# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_zs1_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc2974b1
_database_code_depnum_ccdc_archive 'CCDC 2122022'
loop_
_audit_author_name
_audit_author_address
'Sheng Zhang'
;Anhui University
China
;
_audit_update_record             
;
2021-11-15 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;
_audit_creation_date             2020-12-29
_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        
4-((1R,2S,5S)-2,6,6-trimethyl-4-oxobicyclo[3.1.1]heptan-2-yl)benzonitrile
_chemical_formula_moiety         'C17 H19 N O'
_chemical_formula_sum            'C17 H19 N O'
_chemical_formula_weight         253.33
_chemical_absolute_configuration ad
_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      trigonal
_space_group_IT_number           152
_space_group_name_H-M_alt        'P 31 2 1'
_space_group_name_Hall           'P 31 2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'y, x, -z'
'x-y, -y, -z+2/3'
'-x, -x+y, -z+1/3'

_cell_length_a                   10.9010(19)
_cell_length_b                   10.9010(19)
_cell_length_c                   20.449(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2104.4(9)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9383
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      55.014
_cell_measurement_theta_min      4.074
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6445
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1688 before and 0.0861 after correction. The Ratio of minimum to maximum transmission is 0.8584. 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    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            44884
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.095
_diffrn_reflns_theta_min         4.074
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_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         0.720
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                2590
_reflns_number_total             2673
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 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    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1071 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.15(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2673
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      0.997
_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)+(0.0822P)²+0.1936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1087
_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:
 C005(H005), C00D(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C008(H00A,H00B), C00G(H00K,H00L)
2.c Aromatic/amide H refined with riding coordinates:
 C001(H001), C006(H006), C007(H007), C00A(H00C)
2.d Idealised Me refined as rotating group:
 C00E(H00E,H00F,H00G), C00F(H00H,H00I,H00J), C00J(H00M,H00N,H00O)
;
_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
C001 C 0.03942(19) 0.27843(19) 0.76009(8) 0.0360(4) Uani 1 1 d . . . . .
H001 H 0.007068 0.344194 0.765293 0.043 Uiso 1 1 calc R . . . .
C002 C 0.18483(18) 0.32836(19) 0.75721(8) 0.0336(4) Uani 1 1 d . . . . .
O003 O 0.4945(3) 0.6808(2) 0.61593(9) 0.0909(8) Uani 1 1 d . . . . .
C004 C 0.29831(17) 0.48505(18) 0.76550(8) 0.0339(4) Uani 1 1 d . . . . .
C005 C 0.23409(17) 0.58200(18) 0.76438(8) 0.0339(4) Uani 1 1 d . . . . .
H005 H 0.162794 0.561382 0.799644 0.041 Uiso 1 1 calc R . . . .
C006 C -0.0590(2) 0.1350(2) 0.75554(9) 0.0406(4) Uani 1 1 d . . . . .
H006 H -0.157433 0.103690 0.756726 0.049 Uiso 1 1 calc R . . . .
C007 C 0.2273(2) 0.2273(2) 0.75072(8) 0.0422(4) Uani 1 1 d . . . . .
H007 H 0.325605 0.258107 0.748821 0.051 Uiso 1 1 calc R . . . .
C008 C 0.1793(2) 0.5829(2) 0.69474(10) 0.0467(5) Uani 1 1 d . . . . .
H00A H 0.102791 0.606795 0.693212 0.056 Uiso 1 1 calc R . . . .
H00B H 0.154295 0.496807 0.668861 0.056 Uiso 1 1 calc R . . . .
N009 N -0.1946(3) -0.2307(2) 0.73865(10) 0.0667(6) Uani 1 1 d . . . . .
C00A C 0.1306(2) 0.0840(2) 0.74698(9) 0.0456(5) Uani 1 1 d . . . . .
H00C H 0.162598 0.017755 0.742858 0.055 Uiso 1 1 calc R . . . .
C00B C -0.0132(2) 0.03744(19) 0.74927(8) 0.0411(4) Uani 1 1 d . . . . .
C00C C 0.34214(18) 0.74425(19) 0.75454(8) 0.0387(4) Uani 1 1 d . . . . .
