# Supplementary Information (SI) for Materials Advances.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2497318'
loop_
_audit_author_name
_audit_author_address
'Christopher Ziegler'
;University of Akron
United States of America
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.669(4)
_cell_length_b                   10.904(3)
_cell_length_c                   9.588(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.022(9)
_cell_angle_gamma                90
_cell_volume                     1499.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      24.82

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.228
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.318
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.234
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6489
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27525
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.419
_diffrn_reflns_theta_max         24.857
_diffrn_reflns_theta_full        24.857
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2575
_reflns_number_gt                2156
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0286P)²+1.3683P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2575
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0523
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1170
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1A C 0.9908(4) 0.1820(6) 0.7817(6) 0.0492(14) Uani 0.5 1 d . . P A 1
H1A H 0.957327 0.156433 0.693222 0.059 Uiso 0.5 1 calc R U P A 1
C1B C 0.9536(3) 0.1311(4) 0.8380(5) 0.0328(10) Uani 0.5 1 d . . P A 2
H1B H 0.900478 0.092952 0.786245 0.039 Uiso 0.5 1 calc R U P A 2
C2A C 1.0783(4) 0.1330(6) 0.8360(6) 0.0615(17) Uani 0.5 1 d . . P A 1
H2A H 1.103153 0.074266 0.784164 0.074 Uiso 0.5 1 calc R U P A 1
C2B C 1.0301(3) 0.0617(5) 0.8972(5) 0.0431(12) Uani 0.5 1 d . . P A 2
H2B H 1.028134 -0.022817 0.883750 0.052 Uiso 0.5 1 calc R U P A 2
C3A C 1.1273(6) 0.1704(9) 0.9632(10) 0.046(2) Uani 0.5 1 d . . P A 1
H3A H 1.186177 0.137730 0.998405 0.056 Uiso 0.5 1 calc R U P A 1
C3B C 1.1103(7) 0.1151(8) 0.9765(12) 0.054(3) Uani 0.5 1 d . . P A 2
H3B H 1.159880 0.067088 1.022570 0.065 Uiso 0.5 1 calc R U P A 2
C4A C 1.0906(5) 0.2582(7) 1.0436(7) 0.0431(17) Uani 0.5 1 d . . P A 1
H4A H 1.123020 0.281052 1.133785 0.052 Uiso 0.5 1 calc R U P A 1
C4B C 1.1143(5) 0.2459(8) 0.9852(8) 0.0399(16) Uani 0.5 1 d . . P A 2
H4B H 1.169986 0.284313 1.026745 0.048 Uiso 0.5 1 calc R U P A 2
C5A C 1.0062(4) 0.3092(5) 0.9857(6) 0.0315(12) Uani 0.5 1 d . . P A 1
H5A H 0.982856 0.372874 1.032526 0.038 Uiso 0.5 1 calc R U P A 1
C5B C 1.0365(4) 0.3153(5) 0.9327(6) 0.0341(12) Uani 0.5 1 d . . P A 2
H5B H 1.038885 0.399368 0.949655 0.041 Uiso 0.5 1 calc R U P A 2
C6 C 0.95475(14) 0.2651(2) 0.8557(2) 0.0286(5) Uani 1 1 d . . . . .
C7 C 0.86797(14) 0.33487(19) 0.7999(2) 0.0284(5) Uani 1 1 d . . . . .
C8 C 0.81298(13) 0.3077(2) 0.6577(2) 0.0281(5) Uani 1 1 d . . . . .
H8 H 0.828085 0.239544 0.608759 0.034 Uiso 1 1 calc R U . . .
C9 C 0.74109(13) 0.37910(19) 0.5961(2) 0.0262(5) Uani 1 1 d . . . . .
H9 H 0.728142 0.446546 0.648095 0.031 Uiso 1 1 calc R U . . .
C10 C 0.68265(13) 0.36139(19) 0.4585(2) 0.0278(5) Uani 1 1 d . . . . .
H10 H 0.695076 0.295712 0.403417 0.033 Uiso 1 1 calc R U . . .
C11 C 0.61045(13) 0.43546(19) 0.4050(2) 0.0256(5) Uani 1 1 d . . . . .
H11 H 0.603437 0.503808 0.459809 0.031 Uiso 1 1 calc R U . . .
C12 C 0.54219(13) 0.42230(18) 0.2727(2) 0.0244(4) Uani 1 1 d . . . . .
C13 C 0.46416(14) 0.49918(19) 0.2445(2) 0.0274(5) Uani 1 1 d . . . . .
H13 H 0.459727 0.562020 0.308312 0.033 Uiso 1 1 calc R U . . .
C14 C 0.39365(14) 0.4854(2) 0.1258(2) 0.0286(5) Uani 1 1 d . . . . .
H14 H 0.342599 0.537921 0.111777 0.034 Uiso 1 1 calc R U . . .
C15 C 0.39819(13) 0.39251(19) 0.0255(2) 0.0260(5) Uani 1 1 d . . . . .
C16 C 0.47845(13) 0.31805(19) 0.0503(2) 0.0278(5) Uani 1 1 d . . . . .
H16 H 0.484883 0.257903 -0.015726 0.033 Uiso 1 1 calc R U . . .
C17 C 0.54737(14) 0.33272(19) 0.1704(2) 0.0276(5) Uani 1 1 d . . . . .
H17 H 0.599116 0.281425 0.183944 0.033 Uiso 1 1 calc R U . . .
C18 C 0.25172(16) 0.4616(2) -0.1266(2) 0.0419(6) Uani 1 1 d . . . . .
H18A H 0.224682 0.475698 -0.045010 0.063 Uiso 1 1 calc R U . . .
H18B H 0.205005 0.430031 -0.203494 0.063 Uiso 1 1 calc R U . . .
H18C H 0.275656 0.537350 -0.155257 0.063 Uiso 1 1 calc R U . . .
C19 C 0.33559(16) 0.2817(2) -0.1956(2) 0.0418(6) Uani 1 1 d . . . . .
H19A H 0.386939 0.302085 -0.239073 0.063 Uiso 1 1 calc R U . . .
H19B H 0.279172 0.278953 -0.267300 0.063 Uiso 1 1 calc R U . . .
H19C H 0.346412 0.202953 -0.150271 0.063 Uiso 1 1 calc R U . . .
N1 N 0.32694(12) 0.37357(18) -0.09021(18) 0.0338(5) Uani 1 1 d . . . . .
O1 O 0.84500(14) 0.41636(18) 0.87266(18) 0.0634(6) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1A C6 1.327(5) . ?
C1A C2A 1.388(7) . ?
C1A H1A 0.9300 . ?
C1B C2B 1.375(6) . ?
C1B C6 1.470(5) . ?
C1B H1B 0.9300 . ?
C2A C3A 1.343(12) . ?
C2A H2A 0.9300 . ?
C2B C3B 1.388(11) . ?
C2B H2B 0.9300 . ?
C3A C4A 1.405(12) . ?
C3A H3A 0.9300 . ?
C3B C4B 1.430(11) . ?
C3B H3B 0.9300 . ?
C4A C5A 1.366(9) . ?
C4A H4A 0.9300 . ?
C4B C5B 1.375(10) . ?
C4B H4B 0.9300 . ?
C5A C6 1.401(6) . ?
C5A H5A 0.9300 . ?
C5B C6 1.384(6) . ?
C5B H5B 0.9300 . ?
C6 C7 1.484(3) . ?
C7 O1 1.220(3) . ?
C7 C8 1.463(3) . ?
C8 C9 1.344(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.429(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.346(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.450(3) . ?
C11 H11 0.9300 . ?
C12 C17 1.398(3) . ?
C12 C13 1.399(3) . ?
C13 C14 1.377(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.408(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.372(3) . ?
C15 C16 1.409(3) . ?
C16 C17 1.374(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 N1 1.449(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 N1 1.447(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1A C2A 120.2(4) . . ?
C6 C1A H1A 119.9 . . ?
C2A C1A H1A 119.9 . . ?
C2B C1B C6 120.7(4) . . ?
C2B C1B H1B 119.6 . . ?
C6 C1B H1B 119.6 . . ?
C3A C2A C1A 120.1(6) . . ?
C3A C2A H2A 119.9 . . ?
C1A C2A H2A 119.9 . . ?
C1B C2B C3B 121.4(6) . . ?
C1B C2B H2B 119.3 . . ?
C3B C2B H2B 119.3 . . ?
C2A C3A C4A 120.8(7) . . ?
C2A C3A H3A 119.6 . . ?
C4A C3A H3A 119.6 . . ?
C2B C3B C4B 118.1(8) . . ?
C2B C3B H3B 121.0 . . ?
C4B C3B H3B 121.0 . . ?
C5A C4A C3A 118.2(6) . . ?
C5A C4A H4A 120.9 . . ?
C3A C4A H4A 120.9 . . ?
C5B C4B C3B 120.4(7) . . ?
C5B C4B H4B 119.8 . . ?
C3B C4B H4B 119.8 . . ?
C4A C5A C6 119.8(5) . . ?
C4A C5A H5A 120.1 . . ?
C6 C5A H5A 120.1 . . ?
C4B C5B C6 122.6(5) . . ?
C4B C5B H5B 118.7 . . ?
C6 C5B H5B 118.7 . . ?
C1A C6 C5A 120.6(4) . . ?
C5B C6 C1B 116.3(3) . . ?
C1A C6 C7 124.4(3) . . ?
C5B C6 C7 124.9(3) . . ?
C5A C6 C7 114.0(3) . . ?
C1B C6 C7 118.6(2) . . ?
O1 C7 C8 121.08(19) . . ?
O1 C7 C6 119.08(19) . . ?
C8 C7 C6 119.82(18) . . ?
C9 C8 C7 121.47(19) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 126.3(2) . . ?
C8 C9 H9 116.8 . . ?
C10 C9 H9 116.8 . . ?
C11 C10 C9 123.0(2) . . ?
C11 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C10 C11 C12 128.26(19) . . ?
C10 C11 H11 115.9 . . ?
C12 C11 H11 115.9 . . ?
C17 C12 C13 116.41(18) . . ?
C17 C12 C11 123.69(18) . . ?
C13 C12 C11 119.86(18) . . ?
C14 C13 C12 122.53(19) . . ?
C14 C13 H13 118.7 . . ?
C12 C13 H13 118.7 . . ?
C13 C14 C15 120.57(19) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
N1 C15 C14 121.61(18) . . ?
N1 C15 C16 121.24(19) . . ?
C14 C15 C16 117.14(18) . . ?
C17 C16 C15 121.16(19) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C12 122.10(19) . . ?
C16 C17 H17 118.9 . . ?
C12 C17 H17 118.9 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 N1 C19 120.39(18) . . ?
C15 N1 C18 120.55(18) . . ?
C19 N1 C18 117.64(18) . . ?

