# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_2011307640_2_0m
_audit_block_doi                 10.5517/ccdc.csd.cc26vgr9
_database_code_depnum_ccdc_archive 'CCDC 2051231'
loop_
_audit_author_name
_audit_author_address
Chen-Li
;zhejiang university of technology
China
;
_audit_update_record             
;
2020-12-18 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;
_audit_creation_date             2020-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H19 N O3'
_chemical_formula_sum            'C17 H19 N O3'
_chemical_formula_weight         285.33
_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 0.0148 0.0070 '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 0.0253 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0412 0.0250 '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                   7.8954(13)
_cell_length_b                   10.2306(15)
_cell_length_c                   10.8425(17)
_cell_angle_alpha                65.530(10)
_cell_angle_beta                 73.962(12)
_cell_angle_gamma                71.657(11)
_cell_volume                     745.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2569
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      54.53
_cell_measurement_theta_min      4.24
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.452
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1672 before and 0.0874 after correction. The Ratio of minimum to maximum transmission is 0.5730. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_unetI/netI     0.0918
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7277
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.568
_diffrn_reflns_theta_min         3.954
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1550
_reflns_number_total             2778
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2778
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0743
_refine_ls_restrained_S_all      1.042
_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)+(0.0974P)²+0.1798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1739
_refine_ls_wR_factor_ref         0.2163
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C13(H13), C15(H15)
2.d X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5121(3) 0.1324(2) 0.3299(2) 0.0506(6) Uani 1 1 d . . . . .
O2 O 0.7412(3) 0.5837(2) 0.2126(3) 0.0551(7) Uani 1 1 d . . . . .
O3 O 0.1455(3) 0.7277(2) 0.4638(2) 0.0532(7) Uani 1 1 d . . . . .
N1 N 0.2725(3) 0.1371(3) 0.5005(3) 0.0487(7) Uani 1 1 d . . . . .
H1A H 0.324365 0.052973 0.558283 0.058 Uiso 1 1 calc R . . . .
H1B H 0.163326 0.184328 0.526877 0.058 Uiso 1 1 calc R . . . .
C1 C 0.2620(4) 0.3421(3) 0.2826(3) 0.0436(8) Uani 1 1 d . . . . .
H1 H 0.129494 0.355302 0.320085 0.052 Uiso 1 1 calc R . . . .
C2 C 0.3589(4) 0.1928(3) 0.3735(4) 0.0433(8) Uani 1 1 d . . . . .
C3 C 0.2898(4) 0.3491(3) 0.1341(3) 0.0475(9) Uani 1 1 d . . . . .
H3A H 0.234365 0.449678 0.075751 0.057 Uiso 1 1 calc R . . . .
H3B H 0.420948 0.328043 0.097329 0.057 Uiso 1 1 calc R . . . .
C4 C 0.2046(4) 0.2380(3) 0.1289(3) 0.0467(8) Uani 1 1 d . . . . .
C5 C 0.3078(5) 0.1053(4) 0.1169(4) 0.0554(9) Uani 1 1 d . . . . .
H5 H 0.435901 0.084884 0.106791 0.066 Uiso 1 1 calc R . . . .
C6 C 0.2265(6) 0.0015(4) 0.1196(4) 0.0649(11) Uani 1 1 d . . . . .
H6 H 0.299077 -0.088704 0.110335 0.078 Uiso 1 1 calc R . . . .
C7 C 0.0417(6) 0.0291(4) 0.1356(4) 0.0685(11) Uani 1 1 d . . . . .
H7 H -0.014010 -0.042706 0.139495 0.082 Uiso 1 1 calc R . . . .
C8 C -0.0628(5) 0.1613(5) 0.1461(4) 0.0686(11) Uani 1 1 d . . . . .
H8 H -0.190744 0.181492 0.155842 0.082 Uiso 1 1 calc R . . . .
C9 C 0.0190(4) 0.2647(4) 0.1424(4) 0.0575(10) Uani 1 1 d . . . . .
H9 H -0.054083 0.355753 0.149267 0.069 Uiso 1 1 calc R . . . .
