# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_22020929s4s4_0m
_audit_block_doi                 10.5517/ccdc.csd.cc27zgxm
_database_code_depnum_ccdc_archive 'CCDC 2084871'
loop_
_audit_author_name
_audit_author_address
ZhangCun
;Xinjiang Technical Institute of Physics and Chemistry, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2021-05-20 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_audit_creation_date             2020-11-23
_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         'C15 H26 O2'
_chemical_formula_sum            'C15 H26 O2'
_chemical_formula_weight         238.36
_chemical_absolute_configuration rmad
_chemical_melting_point          313.65
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   6.2068(2)
_cell_length_b                   9.6747(3)
_cell_length_c                   23.6894(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1422.52(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9877
_cell_measurement_temperature    160
_cell_measurement_theta_max      72.496
_cell_measurement_theta_min      3.732
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.921
_exptl_absorpt_coefficient_mu    0.555
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1633 before and 0.0619 after correction. The Ratio of minimum to maximum transmission is 0.8367. 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    1.113
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11340
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.476
_diffrn_reflns_theta_min         3.732
_diffrn_ambient_temperature      160.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.695
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2656
_reflns_number_total             2771
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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         0.158
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 
;
 Flack x determined using 1053 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0310
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0311P)²+0.2177P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0750
_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:
 C6(H6), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C7(H7B,H7A), C2(H2A,H2B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C),
 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
O1 O 0.53097(19) 0.24896(11) 0.36162(4) 0.0312(3) Uani 1 1 d . . . . .
O2 O 0.4576(2) 0.16374(13) 0.44879(5) 0.0403(3) Uani 1 1 d . . . . .
C1 C 0.4902(3) 0.52508(17) 0.31331(7) 0.0293(4) Uani 1 1 d . . . . .
H1A H 0.647766 0.537999 0.317194 0.035 Uiso 1 1 calc R . . . .
H1B H 0.466323 0.448674 0.286231 0.035 Uiso 1 1 calc R . . . .
C5 C 0.1661(3) 0.68942(16) 0.40096(7) 0.0277(3) Uani 1 1 d . . . . .
C6 C 0.3979(2) 0.48276(15) 0.37080(6) 0.0232(3) Uani 1 1 d . . . . .
H6 H 0.250339 0.445197 0.363671 0.028 Uiso 1 1 calc R . . . .
C7 C 0.3712(3) 0.60734(16) 0.41059(6) 0.0273(3) Uani 1 1 d . . . . .
H7B H 0.372692 0.573825 0.450074 0.033 Uiso 1 1 calc R . . . .
H7A H 0.496266 0.669715 0.405696 0.033 Uiso 1 1 calc R . . . .
C2 C 0.3928(3) 0.65727(17) 0.28889(7) 0.0294(4) Uani 1 1 d . . . . .
H2A H 0.434464 0.664116 0.248644 0.035 Uiso 1 1 calc R . . . .
H2B H 0.456675 0.737442 0.308756 0.035 Uiso 1 1 calc R . . . .
C4 C 0.0706(3) 0.70796(16) 0.35131(7) 0.0289(3) Uani 1 1 d . . . . .
H4 H -0.065247 0.753141 0.352661 0.035 Uiso 1 1 calc R . . . .
C10 C 0.5277(3) 0.36692(16) 0.39921(6) 0.0259(3) Uani 1 1 d . . . . .
C12 C 0.4133(3) 0.30790(17) 0.45134(7) 0.0351(4) Uani 1 1 d . . . . .
H12A H 0.471633 0.348906 0.486444 0.042 Uiso 1 1 calc R . . . .
H12B H 0.256344 0.325600 0.449619 0.042 Uiso 1 1 calc R . . . .
C3 C 0.1469(3) 0.66752(17) 0.29304(7) 0.0294(4) Uani 1 1 d . . . . .
H3 H 0.084022 0.575313 0.283438 0.035 Uiso 1 1 calc R . . . .
C13 C 0.4570(3) 0.12882(17) 0.39048(7) 0.0326(4) Uani 1 1 d . . . . .
C11 C 0.7594(3) 0.40506(19) 0.41278(8) 0.0365(4) Uani 1 1 d . . . . .
H11A H 0.827587 0.329220 0.433584 0.055 Uiso 1 1 calc GR . . . .
H11B H 0.761693 0.489040 0.435903 0.055 Uiso 1 1 calc GR . . . .
