# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_2
_database_code_depnum_ccdc_archive 'CCDC 2212061'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-10-10 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;
_audit_creation_date             2022-10-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H34 N2 O4'
_chemical_formula_sum            'C31 H34 N2 O4'
_chemical_formula_weight         498.60
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        C2/m
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'
'-x, -y, -z'
'-x, y, -z'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   6.690(3)
_cell_length_b                   9.570(4)
_cell_length_c                   21.704(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.203(11)
_cell_angle_gamma                90
_cell_volume                     1383.8(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    517
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.00
_cell_measurement_theta_min      40.80
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7060
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.138
_diffrn_reflns_theta_min         4.091
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device       'AFC12: Kappa 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P100K'
_diffrn_measurement_method       ω
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_type              'Rigaku MM-007HF'
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1155
_reflns_number_total             1294
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2015)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_refine_diff_density_max         0.659
_refine_diff_density_min         -0.967
_refine_diff_density_rms         0.199
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         1294
_refine_ls_number_restraints     120
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.1316
_refine_ls_restrained_S_all      1.972
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3936
_refine_ls_wR_factor_ref         0.4012
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C10-C11 = C11-C12 = C12-C13 = C10A-C11A = C11A-C12A = C12A-C13A = C13A-C14 =
 C14-C15 = C15-C10A
 1.39 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C11 \\sim C11A \\sim C15: within 2.5A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2.5A
C12 \\sim C12A \\sim C14: within 2.5A with sigma of 0.04 and sigma for terminal
atoms of 0.08 within 2.5A
4. Rigid body (RIGU) restrains
 O8, O9, C3, C8, C10, C11, C12, C13, C8A, C9, C10A, C11A, C12A, C13A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O8(0.25) O9(0.25) C8(0.25) C10(0.25) C11(0.5) H11(0.5) C12(0.5)
 H12(0.5) C13(0.25) C8A(0.25) C9(0.25) C10A(0.25) C11A(0.25) H11A(0.25)
 C12A(0.25) H12A(0.25) C13A(0.25) C14(0.25) H14(0.25) C15(0.25) H15(0.25)
6.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C11(H11), C12(H12), C11A(H11A), C12A(H12A), C14(H14), C15(H15)
6.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5971(5) 0.500000 0.89579(16) 0.0572(12) Uani 1 2 d S T P . .
O8 O 0.1922(10) 0.500000 0.6724(3) 0.077(3) Uani 0.5 2 d S T P A 1
O9 O -0.1016(12) 0.500000 0.7148(4) 0.061(2) Uani 0.5 2 d S T P A 1
N1 N 0.4230(5) 0.500000 0.86615(15) 0.0436(11) Uani 1 2 d S T P A .
C2 C 0.3991(6) 0.500000 0.79840(18) 0.0426(12) Uani 1 2 d S T P A .
C3 C 0.1739(7) 0.500000 0.7878(2) 0.0470(13) Uani 1 2 d S T P . .
C4 C 0.0869(7) 0.500000 0.8394(2) 0.0498(13) Uani 1 2 d S T P . .
H4 H -0.054627 0.500000 0.840860 0.060 Uiso 1 2 calc R U P . .
C5 C 0.2327(7) 0.500000 0.8959(2) 0.0454(12) Uani 1 2 d S T P . .
C6 C 0.4935(6) 0.3685(4) 0.77401(17) 0.0606(12) Uani 1 1 d . . . . .
H6A H 0.638397 0.369413 0.785774 0.091 Uiso 1 1 calc R U . A .
H6B H 0.468870 0.365655 0.728825 0.091 Uiso 1 1 calc R U . . .
H6C H 0.433805 0.285910 0.791755 0.091 Uiso 1 1 calc R U . . .
C7 C 0.2207(7) 0.3683(4) 0.93523(19) 0.0639(12) Uani 1 1 d . . . . .
H7A H 0.244432 0.285908 0.910082 0.096 Uiso 1 1 calc R U . . .
H7B H 0.087230 0.361860 0.950258 0.096 Uiso 1 1 calc R U . . .
H7C H 0.322738 0.372654 0.970545 0.096 Uiso 1 1 calc R U . . .
C8 C 0.101(2) 0.500000 0.7188(6) 0.042(3) Uani 0.5 2 d S T P A 1
C10 C -0.2036(18) 0.500000 0.6553(5) 0.056(3) Uani 0.5 2 d DS T P A 1
C11 C -0.2721(15) 0.3774(7) 0.6241(3) 0.069(2) Uani 0.5 1 d D U P A 1
H11 H -0.232784 0.289823 0.641923 0.082 Uiso 0.5 1 calc R U P A 1
C12 C -0.3938(15) 0.3778(7) 0.5689(4) 0.073(2) Uani 0.5 1 d D U P A 1
H12 H -0.439480 0.291641 0.551020 0.088 Uiso 0.5 1 calc R U P A 1
C13 C -0.449(2) 0.500000 0.5400(8) 0.064(3) Uani 0.5 2 d DS T P A 1
C8A C 0.045(2) 0.500000 0.7338(7) 0.047(3) Uani 0.5 2 d S T P A 2
C9 C -0.0489(18) 0.500000 0.6830(7) 0.065(3) Uani 0.5 2 d S T P A 2
C10A C -0.168(2) 0.500000 0.6253(7) 0.082(4) Uani 0.5 2 d DS T P A 2
C11A C -0.085(3) 0.500000 0.5693(7) 0.132(7) Uani 0.5 2 d DS TU P A 2
H11A H 0.056668 0.500000 0.569271 0.158 Uiso 0.5 2 calc R U P A 2
C12A C -0.202(2) 0.500000 0.5133(9) 0.134(7) Uani 0.5 2 d DS TU P A 2
H12A H -0.137920 0.500000 0.475928 0.160 Uiso 0.5 2 calc R U P A 2
C13A C -0.411(2) 0.500000 0.5106(8) 0.074(4) Uani 0.5 2 d DS T P A 2
C14 C -0.488(4) 0.500000 0.5677(9) 0.156(11) Uani 0.5 2 d DS TU P A 2
H14 H -0.629508 0.500000 0.567949 0.187 Uiso 0.5 2 calc R U P A 2
C15 C -0.375(3) 0.500000 0.6243(13) 0.181(11) Uani 0.5 2 d DS TU P A 2
H15 H -0.438372 0.500000 0.661716 0.218 Uiso 0.5 2 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.278(4) . ?
O8 C8 1.222(16) . ?
O9 C8 1.353(16) . ?
O9 C10 1.405(12) . ?
N1 C2 1.465(5) . ?
N1 C5 1.479(6) . ?
C2 C3 1.503(6) . ?
C2 C6 1.524(4) . ?
C2 C6 1.524(4) 2_565 ?
C3 C4 1.309(7) . ?
C3 C8 1.532(13) . ?
C3 C8A 1.391(15) . ?
C4 H4 0.9500 . ?
C4 C5 1.496(6) . ?
C5 C7 1.528(4) . ?
C5 C7 1.528(4) 2_565 ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C10 C11 1.410(7) . ?
C10 C11 1.410(7) 2_565 ?
C11 H11 0.9500 . ?
C11 C12 1.386(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.362(8) . ?
C8A C9 1.218(19) . ?
C9 C10A 1.423(17) . ?
C10A C11A 1.382(10) . ?
C10A C15 1.379(10) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.382(10) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.394(10) . ?
C13A C14 1.77(3) 5_466 ?
C13A C14 1.383(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(10) . ?
C15 H15 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O9 C10 117.3(10) . . ?
O1 N1 C2 121.1(3) . . ?
O1 N1 C5 124.1(4) . . ?
C2 N1 C5 114.8(3) . . ?
N1 C2 C3 99.8(3) . . ?
N1 C2 C6 109.7(2) . . ?
N1 C2 C6 109.7(2) . 2_565 ?
C3 C2 C6 112.8(2) . 2_565 ?
C3 C2 C6 112.8(2) . . ?
C6 C2 C6 111.3(4) . 2_565 ?
C2 C3 C8 112.0(6) . . ?
C4 C3 C2 112.7(4) . . ?
C4 C3 C8 135.3(7) . . ?
C4 C3 C8A 115.5(7) . . ?
C8A C3 C2 131.8(7) . . ?
C3 C4 H4 123.4 . . ?
C3 C4 C5 113.2(4) . . ?
C5 C4 H4 123.4 . . ?
N1 C5 C4 99.5(4) . . ?
N1 C5 C7 109.6(3) . . ?
N1 C5 C7 109.6(3) . 2_565 ?
C4 C5 C7 113.2(3) . . ?
C4 C5 C7 113.2(3) . 2_565 ?
