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

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

data_2016sot0060_d1_100k
_database_code_depnum_ccdc_archive 'CCDC 1500038'
_audit_update_record             
;
2016-08-19 deposited with the CCDC.	2021-05-05 downloaded from the CCDC.
;
_audit_creation_date             2016-08-19
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.08.15 svn.r3327 for OlexSys, GUI svn.r5212)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H18 N2 O2'
_chemical_formula_sum            'C18 H18 N2 O2'
_chemical_formula_weight         294.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   22.0147(2)
_cell_length_b                   4.41720(10)
_cell_length_c                   31.4419(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.5880(10)
_cell_angle_gamma                90
_cell_volume                     3023.23(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    22867
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.9830
_cell_measurement_theta_min      2.0100
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.684
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1248
_exptl_crystal_recrystallization_method 
'The material was recrystallised from ethanol by slow evaporation'
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            58425
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.337
_diffrn_reflns_theta_min         2.030
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 22.2222
_diffrn_detector_type            'Rigaku HG Saturn944+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00  77.00   1.00   10.00    --  -13.00  60.00-120.00  180
  2  ω      6.00  49.00   1.00   10.00    --  -13.00  45.00  60.00   43
  3  ω     -5.00  48.00   1.00   10.00    --  -13.00  37.00  30.00   53
  4  ω     21.00  41.00   1.00   10.00    --  -13.00  37.00 -90.00   20
  5  ω     26.00  46.00   1.00   10.00    --  -13.00  45.00  90.00   20
  6  ω     51.00  71.00   1.00   10.00    --  -13.00  45.00-180.00   20
  7  ω   -179.00   0.00   1.00   40.00    --  -90.00  37.00 -30.00  179
  8  ω   -149.00   0.00   1.00   40.00    --  -90.00  60.00  60.00  149
  9  ω   -162.00   0.00   1.00   40.00    --  -90.00  60.00  30.00  162
 10  ω   -153.00   0.00   1.00   40.00    --  -90.00  60.00  90.00  153
 11  ω   -169.00 -95.00   1.00   40.00    --  -90.00  60.00 -90.00   74
 12  ω   -153.00   0.00   1.00   40.00    --  -90.00  60.00 -30.00  153
 13  ω   -126.00   0.00   1.00   40.00    --  -90.00  60.00   0.00  126
 14  ω   -124.00   0.00   1.00   40.00    --  -90.00   0.00 -30.00  124
 15  ω   -162.00   0.00   1.00   40.00    --  -90.00  52.00 -30.00  162
 16  ω   -104.00   0.00   1.00   40.00    --  -90.00  52.00   0.00  104
 17  ω   -107.00   0.00   1.00   40.00    --  -90.00  45.00  30.00  107
 18  ω    -49.00   0.00   1.00   40.00    --  -90.00  52.00  60.00   49
 19  ω   -112.00   0.00   1.00   40.00    --  -90.00  52.00  90.00  112
 20  ω   -128.00 -69.00   1.00   40.00    --  -90.00  52.00 -90.00   59
 21  ω    -20.00   0.00   1.00   40.00    --  -90.00  52.00  30.00   20
 22  ω   -163.00 -28.00   1.00   40.00    --  -90.00  15.00 120.00  135
 23  ω    -38.00  -2.00   1.00   40.00    --  -90.00  45.00   0.00   36
 24  ω    -20.00   0.00   1.00   40.00    --  -90.00  45.00  60.00   20
 25  ω    -20.00   0.00   1.00   40.00    --  -90.00  45.00 -30.00   20
 26  ω    -20.00   0.00   1.00   40.00    --  -90.00  45.00  90.00   20
 27  ω   -102.00 -78.00   1.00   40.00    --  -90.00  52.00 -60.00   24
 28  ω    -84.00 -18.00   1.00   40.00    --  -90.00  30.00  90.00   66
 29  ω    -20.00   0.00   1.00   40.00    --  -90.00  37.00  60.00   20
 30  ω    -20.00   0.00   1.00   40.00    --  -90.00  60.00 -60.00   20
;
_diffrn_measurement_device       'three-circle quarter χ goniometer'
_diffrn_measurement_device_type  'Rigaku AFC11 007-HF'
_diffrn_measurement_device_type2 'Rigaku AFC11'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0522206000
_diffrn_orient_matrix_UB_12      -0.0705648000
_diffrn_orient_matrix_UB_13      0.0370059000
_diffrn_orient_matrix_UB_21      0.0446801000
_diffrn_orient_matrix_UB_22      -0.0454943000
_diffrn_orient_matrix_UB_23      -0.0327780000
_diffrn_orient_matrix_UB_31      0.0169069000
_diffrn_orient_matrix_UB_32      0.3385436000
_diffrn_orient_matrix_UB_33      0.0033003000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           40.0
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4923
_reflns_number_total             5761
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.20
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
;
_computing_data_collection       'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_computing_data_reduction        
;
'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.450
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     413
_refine_ls_number_reflns         5761
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0454
_refine_ls_restrained_S_all      1.030
_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)+(0.0568P)²+1.5446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1150
_refine_ls_wR_factor_ref         0.1211
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C107(H10C,H10D), C112(H11A,H11B), C207(H20C,H20D), C212(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C101(H10A), C102(H10B), C103(H103), C104(H104), C105(H105), C108(H108),
 C109(H109), C114(H114), C115(H115), C116(H116), C117(H117), C118(H118),
 C201(H20A), C202(H20B), C203(H203), C204(H204), C205(H205), C208(H208),
 C209(H209), C214(H214), C215(H215), C216(H216), C217(H217), C218(H218)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O101 O 0.67227(5) 0.7924(3) 0.46967(3) 0.0343(3) Uani 1 1 d . . . . .
O102 O 0.61167(5) 0.3149(3) 0.54233(3) 0.0358(3) Uani 1 1 d . . . . .
N101 N 0.48882(6) 1.0197(4) 0.43344(4) 0.0353(3) Uani 1 1 d . . . . .
N102 N 0.70966(6) 0.3773(3) 0.52954(4) 0.0287(3) Uani 1 1 d . . . . .
C101 C 0.49639(8) 0.9997(4) 0.32974(5) 0.0397(4) Uani 1 1 d . . . . .
H10A H 0.5374 1.0673 0.3379 0.048 Uiso 1 1 calc R . . . .
C102 C 0.48078(8) 0.8385(5) 0.29210(6) 0.0422(4) Uani 1 1 d . . . . .
H10B H 0.5112 0.7936 0.2745 0.051 Uiso 1 1 calc R . . . .
C103 C 0.42102(8) 0.7425(5) 0.27994(6) 0.0419(4) Uani 1 1 d . . . . .
H103 H 0.4102 0.6338 0.2538 0.050 Uiso 1 1 calc R . . . .
C104 C 0.37694(8) 0.8043(5) 0.30567(6) 0.0425(4) Uani 1 1 d . . . . .
H104 H 0.3359 0.7369 0.2973 0.051 Uiso 1 1 calc R . . . .
C105 C 0.39225(8) 0.9628(4) 0.34331(6) 0.0388(4) Uani 1 1 d . . . . .
