36 C 0.4883(3) 0.8410(2) 0.5335(2) 0.0306(6) Uani 1 1 d . . . . .
H36 H 0.490333 0.851575 0.480633 0.037 Uiso 1 1 calc R U . . .
C8 C 0.8468(3) 0.7813(2) 0.1430(2) 0.0263(6) Uani 1 1 d . . . . .
C7 C 0.7210(4) 0.7804(2) 0.28118(19) 0.0306(6) Uani 1 1 d . . . . .
H7A H 0.639260 0.739498 0.302034 0.037 Uiso 1 1 calc R U . . .
H7B H 0.823219 0.782945 0.307123 0.037 Uiso 1 1 calc R U . . .
C19 C 0.6506(3) 0.3012(2) 0.05851(19) 0.0279(6) Uani 1 1 d . . . . .
H19 H 0.718639 0.269213 0.020507 0.034 Uiso 1 1 calc R U . . .
C28 C 0.0286(4) 0.8791(2) 0.5052(2) 0.0325(7) Uani 1 1 d . . . . .
H28A H 0.020561 0.948609 0.537334 0.039 Uiso 1 1 calc R U . . .
H28B H -0.064556 0.842010 0.461861 0.039 Uiso 1 1 calc R U . . .
C3 C 0.5533(3) 0.7307(2) 0.1435(2) 0.0293(6) Uani 1 1 d . . . . .
H3A H 0.543500 0.698733 0.078578 0.035 Uiso 1 1 calc R U . . .
H3B H 0.468771 0.691058 0.163856 0.035 Uiso 1 1 calc R U . . .
C15 C 1.1383(3) 0.6110(2) 0.1426(2) 0.0321(7) Uani 1 1 d . . . . .
H15A H 1.166007 0.645484 0.206966 0.038 Uiso 1 1 calc R U . . .
H15B H 1.209607 0.648793 0.114476 0.038 Uiso 1 1 calc R U . . .
C38 C 0.6426(3) 0.6119(2) 0.4343(2) 0.0324(7) Uani 1 1 d . . . . .
H38A H 0.713950 0.651404 0.488992 0.039 Uiso 1 1 calc R U . . .
H38B H 0.668796 0.644937 0.392967 0.039 Uiso 1 1 calc R U . . .
C39 C 0.6631(3) 0.5075(2) 0.3944(2) 0.0334(7) Uani 1 1 d . . . . .
H39A H 0.605108 0.471888 0.335889 0.050 Uiso 1 1 calc R U . . .
H39B H 0.623738 0.471894 0.431739 0.050 Uiso 1 1 calc R U . . .
H39C H 0.773823 0.510486 0.389708 0.050 Uiso 1 1 calc R U . . .
C32 C 0.3535(4) 0.7721(2) 0.6282(2) 0.0324(7) Uani 1 1 d . . . . .
H32 H 0.262493 0.733842 0.640810 0.039 Uiso 1 1 calc R U . . .
C4 C 0.5343(4) 0.8376(2) 0.1723(2) 0.0357(7) Uani 1 1 d . . . . .
H4A H 0.615822 0.876715 0.149777 0.043 Uiso 1 1 calc R U . . .
H4B H 0.431624 0.835163 0.147030 0.043 Uiso 1 1 calc R U . . .
C9 C 0.8343(4) 0.7633(2) 0.0539(2) 0.0341(7) Uani 1 1 d . . . . .
H9 H 0.739314 0.723687 0.018340 0.041 Uiso 1 1 calc R U . . .
C6 C 0.7001(4) 0.8869(2) 0.3133(2) 0.0365(7) Uani 1 1 d . . . . .
H6A H 0.788554 0.930082 0.298622 0.044 Uiso 1 1 calc R U . . .
H6B H 0.700505 0.914527 0.377898 0.044 Uiso 1 1 calc R U . . .
C29 C 0.1753(4) 0.8806(2) 0.4569(2) 0.0311(6) Uani 1 1 d . . . . .
H29A H 0.164816 0.907143 0.411655 0.037 Uiso 1 1 calc R U . . .
H29B H 0.266760 0.925944 0.499187 0.037 Uiso 1 1 calc R U . . .
C5 C 0.5471(4) 0.8886(3) 0.2712(2) 0.0418(8) Uani 1 1 d . . . . .
H5A H 0.458054 0.854132 0.293092 0.050 Uiso 1 1 calc R U . . .
H5B H 0.542312 0.958842 0.288507 0.050 Uiso 1 1 calc R U . . .
C13 C 0.9876(3) 0.8402(2) 0.1936(2) 0.0351(7) Uani 1 1 d . . . . .
H13 H 0.999366 0.854018 0.254463 0.042 Uiso 1 1 calc R U . . .