C7 C5 C7 111.1(4) 2_565 . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O8 C8 O9 121.3(11) . . ?
O8 C8 C3 131.9(11) . . ?
O9 C8 C3 106.8(10) . . ?
O9 C10 C11 123.4(5) . . ?
O9 C10 C11 123.4(5) . 2_565 ?
C11 C10 C11 112.6(10) 2_565 . ?
C10 C11 H11 118.2 . . ?
C12 C11 C10 123.6(7) . . ?
C12 C11 H11 118.2 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(8) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C12 118.4(12) . 2_565 ?
C9 C8A C3 172.6(16) . . ?
C8A C9 C10A 176.8(16) . . ?
C11A C10A C9 122.3(14) . . ?
C15 C10A C9 119.8(16) . . ?
C15 C10A C11A 117.9(18) . . ?
C10A C11A H11A 118.9 . . ?
C10A C11A C12A 122(2) . . ?
C12A C11A H11A 118.9 . . ?
C11A C12A H12A 119.4 . . ?
C11A C12A C13A 121(2) . . ?
C13A C12A H12A 119.4 . . ?
C12A C13A C14 109.7(17) . 5_466 ?
C14 C13A C12A 114.6(18) . . ?
C14 C13A C14 135.8(12) . 5_466 ?
C13A C14 H14 117.3 . . ?
C15 C14 C13A 125(2) . . ?
C15 C14 H14 117.3 . . ?
C10A C15 C14 119(2) . . ?
C10A C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C2 C3 180.000(3) . . . . ?
O1 N1 C2 C6 -61.3(3) . . . 2_565 ?
O1 N1 C2 C6 61.3(3) . . . . ?
O1 N1 C5 C4 180.000(3) . . . . ?
O1 N1 C5 C7 -61.1(3) . . . . ?
O1 N1 C5 C7 61.1(3) . . . 2_565 ?
O9 C10 C11 C12 171.7(10) . . . . ?
N1 C2 C3 C4 0.000(3) . . . . ?
N1 C2 C3 C8 180.000(5) . . . . ?
N1 C2 C3 C8A 180.000(8) . . . . ?
C2 N1 C5 C4 0.000(3) . . . . ?
C2 N1 C5 C7 118.9(3) . . . . ?
C2 N1 C5 C7 -118.9(3) . . . 2_565 ?
C2 C3 C4 C5 0.000(3) . . . . ?
C2 C3 C8 O8 0.000(8) . . . . ?
C2 C3 C8 O9 180.000(4) . . . . ?
C3 C4 C5 N1 0.000(3) . . . . ?
C3 C4 C5 C7 -116.2(3) . . . . ?
C3 C4 C5 C7 116.2(3) . . . 2_565 ?
C4 C3 C8 O8 180.000(5) . . . . ?
C4 C3 C8 O9 0.000(7) . . . . ?
C5 N1 C2 C3 0.000(2) . . . . ?
C5 N1 C2 C6 118.7(3) . . . 2_565 ?
C5 N1 C2 C6 -118.7(3) . . . . ?
C6 C2 C3 C4 -116.4(3) 2_565 . . . ?
C6 C2 C3 C4 116.4(3) . . . . ?
C6 C2 C3 C8 -63.6(3) . . . . ?
C6 C2 C3 C8 63.6(3) 2_565 . . . ?
C6 C2 C3 C8A -63.6(3) . . . . ?
C6 C2 C3 C8A 63.6(3) 2_565 . . . ?
C8 O9 C10 C11 94.5(11) . . . . ?
C8 O9 C10 C11 -94.5(11) . . . 2_565 ?
C8 C3 C4 C5 180.000(3) . . . . ?
C10 O9 C8 O8 0.000(8) . . . . ?
C10 O9 C8 C3 180.000(4) . . . . ?
C10 C11 C12 C13 2.5(17) . . . . ?
C11 C10 C11 C12 -0.1(18) 2_565 . . . ?
C11 C12 C13 C12 -5(2) . . . 2_565 ?
C8A C3 C4 C5 180.000(3) . . . . ?
C9 C10A C11A C12A 180.000(7) . . . . ?
C9 C10A C15 C14 180.000(10) . . . . ?
C10A C11A C12A C13A 0.000(8) . . . . ?
C11A C10A C15 C14 0.000(7) . . . . ?
C11A C12A C13A C14 0.000(10) . . . . ?
C11A C12A C13A C14 180.000(7) . . . 5_466 ?
C12A C13A C14 C15 0.000(9) . . . . ?
C13A C14 C15 C10A 0.000(12) . . . . ?
C14 C13A C14 C15 180.000(10) 5_466 . . . ?
C15 C10A C11A C12A 0.000(9) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/hexane'
####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 2212066'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-10-10 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;
_audit_creation_date             2022-10-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H16 N O2'
_chemical_formula_sum            'C9 H16 N O2'
_chemical_formula_weight         170.23
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        P21
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.9143(13)
_cell_length_b                   10.376(2)
_cell_length_c                   7.9856(18)
_cell_angle_alpha                90
_cell_angle_beta                 105.790(6)
_cell_angle_gamma                90
_cell_volume                     471.56(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1522
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             186
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5723
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.303
_diffrn_reflns_theta_min         2.651
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'AFC10: Fixed χ 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       ω
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           66.0
_diffrn_source_power             2.97
_diffrn_source_type              'Rigaku FR-X'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.864
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                1517
_reflns_number_total             1700
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrystalClear-SM Expert 2.1 b32 (Rigaku OD, 2014)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x was found to be meaningless and was removed from the CIF.
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     117
_refine_ls_number_reflns         1700
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0300P)²+0.0210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0857
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H) groups
2. Restrained distances
 O10-H10
 0.98 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4)
3.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6698(3) 0.4203(2) 0.9374(2) 0.0429(5) Uani 1 1 d . . . . .
O10 O 0.8217(3) 0.4221(2) 0.2974(2) 0.0447(5) Uani 1 1 d D . . . .
H10 H 0.776(6) 0.428(4) 0.174(3) 0.091(13) Uiso 1 1 d D . . . .
N1 N 0.7267(3) 0.4796(2) 0.8147(3) 0.0302(5) Uani 1 1 d . . . . .
C2 C 0.6513(4) 0.4321(2) 0.6330(3) 0.0271(6) Uani 1 1 d . . . . .
C3 C 0.7628(4) 0.5334(2) 0.5458(3) 0.0284(6) Uani 1 1 d . . . . .
C4 C 0.8756(4) 0.6214(2) 0.6560(3) 0.0300(6) Uani 1 1 d . . . . .
H4 H 0.956211 0.691833 0.622437 0.036 Uiso 1 1 calc R U . . .
C5 C 0.8648(4) 0.6001(2) 0.8396(3) 0.0304(6) Uani 1 1 d . . . . .
C6 C 0.7481(5) 0.2970(2) 0.6274(4) 0.0367(7) Uani 1 1 d . . . . .
H6A H 0.920093 0.299415 0.666725 0.044 Uiso 1 1 calc R U . . .
H6B H 0.698019 0.264133 0.507903 0.044 Uiso 1 1 calc R U . . .
H6C H 0.688530 0.240287 0.703868 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3847(4) 0.4325(3) 0.5688(4) 0.0410(7) Uani 1 1 d . . . . .
H7A H 0.320358 0.374069 0.640654 0.049 Uiso 1 1 calc R U . . .
H7B H 0.335657 0.403784 0.447392 0.049 Uiso 1 1 calc R U . . .
H7C H 0.326133 0.519994 0.577060 0.049 Uiso 1 1 calc R U . . .
C8 C 0.7348(5) 0.7067(3) 0.9047(4) 0.0407(7) Uani 1 1 d . . . . .
H8A H 0.709496 0.681316 1.016427 0.049 Uiso 1 1 calc R U . . .
H8B H 0.582803 0.721679 0.819845 0.049 Uiso 1 1 calc R U . . .
H8C H 0.828278 0.786012 0.919995 0.049 Uiso 1 1 calc R U . . .
C9 C 1.1067(4) 0.5765(3) 0.9656(3) 0.0382(7) Uani 1 1 d . . . . .
H9A H 1.187800 0.508603 0.919139 0.046 Uiso 1 1 calc R U . . .
H9B H 1.088135 0.549584 1.078722 0.046 Uiso 1 1 calc R U . . .
H9C H 1.199178 0.656061 0.979619 0.046 Uiso 1 1 calc R U . . .
C10 C 0.7296(5) 0.5352(3) 0.3533(3) 0.0347(6) Uani 1 1 d . . . . .
H10A H 0.559987 0.542020 0.293100 0.042 Uiso 1 1 calc R U . . .
