# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_testm1
_database_code_depnum_ccdc_archive 'CCDC 1993726'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_audit_creation_date             2018-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 N3 O, H2 O'
_chemical_formula_sum            'C14 H19 N3 O2'
_chemical_formula_weight         261.32
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1323(2)
_cell_length_b                   8.1695(2)
_cell_length_c                   19.3253(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.8030(10)
_cell_angle_gamma                90
_cell_volume                     1283.79(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4478
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.884
_cell_measurement_theta_min      2.707
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6403
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0480 before and 0.0355 after correction. The Ratio of minimum to maximum transmission is 0.8588. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.492
_exptl_crystal_size_mid          0.406
_exptl_crystal_size_min          0.373
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11411
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.902
_diffrn_reflns_theta_min         2.505
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2749
_reflns_number_total             3068
_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       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_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         0.453
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3068
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0507
_refine_ls_R_factor_gt           0.0448
_refine_ls_restrained_S_all      1.119
_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)+(0.0339P)²+1.0698P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1067
_refine_special_details          
;
The NH hydrogen atom was located in the difference map however
restraints were applied to the NH distance as it appears that
it and the H2O hydrogen atoms are probably disordered.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N3-H3
 0.87 with sigma of 0.01
3.a Free rotating group:
 O2(H2A,H2B)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.80261(14) 0.21176(13) 0.55608(5) 0.0183(2) Uani 1 1 d . . . . .
N1 N 0.78348(15) 0.40200(14) 0.46810(6) 0.0124(2) Uani 1 1 d . . . . .
N2 N 0.87075(15) 0.15080(14) 0.44225(6) 0.0126(2) Uani 1 1 d . . . . .
N3 N 0.91686(15) 0.17789(17) 0.32251(7) 0.0173(3) Uani 1 1 d D . . . .
C1 C 0.81628(17) 0.25350(18) 0.49566(7) 0.0133(3) Uani 1 1 d . . . . .
C2 C 0.78538(16) 0.39918(16) 0.39192(7) 0.0107(3) Uani 1 1 d . . . . .
C3 C 0.86769(16) 0.23468(17) 0.37923(7) 0.0109(3) Uani 1 1 d . . . . .
C4 C 0.60864(16) 0.38842(17) 0.36160(7) 0.0107(3) Uani 1 1 d . . . . .
C5 C 0.50272(16) 0.25212(17) 0.37226(7) 0.0115(3) Uani 1 1 d . . . . .
C6 C 0.52754(17) 0.10581(17) 0.42119(7) 0.0130(3) Uani 1 1 d . . . . .
H6A H 0.418661 0.053929 0.427234 0.016 Uiso 1 1 calc R . . . .
H6B H 0.561388 0.150273 0.466862 0.016 Uiso 1 1 calc R . . . .
C7 C 0.65060(18) -0.03238(17) 0.40307(7) 0.0143(3) Uani 1 1 d . . . . .
H7A H 0.599437 -0.139360 0.413523 0.017 Uiso 1 1 calc R . . . .
H7B H 0.671579 -0.029026 0.352756 0.017 Uiso 1 1 calc R . . . .
C8 C 0.81542(18) -0.02052(17) 0.44227(7) 0.0141(3) Uani 1 1 d . . . . .
H8A H 0.802393 -0.059109 0.490443 0.017 Uiso 1 1 calc R . . . .
H8B H 0.898177 -0.090561 0.419626 0.017 Uiso 1 1 calc R . . . .
C9 C 0.72580(18) 0.53969(18) 0.50809(8) 0.0164(3) Uani 1 1 d . . . . .
H9A H 0.697195 0.502676 0.554635 0.025 Uiso 1 1 calc GR . . . .
H9B H 0.628458 0.587083 0.485325 0.025 Uiso 1 1 calc GR . . . .
H9C H 0.812666 0.622572 0.511408 0.025 Uiso 1 1 calc GR . . . .
C10 C 0.88878(18) 0.53922(17) 0.36398(8) 0.0147(3) Uani 1 1 d . . . . .
H10A H 0.838538 0.643907 0.376578 0.022 Uiso 1 1 calc GR . . . .
H10B H 0.894238 0.530813 0.313482 0.022 Uiso 1 1 calc GR . . . .
H10C H 1.000076 0.533034 0.383917 0.022 Uiso 1 1 calc GR . . . .
C11 C 0.55290(18) 0.51790(18) 0.32040(7) 0.0144(3) Uani 1 1 d . . . . .
H11 H 0.623296 0.609117 0.313571 0.017 Uiso 1 1 calc R . . . .
C12 C 0.39834(18) 0.51813(19) 0.28904(7) 0.0173(3) Uani 1 1 d . . . . .
H12 H 0.362178 0.609942 0.262776 0.021 Uiso 1 1 calc R . . . .
C13 C 0.29777(18) 0.3833(2) 0.29649(7) 0.0173(3) Uani 1 1 d . . . . .
H13 H 0.193524 0.379414 0.273742 0.021 Uiso 1 1 calc R . . . .
C14 C 0.35041(17) 0.25357(18) 0.33753(7) 0.0148(3) Uani 1 1 d . . . . .
H14 H 0.279968 0.161608 0.342268 0.018 Uiso 1 1 calc R . . . .
O2 O 0.90250(15) 0.12550(14) 0.69510(6) 0.0212(3) Uani 1 1 d . . . . .
H2A H 0.959060 0.039565 0.683613 0.032 Uiso 1 1 d G . . . .
H2B H 0.863022 0.162658 0.656094 0.032 Uiso 1 1 d G . . . .
H3 H 0.910(4) 0.239(3) 0.2861(11) 0.085(11) Uiso 1 1 d D . . A 1


_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 C1 1.2229(17) . ?
N1 C1 1.3500(18) . ?
N1 C2 1.4727(17) . ?
N1 C9 1.4466(18) . ?
N2 C1 1.4066(18) . ?
N2 C3 1.3974(17) . ?
N2 C8 1.4701(18) . ?
N3 C3 1.2605(19) . ?
N3 H3 0.862(10) . ?
C2 C3 1.5227(19) . ?
C2 C4 1.5471(18) . ?
C2 C10 1.5232(19) . ?
C4 C5 1.4244(19) . ?
C4 C11 1.3959(19) . ?
C5 C6 1.5357(19) . ?
C5 C14 1.4005(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5519(19) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.533(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C12 1.388(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.380(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(2) . ?
C14 H14 0.9500 . ?
O2 H2A 0.8699 . ?
O2 H2B 0.8699 . ?

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
C1 N1 C2 112.06(11) . . ?
C1 N1 C9 123.49(12) . . ?
C9 N1 C2 123.66(11) . . ?
C1 N2 C8 117.92(12) . . ?
C3 N2 C1 110.19(11) . . ?
C3 N2 C8 117.73(11) . . ?
C3 N3 H3 119(2) . . ?
O1 C1 N1 127.38(13) . . ?
O1 C1 N2 124.62(13) . . ?
N1 C1 N2 108.00(12) . . ?
N1 C2 C3 100.70(10) . . ?
N1 C2 C4 110.90(11) . . ?
N1 C2 C10 110.87(11) . . ?
C3 C2 C4 107.28(11) . . ?
C3 C2 C10 111.08(11) . . ?
C10 C2 C4 115.02(11) . . ?
N2 C3 C2 107.15(11) . . ?
N3 C3 N2 125.13(13) . . ?
N3 C3 C2 127.62(13) . . ?
C5 C4 C2 123.38(12) . . ?
C11 C4 C2 117.74(12) . . ?
C11 C4 C5 118.86(12) . . ?
C4 C5 C6 128.53(12) . . ?
C14 C5 C4 117.17(12) . . ?
C14 C5 C6 114.17(12) . . ?
C5 C6 H6A 107.2 . . ?
C5 C6 H6B 107.2 . . ?
C5 C6 C7 120.46(11) . . ?
H6A C6 H6B 106.8 . . ?
C7 C6 H6A 107.2 . . ?
C7 C6 H6B 107.2 . . ?
C6 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 C6 113.87(11) . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
N2 C8 C7 108.99(11) . . ?
N2 C8 H8A 109.9 . . ?
N2 C8 H8B 109.9 . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11 118.8 . . ?
C12 C11 C4 122.34(13) . . ?
C12 C11 H11 118.8 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.19(13) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.37(13) . . ?
C14 C13 H13 120.3 . . ?
C5 C14 H14 118.5 . . ?
C13 C14 C5 122.95(14) . . ?
C13 C14 H14 118.5 . . ?
H2A O2 H2B 104.5 . . ?

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
O2 H2A N3 0.87 2.05 2.9037(17) 167.9 3_756 yes
O2 H2B O1 0.87 2.03 2.8834(15) 167.6 . yes
N3 H3 O2 0.862(10) 2.080(10) 2.9407(18) 176(3) 4_565 yes

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM:Et2O'
####################################################################### 
# 
# 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_mm121
_database_code_depnum_ccdc_archive 'CCDC 1993728'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_audit_creation_date             2019-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H15 N3 O2, H2 O'
_chemical_formula_sum            'C13 H17 N3 O3'
_chemical_formula_weight         263.29
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.0314(2)
_cell_length_b                   8.1488(2)
_cell_length_c                   19.2027(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.5479(17)
_cell_angle_gamma                90
_cell_volume                     1256.69(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7467
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.04
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0543 before and 0.0462 after correction. The Ratio of minimum to maximum transmission is 0.9052. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM:Et2O'
_exptl_crystal_size_max          0.394
_exptl_crystal_size_mid          0.347
_exptl_crystal_size_min          0.144
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26526
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.573
_diffrn_reflns_theta_min         2.121
_diffrn_ambient_temperature      99.97
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3045
_reflns_number_total             3522
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3522
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.049
_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)+(0.0473P)²+0.4771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.0998
_refine_special_details          
;
 Hydrogen atoms on heteroatoms were found by difference map after all other
 atoms had been refined. All other hydrogen atoms were placed geometrically
 and refined using a riding model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.39242(12) 0.37161(12) 0.36451(5) 0.01294(19) Uani 1 1 d . . . . .
C2 C 0.45075(13) 0.48908(14) 0.31790(5) 0.0179(2) Uani 1 1 d . . . . .
H2 H 0.3824 0.5806 0.3065 0.022 Uiso 1 1 calc R . . . .
C3 C 0.60714(14) 0.47510(15) 0.28766(6) 0.0224(2) Uani 1 1 d . . . . .
H3 H 0.6460 0.5587 0.2574 0.027 Uiso 1 1 calc R . . . .
C4 C 0.70591(14) 0.33961(16) 0.30166(6) 0.0225(2) Uani 1 1 d . . . . .
H4 H 0.8101 0.3273 0.2793 0.027 Uiso 1 1 calc R . . . .
C5 C 0.65212(13) 0.22155(14) 0.34861(6) 0.0193(2) Uani 1 1 d . . . . .
H5 H 0.7203 0.1291 0.3587 0.023 Uiso 1 1 calc R . . . .
C6 C 0.49853(12) 0.23863(13) 0.38079(5) 0.01404(19) Uani 1 1 d . . . . .
C7 C 0.38052(14) -0.02555(13) 0.41410(6) 0.0177(2) Uani 1 1 d . . . . .
H7A H 0.4504 -0.1192 0.4293 0.021 Uiso 1 1 calc R . . . .
H7B H 0.3654 -0.0317 0.3629 0.021 Uiso 1 1 calc R . . . .
C8 C 0.21058(14) -0.03146(13) 0.45028(6) 0.0182(2) Uani 1 1 d . . . . .
H8A H 0.1366 -0.1110 0.4263 0.022 Uiso 1 1 calc R . . . .
H8B H 0.2250 -0.0668 0.4993 0.022 Uiso 1 1 calc R . . . .
C9 C 0.19255(12) 0.24363(13) 0.49966(5) 0.0158(2) Uani 1 1 d . . . . .
C10 C 0.21447(12) 0.38285(12) 0.39380(5) 0.01253(18) Uani 1 1 d . . . . .
C11 C 0.13605(12) 0.21356(12) 0.38314(5) 0.01304(19) Uani 1 1 d . . . . .
C12 C 0.27259(14) 0.53428(13) 0.50865(6) 0.0185(2) Uani 1 1 d . . . . .
H12A H 0.3695 0.5819 0.4855 0.028 Uiso 1 1 calc GR . . . .
H12B H 0.3036 0.5017 0.5562 0.028 Uiso 1 1 calc GR . . . .
H12C H 0.1830 0.6158 0.5103 0.028 Uiso 1 1 calc GR . . . .
C13 C 0.10940(13) 0.51961(13) 0.36226(6) 0.0173(2) Uani 1 1 d . . . . .
H13A H -0.0022 0.5171 0.3824 0.026 Uiso 1 1 calc GR . . . .
H13B H 0.1009 0.5042 0.3117 0.026 Uiso 1 1 calc GR . . . .
H13C H 0.1617 0.6258 0.3723 0.026 Uiso 1 1 calc GR . . . .
N1 N 0.13668(11) 0.13337(11) 0.44766(4) 0.01526(18) Uani 1 1 d . . . . .
N2 N 0.21594(11) 0.39175(11) 0.47018(4) 0.01463(18) Uani 1 1 d . . . . .
N3 N 0.08841(11) 0.14745(12) 0.32689(5) 0.01800(19) Uani 1 1 d . . . . .
H3A H 0.095(2) 0.207(2) 0.2931(9) 0.036(4) Uiso 1 1 d . . . . .
O1 O 0.45937(9) 0.12820(9) 0.43333(4) 0.01589(16) Uani 1 1 d . . . . .
O2 O 0.21082(11) 0.20726(11) 0.56102(4) 0.02251(18) Uani 1 1 d . . . . .
O3 O 0.08826(12) 0.15247(11) 0.69733(4) 0.02492(19) Uani 1 1 d . . . . .
H3B H 0.135(2) 0.185(2) 0.6604(10) 0.039(5) Uiso 1 1 d . . . . .
H3C H 0.029(3) 0.054(3) 0.6867(12) 0.071(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
C1 C2 1.3946(14) . ?
C1 C6 1.4118(14) . ?
C1 C10 1.5437(13) . ?
C2 H2 0.9500 . ?
C2 C3 1.3935(15) . ?
C3 H3 0.9500 . ?
C3 C4 1.3844(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3901(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3919(14) . ?
C6 O1 1.3902(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5381(15) . ?
C7 O1 1.4500(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 N1 1.4691(14) . ?
C9 N1 1.4132(13) . ?
C9 N2 1.3471(14) . ?
C9 O2 1.2224(13) . ?
C10 C11 1.5294(14) . ?
C10 C13 1.5202(14) . ?
C10 N2 1.4685(12) . ?
C11 N1 1.4007(13) . ?
C11 N3 1.2631(13) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12 N2 1.4475(13) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N3 H3A 0.813(18) . ?
O3 H3B 0.848(19) . ?
O3 H3C 0.95(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 117.60(9) . . ?
C2 C1 C10 120.73(9) . . ?
C6 C1 C10 121.59(9) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.40(10) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.09(10) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.79(10) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.06(10) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.93(9) . . ?
O1 C6 C1 121.15(9) . . ?
O1 C6 C5 117.71(9) . . ?
H7A C7 H7B 108.5 . . ?
C8 C7 H7A 110.2 . . ?
C8 C7 H7B 110.2 . . ?
O1 C7 H7A 110.2 . . ?
O1 C7 H7B 110.2 . . ?
O1 C7 C8 107.42(8) . . ?
C7 C8 H8A 110.0 . . ?
C7 C8 H8B 110.0 . . ?
H8A C8 H8B 108.4 . . ?
N1 C8 C7 108.41(8) . . ?
N1 C8 H8A 110.0 . . ?
N1 C8 H8B 110.0 . . ?
N2 C9 N1 108.51(9) . . ?
O2 C9 N1 124.14(10) . . ?
O2 C9 N2 127.33(10) . . ?
C11 C10 C1 106.21(8) . . ?
C13 C10 C1 114.25(8) . . ?
C13 C10 C11 112.43(8) . . ?
N2 C10 C1 111.61(8) . . ?
N2 C10 C11 100.23(8) . . ?
N2 C10 C13 111.16(8) . . ?
N1 C11 C10 107.72(8) . . ?
N3 C11 C10 128.32(9) . . ?
N3 C11 N1 123.78(10) . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 N1 C8 115.57(8) . . ?
C11 N1 C8 117.05(8) . . ?
C11 N1 C9 109.07(8) . . ?
C9 N2 C10 112.06(8) . . ?
C9 N2 C12 123.29(9) . . ?
C12 N2 C10 123.29(8) . . ?
C11 N3 H3A 113.9(12) . . ?
C6 O1 C7 118.41(8) . . ?
H3B O3 H3C 107.9(18) . . ?