H105 H 0.3616 1.0034 0.3608 0.047 Uiso 1 1 calc R . . . .
C106 C 0.45163(8) 1.0644(4) 0.35614(5) 0.0357(4) Uani 1 1 d . . . . .
C107 C 0.46931(8) 1.2297(4) 0.39812(5) 0.0378(4) Uani 1 1 d . . . . .
H10C H 0.5032 1.3724 0.3954 0.045 Uiso 1 1 calc R . . . .
H10D H 0.4338 1.3489 0.4047 0.045 Uiso 1 1 calc R . . . .
C108 C 0.54649(7) 0.9431(4) 0.44567(5) 0.0325(4) Uani 1 1 d . . . . .
H108 H 0.5766 1.0465 0.4324 0.039 Uiso 1 1 calc R . . . .
C109 C 0.56737(7) 0.7260(4) 0.47601(5) 0.0312(4) Uani 1 1 d . . . . .
H109 H 0.5389 0.6145 0.4897 0.037 Uiso 1 1 calc R . . . .
C110 C 0.63099(7) 0.6696(4) 0.48665(5) 0.0284(3) Uani 1 1 d . . . . .
C111 C 0.64972(7) 0.4348(4) 0.52228(5) 0.0283(3) Uani 1 1 d . . . . .
C112 C 0.73653(7) 0.1474(4) 0.55973(5) 0.0325(4) Uani 1 1 d . . . . .
H11A H 0.7671 0.0305 0.5464 0.039 Uiso 1 1 calc R . . . .
H11B H 0.7038 0.0055 0.5653 0.039 Uiso 1 1 calc R . . . .
C113 C 0.76745(7) 0.2743(4) 0.60202(5) 0.0303(3) Uani 1 1 d . . . . .
C114 C 0.73661(7) 0.4708(4) 0.62601(5) 0.0331(4) Uani 1 1 d . . . . .
H114 H 0.6958 0.5314 0.6152 0.040 Uiso 1 1 calc R . . . .
C115 C 0.76457(8) 0.5792(4) 0.66542(5) 0.0388(4) Uani 1 1 d . . . . .
H115 H 0.7431 0.7142 0.6814 0.047 Uiso 1 1 calc R . . . .
C116 C 0.82390(8) 0.4907(5) 0.68153(6) 0.0423(4) Uani 1 1 d . . . . .
H116 H 0.8433 0.5652 0.7085 0.051 Uiso 1 1 calc R . . . .
C117 C 0.85476(8) 0.2939(5) 0.65818(6) 0.0430(4) Uani 1 1 d . . . . .
H117 H 0.8953 0.2312 0.6693 0.052 Uiso 1 1 calc R . . . .
C118 C 0.82693(7) 0.1875(4) 0.61860(5) 0.0375(4) Uani 1 1 d . . . . .
H118 H 0.8487 0.0539 0.6026 0.045 Uiso 1 1 calc R . . . .
O201 O 0.82097(5) 0.6366(3) 0.50771(3) 0.0332(3) Uani 1 1 d . . . . .
O202 O 0.88182(5) 1.1709(3) 0.44265(3) 0.0334(3) Uani 1 1 d . . . . .
N201 N 1.00284(6) 0.5432(3) 0.56353(4) 0.0317(3) Uani 1 1 d . . . . .
N202 N 0.78292(6) 1.0360(3) 0.44618(4) 0.0289(3) Uani 1 1 d . . . . .
C201 C 1.09163(8) 0.3984(5) 0.66697(6) 0.0476(5) Uani 1 1 d . . . . .
H20A H 1.1209 0.2705 0.6567 0.057 Uiso 1 1 calc R . . . .
C202 C 1.10434(10) 0.5234(6) 0.70787(7) 0.0607(7) Uani 1 1 d . . . . .
H20B H 1.1423 0.4801 0.7254 0.073 Uiso 1 1 calc R . . . .
C203 C 1.06240(11) 0.7092(6) 0.72314(6) 0.0570(6) Uani 1 1 d . . . . .
H203 H 1.0715 0.7948 0.7511 0.068 Uiso 1 1 calc R . . . .
C204 C 1.00762(10) 0.7704(5) 0.69804(6) 0.0494(5) Uani 1 1 d . . . . .
H204 H 0.9785 0.8974 0.7087 0.059 Uiso 1 1 calc R . . . .
C205 C 0.99443(8) 0.6489(4) 0.65731(5) 0.0379(4) Uani 1 1 d . . . . .
H205 H 0.9563 0.6947 0.6401 0.045 Uiso 1 1 calc R . . . .
C206 C 1.03620(7) 0.4599(4) 0.64107(5) 0.0344(4) Uani 1 1 d . . . . .
C207 C 1.02069(8) 0.3194(4) 0.59710(5) 0.0358(4) Uani 1 1 d . . . . .
H20C H 1.0568 0.2058 0.5903 0.043 Uiso 1 1 calc R . . . .
H20D H 0.9866 0.1734 0.5974 0.043 Uiso 1 1 calc R . . . .
C208 C 0.94554(7) 0.5841(4) 0.54507(5) 0.0313(4) Uani 1 1 d . . . . .
H208 H 0.9154 0.4565 0.5544 0.038 Uiso 1 1 calc R . . . .
C209 C 0.92483(7) 0.7926(4) 0.51362(5) 0.0302(3) Uani 1 1 d . . . . .
H209 H 0.9525 0.9326 0.5040 0.036 Uiso 1 1 calc R . . . .
C210 C 0.86176(7) 0.7962(4) 0.49586(5) 0.0280(3) Uani 1 1 d . . . . .
C211 C 0.84328(7) 1.0220(4) 0.45874(5) 0.0279(3) Uani 1 1 d . . . . .
C212 C 0.75389(7) 1.2392(4) 0.41267(5) 0.0313(3) Uani 1 1 d . . . . .
H21A H 0.7829 1.4043 0.4086 0.038 Uiso 1 1 calc R . . . .
H21B H 0.7172 1.3318 0.4222 0.038 Uiso 1 1 calc R . . . .
C213 C 0.73466(7) 1.0817(4) 0.37004(5) 0.0301(3) Uani 1 1 d . . . . .
C214 C 0.68285(7) 0.8977(4) 0.36331(5) 0.0362(4) Uani 1 1 d . . . . .
H214 H 0.6595 0.8662 0.3860 0.043 Uiso 1 1 calc R . . . .
C215 C 0.66493(8) 0.7603(5) 0.32396(6) 0.0434(4) Uani 1 1 d . . . . .
H215 H 0.6295 0.6350 0.3198 0.052 Uiso 1 1 calc R . . . .
C216 C 0.69852(9) 0.8044(5) 0.29047(6) 0.0458(5) Uani 1 1 d . . . . .
H216 H 0.6861 0.7106 0.2634 0.055 Uiso 1 1 calc R . . . .
C217 C 0.74995(9) 0.9853(5) 0.29690(6) 0.0481(5) Uani 1 1 d . . . . .
H217 H 0.7731 1.0169 0.2741 0.058 Uiso 1 1 calc R . . . .
C218 C 0.76817(8) 1.1218(5) 0.33641(5) 0.0406(4) Uani 1 1 d . . . . .