H10B H 0.809466 0.611607 0.321861 0.042 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.277(3) . ?
O10 H10 0.95(2) . ?
O10 C10 1.415(3) . ?
N1 C2 1.481(3) . ?
N1 C5 1.477(3) . ?
C2 C3 1.508(3) . ?
C2 C6 1.519(4) . ?
C2 C7 1.520(3) . ?
C3 C4 1.317(3) . ?
C3 C10 1.496(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.501(3) . ?
C5 C8 1.517(3) . ?
C5 C9 1.528(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O10 H10 104(3) . . ?
O1 N1 C2 121.25(19) . . ?
O1 N1 C5 123.8(2) . . ?
C5 N1 C2 114.93(19) . . ?
N1 C2 C3 99.63(18) . . ?
N1 C2 C6 108.7(2) . . ?
N1 C2 C7 109.73(19) . . ?
C3 C2 C6 114.4(2) . . ?
C3 C2 C7 112.7(2) . . ?
C6 C2 C7 110.9(2) . . ?
C4 C3 C2 112.4(2) . . ?
C4 C3 C10 125.4(2) . . ?
C10 C3 C2 122.1(2) . . ?
C3 C4 H4 123.1 . . ?
C3 C4 C5 113.7(2) . . ?
C5 C4 H4 123.1 . . ?
N1 C5 C4 99.33(19) . . ?
N1 C5 C8 110.49(19) . . ?
N1 C5 C9 109.7(2) . . ?
C4 C5 C8 112.8(2) . . ?
C4 C5 C9 112.7(2) . . ?
C8 C5 C9 111.2(2) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O10 C10 C3 111.1(2) . . ?
O10 C10 H10A 109.4 . . ?
O10 C10 H10B 109.4 . . ?
C3 C10 H10A 109.4 . . ?
C3 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O10 H10 O1 0.95(2) 1.83(3) 2.769(3) 173(4) 1_554 yes

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 N1 C2 C3 -179.7(2) . . . . ?
O1 N1 C2 C6 -59.7(3) . . . . ?
O1 N1 C2 C7 61.8(3) . . . . ?
O1 N1 C5 C4 179.7(2) . . . . ?
O1 N1 C5 C8 -61.6(3) . . . . ?
O1 N1 C5 C9 61.4(3) . . . . ?
N1 C2 C3 C4 -0.8(2) . . . . ?
N1 C2 C3 C10 -176.6(2) . . . . ?
C2 N1 C5 C4 -1.8(2) . . . . ?
C2 N1 C5 C8 117.0(2) . . . . ?
C2 N1 C5 C9 -120.1(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C10 O10 -62.2(3) . . . . ?
C3 C4 C5 N1 1.2(3) . . . . ?
C3 C4 C5 C8 -115.8(2) . . . . ?
C3 C4 C5 C9 117.2(2) . . . . ?
C4 C3 C10 O10 122.5(3) . . . . ?
C5 N1 C2 C3 1.6(2) . . . . ?
C5 N1 C2 C6 121.7(2) . . . . ?
C5 N1 C2 C7 -116.8(2) . . . . ?
C6 C2 C3 C4 -116.5(2) . . . . ?
C6 C2 C3 C10 67.6(3) . . . . ?
C7 C2 C3 C4 115.5(2) . . . . ?
C7 C2 C3 C10 -60.4(3) . . . . ?
C10 C3 C4 C5 175.4(2) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/hexane'
####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 2212062'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-10-10 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;
_audit_creation_date             2022-10-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H34 N2 O2'
_chemical_formula_sum            'C32 H34 N2 O2'
_chemical_formula_weight         478.61
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        P21/c
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.510(9)
_cell_length_b                   9.475(3)
_cell_length_c                   6.564(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.085(6)
_cell_angle_gamma                90
_cell_volume                     1396.4(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    927
_cell_measurement_temperature    173
_cell_measurement_theta_max      47.00
_cell_measurement_theta_min      18.90
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.852
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1191
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            14088
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.170
_diffrn_reflns_theta_min         1.968
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       'AFC12: Kappa 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P100K'
_diffrn_measurement_method       ω
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_type              'Rigaku MM-007HF'
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1409
_reflns_number_total             2490
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2490
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0967
_refine_ls_restrained_S_all      0.948
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2473
_refine_ls_wR_factor_ref         0.2806
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C13(H13), C14(H14), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.89028(11) 0.5046(2) 1.5994(3) 0.0600(7) Uani 1 1 d . . . . .
N1 N 0.86386(12) 0.5068(2) 1.4198(3) 0.0464(7) Uani 1 1 d . . . . .
C2 C 0.79896(13) 0.5002(3) 1.3841(4) 0.0425(7) Uani 1 1 d . . . . .
C3 C 0.79334(13) 0.4989(2) 1.1520(4) 0.0410(7) Uani 1 1 d . . . . .
C4 C 0.84660(13) 0.5015(2) 1.0734(4) 0.0433(7) Uani 1 1 d . . . . .
H4 H 0.851632 0.502142 0.930925 0.052 Uiso 1 1 calc R U . . .
C5 C 0.89723(13) 0.5032(3) 1.2330(4) 0.0438(7) Uani 1 1 d . . . . .
C6 C 0.77562(15) 0.3645(3) 1.4733(5) 0.0562(8) Uani 1 1 d . . . . .
H6A H 0.733680 0.351787 1.425949 0.067 Uiso 1 1 calc R U . . .
H6B H 0.779235 0.370058 1.622721 0.067 Uiso 1 1 calc R U . . .
H6C H 0.798905 0.284318 1.428539 0.067 Uiso 1 1 calc R U . . .
C7 C 0.76999(15) 0.6284(3) 1.4743(5) 0.0587(9) Uani 1 1 d . . . . .
H7A H 0.727114 0.627230 1.435952 0.070 Uiso 1 1 calc R U . . .
H7B H 0.787551 0.714493 1.421793 0.070 Uiso 1 1 calc R U . . .
H7C H 0.776603 0.626125 1.623489 0.070 Uiso 1 1 calc R U . . .
C8 C 0.93549(14) 0.3699(3) 1.2306(5) 0.0574(8) Uani 1 1 d . . . . .
H8A H 0.910214 0.286602 1.243470 0.069 Uiso 1 1 calc R U . . .
H8B H 0.965898 0.372616 1.345088 0.069 Uiso 1 1 calc R U . . .
H8C H 0.954875 0.365025 1.101773 0.069 Uiso 1 1 calc R U . . .
C9 C 0.93588(14) 0.6356(3) 1.2208(5) 0.0581(9) Uani 1 1 d . . . . .
H9A H 0.965200 0.638266 1.338506 0.070 Uiso 1 1 calc R U . . .
H9B H 0.910590 0.719710 1.221600 0.070 Uiso 1 1 calc R U . . .
H9C H 0.956598 0.633372 1.094485 0.070 Uiso 1 1 calc R U . . .
C10 C 0.73677(14) 0.4950(3) 1.0414(5) 0.0473(7) Uani 1 1 d . . . . .
C11 C 0.68925(16) 0.4914(3) 0.9491(5) 0.0563(8) Uani 1 1 d . . . . .
C12 C 0.63378(16) 0.4910(4) 0.8242(6) 0.0639(9) Uani 1 1 d . . . . .
C13 C 0.5922(2) 0.5942(7) 0.8428(11) 0.161(4) Uani 1 1 d . . . . .
H13 H 0.599210 0.665537 0.943331 0.193 Uiso 1 1 calc R U . . .
C14 C 0.5405(3) 0.5965(7) 0.7185(12) 0.169(4) Uani 1 1 d . . . . .
H14 H 0.512529 0.669667 0.736598 0.203 Uiso 1 1 calc R U . . .
C15 C 0.52766(17) 0.4972(4) 0.5687(6) 0.0707(11) Uani 1 1 d . . . . .
C16 C 0.57026(15) 0.3958(4) 0.5497(6) 0.0702(10) Uani 1 1 d . . . . .
H16 H 0.563824 0.326205 0.446367 0.084 Uiso 1 1 calc R U . . .
C17 C 0.62189(15) 0.3907(4) 0.6740(5) 0.0683(10) Uani 1 1 d . . . . .
H17 H 0.649817 0.317288 0.656519 0.082 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.282(3) . ?
N1 C2 1.464(4) . ?
N1 C5 1.483(4) . ?
C2 C3 1.520(4) . ?
C2 C6 1.522(4) . ?
C2 C7 1.518(4) . ?
C3 C4 1.339(4) . ?
C3 C10 1.421(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.492(4) . ?
C5 C8 1.530(4) . ?