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
N3 H3A O3 0.813(18) 2.167(18) 2.9746(13) 172.7(17) 4_565
O3 H3B O2 0.848(19) 2.016(19) 2.8407(11) 163.7(17) .
O3 H3C N3 0.95(2) 1.91(2) 2.8618(13) 176(2) 3_556

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
C1 C2 C3 C4 2.35(16) . . . . ?
C1 C6 O1 C7 97.59(11) . . . . ?
C1 C10 C11 N1 103.54(9) . . . . ?
C1 C10 C11 N3 -71.73(12) . . . . ?
C1 C10 N2 C9 -96.33(10) . . . . ?
C1 C10 N2 C12 70.76(12) . . . . ?
C2 C1 C6 C5 -3.22(14) . . . . ?
C2 C1 C6 O1 171.53(9) . . . . ?
C2 C1 C10 C11 130.04(10) . . . . ?
C2 C1 C10 C13 5.51(13) . . . . ?
C2 C1 C10 N2 -121.66(10) . . . . ?
C2 C3 C4 C5 -3.15(16) . . . . ?
C3 C4 C5 C6 0.76(16) . . . . ?
C4 C5 C6 C1 2.47(15) . . . . ?
C4 C5 C6 O1 -172.45(9) . . . . ?
C5 C6 O1 C7 -87.50(11) . . . . ?
C6 C1 C2 C3 0.82(15) . . . . ?
C6 C1 C10 C11 -46.59(11) . . . . ?
C6 C1 C10 C13 -171.12(9) . . . . ?
C6 C1 C10 N2 61.71(12) . . . . ?
C7 C8 N1 C9 -82.32(10) . . . . ?
C7 C8 N1 C11 48.30(12) . . . . ?
C8 C7 O1 C6 -119.52(9) . . . . ?
C10 C1 C2 C3 -175.94(9) . . . . ?
C10 C1 C6 C5 173.51(9) . . . . ?
C10 C1 C6 O1 -11.74(14) . . . . ?
C10 C11 N1 C8 -127.46(9) . . . . ?
C10 C11 N1 C9 6.13(10) . . . . ?
C11 C10 N2 C9 15.80(10) . . . . ?
C11 C10 N2 C12 -177.12(9) . . . . ?
C13 C10 C11 N1 -130.82(9) . . . . ?
C13 C10 C11 N3 53.91(13) . . . . ?
C13 C10 N2 C9 134.85(9) . . . . ?
C13 C10 N2 C12 -58.06(12) . . . . ?
N1 C9 N2 C10 -13.14(11) . . . . ?
N1 C9 N2 C12 179.78(9) . . . . ?
N2 C9 N1 C8 138.29(9) . . . . ?
N2 C9 N1 C11 3.95(11) . . . . ?
N2 C10 C11 N1 -12.70(9) . . . . ?
N2 C10 C11 N3 172.02(10) . . . . ?
N3 C11 N1 C8 48.08(14) . . . . ?
N3 C11 N1 C9 -178.33(9) . . . . ?
O1 C7 C8 N1 39.31(11) . . . . ?
O2 C9 N1 C8 -43.49(14) . . . . ?
O2 C9 N1 C11 -177.83(10) . . . . ?
O2 C9 N2 C10 168.72(10) . . . . ?
O2 C9 N2 C12 1.64(17) . . . . ?

_olex2_exptl_crystal_mounting_method 'Oil on glass fibre'
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_testo1
_database_code_depnum_ccdc_archive 'CCDC 1993733'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_audit_creation_date             2019-01-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H15 N3 O2'
_chemical_formula_sum            'C13 H15 N3 O2'
_chemical_formula_weight         245.28
_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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.4226(6)
_cell_length_b                   7.6316(4)
_cell_length_c                   22.4832(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2303.09(19)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3972
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.91
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0631 before and 0.0500 after correction. The Ratio of minimum to maximum transmission is 0.8769. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.461
_exptl_crystal_size_mid          0.284
_exptl_crystal_size_min          0.24
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            19730
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.985
_diffrn_reflns_theta_min         1.812
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2249
_reflns_number_total             2763
_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       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_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         0.334
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         2763
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.047
_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)+(0.0440P)²+1.2905P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1046
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.62233(8) 0.38847(14) 0.57578(5) 0.0211(2) Uani 1 1 d . . . . .
O2 O 0.41715(9) 0.84783(14) 0.52343(5) 0.0231(3) Uani 1 1 d . . . . .
N1 N 0.55111(9) 0.65604(15) 0.55036(5) 0.0161(3) Uani 1 1 d . . . . .
N2 N 0.46241(8) 0.46118(14) 0.60307(5) 0.0138(2) Uani 1 1 d . . . . .
N3 N 0.49515(9) 0.87081(15) 0.61624(5) 0.0171(3) Uani 1 1 d . . . . .
C1 C 0.55124(10) 0.49086(17) 0.57724(6) 0.0147(3) Uani 1 1 d . . . . .
C2 C 0.39337(10) 0.61036(17) 0.59920(6) 0.0134(3) Uani 1 1 d . . . . .
C3 C 0.46196(10) 0.74963(17) 0.56927(6) 0.0150(3) Uani 1 1 d . . . . .
C4 C 0.43345(11) 0.29033(18) 0.62549(7) 0.0216(3) Uani 1 1 d . . . . .
H4A H 0.392753 0.230051 0.595634 0.032 Uiso 1 1 calc GR . . . .
H4B H 0.394788 0.304708 0.662139 0.032 Uiso 1 1 calc GR . . . .
H4C H 0.493232 0.220831 0.633822 0.032 Uiso 1 1 calc GR . . . .
C5 C 0.29887(11) 0.56377(19) 0.56585(6) 0.0191(3) Uani 1 1 d . . . . .
H5A H 0.316171 0.507605 0.528037 0.029 Uiso 1 1 calc GR . . . .
H5B H 0.260478 0.670565 0.558059 0.029 Uiso 1 1 calc GR . . . .
H5C H 0.258848 0.483024 0.589890 0.029 Uiso 1 1 calc GR . . . .
C6 C 0.37617(10) 0.69054(17) 0.66026(6) 0.0143(3) Uani 1 1 d . . . . .
C7 C 0.31261(10) 0.63799(18) 0.70515(6) 0.0179(3) Uani 1 1 d . . . . .
H7 H 0.266990 0.544535 0.699039 0.022 Uiso 1 1 calc R . . . .
C8 C 0.31680(11) 0.72513(19) 0.75974(6) 0.0214(3) Uani 1 1 d . . . . .
H8 H 0.273641 0.691072 0.791171 0.026 Uiso 1 1 calc R . . . .
C9 C 0.38390(11) 0.86143(19) 0.76817(6) 0.0210(3) Uani 1 1 d . . . . .
H9 H 0.386623 0.918278 0.805727 0.025 Uiso 1 1 calc R . . . .
C10 C 0.44739(11) 0.91681(18) 0.72279(6) 0.0190(3) Uani 1 1 d . . . . .
H10 H 0.493008 1.010308 0.728819 0.023 Uiso 1 1 calc R . . . .
C11 C 0.44164(10) 0.83049(17) 0.66838(6) 0.0146(3) Uani 1 1 d . . . . .
C12 C 0.60436(12) 0.8770(2) 0.61734(7) 0.0269(4) Uani 1 1 d . . . . .
H12A H 0.630709 0.821087 0.653830 0.032 Uiso 1 1 calc R . . . .
H12B H 0.628536 0.999416 0.615471 0.032 Uiso 1 1 calc R . . . .
C13 C 0.63584(11) 0.7739(2) 0.56151(7) 0.0238(3) Uani 1 1 d . . . . .
H13A H 0.646765 0.853659 0.527390 0.029 Uiso 1 1 calc R . . . .
H13B H 0.697628 0.706522 0.568902 0.029 Uiso 1 1 calc R . . . .
H2 H 0.4041(14) 0.773(3) 0.4902(9) 0.038(5) 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
O1 C1 1.2338(16) . ?
O2 C3 1.4091(16) . ?
O2 H2 0.96(2) . ?
N1 C1 1.3979(17) . ?
N1 C3 1.4570(17) . ?
N1 C13 1.4717(18) . ?
N2 C1 1.3454(17) . ?
N2 C2 1.4706(16) . ?
N2 C4 1.4509(17) . ?
N3 C3 1.4727(17) . ?
N3 C11 1.4089(17) . ?
N3 C12 1.467(2) . ?
C2 C3 1.5588(18) . ?
C2 C5 1.5159(19) . ?
C2 C6 1.5207(18) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.3810(19) . ?
C6 C11 1.3951(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.397(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.389(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.395(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.3915(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.540(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 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
C3 O2 H2 109.3(12) . . ?
C1 N1 C3 108.48(10) . . ?
C1 N1 C13 118.47(12) . . ?
C3 N1 C13 106.58(11) . . ?
C1 N2 C2 113.74(11) . . ?
C1 N2 C4 122.60(11) . . ?
C4 N2 C2 123.19(11) . . ?
C11 N3 C3 107.77(11) . . ?
C11 N3 C12 120.16(12) . . ?
C12 N3 C3 109.56(11) . . ?
O1 C1 N1 124.09(12) . . ?
O1 C1 N2 126.17(13) . . ?
N2 C1 N1 109.72(11) . . ?
N2 C2 C3 100.44(10) . . ?
N2 C2 C5 112.03(11) . . ?
N2 C2 C6 110.72(10) . . ?
C5 C2 C3 116.14(11) . . ?
C5 C2 C6 114.45(11) . . ?
C6 C2 C3 101.83(10) . . ?
O2 C3 N1 113.45(11) . . ?
O2 C3 N3 108.64(10) . . ?
O2 C3 C2 115.23(11) . . ?
N1 C3 N3 105.58(11) . . ?
N1 C3 C2 106.07(10) . . ?
N3 C3 C2 107.30(10) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C2 129.55(13) . . ?
C7 C6 C11 121.05(12) . . ?
C11 C6 C2 109.30(11) . . ?
C6 C7 H7 120.7 . . ?
C6 C7 C8 118.62(13) . . ?
C8 C7 H7 120.7 . . ?
C7 C8 H8 119.9 . . ?
C9 C8 C7 120.17(14) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.55(13) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 121.1 . . ?
C11 C10 C9 117.76(13) . . ?
C11 C10 H10 121.1 . . ?
C6 C11 N3 112.30(12) . . ?
C10 C11 N3 126.86(13) . . ?
C10 C11 C6 120.82(13) . . ?
N3 C12 H12A 110.9 . . ?
N3 C12 H12B 110.9 . . ?
N3 C12 C13 104.12(12) . . ?
H12A C12 H12B 109.0 . . ?
C13 C12 H12A 110.9 . . ?
C13 C12 H12B 110.9 . . ?
N1 C13 C12 103.82(11) . . ?
N1 C13 H13A 111.0 . . ?
N1 C13 H13B 111.0 . . ?
C12 C13 H13A 111.0 . . ?
C12 C13 H13B 111.0 . . ?
H13A C13 H13B 109.0 . . ?

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
O2 H2 O1 0.96(2) 1.96(2) 2.9169(15) 177.8(18) 5_666 yes