H11C H 0.838424 0.421531 0.377599 0.055 Uiso 1 1 calc GR . . . .
C14 C 0.6152(4) 0.01180(19) 0.38176(9) 0.0464(5) Uani 1 1 d . . . . .
H14A H 0.629990 -0.006980 0.341292 0.070 Uiso 1 1 calc GR . . . .
H14B H 0.562304 -0.071278 0.400955 0.070 Uiso 1 1 calc GR . . . .
H14C H 0.755612 0.037832 0.397376 0.070 Uiso 1 1 calc GR . . . .
C8 C 0.0691(3) 0.7490(2) 0.45382(7) 0.0418(4) Uani 1 1 d . . . . .
H8A H 0.042171 0.674513 0.480972 0.063 Uiso 1 1 calc GR . . . .
H8B H -0.067098 0.794963 0.444582 0.063 Uiso 1 1 calc GR . . . .
H8C H 0.168967 0.816167 0.470334 0.063 Uiso 1 1 calc GR . . . .
C9 C 0.0621(3) 0.7741(2) 0.25055(7) 0.0430(4) Uani 1 1 d . . . . .
H9A H 0.121481 0.865325 0.259561 0.065 Uiso 1 1 calc GR . . . .
H9B H -0.095483 0.777600 0.252587 0.065 Uiso 1 1 calc GR . . . .
H9C H 0.106200 0.747433 0.212344 0.065 Uiso 1 1 calc GR . . . .
C15 C 0.2322(3) 0.0932(2) 0.37018(10) 0.0525(6) Uani 1 1 d . . . . .
H15A H 0.134180 0.169730 0.378866 0.079 Uiso 1 1 calc GR . . . .
H15B H 0.182286 0.009216 0.389236 0.079 Uiso 1 1 calc GR . . . .
H15C H 0.234774 0.077708 0.329302 0.079 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 C10 1.4476(18) . ?
O1 C13 1.4244(19) . ?
O2 C12 1.423(2) . ?
O2 C13 1.422(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C6 1.533(2) . ?
C1 C2 1.528(2) . ?
C5 C7 1.518(2) . ?
C5 C4 1.329(2) . ?
C5 C8 1.504(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.539(2) . ?
C6 C10 1.535(2) . ?
C7 H7B 0.9900 . ?
C7 H7A 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.533(2) . ?
C4 H4 0.9500 . ?
C4 C3 1.511(2) . ?
C10 C12 1.535(2) . ?
C10 C11 1.519(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C3 H3 1.0000 . ?
C3 C9 1.534(2) . ?
C13 C14 1.513(2) . ?
C13 C15 1.516(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
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
C13 O1 C10 110.10(12) . . ?
C13 O2 C12 105.88(12) . . ?
H1A C1 H1B 107.6 . . ?
C6 C1 H1A 108.7 . . ?
C6 C1 H1B 108.7 . . ?
C2 C1 H1A 108.7 . . ?
C2 C1 H1B 108.7 . . ?
C2 C1 C6 114.33(13) . . ?
C4 C5 C7 125.30(14) . . ?
C4 C5 C8 120.42(15) . . ?
C8 C5 C7 114.26(14) . . ?
C1 C6 H6 106.8 . . ?
C1 C6 C7 112.03(12) . . ?
C1 C6 C10 112.85(12) . . ?
C7 C6 H6 106.8 . . ?
C10 C6 H6 106.8 . . ?
C10 C6 C7 111.09(12) . . ?
C5 C7 C6 114.08(13) . . ?
C5 C7 H7B 108.7 . . ?
C5 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C6 C7 H7A 108.7 . . ?
H7B C7 H7A 107.6 . . ?
C1 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C1 C2 C3 115.07(14) . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C5 C4 H4 115.3 . . ?
C5 C4 C3 129.30(15) . . ?
C3 C4 H4 115.3 . . ?
O1 C10 C6 108.26(12) . . ?
O1 C10 C12 102.02(12) . . ?
O1 C10 C11 107.95(12) . . ?
C12 C10 C6 112.44(13) . . ?
C11 C10 C6 114.33(13) . . ?
C11 C10 C12 110.98(14) . . ?
O2 C12 C10 103.96(13) . . ?
O2 C12 H12A 111.0 . . ?
O2 C12 H12B 111.0 . . ?
