# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_sa2890
_database_code_depnum_ccdc_archive 'CCDC 1958826'
loop_
_audit_author_name
_audit_author_address
'lei zhang'
;hebei normal university
China
;
_audit_update_record             
;
2019-10-11 deposited with the CCDC.	2020-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 Br N O'
_chemical_formula_sum            'C19 H20 Br N O'
_chemical_formula_weight         358.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   8.238(4)
_cell_length_b                   25.162(10)
_cell_length_c                   8.883(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.429(5)
_cell_angle_gamma                90.00
_cell_volume                     1676.5(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5240
_cell_measurement_theta_min      1.62
_cell_measurement_theta_max      27.47

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    2.453
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5804
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18257
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         27.49
_reflns_number_total             3837
_reflns_number_gt                3594
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0351P)²+1.2359P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3837
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.37909(4) 0.561020(10) 0.73995(4) 0.04600(11) Uani 1 1 d . . .
O1 O -0.1032(2) 0.27473(6) 0.6519(2) 0.0336(4) Uani 1 1 d . . .
N1 N 0.0315(2) 0.34282(7) 0.5808(2) 0.0259(4) Uani 1 1 d . . .
C1 C 0.1127(3) 0.38584(9) 0.8972(3) 0.0250(4) Uani 1 1 d . . .
H1 H 0.0948 0.4120 0.9737 0.030 Uiso 1 1 calc R . .
C2 C -0.0653(3) 0.35601(9) 0.8051(3) 0.0254(4) Uani 1 1 d . . .
H2 H -0.0876 0.3332 0.8868 0.030 Uiso 1 1 calc R . .
C3 C -0.0474(3) 0.32008(9) 0.6750(3) 0.0253(4) Uani 1 1 d . . .
C4 C 0.0366(4) 0.31260(10) 0.4422(3) 0.0358(5) Uani 1 1 d . . .
H4A H 0.0021 0.2757 0.4487 0.054 Uiso 1 1 calc R . .
H4B H 0.1577 0.3135 0.4473 0.054 Uiso 1 1 calc R . .
H4C H -0.0464 0.3284 0.3379 0.054 Uiso 1 1 calc R . .
C5 C 0.1070(3) 0.39432(8) 0.6139(3) 0.0233(4) Uani 1 1 d . . .
C6 C 0.1415(3) 0.42228(9) 0.4947(3) 0.0279(5) Uani 1 1 d . . .
H6 H 0.1099 0.4072 0.3882 0.034 Uiso 1 1 calc R . .
C7 C 0.2218(3) 0.47207(9) 0.5308(3) 0.0311(5) Uani 1 1 d . . .
H7 H 0.2457 0.4911 0.4498 0.037 Uiso 1 1 calc R . .
C8 C 0.2662(3) 0.49352(9) 0.6854(3) 0.0299(5) Uani 1 1 d . . .
C9 C 0.2305(3) 0.46655(9) 0.8050(3) 0.0277(5) Uani 1 1 d . . .
H9 H 0.2601 0.4822 0.9104 0.033 Uiso 1 1 calc R . .
C10 C 0.1516(3) 0.41668(9) 0.7701(3) 0.0240(4) Uani 1 1 d . . .
C11 C 0.2610(3) 0.34811(8) 1.0013(3) 0.0250(4) Uani 1 1 d . . .
C12 C 0.2456(3) 0.32127(11) 1.1318(3) 0.0382(6) Uani 1 1 d . . .
H12 H 0.1416 0.3260 1.1515 0.046 Uiso 1 1 calc R . .
C13 C 0.3797(4) 0.28778(12) 1.2333(3) 0.0446(7) Uani 1 1 d . . .
H13 H 0.3671 0.2697 1.3217 0.054 Uiso 1 1 calc R . .
C14 C 0.5314(3) 0.28070(10) 1.2064(3) 0.0402(6) Uani 1 1 d . . .
H14 H 0.6243 0.2582 1.2771 0.048 Uiso 1 1 calc R . .
C15 C 0.5479(3) 0.30624(10) 1.0769(3) 0.0361(5) Uani 1 1 d . . .
H15 H 0.6517 0.3010 1.0573 0.043 Uiso 1 1 calc R . .
C16 C 0.4128(3) 0.33993(9) 0.9740(3) 0.0303(5) Uani 1 1 d . . .
H16 H 0.4253 0.3574 0.8844 0.036 Uiso 1 1 calc R . .
C17 C -0.2264(3) 0.39397(10) 0.7238(3) 0.0320(5) Uani 1 1 d . . .
H17 H -0.2036 0.4169 0.6427 0.038 Uiso 1 1 calc R . .
C18 C -0.3973(3) 0.36252(11) 0.6301(4) 0.0413(6) Uani 1 1 d . . .