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3:Et2O'
####################################################################### 
# 
# 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_mm102_1
_database_code_depnum_ccdc_archive 'CCDC 1993732'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_audit_creation_date             2019-03-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H23 N3 O, 1.5(H2 O)'
_chemical_formula_sum            'C18 H26 N3 O2.50'
_chemical_formula_weight         324.42
_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                   7.6118(2)
_cell_length_b                   9.3656(3)
_cell_length_c                   12.1634(4)
_cell_angle_alpha                93.7306(19)
_cell_angle_beta                 95.390(2)
_cell_angle_gamma                108.1269(18)
_cell_volume                     816.35(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5942
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.13
_cell_measurement_theta_min      2.30
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0582 before and 0.0412 after correction. The Ratio of minimum to maximum transmission is 0.8637. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             350
_exptl_crystal_size_max          0.534
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.196
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18692
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_min         1.690
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4047
_reflns_number_total             4993
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4993
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.039
_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)+(0.0567P)²+0.2838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1150
_refine_special_details          
;
 The hydrogen atoms on the nitrogen and full occupancy oxygen atom were found by
 difference map. All other hydrogens were placed geometrically and refined using
 a riding model.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: O3(0.5) H3C(0.5) H3D(0.5)
3.a Free rotating group:
 O3(H3C,H3D)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B),
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
3.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C14(H14), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.07429(14) 0.60387(11) 0.30322(9) 0.01097(19) Uani 1 1 d . . . . .
C2 C 0.06715(16) 0.70562(12) 0.40665(9) 0.0153(2) Uani 1 1 d . . . . .
H2A H 0.0131 0.6410 0.4642 0.018 Uiso 1 1 calc R . . . .
H2B H 0.1957 0.7675 0.4369 0.018 Uiso 1 1 calc R . . . .
C3 C -0.04792(17) 0.81066(14) 0.38213(10) 0.0190(2) Uani 1 1 d . . . . .
H3A H -0.0530 0.8691 0.4519 0.023 Uiso 1 1 calc R . . . .
H3B H 0.0128 0.8829 0.3306 0.023 Uiso 1 1 calc R . . . .
C4 C -0.24526(17) 0.72042(14) 0.33067(10) 0.0192(2) Uani 1 1 d . . . . .
H4A H -0.3100 0.6543 0.3846 0.023 Uiso 1 1 calc R . . . .
H4B H -0.3157 0.7903 0.3122 0.023 Uiso 1 1 calc R . . . .
C5 C -0.23882(15) 0.62483(12) 0.22597(9) 0.0147(2) Uani 1 1 d . . . . .
H5A H -0.3661 0.5579 0.1978 0.018 Uiso 1 1 calc R . . . .
H5B H -0.1919 0.6914 0.1680 0.018 Uiso 1 1 calc R . . . .
C6 C -0.18135(14) 0.38405(12) 0.25919(9) 0.01196(19) Uani 1 1 d . . . . .
C7 C -0.03777(15) 0.18306(12) 0.29679(10) 0.0151(2) Uani 1 1 d . . . . .
H7A H -0.1461 0.1221 0.3309 0.018 Uiso 1 1 calc R . . . .
H7B H 0.0763 0.1749 0.3384 0.018 Uiso 1 1 calc R . . . .
C8 C -0.05235(15) 0.11922(12) 0.17537(10) 0.0162(2) Uani 1 1 d . . . . .
H8A H -0.1452 0.1528 0.1308 0.019 Uiso 1 1 calc R . . . .
H8B H -0.1010 0.0077 0.1715 0.019 Uiso 1 1 calc R . . . .
C9 C 0.12880(16) 0.16319(12) 0.12075(10) 0.0179(2) Uani 1 1 d . . . . .
H9A H 0.2100 0.1085 0.1534 0.021 Uiso 1 1 calc R . . . .
H9B H 0.0972 0.1268 0.0409 0.021 Uiso 1 1 calc R . . . .
C10 C 0.24128(14) 0.33139(12) 0.13093(9) 0.0141(2) Uani 1 1 d . . . . .
H10A H 0.3511 0.3444 0.0903 0.017 Uiso 1 1 calc R . . . .
H10B H 0.2875 0.3656 0.2101 0.017 Uiso 1 1 calc R . . . .
C11 C 0.13229(14) 0.43336(12) 0.08624(9) 0.01217(19) Uani 1 1 d . . . . .
H11A H 0.1140 0.4178 0.0041 0.015 Uiso 1 1 calc R . . . .
H11B H 0.0078 0.4029 0.1124 0.015 Uiso 1 1 calc R . . . .
C12 C 0.22953(14) 0.59962(12) 0.12245(9) 0.01158(19) Uani 1 1 d . . . . .
C13 C 0.35422(15) 0.67831(13) 0.05279(9) 0.0153(2) Uani 1 1 d . . . . .
H13 H 0.3681 0.6261 -0.0137 0.018 Uiso 1 1 calc R . . . .
C14 C 0.45842(15) 0.82972(13) 0.07704(10) 0.0182(2) Uani 1 1 d . . . . .
H14 H 0.5419 0.8796 0.0279 0.022 Uiso 1 1 calc R . . . .
C15 C 0.43914(15) 0.90691(13) 0.17364(10) 0.0182(2) Uani 1 1 d . . . . .
H15 H 0.5099 1.0104 0.1917 0.022 Uiso 1 1 calc R . . . .
C16 C 0.31517(15) 0.83183(12) 0.24420(10) 0.0151(2) Uani 1 1 d . . . . .
H16 H 0.3029 0.8857 0.3104 0.018 Uiso 1 1 calc R . . . .
C17 C 0.20805(14) 0.67957(11) 0.22084(9) 0.01110(19) Uani 1 1 d . . . . .
C18 C 0.12029(14) 0.46617(12) 0.34229(9) 0.01149(19) Uani 1 1 d . . . . .
N1 N -0.11771(12) 0.53358(10) 0.24885(8) 0.01142(17) Uani 1 1 d . . . . .
N2 N -0.03201(12) 0.34146(10) 0.30576(8) 0.01219(18) Uani 1 1 d . . . . .
N3 N 0.26689(13) 0.46207(11) 0.40019(8) 0.01535(19) Uani 1 1 d . . . . .
H3 H 0.344(2) 0.5532(19) 0.4197(13) 0.024(4) Uiso 1 1 d . . . . .
O1 O -0.33932(11) 0.29648(9) 0.23195(7) 0.01649(17) Uani 1 1 d . . . . .
O2 O 0.53881(15) 0.75445(13) 0.57580(9) 0.0316(2) Uani 1 1 d . . . . .
H2C H 0.490(3) 0.752(2) 0.637(2) 0.055(6) Uiso 1 1 d . . . . .
H2D H 0.608(3) 0.695(2) 0.5820(17) 0.048(6) Uiso 1 1 d . . . . .
O3 O 0.3814(3) -0.0038(2) 0.53501(18) 0.0301(4) Uani 0.5 1 d . . P A -1
H3C H 0.4353 0.0702 0.4975 0.045 Uiso 0.5 1 d G . P A -1
H3D H 0.3769 0.0314 0.6022 0.045 Uiso 0.5 1 d G . P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.5436(15) . ?
C1 C17 1.5421(14) . ?
C1 C18 1.5301(14) . ?
C1 N1 1.4730(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5327(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5254(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5219(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 N1 1.4597(13) . ?
C6 N1 1.3505(14) . ?
C6 N2 1.4010(13) . ?
C6 O1 1.2265(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5375(16) . ?
C7 N2 1.4671(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5384(16) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5315(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5399(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.5162(14) . ?
C12 C13 1.3996(14) . ?
C12 C17 1.4199(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.3888(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.3830(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3926(16) . ?
C16 H16 0.9500 . ?
C16 C17 1.3997(14) . ?
C18 N2 1.3779(13) . ?
C18 N3 1.2748(14) . ?
N3 H3 0.874(17) . ?
O2 H2C 0.86(2) . ?
O2 H2D 0.89(2) . ?
O3 H3C 0.8699 . ?
O3 H3D 0.8695 . ?

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
C17 C1 C2 116.21(9) . . ?
C18 C1 C2 108.23(8) . . ?
C18 C1 C17 110.37(8) . . ?
N1 C1 C2 107.76(8) . . ?
N1 C1 C17 111.92(8) . . ?
N1 C1 C18 101.25(8) . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C3 C2 C1 113.05(9) . . ?
C3 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 C2 110.81(10) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 C3 109.93(9) . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
N1 C5 C4 110.55(9) . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C6 N2 107.90(9) . . ?
O1 C6 N1 127.90(10) . . ?
O1 C6 N2 124.19(10) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
N2 C7 H7A 109.2 . . ?
N2 C7 H7B 109.2 . . ?
N2 C7 C8 111.85(9) . . ?
C7 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
C7 C8 C9 116.37(9) . . ?
H8A C8 H8B 107.3 . . ?
C9 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
C8 C9 H9A 108.1 . . ?
C8 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?
C10 C9 C8 116.84(9) . . ?
C10 C9 H9A 108.1 . . ?
C10 C9 H9B 108.1 . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
C9 C10 C11 114.57(9) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C10 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 C10 113.09(9) . . ?
C12 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C13 C12 C11 116.05(9) . . ?
C13 C12 C17 118.13(10) . . ?
C17 C12 C11 125.81(9) . . ?
C12 C13 H13 118.7 . . ?
C14 C13 C12 122.64(11) . . ?
C14 C13 H13 118.7 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.16(10) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.49(10) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 118.9 . . ?
C15 C16 C17 122.19(11) . . ?
C17 C16 H16 118.9 . . ?
C12 C17 C1 122.36(9) . . ?
C16 C17 C1 119.24(9) . . ?
C16 C17 C12 118.39(10) . . ?
N2 C18 C1 107.00(8) . . ?
N3 C18 C1 128.49(10) . . ?
N3 C18 N2 124.48(10) . . ?
C5 N1 C1 120.70(8) . . ?
C6 N1 C1 111.94(8) . . ?
C6 N1 C5 123.65(9) . . ?
C6 N2 C7 121.21(9) . . ?
C18 N2 C6 111.06(9) . . ?
C18 N2 C7 126.98(9) . . ?
C18 N3 H3 110.8(11) . . ?
H2C O2 H2D 105.3(19) . . ?
H3C O3 H3D 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
O2 H2C O1 0.86(2) 2.05(2) 2.8918(14) 168(2) 2_566
O2 H2D N3 0.89(2) 1.99(2) 2.8717(14) 172.1(19) 2_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
C1 C2 C3 C4 56.24(13) . . . . ?
C1 C18 N2 C6 -7.42(11) . . . . ?
C1 C18 N2 C7 162.74(10) . . . . ?
C2 C1 C17 C12 179.73(9) . . . . ?
C2 C1 C17 C16 0.90(14) . . . . ?
C2 C1 C18 N2 115.53(9) . . . . ?
C2 C1 C18 N3 -62.67(14) . . . . ?
C2 C1 N1 C5 49.11(12) . . . . ?
C2 C1 N1 C6 -109.94(10) . . . . ?
C2 C3 C4 C5 -56.73(13) . . . . ?
C3 C4 C5 N1 52.76(12) . . . . ?
C4 C5 N1 C1 -52.45(13) . . . . ?
C4 C5 N1 C6 104.06(12) . . . . ?
C7 C8 C9 C10 -50.31(14) . . . . ?
C8 C7 N2 C6 62.30(13) . . . . ?
C8 C7 N2 C18 -106.95(12) . . . . ?
C8 C9 C10 C11 -56.43(14) . . . . ?
C9 C10 C11 C12 165.81(9) . . . . ?
C10 C11 C12 C13 89.20(11) . . . . ?
C10 C11 C12 C17 -89.21(12) . . . . ?
C11 C12 C13 C14 -177.65(10) . . . . ?
C11 C12 C17 C1 -1.72(16) . . . . ?
C11 C12 C17 C16 177.12(10) . . . . ?
C12 C13 C14 C15 -0.05(17) . . . . ?
C13 C12 C17 C1 179.91(9) . . . . ?
C13 C12 C17 C16 -1.26(15) . . . . ?
C13 C14 C15 C16 -0.38(17) . . . . ?
C14 C15 C16 C17 -0.04(17) . . . . ?
C15 C16 C17 C1 179.74(9) . . . . ?
C15 C16 C17 C12 0.87(16) . . . . ?
C17 C1 C2 C3 77.61(12) . . . . ?
C17 C1 C18 N2 -116.28(9) . . . . ?
C17 C1 C18 N3 65.52(14) . . . . ?
C17 C1 N1 C5 -79.85(11) . . . . ?
C17 C1 N1 C6 121.10(9) . . . . ?
C17 C12 C13 C14 0.88(16) . . . . ?
C18 C1 C2 C3 -157.60(9) . . . . ?
C18 C1 C17 C12 56.04(12) . . . . ?
C18 C1 C17 C16 -122.78(10) . . . . ?
C18 C1 N1 C5 162.60(9) . . . . ?
C18 C1 N1 C6 3.55(11) . . . . ?
N1 C1 C2 C3 -48.87(12) . . . . ?
N1 C1 C17 C12 -55.90(12) . . . . ?
N1 C1 C17 C16 125.27(10) . . . . ?
N1 C1 C18 N2 2.39(10) . . . . ?
N1 C1 C18 N3 -175.80(11) . . . . ?
N1 C6 N2 C7 -161.00(9) . . . . ?
N1 C6 N2 C18 9.81(12) . . . . ?
N2 C6 N1 C1 -8.12(11) . . . . ?
N2 C6 N1 C5 -166.44(9) . . . . ?
N2 C7 C8 C9 78.32(12) . . . . ?
N3 C18 N2 C6 170.87(10) . . . . ?
N3 C18 N2 C7 -18.97(17) . . . . ?
O1 C6 N1 C1 173.12(10) . . . . ?
O1 C6 N1 C5 14.80(17) . . . . ?
O1 C6 N2 C7 17.82(16) . . . . ?
O1 C6 N2 C18 -171.37(10) . . . . ?

_olex2_exptl_crystal_mounting_method 'Oil on pip'
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM:Et2O'
####################################################################### 
# 
# 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_testt1
_database_code_depnum_ccdc_archive 'CCDC 1993729'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_audit_creation_date             2018-09-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 N3 O, H2 O'
_chemical_formula_sum            'C15 H21 N3 O2'
_chemical_formula_weight         275.35
_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                   7.1405(3)
_cell_length_b                   8.5770(4)
_cell_length_c                   11.9704(6)
_cell_angle_alpha                73.957(3)
_cell_angle_beta                 88.399(3)
_cell_angle_gamma                78.976(3)
_cell_volume                     691.32(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4230
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.820
_cell_measurement_theta_min      2.517
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0607 before and 0.0409 after correction. The Ratio of minimum to maximum transmission is 0.8690. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             296
_exptl_crystal_size_max          0.382
_exptl_crystal_size_mid          0.326
_exptl_crystal_size_min          0.149
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12697
_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         27.928
_diffrn_reflns_theta_min         1.771
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2810
_reflns_number_total             3308
_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       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_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         0.415
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3308
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.045
_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)+(0.0508P)²+0.2370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1040
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O2-H2A \\sim O2-H2B
 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C7(H7A,H7B)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14)
3.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.16614(12) 0.68735(11) 0.73994(8) 0.0192(2) Uani 1 1 d . . . . .
N1 N 0.35734(14) 0.42970(12) 0.79373(9) 0.0153(2) Uani 1 1 d . . . . .
N2 N 0.47949(14) 0.64342(12) 0.81087(8) 0.0144(2) Uani 1 1 d . . . . .
N3 N 0.76486(16) 0.50686(15) 0.91416(9) 0.0220(2) Uani 1 1 d . . . . .
H3 H 0.835(3) 0.415(2) 0.9382(16) 0.033(5) Uiso 1 1 d . . . . .
C1 C 0.31772(17) 0.59465(15) 0.77638(10) 0.0152(2) Uani 1 1 d . . . . .
C2 C 0.55519(16) 0.35622(14) 0.83376(10) 0.0142(2) Uani 1 1 d . . . . .
C3 C 0.61643(17) 0.50275(14) 0.86101(10) 0.0144(2) Uani 1 1 d . . . . .
C4 C 0.67973(16) 0.31452(14) 0.73434(10) 0.0141(2) Uani 1 1 d . . . . .
C5 C 0.70212(16) 0.43352(14) 0.62796(10) 0.0144(2) Uani 1 1 d . . . . .
C6 C 0.61165(17) 0.61710(15) 0.59056(10) 0.0160(2) Uani 1 1 d . . . . .
H6A H 0.475909 0.627163 0.604302 0.019 Uiso 1 1 calc R . . . .
H6B H 0.626266 0.657743 0.507342 0.019 Uiso 1 1 calc R . . . .
C7 C 0.68901(17) 0.73257(15) 0.64964(10) 0.0166(2) Uani 1 1 d . . . . .
H7A H 0.811085 0.675490 0.687477 0.020 Uiso 1 1 calc R . . . .
H7B H 0.710875 0.829581 0.590051 0.020 Uiso 1 1 calc R . . . .
C8 C 0.55536(17) 0.78885(14) 0.74011(10) 0.0161(2) Uani 1 1 d . . . . .
H8 H 0.632486 0.823293 0.792077 0.019 Uiso 1 1 calc R . . . .
C9 C 0.21769(18) 0.33488(16) 0.77712(11) 0.0197(3) Uani 1 1 d . . . . .
H9A H 0.098845 0.408317 0.749669 0.030 Uiso 1 1 calc GR . . . .
H9B H 0.199113 0.257490 0.849708 0.030 Uiso 1 1 calc GR . . . .
H9C H 0.262720 0.276122 0.721015 0.030 Uiso 1 1 calc GR . . . .
C10 C 0.56141(19) 0.21261(15) 0.94296(11) 0.0194(3) Uani 1 1 d . . . . .
H10A H 0.479645 0.248063 0.999856 0.029 Uiso 1 1 calc GR . . . .
H10B H 0.689873 0.175970 0.973884 0.029 Uiso 1 1 calc GR . . . .
H10C H 0.518644 0.123288 0.923958 0.029 Uiso 1 1 calc GR . . . .
C11 C 0.77711(17) 0.15172(15) 0.75120(11) 0.0169(2) Uani 1 1 d . . . . .
H11 H 0.765726 0.074502 0.821678 0.020 Uiso 1 1 calc R . . . .
C12 C 0.89007(17) 0.10103(16) 0.66676(11) 0.0196(3) Uani 1 1 d . . . . .
H12 H 0.951848 -0.008519 0.680349 0.024 Uiso 1 1 calc R . . . .
C13 C 0.90973(17) 0.21500(16) 0.56237(11) 0.0199(3) Uani 1 1 d . . . . .
H13 H 0.983249 0.182902 0.504291 0.024 Uiso 1 1 calc R . . . .
C14 C 0.81843(17) 0.37797(16) 0.54525(10) 0.0176(2) Uani 1 1 d . . . . .
H14 H 0.835267 0.454240 0.475314 0.021 Uiso 1 1 calc R . . . .
C15 C 0.39931(18) 0.93528(15) 0.68485(12) 0.0217(3) Uani 1 1 d . . . . .
H15A H 0.332112 0.909927 0.625769 0.033 Uiso 1 1 calc GR . . . .
H15B H 0.455238 1.030242 0.650620 0.033 Uiso 1 1 calc GR . . . .
H15C H 0.311870 0.958292 0.743218 0.033 Uiso 1 1 calc GR . . . .
O2 O 0.95041(13) 0.77029(12) 0.93200(8) 0.0226(2) Uani 1 1 d D . . . .
H2A H 1.025(2) 0.767(2) 0.8682(15) 0.043(5) Uiso 1 1 d D . . . .
H2B H 0.883(3) 0.690(3) 0.928(2) 0.080(8) Uiso 1 1 d 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
O1 C1 1.2246(15) . ?
N1 C1 1.3463(15) . ?
N1 C2 1.4674(15) . ?
N1 C9 1.4511(15) . ?
N2 C1 1.4094(15) . ?
N2 C3 1.3977(15) . ?
N2 C8 1.4885(14) . ?
N3 H3 0.828(18) . ?
N3 C3 1.2624(16) . ?
C2 C3 1.5238(16) . ?
C2 C4 1.5458(16) . ?
C2 C10 1.5232(16) . ?
C4 C5 1.4218(16) . ?
C4 C11 1.3981(16) . ?
C5 C6 1.5279(16) . ?
C5 C14 1.4002(17) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.5506(17) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.5401(17) . ?
C8 H8 0.9800 . ?
C8 C15 1.5177(17) . ?
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 0.9300 . ?
C11 C12 1.3873(17) . ?
C12 H12 0.9300 . ?
C12 C13 1.3799(18) . ?
C13 H13 0.9300 . ?
C13 C14 1.3862(18) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O2 H2A 0.922(15) . ?
O2 H2B 0.928(16) . ?