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
C6 C1A C2A C3A -0.6(11) . . . . ?
C6 C1B C2B C3B 0.7(9) . . . . ?
C1A C2A C3A C4A 0.6(13) . . . . ?
C1B C2B C3B C4B -5.2(12) . . . . ?
C2A C3A C4A C5A -3.4(12) . . . . ?
C2B C3B C4B C5B 8.5(14) . . . . ?
C3A C4A C5A C6 6.0(10) . . . . ?
C3B C4B C5B C6 -7.5(12) . . . . ?
C2A C1A C6 C5A 3.3(9) . . . . ?
C2A C1A C6 C7 171.6(5) . . . . ?
C4B C5B C6 C1B 2.8(8) . . . . ?
C4B C5B C6 C7 178.2(5) . . . . ?
C4A C5A C6 C1A -6.1(8) . . . . ?
C4A C5A C6 C7 -175.6(5) . . . . ?
C2B C1B C6 C5B 0.6(7) . . . . ?
C2B C1B C6 C7 -175.1(4) . . . . ?
C1A C6 C7 O1 -174.0(4) . . . . ?
C5B C6 C7 O1 -38.6(4) . . . . ?
C5A C6 C7 O1 -5.0(4) . . . . ?
C1B C6 C7 O1 136.8(3) . . . . ?
C1A C6 C7 C8 4.1(5) . . . . ?
C5B C6 C7 C8 139.6(4) . . . . ?
C5A C6 C7 C8 173.2(3) . . . . ?
C1B C6 C7 C8 -45.1(4) . . . . ?
O1 C7 C8 C9 7.0(3) . . . . ?
C6 C7 C8 C9 -171.1(2) . . . . ?
C7 C8 C9 C10 -179.85(19) . . . . ?
C8 C9 C10 C11 178.5(2) . . . . ?
C9 C10 C11 C12 -174.9(2) . . . . ?
C10 C11 C12 C17 -6.8(3) . . . . ?
C10 C11 C12 C13 170.9(2) . . . . ?
C17 C12 C13 C14 2.7(3) . . . . ?
C11 C12 C13 C14 -175.19(19) . . . . ?
C12 C13 C14 C15 -0.8(3) . . . . ?
C13 C14 C15 N1 177.1(2) . . . . ?
C13 C14 C15 C16 -1.8(3) . . . . ?
N1 C15 C16 C17 -176.34(19) . . . . ?
C14 C15 C16 C17 2.5(3) . . . . ?
C15 C16 C17 C12 -0.7(3) . . . . ?
C13 C12 C17 C16 -1.9(3) . . . . ?
C11 C12 C17 C16 175.87(19) . . . . ?
C14 C15 N1 C19 176.7(2) . . . . ?
C16 C15 N1 C19 -4.4(3) . . . . ?
C14 C15 N1 C18 10.7(3) . . . . ?
C16 C15 N1 C18 -170.5(2) . . . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_1f
_database_code_depnum_ccdc_archive 'CCDC 2497323'
loop_
_audit_author_name
_audit_author_address
'Christopher Ziegler'
;University of Akron
United States of America
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H25 N O4'
_chemical_formula_weight         367.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

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                   7.8584(13)
_cell_length_b                   7.1808(14)
_cell_length_c                   35.233(7)
_cell_angle_alpha                90
_cell_angle_beta                 95.044(6)
_cell_angle_gamma                90
_cell_volume                     1980.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9048
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      28.34