C10 C12 H12A 111.0 . . ?
C10 C12 H12B 111.0 . . ?
H12A C12 H12B 109.0 . . ?
C2 C3 H3 108.4 . . ?
C2 C3 C9 110.06(14) . . ?
C4 C3 C2 112.81(13) . . ?
C4 C3 H3 108.4 . . ?
C4 C3 C9 108.53(14) . . ?
C9 C3 H3 108.4 . . ?
O1 C13 C14 109.65(14) . . ?
O1 C13 C15 109.26(15) . . ?
O2 C13 O1 105.75(13) . . ?
O2 C13 C14 108.00(15) . . ?
O2 C13 C15 111.37(16) . . ?
C14 C13 C15 112.58(16) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C9 H9A 109.5 . . ?
C3 C9 H9B 109.5 . . ?
C3 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: PE'
_chemical_compound_source        synthetic
####################################################################### 
# 
# 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_cu_220201016_0m
_audit_block_doi                 10.5517/ccdc.csd.cc27zgyn
_database_code_depnum_ccdc_archive 'CCDC 2084872'
loop_
_audit_author_name
_audit_author_address
'zhang cun'
;UCAS
China
;
_audit_update_record             
;
2021-05-20 deposited with the CCDC.	2021-07-28 downloaded from the CCDC.
;
_audit_creation_date             2020-12-07
_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            'Rupestine D'
_chemical_name_systematic        'Rupestine D'
_chemical_formula_moiety         'C14 H19 N O'
_chemical_formula_sum            'C14 H19 N O'
_chemical_formula_weight         217.30
_chemical_absolute_configuration rmad
_chemical_melting_point          378.65
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   4.9824(2)
_cell_length_b                   11.7685(5)
_cell_length_c                   10.6674(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.617(2)
_cell_angle_gamma                90
_cell_volume                     612.67(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9545
_cell_measurement_temperature    150
_cell_measurement_theta_max      74.293
_cell_measurement_theta_min      3.756
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.571
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.5850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1584 before and 0.0844 after correction. The Ratio of minimum to maximum transmission is 0.7761. 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    1.178
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10051
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.216
_diffrn_reflns_theta_min         4.231
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2137
_reflns_number_total             2194
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 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         0.152
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 942 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2194
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.073
_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)+(0.0536P)²+0.0997P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1025
_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:
 C11(H11), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C6(H6A,H6B,H6C), C14(H14A,H14B,H14C)
;
_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 0.1109(4) 0.44814(19) 0.29700(17) 0.0490(5) Uani 1 1 d . . . . .
N1 N 0.6992(4) 0.37563(17) 0.72587(18) 0.0319(4) Uani 1 1 d . . . . .
C5 C 0.5022(4) 0.4548(2) 0.6963(2) 0.0291(5) Uani 1 1 d . . . . .
C1 C 0.4590(5) 0.54143(19) 0.7807(2) 0.0295(5) Uani 1 1 d . . . . .
C4 C 0.8634(5) 0.3772(2) 0.8429(2) 0.0343(5) Uani 1 1 d . . . . .
C11 C 0.2450(5) 0.6326(2) 0.7398(2) 0.0326(5) Uani 1 1 d . . . . .
H11 H 0.065725 0.593708 0.708043 0.039 Uiso 1 1 calc R . . . .
C7 C 0.3296(5) 0.4452(2) 0.5635(2) 0.0321(5) Uani 1 1 d . . . . .
H7A H 0.133504 0.446450 0.568701 0.039 Uiso 1 1 calc R . . . .
H7B H 0.367553 0.371597 0.525637 0.039 Uiso 1 1 calc R . . . .
C13 C 0.3042(5) 0.5105(2) 0.3355(2) 0.0357(6) Uani 1 1 d . . . . .
C2 C 0.6263(5) 0.5384(2) 0.9022(2) 0.0336(5) Uani 1 1 d . . . . .
H2 H 0.602078 0.593513 0.964108 0.040 Uiso 1 1 calc R . . . .
C8 C 0.3868(5) 0.5425(2) 0.4758(2) 0.0320(5) Uani 1 1 d . . . . .
H8 H 0.587957 0.558610 0.495338 0.038 Uiso 1 1 calc R . . . .
C3 C 0.8273(5) 0.4562(2) 0.9341(2) 0.0366(5) Uani 1 1 d . . . . .