H18A H -0.3820 0.3400 0.5470 0.062 Uiso 1 1 calc R . .
H18B H -0.4964 0.3872 0.5754 0.062 Uiso 1 1 calc R . .
H18C H -0.4232 0.3402 0.7079 0.062 Uiso 1 1 calc R . .
C19 C -0.2488(4) 0.43002(13) 0.8523(4) 0.0513(8) Uani 1 1 d . . .
H19A H -0.2487 0.4084 0.9441 0.077 Uiso 1 1 calc R . .
H19B H -0.3619 0.4493 0.8012 0.077 Uiso 1 1 calc R . .
H19C H -0.1500 0.4555 0.8941 0.077 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
Br1 C8 1.900(2) . ?
O1 C3 1.215(3) . ?
N1 C3 1.378(3) . ?
N1 C5 1.415(3) . ?
N1 C4 1.462(3) . ?
C1 C10 1.510(3) . ?
C1 C11 1.521(3) . ?
C1 C2 1.546(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.522(3) . ?
C2 C17 1.550(3) . ?
C2 H2 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.394(3) . ?
C5 C10 1.399(3) . ?
C6 C7 1.391(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.377(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.391(3) . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C11 C16 1.385(3) . ?
C11 C12 1.392(3) . ?
C12 C13 1.386(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.372(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.397(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.527(4) . ?
C17 C19 1.528(4) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C3 N1 C5 122.11(18) . . ?
C3 N1 C4 118.72(19) . . ?
C5 N1 C4 119.18(18) . . ?
C10 C1 C11 114.16(18) . . ?
C10 C1 C2 107.57(17) . . ?
C11 C1 C2 111.47(18) . . ?
C10 C1 H1 107.8 . . ?
C11 C1 H1 107.8 . . ?
C2 C1 H1 107.8 . . ?
C3 C2 C1 108.80(17) . . ?
C3 C2 C17 110.19(18) . . ?
C1 C2 C17 112.90(18) . . ?
C3 C2 H2 108.3 . . ?
C1 C2 H2 108.3 . . ?
C17 C2 H2 108.3 . . ?
O1 C3 N1 121.8(2) . . ?
O1 C3 C2 122.5(2) . . ?
N1 C3 C2 115.63(18) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 119.9(2) . . ?
C6 C5 N1 120.98(19) . . ?
C10 C5 N1 119.15(19) . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 119.2(2) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 121.2(2) . . ?
C7 C8 Br1 120.32(18) . . ?
C9 C8 Br1 118.50(18) . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C5 119.5(2) . . ?
C9 C10 C1 121.5(2) . . ?
C5 C10 C1 119.05(19) . . ?
C16 C11 C12 118.3(2) . . ?
C16 C11 C1 122.9(2) . . ?
C12 C11 C1 118.8(2) . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.1(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.8(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C11 C16 C15 120.5(2) . . ?
C11 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C19 110.2(2) . . ?
C18 C17 C2 110.7(2) . . ?
C19 C17 C2 111.2(2) . . ?
C18 C17 H17 108.2 . . ?
C19 C17 H17 108.2 . . ?
C2 C17 H17 108.2 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 58.1(2) . . . . ?
C11 C1 C2 C3 -67.8(2) . . . . ?
C10 C1 C2 C17 -64.6(2) . . . . ?
C11 C1 C2 C17 169.55(18) . . . . ?
C5 N1 C3 O1 -175.8(2) . . . . ?
C4 N1 C3 O1 4.3(3) . . . . ?
C5 N1 C3 C2 6.1(3) . . . . ?
C4 N1 C3 C2 -173.8(2) . . . . ?
C1 C2 C3 O1 136.8(2) . . . . ?
C17 C2 C3 O1 -99.0(2) . . . . ?
C1 C2 C3 N1 -45.2(2) . . . . ?
C17 C2 C3 N1 79.1(2) . . . . ?
C3 N1 C5 C6 -162.3(2) . . . . ?
C4 N1 C5 C6 17.6(3) . . . . ?
C3 N1 C5 C10 19.3(3) . . . . ?
C4 N1 C5 C10 -160.7(2) . . . . ?
C10 C5 C6 C7 0.7(3) . . . . ?
N1 C5 C6 C7 -177.7(2) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C9 -0.7(3) . . . . ?
C6 C7 C8 Br1 179.11(17) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
Br1 C8 C9 C10 -178.65(16) . . . . ?
C8 C9 C10 C5 -0.7(3) . . . . ?
C8 C9 C10 C1 179.3(2) . . . . ?
C6 C5 C10 C9 -0.2(3) . . . . ?
N1 C5 C10 C9 178.15(19) . . . . ?
C6 C5 C10 C1 179.80(19) . . . . ?
N1 C5 C10 C1 -1.8(3) . . . . ?
C11 C1 C10 C9 -92.2(2) . . . . ?