H218 H 0.8040 1.2444 0.3405 0.049 Uiso 1 1 calc R . . . .
H202 H 0.7597(8) 0.917(5) 0.4603(6) 0.038(5) Uiso 1 1 d . . . . .
H201 H 1.0341(9) 0.668(5) 0.5547(6) 0.050(6) Uiso 1 1 d . . . . .
H102 H 0.7345(9) 0.481(5) 0.5139(7) 0.052(6) Uiso 1 1 d . . . . .
H101 H 0.4568(11) 0.908(6) 0.4469(7) 0.070(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O101 C110 1.2448(18) . ?
O102 C111 1.2399(18) . ?
N101 C107 1.461(2) . ?
N101 C108 1.315(2) . ?
N101 H101 1.00(2) . ?
N102 C111 1.330(2) . ?
N102 C112 1.454(2) . ?
N102 H102 0.91(2) . ?
C101 H10A 0.9500 . ?
C101 C102 1.380(2) . ?
C101 C106 1.409(2) . ?
C102 H10B 0.9500 . ?
C102 C103 1.381(2) . ?
C103 H103 0.9500 . ?
C103 C104 1.380(3) . ?
C104 H104 0.9500 . ?
C104 C105 1.373(3) . ?
C105 H105 0.9500 . ?
C105 C106 1.384(2) . ?
C106 C107 1.508(2) . ?
C107 H10C 0.9900 . ?
C107 H10D 0.9900 . ?
C108 H108 0.9500 . ?
C108 C109 1.382(2) . ?
C109 H109 0.9500 . ?
C109 C110 1.413(2) . ?
C110 C111 1.537(2) . ?
C112 H11A 0.9900 . ?
C112 H11B 0.9900 . ?
C112 C113 1.508(2) . ?
C113 C114 1.392(2) . ?
C113 C118 1.389(2) . ?
C114 H114 0.9500 . ?
C114 C115 1.384(2) . ?
C115 H115 0.9500 . ?
C115 C116 1.385(2) . ?
C116 H116 0.9500 . ?
C116 C117 1.380(3) . ?
C117 H117 0.9500 . ?
C117 C118 1.385(2) . ?
C118 H118 0.9500 . ?
O201 C210 1.2418(19) . ?
O202 C211 1.2397(18) . ?
N201 C207 1.457(2) . ?
N201 C208 1.320(2) . ?
N201 H201 0.95(2) . ?
N202 C211 1.3299(19) . ?
N202 C212 1.457(2) . ?
N202 H202 0.89(2) . ?
C201 H20A 0.9500 . ?
C201 C202 1.389(3) . ?
C201 C206 1.389(2) . ?
C202 H20B 0.9500 . ?
C202 C203 1.374(3) . ?
C203 H203 0.9500 . ?
C203 C204 1.366(3) . ?
C204 H204 0.9500 . ?
C204 C205 1.379(2) . ?
C205 H205 0.9500 . ?
C205 C206 1.394(2) . ?
C206 C207 1.507(2) . ?
C207 H20C 0.9900 . ?
C207 H20D 0.9900 . ?
C208 H208 0.9500 . ?
C208 C209 1.378(2) . ?
C209 H209 0.9500 . ?
C209 C210 1.417(2) . ?
C210 C211 1.543(2) . ?
C212 H21A 0.9900 . ?
C212 H21B 0.9900 . ?
C212 C213 1.514(2) . ?
C213 C214 1.391(2) . ?
C213 C218 1.388(2) . ?
C214 H214 0.9500 . ?
C214 C215 1.382(2) . ?
C215 H215 0.9500 . ?
C215 C216 1.388(3) . ?
C216 H216 0.9500 . ?
C216 C217 1.376(3) . ?
C217 H217 0.9500 . ?
C217 C218 1.385(3) . ?
C218 H218 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
C107 N101 H101 119.1(14) . . ?
C108 N101 C107 123.16(15) . . ?
C108 N101 H101 117.3(14) . . ?
C111 N102 C112 122.82(14) . . ?
C111 N102 H102 118.1(13) . . ?
C112 N102 H102 119.0(13) . . ?
C102 C101 H10A 119.9 . . ?
C102 C101 C106 120.22(16) . . ?
C106 C101 H10A 119.9 . . ?
C101 C102 H10B 120.0 . . ?
C101 C102 C103 120.06(17) . . ?
C103 C102 H10B 120.0 . . ?
C102 C103 H103 120.0 . . ?
C104 C103 C102 120.08(17) . . ?
C104 C103 H103 120.0 . . ?
C103 C104 H104 119.9 . . ?
C105 C104 C103 120.17(17) . . ?
C105 C104 H104 119.9 . . ?
C104 C105 H105 119.5 . . ?
C104 C105 C106 121.07(16) . . ?
C106 C105 H105 119.5 . . ?
C101 C106 C107 120.14(15) . . ?
C105 C106 C101 118.40(16) . . ?
C105 C106 C107 121.42(15) . . ?
N101 C107 C106 111.46(15) . . ?
N101 C107 H10C 109.3 . . ?
N101 C107 H10D 109.3 . . ?
C106 C107 H10C 109.3 . . ?
C106 C107 H10D 109.3 . . ?
H10C C107 H10D 108.0 . . ?
N101 C108 H108 117.0 . . ?
N101 C108 C109 125.98(16) . . ?
C109 C108 H108 117.0 . . ?
C108 C109 H109 119.9 . . ?
C108 C109 C110 120.10(15) . . ?
C110 C109 H109 119.9 . . ?
O101 C110 C109 125.67(15) . . ?
O101 C110 C111 118.22(13) . . ?
C109 C110 C111 116.11(13) . . ?
O102 C111 N102 124.04(15) . . ?
O102 C111 C110 122.05(14) . . ?
N102 C111 C110 113.91(13) . . ?
N102 C112 H11A 108.8 . . ?
N102 C112 H11B 108.8 . . ?
N102 C112 C113 113.69(14) . . ?
H11A C112 H11B 107.7 . . ?
C113 C112 H11A 108.8 . . ?
C113 C112 H11B 108.8 . . ?
C114 C113 C112 121.15(14) . . ?
C118 C113 C112 120.28(15) . . ?
C118 C113 C114 118.52(15) . . ?
C113 C114 H114 119.6 . . ?
C115 C114 C113 120.90(15) . . ?
C115 C114 H114 119.6 . . ?
C114 C115 H115 120.0 . . ?
C114 C115 C116 119.92(17) . . ?
C116 C115 H115 120.0 . . ?
C115 C116 H116 120.1 . . ?
C117 C116 C115 119.70(16) . . ?
C117 C116 H116 120.1 . . ?
C116 C117 H117 119.8 . . ?
C116 C117 C118 120.33(16) . . ?
C118 C117 H117 119.8 . . ?
C113 C118 H118 119.7 . . ?
C117 C118 C113 120.63(17) . . ?
C117 C118 H118 119.7 . . ?
C207 N201 H201 118.3(12) . . ?
C208 N201 C207 123.26(15) . . ?
C208 N201 H201 118.5(12) . . ?
C211 N202 C212 123.66(14) . . ?