C5 C9 1.532(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.192(4) . ?
C11 C12 1.444(5) . ?
C12 C13 1.364(6) . ?
C12 C17 1.382(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.373(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.377(6) . ?
C15 C15 1.485(7) 3_666 ?
C15 C16 1.369(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.372(4) . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C2 122.6(2) . . ?
O1 N1 C5 122.0(3) . . ?
C2 N1 C5 115.2(2) . . ?
N1 C2 C3 99.9(2) . . ?
N1 C2 C6 110.0(2) . . ?
N1 C2 C7 110.8(2) . . ?
C3 C2 C6 111.8(2) . . ?
C7 C2 C3 113.0(2) . . ?
C7 C2 C6 110.9(3) . . ?
C4 C3 C2 111.9(3) . . ?
C4 C3 C10 126.8(3) . . ?
C10 C3 C2 121.3(3) . . ?
C3 C4 H4 123.5 . . ?
C3 C4 C5 112.9(3) . . ?
C5 C4 H4 123.5 . . ?
N1 C5 C4 100.0(2) . . ?
N1 C5 C8 110.3(2) . . ?
N1 C5 C9 110.3(2) . . ?
C4 C5 C8 112.7(2) . . ?
C4 C5 C9 112.4(2) . . ?
C8 C5 C9 110.7(3) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C3 179.8(4) . . ?
C10 C11 C12 175.7(4) . . ?
C13 C12 C11 121.2(3) . . ?
C13 C12 C17 117.2(3) . . ?
C17 C12 C11 121.5(3) . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 121.1(4) . . ?
C14 C13 H13 119.5 . . ?
C13 C14 H14 118.7 . . ?
C13 C14 C15 122.7(4) . . ?
C15 C14 H14 118.7 . . ?
C14 C15 C15 122.2(4) . 3_666 ?
C16 C15 C14 115.5(4) . . ?
C16 C15 C15 122.2(4) . 3_666 ?
C15 C16 H16 118.7 . . ?
C15 C16 C17 122.7(3) . . ?
C17 C16 H16 118.7 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 C12 120.8(3) . . ?
C16 C17 H17 119.6 . . ?

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 N1 C2 C3 -177.3(2) . . . . ?
O1 N1 C2 C6 -59.6(3) . . . . ?
O1 N1 C2 C7 63.4(3) . . . . ?
O1 N1 C5 C4 177.7(2) . . . . ?
O1 N1 C5 C8 58.8(3) . . . . ?
O1 N1 C5 C9 -63.8(3) . . . . ?
N1 C2 C3 C4 1.1(3) . . . . ?
N1 C2 C3 C10 -179.1(2) . . . . ?
C2 N1 C5 C4 2.9(2) . . . . ?
C2 N1 C5 C8 -116.0(2) . . . . ?
C2 N1 C5 C9 121.4(2) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 N1 -2.1(3) . . . . ?
C3 C4 C5 C8 115.0(3) . . . . ?
C3 C4 C5 C9 -119.1(3) . . . . ?
C5 N1 C2 C3 -2.5(2) . . . . ?
C5 N1 C2 C6 115.2(2) . . . . ?
C5 N1 C2 C7 -121.9(2) . . . . ?
C6 C2 C3 C4 -115.3(3) . . . . ?
C6 C2 C3 C10 64.6(3) . . . . ?
C7 C2 C3 C4 118.8(3) . . . . ?
C7 C2 C3 C10 -61.3(3) . . . . ?
C10 C3 C4 C5 -179.2(2) . . . . ?
C11 C12 C13 C14 177.5(7) . . . . ?
C11 C12 C17 C16 -176.7(4) . . . . ?
C12 C13 C14 C15 -0.5(14) . . . . ?
C13 C12 C17 C16 0.0(7) . . . . ?
C13 C14 C15 C15 -178.3(8) . . . 3_666 ?
C13 C14 C15 C16 -0.7(11) . . . . ?
C14 C15 C16 C17 1.4(7) . . . . ?
C15 C15 C16 C17 179.1(5) 3_666 . . . ?
C15 C16 C17 C12 -1.1(6) . . . . ?
C17 C12 C13 C14 0.8(11) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane/ethyl acetate/hexane'
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2212063'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-10-10 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;
_audit_creation_date             2022-10-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H14 N O2'
_chemical_formula_sum            'C9 H14 N O2'
_chemical_formula_weight         168.21
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        P43
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x, z+3/4'
'-x, -y, z+1/2'
'y, -x, z+1/4'

_cell_length_a                   7.9818(9)
_cell_length_b                   7.9818(9)
_cell_length_c                   15.057(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     959.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1116
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      40.40
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.936
_exptl_absorpt_coefficient_mu    0.667
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            10251
_diffrn_reflns_point_group_measured_fraction_full 0.847
_diffrn_reflns_point_group_measured_fraction_max 0.842
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.290
_diffrn_reflns_theta_min         5.543
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'AFC12: Kappa 4 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P100K'
_diffrn_measurement_method       ω
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku MM-007HF'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.624
_reflns_Friedel_fraction_full    0.685
_reflns_Friedel_fraction_max     0.675
_reflns_number_gt                1477
_reflns_number_total             1501
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
'CrystalClear-SM Expert 2.1 b32 (Rigaku OD, 2014)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details 
;
 Flack x was found to be meaningless and was removed from the CIF.
;
_refine_ls_extinction_coef       0.138(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         1501
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0491
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0871P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1078
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3765(2) 0.8997(2) 0.61691(12) 0.0451(5) Uani 1 1 d . . . . .
O8 O 0.2997(3) 1.1776(3) 0.94278(16) 0.0550(6) Uani 1 1 d . . . . .
N1 N 0.4238(2) 0.9170(2) 0.69685(14) 0.0343(5) Uani 1 1 d . . . . .
C2 C 0.3407(3) 1.0340(3) 0.75932(16) 0.0328(5) Uani 1 1 d . . . . .
C3 C 0.4386(3) 0.9951(2) 0.84286(16) 0.0334(5) Uani 1 1 d . . . . .
C4 C 0.5585(3) 0.8821(3) 0.82912(16) 0.0348(5) Uani 1 1 d . . . . .
H4 H 0.633338 0.845456 0.874192 0.042 Uiso 1 1 calc R U . . .
C5 C 0.5638(3) 0.8184(3) 0.73569(15) 0.0334(5) Uani 1 1 d . . . . .
C6 C 0.3670(4) 1.2146(3) 0.7278(2) 0.0466(6) Uani 1 1 d . . . . .
H6A H 0.487195 1.239377 0.725795 0.056 Uiso 1 1 calc R U . . .
H6B H 0.311674 1.291777 0.769011 0.056 Uiso 1 1 calc R U . . .
H6C H 0.318941 1.228106 0.668301 0.056 Uiso 1 1 calc R U . . .
C7 C 0.1541(3) 0.9917(3) 0.76508(17) 0.0407(6) Uani 1 1 d . . . . .
H7A H 0.102644 1.004782 0.706396 0.049 Uiso 1 1 calc R U . . .
H7B H 0.099534 1.067444 0.807343 0.049 Uiso 1 1 calc R U . . .
H7C H 0.140561 0.875688 0.785195 0.049 Uiso 1 1 calc R U . . .
C8 C 0.4066(3) 1.0734(3) 0.92942(17) 0.0422(6) Uani 1 1 d . . . . .
H8 H 0.474377 1.039940 0.978149 0.051 Uiso 1 1 calc R U . . .
C9 C 0.5249(3) 0.6315(3) 0.72997(19) 0.0427(6) Uani 1 1 d . . . . .
H9A H 0.615916 0.567660 0.757576 0.051 Uiso 1 1 calc R U . . .
H9B H 0.514064 0.598685 0.667515 0.051 Uiso 1 1 calc R U . . .
H9C H 0.419668 0.608162 0.761149 0.051 Uiso 1 1 calc R U . . .
C10 C 0.7285(3) 0.8600(3) 0.68789(19) 0.0453(6) Uani 1 1 d . . . . .
H10A H 0.721570 0.823002 0.625933 0.054 Uiso 1 1 calc R U . . .
H10B H 0.821366 0.802255 0.717459 0.054 Uiso 1 1 calc R U . . .
H10C H 0.747556 0.981200 0.689761 0.054 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.269(3) . ?
O8 C8 1.208(3) . ?
N1 C2 1.482(3) . ?
N1 C5 1.487(3) . ?
C2 C3 1.513(3) . ?
C2 C6 1.532(3) . ?
C2 C7 1.530(3) . ?
C3 C4 1.332(3) . ?
C3 C8 1.468(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.496(3) . ?