C2 C1 C10 C9 143.5(2) . . . . ?
C11 C1 C10 C5 87.7(2) . . . . ?
C2 C1 C10 C5 -36.5(2) . . . . ?
C10 C1 C11 C16 -4.4(3) . . . . ?
C2 C1 C11 C16 117.8(2) . . . . ?
C10 C1 C11 C12 174.4(2) . . . . ?
C2 C1 C11 C12 -63.5(3) . . . . ?
C16 C11 C12 C13 0.9(4) . . . . ?
C1 C11 C12 C13 -177.9(2) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C13 C14 C15 -1.1(4) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C12 C11 C16 C15 -1.1(3) . . . . ?
C1 C11 C16 C15 177.7(2) . . . . ?
C14 C15 C16 C11 0.2(4) . . . . ?
C3 C2 C17 C18 56.3(3) . . . . ?
C1 C2 C17 C18 178.2(2) . . . . ?
C3 C2 C17 C19 179.2(2) . . . . ?
C1 C2 C17 C19 -58.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2018931'
loop_
_audit_author_name
_audit_author_address
'zhang lei'
;Hebei Normal University
China
;
_audit_update_record             
;
2020-07-25 deposited with the CCDC.	2020-09-14 downloaded from the CCDC.
;
_audit_creation_date             2020-07-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H21 N O'
_chemical_formula_sum            'C19 H21 N O'
_chemical_formula_weight         279.37
_chemical_absolute_configuration ?
_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   13.794(11)
_cell_length_b                   14.474(12)
_cell_length_c                   8.318(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1661(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3370
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.60
_cell_measurement_theta_min      2.81
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9641
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.806
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.990
_diffrn_reflns_theta_min         2.039
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_full    0.953
_reflns_Friedel_fraction_max     0.682
_reflns_number_gt                3121
_reflns_number_total             3907
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    ?
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 1124 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3907
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0400
_refine_ls_restrained_S_all      1.052
_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)+(0.0499P)²+0.0745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0955
_refine_ls_wR_factor_ref         0.1055
_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:
 C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C8(H8), C14(H14), C11(H11), C5(H5), C7(H7), C12(H12), C13(H13),
 C6(H6)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.23837(12) 0.11164(12) 0.9817(2) 0.0397(4) Uani 1 1 d . . . . .
C1 C 0.16221(14) 0.04140(13) 1.0537(3) 0.0459(5) Uani 1 1 d . . . . .
O1 O 0.17912(12) -0.02402(10) 1.1463(2) 0.0632(4) Uani 1 1 d . . . . .
C3 C 0.17209(14) 0.18173(14) 0.8950(3) 0.0417(4) Uani 1 1 d . . . . .
C9 C 0.29812(14) 0.05320(13) 0.8562(2) 0.0424(5) Uani 1 1 d . . . . .
C15 C 0.30518(15) 0.15423(14) 1.1158(3) 0.0500(5) Uani 1 1 d . . . . .
H15A H 0.326175 0.104346 1.185420 0.060 Uiso 1 1 calc R . . . .
H15B H 0.362603 0.178822 1.063824 0.060 Uiso 1 1 calc R . . . .
N1 N 0.07122(11) 0.06449(13) 0.9917(3) 0.0548(5) Uani 1 1 d . . . . .
C4 C 0.07508(13) 0.14941(15) 0.9026(3) 0.0477(5) Uani 1 1 d . . . . .
C10 C 0.26899(17) 0.04482(16) 0.6931(3) 0.0560(6) Uani 1 1 d . . . . .
H10 H 0.214934 0.077384 0.657727 0.067 Uiso 1 1 calc R . . . .
C8 C 0.19326(17) 0.26404(14) 0.8127(3) 0.0522(5) Uani 1 1 d . . . . .
H8 H 0.256757 0.285318 0.806441 0.063 Uiso 1 1 calc R . . . .
C14 C 0.38119(15) 0.00250(14) 0.9053(3) 0.0524(5) Uani 1 1 d . . . . .
H14 H 0.402520 0.006317 1.011122 0.063 Uiso 1 1 calc R . . . .
C16 C 0.26160(19) 0.23201(15) 1.2241(3) 0.0604(6) Uani 1 1 d . . . . .
H16 H 0.243735 0.283828 1.154307 0.072 Uiso 1 1 calc R . . . .
C11 C 0.31942(19) -0.01117(18) 0.5839(3) 0.0677(7) Uani 1 1 d . . . . .
H11 H 0.298620 -0.015348 0.477796 0.081 Uiso 1 1 calc R . . . .
C5 C -0.00109(17) 0.19785(19) 0.8275(3) 0.0680(7) Uani 1 1 d . . . . .
H5 H -0.064348 0.175735 0.831204 0.082 Uiso 1 1 calc R . . . .