C211 N202 H202 116.4(12) . . ?
C212 N202 H202 119.9(12) . . ?
C202 C201 H20A 119.9 . . ?
C206 C201 H20A 119.9 . . ?
C206 C201 C202 120.2(2) . . ?
C201 C202 H20B 119.7 . . ?
C203 C202 C201 120.51(18) . . ?
C203 C202 H20B 119.7 . . ?
C202 C203 H203 120.1 . . ?
C204 C203 C202 119.85(19) . . ?
C204 C203 H203 120.1 . . ?
C203 C204 H204 119.8 . . ?
C203 C204 C205 120.3(2) . . ?
C205 C204 H204 119.8 . . ?
C204 C205 H205 119.5 . . ?
C204 C205 C206 120.96(17) . . ?
C206 C205 H205 119.5 . . ?
C201 C206 C205 118.17(17) . . ?
C201 C206 C207 121.07(17) . . ?
C205 C206 C207 120.74(15) . . ?
N201 C207 C206 112.63(14) . . ?
N201 C207 H20C 109.1 . . ?
N201 C207 H20D 109.1 . . ?
C206 C207 H20C 109.1 . . ?
C206 C207 H20D 109.1 . . ?
H20C C207 H20D 107.8 . . ?
N201 C208 H208 116.6 . . ?
N201 C208 C209 126.82(16) . . ?
C209 C208 H208 116.6 . . ?
C208 C209 H209 120.3 . . ?
C208 C209 C210 119.33(15) . . ?
C210 C209 H209 120.3 . . ?
O201 C210 C209 125.82(15) . . ?
O201 C210 C211 118.24(13) . . ?
C209 C210 C211 115.94(13) . . ?
O202 C211 N202 124.65(15) . . ?
O202 C211 C210 122.17(13) . . ?
N202 C211 C210 113.17(13) . . ?
N202 C212 H21A 109.0 . . ?
N202 C212 H21B 109.0 . . ?
N202 C212 C213 113.05(14) . . ?
H21A C212 H21B 107.8 . . ?
C213 C212 H21A 109.0 . . ?
C213 C212 H21B 109.0 . . ?
C214 C213 C212 121.20(14) . . ?
C218 C213 C212 120.38(15) . . ?
C218 C213 C214 118.41(15) . . ?
C213 C214 H214 119.6 . . ?
C215 C214 C213 120.73(16) . . ?
C215 C214 H214 119.6 . . ?
C214 C215 H215 119.9 . . ?
C214 C215 C216 120.29(17) . . ?
C216 C215 H215 119.9 . . ?
C215 C216 H216 120.3 . . ?
C217 C216 C215 119.35(17) . . ?
C217 C216 H216 120.3 . . ?
C216 C217 H217 119.8 . . ?
C216 C217 C218 120.42(17) . . ?
C218 C217 H217 119.8 . . ?
C213 C218 H218 119.6 . . ?
C217 C218 C213 120.79(17) . . ?
C217 C218 H218 119.6 . . ?

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
N202 H202 O101 0.89(2) 2.066(19) 2.8592(17) 147.2(17) .
N201 H201 O202 0.95(2) 1.97(2) 2.8684(17) 155.4(18) 3_776
N102 H102 O201 0.91(2) 2.06(2) 2.8792(17) 148.9(18) .
N101 H101 O102 1.00(2) 1.87(2) 2.8568(18) 166(2) 3_666

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
O101 C110 C111 O102 176.01(14) . . . . ?
O101 C110 C111 N102 -3.3(2) . . . . ?
N101 C108 C109 C110 -178.95(15) . . . . ?
N102 C112 C113 C114 52.8(2) . . . . ?
N102 C112 C113 C118 -129.59(16) . . . . ?
C101 C102 C103 C104 -0.8(3) . . . . ?
C101 C106 C107 N101 -88.81(19) . . . . ?
C102 C101 C106 C105 -0.1(3) . . . . ?
C102 C101 C106 C107 177.56(17) . . . . ?
C102 C103 C104 C105 0.4(3) . . . . ?
C103 C104 C105 C106 0.2(3) . . . . ?
C104 C105 C106 C101 -0.4(3) . . . . ?
C104 C105 C106 C107 -177.97(17) . . . . ?
C105 C106 C107 N101 88.74(19) . . . . ?
C106 C101 C102 C103 0.6(3) . . . . ?
C107 N101 C108 C109 -173.69(16) . . . . ?
C108 N101 C107 C106 93.18(19) . . . . ?
C108 C109 C110 O101 -3.0(3) . . . . ?
C108 C109 C110 C111 177.18(14) . . . . ?
C109 C110 C111 O102 -4.2(2) . . . . ?
C109 C110 C111 N102 176.51(14) . . . . ?
C111 N102 C112 C113 -102.61(17) . . . . ?
C112 N102 C111 O102 5.1(2) . . . . ?
C112 N102 C111 C110 -175.60(13) . . . . ?
C112 C113 C114 C115 177.98(16) . . . . ?
C112 C113 C118 C117 -177.49(16) . . . . ?
C113 C114 C115 C116 -0.4(3) . . . . ?
C114 C113 C118 C117 0.1(3) . . . . ?
C114 C115 C116 C117 -0.2(3) . . . . ?
C115 C116 C117 C118 0.7(3) . . . . ?
C116 C117 C118 C113 -0.7(3) . . . . ?
C118 C113 C114 C115 0.4(3) . . . . ?
O201 C210 C211 O202 -173.83(14) . . . . ?
O201 C210 C211 N202 5.7(2) . . . . ?
N201 C208 C209 C210 177.06(15) . . . . ?
N202 C212 C213 C214 75.92(19) . . . . ?
N202 C212 C213 C218 -105.03(18) . . . . ?
C201 C202 C203 C204 0.4(3) . . . . ?
C201 C206 C207 N201 -127.14(17) . . . . ?
C202 C201 C206 C205 0.1(3) . . . . ?
C202 C201 C206 C207 -178.19(17) . . . . ?
C202 C203 C204 C205 -0.6(3) . . . . ?
C203 C204 C205 C206 0.6(3) . . . . ?
C204 C205 C206 C201 -0.3(3) . . . . ?
C204 C205 C206 C207 177.97(17) . . . . ?
C205 C206 C207 N201 54.6(2) . . . . ?
C206 C201 C202 C203 -0.1(3) . . . . ?
C207 N201 C208 C209 179.10(15) . . . . ?
C208 N201 C207 C206 -105.53(18) . . . . ?
C208 C209 C210 O201 4.4(2) . . . . ?
C208 C209 C210 C211 -176.01(14) . . . . ?
C209 C210 C211 O202 6.6(2) . . . . ?
C209 C210 C211 N202 -173.91(14) . . . . ?
C211 N202 C212 C213 102.01(17) . . . . ?
C212 N202 C211 O202 -2.6(2) . . . . ?
C212 N202 C211 C210 177.93(13) . . . . ?
C212 C213 C214 C215 178.56(16) . . . . ?
C212 C213 C218 C217 -178.19(17) . . . . ?
C213 C214 C215 C216 -0.1(3) . . . . ?
C214 C213 C218 C217 0.9(3) . . . . ?