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.532
_exptl_crystal_size_mid          0.492
_exptl_crystal_size_min          0.226
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6076
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            86772
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0809
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         2.321
_diffrn_reflns_theta_max         28.466
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4970
_reflns_number_gt                4029
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²+1.4063P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4970
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1239
_refine_ls_wR_factor_gt          0.1111
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.28008(17) 0.3988(2) 0.46515(4) 0.0236(3) Uani 1 1 d . . . . .
C2 C 0.18732(17) 0.5580(2) 0.45375(4) 0.0251(3) Uani 1 1 d . . . . .
H2 H 0.076481 0.574640 0.460456 0.030 Uiso 1 1 calc R U . . .
C3 C 0.26340(17) 0.6908(2) 0.43227(4) 0.0232(3) Uani 1 1 d . . . . .
C4 C 0.43171(17) 0.66890(19) 0.42257(4) 0.0218(3) Uani 1 1 d . . . . .
C5 C 0.51989(16) 0.50844(19) 0.43468(4) 0.0219(3) Uani 1 1 d . . . . .
C6 C 0.44642(17) 0.3721(2) 0.45611(4) 0.0230(3) Uani 1 1 d . . . . .
H6 H 0.507307 0.266075 0.464137 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2832(2) 0.1054(2) 0.49642(4) 0.0328(3) Uani 1 1 d . . . . .
H7A H 0.323089 0.047191 0.474325 0.049 Uiso 1 1 calc R U . . .
H7B H 0.207717 0.022084 0.508070 0.049 Uiso 1 1 calc R U . . .
H7C H 0.378920 0.134490 0.514270 0.049 Uiso 1 1 calc R U . . .
C8 C 0.0067(2) 0.8682(3) 0.42473(6) 0.0426(4) Uani 1 1 d . . . . .
H8A H -0.057635 0.764385 0.413980 0.064 Uiso 1 1 calc R U . . .
H8B H -0.036660 0.981395 0.413028 0.064 Uiso 1 1 calc R U . . .
H8C H -0.003685 0.873537 0.451660 0.064 Uiso 1 1 calc R U . . .
C9 C 0.77926(18) 0.3341(2) 0.43510(5) 0.0307(3) Uani 1 1 d . . . . .
H9A H 0.887060 0.338618 0.424252 0.046 Uiso 1 1 calc R U . . .
H9B H 0.716600 0.226429 0.425669 0.046 Uiso 1 1 calc R U . . .
H9C H 0.798444 0.326885 0.462344 0.046 Uiso 1 1 calc R U . . .
C10 C 0.51621(17) 0.8170(2) 0.40107(4) 0.0240(3) Uani 1 1 d . . . . .
C11 C 0.58360(18) 0.7660(2) 0.36492(4) 0.0260(3) Uani 1 1 d . . . . .
H11 H 0.558830 0.649365 0.354364 0.031 Uiso 1 1 calc R U . . .
C12 C 0.68030(18) 0.8851(2) 0.34691(4) 0.0262(3) Uani 1 1 d . . . . .
H12 H 0.700042 1.001308 0.358080 0.031 Uiso 1 1 calc R U . . .
C13 C 0.75632(18) 0.8503(2) 0.31199(4) 0.0273(3) Uani 1 1 d . . . . .
H13 H 0.730355 0.740467 0.298719 0.033 Uiso 1 1 calc R U . . .
C14 C 0.86444(18) 0.9731(2) 0.29802(4) 0.0279(3) Uani 1 1 d . . . . .
H14 H 0.884339 1.081767 0.312070 0.033 Uiso 1 1 calc R U . . .
C15 C 0.95380(18) 0.9573(2) 0.26380(4) 0.0265(3) Uani 1 1 d . . . . .
C16 C 1.07127(19) 1.0942(2) 0.25538(4) 0.0303(3) Uani 1 1 d . . . . .
H16 H 1.087346 1.196386 0.271510 0.036 Uiso 1 1 calc R U . . .
C17 C 1.16426(19) 1.0831(2) 0.22398(4) 0.0309(3) Uani 1 1 d . . . . .
H17 H 1.241119 1.177273 0.219390 0.037 Uiso 1 1 calc R U . . .
C18 C 1.14397(18) 0.9313(2) 0.19892(4) 0.0278(3) Uani 1 1 d . . . . .
C19 C 1.02248(19) 0.7945(2) 0.20668(4) 0.0303(3) Uani 1 1 d . . . . .
H19 H 1.003643 0.694006 0.190208 0.036 Uiso 1 1 calc R U . . .
C20 C 0.93153(19) 0.8078(2) 0.23825(4) 0.0295(3) Uani 1 1 d . . . . .
H20 H 0.853210 0.714978 0.242744 0.035 Uiso 1 1 calc R U . . .
C21 C 1.3747(2) 1.0464(3) 0.16325(5) 0.0420(4) Uani 1 1 d . . . . .
H21A H 1.328086 1.169634 0.160206 0.063 Uiso 1 1 calc R U . . .
H21B H 1.430656 1.013539 0.141043 0.063 Uiso 1 1 calc R U . . .
H21C H 1.455738 1.042974 0.185270 0.063 Uiso 1 1 calc R U . . .
C22 C 1.2169(2) 0.7571(3) 0.14275(5) 0.0406(4) Uani 1 1 d . . . . .
H22A H 1.250952 0.645673 0.156419 0.061 Uiso 1 1 calc R U . . .
H22B H 1.286214 0.773408 0.121888 0.061 Uiso 1 1 calc R U . . .
H22C H 1.099063 0.747225 0.133129 0.061 Uiso 1 1 calc R U . . .
N1 N 1.23843(18) 0.9155(2) 0.16809(4) 0.0342(3) Uani 1 1 d . . . . .
O1 O 0.19389(13) 0.27276(16) 0.48538(3) 0.0311(2) Uani 1 1 d . . . . .
O2 O 0.18178(13) 0.84661(15) 0.41811(3) 0.0301(2) Uani 1 1 d . . . . .
O3 O 0.68372(12) 0.49791(15) 0.42474(3) 0.0283(2) Uani 1 1 d . . . . .
O4 O 0.52811(15) 0.97533(15) 0.41390(3) 0.0319(2) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.3676(17) . ?
C1 C6 1.3856(19) . ?
C1 C2 1.396(2) . ?
C2 C3 1.385(2) . ?
C2 H2 0.9300 . ?
C3 O2 1.3623(17) . ?
C3 C4 1.4037(19) . ?
C4 C5 1.3921(19) . ?
C4 C10 1.4945(19) . ?
C5 O3 1.3658(16) . ?
C5 C6 1.3923(19) . ?
C6 H6 0.9300 . ?
C7 O1 1.4283(19) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O2 1.4242(19) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O3 1.4257(18) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O4 1.2243(18) . ?
C10 C11 1.4681(19) . ?
C11 C12 1.340(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.436(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.348(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.452(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.398(2) . ?
C15 C20 1.402(2) . ?
C16 C17 1.381(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.403(2) . ?
C17 H17 0.9300 . ?
C18 N1 1.3732(19) . ?
C18 C19 1.413(2) . ?
C19 C20 1.377(2) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 N1 1.446(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 N1 1.446(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 123.29(13) . . ?
O1 C1 C2 114.95(12) . . ?
C6 C1 C2 121.76(13) . . ?
C3 C2 C1 118.78(13) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
O2 C3 C2 123.60(13) . . ?
O2 C3 C4 115.23(13) . . ?
C2 C3 C4 121.14(13) . . ?
C5 C4 C3 118.19(13) . . ?
C5 C4 C10 120.85(12) . . ?
C3 C4 C10 120.92(13) . . ?
O3 C5 C4 114.98(12) . . ?
O3 C5 C6 123.05(12) . . ?
C4 C5 C6 121.95(12) . . ?
C1 C6 C5 118.17(13) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 H9A 109.5 . . ?
O3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C10 C11 122.02(13) . . ?
O4 C10 C4 119.78(13) . . ?
C11 C10 C4 118.20(12) . . ?
C12 C11 C10 120.97(14) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 126.19(14) . . ?
C11 C12 H12 116.9 . . ?
C13 C12 H12 116.9 . . ?
C14 C13 C12 121.47(14) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C13 C14 C15 128.21(15) . . ?
C13 C14 H14 115.9 . . ?
C15 C14 H14 115.9 . . ?
C16 C15 C20 116.72(13) . . ?
C16 C15 C14 119.85(14) . . ?
C20 C15 C14 123.42(14) . . ?
C17 C16 C15 122.38(15) . . ?
C17 C16 H16 118.8 . . ?
C15 C16 H16 118.8 . . ?
C16 C17 C18 120.66(14) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
N1 C18 C17 121.52(14) . . ?
N1 C18 C19 121.11(14) . . ?
C17 C18 C19 117.37(14) . . ?
C20 C19 C18 121.05(14) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C15 121.80(14) . . ?
C19 C20 H20 119.1 . . ?
C15 C20 H20 119.1 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 N1 C22 120.76(14) . . ?
C18 N1 C21 119.78(14) . . ?
C22 N1 C21 119.08(14) . . ?
C1 O1 C7 116.39(11) . . ?
C3 O2 C8 117.40(13) . . ?
C5 O3 C9 117.84(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -178.35(12) . . . . ?
C6 C1 C2 C3 1.1(2) . . . . ?
C1 C2 C3 O2 176.70(12) . . . . ?
C1 C2 C3 C4 -1.2(2) . . . . ?
O2 C3 C4 C5 -177.17(12) . . . . ?
C2 C3 C4 C5 0.88(19) . . . . ?
O2 C3 C4 C10 5.04(18) . . . . ?
C2 C3 C4 C10 -176.90(12) . . . . ?
C3 C4 C5 O3 -179.01(12) . . . . ?
C10 C4 C5 O3 -1.23(18) . . . . ?
C3 C4 C5 C6 -0.51(19) . . . . ?
C10 C4 C5 C6 177.27(12) . . . . ?
O1 C1 C6 C5 178.68(12) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
O3 C5 C6 C1 178.83(12) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C5 C4 C10 O4 -120.77(15) . . . . ?
C3 C4 C10 O4 56.95(19) . . . . ?
C5 C4 C10 C11 58.91(17) . . . . ?
C3 C4 C10 C11 -123.37(14) . . . . ?
O4 C10 C11 C12 8.6(2) . . . . ?
C4 C10 C11 C12 -171.03(13) . . . . ?
C10 C11 C12 C13 178.60(13) . . . . ?
C11 C12 C13 C14 -173.80(15) . . . . ?
C12 C13 C14 C15 178.71(14) . . . . ?
C13 C14 C15 C16 -175.29(15) . . . . ?
C13 C14 C15 C20 3.6(2) . . . . ?
C20 C15 C16 C17 -1.2(2) . . . . ?
C14 C15 C16 C17 177.70(14) . . . . ?
C15 C16 C17 C18 0.0(2) . . . . ?
C16 C17 C18 N1 -178.30(14) . . . . ?
C16 C17 C18 C19 1.5(2) . . . . ?
N1 C18 C19 C20 178.01(14) . . . . ?
C17 C18 C19 C20 -1.8(2) . . . . ?
C18 C19 C20 C15 0.6(2) . . . . ?
C16 C15 C20 C19 0.9(2) . . . . ?
C14 C15 C20 C19 -177.96(14) . . . . ?
C17 C18 N1 C22 179.45(15) . . . . ?
C19 C18 N1 C22 -0.4(2) . . . . ?
C17 C18 N1 C21 6.6(2) . . . . ?
C19 C18 N1 C21 -173.18(15) . . . . ?
C6 C1 O1 C7 -1.5(2) . . . . ?
C2 C1 O1 C7 178.02(12) . . . . ?
C2 C3 O2 C8 -2.6(2) . . . . ?
C4 C3 O2 C8 175.41(13) . . . . ?
C4 C5 O3 C9 -177.84(12) . . . . ?
C6 C5 O3 C9 3.68(19) . . . . ?

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 2497320'
loop_
_audit_author_name
_audit_author_address
'Christopher Ziegler'
;University of Akron
United States of America
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H22 Cl3 N O2'
_chemical_formula_weight         426.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   10.719(3)
_cell_length_b                   26.404(6)
_cell_length_c                   7.2837(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2061.5(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9827
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      26.35

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_F_000             888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.252
_exptl_crystal_size_mid          0.236
_exptl_crystal_size_min          0.086
_exptl_absorpt_coefficient_mu    0.461
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6378
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23412
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.050
_diffrn_reflns_theta_max         26.453
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4162
_reflns_number_gt                3476
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.824
_reflns_Friedel_fraction_max     0.962
_reflns_Friedel_fraction_full    0.980