C7 C 0.1173(2) 0.31426(17) 0.7396(3) 0.0658(7) Uani 1 1 d . . . . .
H7 H 0.130625 0.369453 0.686853 0.079 Uiso 1 1 calc R . . . .
C12 C 0.40189(18) -0.06132(17) 0.6349(4) 0.0657(7) Uani 1 1 d . . . . .
H12 H 0.435532 -0.098662 0.563007 0.079 Uiso 1 1 calc R . . . .
C13 C 0.43192(16) -0.05402(17) 0.7937(4) 0.0635(7) Uani 1 1 d . . . . .
H13 H 0.486218 -0.086716 0.827683 0.076 Uiso 1 1 calc R . . . .
C6 C 0.0213(2) 0.28102(19) 0.7464(4) 0.0740(8) Uani 1 1 d . . . . .
H6 H -0.027979 0.314280 0.696794 0.089 Uiso 1 1 calc R . . . .
C19 C -0.01889(19) 0.0132(2) 1.0300(4) 0.0835(9) Uani 1 1 d . . . . .
H19A H -0.002590 -0.045405 1.076838 0.125 Uiso 1 1 calc GR . . . .
H19B H -0.055420 0.003461 0.933257 0.125 Uiso 1 1 calc GR . . . .
H19C H -0.057004 0.048316 1.104789 0.125 Uiso 1 1 calc GR . . . .
C18 C 0.1699(2) 0.2014(2) 1.3157(4) 0.0781(8) Uani 1 1 d . . . . .
H18A H 0.118098 0.191307 1.240673 0.117 Uiso 1 1 calc GR . . . .
H18B H 0.151474 0.248680 1.390644 0.117 Uiso 1 1 calc GR . . . .
H18C H 0.183058 0.145142 1.372820 0.117 Uiso 1 1 calc GR . . . .
C17 C 0.3415(3) 0.2665(2) 1.3425(4) 0.0943(10) Uani 1 1 d . . . . .
H17A H 0.363051 0.215976 1.408095 0.141 Uiso 1 1 calc GR . . . .
H17B H 0.315334 0.314271 1.409866 0.141 Uiso 1 1 calc GR . . . .
H17C H 0.395270 0.290604 1.282384 0.141 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
C2 C1 1.580(3) . ?
C2 C3 1.545(3) . ?
C2 C9 1.576(3) . ?
C2 C15 1.572(3) . ?
C1 O1 1.243(3) . ?
C1 N1 1.398(3) . ?
C3 C4 1.419(3) . ?
C3 C8 1.405(3) . ?
C9 C10 1.420(3) . ?
C9 C14 1.421(3) . ?
C15 C16 1.562(3) . ?
N1 C4 1.436(3) . ?
N1 C19 1.483(3) . ?
C4 C5 1.409(3) . ?
C10 C11 1.402(3) . ?
C8 C7 1.413(3) . ?
C14 C13 1.421(3) . ?
C16 C18 1.542(4) . ?
C16 C17 1.560(4) . ?
C11 C12 1.414(4) . ?
C5 C6 1.414(4) . ?
C7 C6 1.409(4) . ?
C12 C13 1.388(5) . ?

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 C2 C1 101.89(15) . . ?
C3 C2 C9 110.64(16) . . ?
C3 C2 C15 114.88(16) . . ?
C9 C2 C1 104.68(15) . . ?
C15 C2 C1 111.92(18) . . ?
C15 C2 C9 111.94(15) . . ?
O1 C1 C2 126.90(19) . . ?
O1 C1 N1 125.42(19) . . ?
N1 C1 C2 107.66(17) . . ?
C4 C3 C2 108.72(18) . . ?
C8 C3 C2 131.42(19) . . ?
C8 C3 C4 119.83(19) . . ?
C10 C9 C2 122.05(18) . . ?
C10 C9 C14 117.3(2) . . ?
C14 C9 C2 120.58(18) . . ?
C16 C15 C2 117.78(16) . . ?
C1 N1 C4 111.21(16) . . ?
C1 N1 C19 123.6(2) . . ?
C4 N1 C19 124.8(2) . . ?
C3 C4 N1 109.89(17) . . ?
C5 C4 C3 121.3(2) . . ?
C5 C4 N1 128.8(2) . . ?
C11 C10 C9 121.9(2) . . ?
C3 C8 C7 119.5(2) . . ?
C9 C14 C13 120.5(2) . . ?
C18 C16 C15 113.2(2) . . ?
C18 C16 C17 111.1(2) . . ?
C17 C16 C15 108.8(2) . . ?
C10 C11 C12 120.1(2) . . ?
C4 C5 C6 118.2(2) . . ?
C6 C7 C8 120.2(2) . . ?
C13 C12 C11 119.1(2) . . ?
C12 C13 C14 121.2(2) . . ?
C7 C6 C5 121.0(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
