# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 2303388'
loop_
_audit_author_name
_audit_author_address
'Zhong-Jian Cai'
;College of Chemistry, Chemical Engineering and Materials Science, Soochow University
China
;
_audit_update_record             
;
2023-10-25 deposited with the CCDC.	2023-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H25 N O'
_chemical_formula_sum            'C27 H25 N O'
_chemical_formula_weight         379.48

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   17.256(10)
_cell_length_b                   10.823(6)
_cell_length_c                   11.830(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.45(2)
_cell_angle_gamma                90
_cell_volume                     2149(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5567
_cell_measurement_theta_min      2.4272
_cell_measurement_theta_max      22.9376

_exptl_crystal_description       PRISM
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.173
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.070
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4156
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2014/5 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker ApexII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3928
_diffrn_reflns_av_unetI/netI     0.2239
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.239
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3928
_reflns_number_gt                1761
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1120P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3928
_refine_ls_number_parameters     267
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1924
_refine_ls_R_factor_gt           0.0961
_refine_ls_wR_factor_ref         0.2535
_refine_ls_wR_factor_gt          0.2217
_refine_ls_goodness_of_fit_ref   0.928
_refine_ls_restrained_S_all      0.935
_refine_ls_shift/su_max          0.000
_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_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 0.7272(2) 0.4691(3) 0.4867(3) 0.0430(9) Uani 1 1 d . . . . .
O1 O 0.6922(2) 0.0771(3) 0.3379(3) 0.0763(11) Uani 1 1 d . . . . .
C1 C 0.9357(4) -0.1094(7) 0.8801(6) 0.106(2) Uani 1 1 d . U . . .
H1 H 0.945031 -0.130395 0.958338 0.127 Uiso 1 1 calc R U . . .
C2 C 0.9633(4) -0.1874(5) 0.8039(7) 0.094(2) Uani 1 1 d . . . . .
H2 H 0.988694 -0.260991 0.831313 0.113 Uiso 1 1 calc R U . . .
C3 C 0.9535(3) -0.1569(5) 0.6912(5) 0.0865(18) Uani 1 1 d . . . . .
H3 H 0.973451 -0.207780 0.641286 0.104 Uiso 1 1 calc R U . . .
C4 C 0.9114(3) -0.0433(4) 0.6478(4) 0.0542(12) Uani 1 1 d . . . . .
C5 C 0.9005(3) -0.0091(5) 0.5341(5) 0.0690(15) Uani 1 1 d . . . . .
H5 H 0.922152 -0.056904 0.483795 0.083 Uiso 1 1 calc R U . . .
C6 C 0.8585(3) 0.0937(4) 0.4941(4) 0.0611(13) Uani 1 1 d . . . . .
H6 H 0.852537 0.115970 0.416620 0.073 Uiso 1 1 calc R U . . .
C7 C 0.8234(3) 0.1684(4) 0.5669(4) 0.0446(11) Uani 1 1 d . . . . .
C8 C 0.8362(3) 0.1377(4) 0.6806(4) 0.0528(12) Uani 1 1 d . . . . .
H8 H 0.815190 0.187071 0.730507 0.063 Uiso 1 1 calc R U . . .
C9 C 0.8824(3) 0.0291(4) 0.7261(4) 0.0540(12) Uani 1 1 d . . . . .
C10 C 0.8950(3) -0.0026(5) 0.8421(4) 0.0802(17) Uani 1 1 d . . . . .
H10 H 0.876286 0.047647 0.893703 0.096 Uiso 1 1 calc R U . . .
C11 C 0.7752(3) 0.2769(3) 0.5170(3) 0.0399(11) Uani 1 1 d . . . . .
C12 C 0.7139(3) 0.2819(3) 0.4108(3) 0.0436(11) Uani 1 1 d . . . . .
C13 C 0.6760(3) 0.1876(4) 0.3271(4) 0.0527(12) Uani 1 1 d . . . . .