C214 C215 C216 C217 0.2(3) . . . . ?
C215 C216 C217 C218 0.1(3) . . . . ?
C216 C217 C218 C213 -0.7(3) . . . . ?
C218 C213 C214 C215 -0.5(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_submission    2016-08-12
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id 'DCW/7964/218.3 '
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.515
_oxdiff_exptl_absorpt_empirical_full_min 0.437
####################################################################### 
# 
# 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_2020sot0020_k1_100k
_database_code_depnum_ccdc_archive 'CCDC 2042398'
_audit_update_record             
;
2020-11-04 deposited with the CCDC.	2021-05-05 downloaded from the CCDC.
;
_audit_creation_date             2020-11-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
rb2u17@soton.ac.uk
light@soton.ac.uk
dch2@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H25 Br N2 O3'
_chemical_formula_sum            'C18 H25 Br N2 O3'
_chemical_formula_weight         397.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H25 Br N2 O3'
_chemical_oxdiff_usercomment     rb/9071/23.7p
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.7511(2)
_cell_length_b                   10.26090(10)
_cell_length_c                   12.1428(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.8170(10)
_cell_angle_gamma                90
_cell_volume                     1828.46(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10180
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8710
_cell_measurement_theta_min      3.3570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.266
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       '(cut) plate'
_exptl_crystal_F_000             824
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 0 -1 0.0177
-5 0 1 0.0177
1 5 -4 0.0332
-1 -5 4 0.0332
-1 3 5 0.0601
1 -3 -5 0.0601

_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of DCM and hexane  by slow evaporation'
_exptl_crystal_size_max          0.139
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.035
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
4.9942 -0.0017 -0.9977 0.2027 -0.1063 0.0795
-4.9942 0.0017 0.9977 -0.2027 0.1063 -0.0795
1.0066 4.9924 -3.9916 -0.1550 -0.3426 0.1805
-1.0066 -4.9924 3.9916 0.1550 0.3426 -0.1805
-1.0050 2.9961 4.9923 -0.0591 -0.1505 -0.3200
1.0050 -2.9961 -4.9923 0.0591 0.1505 0.3200

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29540
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.239
_diffrn_reflns_theta_min         3.031
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  66.00   1.00    5.00    --  -22.50  38.00 -60.00  120
  2  ω   -111.00  12.00   1.00    5.00    --  -22.50 -60.00-180.00  123
  3  ω    -57.00  66.00   1.00    5.00    --  -22.50  60.00   0.00  123
  4  ω   -111.00  12.00   1.00    5.00    --  -22.50 -60.00 120.00  123
  5  ω    -57.00  43.00   1.00    5.00    --  -22.50  60.00 -90.00  100
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-HF'
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0433924000
_diffrn_orient_matrix_UB_12      -0.0285745000
_diffrn_orient_matrix_UB_13      0.0140453000
_diffrn_orient_matrix_UB_21      -0.0207094000
_diffrn_orient_matrix_UB_22      -0.0620909000
_diffrn_orient_matrix_UB_23      0.0029519000
_diffrn_orient_matrix_UB_31      0.0045244000
_diffrn_orient_matrix_UB_32      -0.0103275000
_diffrn_orient_matrix_UB_33      -0.0569913000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5061
_reflns_number_total             6123
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         6123
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.056
_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)+(0.0300P)²+1.0415P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0801
_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.a Ternary CH refined with riding coordinates:
 C13(H13), C16(H16)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.45110(2) 0.49724(2) 0.84549(2) 0.01947(5) Uani 1 1 d . . . . .
O1 O 0.80949(8) 0.68563(11) 0.30593(9) 0.0161(2) Uani 1 1 d . . . . .
O2 O 0.89150(8) 0.45832(12) 0.24149(9) 0.0171(2) Uani 1 1 d . . . . .
O3 O 0.73696(8) 0.26359(11) 0.29077(9) 0.0159(2) Uani 1 1 d . . . . .
N1 N 0.66301(9) 0.63600(12) 0.45590(11) 0.0140(3) Uani 1 1 d . . . . .
N2 N 0.85291(9) 0.26305(12) 0.43144(10) 0.0126(2) Uani 1 1 d . . . . .
C1 C 0.51343(11) 0.53276(15) 0.71900(12) 0.0135(3) Uani 1 1 d . . . . .
C2 C 0.48028(11) 0.62891(15) 0.64583(13) 0.0147(3) Uani 1 1 d . . . . .
H2 H 0.425080 0.672822 0.656176 0.018 Uiso 1 1 calc R U . . .
C3 C 0.52858(10) 0.66061(15) 0.55699(13) 0.0139(3) Uani 1 1 d . . . . .
H3 H 0.505538 0.725252 0.505554 0.017 Uiso 1 1 calc R U . . .
C4 C 0.61103(10) 0.59795(14) 0.54271(12) 0.0123(3) Uani 1 1 d . . . . .
C5 C 0.64282(11) 0.50088(15) 0.61812(13) 0.0150(3) Uani 1 1 d . . . . .
H5 H 0.698658 0.457838 0.609374 0.018 Uiso 1 1 calc R U . . .
C6 C 0.59366(11) 0.46681(15) 0.70557(13) 0.0157(3) Uani 1 1 d . . . . .
H6 H 0.614683 0.399384 0.755373 0.019 Uiso 1 1 calc R U . . .
C7 C 0.64130(13) 0.76129(16) 0.40076(15) 0.0212(3) Uani 1 1 d . . . . .
H7A H 0.586657 0.751546 0.348377 0.032 Uiso 1 1 calc R U . . .
H7B H 0.692561 0.788734 0.360829 0.032 Uiso 1 1 calc R U . . .
H7C H 0.630216 0.827133 0.456299 0.032 Uiso 1 1 calc R U . . .
C8 C 0.71926(11) 0.54831(15) 0.41327(12) 0.0130(3) Uani 1 1 d . . . . .
H8 H 0.713098 0.461409 0.438456 0.016 Uiso 1 1 calc R U . . .
C9 C 0.78273(11) 0.56420(14) 0.34075(13) 0.0135(3) Uani 1 1 d . . . . .
C10 C 0.83177(10) 0.45140(15) 0.30448(12) 0.0126(3) Uani 1 1 d . . . . .
C11 C 0.80308(10) 0.31585(15) 0.34380(12) 0.0119(3) Uani 1 1 d . . . . .
C12 C 0.78588(12) 0.71125(17) 0.19018(14) 0.0209(3) Uani 1 1 d . . . . .
H12A H 0.817107 0.648705 0.146113 0.031 Uiso 1 1 calc R U . . .
H12B H 0.804597 0.799963 0.172925 0.031 Uiso 1 1 calc R U . . .
H12C H 0.719839 0.702562 0.172599 0.031 Uiso 1 1 calc R U . . .
C13 C 0.93320(11) 0.33136(16) 0.48831(13) 0.0158(3) Uani 1 1 d . . . . .
H13 H 0.934161 0.421046 0.456229 0.019 Uiso 1 1 calc R U . . .
C14 C 0.92523(13) 0.34651(19) 0.61225(14) 0.0246(4) Uani 1 1 d . . . . .