C10 C 0.3279(4) 0.4600(3) 0.2955(3) 0.0426(8) Uani 1 1 d . . . . .
C11 C 0.2119(4) 0.5469(3) 0.3682(3) 0.0435(8) Uani 1 1 d . . . . .
H11 H 0.090253 0.537504 0.403059 0.052 Uiso 1 1 calc R . . . .
C12 C 0.2723(4) 0.6477(3) 0.3907(3) 0.0437(8) Uani 1 1 d . . . . .
C13 C 0.4493(4) 0.6629(3) 0.3411(3) 0.0462(9) Uani 1 1 d . . . . .
H13 H 0.491417 0.730120 0.358294 0.055 Uiso 1 1 calc R . . . .
C14 C 0.5638(4) 0.5778(3) 0.2659(4) 0.0437(8) Uani 1 1 d . . . . .
C15 C 0.5045(4) 0.4760(3) 0.2440(4) 0.0472(8) Uani 1 1 d . . . . .
H15 H 0.585132 0.417337 0.193596 0.057 Uiso 1 1 calc R . . . .
C16 C 0.8045(4) 0.6945(4) 0.2226(4) 0.0535(9) Uani 1 1 d . . . . .
H16A H 0.732263 0.792116 0.176005 0.080 Uiso 1 1 calc GR . . . .
H16B H 0.931876 0.688131 0.179075 0.080 Uiso 1 1 calc GR . . . .
H16C H 0.792851 0.679441 0.319667 0.080 Uiso 1 1 calc GR . . . .
C17 C 0.2044(4) 0.8279(4) 0.4958(4) 0.0583(10) Uani 1 1 d . . . . .
H17A H 0.243735 0.904430 0.410396 0.087 Uiso 1 1 calc GR . . . .
H17B H 0.305536 0.773593 0.546639 0.087 Uiso 1 1 calc GR . . . .
H17C H 0.103961 0.874000 0.552207 0.087 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.235(3) . ?
O2 C14 1.370(3) . ?
O2 C16 1.427(3) . ?
O3 C12 1.372(4) . ?
O3 C17 1.440(4) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N1 C2 1.327(4) . ?
C1 H1 1.0000 . ?
C1 C2 1.525(4) . ?
C1 C3 1.538(5) . ?
C1 C10 1.522(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.518(4) . ?
C4 C5 1.383(4) . ?
C4 C9 1.381(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(5) . ?
C6 H6 0.9500 . ?
C6 C7 1.371(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.376(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.385(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.386(4) . ?
C10 C15 1.386(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(4) . ?
C12 C13 1.384(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(4) . ?
C14 C15 1.391(4) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
C14 O2 C16 117.7(2) . . ?
C12 O3 C17 117.3(2) . . ?
H1A N1 H1B 120.0 . . ?
C2 N1 H1A 120.0 . . ?
C2 N1 H1B 120.0 . . ?
C2 C1 H1 108.0 . . ?
C2 C1 C3 111.2(2) . . ?
C3 C1 H1 108.0 . . ?
C10 C1 H1 108.0 . . ?
C10 C1 C2 107.3(2) . . ?
C10 C1 C3 114.0(3) . . ?
O1 C2 N1 123.3(3) . . ?
O1 C2 C1 120.3(3) . . ?
N1 C2 C1 116.3(3) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 C1 110.6(2) . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C5 C4 C3 121.7(3) . . ?
C9 C4 C3 120.2(3) . . ?
C9 C4 C5 118.1(3) . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.7(3) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.9(3) . . ?
C9 C8 H8 120.1 . . ?
C4 C9 C8 121.3(3) . . ?
C4 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C11 C10 C1 119.2(3) . . ?
C11 C10 C15 119.2(3) . . ?
C15 C10 C1 121.5(3) . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
O3 C12 C11 115.3(3) . . ?
O3 C12 C13 124.0(3) . . ?
C13 C12 C11 120.7(3) . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 118.6(3) . . ?
C14 C13 H13 120.7 . . ?
O2 C14 C13 123.4(3) . . ?
O2 C14 C15 115.6(3) . . ?
C13 C14 C15 121.0(3) . . ?