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0036P)²+1.9199P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1401 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.04(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4162
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0749
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_restrained_S_all      1.173
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1374(4) 0.07742(15) 0.2334(7) 0.0250(9) Uani 1 1 d . . . . .
C2 C 0.2476(4) 0.08395(16) 0.3325(7) 0.0259(9) Uani 1 1 d . . . . .
H2 H 0.286779 0.056438 0.387525 0.031 Uiso 1 1 calc R U . . .
C3 C 0.2978(4) 0.13228(16) 0.3474(7) 0.0254(9) Uani 1 1 d . . . . .
H3 H 0.372272 0.136656 0.411100 0.031 Uiso 1 1 calc R U . . .
C4 C 0.2397(4) 0.17452(16) 0.2696(6) 0.0233(9) Uani 1 1 d . . . . .
C5 C 0.1310(4) 0.16661(17) 0.1680(6) 0.0252(10) Uani 1 1 d . . . . .
H5 H 0.091456 0.194015 0.112781 0.030 Uiso 1 1 calc R U . . .
C6 C 0.0814(4) 0.11869(16) 0.1484(6) 0.0259(10) Uani 1 1 d . . . . .
H6 H 0.009989 0.113979 0.077952 0.031 Uiso 1 1 calc R U . . .
C7 C 0.1273(5) -0.01071(17) 0.3078(8) 0.0414(14) Uani 1 1 d . . . . .
H7A H 0.210785 -0.016917 0.265670 0.062 Uiso 1 1 calc R U . . .
H7B H 0.076462 -0.039881 0.283497 0.062 Uiso 1 1 calc R U . . .
H7C H 0.128446 -0.004147 0.437420 0.062 Uiso 1 1 calc R U . . .
C8 C 0.2957(4) 0.22539(17) 0.2914(6) 0.0247(10) Uani 1 1 d . . . . .
C9 C 0.2186(4) 0.27054(16) 0.2598(6) 0.0263(10) Uani 1 1 d . . . . .
H9 H 0.134158 0.266378 0.234950 0.032 Uiso 1 1 calc R U . . .
C10 C 0.2658(4) 0.31759(17) 0.2654(6) 0.0254(10) Uani 1 1 d . . . . .
H10 H 0.351227 0.320542 0.285362 0.031 Uiso 1 1 calc R U . . .
C11 C 0.1968(4) 0.36375(16) 0.2436(7) 0.0265(10) Uani 1 1 d . . . . .
H11 H 0.112684 0.361834 0.213249 0.032 Uiso 1 1 calc R U . . .
C12 C 0.2490(4) 0.40968(17) 0.2654(6) 0.0261(10) Uani 1 1 d . . . . .
H12 H 0.334200 0.409823 0.289455 0.031 Uiso 1 1 calc R U . . .
C13 C 0.1895(4) 0.45926(16) 0.2562(6) 0.0247(9) Uani 1 1 d . . . . .
C14 C 0.2543(4) 0.50232(17) 0.3162(6) 0.0272(10) Uani 1 1 d . . . . .
H14 H 0.336030 0.498692 0.357046 0.033 Uiso 1 1 calc R U . . .
C15 C 0.2009(4) 0.55001(17) 0.3168(6) 0.0278(10) Uani 1 1 d . . . . .
H15 H 0.246466 0.577552 0.359639 0.033 Uiso 1 1 calc R U . . .
C16 C 0.0779(4) 0.55722(15) 0.2529(6) 0.0241(9) Uani 1 1 d . . . . .
C17 C 0.0130(4) 0.51412(16) 0.1893(6) 0.0248(10) Uani 1 1 d . . . . .
H17 H -0.067915 0.517641 0.145201 0.030 Uiso 1 1 calc R U . . .
C18 C 0.0678(4) 0.46693(16) 0.1916(6) 0.0260(10) Uani 1 1 d . . . . .
H18 H 0.022556 0.439273 0.148960 0.031 Uiso 1 1 calc R U . . .
C19 C 0.0900(5) 0.64739(17) 0.3340(8) 0.0410(13) Uani 1 1 d . . . . .
H19A H 0.101269 0.641110 0.462774 0.062 Uiso 1 1 calc R U . . .
H19B H 0.041824 0.677710 0.317623 0.062 Uiso 1 1 calc R U . . .
H19C H 0.169947 0.651426 0.276466 0.062 Uiso 1 1 calc R U . . .
C20 C -0.1083(4) 0.61074(17) 0.2239(8) 0.0359(11) Uani 1 1 d . . . . .
H20A H -0.133579 0.591938 0.117385 0.054 Uiso 1 1 calc R U . . .
H20B H -0.127562 0.645925 0.206519 0.054 Uiso 1 1 calc R U . . .
H20C H -0.151903 0.598249 0.329690 0.054 Uiso 1 1 calc R U . . .
C21 C 0.4836(4) 0.29919(16) 0.6685(6) 0.0270(10) Uani 1 1 d . . . . .
H21 H 0.446101 0.284220 0.558498 0.032 Uiso 1 1 calc R U . . .
Cl1 Cl 0.62418(10) 0.26727(4) 0.71722(16) 0.0315(3) Uani 1 1 d . . . . .
Cl2 Cl 0.51339(12) 0.36399(4) 0.62645(19) 0.0387(3) Uani 1 1 d . . . . .
Cl3 Cl 0.37877(9) 0.29263(4) 0.85311(17) 0.0318(3) Uani 1 1 d . . . . .
N1 N 0.0248(3) 0.60489(13) 0.2510(6) 0.0305(9) Uani 1 1 d . . . . .
O1 O 0.0770(3) 0.03219(11) 0.2137(5) 0.0312(7) Uani 1 1 d . . . . .
O2 O 0.4058(3) 0.22950(11) 0.3433(5) 0.0308(7) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.366(5) . ?
C1 C6 1.390(6) . ?
C1 C2 1.394(6) . ?
C2 C3 1.389(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.398(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(6) . ?
C4 C8 1.480(6) . ?
C5 C6 1.380(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.429(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O2 1.244(5) . ?
C8 C9 1.468(6) . ?
C9 C10 1.342(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.435(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.345(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.458(6) . ?
C12 H12 0.9300 . ?
C13 C18 1.402(6) . ?
C13 C14 1.402(6) . ?
C14 C15 1.383(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.411(6) . ?
C15 H15 0.9300 . ?
C16 N1 1.382(5) . ?
C16 C17 1.412(6) . ?
C17 C18 1.377(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 N1 1.454(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N1 1.448(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 Cl3 1.761(4) . ?
C21 Cl1 1.762(4) . ?
C21 Cl2 1.767(4) . ?
C21 H21 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
O1 C1 C6 115.7(4) . . ?
O1 C1 C2 124.3(4) . . ?
C6 C1 C2 120.0(4) . . ?
C3 C2 C1 118.8(4) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 121.9(4) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 117.9(4) . . ?
C5 C4 C8 122.1(4) . . ?
C3 C4 C8 120.0(4) . . ?
C6 C5 C4 120.9(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 120.4(4) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C9 120.7(4) . . ?
O2 C8 C4 119.8(4) . . ?
C9 C8 C4 119.5(4) . . ?
C10 C9 C8 122.3(4) . . ?
C10 C9 H9 118.8 . . ?
C8 C9 H9 118.8 . . ?
C9 C10 C11 126.1(4) . . ?
C9 C10 H10 117.0 . . ?
C11 C10 H10 117.0 . . ?
C12 C11 C10 122.6(4) . . ?
C12 C11 H11 118.7 . . ?
C10 C11 H11 118.7 . . ?
C11 C12 C13 128.5(4) . . ?
C11 C12 H12 115.7 . . ?
C13 C12 H12 115.7 . . ?
C18 C13 C14 116.6(4) . . ?
C18 C13 C12 123.5(4) . . ?
C14 C13 C12 119.8(4) . . ?
C15 C14 C13 122.3(4) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C14 C15 C16 120.6(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
N1 C16 C15 120.8(4) . . ?
N1 C16 C17 121.9(4) . . ?
C15 C16 C17 117.4(4) . . ?
C18 C17 C16 121.0(4) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C13 122.1(4) . . ?
C17 C18 H18 118.9 . . ?
C13 C18 H18 118.9 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
Cl3 C21 Cl1 110.2(2) . . ?
Cl3 C21 Cl2 110.0(2) . . ?
Cl1 C21 Cl2 110.1(2) . . ?
Cl3 C21 H21 108.8 . . ?
Cl1 C21 H21 108.8 . . ?
Cl2 C21 H21 108.8 . . ?
C16 N1 C20 120.3(3) . . ?
C16 N1 C19 120.1(4) . . ?
C20 N1 C19 116.6(4) . . ?
C1 O1 C7 117.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -177.9(4) . . . . ?
C6 C1 C2 C3 1.4(7) . . . . ?
C1 C2 C3 C4 1.4(7) . . . . ?
C2 C3 C4 C5 -2.7(7) . . . . ?
C2 C3 C4 C8 179.1(4) . . . . ?
C3 C4 C5 C6 1.2(6) . . . . ?
C8 C4 C5 C6 179.4(4) . . . . ?
C4 C5 C6 C1 1.5(7) . . . . ?
O1 C1 C6 C5 176.5(4) . . . . ?
C2 C1 C6 C5 -2.9(7) . . . . ?
C5 C4 C8 O2 -162.8(4) . . . . ?
C3 C4 C8 O2 15.4(6) . . . . ?
C5 C4 C8 C9 20.1(6) . . . . ?
C3 C4 C8 C9 -161.8(4) . . . . ?
O2 C8 C9 C10 7.4(7) . . . . ?
C4 C8 C9 C10 -175.5(4) . . . . ?
C8 C9 C10 C11 -177.3(4) . . . . ?
C9 C10 C11 C12 174.6(5) . . . . ?
C10 C11 C12 C13 -176.8(4) . . . . ?
C11 C12 C13 C18 -11.1(8) . . . . ?
C11 C12 C13 C14 168.1(5) . . . . ?
C18 C13 C14 C15 1.6(7) . . . . ?
C12 C13 C14 C15 -177.6(4) . . . . ?
C13 C14 C15 C16 -1.1(7) . . . . ?
C14 C15 C16 N1 -179.2(4) . . . . ?
C14 C15 C16 C17 0.0(7) . . . . ?
N1 C16 C17 C18 179.8(4) . . . . ?
C15 C16 C17 C18 0.6(6) . . . . ?
C16 C17 C18 C13 -0.1(7) . . . . ?
C14 C13 C18 C17 -1.0(7) . . . . ?
C12 C13 C18 C17 178.2(4) . . . . ?
C15 C16 N1 C20 -166.6(5) . . . . ?
C17 C16 N1 C20 14.3(7) . . . . ?
C15 C16 N1 C19 -6.9(7) . . . . ?
C17 C16 N1 C19 174.0(5) . . . . ?
C6 C1 O1 C7 -176.4(4) . . . . ?
C2 C1 O1 C7 3.0(7) . . . . ?