C5 C9 1.526(3) . ?
C5 C10 1.534(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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 N1 C2 122.52(17) . . ?
O1 N1 C5 122.62(19) . . ?
C2 N1 C5 114.84(18) . . ?
N1 C2 C3 99.66(16) . . ?
N1 C2 C6 109.6(2) . . ?
N1 C2 C7 109.43(19) . . ?
C3 C2 C6 112.34(19) . . ?
C3 C2 C7 114.22(19) . . ?
C7 C2 C6 111.01(19) . . ?
C4 C3 C2 112.4(2) . . ?
C4 C3 C8 123.5(2) . . ?
C8 C3 C2 124.1(2) . . ?
C3 C4 H4 123.3 . . ?
C3 C4 C5 113.4(2) . . ?
C5 C4 H4 123.3 . . ?
N1 C5 C4 99.71(18) . . ?
N1 C5 C9 110.01(17) . . ?
N1 C5 C10 110.17(19) . . ?
C4 C5 C9 112.3(2) . . ?
C4 C5 C10 113.1(2) . . ?
C9 C5 C10 111.1(2) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O8 C8 C3 124.3(2) . . ?
O8 C8 H8 117.8 . . ?
C3 C8 H8 117.8 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C2 C3 176.60(19) . . . . ?
O1 N1 C2 C6 -65.4(3) . . . . ?
O1 N1 C2 C7 56.5(3) . . . . ?
O1 N1 C5 C4 -177.4(2) . . . . ?
O1 N1 C5 C9 -59.2(3) . . . . ?
O1 N1 C5 C10 63.5(3) . . . . ?
N1 C2 C3 C4 2.0(2) . . . . ?
N1 C2 C3 C8 -178.37(19) . . . . ?
C2 N1 C5 C4 1.1(2) . . . . ?
C2 N1 C5 C9 119.3(2) . . . . ?
C2 N1 C5 C10 -118.0(2) . . . . ?
C2 C3 C4 C5 -1.6(2) . . . . ?
C2 C3 C8 O8 -0.5(4) . . . . ?
C3 C4 C5 N1 0.3(2) . . . . ?
C3 C4 C5 C9 -116.1(2) . . . . ?
C3 C4 C5 C10 117.2(2) . . . . ?
C4 C3 C8 O8 179.0(2) . . . . ?
C5 N1 C2 C3 -1.9(2) . . . . ?
C5 N1 C2 C6 116.1(2) . . . . ?
C5 N1 C2 C7 -121.97(19) . . . . ?
C6 C2 C3 C4 -113.9(2) . . . . ?
C6 C2 C3 C8 65.7(3) . . . . ?
C7 C2 C3 C4 118.6(2) . . . . ?
C7 C2 C3 C8 -61.9(3) . . . . ?
C8 C3 C4 C5 178.84(19) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate'
####################################################################### 
# 
# 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_20
_database_code_depnum_ccdc_archive 'CCDC 2212068'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-10-10 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;
_audit_creation_date             2022-10-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H26 N2 O2'
_chemical_formula_sum            'C20 H26 N2 O2'
_chemical_formula_weight         326.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.8003(11)
_cell_length_b                   5.8739(12)
_cell_length_c                   14.924(4)
_cell_angle_alpha                89.862(19)
_cell_angle_beta                 86.020(19)
_cell_angle_gamma                69.143(14)
_cell_volume                     473.87(19)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1186
_cell_measurement_temperature    173
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.70
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.991
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.144
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             176
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10291
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.327
_diffrn_reflns_theta_min         1.368
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 11.628
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'AFC10: Fixed χ 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       ω
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku FR-X'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1103
_reflns_number_total             1707
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b32 (Rigaku, 2014)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b32'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b32'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL Version 2014/1 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.958
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1707
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0760
_refine_ls_restrained_S_all      0.958
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2021
_refine_ls_wR_factor_ref         0.2187
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3414(4) 0.6231(4) 0.17138(15) 0.0625(7) Uani 1 1 d . . . . .
N1 N 0.5171(4) 0.4568(4) 0.20713(16) 0.0466(7) Uani 1 1 d . . . . .
C2 C 0.5383(5) 0.4470(4) 0.30515(18) 0.0407(7) Uani 1 1 d . . . . .
C3 C 0.7676(5) 0.2190(5) 0.30823(18) 0.0393(7) Uani 1 1 d . . . . .
C4 C 0.8567(5) 0.1232(5) 0.22717(19) 0.0427(7) Uani 1 1 d . . . . .
H4 H 0.999887 -0.019462 0.217083 0.051 Uiso 1 1 calc R U . . .
C5 C 0.7104(5) 0.2613(5) 0.15319(19) 0.0460(8) Uani 1 1 d . . . . .
C6 C 0.5770(6) 0.6726(5) 0.3393(2) 0.0536(8) Uani 1 1 d . . . . .
H6A H 0.722142 0.689382 0.306430 0.064 Uiso 1 1 calc R U . . .
H6B H 0.603422 0.657653 0.403545 0.064 Uiso 1 1 calc R U . . .
H6C H 0.430602 0.816659 0.330055 0.064 Uiso 1 1 calc R U . . .
C7 C 0.3108(5) 0.4172(6) 0.3521(2) 0.0548(9) Uani 1 1 d . . . . .
H7A H 0.287558 0.273477 0.327072 0.066 Uiso 1 1 calc R U . . .
H7B H 0.165270 0.562372 0.343069 0.066 Uiso 1 1 calc R U . . .
H7C H 0.332546 0.396621 0.416529 0.066 Uiso 1 1 calc R U . . .
C8 C 0.5930(6) 0.1131(6) 0.1018(2) 0.0617(9) Uani 1 1 d . . . . .
H8A H 0.499674 0.044782 0.144264 0.074 Uiso 1 1 calc R U . . .
H8B H 0.722600 -0.019591 0.067965 0.074 Uiso 1 1 calc R U . . .
H8C H 0.480840 0.218499 0.060187 0.074 Uiso 1 1 calc R U . . .
C9 C 0.8570(6) 0.3719(6) 0.0909(2) 0.0628(10) Uani 1 1 d . . . . .
H9A H 0.928304 0.467261 0.126327 0.075 Uiso 1 1 calc R U . . .
H9B H 0.747517 0.478405 0.048819 0.075 Uiso 1 1 calc R U . . .
H9C H 0.990182 0.241688 0.057340 0.075 Uiso 1 1 calc R U . . .
C10 C 0.8647(5) 0.1260(5) 0.39117(19) 0.0424(7) Uani 1 1 d . . . . .
C11 C 0.9490(5) 0.0469(5) 0.46076(19) 0.0425(7) Uani 1 1 d . . . . .


_geom_special_details            
;
    ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.281(3) . ?
N1 C2 1.476(4) . ?
N1 C5 1.479(4) . ?
C2 C3 1.518(3) . ?
C2 C6 1.516(4) . ?
C2 C7 1.516(4) . ?
C3 C4 1.325(4) . ?
C3 C10 1.422(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.494(4) . ?
C5 C8 1.519(4) . ?
C5 C9 1.513(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.200(4) . ?
C11 C11 1.373(6) 2_756 ?

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 N1 C2 122.0(2) . . ?
O1 N1 C5 122.3(2) . . ?
C2 N1 C5 115.6(2) . . ?
N1 C2 C3 99.1(2) . . ?
N1 C2 C6 110.5(2) . . ?
N1 C2 C7 110.0(2) . . ?
C6 C2 C3 112.6(2) . . ?
C7 C2 C3 112.6(2) . . ?
C7 C2 C6 111.5(2) . . ?
C4 C3 C2 112.4(2) . . ?
C4 C3 C10 126.3(2) . . ?
C10 C3 C2 121.3(2) . . ?
C3 C4 H4 123.2 . . ?
C3 C4 C5 113.5(2) . . ?
C5 C4 H4 123.2 . . ?
N1 C5 C4 99.4(2) . . ?
N1 C5 C8 109.9(2) . . ?
N1 C5 C9 109.5(2) . . ?
C4 C5 C8 112.9(2) . . ?
C4 C5 C9 112.5(2) . . ?
C9 C5 C8 111.8(3) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C3 179.3(3) . . ?
C10 C11 C11 178.6(4) . 2_756 ?

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 N1 C2 C3 178.9(2) . . . . ?
O1 N1 C2 C6 -62.7(3) . . . . ?
O1 N1 C2 C7 60.7(3) . . . . ?
O1 N1 C5 C4 -179.0(2) . . . . ?
O1 N1 C5 C8 -60.3(3) . . . . ?
O1 N1 C5 C9 62.9(4) . . . . ?