C14 C 0.6186(3) 0.2347(4) 0.2198(4) 0.0665(14) Uani 1 1 d . . . . .
H14A H 0.583375 0.167686 0.186444 0.080 Uiso 1 1 calc R U . . .
H14B H 0.648676 0.258241 0.163361 0.080 Uiso 1 1 calc R U . . .
C15 C 0.5676(3) 0.3454(4) 0.2396(4) 0.0532(12) Uani 1 1 d . . . . .
C16 C 0.6237(3) 0.4485(4) 0.2962(4) 0.0604(14) Uani 1 1 d . . . . .
H16A H 0.648069 0.485802 0.238414 0.072 Uiso 1 1 calc R U . . .
H16B H 0.593335 0.511869 0.324660 0.072 Uiso 1 1 calc R U . . .
C17 C 0.6879(3) 0.4014(4) 0.3953(3) 0.0439(11) Uani 1 1 d . . . . .
C18 C 0.7823(3) 0.3951(4) 0.5622(3) 0.0409(10) Uani 1 1 d . . . . .
C19 C 0.8389(3) 0.4499(4) 0.6630(4) 0.0593(13) Uani 1 1 d . . . . .
H19A H 0.864488 0.520099 0.637835 0.089 Uiso 1 1 calc R U . . .
H19B H 0.878294 0.389665 0.696713 0.089 Uiso 1 1 calc R U . . .
H19C H 0.810550 0.475728 0.719822 0.089 Uiso 1 1 calc R U . . .
C20 C 0.5176(4) 0.3894(5) 0.1232(5) 0.108(2) Uani 1 1 d . U . . .
H20A H 0.483540 0.455629 0.135659 0.161 Uiso 1 1 calc R U . . .
H20B H 0.485669 0.322220 0.084857 0.161 Uiso 1 1 calc R U . . .
H20C H 0.552068 0.418026 0.075686 0.161 Uiso 1 1 calc R U . . .
C21 C 0.5150(3) 0.3089(6) 0.3187(5) 0.101(2) Uani 1 1 d . . . . .
H21A H 0.547378 0.281490 0.391725 0.151 Uiso 1 1 calc R U . . .
H21B H 0.480288 0.243189 0.283674 0.151 Uiso 1 1 calc R U . . .
H21C H 0.483765 0.378717 0.331356 0.151 Uiso 1 1 calc R U . . .
C22 C 0.7172(3) 0.6012(3) 0.5017(3) 0.0436(11) Uani 1 1 d . . . . .
C23 C 0.6876(3) 0.6418(4) 0.5934(4) 0.0545(13) Uani 1 1 d . . . . .
H23 H 0.673809 0.585798 0.645113 0.065 Uiso 1 1 calc R U . . .
C24 C 0.6786(3) 0.7663(4) 0.6072(4) 0.0613(14) Uani 1 1 d . . . . .
H24 H 0.657984 0.795196 0.668180 0.074 Uiso 1 1 calc R U . . .
C25 C 0.7000(3) 0.8487(4) 0.5315(4) 0.0617(14) Uani 1 1 d . . . . .
H25 H 0.694831 0.933098 0.542311 0.074 Uiso 1 1 calc R U . . .
C26 C 0.7288(3) 0.8070(4) 0.4409(4) 0.0596(13) Uani 1 1 d . . . . .
H26 H 0.742239 0.863329 0.389295 0.071 Uiso 1 1 calc R U . . .
C27 C 0.7383(3) 0.6819(4) 0.4245(4) 0.0518(12) Uani 1 1 d . . . . .
H27 H 0.758353 0.653244 0.362893 0.062 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C17 1.351(5) . ?
N1 C18 1.396(5) . ?
N1 C22 1.455(5) . ?
O1 C13 1.227(5) . ?
C1 C10 1.372(7) . ?
C1 C2 1.397(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.346(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.459(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(6) . ?
C4 C9 1.392(6) . ?