C16 C 1.1566(4) 0.5064(3) 0.1116(2) 0.0347(7) Uani 1 1 d . . . . .
H16A H 1.116661 0.469709 0.049457 0.052 Uiso 1 1 calc R U . . .
H16B H 1.098145 0.472364 0.146046 0.052 Uiso 1 1 calc R U . . .
H16C H 1.267034 0.508659 0.119119 0.052 Uiso 1 1 calc R U . . .
C35 C 0.6210(4) 0.8833(2) 0.5940(2) 0.0397(8) Uani 1 1 d . . . . .
H35 H 0.712927 0.920745 0.581483 0.048 Uiso 1 1 calc R U . . .
C33 C 0.4848(4) 0.8155(3) 0.6893(2) 0.0411(8) Uani 1 1 d . . . . .
H33 H 0.482625 0.807201 0.743129 0.049 Uiso 1 1 calc R U . . .
C34 C 0.6190(4) 0.8710(3) 0.6716(2) 0.0434(9) Uani 1 1 d . . . . .
H34 H 0.709035 0.900272 0.713052 0.052 Uiso 1 1 calc R U . . .
C46 C -0.1120(4) 0.0744(3) 0.1580(2) 0.0409(8) Uani 1 1 d . . . . .
H46A H -0.131765 0.087416 0.106010 0.061 Uiso 1 1 calc R U . . .
H46B H -0.196975 0.085195 0.194981 0.061 Uiso 1 1 calc R U . . .
H46C H -0.105829 0.004976 0.139703 0.061 Uiso 1 1 calc R U . . .
C23 C 0.3738(4) 0.0815(3) 0.0592(2) 0.0389(8) Uani 1 1 d . . . . .
H23A H 0.375528 0.011063 0.030460 0.058 Uiso 1 1 calc R U . . .
H23B H 0.290448 0.093471 0.029126 0.058 Uiso 1 1 calc R U . . .
H23C H 0.355064 0.097029 0.120684 0.058 Uiso 1 1 calc R U . . .
C12 C 1.1123(4) 0.8793(3) 0.1548(3) 0.0494(10) Uani 1 1 d . . . . .
H12 H 1.207829 0.919366 0.189642 0.059 Uiso 1 1 calc R U . . .
C10 C 0.9586(5) 0.8025(3) 0.0163(3) 0.0487(10) Uani 1 1 d . . . . .
H10 H 0.947864 0.789475 -0.044424 0.058 Uiso 1 1 calc R U . . .
C11 C 1.0968(5) 0.8600(3) 0.0671(3) 0.0523(11) Uani 1 1 d . . . . .
H11 H 1.181786 0.886339 0.041379 0.063 Uiso 1 1 calc R U . . .
H1 H 0.569(5) 0.585(3) 0.225(3) 0.063 Uiso 1 1 d . U . . .
H2 H 0.072(5) 0.581(3) 0.333(3) 0.063 Uiso 1 1 d . 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
O5 C37 1.342(3) . ?
O5 C38 1.463(3) . ?
O1 C14 1.208(3) . ?
O2 C14 1.337(3) . ?
O2 C15 1.467(3) . ?
O4 C37 1.206(3) . ?
O6 C43 1.367(4) . ?
O6 C46 1.418(4) . ?
O3 C20 1.368(4) . ?
O3 C23 1.423(4) . ?
N2 C40 1.388(4) . ?
N2 C24 1.445(3) . ?
N1 C1 1.443(3) . ?
N1 C17 1.388(4) . ?
C43 C42 1.386(4) . ?
C43 C44 1.405(4) . ?
C40 C45 1.404(4) . ?
C40 C41 1.414(4) . ?
C37 C24 1.538(4) . ?
C22 C17 1.403(4) . ?
C22 C21 1.377(4) . ?
C45 C44 1.382(4) . ?
C25 C31 1.543(4) . ?
C25 C24 1.562(4) . ?
C25 C26 1.546(4) . ?
C25 C30 1.542(4) . ?
C14 C1 1.539(4) . ?
C1 C2 1.564(4) . ?
C17 C18 1.412(4) . ?
C21 C20 1.402(4) . ?
C18 C19 1.373(4) . ?
C41 C42 1.374(4) . ?
C31 C36 1.398(4) . ?
C31 C32 1.389(4) . ?
C2 C8 1.539(4) . ?
C2 C7 1.539(4) . ?
C2 C3 1.545(4) . ?
C20 C19 1.389(4) . ?
C26 C27 1.530(4) . ?
C30 C29 1.531(4) . ?
C27 C28 1.511(4) . ?
C36 C35 1.395(4) . ?
C8 C9 1.397(4) . ?