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.071

####################################################################### 
# 
# 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_1d
_database_code_depnum_ccdc_archive 'CCDC 2497321'
loop_
_audit_author_name
_audit_author_address
'Christopher Ziegler'
;University of Akron
United States of America
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 N O3'
_chemical_formula_weight         337.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.280(2)
_cell_length_b                   13.278(3)
_cell_length_c                   11.121(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.359(8)
_cell_angle_gamma                90
_cell_volume                     1813.4(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9799
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      26.46

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.608
_exptl_crystal_size_mid          0.159
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6311
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31563
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.658
_diffrn_reflns_theta_max         26.458
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3724
_reflns_number_gt                3010
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0345P)²+0.8267P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3724
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0938
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.58933(12) 0.80126(11) 0.99877(13) 0.0249(3) Uani 1 1 d . . . . .
C2 C 0.57251(12) 0.69999(11) 1.02400(13) 0.0262(3) Uani 1 1 d . . . . .
H007 H 0.609594 0.668372 1.086641 0.031 Uiso 1 1 calc R U . . .
C3 C 0.49914(12) 0.64781(11) 0.95330(13) 0.0253(3) Uani 1 1 d . . . . .
H008 H 0.488118 0.579909 0.969759 0.030 Uiso 1 1 calc R U . . .
C4 C 0.44050(11) 0.69075(11) 0.85865(12) 0.0220(3) Uani 1 1 d . . . . .
C5 C 0.45577(11) 0.79530(11) 0.83900(12) 0.0219(3) Uani 1 1 d . . . . .
C6 C 0.53081(11) 0.84893(11) 0.90722(13) 0.0247(3) Uani 1 1 d . . . . .
H00K H 0.542158 0.916957 0.891853 0.030 Uiso 1 1 calc R U . . .
C7 C 0.71969(13) 0.81799(13) 1.15797(14) 0.0327(4) Uani 1 1 d . . . . .
H00P H 0.760924 0.761173 1.130401 0.049 Uiso 1 1 calc R U . . .
H00Q H 0.669089 0.796429 1.218172 0.049 Uiso 1 1 calc R U . . .
H00R H 0.768213 0.867277 1.191745 0.049 Uiso 1 1 calc R U . . .
C8 C 0.40030(13) 0.94566(11) 0.73668(14) 0.0303(3) Uani 1 1 d . . . . .
H00A H 0.350586 0.966523 0.674542 0.045 Uiso 1 1 calc R U . . .
H00H H 0.473396 0.961867 0.713475 0.045 Uiso 1 1 calc R U . . .
H00I H 0.383106 0.979977 0.810130 0.045 Uiso 1 1 calc R U . . .
C9 C 0.36845(11) 0.62155(11) 0.78743(13) 0.0240(3) Uani 1 1 d . . . . .
C10 C 0.33056(11) 0.64841(11) 0.66605(13) 0.0248(3) Uani 1 1 d . . . . .
H00B H 0.353771 0.708435 0.631569 0.030 Uiso 1 1 calc R U . . .
C11 C 0.26284(11) 0.58772(11) 0.60381(13) 0.0256(3) Uani 1 1 d . . . . .
H00C H 0.244125 0.526334 0.638237 0.031 Uiso 1 1 calc R U . . .
C12 C 0.21759(12) 0.61139(12) 0.48791(13) 0.0257(3) Uani 1 1 d . . . . .
H00J H 0.239906 0.670324 0.450189 0.031 Uiso 1 1 calc R U . . .
C13 C 0.14419(11) 0.55224(11) 0.43099(13) 0.0252(3) Uani 1 1 d . . . . .
H00D H 0.127768 0.491411 0.468142 0.030 Uiso 1 1 calc R U . . .
C14 C 0.08787(11) 0.57281(11) 0.31819(13) 0.0241(3) Uani 1 1 d . . . . .
C15 C 0.00079(12) 0.51175(11) 0.28140(13) 0.0261(3) Uani 1 1 d . . . . .
H00E H -0.015887 0.455042 0.326776 0.031 Uiso 1 1 calc R U . . .
C16 C -0.06118(12) 0.53245(11) 0.18051(13) 0.0269(3) Uani 1 1 d . . . . .
H00F H -0.118549 0.490027 0.159756 0.032 Uiso 1 1 calc R U . . .
C17 C -0.03855(12) 0.61716(11) 0.10854(13) 0.0251(3) Uani 1 1 d . . . . .
C18 C 0.05247(12) 0.67659(11) 0.14232(13) 0.0274(3) Uani 1 1 d . . . . .
H00G H 0.071881 0.731377 0.094977 0.033 Uiso 1 1 calc R U . . .
C19 C 0.11272(12) 0.65484(11) 0.24380(13) 0.0261(3) Uani 1 1 d . . . . .
H00L H 0.171626 0.695740 0.263638 0.031 Uiso 1 1 calc R U . . .
C20 C -0.18318(12) 0.57172(12) -0.03430(14) 0.0303(3) Uani 1 1 d . . . . .
H00M H -0.146778 0.516209 -0.072037 0.045 Uiso 1 1 calc R U . . .
H00N H -0.229201 0.604881 -0.092073 0.045 Uiso 1 1 calc R U . . .
H00O H -0.226642 0.547258 0.030945 0.045 Uiso 1 1 calc R U . . .
C21 C -0.06679(16) 0.72016(14) -0.07111(16) 0.0451(5) Uani 1 1 d . . . . .
H00S H -0.053600 0.781404 -0.027516 0.068 Uiso 1 1 calc R U . . .
H00T H -0.122061 0.731550 -0.131009 0.068 Uiso 1 1 calc R U . . .
H00U H -0.000840 0.698866 -0.109400 0.068 Uiso 1 1 calc R U . . .
N1 N -0.10292(11) 0.64249(10) 0.01149(11) 0.0308(3) Uani 1 1 d . . . . .
O1 O 0.66131(9) 0.86138(8) 1.05896(10) 0.0322(3) Uani 1 1 d . . . . .
O2 O 0.39105(8) 0.83923(7) 0.75440(9) 0.0252(2) Uani 1 1 d . . . . .
O3 O 0.34518(9) 0.53883(8) 0.83114(10) 0.0324(3) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.3636(18) . ?
C1 C2 1.389(2) . ?
C1 C6 1.394(2) . ?
C2 C3 1.379(2) . ?
C2 H007 0.9300 . ?
C3 C4 1.394(2) . ?
C3 H008 0.9300 . ?
C4 C5 1.418(2) . ?
C4 C9 1.499(2) . ?