C5 C6 1.352(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.416(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.354(6) . ?
C7 C11 1.480(5) . ?
C8 C9 1.452(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.382(6) . ?
C10 H10 0.9300 . ?
C11 C18 1.381(5) . ?
C11 C12 1.443(6) . ?
C12 C17 1.367(5) . ?
C12 C13 1.466(6) . ?
C13 C14 1.505(6) . ?
C14 C15 1.537(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C21 1.499(6) . ?
C15 C20 1.521(7) . ?
C15 C16 1.527(6) . ?
C16 C17 1.502(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C18 C19 1.478(6) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C27 1.373(5) . ?
C22 C23 1.374(5) . ?
C23 C24 1.371(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.373(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.358(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.383(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?

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 N1 C18 109.9(3) . . ?
C17 N1 C22 125.4(3) . . ?
C18 N1 C22 124.6(3) . . ?
C10 C1 C2 121.5(6) . . ?
C10 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 120.5(6) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 119.5(6) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C9 121.0(4) . . ?
C5 C4 C3 121.2(5) . . ?
C9 C4 C3 117.8(5) . . ?
C6 C5 C4 120.5(5) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 121.8(4) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 118.0(4) . . ?
C8 C7 C11 122.6(4) . . ?
C6 C7 C11 119.4(4) . . ?
C7 C8 C9 121.1(4) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C10 C9 C4 121.5(5) . . ?
C10 C9 C8 121.0(5) . . ?
C4 C9 C8 117.4(4) . . ?
C1 C10 C9 119.0(6) . . ?
C1 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C18 C11 C12 106.5(3) . . ?
C18 C11 C7 126.1(4) . . ?
C12 C11 C7 127.4(3) . . ?
C17 C12 C11 107.6(3) . . ?
C17 C12 C13 119.2(4) . . ?
C11 C12 C13 133.1(4) . . ?
O1 C13 C12 123.6(4) . . ?
O1 C13 C14 120.5(4) . . ?
C12 C13 C14 115.8(4) . . ?
C13 C14 C15 115.1(4) . . ?
C13 C14 H14A 108.5 . . ?
C15 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
C15 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C21 C15 C20 110.5(5) . . ?
C21 C15 C16 109.5(4) . . ?
C20 C15 C16 109.7(4) . . ?
C21 C15 C14 109.9(4) . . ?
C20 C15 C14 109.3(4) . . ?
C16 C15 C14 108.0(4) . . ?
C17 C16 C15 111.8(3) . . ?
C17 C16 H16A 109.2 . . ?
C15 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C15 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
N1 C17 C12 108.6(3) . . ?
N1 C17 C16 125.6(4) . . ?
C12 C17 C16 125.8(4) . . ?
C11 C18 N1 107.3(4) . . ?
C11 C18 C19 131.8(4) . . ?
N1 C18 C19 120.6(4) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C15 C21 H21A 109.5 . . ?
C15 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C15 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 121.8(4) . . ?
C27 C22 N1 119.1(3) . . ?
C23 C22 N1 119.1(3) . . ?
C24 C23 C22 118.8(4) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C25 120.4(4) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C24 120.1(4) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 120.8(4) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C22 C27 C26 118.1(4) . . ?
C22 C27 H27 120.9 . . ?
C26 C27 H27 120.9 . . ?

_refine_diff_density_max         0.396
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.090



####################################################################### 
# 
# 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_b221025b_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2303389'
loop_
_audit_author_name
_audit_author_address
'Zhong-Jian Cai'
;College of Chemistry, Chemical Engineering and Materials Science, Soochow University
China
;
_audit_update_record             
;
2023-10-25 deposited with the CCDC.	2023-12-14 downloaded from the CCDC.