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
C1 N1 C2 112.72(9) . . ?
C1 N1 C9 123.44(10) . . ?
C9 N1 C2 123.83(10) . . ?
C1 N2 C8 122.92(9) . . ?
C3 N2 C1 109.17(9) . . ?
C3 N2 C8 115.63(9) . . ?
C3 N3 H3 113.0(12) . . ?
O1 C1 N1 126.44(11) . . ?
O1 C1 N2 125.21(11) . . ?
N1 C1 N2 108.33(10) . . ?
N1 C2 C3 100.23(9) . . ?
N1 C2 C4 111.53(9) . . ?
N1 C2 C10 110.66(9) . . ?
C3 C2 C4 107.72(9) . . ?
C10 C2 C3 111.09(9) . . ?
C10 C2 C4 114.63(10) . . ?
N2 C3 C2 107.57(10) . . ?
N3 C3 N2 123.22(11) . . ?
N3 C3 C2 129.15(11) . . ?
C5 C4 C2 123.35(10) . . ?
C11 C4 C2 117.97(10) . . ?
C11 C4 C5 118.67(11) . . ?
C4 C5 C6 127.97(10) . . ?
C14 C5 C4 117.18(11) . . ?
C14 C5 C6 114.84(10) . . ?
C5 C6 H6A 107.9 . . ?
C5 C6 H6B 107.9 . . ?
C5 C6 C7 117.54(10) . . ?
H6A C6 H6B 107.2 . . ?
C7 C6 H6A 107.9 . . ?
C7 C6 H6B 107.9 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C6 114.11(9) . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
N2 C8 C7 108.05(9) . . ?
N2 C8 H8 107.7 . . ?
N2 C8 C15 112.98(10) . . ?
C7 C8 H8 107.7 . . ?
C15 C8 C7 112.46(10) . . ?
C15 C8 H8 107.7 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4 C11 H11 118.8 . . ?
C12 C11 C4 122.48(11) . . ?
C12 C11 H11 118.8 . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.25(12) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 120.4 . . ?
C12 C13 C14 119.11(11) . . ?
C14 C13 H13 120.4 . . ?
C5 C14 H14 118.4 . . ?
C13 C14 C5 123.29(11) . . ?
C13 C14 H14 118.4 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
H2A O2 H2B 97.3(19) . . ?

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
N3 H3 O2 0.828(18) 2.265(19) 3.0194(15) 151.6(16) 2_767 yes
O2 H2A O1 0.922(15) 2.017(16) 2.9071(13) 161.8(17) 1_655 yes
O2 H2B N3 0.928(16) 1.962(16) 2.8868(15) 174(2) . yes