C5 O2 1.3592(17) . ?
C5 C6 1.387(2) . ?
C6 H00K 0.9300 . ?
C7 O1 1.4313(18) . ?
C7 H00P 0.9600 . ?
C7 H00Q 0.9600 . ?
C7 H00R 0.9600 . ?
C8 O2 1.4316(17) . ?
C8 H00A 0.9600 . ?
C8 H00H 0.9600 . ?
C8 H00I 0.9600 . ?
C9 O3 1.2354(18) . ?
C9 C10 1.469(2) . ?
C10 C11 1.346(2) . ?
C10 H00B 0.9300 . ?
C11 C12 1.435(2) . ?
C11 H00C 0.9300 . ?
C12 C13 1.350(2) . ?
C12 H00J 0.9300 . ?
C13 C14 1.455(2) . ?
C13 H00D 0.9300 . ?
C14 C15 1.401(2) . ?
C14 C19 1.403(2) . ?
C15 C16 1.380(2) . ?
C15 H00E 0.9300 . ?
C16 C17 1.409(2) . ?
C16 H00F 0.9300 . ?
C17 N1 1.3756(19) . ?
C17 C18 1.417(2) . ?
C18 C19 1.376(2) . ?
C18 H00G 0.9300 . ?
C19 H00L 0.9300 . ?
C20 N1 1.452(2) . ?
C20 H00M 0.9600 . ?
C20 H00N 0.9600 . ?
C20 H00O 0.9600 . ?
C21 N1 1.452(2) . ?
C21 H00S 0.9600 . ?
C21 H00T 0.9600 . ?
C21 H00U 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 124.35(13) . . ?
O1 C1 C6 114.98(13) . . ?
C2 C1 C6 120.68(13) . . ?
C3 C2 C1 117.94(13) . . ?
C3 C2 H007 121.0 . . ?
C1 C2 H007 121.0 . . ?
C2 C3 C4 123.90(14) . . ?
C2 C3 H008 118.0 . . ?
C4 C3 H008 118.0 . . ?
C3 C4 C5 116.67(13) . . ?
C3 C4 C9 116.67(13) . . ?
C5 C4 C9 126.66(13) . . ?
O2 C5 C6 122.82(13) . . ?
O2 C5 C4 116.71(12) . . ?
C6 C5 C4 120.42(13) . . ?
C5 C6 C1 120.27(14) . . ?
C5 C6 H00K 119.9 . . ?
C1 C6 H00K 119.9 . . ?
O1 C7 H00P 109.5 . . ?
O1 C7 H00Q 109.5 . . ?
H00P C7 H00Q 109.5 . . ?
O1 C7 H00R 109.5 . . ?
H00P C7 H00R 109.5 . . ?
H00Q C7 H00R 109.5 . . ?
O2 C8 H00A 109.5 . . ?
O2 C8 H00H 109.5 . . ?
H00A C8 H00H 109.5 . . ?
O2 C8 H00I 109.5 . . ?
H00A C8 H00I 109.5 . . ?
H00H C8 H00I 109.5 . . ?
O3 C9 C10 120.31(13) . . ?
O3 C9 C4 118.32(13) . . ?
C10 C9 C4 121.29(12) . . ?
C11 C10 C9 121.21(14) . . ?
C11 C10 H00B 119.4 . . ?
C9 C10 H00B 119.4 . . ?
C10 C11 C12 124.41(14) . . ?
C10 C11 H00C 117.8 . . ?
C12 C11 H00C 117.8 . . ?
C13 C12 C11 123.18(14) . . ?
C13 C12 H00J 118.4 . . ?
C11 C12 H00J 118.4 . . ?
C12 C13 C14 127.42(14) . . ?
C12 C13 H00D 116.3 . . ?
C14 C13 H00D 116.3 . . ?
C15 C14 C19 116.47(13) . . ?
C15 C14 C13 120.08(13) . . ?
C19 C14 C13 123.40(13) . . ?
C16 C15 C14 122.58(14) . . ?
C16 C15 H00E 118.7 . . ?
C14 C15 H00E 118.7 . . ?
C15 C16 C17 120.75(14) . . ?
C15 C16 H00F 119.6 . . ?
C17 C16 H00F 119.6 . . ?
N1 C17 C16 121.77(13) . . ?
N1 C17 C18 121.35(13) . . ?
C16 C17 C18 116.87(13) . . ?
C19 C18 C17 121.31(14) . . ?
C19 C18 H00G 119.3 . . ?
C17 C18 H00G 119.3 . . ?
C18 C19 C14 121.93(14) . . ?
C18 C19 H00L 119.0 . . ?
C14 C19 H00L 119.0 . . ?
N1 C20 H00M 109.5 . . ?
N1 C20 H00N 109.5 . . ?
H00M C20 H00N 109.5 . . ?
N1 C20 H00O 109.5 . . ?
H00M C20 H00O 109.5 . . ?
H00N C20 H00O 109.5 . . ?
N1 C21 H00S 109.5 . . ?
N1 C21 H00T 109.5 . . ?
H00S C21 H00T 109.5 . . ?
N1 C21 H00U 109.5 . . ?
H00S C21 H00U 109.5 . . ?
H00T C21 H00U 109.5 . . ?
C17 N1 C20 120.16(13) . . ?
C17 N1 C21 119.58(13) . . ?
C20 N1 C21 116.57(13) . . ?
C1 O1 C7 117.52(12) . . ?
C5 O2 C8 118.19(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -178.20(13) . . . . ?
C6 C1 C2 C3 2.1(2) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 C5 -2.5(2) . . . . ?
C2 C3 C4 C9 177.01(13) . . . . ?
C3 C4 C5 O2 -173.89(12) . . . . ?
C9 C4 C5 O2 6.6(2) . . . . ?
C3 C4 C5 C6 3.8(2) . . . . ?
C9 C4 C5 C6 -175.68(13) . . . . ?
O2 C5 C6 C1 175.28(12) . . . . ?
C4 C5 C6 C1 -2.3(2) . . . . ?
O1 C1 C6 C5 179.48(12) . . . . ?
C2 C1 C6 C5 -0.8(2) . . . . ?
C3 C4 C9 O3 16.48(19) . . . . ?
C5 C4 C9 O3 -164.05(14) . . . . ?
C3 C4 C9 C10 -160.42(13) . . . . ?
C5 C4 C9 C10 19.1(2) . . . . ?
O3 C9 C10 C11 5.5(2) . . . . ?
C4 C9 C10 C11 -177.71(13) . . . . ?
C9 C10 C11 C12 176.35(13) . . . . ?
C10 C11 C12 C13 -175.43(14) . . . . ?
C11 C12 C13 C14 175.22(13) . . . . ?
C12 C13 C14 C15 -169.22(14) . . . . ?
C12 C13 C14 C19 7.9(2) . . . . ?
C19 C14 C15 C16 -2.7(2) . . . . ?
C13 C14 C15 C16 174.59(13) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C16 C17 N1 -176.27(14) . . . . ?
C15 C16 C17 C18 2.4(2) . . . . ?
N1 C17 C18 C19 175.84(14) . . . . ?
C16 C17 C18 C19 -2.8(2) . . . . ?
C17 C18 C19 C14 0.5(2) . . . . ?
C15 C14 C19 C18 2.3(2) . . . . ?
C13 C14 C19 C18 -174.94(14) . . . . ?
C16 C17 N1 C20 -12.4(2) . . . . ?
C18 C17 N1 C20 168.97(13) . . . . ?
C16 C17 N1 C21 -170.04(15) . . . . ?
C18 C17 N1 C21 11.4(2) . . . . ?
C2 C1 O1 C7 -2.9(2) . . . . ?
C6 C1 O1 C7 176.86(12) . . . . ?
C6 C5 O2 C8 -0.84(19) . . . . ?
C4 C5 O2 C8 176.78(13) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_1e
_database_code_depnum_ccdc_archive 'CCDC 2497322'
loop_
_audit_author_name
_audit_author_address
'Christopher Ziegler'
;University of Akron
United States of America
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H23 N O3'
_chemical_formula_weight         337.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   6.4711(10)
_cell_length_b                   37.579(6)
_cell_length_c                   7.3111(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1777.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9808
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      28.26