H3 H 0.938926 0.454080 1.017492 0.044 Uiso 1 1 calc R . . . .
C9 C 0.2343(5) 0.6523(2) 0.4955(2) 0.0354(5) Uani 1 1 d . . . . .
H9A H 0.269492 0.709089 0.432223 0.043 Uiso 1 1 calc R . . . .
H9B H 0.035164 0.636190 0.476689 0.043 Uiso 1 1 calc R . . . .
C12 C 0.2096(6) 0.7112(2) 0.8494(3) 0.0430(6) Uani 1 1 d . . . . .
H12A H 0.178481 0.665562 0.922013 0.065 Uiso 1 1 calc GR . . . .
H12B H 0.052231 0.761368 0.820704 0.065 Uiso 1 1 calc GR . . . .
H12C H 0.375477 0.757126 0.875893 0.065 Uiso 1 1 calc GR . . . .
C10 C 0.3096(5) 0.7052(2) 0.6287(2) 0.0351(5) Uani 1 1 d . . . . .
H10A H 0.211511 0.778496 0.627387 0.042 Uiso 1 1 calc R . . . .
H10B H 0.508318 0.722106 0.646992 0.042 Uiso 1 1 calc R . . . .
C6 C 1.0856(5) 0.2890(2) 0.8681(3) 0.0416(6) Uani 1 1 d . . . . .
H6A H 1.003420 0.213119 0.856886 0.062 Uiso 1 1 calc GR . . . .
H6B H 1.189635 0.297137 0.955990 0.062 Uiso 1 1 calc GR . . . .
H6C H 1.208645 0.299327 0.808029 0.062 Uiso 1 1 calc GR . . . .
C14 C 0.4680(6) 0.5619(3) 0.2470(3) 0.0494(7) Uani 1 1 d . . . . .
H14A H 0.647857 0.525044 0.259725 0.074 Uiso 1 1 calc GR . . . .
H14B H 0.492002 0.643332 0.264876 0.074 Uiso 1 1 calc GR . . . .
H14C H 0.371524 0.550987 0.158207 0.074 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 C13 1.214(3) . ?
N1 C5 1.344(3) . ?
N1 C4 1.348(3) . ?
C5 C1 1.405(3) . ?
C5 C7 1.506(3) . ?
C1 C11 1.513(3) . ?
C1 C2 1.394(3) . ?
C4 C3 1.383(4) . ?
C4 C6 1.501(3) . ?
C11 H11 1.0000 . ?
C11 C12 1.530(3) . ?
C11 C10 1.547(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.541(3) . ?
C13 C8 1.517(3) . ?
C13 C14 1.494(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.535(4) . ?
C3 H3 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.528(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C5 N1 C4 119.1(2) . . ?
N1 C5 C1 123.5(2) . . ?
N1 C5 C7 114.90(19) . . ?
C1 C5 C7 121.6(2) . . ?
C5 C1 C11 121.3(2) . . ?
C2 C1 C5 116.0(2) . . ?
C2 C1 C11 122.7(2) . . ?
N1 C4 C3 121.3(2) . . ?
N1 C4 C6 116.4(2) . . ?
C3 C4 C6 122.3(2) . . ?
C1 C11 H11 107.6 . . ?
C1 C11 C12 113.1(2) . . ?
C1 C11 C10 111.67(19) . . ?
C12 C11 H11 107.6 . . ?
C12 C11 C10 109.0(2) . . ?
C10 C11 H11 107.6 . . ?
C5 C7 H7A 109.2 . . ?
C5 C7 H7B 109.2 . . ?
C5 C7 C8 112.06(19) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
O1 C13 C8 121.5(2) . . ?
O1 C13 C14 121.9(2) . . ?
C14 C13 C8 116.7(2) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.9(2) . . ?
C3 C2 H2 119.6 . . ?
C7 C8 H8 108.3 . . ?
C13 C8 C7 111.6(2) . . ?
C13 C8 H8 108.3 . . ?
C13 C8 C9 107.5(2) . . ?
C9 C8 C7 112.65(18) . . ?
C9 C8 H8 108.3 . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C8 C9 H9A 108.3 . . ?
C8 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
C10 C9 C8 115.8(2) . . ?
C10 C9 H9A 108.3 . . ?
C10 C9 H9B 108.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C9 C10 C11 115.94(19) . . ?
C9 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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