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM:Et2O'
####################################################################### 
# 
# 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_testt1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1993731'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_audit_creation_date             2019-10-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H21 N3 O'
_chemical_formula_sum            'C17 H21 N3 O'
_chemical_formula_weight         283.37
_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                   7.0488(2)
_cell_length_b                   8.6329(3)
_cell_length_c                   12.6463(5)
_cell_angle_alpha                88.989(2)
_cell_angle_beta                 74.751(2)
_cell_angle_gamma                77.777(2)
_cell_volume                     725.03(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5830
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.09
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6845
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0487 before and 0.0362 after correction. The Ratio of minimum to maximum transmission is 0.9181. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.329
_exptl_crystal_size_min          0.322
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 1.000
_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       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13480
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.115
_diffrn_reflns_theta_min         1.670
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3130
_reflns_number_total             3531
_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       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_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         0.331
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3531
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.034
_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)+(0.0422P)²+0.3184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0940
_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:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C14(H14A,H14B), C15(H15A,
 H15B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.12507(11) 0.12693(9) 0.71185(7) 0.01657(17) Uani 1 1 d . . . . .
N1 N 0.41384(13) 0.22290(10) 0.64479(7) 0.01133(18) Uani 1 1 d . . . . .
N2 N 0.38359(13) 0.08916(10) 0.79757(7) 0.01189(18) Uani 1 1 d . . . . .
N3 N 0.69614(14) 0.07318(11) 0.83444(8) 0.01488(19) Uani 1 1 d . . . . .
C1 C 0.29027(15) 0.14514(12) 0.71581(8) 0.0120(2) Uani 1 1 d . . . . .
C2 C 0.59986(14) 0.22295(12) 0.67559(8) 0.0104(2) Uani 1 1 d . . . . .
C3 C 0.57521(15) 0.12120(12) 0.77671(8) 0.0112(2) Uani 1 1 d . . . . .
C4 C 0.38437(16) 0.28672(13) 0.54192(9) 0.0147(2) Uani 1 1 d . . . . .
H4A H 0.372270 0.403050 0.544287 0.018 Uiso 1 1 calc R . . . .
H4B H 0.258093 0.265429 0.530986 0.018 Uiso 1 1 calc R . . . .
C5 C 0.56136(16) 0.21095(14) 0.44673(9) 0.0163(2) Uani 1 1 d . . . . .
H5A H 0.552577 0.269020 0.379375 0.020 Uiso 1 1 calc R . . . .
H5B H 0.554144 0.099874 0.433671 0.020 Uiso 1 1 calc R . . . .
C6 C 0.76227(16) 0.21353(13) 0.47038(9) 0.0149(2) Uani 1 1 d . . . . .
H6A H 0.778524 0.324507 0.472144 0.018 Uiso 1 1 calc R . . . .
H6B H 0.873512 0.154175 0.410637 0.018 Uiso 1 1 calc R . . . .
C7 C 0.77493(15) 0.13952(12) 0.58015(8) 0.0123(2) Uani 1 1 d . . . . .
H7A H 0.904266 0.147279 0.594335 0.015 Uiso 1 1 calc R . . . .
H7B H 0.771875 0.025718 0.575863 0.015 Uiso 1 1 calc R . . . .
C8 C 0.61186(15) 0.38974(12) 0.71246(8) 0.0116(2) Uani 1 1 d . . . . .
C9 C 0.79066(16) 0.44193(13) 0.67156(9) 0.0154(2) Uani 1 1 d . . . . .
H9 H 0.897178 0.377409 0.617924 0.018 Uiso 1 1 calc R . . . .
C10 C 0.81784(17) 0.58534(13) 0.70683(10) 0.0180(2) Uani 1 1 d . . . . .
H10 H 0.941464 0.617469 0.677512 0.022 Uiso 1 1 calc R . . . .
C11 C 0.66433(18) 0.68114(13) 0.78474(9) 0.0178(2) Uani 1 1 d . . . . .
H11 H 0.680970 0.779471 0.809416 0.021 Uiso 1 1 calc R . . . .
C12 C 0.48606(17) 0.63102(13) 0.82605(9) 0.0164(2) Uani 1 1 d . . . . .
H12 H 0.380759 0.697163 0.879367 0.020 Uiso 1 1 calc R . . . .
C13 C 0.45428(16) 0.48711(12) 0.79266(8) 0.0128(2) Uani 1 1 d . . . . .
C14 C 0.25326(16) 0.44768(12) 0.85048(9) 0.0142(2) Uani 1 1 d . . . . .
H14A H 0.211356 0.386390 0.798494 0.017 Uiso 1 1 calc R . . . .
H14B H 0.151043 0.547850 0.871038 0.017 Uiso 1 1 calc R . . . .
C15 C 0.25629(16) 0.35088(13) 0.95532(9) 0.0161(2) Uani 1 1 d . . . . .
H15A H 0.398017 0.304607 0.953953 0.019 Uiso 1 1 calc R . . . .
H15B H 0.198133 0.424408 1.020460 0.019 Uiso 1 1 calc R . . . .
C16 C 0.14021(16) 0.21636(13) 0.96814(9) 0.0170(2) Uani 1 1 d . . . . .
H16A H 0.093374 0.196429 1.047094 0.020 Uiso 1 1 calc R . . . .
H16B H 0.019715 0.251199 0.940378 0.020 Uiso 1 1 calc R . . . .
C17 C 0.26576(16) 0.06065(13) 0.90710(9) 0.0150(2) Uani 1 1 d . . . . .
H17A H 0.357737 0.006185 0.949852 0.018 Uiso 1 1 calc R . . . .
H17B H 0.174974 -0.009825 0.900682 0.018 Uiso 1 1 calc R . . . .
H3 H 0.813(3) 0.1051(19) 0.8065(14) 0.032(4) 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
O1 C1 1.2214(13) . ?
N1 C1 1.3531(13) . ?
N1 C2 1.4628(12) . ?
N1 C4 1.4517(13) . ?
N2 C1 1.3931(13) . ?
N2 C3 1.3923(13) . ?
N2 C17 1.4623(13) . ?
N3 C3 1.2644(14) . ?
N3 H3 0.907(17) . ?
C2 C3 1.5314(14) . ?
C2 C7 1.5392(14) . ?
C2 C8 1.5472(14) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5251(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5270(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5340(14) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.3958(14) . ?
C8 C13 1.4182(14) . ?
C9 H9 0.9500 . ?
C9 C10 1.3904(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.3837(17) . ?
C11 H11 0.9500 . ?
C11 C12 1.3842(16) . ?
C12 H12 0.9500 . ?
C12 C13 1.3992(15) . ?
C13 C14 1.5194(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5572(15) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5396(15) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5362(15) . ?
C17 H17A 0.9900 . ?
C17 H17B 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
C1 N1 C2 112.67(8) . . ?
C1 N1 C4 126.06(9) . . ?
C4 N1 C2 120.95(8) . . ?
C1 N2 C17 121.12(8) . . ?
C3 N2 C1 111.51(8) . . ?
C3 N2 C17 123.26(9) . . ?
C3 N3 H3 110.1(10) . . ?
O1 C1 N1 127.40(10) . . ?
O1 C1 N2 124.85(10) . . ?
N1 C1 N2 107.74(9) . . ?
N1 C2 C3 101.41(8) . . ?
N1 C2 C7 106.86(8) . . ?
N1 C2 C8 112.67(8) . . ?
C3 C2 C7 111.28(8) . . ?
C3 C2 C8 107.68(8) . . ?
C7 C2 C8 116.01(8) . . ?
N2 C3 C2 106.34(8) . . ?
N3 C3 N2 123.87(9) . . ?
N3 C3 C2 129.78(9) . . ?
N1 C4 H4A 109.6 . . ?
N1 C4 H4B 109.6 . . ?
N1 C4 C5 110.16(8) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.6 . . ?
C5 C4 H4B 109.6 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C4 C5 C6 111.35(9) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C5 C6 C7 111.48(8) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C2 C7 H7A 109.3 . . ?
C2 C7 H7B 109.3 . . ?
C6 C7 C2 111.56(8) . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C2 118.79(9) . . ?
C9 C8 C13 118.34(9) . . ?
C13 C8 C2 122.68(9) . . ?
C8 C9 H9 118.9 . . ?
C10 C9 C8 122.10(10) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.82(10) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.6 . . ?
C10 C11 C12 118.76(10) . . ?
C12 C11 H11 120.6 . . ?
C11 C12 H12 118.6 . . ?
C11 C12 C13 122.83(10) . . ?
C13 C12 H12 118.6 . . ?
C8 C13 C14 126.12(9) . . ?
C12 C13 C8 118.16(10) . . ?
C12 C13 C14 115.68(9) . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C13 C14 C15 114.05(9) . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C14 C15 H15A 108.6 . . ?
C14 C15 H15B 108.6 . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 C14 114.48(9) . . ?
C16 C15 H15A 108.6 . . ?
C16 C15 H15B 108.6 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.50(9) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
N2 C17 C16 111.45(9) . . ?
N2 C17 H17A 109.3 . . ?
N2 C17 H17B 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM:Et2O'
####################################################################### 
# 
# 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_testt1_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1993730'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_audit_creation_date             2020-02-18
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N3 O'
_chemical_formula_sum            'C16 H19 N3 O'
_chemical_formula_weight         269.34
_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 0.0033 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                   6.9675(12)
_cell_length_b                   8.6877(14)
_cell_length_c                   12.0676(19)
_cell_angle_alpha                87.020(11)
_cell_angle_beta                 74.121(11)
_cell_angle_gamma                77.399(12)
_cell_volume                     685.7(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1931
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.23
_cell_measurement_theta_min      2.96
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0990 before and 0.0593 after correction.
The Ratio of minimum to maximum transmission is 0.8032.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.352
_exptl_crystal_size_min          0.185
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12669
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.187
_diffrn_reflns_theta_min         2.402
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_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                2293
_reflns_number_total             3290
_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       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.034
_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)+(0.0463P)²+0.0656P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1020
_refine_ls_wR_factor_ref         0.1140
_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:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.15533(17) 0.11992(13) 0.68181(10) 0.0316(3) Uani 1 1 d . . . . .
N1 N 0.43144(19) 0.23999(14) 0.62269(11) 0.0217(3) Uani 1 1 d . . . . .
N2 N 0.39649(19) 0.09957(15) 0.78475(11) 0.0229(3) Uani 1 1 d . . . . .
N3 N 0.7100(2) 0.07936(16) 0.82717(13) 0.0296(3) Uani 1 1 d . . . . .
C1 C 0.3117(2) 0.15051(17) 0.69371(14) 0.0231(3) Uani 1 1 d . . . . .
C2 C 0.6189(2) 0.23632(17) 0.65905(13) 0.0207(3) Uani 1 1 d . . . . .
C3 C 0.5911(2) 0.13084(17) 0.76450(13) 0.0216(3) Uani 1 1 d . . . . .
C4 C 0.4692(3) 0.2403(2) 0.49647(14) 0.0296(4) Uani 1 1 d . . . . .
H4A H 0.386310 0.335663 0.470635 0.035 Uiso 1 1 calc R U . . .
H4B H 0.437845 0.145465 0.469296 0.035 Uiso 1 1 calc R U . . .
C5 C 0.6973(3) 0.2398(2) 0.45293(14) 0.0319(4) Uani 1 1 d . . . . .
H5A H 0.760574 0.176997 0.381006 0.038 Uiso 1 1 calc R U . . .
H5B H 0.720265 0.348423 0.438635 0.038 Uiso 1 1 calc R U . . .
C6 C 0.7835(2) 0.16382(19) 0.55121(14) 0.0265(4) Uani 1 1 d . . . . .
H6A H 0.916189 0.190785 0.547096 0.032 Uiso 1 1 calc R U . . .
H6B H 0.801395 0.047649 0.549848 0.032 Uiso 1 1 calc R U . . .
C7 C 0.6309(2) 0.39953(17) 0.69842(13) 0.0209(3) Uani 1 1 d . . . . .
C8 C 0.8142(2) 0.45045(18) 0.65898(14) 0.0264(4) Uani 1 1 d . . . . .
H8 H 0.926376 0.385801 0.606454 0.032 Uiso 1 1 calc R U . . .
C9 C 0.8368(3) 0.59366(19) 0.69471(15) 0.0319(4) Uani 1 1 d . . . . .
H9 H 0.963505 0.625373 0.666970 0.038 Uiso 1 1 calc R U . . .
C10 C 0.6759(3) 0.68918(19) 0.77006(15) 0.0331(4) Uani 1 1 d . . . . .
H10 H 0.689561 0.787772 0.794001 0.040 Uiso 1 1 calc R U . . .
C11 C 0.4939(3) 0.63966(19) 0.81050(15) 0.0311(4) Uani 1 1 d . . . . .
H11 H 0.383118 0.706403 0.862438 0.037 Uiso 1 1 calc R U . . .
C12 C 0.4656(2) 0.49581(18) 0.77840(13) 0.0235(3) Uani 1 1 d . . . . .
C13 C 0.2618(2) 0.45395(18) 0.83738(14) 0.0267(4) Uani 1 1 d . . . . .
H13A H 0.222858 0.394545 0.782166 0.032 Uiso 1 1 calc R U . . .
H13B H 0.157054 0.552751 0.857490 0.032 Uiso 1 1 calc R U . . .
C14 C 0.2598(3) 0.3543(2) 0.94839(14) 0.0307(4) Uani 1 1 d . . . . .
H14A H 0.402588 0.307679 0.948720 0.037 Uiso 1 1 calc R U . . .
H14B H 0.198381 0.425502 1.016160 0.037 Uiso 1 1 calc R U . . .
C15 C 0.1421(3) 0.2209(2) 0.96143(15) 0.0336(4) Uani 1 1 d . . . . .
H15A H 0.091705 0.198483 1.044365 0.040 Uiso 1 1 calc R U . . .
H15B H 0.021803 0.256971 0.930843 0.040 Uiso 1 1 calc R U . . .
C16 C 0.2713(3) 0.06766(19) 0.89881(14) 0.0298(4) Uani 1 1 d . . . . .
H16A H 0.361024 0.011001 0.945484 0.036 Uiso 1 1 calc R U . . .
H16B H 0.179935 -0.001245 0.890599 0.036 Uiso 1 1 calc R U . . .
H3 H 0.835(3) 0.112(2) 0.7968(17) 0.048(6) 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
O1 C1 1.2224(18) . ?
N1 C1 1.363(2) . ?
N1 C2 1.4813(19) . ?
N1 C4 1.473(2) . ?
N2 C1 1.3937(19) . ?
N2 C3 1.3945(19) . ?
N2 C16 1.463(2) . ?
N3 C3 1.2665(19) . ?
N3 H3 0.95(2) . ?
C2 C3 1.522(2) . ?
C2 C6 1.536(2) . ?
C2 C7 1.545(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.530(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.529(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.395(2) . ?
C7 C12 1.419(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.392(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.374(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.397(2) . ?
C12 C13 1.516(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.555(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.538(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.537(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 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
C1 N1 C2 110.83(12) . . ?
C1 N1 C4 123.26(13) . . ?
C4 N1 C2 112.53(12) . . ?
C1 N2 C3 111.29(13) . . ?
C1 N2 C16 122.00(13) . . ?
C3 N2 C16 123.84(13) . . ?
C3 N3 H3 109.5(12) . . ?
O1 C1 N1 126.76(15) . . ?
O1 C1 N2 124.93(15) . . ?
N1 C1 N2 108.31(13) . . ?
N1 C2 C3 102.37(12) . . ?
N1 C2 C6 100.63(12) . . ?
N1 C2 C7 112.80(11) . . ?
C3 C2 C6 115.73(12) . . ?
C3 C2 C7 107.64(12) . . ?
C6 C2 C7 116.67(13) . . ?
N2 C3 C2 106.15(12) . . ?
N3 C3 N2 123.52(14) . . ?
N3 C3 C2 130.31(14) . . ?
N1 C4 H4A 111.1 . . ?
N1 C4 H4B 111.1 . . ?
N1 C4 C5 103.32(12) . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 H4A 111.1 . . ?
C5 C4 H4B 111.1 . . ?
C4 C5 H5A 111.0 . . ?
C4 C5 H5B 111.0 . . ?
H5A C5 H5B 109.0 . . ?
C6 C5 C4 103.65(13) . . ?
C6 C5 H5A 111.0 . . ?
C6 C5 H5B 111.0 . . ?
C2 C6 H6A 111.2 . . ?
C2 C6 H6B 111.2 . . ?
C5 C6 C2 102.86(13) . . ?
C5 C6 H6A 111.2 . . ?
C5 C6 H6B 111.2 . . ?
H6A C6 H6B 109.1 . . ?
C8 C7 C2 118.90(14) . . ?
C8 C7 C12 118.68(14) . . ?
C12 C7 C2 122.32(14) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.60(16) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.03(16) . . ?
C10 C9 H9 120.0 . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 118.97(15) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 118.5 . . ?
C10 C11 C12 122.90(16) . . ?
C12 C11 H11 118.5 . . ?
C7 C12 C13 125.97(14) . . ?
C11 C12 C7 117.78(15) . . ?
C11 C12 C13 116.19(14) . . ?
C12 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
C12 C13 C14 114.49(13) . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C13 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 C13 114.59(13) . . ?
C15 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 C14 113.43(14) . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
N2 C16 C15 111.45(13) . . ?
N2 C16 H16A 109.3 . . ?
N2 C16 H16B 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 N2 -5.65(14) . . . . ?
N1 C2 C3 N3 175.67(15) . . . . ?
N1 C2 C6 C5 38.19(14) . . . . ?
N1 C2 C7 C8 -134.56(14) . . . . ?
N1 C2 C7 C12 49.08(18) . . . . ?
N1 C4 C5 C6 25.49(16) . . . . ?
C1 N1 C2 C3 -0.49(15) . . . . ?
C1 N1 C2 C6 119.08(13) . . . . ?
C1 N1 C2 C7 -115.88(14) . . . . ?
C1 N1 C4 C5 -138.15(14) . . . . ?
C1 N2 C3 N3 -171.15(14) . . . . ?
C1 N2 C3 C2 10.06(16) . . . . ?
C1 N2 C16 C15 -71.49(18) . . . . ?
C2 N1 C1 O1 -174.09(14) . . . . ?
C2 N1 C1 N2 6.52(16) . . . . ?
C2 N1 C4 C5 -1.06(16) . . . . ?
C2 C7 C8 C9 -177.59(14) . . . . ?
C2 C7 C12 C11 178.42(13) . . . . ?
C2 C7 C12 C13 1.5(2) . . . . ?
C3 N2 C1 O1 169.99(14) . . . . ?
C3 N2 C1 N1 -10.61(16) . . . . ?
C3 N2 C16 C15 87.65(18) . . . . ?
C3 C2 C6 C5 147.60(13) . . . . ?
C3 C2 C7 C8 113.26(15) . . . . ?
C3 C2 C7 C12 -63.10(17) . . . . ?
C4 N1 C1 O1 -36.4(2) . . . . ?
C4 N1 C1 N2 144.23(14) . . . . ?
C4 N1 C2 C3 -142.97(12) . . . . ?
C4 N1 C2 C6 -23.40(15) . . . . ?
C4 N1 C2 C7 101.65(14) . . . . ?
C4 C5 C6 C2 -40.24(15) . . . . ?
C6 C2 C3 N2 -114.03(14) . . . . ?
C6 C2 C3 N3 67.3(2) . . . . ?
C6 C2 C7 C8 -18.77(19) . . . . ?
C6 C2 C7 C12 164.87(14) . . . . ?
C7 C2 C3 N2 113.43(13) . . . . ?
C7 C2 C3 N3 -65.3(2) . . . . ?
C7 C2 C6 C5 -84.18(15) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C7 C12 C13 C14 84.78(19) . . . . ?
C8 C7 C12 C11 2.0(2) . . . . ?
C8 C7 C12 C13 -174.92(14) . . . . ?
C8 C9 C10 C11 0.9(2) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 C7 -1.6(2) . . . . ?
C10 C11 C12 C13 175.63(15) . . . . ?
C11 C12 C13 C14 -92.23(17) . . . . ?
C12 C7 C8 C9 -1.1(2) . . . . ?
C12 C13 C14 C15 -138.81(14) . . . . ?
C13 C14 C15 C16 85.39(18) . . . . ?
C14 C15 C16 N2 -42.42(19) . . . . ?
C16 N2 C1 O1 -28.5(2) . . . . ?
C16 N2 C1 N1 150.88(13) . . . . ?
C16 N2 C3 N3 27.8(2) . . . . ?
C16 N2 C3 C2 -151.03(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CDCl3:n-pentane'
####################################################################### 
# 
# 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_testh1
_database_code_depnum_ccdc_archive 'CCDC 1993727'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_audit_creation_date             2018-08-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 N3 O'
_chemical_formula_sum            'C15 H19 N3 O'
_chemical_formula_weight         257.33
_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      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           'P 31'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   22.0392(6)
_cell_length_b                   22.0392(6)
_cell_length_c                   7.1184(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2994.36(18)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    3052
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      21.898
_cell_measurement_theta_min      2.824
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.968
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0897 before and 0.0596 after correction. The Ratio of minimum to maximum transmission is 0.8678. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1242
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.323
_exptl_crystal_size_min          0.234
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            22901
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         1.848
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.982
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                6127
_reflns_number_total             7518
_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       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_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         0.162
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     532
_refine_ls_number_reflns         7518
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      1.023
_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)+(0.0361P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0905
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C16(H16A,H16B), C17(H17A,
 H17B), C18(H18A,H18B), C19(H19A,H19B), C31(H31A,H31B), C32(H32A,H32B),
 C33(H33A,H33B), C34(H34A,H34B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C25(H25), C26(H26), C27(H27),
 C28(H28), C40(H40), C41(H41), C42(H42), C43(H43)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C29(H29A,H29B,H29C), C30(H30A,H30B,
 H30C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.24540(14) 0.07713(13) 0.5564(3) 0.0221(6) Uani 1 1 d . . . . .
N1 N 0.20341(16) 0.02602(16) 0.2653(4) 0.0167(7) Uani 1 1 d . . . . .
N2 N 0.29261(16) 0.13514(16) 0.2788(4) 0.0153(7) Uani 1 1 d . . . . .
N3 N 0.18668(18) 0.00504(17) -0.0578(4) 0.0224(8) Uani 1 1 d . . . . .
C1 C 0.1347(2) -0.0295(2) 0.3280(5) 0.0242(10) Uani 1 1 d . . . . .
H1A H 0.140043 -0.050055 0.445978 0.029 Uiso 1 1 calc R . . . .
H1B H 0.114619 -0.066960 0.231971 0.029 Uiso 1 1 calc R . . . .
C2 C 0.0843(2) -0.0016(2) 0.3610(6) 0.0302(10) Uani 1 1 d . . . . .
H2A H 0.094336 0.021344 0.485597 0.036 Uiso 1 1 calc R . . . .
H2B H 0.035795 -0.041693 0.363727 0.036 Uiso 1 1 calc R . . . .
C3 C 0.0891(2) 0.0515(2) 0.2098(6) 0.0279(10) Uani 1 1 d . . . . .
H3A H 0.098907 0.037411 0.086464 0.034 Uiso 1 1 calc R . . . .
H3B H 0.043177 0.049111 0.200911 0.034 Uiso 1 1 calc R . . . .
C4 C 0.1465(2) 0.1283(2) 0.2509(5) 0.0230(9) Uani 1 1 d . . . . .
H4A H 0.123643 0.152664 0.308607 0.028 Uiso 1 1 calc R . . . .
H4B H 0.179167 0.127619 0.345110 0.028 Uiso 1 1 calc R . . . .
C5 C 0.1893(2) 0.1714(2) 0.0824(5) 0.0185(8) Uani 1 1 d . . . . .
C6 C 0.24776(19) 0.16996(19) 0.0029(5) 0.0152(8) Uani 1 1 d . . . . .
C7 C 0.27559(19) 0.12309(19) 0.0766(5) 0.0144(8) Uani 1 1 d . . . . .
C8 C 0.2180(2) 0.0461(2) 0.0776(5) 0.0177(8) Uani 1 1 d . . . . .
C9 C 0.24805(19) 0.0805(2) 0.3846(5) 0.0157(8) Uani 1 1 d . . . . .
C10 C 0.1691(2) 0.2165(2) 0.0042(5) 0.0233(9) Uani 1 1 d . . . . .
H10 H 0.130139 0.217925 0.056427 0.028 Uiso 1 1 calc R . . . .
C11 C 0.2040(2) 0.2596(2) -0.1477(5) 0.0243(9) Uani 1 1 d . . . . .
H11 H 0.188421 0.289131 -0.199694 0.029 Uiso 1 1 calc R . . . .
C12 C 0.2613(2) 0.2591(2) -0.2220(5) 0.0243(9) Uani 1 1 d . . . . .
H12 H 0.286308 0.289154 -0.323802 0.029 Uiso 1 1 calc R . . . .
C13 C 0.2823(2) 0.2145(2) -0.1474(5) 0.0191(8) Uani 1 1 d . . . . .
H13 H 0.321701 0.214255 -0.200641 0.023 Uiso 1 1 calc R . . . .
C14 C 0.3390(2) 0.1296(2) -0.0306(5) 0.0189(9) Uani 1 1 d . . . . .
H14A H 0.377574 0.178115 -0.024848 0.028 Uiso 1 1 calc GR . . . .
H14B H 0.326031 0.116056 -0.162038 0.028 Uiso 1 1 calc GR . . . .
H14C H 0.353796 0.098607 0.026616 0.028 Uiso 1 1 calc GR . . . .
C15 C 0.3355(2) 0.2052(2) 0.3557(5) 0.0192(9) Uani 1 1 d . . . . .
H15A H 0.377184 0.231555 0.277076 0.029 Uiso 1 1 calc GR . . . .
H15B H 0.349908 0.201852 0.483764 0.029 Uiso 1 1 calc GR . . . .
H15C H 0.308367 0.229348 0.358048 0.029 Uiso 1 1 calc GR . . . .
O2 O 0.46454(14) 0.36564(13) 0.4810(3) 0.0217(6) Uani 1 1 d . . . . .
N4 N 0.47625(16) 0.32386(15) 0.7695(4) 0.0157(7) Uani 1 1 d . . . . .
N5 N 0.47001(16) 0.42173(16) 0.7594(4) 0.0152(7) Uani 1 1 d . . . . .
N6 N 0.48676(17) 0.30973(17) 1.0926(4) 0.0200(7) Uani 1 1 d . . . . .
C16 C 0.5064(2) 0.2826(2) 0.6988(5) 0.0202(9) Uani 1 1 d . . . . .
H16A H 0.479148 0.255032 0.588659 0.024 Uiso 1 1 calc R . . . .
H16B H 0.503099 0.249323 0.797139 0.024 Uiso 1 1 calc R . . . .
C17 C 0.5832(2) 0.3289(2) 0.6418(5) 0.0214(9) Uani 1 1 d . . . . .
H17A H 0.585069 0.350852 0.518956 0.026 Uiso 1 1 calc R . . . .
H17B H 0.604484 0.298911 0.625079 0.026 Uiso 1 1 calc R . . . .
C18 C 0.6273(2) 0.3869(2) 0.7839(5) 0.0201(9) Uani 1 1 d . . . . .
H18A H 0.676658 0.398016 0.774378 0.024 Uiso 1 1 calc R . . . .
H18B H 0.610708 0.368878 0.912155 0.024 Uiso 1 1 calc R . . . .
C19 C 0.6247(2) 0.45581(19) 0.7562(5) 0.0170(8) Uani 1 1 d . . . . .
H19A H 0.668081 0.490535 0.691403 0.020 Uiso 1 1 calc R . . . .
H19B H 0.584710 0.445791 0.673317 0.020 Uiso 1 1 calc R . . . .
C20 C 0.61750(19) 0.48811(19) 0.9378(5) 0.0142(8) Uani 1 1 d . . . . .
C21 C 0.55424(18) 0.47132(18) 1.0298(5) 0.0136(8) Uani 1 1 d . . . . .
C22 C 0.48207(18) 0.41414(19) 0.9591(5) 0.0146(8) Uani 1 1 d . . . . .
C23 C 0.48166(18) 0.34426(19) 0.9566(5) 0.0151(8) Uani 1 1 d . . . . .
C24 C 0.46957(19) 0.37087(19) 0.6528(5) 0.0160(8) Uani 1 1 d . . . . .
C25 C 0.6804(2) 0.53864(19) 1.0191(5) 0.0178(8) Uani 1 1 d . . . . .
H25 H 0.723218 0.550722 0.957497 0.021 Uiso 1 1 calc R . . . .
C26 C 0.6825(2) 0.57176(19) 1.1867(5) 0.0187(9) Uani 1 1 d . . . . .
H26 H 0.726096 0.606043 1.238245 0.022 Uiso 1 1 calc R . . . .
C27 C 0.6208(2) 0.55445(19) 1.2775(5) 0.0182(9) Uani 1 1 d . . . . .
H27 H 0.621445 0.576213 1.393285 0.022 Uiso 1 1 calc R . . . .
C28 C 0.5580(2) 0.50519(19) 1.1990(5) 0.0167(8) Uani 1 1 d . . . . .
H28 H 0.515652 0.493903 1.262272 0.020 Uiso 1 1 calc R . . . .
C29 C 0.41971(19) 0.4067(2) 1.0733(5) 0.0190(8) Uani 1 1 d . . . . .
H29A H 0.419891 0.451289 1.071826 0.028 Uiso 1 1 calc GR . . . .
H29B H 0.423410 0.394188 1.203141 0.028 Uiso 1 1 calc GR . . . .
H29C H 0.375968 0.369989 1.017780 0.028 Uiso 1 1 calc GR . . . .
C30 C 0.4793(2) 0.48619(19) 0.6803(5) 0.0196(9) Uani 1 1 d . . . . .
H30A H 0.461278 0.507633 0.768040 0.029 Uiso 1 1 calc GR . . . .
H30B H 0.453787 0.476196 0.561187 0.029 Uiso 1 1 calc GR . . . .
H30C H 0.529299 0.518469 0.657901 0.029 Uiso 1 1 calc GR . . . .
O3 O 0.54098(14) 0.64260(14) 0.4905(3) 0.0212(6) Uani 1 1 d . . . . .
N7 N 0.48681(15) 0.61875(16) 0.1996(4) 0.0156(7) Uani 1 1 d . . . . .
N8 N 0.60072(16) 0.69453(15) 0.2171(4) 0.0152(7) Uani 1 1 d . . . . .
N9 N 0.46384(17) 0.61416(17) -0.1223(5) 0.0183(7) Uani 1 1 d . . . . .
C31 C 0.41516(19) 0.5920(2) 0.2681(5) 0.0195(9) Uani 1 1 d . . . . .
H31A H 0.406570 0.560393 0.376142 0.023 Uiso 1 1 calc R . . . .
H31B H 0.381598 0.564358 0.167513 0.023 Uiso 1 1 calc R . . . .
C32 C 0.4026(2) 0.6511(2) 0.3284(5) 0.0222(9) Uani 1 1 d . . . . .
H32A H 0.424980 0.669070 0.452078 0.027 Uiso 1 1 calc R . . . .
H32B H 0.351577 0.632194 0.343735 0.027 Uiso 1 1 calc R . . . .
C33 C 0.4313(2) 0.7124(2) 0.1875(5) 0.0205(9) Uani 1 1 d . . . . .
H33A H 0.403010 0.735696 0.196635 0.025 Uiso 1 1 calc R . . . .
H33B H 0.425731 0.693309 0.058714 0.025 Uiso 1 1 calc R . . . .
C34 C 0.5101(2) 0.7682(2) 0.2193(5) 0.0195(9) Uani 1 1 d . . . . .
H34A H 0.512368 0.808667 0.286110 0.023 Uiso 1 1 calc R . . . .
H34B H 0.531073 0.747625 0.302493 0.023 Uiso 1 1 calc R . . . .
C35 C 0.55474(19) 0.79509(19) 0.0413(5) 0.0185(8) Uani 1 1 d . . . . .
C36 C 0.59120(19) 0.76531(19) -0.0465(5) 0.0167(8) Uani 1 1 d . . . . .
C37 C 0.58395(19) 0.69500(19) 0.0166(5) 0.0151(8) Uani 1 1 d . . . . .
C38 C 0.5062(2) 0.63928(19) 0.0148(5) 0.0160(8) Uani 1 1 d . . . . .
C39 C 0.54403(19) 0.65197(19) 0.3202(5) 0.0160(8) Uani 1 1 d . . . . .
C40 C 0.5606(2) 0.8558(2) -0.0377(6) 0.0250(9) Uani 1 1 d . . . . .
H40 H 0.536426 0.876376 0.020146 0.030 Uiso 1 1 calc R . . . .
C41 C 0.6000(2) 0.8871(2) -0.1957(6) 0.0270(10) Uani 1 1 d . . . . .
H41 H 0.601652 0.927769 -0.246849 0.032 Uiso 1 1 calc R . . . .
C42 C 0.6367(2) 0.8592(2) -0.2784(6) 0.0282(10) Uani 1 1 d . . . . .
H42 H 0.664815 0.880910 -0.386027 0.034 Uiso 1 1 calc R . . . .
C43 C 0.6325(2) 0.7989(2) -0.2036(5) 0.0223(9) Uani 1 1 d . . . . .
H43 H 0.658392 0.779989 -0.260887 0.027 Uiso 1 1 calc R . . . .
C44 C 0.62552(19) 0.6702(2) -0.1026(5) 0.0179(8) Uani 1 1 d . . . . .
H44A H 0.675637 0.704497 -0.093907 0.027 Uiso 1 1 calc GR . . . .
H44B H 0.610444 0.665484 -0.233878 0.027 Uiso 1 1 calc GR . . . .
H44C H 0.617004 0.624742 -0.055955 0.027 Uiso 1 1 calc GR . . . .
C45 C 0.6692(2) 0.7389(2) 0.2986(5) 0.0223(9) Uani 1 1 d . . . . .
H45A H 0.704258 0.733017 0.229041 0.033 Uiso 1 1 calc GR . . . .
H45B H 0.668861 0.725739 0.430272 0.033 Uiso 1 1 calc GR . . . .
H45C H 0.680710 0.787925 0.291746 0.033 Uiso 1 1 calc GR . . . .
H9 H 0.484(2) 0.631(2) -0.226(5) 0.017(11) Uiso 1 1 d . . . . .
H6 H 0.491(2) 0.333(2) 1.202(5) 0.028(12) Uiso 1 1 d . . . . .
H3 H 0.203(2) 0.024(2) -0.170(6) 0.023(11) 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
O1 C9 1.224(4) . ?
N1 C1 1.462(5) . ?
N1 C8 1.393(4) . ?
N1 C9 1.396(5) . ?
N2 C7 1.477(4) . ?
N2 C9 1.342(5) . ?
N2 C15 1.455(5) . ?
N3 C8 1.265(5) . ?
N3 H3 0.89(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.530(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.553(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.553(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.528(5) . ?
C5 C6 1.422(5) . ?
C5 C10 1.394(5) . ?
C6 C7 1.534(5) . ?
C6 C13 1.393(5) . ?
C7 C8 1.529(5) . ?
C7 C14 1.535(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.390(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.373(6) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(5) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
O2 C24 1.228(4) . ?
N4 C16 1.459(5) . ?
N4 C23 1.392(4) . ?
N4 C24 1.392(5) . ?
N5 C22 1.471(4) . ?
N5 C24 1.350(4) . ?
N5 C30 1.444(4) . ?
N6 C23 1.270(5) . ?
N6 H6 0.91(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.531(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.536(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.561(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.522(5) . ?
C20 C21 1.412(5) . ?
C20 C25 1.398(5) . ?
C21 C22 1.539(5) . ?
C21 C28 1.397(5) . ?
C22 C23 1.536(5) . ?
C22 C29 1.534(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.387(5) . ?
C26 H26 0.9500 . ?
C26 C27 1.376(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.381(5) . ?
C28 H28 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
O3 C39 1.226(4) . ?
N7 C31 1.466(5) . ?
N7 C38 1.387(4) . ?
N7 C39 1.393(5) . ?
N8 C37 1.476(4) . ?
N8 C39 1.345(4) . ?
N8 C45 1.447(5) . ?
N9 C38 1.271(5) . ?
N9 H9 0.85(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.524(5) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.541(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.562(5) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.530(5) . ?
C35 C36 1.412(5) . ?
C35 C40 1.396(5) . ?
C36 C37 1.543(5) . ?
C36 C43 1.398(5) . ?
C37 C38 1.529(5) . ?
C37 C44 1.536(5) . ?
C40 H40 0.9500 . ?
C40 C41 1.376(6) . ?
C41 H41 0.9500 . ?
C41 C42 1.371(6) . ?
C42 H42 0.9500 . ?
C42 C43 1.393(6) . ?
C43 H43 0.9500 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 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 N1 C1 122.4(3) . . ?
C8 N1 C9 111.0(3) . . ?
C9 N1 C1 121.6(3) . . ?
C9 N2 C7 112.3(3) . . ?
C9 N2 C15 122.5(3) . . ?
C15 N2 C7 121.9(3) . . ?
C8 N3 H3 114(3) . . ?
N1 C1 H1A 109.3 . . ?
N1 C1 H1B 109.3 . . ?
N1 C1 C2 111.6(3) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C1 C2 C3 113.9(3) . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 C2 113.8(3) . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C3 C4 H4A 108.2 . . ?
C3 C4 H4B 108.2 . . ?
H4A C4 H4B 107.4 . . ?
C5 C4 C3 116.3(3) . . ?
C5 C4 H4A 108.2 . . ?
C5 C4 H4B 108.2 . . ?
C6 C5 C4 125.8(3) . . ?
C10 C5 C4 116.0(3) . . ?
C10 C5 C6 118.2(3) . . ?
C5 C6 C7 123.4(3) . . ?
C13 C6 C5 118.2(3) . . ?
C13 C6 C7 118.4(3) . . ?
N2 C7 C6 111.3(3) . . ?
N2 C7 C8 101.0(3) . . ?
N2 C7 C14 109.3(3) . . ?
C6 C7 C14 114.8(3) . . ?
C8 C7 C6 111.1(3) . . ?
C8 C7 C14 108.5(3) . . ?
N1 C8 C7 106.8(3) . . ?
N3 C8 N1 123.1(3) . . ?
N3 C8 C7 130.1(3) . . ?
O1 C9 N1 124.3(3) . . ?
O1 C9 N2 127.3(3) . . ?
N2 C9 N1 108.4(3) . . ?
C5 C10 H10 118.9 . . ?
C11 C10 C5 122.2(4) . . ?
C11 C10 H10 118.9 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.4(4) . . ?
C12 C11 H11 120.3 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.5(4) . . ?
C13 C12 H12 120.2 . . ?
C6 C13 H13 118.8 . . ?
C12 C13 C6 122.4(4) . . ?
C12 C13 H13 118.8 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C23 N4 C16 122.7(3) . . ?
C23 N4 C24 110.8(3) . . ?
C24 N4 C16 120.6(3) . . ?
C24 N5 C22 112.1(3) . . ?
C24 N5 C30 122.4(3) . . ?
C30 N5 C22 123.0(3) . . ?
C23 N6 H6 109(3) . . ?
N4 C16 H16A 109.2 . . ?
N4 C16 H16B 109.2 . . ?
N4 C16 C17 111.9(3) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C16 C17 H17A 108.7 . . ?
C16 C17 H17B 108.7 . . ?
C16 C17 C18 114.1(3) . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C17 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C17 C18 C19 114.2(3) . . ?
H18A C18 H18B 107.6 . . ?
C19 C18 H18A 108.7 . . ?
C19 C18 H18B 108.7 . . ?
C18 C19 H19A 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 C18 114.3(3) . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C21 C20 C19 126.3(3) . . ?
C25 C20 C19 115.5(3) . . ?
C25 C20 C21 118.2(3) . . ?
C20 C21 C22 122.9(3) . . ?
C28 C21 C20 118.3(3) . . ?
C28 C21 C22 118.7(3) . . ?
N5 C22 C21 113.2(3) . . ?
N5 C22 C23 101.1(3) . . ?
N5 C22 C29 108.7(3) . . ?
C23 C22 C21 108.1(3) . . ?
C29 C22 C21 114.7(3) . . ?
C29 C22 C23 110.1(3) . . ?
N4 C23 C22 106.9(3) . . ?
N6 C23 N4 123.7(3) . . ?
N6 C23 C22 129.3(3) . . ?
O2 C24 N4 124.2(3) . . ?
O2 C24 N5 126.9(3) . . ?
N5 C24 N4 108.8(3) . . ?
C20 C25 H25 118.8 . . ?
C26 C25 C20 122.3(4) . . ?
C26 C25 H25 118.8 . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.3(3) . . ?
C27 C26 H26 120.3 . . ?
C26 C27 H27 120.3 . . ?
C26 C27 C28 119.4(3) . . ?
C28 C27 H27 120.3 . . ?
C21 C28 H28 118.8 . . ?
C27 C28 C21 122.5(4) . . ?
C27 C28 H28 118.8 . . ?
C22 C29 H29A 109.5 . . ?
C22 C29 H29B 109.5 . . ?
C22 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N5 C30 H30A 109.5 . . ?
N5 C30 H30B 109.5 . . ?
N5 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C38 N7 C31 122.8(3) . . ?
C38 N7 C39 111.2(3) . . ?
C39 N7 C31 121.1(3) . . ?
C39 N8 C37 112.6(3) . . ?
C39 N8 C45 122.9(3) . . ?
C45 N8 C37 124.3(3) . . ?
C38 N9 H9 111(3) . . ?
N7 C31 H31A 109.3 . . ?
N7 C31 H31B 109.3 . . ?
N7 C31 C32 111.7(3) . . ?
H31A C31 H31B 107.9 . . ?
C32 C31 H31A 109.3 . . ?
C32 C31 H31B 109.3 . . ?
C31 C32 H32A 108.9 . . ?
C31 C32 H32B 108.9 . . ?
C31 C32 C33 113.2(3) . . ?
H32A C32 H32B 107.7 . . ?
C33 C32 H32A 108.9 . . ?
C33 C32 H32B 108.9 . . ?
C32 C33 H33A 108.8 . . ?
C32 C33 H33B 108.8 . . ?
C32 C33 C34 113.8(3) . . ?
H33A C33 H33B 107.7 . . ?
C34 C33 H33A 108.8 . . ?
C34 C33 H33B 108.8 . . ?
C33 C34 H34A 108.4 . . ?
C33 C34 H34B 108.4 . . ?
H34A C34 H34B 107.5 . . ?
C35 C34 C33 115.6(3) . . ?
C35 C34 H34A 108.4 . . ?
C35 C34 H34B 108.4 . . ?
C36 C35 C34 126.3(3) . . ?
C40 C35 C34 116.0(3) . . ?
C40 C35 C36 117.7(3) . . ?
C35 C36 C37 122.7(3) . . ?
C43 C36 C35 118.7(3) . . ?
C43 C36 C37 118.5(3) . . ?
N8 C37 C36 112.8(3) . . ?
N8 C37 C38 100.7(3) . . ?
N8 C37 C44 109.6(3) . . ?
C38 C37 C36 108.4(3) . . ?
C38 C37 C44 109.7(3) . . ?
C44 C37 C36 114.6(3) . . ?
N7 C38 C37 107.0(3) . . ?
N9 C38 N7 123.1(3) . . ?
N9 C38 C37 129.8(3) . . ?
O3 C39 N7 124.2(3) . . ?
O3 C39 N8 127.7(3) . . ?
N8 C39 N7 108.1(3) . . ?
C35 C40 H40 118.5 . . ?
C41 C40 C35 123.0(4) . . ?
C41 C40 H40 118.5 . . ?
C40 C41 H41 120.3 . . ?
C42 C41 C40 119.4(4) . . ?
C42 C41 H41 120.3 . . ?
C41 C42 H42 120.3 . . ?
C41 C42 C43 119.5(4) . . ?
C43 C42 H42 120.3 . . ?
C36 C43 H43 119.1 . . ?
C42 C43 C36 121.8(4) . . ?
C42 C43 H43 119.1 . . ?
C37 C44 H44A 109.5 . . ?
C37 C44 H44B 109.5 . . ?
C37 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N8 C45 H45A 109.5 . . ?
N8 C45 H45B 109.5 . . ?
N8 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM:Et2O'
####################################################################### 
# 
# 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_mm151
_database_code_depnum_ccdc_archive 'CCDC 1993735'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_audit_creation_date             2019-09-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H18 N2 O2'
_chemical_formula_sum            'C15 H18 N2 O2'
_chemical_formula_weight         258.31
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.6859(2)
_cell_length_b                   8.2156(2)
_cell_length_c                   16.9618(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.1200(10)
_cell_angle_gamma                90
_cell_volume                     1296.67(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5451
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.98
_cell_measurement_theta_min      2.20
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5929
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0696 before and 0.0491 after correction. The Ratio of minimum to maximum transmission is 0.7948. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.543
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.163
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            26574
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.058
_diffrn_reflns_theta_min         2.199
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3110
_reflns_number_total             3801
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.410
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3801
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      1.014
_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)+(0.0516P)²+0.4417P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1047
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C15(H15A,H15B,H15C)
;
_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
C1 C 0.42675(11) 0.45628(13) 0.40261(6) 0.0138(2) Uani 1 1 d . . . . .
C2 C 0.65054(11) 0.38918(12) 0.38605(6) 0.0129(2) Uani 1 1 d . . . . .
C3 C 0.59359(11) 0.25210(13) 0.42850(6) 0.0133(2) Uani 1 1 d . . . . .
C4 C 0.55045(13) 0.68257(13) 0.35903(7) 0.0189(2) Uani 1 1 d . . . . .
H4A H 0.5097 0.6770 0.2994 0.028 Uiso 1 1 calc GR . . . .
H4B H 0.6491 0.7240 0.3718 0.028 Uiso 1 1 calc GR . . . .
H4C H 0.4922 0.7557 0.3824 0.028 Uiso 1 1 calc GR . . . .
C5 C 0.80716(11) 0.42557(14) 0.43068(7) 0.0177(2) Uani 1 1 d . . . . .
H5A H 0.8382 0.5233 0.4071 0.027 Uiso 1 1 calc GR . . . .
H5B H 0.8672 0.3331 0.4245 0.027 Uiso 1 1 calc GR . . . .
H5C H 0.8167 0.4437 0.4891 0.027 Uiso 1 1 calc GR . . . .
C6 C 0.61961(11) 0.35126(12) 0.29308(6) 0.0132(2) Uani 1 1 d . . . . .
C7 C 0.68920(12) 0.45350(13) 0.24993(7) 0.0166(2) Uani 1 1 d . . . . .
H7 H 0.7620 0.5249 0.2800 0.020 Uiso 1 1 calc R . . . .
C8 C 0.65543(12) 0.45405(13) 0.16481(7) 0.0175(2) Uani 1 1 d . . . . .
H8 H 0.7052 0.5237 0.1373 0.021 Uiso 1 1 calc R . . . .
C9 C 0.54810(12) 0.35158(13) 0.12058(7) 0.0172(2) Uani 1 1 d . . . . .
H9 H 0.5208 0.3534 0.0623 0.021 Uiso 1 1 calc R . . . .
C10 C 0.48091(12) 0.24629(13) 0.16217(7) 0.0159(2) Uani 1 1 d . . . . .
H10 H 0.4086 0.1755 0.1311 0.019 Uiso 1 1 calc R . . . .
C11 C 0.51494(11) 0.23961(12) 0.24827(7) 0.0136(2) Uani 1 1 d . . . . .
C12 C 0.44012(12) 0.10052(13) 0.28073(7) 0.0161(2) Uani 1 1 d . . . . .
H12A H 0.5129 0.0481 0.3264 0.019 Uiso 1 1 calc R . . . .
H12B H 0.4105 0.0186 0.2364 0.019 Uiso 1 1 calc R . . . .
C13 C 0.30748(12) 0.13825(14) 0.31160(7) 0.0175(2) Uani 1 1 d . . . . .
H13A H 0.2600 0.2374 0.2835 0.021 Uiso 1 1 calc R . . . .
H13B H 0.2383 0.0472 0.2958 0.021 Uiso 1 1 calc R . . . .
C14 C 0.34176(11) 0.16413(13) 0.40442(7) 0.0156(2) Uani 1 1 d . . . . .
H14 H 0.3851 0.0610 0.4317 0.019 Uiso 1 1 calc R . . . .
C15 C 0.20903(12) 0.20006(15) 0.43250(8) 0.0218(2) Uani 1 1 d . . . . .
H15A H 0.2379 0.2259 0.4912 0.033 Uiso 1 1 calc GR . . . .
H15B H 0.1460 0.1045 0.4227 0.033 Uiso 1 1 calc GR . . . .
H15C H 0.1576 0.2930 0.4017 0.033 Uiso 1 1 calc GR . . . .
N1 N 0.45348(9) 0.29210(11) 0.42635(6) 0.01342(18) Uani 1 1 d . . . . .
N2 N 0.55111(9) 0.52066(10) 0.39402(6) 0.01412(18) Uani 1 1 d . . . . .
O1 O 0.31367(8) 0.52727(10) 0.39409(5) 0.01948(18) Uani 1 1 d . . . . .
O2 O 0.65651(9) 0.12824(9) 0.45622(5) 0.01777(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.4110(13) . ?
C1 N2 1.3598(13) . ?
C1 O1 1.2136(13) . ?
C2 C3 1.5204(14) . ?
C2 C5 1.5252(14) . ?
C2 C6 1.5527(15) . ?
C2 N2 1.4782(13) . ?
C3 N1 1.3869(13) . ?
C3 O2 1.2120(13) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 N2 1.4560(13) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.4034(14) . ?
C6 C11 1.4209(14) . ?
C7 H7 0.9500 . ?
C7 C8 1.3890(15) . ?
C8 H8 0.9500 . ?
C8 C9 1.3853(16) . ?
C9 H9 0.9500 . ?
C9 C10 1.3872(15) . ?
C10 H10 0.9500 . ?
C10 C11 1.4060(15) . ?
C11 C12 1.5348(14) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.5474(15) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.5310(15) . ?
C14 H14 1.0000 . ?
C14 C15 1.5188(15) . ?
C14 N1 1.4802(13) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
N2 C1 N1 107.73(9) . . ?
O1 C1 N1 125.55(10) . . ?
O1 C1 N2 126.68(10) . . ?
C3 C2 C5 110.60(9) . . ?
C3 C2 C6 109.83(8) . . ?
C5 C2 C6 115.36(9) . . ?
N2 C2 C3 99.59(8) . . ?
N2 C2 C5 113.26(9) . . ?
N2 C2 C6 107.02(8) . . ?
N1 C3 C2 107.05(8) . . ?
O2 C3 C2 126.60(9) . . ?
O2 C3 N1 126.30(10) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C2 115.11(9) . . ?
C7 C6 C11 118.81(10) . . ?
C11 C6 C2 125.49(9) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 C6 122.38(10) . . ?
C8 C7 H7 118.8 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.06(10) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.41(10) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 118.5 . . ?
C9 C10 C11 123.00(10) . . ?
C11 C10 H10 118.5 . . ?
C6 C11 C12 128.79(10) . . ?
C10 C11 C6 117.20(9) . . ?
C10 C11 C12 113.81(9) . . ?
C11 C12 H12A 107.5 . . ?
C11 C12 H12B 107.5 . . ?
C11 C12 C13 119.43(9) . . ?
H12A C12 H12B 107.0 . . ?
C13 C12 H12A 107.5 . . ?
C13 C12 H12B 107.5 . . ?
C12 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C14 C13 C12 114.36(9) . . ?
C14 C13 H13A 108.7 . . ?
C14 C13 H13B 108.7 . . ?
C13 C14 H14 107.6 . . ?
C15 C14 C13 112.88(9) . . ?
C15 C14 H14 107.6 . . ?
N1 C14 C13 106.96(8) . . ?
N1 C14 H14 107.6 . . ?
N1 C14 C15 113.99(9) . . ?
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 . . ?
C1 N1 C14 122.95(9) . . ?
C3 N1 C1 109.55(8) . . ?
C3 N1 C14 118.69(9) . . ?
C1 N2 C2 110.16(8) . . ?
C1 N2 C4 119.69(9) . . ?
C4 N2 C2 124.02(9) . . ?