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.633
_exptl_crystal_size_mid          0.427
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5120
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37508
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0921
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_k_max       50
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.168
_diffrn_reflns_theta_max         28.264
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_point_group_measured_fraction_full 0.938
_reflns_number_total             3984
_reflns_number_gt                3312
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.683
_reflns_Friedel_fraction_max     0.796
_reflns_Friedel_fraction_full    0.867

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0360P)²+0.9903P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1176 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.7(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3984
_refine_ls_number_parameters     230
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1162
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8231(5) 0.72075(8) 0.2537(5) 0.0352(7) Uani 1 1 d . . . . .
H1 H 0.776402 0.734791 0.157456 0.042 Uiso 1 1 calc R U . . .
C2 C 0.9868(5) 0.69770(8) 0.2234(5) 0.0332(7) Uani 1 1 d . . . . .
H2 H 1.050112 0.696235 0.109396 0.040 Uiso 1 1 calc R U . . .
C3 C 1.0535(5) 0.67674(7) 0.3699(5) 0.0304(7) Uani 1 1 d . . . . .
C4 C 0.9566(5) 0.67840(7) 0.5391(5) 0.0288(6) Uani 1 1 d . . . . .
C5 C 0.7931(5) 0.70216(8) 0.5659(5) 0.0308(7) Uani 1 1 d . . . . .
C6 C 0.7265(5) 0.72364(8) 0.4223(5) 0.0338(7) Uani 1 1 d . . . . .
H6 H 0.618734 0.739688 0.439226 0.041 Uiso 1 1 calc R U . . .
C7 C 1.3614(5) 0.65839(9) 0.2162(5) 0.0403(8) Uani 1 1 d . . . . .
H7A H 1.299079 0.652886 0.100443 0.060 Uiso 1 1 calc R U . . .
H7B H 1.478258 0.643130 0.235764 0.060 Uiso 1 1 calc R U . . .
H7C H 1.405855 0.682763 0.216468 0.060 Uiso 1 1 calc R U . . .
C8 C 0.5359(5) 0.72425(9) 0.7704(6) 0.0439(9) Uani 1 1 d . . . . .
H8A H 0.430018 0.718293 0.683666 0.066 Uiso 1 1 calc R U . . .
H8B H 0.572479 0.748869 0.757007 0.066 Uiso 1 1 calc R U . . .
H8C H 0.485808 0.720118 0.892116 0.066 Uiso 1 1 calc R U . . .
C9 C 1.0274(4) 0.65446(8) 0.6918(4) 0.0303(6) Uani 1 1 d . . . . .
C10 C 0.9204(5) 0.62075(8) 0.7169(4) 0.0304(6) Uani 1 1 d . . . . .
H10 H 0.988716 0.603065 0.782111 0.036 Uiso 1 1 calc R U . . .
C11 C 0.7303(5) 0.61313(7) 0.6532(4) 0.0285(6) Uani 1 1 d . . . . .
H11 H 0.659267 0.630762 0.589803 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6311(4) 0.57923(7) 0.6778(4) 0.0285(6) Uani 1 1 d . . . . .
H12 H 0.701164 0.561707 0.742699 0.034 Uiso 1 1 calc R U . . .
C13 C 0.4426(4) 0.57153(7) 0.6120(4) 0.0269(6) Uani 1 1 d . . . . .
H13 H 0.370338 0.590090 0.557308 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3398(4) 0.53705(7) 0.6174(4) 0.0243(6) Uani 1 1 d . . . . .
C15 C 0.4330(4) 0.50630(7) 0.6882(4) 0.0258(6) Uani 1 1 d . . . . .
H15 H 0.564011 0.507904 0.739706 0.031 Uiso 1 1 calc R U . . .
C16 C 0.3352(4) 0.47385(7) 0.6831(4) 0.0257(6) Uani 1 1 d . . . . .
H16 H 0.401989 0.454049 0.731338 0.031 Uiso 1 1 calc R U . . .
C17 C 0.1373(4) 0.46977(7) 0.6071(4) 0.0226(6) Uani 1 1 d . . . . .
C18 C 0.0407(4) 0.50066(8) 0.5402(4) 0.0270(6) Uani 1 1 d . . . . .
H18 H -0.091870 0.499238 0.491711 0.032 Uiso 1 1 calc R U . . .
C19 C 0.1404(4) 0.53293(7) 0.5458(4) 0.0273(6) Uani 1 1 d . . . . .
H19 H 0.072717 0.552874 0.500209 0.033 Uiso 1 1 calc R U . . .
C20 C 0.1515(5) 0.40573(7) 0.6649(5) 0.0322(7) Uani 1 1 d . . . . .
H20A H 0.285691 0.404133 0.609545 0.048 Uiso 1 1 calc R U . . .
H20B H 0.073415 0.384724 0.636438 0.048 Uiso 1 1 calc R U . . .
H20C H 0.166212 0.407783 0.795132 0.048 Uiso 1 1 calc R U . . .
C21 C -0.1789(4) 0.43379(8) 0.5797(5) 0.0321(7) Uani 1 1 d . . . . .
H21A H -0.240959 0.438934 0.696031 0.048 Uiso 1 1 calc R U . . .
H21B H -0.214823 0.410059 0.543008 0.048 Uiso 1 1 calc R U . . .
H21C H -0.228403 0.450424 0.490200 0.048 Uiso 1 1 calc R U . . .
N1 N 0.0444(3) 0.43677(6) 0.5948(4) 0.0275(5) Uani 1 1 d . . . . .
O1 O 1.2142(4) 0.65305(6) 0.3587(3) 0.0376(5) Uani 1 1 d . . . . .
O2 O 0.7140(3) 0.70258(6) 0.7380(3) 0.0365(5) Uani 1 1 d . . . . .
O3 O 1.1767(4) 0.66264(6) 0.7852(4) 0.0469(6) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.386(5) . ?
C1 C2 1.386(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.398(4) . ?
C2 H2 0.9300 . ?
C3 O1 1.371(4) . ?
C3 C4 1.388(5) . ?
C4 C5 1.398(4) . ?
C4 C9 1.506(4) . ?
C5 O2 1.359(4) . ?
C5 C6 1.393(4) . ?
C6 H6 0.9300 . ?
C7 O1 1.426(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O2 1.431(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O3 1.222(4) . ?
C9 C10 1.455(4) . ?
C10 C11 1.346(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.438(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.343(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.457(4) . ?
C13 H13 0.9300 . ?
C14 C19 1.400(4) . ?
C14 C15 1.402(4) . ?
C15 C16 1.374(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.405(4) . ?
C16 H16 0.9300 . ?
C17 N1 1.381(3) . ?
C17 C18 1.406(4) . ?
C18 C19 1.374(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 N1 1.450(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N1 1.454(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.4(3) . . ?
C6 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C1 C2 C3 117.7(3) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
O1 C3 C4 115.1(3) . . ?
O1 C3 C2 123.7(3) . . ?
C4 C3 C2 121.2(3) . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 C9 119.8(3) . . ?
C5 C4 C9 120.5(3) . . ?
O2 C5 C6 125.1(3) . . ?
O2 C5 C4 115.0(3) . . ?
C6 C5 C4 119.9(3) . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 C10 121.7(3) . . ?
O3 C9 C4 120.3(3) . . ?
C10 C9 C4 117.9(3) . . ?
C11 C10 C9 125.2(3) . . ?
C11 C10 H10 117.4 . . ?
C9 C10 H10 117.4 . . ?
C10 C11 C12 123.6(3) . . ?
C10 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C13 C12 C11 123.5(3) . . ?
C13 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
C12 C13 C14 126.6(3) . . ?
C12 C13 H13 116.7 . . ?
C14 C13 H13 116.7 . . ?
C19 C14 C15 116.3(2) . . ?
C19 C14 C13 120.6(2) . . ?
C15 C14 C13 123.1(3) . . ?
C16 C15 C14 121.6(3) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C15 C16 C17 121.8(2) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
N1 C17 C16 121.4(2) . . ?
N1 C17 C18 121.7(3) . . ?
C16 C17 C18 116.9(2) . . ?
C19 C18 C17 120.6(3) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C18 C19 C14 122.8(3) . . ?
C18 C19 H19 118.6 . . ?
C14 C19 H19 118.6 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 N1 C20 119.4(2) . . ?
C17 N1 C21 120.4(2) . . ?
C20 N1 C21 116.1(2) . . ?
C3 O1 C7 117.3(2) . . ?
C5 O2 C8 117.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.3(4) . . . . ?
C1 C2 C3 O1 -179.6(3) . . . . ?
C1 C2 C3 C4 1.3(4) . . . . ?
O1 C3 C4 C5 178.9(3) . . . . ?
C2 C3 C4 C5 -1.9(4) . . . . ?
O1 C3 C4 C9 -1.5(4) . . . . ?
C2 C3 C4 C9 177.7(3) . . . . ?
C3 C4 C5 O2 -177.8(3) . . . . ?
C9 C4 C5 O2 2.6(4) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C9 C4 C5 C6 -178.7(3) . . . . ?
C2 C1 C6 C5 -1.3(5) . . . . ?
O2 C5 C6 C1 179.2(3) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C3 C4 C9 O3 82.5(4) . . . . ?
C5 C4 C9 O3 -97.9(4) . . . . ?
C3 C4 C9 C10 -94.2(3) . . . . ?
C5 C4 C9 C10 85.5(4) . . . . ?
O3 C9 C10 C11 163.4(3) . . . . ?
C4 C9 C10 C11 -20.1(5) . . . . ?
C9 C10 C11 C12 178.8(3) . . . . ?
C10 C11 C12 C13 -179.1(3) . . . . ?
C11 C12 C13 C14 174.3(3) . . . . ?
C12 C13 C14 C19 178.9(3) . . . . ?
C12 C13 C14 C15 -2.9(5) . . . . ?
C19 C14 C15 C16 1.5(4) . . . . ?
C13 C14 C15 C16 -176.8(3) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C15 C16 C17 N1 176.9(3) . . . . ?
C15 C16 C17 C18 -1.6(4) . . . . ?
N1 C17 C18 C19 -176.8(3) . . . . ?
C16 C17 C18 C19 1.7(4) . . . . ?
C17 C18 C19 C14 -0.2(5) . . . . ?
C15 C14 C19 C18 -1.4(4) . . . . ?
C13 C14 C19 C18 176.9(3) . . . . ?
C16 C17 N1 C20 1.2(4) . . . . ?
C18 C17 N1 C20 179.6(3) . . . . ?
C16 C17 N1 C21 157.7(3) . . . . ?
C18 C17 N1 C21 -23.9(4) . . . . ?
C4 C3 O1 C7 -159.1(3) . . . . ?
C2 C3 O1 C7 21.7(4) . . . . ?
C6 C5 O2 C8 6.3(4) . . . . ?
C4 C5 O2 C8 -175.1(3) . . . . ?