;
_audit_creation_date             2023-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C27 H25 N O)'
_chemical_formula_sum            'C13.50 H12.50 N0.50 O0.50'
_chemical_formula_weight         189.74
_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                   8.8172(5)
_cell_length_b                   11.7300(8)
_cell_length_c                   20.8491(13)
_cell_angle_alpha                90
_cell_angle_beta                 100.642(2)
_cell_angle_gamma                90
_cell_volume                     2119.2(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4194
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1625 before and 0.1049 after correction.
The Ratio of minimum to maximum transmission is 0.5625.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.189
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1052
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            56357
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.601
_diffrn_reflns_theta_min         2.350
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3131
_reflns_number_total             4909
_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    ?
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         4909
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0555
_refine_ls_restrained_S_all      1.035
_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)+(0.0594P)²+0.4692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1437
_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:
 C5(H5A,H5B), C7(H7A,H7B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C19(H19), C26(H26), C27(H27), C24(H24), C16(H16), C21(H21), C23(H23),
 C12(H12), C22(H22), C15(H15), C13(H13), C14(H14)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.68162(15) 0.37050(12) 0.42211(6) 0.0562(4) Uani 1 1 d . . . . .
N1 N 0.47397(14) 0.30589(11) 0.60397(6) 0.0359(3) Uani 1 1 d . . . . .
C1 C 0.40238(18) 0.23300(13) 0.55433(8) 0.0365(4) Uani 1 1 d . . . . .
C2 C 0.46537(18) 0.25299(13) 0.50104(8) 0.0365(4) Uani 1 1 d . . . . .
H2 H 0.4395 0.2163 0.4610 0.044 Uiso 1 1 calc R . . . .
C8 C 0.58020(17) 0.37159(13) 0.58080(7) 0.0345(4) Uani 1 1 d . . . . .
C3 C 0.57852(17) 0.34035(13) 0.51716(7) 0.0340(4) Uani 1 1 d . . . . .
C4 C 0.67843(17) 0.39503(14) 0.47910(8) 0.0365(4) Uani 1 1 d . . . . .
C5 C 0.77836(18) 0.48904(14) 0.51334(8) 0.0386(4) Uani 1 1 d . . . . .
H5A H 0.7237 0.5606 0.5040 0.046 Uiso 1 1 calc R . . . .
H5B H 0.8713 0.4935 0.4948 0.046 Uiso 1 1 calc R . . . .
C11 C 0.44062(18) 0.31143(15) 0.66896(7) 0.0399(4) Uani 1 1 d . . . . .
C18 C 0.20384(19) 0.09453(14) 0.50288(8) 0.0419(4) Uani 1 1 d . . . . .
C6 C 0.82625(18) 0.47735(14) 0.58783(8) 0.0390(4) Uani 1 1 d . . . . .
C19 C 0.0701(2) 0.13251(14) 0.46556(9) 0.0440(4) Uani 1 1 d . . . . .
H19 H 0.0214 0.1960 0.4792 0.053 Uiso 1 1 calc R . . . .
C20 C 0.00323(19) 0.07755(14) 0.40643(8) 0.0428(4) Uani 1 1 d . . . . .
C7 C 0.68011(19) 0.46030(15) 0.61757(8) 0.0424(4) Uani 1 1 d . . . . .
H7A H 0.7093 0.4375 0.6629 0.051 Uiso 1 1 calc R . . . .
H7B H 0.6237 0.5316 0.6160 0.051 Uiso 1 1 calc R . . . .
C17 C 0.2762(2) 0.15352(16) 0.56515(8) 0.0495(5) Uani 1 1 d . . . . .
H17A H 0.1978 0.1962 0.5819 0.059 Uiso 1 1 calc R . . . .
H17B H 0.3182 0.0969 0.5975 0.059 Uiso 1 1 calc R . . . .
C25 C 0.0789(2) -0.01798(14) 0.38585(8) 0.0430(4) Uani 1 1 d . . . . .
C26 C 0.2171(2) -0.05582(15) 0.42505(10) 0.0504(5) Uani 1 1 d . . . . .