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
C2 C3 N1 C1 -12.54(11) . . . . ?
C2 C3 N1 C14 135.91(9) . . . . ?
C2 C6 C7 C8 -169.15(10) . . . . ?
C2 C6 C11 C10 166.80(9) . . . . ?
C2 C6 C11 C12 -18.58(17) . . . . ?
C3 C2 C6 C7 -169.06(9) . . . . ?
C3 C2 C6 C11 19.81(13) . . . . ?
C3 C2 N2 C1 -24.11(10) . . . . ?
C3 C2 N2 C4 -176.29(9) . . . . ?
C5 C2 C3 N1 140.91(9) . . . . ?
C5 C2 C3 O2 -41.67(14) . . . . ?
C5 C2 C6 C7 -43.27(13) . . . . ?
C5 C2 C6 C11 145.60(10) . . . . ?
C5 C2 N2 C1 -141.56(9) . . . . ?
C5 C2 N2 C4 66.26(13) . . . . ?
C6 C2 C3 N1 -90.63(9) . . . . ?
C6 C2 C3 O2 86.79(13) . . . . ?
C6 C2 N2 C1 90.19(10) . . . . ?
C6 C2 N2 C4 -61.99(12) . . . . ?
C6 C7 C8 C9 0.77(16) . . . . ?
C6 C11 C12 C13 83.06(14) . . . . ?
C7 C6 C11 C10 -4.03(14) . . . . ?
C7 C6 C11 C12 170.59(10) . . . . ?
C7 C8 C9 C10 -2.58(16) . . . . ?
C8 C9 C10 C11 1.01(16) . . . . ?
C9 C10 C11 C6 2.33(15) . . . . ?
C9 C10 C11 C12 -173.09(10) . . . . ?
C10 C11 C12 C13 -102.18(11) . . . . ?
C11 C6 C7 C8 2.61(16) . . . . ?
C11 C12 C13 C14 -95.32(12) . . . . ?
C12 C13 C14 C15 -179.73(9) . . . . ?
C12 C13 C14 N1 54.12(11) . . . . ?
C13 C14 N1 C1 68.85(12) . . . . ?
C13 C14 N1 C3 -75.17(11) . . . . ?
C15 C14 N1 C1 -56.64(13) . . . . ?
C15 C14 N1 C3 159.34(10) . . . . ?
N1 C1 N2 C2 18.08(11) . . . . ?
N1 C1 N2 C4 171.63(9) . . . . ?
N2 C1 N1 C3 -3.00(11) . . . . ?
N2 C1 N1 C14 -149.85(9) . . . . ?
N2 C2 C3 N1 21.48(10) . . . . ?
N2 C2 C3 O2 -161.10(10) . . . . ?
N2 C2 C6 C7 83.74(11) . . . . ?
N2 C2 C6 C11 -87.38(11) . . . . ?
O1 C1 N1 C3 179.10(10) . . . . ?
O1 C1 N1 C14 32.25(16) . . . . ?
O1 C1 N2 C2 -164.05(10) . . . . ?
O1 C1 N2 C4 -10.50(17) . . . . ?
O2 C3 N1 C1 170.03(10) . . . . ?
O2 C3 N1 C14 -41.52(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM:n-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_testo1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1993734'
loop_
_audit_author_name
_audit_author_address
'Hazel A. Sparkes'
;University of Bristol
United Kingdom
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-12-11 downloaded from the CCDC.
;
_audit_creation_date             2020-01-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H22 N6 O2, 2(H2 O)'
_chemical_formula_sum            'C18 H26 N6 O4'
_chemical_formula_weight         390.45
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.3617(3)
_cell_length_b                   13.8207(6)
_cell_length_c                   16.0698(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1857.10(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3845
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.89
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0681 before and 0.0537 after correction. The Ratio of minimum to maximum transmission is 0.8279. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.443
_exptl_crystal_size_mid          0.367
_exptl_crystal_size_min          0.154
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17119
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.969
_diffrn_reflns_theta_min         1.943
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_device_type  'Bruker Apex II kappa CCDC area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3893
_reflns_number_total             4432
_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       'SAINT V8.38A (Bruker, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_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         0.246
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4432
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.017
_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)+(0.0354P)²+0.2721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0800
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3-H3B \\sim O4-H4E \\sim O4-H4D \\sim O3-H3A
 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10)
3.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.40538(19) 0.29985(11) 0.74758(10) 0.0219(4) Uani 1 1 d . . . . .
O2 O 0.71944(18) 0.29063(10) 0.64921(9) 0.0189(3) Uani 1 1 d . . . . .
O4 O 0.4527(2) 0.66430(14) 0.46646(11) 0.0290(4) Uani 1 1 d D . . . .
N1 N 0.3492(2) 0.46067(13) 0.71828(11) 0.0143(4) Uani 1 1 d . . . . .
N2 N 0.4918(2) 0.42534(12) 0.83103(11) 0.0146(4) Uani 1 1 d . . . . .
N3 N 0.3097(2) 0.62813(14) 0.73124(12) 0.0168(4) Uani 1 1 d . . . . .
N4 N 0.6184(2) 0.44495(12) 0.62504(11) 0.0140(4) Uani 1 1 d . . . . .
N5 N 0.7959(2) 0.42354(13) 0.72649(11) 0.0148(4) Uani 1 1 d . . . . .
N6 N 0.5862(2) 0.61246(14) 0.62203(12) 0.0175(4) Uani 1 1 d . . . . .
C1 C 0.4157(2) 0.38514(15) 0.76572(14) 0.0154(4) Uani 1 1 d . . . . .
C2 C 0.4603(2) 0.52926(14) 0.83849(13) 0.0128(4) Uani 1 1 d . . . . .
C3 C 0.3692(2) 0.54971(15) 0.75722(13) 0.0130(4) Uani 1 1 d . . . . .
C4 C 0.5641(3) 0.36859(16) 0.89680(15) 0.0211(5) Uani 1 1 d . . . . .
H4A H 0.489682 0.363809 0.943747 0.032 Uiso 1 1 calc GR . . . .
H4B H 0.663039 0.399967 0.915222 0.032 Uiso 1 1 calc GR . . . .
H4C H 0.588426 0.303611 0.875945 0.032 Uiso 1 1 calc GR . . . .
C5 C 0.3356(2) 0.54388(16) 0.90841(14) 0.0191(5) Uani 1 1 d . . . . .
H5A H 0.242930 0.502119 0.898087 0.029 Uiso 1 1 calc GR . . . .
H5B H 0.301144 0.611654 0.909284 0.029 Uiso 1 1 calc GR . . . .
H5C H 0.383506 0.527121 0.962154 0.029 Uiso 1 1 calc GR . . . .
C6 C 0.6177(2) 0.58724(14) 0.85067(13) 0.0130(4) Uani 1 1 d . . . . .
C7 C 0.6237(3) 0.64524(15) 0.92168(14) 0.0164(4) Uani 1 1 d . . . . .
H7 H 0.531021 0.648611 0.955752 0.020 Uiso 1 1 calc R . . . .
C8 C 0.7569(3) 0.69827(16) 0.94548(14) 0.0196(5) Uani 1 1 d . . . . .
H8 H 0.754890 0.736384 0.994671 0.024 Uiso 1 1 calc R . . . .
C9 C 0.8916(3) 0.69482(16) 0.89694(14) 0.0199(5) Uani 1 1 d . . . . .
H9 H 0.984597 0.730098 0.912175 0.024 Uiso 1 1 calc R . . . .
C10 C 0.8899(3) 0.63906(15) 0.82529(15) 0.0181(5) Uani 1 1 d . . . . .
H10 H 0.983561 0.637708 0.791875 0.022 Uiso 1 1 calc R . . . .
C11 C 0.7579(2) 0.58467(15) 0.79940(13) 0.0138(4) Uani 1 1 d . . . . .
C12 C 0.7834(2) 0.52933(15) 0.71676(13) 0.0142(4) Uani 1 1 d . . . . .
C13 C 0.6500(2) 0.53779(15) 0.65264(13) 0.0139(4) Uani 1 1 d . . . . .
C14 C 0.7136(2) 0.37647(15) 0.66634(13) 0.0145(4) Uani 1 1 d . . . . .
C15 C 0.9311(3) 0.56367(17) 0.66713(14) 0.0204(5) Uani 1 1 d . . . . .
H15A H 1.028598 0.547533 0.698036 0.031 Uiso 1 1 calc GR . . . .
H15B H 0.925393 0.633865 0.659039 0.031 Uiso 1 1 calc GR . . . .
H15C H 0.933141 0.531390 0.612845 0.031 Uiso 1 1 calc GR . . . .
C16 C 0.9262(3) 0.37743(17) 0.77117(15) 0.0219(5) Uani 1 1 d . . . . .
H16A H 1.023227 0.379108 0.736971 0.033 Uiso 1 1 calc GR . . . .
H16B H 0.897909 0.310066 0.783226 0.033 Uiso 1 1 calc GR . . . .
H16C H 0.945488 0.411999 0.823464 0.033 Uiso 1 1 calc GR . . . .
C17 C 0.4725(2) 0.41820(16) 0.58118(14) 0.0167(5) Uani 1 1 d . . . . .
H17A H 0.471298 0.347294 0.572435 0.020 Uiso 1 1 calc R . . . .
H17B H 0.471752 0.449645 0.525834 0.020 Uiso 1 1 calc R . . . .
C18 C 0.3197(3) 0.44827(16) 0.62963(14) 0.0168(4) Uani 1 1 d . . . . .
H18A H 0.278438 0.509731 0.606392 0.020 Uiso 1 1 calc R . . . .
H18B H 0.236411 0.398188 0.621720 0.020 Uiso 1 1 calc R . . . .
O3 O 0.1788(2) 0.68470(12) 0.56793(11) 0.0249(4) Uani 1 1 d D . . . .
H6 H 0.616(3) 0.6650(18) 0.6483(15) 0.020(6) Uiso 1 1 d . . . . .
H3 H 0.335(3) 0.674(2) 0.7648(17) 0.030(8) Uiso 1 1 d . . . . .
H4D H 0.515(3) 0.7152(19) 0.449(2) 0.058(11) Uiso 1 1 d D . . . .
H4E H 0.499(4) 0.639(2) 0.5139(16) 0.062(11) Uiso 1 1 d D . . . .
H3A H 0.258(3) 0.685(2) 0.5281(15) 0.044(9) Uiso 1 1 d D . . . .
H3B H 0.225(4) 0.667(3) 0.6176(16) 0.080(13) Uiso 1 1 d 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
O1 C1 1.217(3) . ?
O2 C14 1.219(2) . ?
O4 H4D 0.920(19) . ?
O4 H4E 0.922(19) . ?
N1 C1 1.407(3) . ?
N1 C3 1.391(3) . ?
N1 C18 1.456(3) . ?
N2 C1 1.347(3) . ?
N2 C2 1.465(3) . ?
N2 C4 1.448(3) . ?
N3 C3 1.263(3) . ?
N3 H3 0.86(3) . ?
N4 C13 1.383(3) . ?
N4 C14 1.404(3) . ?
N4 C17 1.457(3) . ?
N5 C12 1.474(3) . ?
N5 C14 1.353(3) . ?
N5 C16 1.452(3) . ?
N6 C13 1.262(3) . ?
N6 H6 0.88(3) . ?
C2 C3 1.538(3) . ?
C2 C5 1.547(3) . ?
C2 C6 1.553(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.396(3) . ?
C6 C11 1.433(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.387(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.370(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.399(3) . ?
C11 C12 1.547(3) . ?
C12 C13 1.523(3) . ?
C12 C15 1.545(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.553(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
O3 H3A 0.919(19) . ?
O3 H3B 0.920(19) . ?