C8 C13 1.395(4) . ?
C7 C6 1.534(4) . ?
C28 C29 1.534(4) . ?
C3 C4 1.536(4) . ?
C15 C16 1.499(4) . ?
C38 C39 1.502(4) . ?
C32 C33 1.391(4) . ?
C4 C5 1.512(5) . ?
C9 C10 1.393(5) . ?
C6 C5 1.536(5) . ?
C13 C12 1.407(5) . ?
C35 C34 1.370(5) . ?
C33 C34 1.387(5) . ?
C12 C11 1.371(6) . ?
C10 C11 1.376(6) . ?

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
C37 O5 C38 119.3(2) . . ?
C14 O2 C15 118.7(2) . . ?
C43 O6 C46 117.8(2) . . ?
C20 O3 C23 116.8(2) . . ?
C40 N2 C24 120.6(2) . . ?
C17 N1 C1 120.8(2) . . ?
O6 C43 C42 116.8(3) . . ?
O6 C43 C44 124.8(3) . . ?
C42 C43 C44 118.3(3) . . ?
N2 C40 C45 120.4(2) . . ?
N2 C40 C41 123.0(3) . . ?
C45 C40 C41 116.6(3) . . ?
O5 C37 C24 110.2(2) . . ?
O4 C37 O5 125.1(2) . . ?
O4 C37 C24 124.7(2) . . ?
C21 C22 C17 122.3(3) . . ?
C44 C45 C40 122.3(3) . . ?
C31 C25 C24 106.2(2) . . ?
C31 C25 C26 111.1(2) . . ?
C26 C25 C24 107.6(2) . . ?
C30 C25 C31 112.8(2) . . ?
C30 C25 C24 112.4(2) . . ?
C30 C25 C26 106.7(2) . . ?
O1 C14 O2 124.9(2) . . ?
O1 C14 C1 124.6(2) . . ?
O2 C14 C1 110.5(2) . . ?
N1 C1 C14 111.6(2) . . ?
N1 C1 C2 113.3(2) . . ?
C14 C1 C2 110.0(2) . . ?
N1 C17 C22 120.1(2) . . ?
N1 C17 C18 123.2(2) . . ?
C22 C17 C18 116.7(3) . . ?
C22 C21 C20 120.1(3) . . ?
C19 C18 C17 121.1(3) . . ?
C42 C41 C40 121.1(3) . . ?
C36 C31 C25 122.1(3) . . ?
C32 C31 C25 120.3(3) . . ?
C32 C31 C36 117.5(3) . . ?
C8 C2 C1 105.9(2) . . ?
C8 C2 C7 112.7(2) . . ?
C8 C2 C3 111.0(2) . . ?
C7 C2 C1 112.4(2) . . ?
C7 C2 C3 106.9(2) . . ?
C3 C2 C1 107.9(2) . . ?
N2 C24 C37 112.0(2) . . ?
N2 C24 C25 113.3(2) . . ?
C37 C24 C25 109.9(2) . . ?
C41 C42 C43 121.7(3) . . ?
O3 C20 C21 124.5(3) . . ?
O3 C20 C19 117.2(3) . . ?
C19 C20 C21 118.3(3) . . ?
C45 C44 C43 120.0(3) . . ?
C27 C26 C25 111.8(2) . . ?
C29 C30 C25 112.4(2) . . ?
C28 C27 C26 110.7(2) . . ?
C35 C36 C31 121.2(3) . . ?
C9 C8 C2 119.7(3) . . ?
C13 C8 C2 122.1(3) . . ?
C13 C8 C9 118.0(3) . . ?
C6 C7 C2 112.7(2) . . ?
C18 C19 C20 121.6(3) . . ?
C27 C28 C29 111.0(2) . . ?
C4 C3 C2 112.0(2) . . ?
O2 C15 C16 110.1(2) . . ?
O5 C38 C39 109.9(2) . . ?
C31 C32 C33 121.4(3) . . ?
C5 C4 C3 110.7(3) . . ?
C10 C9 C8 121.3(3) . . ?
C7 C6 C5 111.5(3) . . ?
C30 C29 C28 111.5(3) . . ?
C4 C5 C6 111.1(3) . . ?
C8 C13 C12 120.2(3) . . ?
C34 C35 C36 120.2(3) . . ?
C34 C33 C32 120.1(3) . . ?
C35 C34 C33 119.6(3) . . ?
C11 C12 C13 120.5(3) . . ?
C11 C10 C9 119.9(4) . . ?
C12 C11 C10 120.1(3) . . ?

_olex2_exptl_crystal_mounting_method 'nylon loop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.662
_oxdiff_exptl_absorpt_empirical_full_min 0.428