C00D C 0.3289(2) 0.7095(2) 0.68023(9) 0.0473(5) Uani 1 1 d . . . . .
H00D H 0.334135 0.783843 0.649848 0.057 Uiso 1 1 calc R . . . .
C00E C 0.3641(3) 0.4945(3) 0.83381(11) 0.0560(5) Uani 1 1 d . . . . .
H00E H 0.432482 0.593662 0.843832 0.084 Uiso 1 1 calc GR . . . .
H00F H 0.412374 0.439044 0.833860 0.084 Uiso 1 1 calc GR . . . .
H00G H 0.289058 0.456767 0.866917 0.084 Uiso 1 1 calc GR . . . .
C00F C 0.4902(2) 0.8202(2) 0.78372(10) 0.0497(5) Uani 1 1 d . . . . .
H00H H 0.542176 0.917331 0.766858 0.074 Uiso 1 1 calc GR . . . .
H00I H 0.540323 0.769883 0.771652 0.074 Uiso 1 1 calc GR . . . .
H00J H 0.483606 0.822492 0.831451 0.074 Uiso 1 1 calc GR . . . .
C00G C 0.4095(2) 0.5315(2) 0.70933(11) 0.0511(5) Uani 1 1 d . . . . .
H00K H 0.503907 0.565260 0.729170 0.061 Uiso 1 1 calc R . . . .
H00L H 0.387093 0.447082 0.682636 0.061 Uiso 1 1 calc R . . . .
C00H C -0.1148(2) -0.1124(2) 0.74348(9) 0.0501(5) Uani 1 1 d . . . . .
C00I C 0.4191(2) 0.6468(2) 0.66388(9) 0.0548(6) Uani 1 1 d . . . . .
C00J C 0.2715(3) 0.8309(2) 0.77277(14) 0.0581(6) Uani 1 1 d . . . . .
H00M H 0.329718 0.928155 0.756846 0.087 Uiso 1 1 calc GR . . . .
H00N H 0.262370 0.831784 0.820413 0.087 Uiso 1 1 calc GR . . . .
H00O H 0.177404 0.788031 0.752697 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
C001 C002 1.396(2) . ?
C001 C006 1.388(3) . ?
C002 C004 1.537(2) . ?
C002 C007 1.398(3) . ?
O003 C00I 1.212(2) . ?
C004 C005 1.532(2) . ?
C004 C00E 1.550(2) . ?
C004 C00G 1.559(2) . ?
C005 C008 1.546(2) . ?
C005 C00C 1.572(2) . ?
C006 C00B 1.388(3) . ?
C007 C00A 1.382(3) . ?
C008 C00D 1.550(3) . ?
N009 C00H 1.144(3) . ?
C00A C00B 1.387(3) . ?
C00B C00H 1.449(3) . ?
C00C C00D 1.555(3) . ?
C00C C00F 1.520(3) . ?
C00C C00J 1.533(3) . ?
C00D C00I 1.489(3) . ?
C00G C00I 1.524(3) . ?

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
C006 C001 C002 121.58(16) . . ?
C001 C002 C004 123.67(15) . . ?
C001 C002 C007 117.10(16) . . ?
C007 C002 C004 119.08(15) . . ?
C002 C004 C00E 105.18(15) . . ?
C002 C004 C00G 110.04(14) . . ?
C005 C004 C002 111.92(13) . . ?
C005 C004 C00E 108.87(15) . . ?
C005 C004 C00G 108.30(14) . . ?
C00E C004 C00G 112.55(17) . . ?
C004 C005 C008 109.26(14) . . ?
C004 C005 C00C 115.73(13) . . ?
C008 C005 C00C 87.10(13) . . ?
C001 C006 C00B 119.85(18) . . ?
C00A C007 C002 121.98(18) . . ?
C005 C008 C00D 86.78(14) . . ?
C007 C00A C00B 119.73(17) . . ?
C006 C00B C00H 120.41(19) . . ?
C00A C00B C006 119.75(18) . . ?
C00A C00B C00H 119.82(18) . . ?
C00D C00C C005 85.69(13) . . ?
C00F C00C C005 123.84(15) . . ?