H14A H 0.868036 0.391011 0.623147 0.037 Uiso 1 1 calc R U . . .
H14B H 0.976693 0.397965 0.646055 0.037 Uiso 1 1 calc R U . . .
H14C H 0.925847 0.260254 0.646979 0.037 Uiso 1 1 calc R U . . .
C15 C 1.02091(12) 0.2644(2) 0.46425(17) 0.0290(4) Uani 1 1 d . . . . .
H15A H 1.021706 0.175177 0.493083 0.043 Uiso 1 1 calc R U . . .
H15B H 1.073174 0.312676 0.500033 0.043 Uiso 1 1 calc R U . . .
H15C H 1.024440 0.262221 0.384111 0.043 Uiso 1 1 calc R U . . .
C16 C 0.83267(11) 0.12858(15) 0.46830(13) 0.0157(3) Uani 1 1 d . . . . .
H16 H 0.878817 0.107889 0.531999 0.019 Uiso 1 1 calc R U . . .
C17 C 0.73944(12) 0.12178(17) 0.51216(14) 0.0206(3) Uani 1 1 d . . . . .
H17A H 0.736107 0.187225 0.570387 0.031 Uiso 1 1 calc R U . . .
H17B H 0.730536 0.034798 0.542617 0.031 Uiso 1 1 calc R U . . .
H17C H 0.691791 0.138939 0.451635 0.031 Uiso 1 1 calc R U . . .
C18 C 0.84486(13) 0.02754(16) 0.37858(15) 0.0208(3) Uani 1 1 d . . . . .
H18A H 0.797860 0.040240 0.316470 0.031 Uiso 1 1 calc R U . . .
H18B H 0.839303 -0.060189 0.409087 0.031 Uiso 1 1 calc R U . . .
H18C H 0.905233 0.037750 0.352621 0.031 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 C1 1.9035(15) . ?
O1 C9 1.3860(18) . ?
O1 C12 1.4376(19) . ?
O2 C10 1.2259(19) . ?
O3 C11 1.2355(18) . ?
N1 C4 1.4196(19) . ?
N1 C7 1.470(2) . ?
N1 C8 1.361(2) . ?
N2 C11 1.3445(19) . ?
N2 C13 1.4849(19) . ?
N2 C16 1.4902(19) . ?
C1 C2 1.383(2) . ?
C1 C6 1.387(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.402(2) . ?
C4 C5 1.401(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.390(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C9 1.359(2) . ?
C9 C10 1.457(2) . ?
C10 C11 1.544(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13 1.0000 . ?
C13 C14 1.529(2) . ?
C13 C15 1.519(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 1.0000 . ?
C16 C17 1.526(2) . ?
C16 C18 1.528(2) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C12 114.48(12) . . ?
C4 N1 C7 118.02(13) . . ?
C8 N1 C4 119.77(13) . . ?
C8 N1 C7 121.20(13) . . ?
C11 N2 C13 121.62(13) . . ?
C11 N2 C16 120.04(13) . . ?
C13 N2 C16 118.17(12) . . ?
C2 C1 Br1 119.12(12) . . ?
C2 C1 C6 121.51(15) . . ?
C6 C1 Br1 119.28(12) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.31(14) . . ?
C3 C2 H2 120.3 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.53(14) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 N1 120.42(13) . . ?
C5 C4 N1 120.70(14) . . ?
C5 C4 C3 118.83(14) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.81(15) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.98(14) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 H8 114.6 . . ?
C9 C8 N1 130.83(14) . . ?
C9 C8 H8 114.6 . . ?
O1 C9 C10 117.17(14) . . ?
C8 C9 O1 122.82(14) . . ?
C8 C9 C10 119.78(14) . . ?
O2 C10 C9 123.57(15) . . ?
O2 C10 C11 118.82(14) . . ?
C9 C10 C11 117.54(13) . . ?
O3 C11 N2 125.25(14) . . ?
O3 C11 C10 117.17(13) . . ?
N2 C11 C10 117.57(13) . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13 107.2 . . ?
N2 C13 C14 111.61(13) . . ?
N2 C13 C15 110.60(14) . . ?
C14 C13 H13 107.2 . . ?
C15 C13 H13 107.2 . . ?
C15 C13 C14 112.78(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16 106.7 . . ?
N2 C16 C17 111.24(13) . . ?
N2 C16 C18 111.87(13) . . ?
C17 C16 H16 106.7 . . ?
C17 C16 C18 113.16(14) . . ?
C18 C16 H16 106.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
Br1 C1 C2 C3 176.15(11) . . . . ?
Br1 C1 C6 C5 -174.67(12) . . . . ?
O1 C9 C10 O2 -3.6(2) . . . . ?
O1 C9 C10 C11 179.41(13) . . . . ?
O2 C10 C11 O3 -94.36(18) . . . . ?
O2 C10 C11 N2 84.40(18) . . . . ?
N1 C4 C5 C6 177.63(14) . . . . ?
N1 C8 C9 O1 8.4(3) . . . . ?
N1 C8 C9 C10 -177.39(15) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
C2 C3 C4 N1 -176.14(14) . . . . ?
C2 C3 C4 C5 1.4(2) . . . . ?
C3 C4 C5 C6 0.1(2) . . . . ?
C4 N1 C8 C9 -171.30(16) . . . . ?
C4 C5 C6 C1 -1.6(2) . . . . ?
C6 C1 C2 C3 -0.2(2) . . . . ?
C7 N1 C4 C3 15.3(2) . . . . ?
C7 N1 C4 C5 -162.18(15) . . . . ?
C7 N1 C8 C9 20.5(3) . . . . ?
C8 N1 C4 C3 -153.29(14) . . . . ?
C8 N1 C4 C5 29.2(2) . . . . ?
C8 C9 C10 O2 -178.11(15) . . . . ?
C8 C9 C10 C11 4.9(2) . . . . ?
C9 C10 C11 O3 82.81(17) . . . . ?
C9 C10 C11 N2 -98.43(16) . . . . ?
C11 N2 C13 C14 125.03(16) . . . . ?
C11 N2 C13 C15 -108.54(17) . . . . ?
C11 N2 C16 C17 -66.13(18) . . . . ?
C11 N2 C16 C18 61.52(18) . . . . ?
C12 O1 C9 C8 -114.44(17) . . . . ?
C12 O1 C9 C10 71.20(17) . . . . ?
C13 N2 C11 O3 178.13(14) . . . . ?
C13 N2 C11 C10 -0.5(2) . . . . ?
C13 N2 C16 C17 118.56(15) . . . . ?
C13 N2 C16 C18 -113.79(15) . . . . ?
C16 N2 C11 O3 3.0(2) . . . . ?
C16 N2 C11 C10 -175.66(13) . . . . ?
C16 N2 C13 C14 -59.74(18) . . . . ?
C16 N2 C13 C15 66.69(18) . . . . ?