N1 C2 C3 C4 0.5(3) . . . . ?
N1 C2 C3 C10 -178.6(2) . . . . ?
C2 N1 C5 C4 0.5(3) . . . . ?
C2 N1 C5 C8 119.2(3) . . . . ?
C2 N1 C5 C9 -117.5(3) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 N1 -0.2(3) . . . . ?
C3 C4 C5 C8 -116.6(3) . . . . ?
C3 C4 C5 C9 115.6(3) . . . . ?
C5 N1 C2 C3 -0.7(3) . . . . ?
C5 N1 C2 C6 117.7(3) . . . . ?
C5 N1 C2 C7 -118.8(3) . . . . ?
C6 C2 C3 C4 -116.2(3) . . . . ?
C6 C2 C3 C10 64.6(3) . . . . ?
C7 C2 C3 C4 116.7(3) . . . . ?
C7 C2 C3 C10 -62.5(3) . . . . ?
C10 C3 C4 C5 178.9(2) . . . . ?


#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2212064'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-10-10 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;
_audit_creation_date             2022-10-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H14 N O3'
_chemical_formula_sum            'C9 H14 N O3'
_chemical_formula_weight         184.21
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        P43
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   7.8822(19)
_cell_length_b                   7.8822(19)
_cell_length_c                   16.118(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1001.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1428
_cell_measurement_temperature    173
_cell_measurement_theta_max      21.90
_cell_measurement_theta_min      2.90
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.989
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0892
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12427
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.358
_diffrn_reflns_theta_min         2.527
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'AFC10: Fixed χ 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       ω
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           66.0
_diffrn_source_power             2.97
_diffrn_source_type              'Rigaku FR-X'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.915
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                1323
_reflns_number_total             1835
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_refine_diff_density_max         0.113
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x found to be meaningless and removed from the CIF.
;
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1835
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      0.948
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0256P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0638
_refine_ls_wR_factor_ref         0.0705
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.764(3)
 0.236(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups
3. Restrained distances
 O9-H9
 0.98 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4)
4.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5518(4) 0.8689(4) 0.27249(14) 0.0405(7) Uani 1 1 d . . . . .
O8 O 0.3734(4) 0.8461(4) 0.59502(17) 0.0447(8) Uani 1 1 d . . . . .
O9 O 0.5531(4) 1.0590(4) 0.62235(16) 0.0427(8) Uani 1 1 d D . . . .
H9 H 0.501(5) 1.042(6) 0.6756(18) 0.057(14) Uiso 1 1 d D . . . .
N1 N 0.5594(4) 0.9331(4) 0.34541(17) 0.0312(8) Uani 1 1 d . . . . .
C2 C 0.4651(5) 0.8576(5) 0.4161(2) 0.0290(9) Uani 1 1 d . . . . .
C3 C 0.5312(5) 0.9705(5) 0.4844(2) 0.0279(9) Uani 1 1 d . . . . .
C4 C 0.6364(5) 1.0889(5) 0.4575(2) 0.0323(10) Uani 1 1 d . . . . .
H4 H 0.686847 1.171600 0.492634 0.039 Uiso 1 1 calc R U . . .
C5 C 0.6680(5) 1.0793(5) 0.3658(2) 0.0298(10) Uani 1 1 d . . . . .
C6 C 0.5119(6) 0.6727(5) 0.4249(3) 0.0425(11) Uani 1 1 d . . . . .
H6A H 0.449304 0.623197 0.471547 0.051 Uiso 1 1 calc R U . . .
H6B H 0.634036 0.662747 0.435175 0.051 Uiso 1 1 calc R U . . .
H6C H 0.482732 0.612166 0.373762 0.051 Uiso 1 1 calc R U . . .
C7 C 0.2747(5) 0.8809(6) 0.4004(3) 0.0474(13) Uani 1 1 d . . . . .
H7A H 0.243096 0.822950 0.348858 0.057 Uiso 1 1 calc R U . . .
H7B H 0.248911 1.002066 0.395522 0.057 Uiso 1 1 calc R U . . .
H7C H 0.210465 0.832443 0.446745 0.057 Uiso 1 1 calc R U . . .
C8 C 0.4764(6) 0.9488(6) 0.5720(2) 0.0354(11) Uani 1 1 d . . . . .
C9 C 0.6060(6) 1.2380(5) 0.3198(2) 0.0438(12) Uani 1 1 d . . . . .
H9A H 0.488487 1.262307 0.335742 0.053 Uiso 1 1 calc R U . . .
H9B H 0.611635 1.218329 0.259790 0.053 Uiso 1 1 calc R U . . .
H9C H 0.678136 1.334742 0.334352 0.053 Uiso 1 1 calc R U . . .
C10 C 0.8522(5) 1.0384(6) 0.3453(3) 0.0425(10) Uani 1 1 d . . . . .
H10A H 0.924981 1.131933 0.363618 0.051 Uiso 1 1 calc R U . . .
H10B H 0.864298 1.023117 0.285223 0.051 Uiso 1 1 calc R U . . .
H10C H 0.885719 0.933820 0.373775 0.051 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.281(4) . ?
O8 C8 1.205(5) . ?
O9 H9 0.96(3) . ?
O9 C8 1.333(5) . ?
N1 C2 1.485(5) . ?
N1 C5 1.473(5) . ?
C2 C3 1.509(5) . ?
C2 C6 1.510(5) . ?
C2 C7 1.532(6) . ?
C3 C4 1.322(6) . ?
C3 C8 1.487(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.501(5) . ?
C5 C9 1.534(5) . ?
C5 C10 1.523(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
C8 O9 H9 105(3) . . ?
O1 N1 C2 121.5(3) . . ?
O1 N1 C5 122.8(3) . . ?
C5 N1 C2 115.7(3) . . ?
N1 C2 C3 98.6(3) . . ?
N1 C2 C6 109.7(3) . . ?
N1 C2 C7 108.4(3) . . ?
C3 C2 C6 114.6(3) . . ?
C3 C2 C7 112.9(4) . . ?
C6 C2 C7 111.7(3) . . ?
C4 C3 C2 113.2(4) . . ?
C4 C3 C8 125.1(4) . . ?
C8 C3 C2 121.7(4) . . ?
C3 C4 H4 123.5 . . ?
C3 C4 C5 113.0(4) . . ?
C5 C4 H4 123.5 . . ?
N1 C5 C4 99.4(3) . . ?
N1 C5 C9 110.2(3) . . ?
N1 C5 C10 109.9(3) . . ?
C4 C5 C9 112.5(3) . . ?
C4 C5 C10 112.5(3) . . ?
C10 C5 C9 111.8(3) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O8 C8 O9 123.8(4) . . ?
O8 C8 C3 124.4(4) . . ?
O9 C8 C3 111.8(4) . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O9 H9 O1 0.96(3) 1.76(3) 2.620(4) 147(4) 2_675 yes

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 N1 C2 C3 175.2(3) . . . . ?
O1 N1 C2 C6 55.1(5) . . . . ?
O1 N1 C2 C7 -67.1(4) . . . . ?
O1 N1 C5 C4 -175.9(3) . . . . ?
O1 N1 C5 C9 65.9(4) . . . . ?
O1 N1 C5 C10 -57.7(4) . . . . ?
N1 C2 C3 C4 1.9(4) . . . . ?
N1 C2 C3 C8 -179.7(3) . . . . ?
C2 N1 C5 C4 0.9(4) . . . . ?
C2 N1 C5 C9 -117.4(3) . . . . ?
C2 N1 C5 C10 119.0(4) . . . . ?
C2 C3 C4 C5 -1.5(5) . . . . ?
C2 C3 C8 O8 -2.5(6) . . . . ?
C2 C3 C8 O9 178.6(3) . . . . ?
C3 C4 C5 N1 0.4(4) . . . . ?
C3 C4 C5 C9 116.9(4) . . . . ?
C3 C4 C5 C10 -115.8(4) . . . . ?
C4 C3 C8 O8 175.8(4) . . . . ?
C4 C3 C8 O9 -3.2(6) . . . . ?
C5 N1 C2 C3 -1.6(4) . . . . ?
C5 N1 C2 C6 -121.7(4) . . . . ?
C5 N1 C2 C7 116.1(4) . . . . ?
C6 C2 C3 C4 118.2(4) . . . . ?
C6 C2 C3 C8 -63.3(5) . . . . ?
C7 C2 C3 C4 -112.4(4) . . . . ?
C7 C2 C3 C8 66.1(5) . . . . ?
C8 C3 C4 C5 -179.9(3) . . . . ?