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 2497319'
loop_
_audit_author_name
_audit_author_address
'Christopher Ziegler'
;University of Akron
United States of America
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.38

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.727(2)
_cell_length_b                   13.395(4)
_cell_length_c                   31.495(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3259.8(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9051
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      26.41

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.446
_exptl_crystal_size_mid          0.312
_exptl_crystal_size_min          0.228
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6016
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            107477
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0864
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.936
_diffrn_reflns_theta_max         26.458
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3350
_reflns_number_gt                2887
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0321P)²+2.4918P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3350
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1610(2) 0.85095(11) 0.20449(5) 0.0244(3) Uani 1 1 d . . . . .
H1 H 1.207109 0.914794 0.207011 0.029 Uiso 1 1 calc R U . . .
C2 C 0.9888(2) 0.83421(11) 0.21519(5) 0.0248(3) Uani 1 1 d . . . . .
H2 H 0.920083 0.886143 0.225194 0.030 Uiso 1 1 calc R U . . .
C3 C 0.9211(2) 0.73895(11) 0.21072(5) 0.0233(3) Uani 1 1 d . . . . .
H3 H 0.806208 0.727363 0.217972 0.028 Uiso 1 1 calc R U . . .
C4 C 1.02157(19) 0.66007(11) 0.19560(4) 0.0195(3) Uani 1 1 d . . . . .
C5 C 1.19693(19) 0.67794(11) 0.18595(4) 0.0198(3) Uani 1 1 d . . . . .
C6 C 1.2645(2) 0.77357(11) 0.19010(5) 0.0233(3) Uani 1 1 d . . . . .
H6 H 1.379663 0.785686 0.183197 0.028 Uiso 1 1 calc R U . . .
C7 C 1.47771(19) 0.60499(12) 0.17885(5) 0.0270(3) Uani 1 1 d . . . . .
H7A H 1.522940 0.652666 0.158979 0.040 Uiso 1 1 calc R U . . .
H7B H 1.529752 0.541007 0.173796 0.040 Uiso 1 1 calc R U . . .
H7C H 1.503541 0.626346 0.207245 0.040 Uiso 1 1 calc R U . . .
C8 C 0.93743(19) 0.55978(11) 0.19132(5) 0.0207(3) Uani 1 1 d . . . . .
C9 C 0.97000(19) 0.50276(11) 0.15232(5) 0.0219(3) Uani 1 1 d . . . . .
H9 H 1.051579 0.526828 0.133174 0.026 Uiso 1 1 calc R U . . .
C10 C 0.88693(19) 0.41715(11) 0.14307(5) 0.0218(3) Uani 1 1 d . . . . .
H10 H 0.810592 0.392006 0.163238 0.026 Uiso 1 1 calc R U . . .
C11 C 0.90753(19) 0.36169(11) 0.10427(5) 0.0224(3) Uani 1 1 d . . . . .
H11 H 0.983801 0.385894 0.083882 0.027 Uiso 1 1 calc R U . . .
C12 C 0.82168(19) 0.27651(11) 0.09611(5) 0.0216(3) Uani 1 1 d . . . . .
H12 H 0.750461 0.252808 0.117676 0.026 Uiso 1 1 calc R U . . .
C13 C 0.82730(19) 0.21704(11) 0.05740(5) 0.0206(3) Uani 1 1 d . . . . .
C14 C 0.7547(2) 0.12140(11) 0.05655(5) 0.0234(3) Uani 1 1 d . . . . .
H14 H 0.705128 0.096075 0.081207 0.028 Uiso 1 1 calc R U . . .
C15 C 0.7541(2) 0.06319(11) 0.02025(5) 0.0230(3) Uani 1 1 d . . . . .
H15 H 0.706855 -0.000632 0.021177 0.028 Uiso 1 1 calc R U . . .
C16 C 0.82424(19) 0.09945(11) -0.01819(5) 0.0209(3) Uani 1 1 d . . . . .
C17 C 0.8999(2) 0.19532(11) -0.01722(5) 0.0234(3) Uani 1 1 d . . . . .
H17 H 0.949469 0.221073 -0.041797 0.028 Uiso 1 1 calc R U . . .
C18 C 0.90189(19) 0.25155(11) 0.01945(5) 0.0227(3) Uani 1 1 d . . . . .
H18 H 0.954080 0.314106 0.019056 0.027 Uiso 1 1 calc R U . . .
C19 C 0.7676(2) -0.05977(11) -0.05339(5) 0.0264(3) Uani 1 1 d . . . . .
H19A H 0.837956 -0.093562 -0.032782 0.040 Uiso 1 1 calc R U . . .
H19B H 0.785049 -0.089463 -0.080803 0.040 Uiso 1 1 calc R U . . .
H19C H 0.647981 -0.065517 -0.045547 0.040 Uiso 1 1 calc R U . . .
C20 C 0.8941(2) 0.08245(13) -0.09366(5) 0.0332(4) Uani 1 1 d . . . . .
H20A H 0.855040 0.149431 -0.098733 0.050 Uiso 1 1 calc R U . . .
H20B H 0.861292 0.040709 -0.117092 0.050 Uiso 1 1 calc R U . . .
H20C H 1.017765 0.082101 -0.090750 0.050 Uiso 1 1 calc R U . . .
N1 N 0.81579(18) 0.04484(10) -0.05497(4) 0.0254(3) Uani 1 1 d . . . . .
O1 O 1.29356(13) 0.59744(8) 0.17365(3) 0.0238(2) Uani 1 1 d . . . . .
O2 O 0.83382(14) 0.53143(8) 0.21846(3) 0.0265(3) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.386(2) . ?
C1 C2 1.391(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.386(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.395(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.409(2) . ?
C4 C8 1.499(2) . ?
C5 O1 1.3677(17) . ?
C5 C6 1.390(2) . ?
C6 H6 0.9300 . ?
C7 O1 1.4358(18) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O2 1.2311(18) . ?
C8 C9 1.468(2) . ?
C9 C10 1.346(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.439(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.345(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.457(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.399(2) . ?
C13 C18 1.405(2) . ?
C14 C15 1.384(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.413(2) . ?
C15 H15 0.9300 . ?
C16 N1 1.3716(19) . ?
C16 C17 1.411(2) . ?
C17 C18 1.379(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 N1 1.451(2) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 N1 1.451(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.75(14) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 118.98(14) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.48(14) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 118.68(14) . . ?
C3 C4 C8 117.93(13) . . ?
C5 C4 C8 123.38(13) . . ?
O1 C5 C6 123.25(13) . . ?
O1 C5 C4 116.88(13) . . ?
C6 C5 C4 119.86(14) . . ?
C1 C6 C5 120.21(14) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
O1 C7 H7A 109.5 . . ?
O1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 C9 122.13(14) . . ?
O2 C8 C4 119.75(13) . . ?
C9 C8 C4 117.86(13) . . ?
C10 C9 C8 122.85(14) . . ?
C10 C9 H9 118.6 . . ?
C8 C9 H9 118.6 . . ?
C9 C10 C11 124.81(14) . . ?
C9 C10 H10 117.6 . . ?
C11 C10 H10 117.6 . . ?
C12 C11 C10 123.09(14) . . ?
C12 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C11 C12 C13 127.53(14) . . ?
C11 C12 H12 116.2 . . ?
C13 C12 H12 116.2 . . ?
C14 C13 C18 116.71(13) . . ?
C14 C13 C12 120.32(13) . . ?
C18 C13 C12 122.96(13) . . ?
C15 C14 C13 122.23(14) . . ?
C15 C14 H14 118.9 . . ?
C13 C14 H14 118.9 . . ?
C14 C15 C16 120.87(14) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
N1 C16 C17 121.56(13) . . ?
N1 C16 C15 121.48(14) . . ?
C17 C16 C15 116.95(13) . . ?
C18 C17 C16 121.32(14) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C13 121.88(14) . . ?
C17 C18 H18 119.1 . . ?
C13 C18 H18 119.1 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 N1 C19 119.90(13) . . ?
C16 N1 C20 120.28(13) . . ?
C19 N1 C20 118.12(13) . . ?
C5 O1 C7 116.95(12) . . ?

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
C6 C1 C2 C3 -0.9(2) . . . . ?
C1 C2 C3 C4 -0.3(2) . . . . ?
C2 C3 C4 C5 1.9(2) . . . . ?
C2 C3 C4 C8 -179.33(13) . . . . ?
C3 C4 C5 O1 176.20(13) . . . . ?
C8 C4 C5 O1 -2.5(2) . . . . ?
C3 C4 C5 C6 -2.4(2) . . . . ?
C8 C4 C5 C6 178.93(13) . . . . ?
C2 C1 C6 C5 0.4(2) . . . . ?
O1 C5 C6 C1 -177.20(13) . . . . ?
C4 C5 C6 C1 1.3(2) . . . . ?
C3 C4 C8 O2 -38.8(2) . . . . ?
C5 C4 C8 O2 139.88(15) . . . . ?
C3 C4 C8 C9 135.41(14) . . . . ?
C5 C4 C8 C9 -45.89(19) . . . . ?
O2 C8 C9 C10 1.4(2) . . . . ?
C4 C8 C9 C10 -172.64(13) . . . . ?
C8 C9 C10 C11 176.41(14) . . . . ?
C9 C10 C11 C12 -179.76(15) . . . . ?
C10 C11 C12 C13 177.19(14) . . . . ?
C11 C12 C13 C14 168.65(15) . . . . ?
C11 C12 C13 C18 -12.2(2) . . . . ?
C18 C13 C14 C15 -0.6(2) . . . . ?
C12 C13 C14 C15 178.68(14) . . . . ?
C13 C14 C15 C16 -1.5(2) . . . . ?
C14 C15 C16 N1 -176.28(14) . . . . ?
C14 C15 C16 C17 2.4(2) . . . . ?
N1 C16 C17 C18 177.37(14) . . . . ?
C15 C16 C17 C18 -1.3(2) . . . . ?
C16 C17 C18 C13 -0.8(2) . . . . ?
C14 C13 C18 C17 1.7(2) . . . . ?
C12 C13 C18 C17 -177.54(14) . . . . ?
C17 C16 N1 C19 168.37(14) . . . . ?
C15 C16 N1 C19 -13.1(2) . . . . ?
C17 C16 N1 C20 3.5(2) . . . . ?
C15 C16 N1 C20 -177.91(15) . . . . ?
C6 C5 O1 C7 20.9(2) . . . . ?
C4 C5 O1 C7 -157.65(13) . . . . ?

_refine_diff_density_max         0.239
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.044