_olex2_date_sample_data_collection 2020-10-29
_olex2_date_sample_submission    2020-10-21
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with silicon oil'
_olex2_submission_original_sample_id rb/9071/23.7p
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.625
_oxdiff_exptl_absorpt_empirical_full_min 0.555
####################################################################### 
# 
# 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_2020sot0037_r1_100k
_database_code_depnum_ccdc_archive 'CCDC 2059384'
loop_
_audit_author_name
_audit_author_address
'Mark E Light'
;University of Southampton
United Kingdom
;
_audit_update_record             
;
2021-01-28 deposited with the CCDC.	2021-05-05 downloaded from the CCDC.
;
_audit_creation_date             2021-01-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
rb2u17@soton.ac.uk
light@soton.ac.uk
dch2@soton.ac.uk
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H30 N2 O3'
_chemical_formula_sum            'C16 H30 N2 O3'
_chemical_formula_weight         298.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H30N2O3
_chemical_oxdiff_usercomment     rb/9071/23.61p
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                   6.0189(3)
_cell_length_b                   10.6268(6)
_cell_length_c                   14.7651(6)
_cell_angle_alpha                70.260(4)
_cell_angle_beta                 88.043(4)
_cell_angle_gamma                78.758(4)
_cell_volume                     871.33(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6867
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.7840
_cell_measurement_theta_min      2.0600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49291
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.37a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             328
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 -1 0.0495
0 0 1 0.0495
-5 -2 2 0.1310
5 2 -2 0.1310
1 5 3 0.0184
-1 -5 -3 0.0184

_exptl_crystal_recrystallization_method 
'The material was recrystallised from a mixture of diethyl ether and hexane  by slow evaporation'
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.037
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0001 0.0008 -0.9991 0.0032 -0.0509 0.0020
0.0001 -0.0008 0.9991 -0.0032 0.0509 -0.0020
-4.9973 -1.9955 1.9995 -0.0408 0.1045 -0.5929
4.9973 1.9955 -1.9995 0.0408 -0.1045 0.5929
1.0005 4.9963 3.0020 0.3165 0.0593 0.1080
-1.0005 -4.9963 -3.0020 -0.3165 -0.0593 -0.1080

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0885
_diffrn_reflns_av_unetI/netI     0.0618
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            19535
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.497
_diffrn_reflns_theta_min         2.076
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  63.00   0.50    5.00    --  -13.40  43.00-150.63  238
  2  ω   -100.00 -30.00   0.50    5.00    --  -13.40 -19.00 -60.00  140
  3  ω     -4.00  58.00   0.50    5.00    --  -13.40 -19.00 -60.00  124
  4  ω    -87.00  -1.00   0.50    5.00    --  -13.40 -60.00-180.00  172
  5  ω    -67.00  22.00   0.50    5.00    --  -13.40 -60.00  30.00  178
  6  ω    -49.00 -16.00   0.50    5.00    --  -13.40  57.00 -60.00   66
  7  ω    -12.00  35.00   0.50    5.00    --  -13.40  57.00 -60.00   94
  8  ω     38.00  73.00   0.50    5.00    --  -13.40  57.00 -60.00   70
  9  ω   -102.00   6.00   0.50    5.00    --  -13.40 -60.00 -90.00  216
 10  ω    -49.00  71.00   0.50    5.00    --  -13.40  60.00  90.00  240
 11  ω    -55.00  -5.00   0.50    5.00    --  -13.40  44.00  11.06  100
;
_diffrn_measurement_device       'four-circle κ diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 FRE-VHF'
_diffrn_measurement_device_type2 'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0207968000
_diffrn_orient_matrix_UB_12      0.0694041000
_diffrn_orient_matrix_UB_13      -0.0031379000
_diffrn_orient_matrix_UB_21      0.0075442000
_diffrn_orient_matrix_UB_22      -0.0202430000
_diffrn_orient_matrix_UB_23      0.0509315000
_diffrn_orient_matrix_UB_31      0.1181694000
_diffrn_orient_matrix_UB_32      -0.0008355000
_diffrn_orient_matrix_UB_33      -0.0020197000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FR-E+ SuperBright'
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3425
_reflns_number_total             4390
_reflns_odcompleteness_completeness 99.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.64
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.37a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         4390
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.050
_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)+(0.0744P)²+0.0199P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1290
_refine_ls_wR_factor_ref         0.1367
_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.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,
 H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C),
 C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.87293(12) 0.24297(8) 0.35968(6) 0.01671(19) Uani 1 1 d . . . . .
O2 O 1.07787(13) 0.44733(9) 0.23188(6) 0.0224(2) Uani 1 1 d . . . . .
O3 O 0.82492(15) 0.68390(9) 0.29553(6) 0.0250(2) Uani 1 1 d . . . . .
N1 N 0.44962(16) 0.36493(10) 0.43705(7) 0.0207(2) Uani 1 1 d . . . . .
N2 N 0.67195(16) 0.69548(9) 0.15338(7) 0.0170(2) Uani 1 1 d . . . . .
C1 C 0.5325(3) 0.23211(15) 0.50868(10) 0.0374(4) Uani 1 1 d . . . . .
H1A H 0.524953 0.239904 0.571672 0.056 Uiso 1 1 calc R U . . .
H1B H 0.686728 0.199354 0.496329 0.056 Uiso 1 1 calc R U . . .
H1C H 0.440517 0.169346 0.505360 0.056 Uiso 1 1 calc R U . . .
C2 C 0.2266(2) 0.43213(15) 0.45501(9) 0.0259(3) Uani 1 1 d . . . . .
H2A H 0.116066 0.380303 0.450466 0.039 Uiso 1 1 calc R U . . .
H2B H 0.189538 0.521963 0.408112 0.039 Uiso 1 1 calc R U . . .
H2C H 0.226963 0.438520 0.518326 0.039 Uiso 1 1 calc R U . . .
C3 C 0.56713(18) 0.42700(12) 0.36284(8) 0.0172(2) Uani 1 1 d . . . . .
H3 H 0.504001 0.518018 0.330541 0.021 Uiso 1 1 calc R U . . .
C4 C 0.76550(18) 0.37935(11) 0.32602(8) 0.0158(2) Uani 1 1 d . . . . .
C5 C 0.88764(18) 0.47591(11) 0.26236(8) 0.0166(2) Uani 1 1 d . . . . .
C6 C 0.78712(19) 0.62868(12) 0.23822(8) 0.0175(2) Uani 1 1 d . . . . .
C7 C 0.82814(19) 0.15791(12) 0.30469(8) 0.0191(3) Uani 1 1 d . . . . .
C8 C 0.9540(2) 0.01689(13) 0.36367(10) 0.0275(3) Uani 1 1 d . . . . .
H8A H 1.112469 0.017846 0.367776 0.041 Uiso 1 1 calc R U . . .
H8B H 0.933834 -0.047233 0.333342 0.041 Uiso 1 1 calc R U . . .
H8C H 0.895416 -0.009239 0.427220 0.041 Uiso 1 1 calc R U . . .
C9 C 0.5748(2) 0.16208(16) 0.29640(11) 0.0319(3) Uani 1 1 d . . . . .
H9A H 0.517671 0.125722 0.359476 0.048 Uiso 1 1 calc R U . . .
H9B H 0.549619 0.108497 0.258210 0.048 Uiso 1 1 calc R U . . .
H9C H 0.497588 0.254642 0.266308 0.048 Uiso 1 1 calc R U . . .