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.764(3)
2 0.236(3)
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Toluene'
####################################################################### 
# 
# 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_8-9
_database_code_depnum_ccdc_archive 'CCDC 2212065'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-10-10 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;
_audit_creation_date             2022-10-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H15.56 N2 O1.44, H2 O'
_chemical_formula_sum            'C9 H17.56 N2 O2.44'
_chemical_formula_weight         192.85
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.7049(9)
_cell_length_b                   8.1609(17)
_cell_length_c                   10.0105(16)
_cell_angle_alpha                102.84(3)
_cell_angle_beta                 94.37(2)
_cell_angle_gamma                117.329(10)
_cell_volume                     533.55(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1152
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.30
_cell_measurement_theta_min      2.10
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_correction_T_min  0.825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             210
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10852
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.383
_diffrn_reflns_theta_min         3.021
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'AFC10: Fixed χ 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       ω
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           66.0
_diffrn_source_power             2.97
_diffrn_source_type              'Rigaku FR-X'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1538
_reflns_number_total             1942
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.039(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1942
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.133
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0532P)²+0.3761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1494
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All N(H,H) groups, All O(H,H) groups
2. Restrained distances
 O11-H11A = O11-H11B = N8-H8A = N8-H8B
 0.98 with sigma of 0.02
 H11A-H11B
 1.6 with sigma of 0.04
 N1-O1
 1.27 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N1 \\sim O1: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
within 2A
4. Others
 Sof(H1)=1-FVAR(1)
 Sof(O1)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4)
5.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.4361(5) 0.9652(5) 0.3758(4) 0.0407(17) Uani 0.437(8) 1 d D U P A 1
O8 O 0.2046(2) 0.2363(2) 0.10092(19) 0.0416(5) Uani 1 1 d . . . . .
O11 O 0.5263(3) 0.1668(4) 0.1979(3) 0.0802(8) Uani 1 1 d D . . . .
H11A H 0.521(7) 0.161(7) 0.296(3) 0.120 Uiso 1 1 d D U . . .
H11B H 0.432(6) 0.209(6) 0.179(4) 0.120 Uiso 1 1 d D U . . .
N1 N 0.3044(3) 0.7992(3) 0.3271(2) 0.0382(5) Uani 1 1 d D U . . .
H1 H 0.412716 0.932818 0.364164 0.046 Uiso 0.563(8) 1 calc R U P A 2
N8 N -0.1200(3) 0.1355(3) 0.1034(2) 0.0411(6) Uani 1 1 d D . . . .
H8A H -0.154(4) 0.009(3) 0.046(3) 0.062 Uiso 1 1 d D U . . .
H8B H -0.221(4) 0.163(4) 0.133(3) 0.062 Uiso 1 1 d D U . . .
C2 C 0.3347(3) 0.6357(3) 0.2579(3) 0.0350(6) Uani 1 1 d . . . . .
C3 C 0.1209(3) 0.4709(3) 0.2154(2) 0.0325(5) Uani 1 1 d . . . . .
C4 C -0.0061(3) 0.5293(3) 0.2569(3) 0.0371(6) Uani 1 1 d . . . . .
H4 H -0.146248 0.446144 0.239258 0.045 Uiso 1 1 calc R U . . .
C5 C 0.0934(3) 0.7388(3) 0.3340(3) 0.0352(6) Uani 1 1 d . . . . .
C6 C 0.4307(4) 0.6777(4) 0.1339(3) 0.0533(8) Uani 1 1 d . . . . .
H6A H 0.559093 0.797279 0.166405 0.064 Uiso 1 1 calc R U . . .
H6B H 0.342721 0.691774 0.066867 0.064 Uiso 1 1 calc R U . . .
H6C H 0.452335 0.571071 0.088467 0.064 Uiso 1 1 calc R U . . .
C7 C 0.4648(4) 0.6083(4) 0.3643(3) 0.0502(7) Uani 1 1 d . . . . .
H7A H 0.395344 0.573732 0.440149 0.060 Uiso 1 1 calc R U . . .
H7B H 0.591647 0.728503 0.403037 0.060 Uiso 1 1 calc R U . . .
H7C H 0.490902 0.505084 0.318067 0.060 Uiso 1 1 calc R U . . .
C8 C 0.0716(3) 0.2712(3) 0.1362(2) 0.0352(6) Uani 1 1 d . . . . .
C9 C 0.0680(4) 0.7730(4) 0.4859(3) 0.0460(7) Uani 1 1 d . . . . .
H9A H 0.142830 0.911440 0.534542 0.055 Uiso 1 1 calc R U . . .
H9B H 0.118718 0.705369 0.532590 0.055 Uiso 1 1 calc R U . . .
H9C H -0.073782 0.724186 0.488043 0.055 Uiso 1 1 calc R U . . .
C10 C 0.0222(4) 0.8487(4) 0.2607(3) 0.0478(7) Uani 1 1 d . . . . .
H10A H 0.098689 0.986679 0.310705 0.057 Uiso 1 1 calc R U . . .
H10B H -0.119931 0.802383 0.260260 0.057 Uiso 1 1 calc R U . . .
H10C H 0.042128 0.827799 0.164181 0.057 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.213(4) . ?
O8 C8 1.239(3) . ?
O11 H11A 0.995(19) . ?
O11 H11B 0.956(19) . ?
N1 H1 0.9800 . ?
N1 C2 1.489(3) . ?
N1 C5 1.479(3) . ?
N8 H8A 0.963(18) . ?
N8 H8B 0.957(18) . ?
N8 C8 1.333(3) . ?
C2 C3 1.519(3) . ?
C2 C6 1.517(4) . ?
C2 C7 1.530(4) . ?
C3 C4 1.327(3) . ?
C3 C8 1.496(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.492(3) . ?
C5 C9 1.528(4) . ?
C5 C10 1.526(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
H11A O11 H11B 102(3) . . ?
O1 N1 C2 124.9(3) . . ?
O1 N1 C5 122.2(3) . . ?
C2 N1 H1 123.6 . . ?
C5 N1 H1 123.6 . . ?
C5 N1 C2 112.85(18) . . ?
H8A N8 H8B 121(3) . . ?
C8 N8 H8A 117.7(18) . . ?
C8 N8 H8B 121.3(19) . . ?
N1 C2 C3 100.88(17) . . ?
N1 C2 C6 109.1(2) . . ?
N1 C2 C7 109.2(2) . . ?
C3 C2 C7 112.6(2) . . ?
C6 C2 C3 113.1(2) . . ?
C6 C2 C7 111.4(2) . . ?
C4 C3 C2 111.6(2) . . ?
C4 C3 C8 127.0(2) . . ?
C8 C3 C2 121.43(19) . . ?
C3 C4 H4 123.4 . . ?
C3 C4 C5 113.2(2) . . ?
C5 C4 H4 123.4 . . ?
N1 C5 C4 101.42(18) . . ?
N1 C5 C9 110.8(2) . . ?
N1 C5 C10 109.7(2) . . ?
C4 C5 C9 112.0(2) . . ?
C4 C5 C10 112.2(2) . . ?
C10 C5 C9 110.4(2) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O8 C8 N8 122.0(2) . . ?
O8 C8 C3 120.7(2) . . ?
N8 C8 C3 117.4(2) . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O11 H11A O1 0.995(19) 1.82(4) 2.608(5) 134(4) 1_545 yes
O11 H11B O8 0.956(19) 1.99(2) 2.928(3) 166(4) . yes
N8 H8A O8 0.963(18) 2.053(19) 3.006(3) 170(3) 2 yes
N8 H8B O11 0.957(18) 2.107(19) 3.052(3) 169(3) 1_455 yes

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 N1 C2 C3 -178.0(3) . . . . ?
O1 N1 C2 C6 -58.7(4) . . . . ?
O1 N1 C2 C7 63.2(4) . . . . ?
O1 N1 C5 C4 177.9(3) . . . . ?
O1 N1 C5 C9 -63.1(4) . . . . ?
O1 N1 C5 C10 59.0(4) . . . . ?
N1 C2 C3 C4 -1.7(3) . . . . ?
N1 C2 C3 C8 178.2(2) . . . . ?
C2 N1 C5 C4 -3.3(3) . . . . ?
C2 N1 C5 C9 115.8(2) . . . . ?
C2 N1 C5 C10 -122.1(2) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C8 O8 -1.4(4) . . . . ?
C2 C3 C8 N8 179.9(2) . . . . ?
C3 C4 C5 N1 2.1(3) . . . . ?
C3 C4 C5 C9 -116.0(2) . . . . ?
C3 C4 C5 C10 119.1(2) . . . . ?
C4 C3 C8 O8 178.4(2) . . . . ?
C4 C3 C8 N8 -0.2(4) . . . . ?