H26 H 0.2683 -0.1187 0.4121 0.060 Uiso 1 1 calc R . . . .
C27 C 0.2762(2) -0.00140(15) 0.48150(10) 0.0504(5) Uani 1 1 d . . . . .
H27 H 0.3672 -0.0283 0.5068 0.061 Uiso 1 1 calc R . . . .
C24 C 0.0080(2) -0.07500(17) 0.32780(9) 0.0551(5) Uani 1 1 d . . . . .
H24 H 0.0558 -0.1382 0.3134 0.066 Uiso 1 1 calc R . . . .
C16 C 0.3543(2) 0.40023(18) 0.68544(9) 0.0547(5) Uani 1 1 d . . . . .
H16 H 0.3188 0.4569 0.6552 0.066 Uiso 1 1 calc R . . . .
C21 C -0.1375(2) 0.11492(18) 0.36851(10) 0.0592(5) Uani 1 1 d . . . . .
H21 H -0.1868 0.1789 0.3812 0.071 Uiso 1 1 calc R . . . .
C9 C 0.9346(2) 0.37605(17) 0.60428(10) 0.0575(5) Uani 1 1 d . . . . .
H9A H 0.8832 0.3077 0.5867 0.086 Uiso 1 1 calc GR . . . .
H9B H 0.9636 0.3690 0.6508 0.086 Uiso 1 1 calc GR . . . .
H9C H 1.0253 0.3876 0.5857 0.086 Uiso 1 1 calc GR . . . .
C10 C 0.9092(2) 0.58615(17) 0.61538(10) 0.0581(5) Uani 1 1 d . . . . .
H10A H 0.9967 0.5991 0.5950 0.087 Uiso 1 1 calc GR . . . .
H10B H 0.9432 0.5780 0.6616 0.087 Uiso 1 1 calc GR . . . .
H10C H 0.8396 0.6496 0.6069 0.087 Uiso 1 1 calc GR . . . .
C23 C -0.1283(3) -0.0382(2) 0.29330(10) 0.0649(6) Uani 1 1 d . . . . .
H23 H -0.1739 -0.0770 0.2558 0.078 Uiso 1 1 calc R . . . .
C12 C 0.4963(3) 0.22843(19) 0.71353(10) 0.0643(6) Uani 1 1 d . . . . .
H12 H 0.5550 0.1685 0.7020 0.077 Uiso 1 1 calc R . . . .
C22 C -0.2011(3) 0.0571(2) 0.31340(10) 0.0688(6) Uani 1 1 d . . . . .
H22 H -0.2943 0.0817 0.2889 0.083 Uiso 1 1 calc R . . . .
C15 C 0.3205(3) 0.4047(2) 0.74765(11) 0.0788(7) Uani 1 1 d . . . . .
H15 H 0.2600 0.4637 0.7589 0.095 Uiso 1 1 calc R . . . .
C13 C 0.4635(3) 0.2354(3) 0.77634(11) 0.0885(9) Uani 1 1 d . . . . .
H13 H 0.5016 0.1805 0.8073 0.106 Uiso 1 1 calc R . . . .
C14 C 0.3750(3) 0.3235(3) 0.79244(11) 0.0914(9) Uani 1 1 d . . . . .
H14 H 0.3523 0.3276 0.8342 0.110 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
O1 C4 1.2279(19) . ?
N1 C1 1.400(2) . ?
N1 C8 1.3681(19) . ?
N1 C11 1.440(2) . ?
C1 C2 1.351(2) . ?
C1 C17 1.500(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.426(2) . ?
C8 C3 1.374(2) . ?
C8 C7 1.482(2) . ?
C3 C4 1.441(2) . ?
C4 C5 1.506(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.539(2) . ?
C11 C16 1.371(3) . ?
C11 C12 1.373(3) . ?
C18 C19 1.362(2) . ?
C18 C17 1.505(2) . ?
C18 C27 1.406(2) . ?
C6 C7 1.543(2) . ?