C10 C 0.9274(2) 0.20384(13) 0.20565(9) 0.0251(3) Uani 1 1 d . . . . .
H10A H 0.846490 0.293072 0.168854 0.038 Uiso 1 1 calc R U . . .
H10B H 0.914101 0.140953 0.173238 0.038 Uiso 1 1 calc R U . . .
H10C H 1.084370 0.206525 0.212254 0.038 Uiso 1 1 calc R U . . .
C11 C 0.63489(19) 0.62726(12) 0.08478(8) 0.0178(2) Uani 1 1 d . . . . .
H11 H 0.697277 0.529840 0.115221 0.021 Uiso 1 1 calc R U . . .
C12 C 0.38244(19) 0.64181(13) 0.06442(9) 0.0230(3) Uani 1 1 d . . . . .
H12A H 0.310423 0.602815 0.123547 0.034 Uiso 1 1 calc R U . . .
H12B H 0.363190 0.595148 0.020621 0.034 Uiso 1 1 calc R U . . .
H12C H 0.314992 0.736605 0.036286 0.034 Uiso 1 1 calc R U . . .
C13 C 0.7627(2) 0.67810(14) -0.00696(9) 0.0239(3) Uani 1 1 d . . . . .
H13A H 0.703292 0.773166 -0.039352 0.036 Uiso 1 1 calc R U . . .
H13B H 0.744827 0.627659 -0.048387 0.036 Uiso 1 1 calc R U . . .
H13C H 0.920656 0.665567 0.008977 0.036 Uiso 1 1 calc R U . . .
C14 C 0.5859(2) 0.84429(12) 0.12482(9) 0.0206(3) Uani 1 1 d . . . . .
H14 H 0.509939 0.872523 0.061461 0.025 Uiso 1 1 calc R U . . .
C15 C 0.4076(2) 0.87942(14) 0.19252(10) 0.0301(3) Uani 1 1 d . . . . .
H15A H 0.297673 0.822091 0.202036 0.045 Uiso 1 1 calc R U . . .
H15B H 0.333647 0.973160 0.164960 0.045 Uiso 1 1 calc R U . . .
H15C H 0.478884 0.865196 0.253295 0.045 Uiso 1 1 calc R U . . .
C16 C 0.7780(2) 0.92284(13) 0.11221(10) 0.0273(3) Uani 1 1 d . . . . .
H16A H 0.857382 0.898285 0.172886 0.041 Uiso 1 1 calc R U . . .
H16B H 0.716622 1.018925 0.089546 0.041 Uiso 1 1 calc R U . . .
H16C H 0.880992 0.900770 0.066259 0.041 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 C4 1.3912(13) . ?
O1 C7 1.4678(14) . ?
O2 C5 1.2358(14) . ?
O3 C6 1.2299(14) . ?
N1 C1 1.4536(16) . ?
N1 C2 1.4532(16) . ?
N1 C3 1.3329(15) . ?
N2 C6 1.3493(14) . ?
N2 C11 1.4750(15) . ?
N2 C14 1.4806(14) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C4 1.3724(16) . ?
C4 C5 1.4395(15) . ?
C5 C6 1.5394(16) . ?
C7 C8 1.5162(16) . ?
C7 C9 1.5248(16) . ?
C7 C10 1.5184(17) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9800 . ?
C11 C12 1.5268(15) . ?
C11 C13 1.5216(16) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9800 . ?
C14 C15 1.5209(19) . ?
C14 C16 1.5248(16) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C7 116.70(8) . . ?
C2 N1 C1 114.42(10) . . ?
C3 N1 C1 124.69(11) . . ?
C3 N1 C2 120.79(10) . . ?
C6 N2 C11 122.64(10) . . ?
C6 N2 C14 119.59(10) . . ?
C11 N2 C14 117.73(8) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3 114.5 . . ?
N1 C3 C4 130.93(11) . . ?
C4 C3 H3 114.5 . . ?
O1 C4 C5 117.77(10) . . ?
C3 C4 O1 122.43(9) . . ?
C3 C4 C5 118.94(10) . . ?
O2 C5 C4 125.42(10) . . ?
O2 C5 C6 116.27(9) . . ?
C4 C5 C6 117.97(10) . . ?
O3 C6 N2 123.84(11) . . ?
O3 C6 C5 118.02(10) . . ?
N2 C6 C5 118.06(10) . . ?
O1 C7 C8 103.11(9) . . ?
O1 C7 C9 111.09(10) . . ?
O1 C7 C10 110.03(9) . . ?
C8 C7 C9 111.56(10) . . ?
C8 C7 C10 110.09(10) . . ?
C10 C7 C9 110.71(10) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11 107.4 . . ?
N2 C11 C12 111.22(10) . . ?
N2 C11 C13 111.07(9) . . ?
C12 C11 H11 107.4 . . ?
C13 C11 H11 107.4 . . ?
C13 C11 C12 112.21(9) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14 106.6 . . ?
N2 C14 C15 111.76(10) . . ?
N2 C14 C16 111.85(10) . . ?
C15 C14 H14 106.6 . . ?
C15 C14 C16 112.87(11) . . ?
C16 C14 H14 106.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 C4 C5 O2 2.91(17) . . . . ?
O1 C4 C5 C6 -170.12(9) . . . . ?
O2 C5 C6 O3 -90.54(13) . . . . ?
O2 C5 C6 N2 86.37(13) . . . . ?
N1 C3 C4 O1 5.83(19) . . . . ?
N1 C3 C4 C5 -163.29(11) . . . . ?
C1 N1 C3 C4 11.7(2) . . . . ?
C2 N1 C3 C4 -171.93(12) . . . . ?
C3 C4 C5 O2 172.53(10) . . . . ?
C3 C4 C5 C6 -0.49(16) . . . . ?
C4 O1 C7 C8 -176.01(9) . . . . ?
C4 O1 C7 C9 -56.38(12) . . . . ?
C4 O1 C7 C10 66.58(12) . . . . ?
C4 C5 C6 O3 83.12(13) . . . . ?
C4 C5 C6 N2 -99.97(12) . . . . ?
C6 N2 C11 C12 121.33(11) . . . . ?
C6 N2 C11 C13 -112.92(12) . . . . ?
C6 N2 C14 C15 -64.49(13) . . . . ?
C6 N2 C14 C16 63.17(14) . . . . ?
C7 O1 C4 C3 96.99(12) . . . . ?
C7 O1 C4 C5 -93.77(11) . . . . ?
C11 N2 C6 O3 178.18(10) . . . . ?
C11 N2 C6 C5 1.46(15) . . . . ?
C11 N2 C14 C15 117.94(11) . . . . ?
C11 N2 C14 C16 -114.40(11) . . . . ?
C14 N2 C6 O3 0.73(17) . . . . ?
C14 N2 C6 C5 -175.98(9) . . . . ?
C14 N2 C11 C12 -61.18(12) . . . . ?
C14 N2 C11 C13 64.57(13) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder in perfluoroether oil'
_olex2_submission_original_sample_id rb/9071/23.61p
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.011
_oxdiff_exptl_absorpt_empirical_full_min 0.254