C10 C15 C14 120.1(3) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_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_2011307640_1_0m
_audit_block_doi                 10.5517/ccdc.csd.cc26vgm5
_database_code_depnum_ccdc_archive 'CCDC 2051227'
loop_
_audit_author_name
_audit_author_address
Chen-Li
;zhejiang university of technology
China
;
_audit_update_record             
;
2020-12-18 deposited with the CCDC.	2021-07-26 downloaded from the CCDC.
;
_audit_creation_date             2020-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N'
_chemical_formula_sum            'C19 H15 N'
_chemical_formula_weight         257.32
_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 0.0148 0.0070 '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 0.0253 0.0136 '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                   6.7162(7)
_cell_length_b                   7.9031(8)
_cell_length_c                   53.511(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2840.3(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5546
_cell_measurement_temperature    208(2)
_cell_measurement_theta_max      54.925
_cell_measurement_theta_min      4.314
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.343
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6544
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1304 before and 0.0511 after correction. The Ratio of minimum to maximum transmission is 0.8716. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       65
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_number            9909
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.905
_diffrn_reflns_theta_min         4.313
_diffrn_ambient_temperature      208.14
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2130
_reflns_number_total             2677
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.145
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2677
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0428
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+0.8375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1065
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0650(2) 0.4572(2) 0.64534(3) 0.0536(4) Uani 1 1 d . . . . .
C1 C 0.6767(2) 0.48621(19) 0.59903(3) 0.0366(4) Uani 1 1 d . . . . .
H1 H 0.765735 0.550621 0.608683 0.044 Uiso 1 1 calc R . . . .
C2 C 0.7287(2) 0.4388(2) 0.57538(3) 0.0394(4) Uani 1 1 d . . . . .
H2 H 0.853389 0.470897 0.568976 0.047 Uiso 1 1 calc R . . . .
C3 C 0.5978(2) 0.34195(18) 0.56031(3) 0.0354(4) Uani 1 1 d . . . . .
C4 C 0.6461(3) 0.2912(2) 0.53570(3) 0.0463(4) Uani 1 1 d . . . . .
H4 H 0.769305 0.322628 0.528771 0.056 Uiso 1 1 calc R . . . .
C5 C 0.5158(3) 0.1970(2) 0.52188(3) 0.0511(5) Uani 1 1 d . . . . .
H5 H 0.550220 0.164055 0.505570 0.061 Uiso 1 1 calc R . . . .
C6 C 0.3311(3) 0.1493(2) 0.53185(3) 0.0467(4) Uani 1 1 d . . . . .
H6 H 0.242677 0.084185 0.522205 0.056 Uiso 1 1 calc R . . . .
C7 C 0.2792(3) 0.19682(19) 0.55551(3) 0.0399(4) Uani 1 1 d . . . . .
H7 H 0.154708 0.164523 0.561982 0.048 Uiso 1 1 calc R . . . .
C8 C 0.4104(2) 0.29413(18) 0.57040(3) 0.0328(3) Uani 1 1 d . . . . .
C9 C 0.3613(2) 0.34519(18) 0.59500(3) 0.0325(3) Uani 1 1 d . . . . .
H9 H 0.237591 0.313682 0.601757 0.039 Uiso 1 1 calc R . . . .
C10 C 0.4897(2) 0.43929(17) 0.60918(2) 0.0308(3) Uani 1 1 d . . . . .
C11 C 0.4437(2) 0.49196(18) 0.63592(3) 0.0317(3) Uani 1 1 d . . . . .
H11 H 0.481719 0.612209 0.637952 0.038 Uiso 1 1 calc R . . . .
C12 C 0.2301(2) 0.47592(19) 0.64125(3) 0.0361(4) Uani 1 1 d . . . . .
C13 C 0.5622(2) 0.38609(19) 0.65518(3) 0.0336(3) Uani 1 1 d . . . . .
H13A H 0.522484 0.267196 0.653688 0.040 Uiso 1 1 calc R . . . .
H13B H 0.704354 0.393510 0.651214 0.040 Uiso 1 1 calc R . . . .
C14 C 0.5305(2) 0.44295(18) 0.68180(3) 0.0316(3) Uani 1 1 d . . . . .