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
H4D O4 H4E 108(3) . . ?
C1 N1 C18 120.65(18) . . ?
C3 N1 C1 111.42(18) . . ?
C3 N1 C18 124.39(18) . . ?
C1 N2 C2 112.54(17) . . ?
C1 N2 C4 122.84(18) . . ?
C4 N2 C2 123.09(18) . . ?
C3 N3 H3 109.3(18) . . ?
C13 N4 C14 111.44(17) . . ?
C13 N4 C17 123.41(17) . . ?
C14 N4 C17 122.18(17) . . ?
C14 N5 C12 111.41(17) . . ?
C14 N5 C16 121.59(18) . . ?
C16 N5 C12 122.74(18) . . ?
C13 N6 H6 111.7(16) . . ?
O1 C1 N1 124.1(2) . . ?
O1 C1 N2 128.3(2) . . ?
N2 C1 N1 107.62(17) . . ?
N2 C2 C3 101.51(16) . . ?
N2 C2 C5 107.97(17) . . ?
N2 C2 C6 111.36(16) . . ?
C3 C2 C5 104.98(16) . . ?
C3 C2 C6 115.60(16) . . ?
C5 C2 C6 114.38(17) . . ?
N1 C3 C2 106.20(17) . . ?
N3 C3 N1 124.3(2) . . ?
N3 C3 C2 129.28(19) . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C2 115.45(18) . . ?
C7 C6 C11 117.07(19) . . ?
C11 C6 C2 127.43(18) . . ?
C6 C7 H7 118.1 . . ?
C8 C7 C6 123.9(2) . . ?
C8 C7 H7 118.1 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.0(2) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 120.5 . . ?
C8 C9 C10 118.9(2) . . ?
C10 C9 H9 120.5 . . ?
C9 C10 H10 118.2 . . ?
C9 C10 C11 123.7(2) . . ?
C11 C10 H10 118.2 . . ?
C6 C11 C12 128.21(18) . . ?
C10 C11 C6 117.45(19) . . ?
C10 C11 C12 114.33(18) . . ?
N5 C12 C11 114.15(17) . . ?
N5 C12 C13 101.52(16) . . ?
N5 C12 C15 107.62(17) . . ?
C13 C12 C11 116.21(17) . . ?
C13 C12 C15 102.28(17) . . ?
C15 C12 C11 113.68(17) . . ?
N4 C13 C12 106.60(17) . . ?
N6 C13 N4 123.6(2) . . ?
N6 C13 C12 129.5(2) . . ?
O2 C14 N4 124.9(2) . . ?
O2 C14 N5 127.5(2) . . ?
N5 C14 N4 107.58(17) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N5 C16 H16A 109.5 . . ?
N5 C16 H16B 109.5 . . ?
N5 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N4 C17 H17A 109.2 . . ?
N4 C17 H17B 109.2 . . ?
N4 C17 C18 112.25(17) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
N1 C18 C17 112.50(17) . . ?
N1 C18 H18A 109.1 . . ?
N1 C18 H18B 109.1 . . ?
C17 C18 H18A 109.1 . . ?
C17 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
H3A O3 H3B 108(3) . . ?