C6 C9 1.524(3) . ?
C6 C10 1.529(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.419(2) . ?
C20 C25 1.411(2) . ?
C20 C21 1.412(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C25 C26 1.408(2) . ?
C25 C24 1.423(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.356(3) . ?
C27 H27 0.9300 . ?
C24 H24 0.9300 . ?
C24 C23 1.352(3) . ?
C16 H16 0.9300 . ?
C16 C15 1.384(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.362(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C23 H23 0.9300 . ?
C23 C22 1.391(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.395(3) . ?
C22 H22 0.9300 . ?
C15 H15 0.9300 . ?
C15 C14 1.358(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.373(4) . ?
C14 H14 0.9300 . ?

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 C11 125.50(13) . . ?
C8 N1 C1 109.13(13) . . ?
C8 N1 C11 125.37(13) . . ?
N1 C1 C17 120.94(14) . . ?
C2 C1 N1 107.71(13) . . ?
C2 C1 C17 131.32(15) . . ?
C1 C2 H2 126.1 . . ?
C1 C2 C3 107.87(14) . . ?
C3 C2 H2 126.1 . . ?
N1 C8 C3 107.74(13) . . ?
N1 C8 C7 126.38(14) . . ?
C3 C8 C7 125.88(14) . . ?
C2 C3 C4 131.49(14) . . ?
C8 C3 C2 107.54(13) . . ?
C8 C3 C4 120.96(14) . . ?
O1 C4 C3 123.66(15) . . ?
O1 C4 C5 120.94(15) . . ?
C3 C4 C5 115.38(14) . . ?
C4 C5 H5A 108.3 . . ?
C4 C5 H5B 108.3 . . ?
C4 C5 C6 116.14(13) . . ?
H5A C5 H5B 107.4 . . ?
C6 C5 H5A 108.3 . . ?
C6 C5 H5B 108.3 . . ?
C16 C11 N1 119.30(15) . . ?
C16 C11 C12 121.01(18) . . ?
C12 C11 N1 119.69(17) . . ?
C19 C18 C17 121.78(16) . . ?
C19 C18 C27 118.45(16) . . ?
C27 C18 C17 119.76(16) . . ?
C5 C6 C7 108.86(13) . . ?
C9 C6 C5 109.90(14) . . ?
C9 C6 C7 110.13(14) . . ?
C9 C6 C10 109.27(14) . . ?
C10 C6 C5 109.14(14) . . ?
C10 C6 C7 109.52(14) . . ?
C18 C19 H19 119.2 . . ?
C18 C19 C20 121.62(16) . . ?
C20 C19 H19 119.2 . . ?
C25 C20 C19 118.75(16) . . ?
C25 C20 C21 119.49(17) . . ?
C21 C20 C19 121.76(17) . . ?
C8 C7 C6 110.12(13) . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.2 . . ?
C1 C17 C18 111.36(14) . . ?
C1 C17 H17A 109.4 . . ?
C1 C17 H17B 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C20 C25 C24 118.27(17) . . ?
C26 C25 C20 118.76(16) . . ?
C26 C25 C24 122.90(17) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.55(17) . . ?
C27 C26 H26 119.7 . . ?
C18 C27 H27 119.1 . . ?
C26 C27 C18 121.86(17) . . ?
C26 C27 H27 119.1 . . ?
C25 C24 H24 119.7 . . ?
C23 C24 C25 120.7(2) . . ?
C23 C24 H24 119.7 . . ?
C11 C16 H16 120.4 . . ?
C11 C16 C15 119.3(2) . . ?
C15 C16 H16 120.4 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C24 C23 H23 119.7 . . ?
C24 C23 C22 120.7(2) . . ?
C22 C23 H23 119.7 . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 118.9(2) . . ?
C13 C12 H12 120.5 . . ?
C21 C22 C23 120.9(2) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C16 C15 H15 119.7 . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.7 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.0(2) . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 120.3(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