C15 C 0.3957(2) 0.3633(2) 0.69746(3) 0.0402(4) Uani 1 1 d . . . . .
H15 H 0.321095 0.271142 0.691487 0.048 Uiso 1 1 calc R . . . .
C16 C 0.3699(2) 0.4179(2) 0.72183(3) 0.0468(4) Uani 1 1 d . . . . .
H16 H 0.278221 0.362273 0.732262 0.056 Uiso 1 1 calc R . . . .
C17 C 0.4773(3) 0.5530(2) 0.73092(3) 0.0470(4) Uani 1 1 d . . . . .
H17 H 0.459503 0.589682 0.747477 0.056 Uiso 1 1 calc R . . . .
C18 C 0.6112(3) 0.6337(2) 0.71548(3) 0.0491(4) Uani 1 1 d . . . . .
H18 H 0.684731 0.726417 0.721476 0.059 Uiso 1 1 calc R . . . .
C19 C 0.6375(2) 0.5785(2) 0.69116(3) 0.0438(4) Uani 1 1 d . . . . .
H19 H 0.729864 0.633991 0.680819 0.053 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C12 1.140(2) . ?
C1 H1 0.9400 . ?
C1 C2 1.366(2) . ?
C1 C10 1.417(2) . ?
C2 H2 0.9400 . ?
C2 C3 1.417(2) . ?
C3 C4 1.414(2) . ?
C3 C8 1.421(2) . ?
C4 H4 0.9400 . ?
C4 C5 1.366(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.402(2) . ?
C6 H6 0.9400 . ?
C6 C7 1.366(2) . ?
C7 H7 0.9400 . ?
C7 C8 1.415(2) . ?
C8 C9 1.4154(19) . ?
C9 H9 0.9400 . ?
C9 C10 1.3683(19) . ?
C10 C11 1.5221(19) . ?
C11 H11 0.9900 . ?
C11 C12 1.468(2) . ?
C11 C13 1.5476(19) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 C14 1.5086(19) . ?
C14 C15 1.385(2) . ?
C14 C19 1.384(2) . ?
C15 H15 0.9400 . ?
C15 C16 1.384(2) . ?
C16 H16 0.9400 . ?
C16 C17 1.377(2) . ?
C17 H17 0.9400 . ?
C17 C18 1.377(2) . ?
C18 H18 0.9400 . ?
C18 C19 1.384(2) . ?
C19 H19 0.9400 . ?

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 H1 119.7 . . ?
C2 C1 C10 120.64(14) . . ?
C10 C1 H1 119.7 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.14(14) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C8 118.48(13) . . ?
C4 C3 C2 122.72(15) . . ?
C4 C3 C8 118.80(14) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.75(16) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.52(15) . . ?
C6 C5 H5 119.7 . . ?
C5 C6 H6 119.9 . . ?
C7 C6 C5 120.29(16) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C8 120.81(16) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 C3 118.83(14) . . ?
C9 C8 C3 118.93(13) . . ?
C9 C8 C7 122.24(14) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 C8 121.59(14) . . ?
C10 C9 H9 119.2 . . ?
C1 C10 C11 117.93(13) . . ?
C9 C10 C1 119.22(13) . . ?
C9 C10 C11 122.82(13) . . ?
C10 C11 H11 108.3 . . ?
C10 C11 C13 111.96(11) . . ?
C12 C11 C10 110.94(12) . . ?
C12 C11 H11 108.3 . . ?
C12 C11 C13 109.04(12) . . ?
C13 C11 H11 108.3 . . ?
N1 C12 C11 177.51(17) . . ?
C11 C13 H13A 108.9 . . ?
C11 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C11 113.28(12) . . ?
C14 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C15 C14 C13 121.88(14) . . ?
C19 C14 C13 119.94(13) . . ?
C19 C14 C15 118.18(14) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.68(15) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.56(15) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.30(15) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.07(16) . . ?
C19 C18 H18 120.0 . . ?
C14 C19 H19 119.4 . . ?
C18 C19 C14 121.21(15) . . ?
C18 C19 H19 119.4 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