C5 N1 C2 C3 3.1(2) . . . . ?
C5 N1 C2 C6 122.5(2) . . . . ?
C5 N1 C2 C7 -115.6(2) . . . . ?
C6 C2 C3 C4 -118.1(2) . . . . ?
C6 C2 C3 C8 61.8(3) . . . . ?
C7 C2 C3 C4 114.5(2) . . . . ?
C7 C2 C3 C8 -65.6(3) . . . . ?
C8 C3 C4 C5 179.9(2) . . . . ?

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
####################################################################### 
# 
# 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_15
_database_code_depnum_ccdc_archive 'CCDC 2212067'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-10-10 deposited with the CCDC.	2022-12-08 downloaded from the CCDC.
;
_audit_creation_date             2022-10-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H14 Br2 N O'
_chemical_formula_sum            'C10 H14 Br2 N O'
_chemical_formula_weight         324.04
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        P212121
_space_group_name_Hall           'P 2ac 2ab'
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'

_cell_length_a                   9.4876(9)
_cell_length_b                   10.2177(11)
_cell_length_c                   12.7098(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1232.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3959
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.40
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   0.560
_shelx_estimated_absorpt_T_min   0.420
_exptl_absorpt_coefficient_mu    6.550
_exptl_absorpt_correction_T_max  0.518
_exptl_absorpt_correction_T_min  0.391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15200
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.362
_diffrn_reflns_theta_min         2.558
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean 5.814
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'AFC10: Fixed χ 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       ω
_diffrn_measurement_specimen_support Loop
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           66.0
_diffrn_source_power             2.97
_diffrn_source_type              'Rigaku FR-X'
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2005
_reflns_number_total             2256
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b45'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b45'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'DIRDIF99-PATTY (Gould, et al., 1999)'
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 778 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     131
_refine_ls_number_reflns         2256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0188
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0238P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0421
_refine_ls_wR_factor_ref         0.0426
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.93366(5) 0.11988(3) 0.68928(3) 0.04772(12) Uani 1 1 d . . . . .
Br2 Br 1.05671(4) 0.36970(4) 0.57782(3) 0.04608(12) Uani 1 1 d . . . . .
O1 O 0.4630(2) 0.7268(2) 0.63970(18) 0.0320(5) Uani 1 1 d . . . . .
N1 N 0.5676(3) 0.6514(2) 0.62237(19) 0.0251(5) Uani 1 1 d . . . . .
C2 C 0.5827(3) 0.5229(3) 0.6742(2) 0.0246(7) Uani 1 1 d . . . . .
C3 C 0.7235(3) 0.4791(3) 0.6283(3) 0.0246(7) Uani 1 1 d . . . . .
C4 C 0.7788(3) 0.5703(3) 0.5657(2) 0.0243(7) Uani 1 1 d . . . . .
H4 H 0.867060 0.560629 0.531251 0.029 Uiso 1 1 calc R U . . .
C5 C 0.6876(3) 0.6903(3) 0.5548(3) 0.0237(7) Uani 1 1 d . . . . .
C6 C 0.5894(4) 0.5425(3) 0.7936(2) 0.0327(8) Uani 1 1 d . . . . .
H6A H 0.502404 0.584619 0.817756 0.039 Uiso 1 1 calc R U . . .
H6B H 0.670229 0.598017 0.811157 0.039 Uiso 1 1 calc R U . . .
H6C H 0.599694 0.457337 0.828220 0.039 Uiso 1 1 calc R U . . .
C7 C 0.4590(4) 0.4361(3) 0.6442(3) 0.0348(8) Uani 1 1 d . . . . .
H7A H 0.459609 0.421191 0.568055 0.042 Uiso 1 1 calc R U . . .
H7B H 0.370675 0.479063 0.664400 0.042 Uiso 1 1 calc R U . . .
H7C H 0.466867 0.352053 0.680907 0.042 Uiso 1 1 calc R U . . .
C8 C 0.7747(4) 0.3482(3) 0.6573(3) 0.0290(7) Uani 1 1 d . . . . .
H8 H 0.707737 0.294830 0.692643 0.035 Uiso 1 1 calc R U . . .
C9 C 0.8986(4) 0.2929(3) 0.6423(3) 0.0304(8) Uani 1 1 d . . . . .
C10 C 0.7549(3) 0.8156(3) 0.5993(3) 0.0346(9) Uani 1 1 d . . . . .
H10A H 0.791396 0.798161 0.670066 0.041 Uiso 1 1 calc R U . . .
H10B H 0.683722 0.884960 0.602802 0.041 Uiso 1 1 calc R U . . .
H10C H 0.832287 0.843359 0.553438 0.041 Uiso 1 1 calc R U . . .
C11 C 0.6383(3) 0.7125(3) 0.4418(3) 0.0300(8) Uani 1 1 d . . . . .
H11A H 0.568094 0.782795 0.440507 0.036 Uiso 1 1 calc R U . . .
H11B H 0.596193 0.631790 0.414486 0.036 Uiso 1 1 calc R U . . .
H11C H 0.719055 0.737124 0.397995 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C9 1.895(3) . ?
Br2 C9 1.881(3) . ?
O1 N1 1.275(3) . ?
N1 C2 1.475(4) . ?
N1 C5 1.481(4) . ?
C2 C3 1.524(4) . ?
C2 C6 1.532(4) . ?
C2 C7 1.520(4) . ?
C3 C4 1.333(5) . ?
C3 C8 1.471(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.506(4) . ?
C5 C10 1.538(5) . ?
C5 C11 1.527(5) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C9 1.318(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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 N1 C2 122.4(2) . . ?
O1 N1 C5 122.5(2) . . ?
C2 N1 C5 115.0(2) . . ?
N1 C2 C3 100.1(2) . . ?
N1 C2 C6 109.3(2) . . ?
N1 C2 C7 109.4(3) . . ?
C3 C2 C6 112.4(3) . . ?
C7 C2 C3 114.2(2) . . ?
C7 C2 C6 110.8(3) . . ?
C4 C3 C2 111.6(3) . . ?
C4 C3 C8 131.0(3) . . ?
C8 C3 C2 117.4(3) . . ?
C3 C4 H4 123.3 . . ?
C3 C4 C5 113.4(3) . . ?
C5 C4 H4 123.3 . . ?
N1 C5 C4 99.8(2) . . ?
N1 C5 C10 109.2(3) . . ?
N1 C5 C11 110.5(3) . . ?
C4 C5 C10 113.9(2) . . ?
C4 C5 C11 112.5(3) . . ?
C11 C5 C10 110.4(3) . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C3 C8 H8 114.8 . . ?
C9 C8 C3 130.4(3) . . ?
C9 C8 H8 114.8 . . ?
Br2 C9 Br1 112.73(17) . . ?
C8 C9 Br1 120.7(3) . . ?
C8 C9 Br2 126.5(3) . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C11 H11A 109.5 . . ?
C5 C11 H11B 109.5 . . ?
C5 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C2 C3 -178.5(3) . . . . ?
O1 N1 C2 C6 -60.3(4) . . . . ?
O1 N1 C2 C7 61.2(4) . . . . ?
O1 N1 C5 C4 177.9(3) . . . . ?
O1 N1 C5 C10 58.2(4) . . . . ?
O1 N1 C5 C11 -63.4(4) . . . . ?
N1 C2 C3 C4 2.3(3) . . . . ?
N1 C2 C3 C8 -177.0(3) . . . . ?
C2 N1 C5 C4 2.1(3) . . . . ?
C2 N1 C5 C10 -117.6(3) . . . . ?
C2 N1 C5 C11 120.7(3) . . . . ?
C2 C3 C4 C5 -1.2(4) . . . . ?
C2 C3 C8 C9 -169.2(3) . . . . ?
C3 C4 C5 N1 -0.5(3) . . . . ?
C3 C4 C5 C10 115.7(3) . . . . ?
C3 C4 C5 C11 -117.6(3) . . . . ?
C3 C8 C9 Br1 -180.0(3) . . . . ?
C3 C8 C9 Br2 1.2(5) . . . . ?
C4 C3 C8 C9 11.6(6) . . . . ?
C5 N1 C2 C3 -2.7(3) . . . . ?
C5 N1 C2 C6 115.5(3) . . . . ?
C5 N1 C2 C7 -123.0(3) . . . . ?
C6 C2 C3 C4 -113.6(3) . . . . ?
C6 C2 C3 C8 67.1(4) . . . . ?
C7 C2 C3 C4 119.0(3) . . . . ?
C7 C2 C3 C8 -60.3(4) . . . . ?
C8 C3 C4 C5 178.0(3) . . . . ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Hexane'