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
O4 H4D O3 0.920(19) 1.97(2) 2.869(3) 167(3) 4_566 yes
O4 H4E N6 0.922(19) 1.92(2) 2.830(3) 168(3) . yes
O3 H3A O4 0.919(19) 1.93(2) 2.826(3) 164(3) . 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
N2 C2 C3 N1 4.18(19) . . . . ?
N2 C2 C3 N3 178.6(2) . . . . ?
N2 C2 C6 C7 -123.7(2) . . . . ?
N2 C2 C6 C11 53.6(3) . . . . ?
N4 C17 C18 N1 -22.5(3) . . . . ?
N5 C12 C13 N4 -8.1(2) . . . . ?
N5 C12 C13 N6 178.2(2) . . . . ?
C1 N1 C3 N3 -174.1(2) . . . . ?
C1 N1 C3 C2 0.6(2) . . . . ?
C1 N1 C18 C17 -55.8(3) . . . . ?
C1 N2 C2 C3 -8.1(2) . . . . ?
C1 N2 C2 C5 102.0(2) . . . . ?
C1 N2 C2 C6 -131.64(18) . . . . ?
C2 N2 C1 O1 -172.4(2) . . . . ?
C2 N2 C1 N1 8.8(2) . . . . ?
C2 C6 C7 C8 176.48(19) . . . . ?
C2 C6 C11 C10 -176.26(19) . . . . ?
C2 C6 C11 C12 4.4(3) . . . . ?
C3 N1 C1 O1 175.4(2) . . . . ?
C3 N1 C1 N2 -5.7(2) . . . . ?
C3 N1 C18 C17 101.1(2) . . . . ?
C3 C2 C6 C7 121.11(19) . . . . ?
C3 C2 C6 C11 -61.6(3) . . . . ?
C4 N2 C1 O1 -6.1(3) . . . . ?
C4 N2 C1 N1 175.12(18) . . . . ?
C4 N2 C2 C3 -174.33(18) . . . . ?
C4 N2 C2 C5 -64.3(2) . . . . ?
C4 N2 C2 C6 62.1(2) . . . . ?
C5 C2 C3 N1 -108.17(18) . . . . ?
C5 C2 C3 N3 66.3(3) . . . . ?
C5 C2 C6 C7 -1.0(3) . . . . ?
C5 C2 C6 C11 176.30(19) . . . . ?
C6 C2 C3 N1 124.82(18) . . . . ?
C6 C2 C3 N3 -60.8(3) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C6 C11 C12 N5 -71.2(3) . . . . ?
C6 C11 C12 C13 46.5(3) . . . . ?
C6 C11 C12 C15 164.9(2) . . . . ?
C7 C6 C11 C10 1.0(3) . . . . ?
C7 C6 C11 C12 -178.32(19) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C9 C10 C11 C6 -0.2(3) . . . . ?
C9 C10 C11 C12 179.21(19) . . . . ?
C10 C11 C12 N5 109.5(2) . . . . ?
C10 C11 C12 C13 -132.8(2) . . . . ?
C10 C11 C12 C15 -14.5(3) . . . . ?
C11 C6 C7 C8 -1.1(3) . . . . ?
C11 C12 C13 N4 -132.54(18) . . . . ?
C11 C12 C13 N6 53.8(3) . . . . ?
C12 N5 C14 O2 167.9(2) . . . . ?
C12 N5 C14 N4 -11.6(2) . . . . ?
C13 N4 C14 O2 -173.6(2) . . . . ?
C13 N4 C14 N5 5.9(2) . . . . ?
C13 N4 C17 C18 -53.4(3) . . . . ?
C14 N4 C13 N6 176.1(2) . . . . ?
C14 N4 C13 C12 1.9(2) . . . . ?
C14 N4 C17 C18 105.4(2) . . . . ?
C14 N5 C12 C11 137.99(18) . . . . ?
C14 N5 C12 C13 12.2(2) . . . . ?
C14 N5 C12 C15 -94.9(2) . . . . ?
C15 C12 C13 N4 103.04(18) . . . . ?
C15 C12 C13 N6 -70.6(3) . . . . ?
C16 N5 C12 C11 -64.9(3) . . . . ?
C16 N5 C12 C13 169.23(18) . . . . ?
C16 N5 C12 C15 62.2(2) . . . . ?
C16 N5 C14 O2 10.5(3) . . . . ?
C16 N5 C14 N4 -168.97(18) . . . . ?
C17 N4 C13 N6 -23.1(3) . . . . ?
C17 N4 C13 C12 162.73(18) . . . . ?
C17 N4 C14 O2 25.3(3) . . . . ?
C17 N4 C14 N5 -155.23(18) . . . . ?
C18 N1 C1 O1 -24.9(3) . . . . ?
C18 N1 C1 N2 153.93(18) . . . . ?
C18 N1 C3 N3 27.1(3) . . . . ?
C18 N1 C3 C2 -158.13(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