C00F C00C C00D 117.41(16) . . ?
C00F C00C C00J 106.99(16) . . ?
C00J C00C C005 109.71(14) . . ?
C00J C00C C00D 111.94(17) . . ?
C008 C00D C00C 87.60(14) . . ?
C00I C00D C008 106.10(16) . . ?
C00I C00D C00C 109.21(16) . . ?
C00I C00G C004 116.01(17) . . ?
N009 C00H C00B 179.6(3) . . ?
O003 C00I C00D 123.0(2) . . ?
O003 C00I C00G 120.1(2) . . ?
C00D C00I C00G 116.92(15) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: DCM, EtOAc'
####################################################################### 
# 
# 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_20201229fl_0m_a_sq
_audit_block_doi                 10.5517/ccdc.csd.cc2974c2
_database_code_depnum_ccdc_archive 'CCDC 2122023'
loop_
_audit_author_name
_audit_author_address
'Sheng Zhang'
;Anhui University
China
;
_audit_update_record             
;
2021-11-15 deposited with the CCDC.	2022-01-10 downloaded from the CCDC.
;
_audit_creation_date             2020-12-29
_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        
'(3S,8S,10R,13S,16R,17S)-17-acetyl-16-(4-cyanophenyl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate'
_chemical_formula_moiety         'C30 H37 N O3'
_chemical_formula_sum            'C30 H37 N O3'
_chemical_formula_weight         459.60
_chemical_absolute_configuration ad
_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 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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      hexagonal
_space_group_IT_number           170
_space_group_name_H-M_alt        'P 65'
_space_group_name_Hall           'P 65'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'
'-x, -y, z+1/2'
'y, -x+y, z+1/6'
'x-y, x, z+5/6'

_cell_length_a                   22.005(2)
_cell_length_b                   22.005(2)
_cell_length_c                   10.6121(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4450.2(11)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    9184
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      54.980
_cell_measurement_theta_min      3.495
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.327
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6282
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1502 before and 0.0831 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    1.029
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0514
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            120880
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.049
_diffrn_reflns_theta_min         2.017
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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         0.887
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                5531
_reflns_number_total             5647
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 2562 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5647
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0295
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0669P)²+0.1679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0902
_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. Uiso/Uaniso restraints and constraints
Uanis(C00Y) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C00C(H00C), C00J(H00J), C00K(H00K), C004(H004), C008(H008), C009(H009)
3.b Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00B), C00E(H00D,H00E), C00H(H00F,H00H), C00P(H00I,H00L), C00R(H00M,
 H00N), C00U(H00T,H00U), C00V(H00V,H00W)
3.c Aromatic/amide H refined with riding coordinates:
 C00G(H00G), C00Q(H00Q), C00S(H00S), C006(H006), C007(H007)
3.d Idealised Me refined as rotating group:
 C00T(H00O,H00P,H00R), C00W(H00X,H00Y,H00Z), C00X(H010,H011,H012), C00Y(H00$,
 H00:,H00)
;
_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
O001 O 1.18086(7) 0.84210(7) 0.07803(13) 0.0594(4) Uani 1 1 d . . . . .
O002 O 1.07689(9) 0.81371(10) -0.00800(19) 0.0789(5) Uani 1 1 d . . . . .
O003 O 1.05191(8) 0.55547(10) 1.10151(14) 0.0687(4) Uani 1 1 d . . . . .
N00A N 0.62628(8) 0.33401(10) 0.9983(2) 0.0696(5) Uani 1 1 d . . . . .
C00B C 1.07812(7) 0.62343(7) 0.79978(14) 0.0343(3) Uani 1 1 d . . . . .
C00C C 1.02718(7) 0.64038(7) 0.72904(14) 0.0340(3) Uani 1 1 d . . . . .
H00C H 0.995695 0.597622 0.678591 0.041 Uiso 1 1 calc R . . . .
C00D C 0.98162(8) 0.64476(8) 0.83300(16) 0.0386(3) Uani 1 1 d . . . . .
H00A H 0.935233 0.633847 0.799580 0.046 Uiso 1 1 calc R . . . .
H00B H 1.004623 0.692168 0.871111 0.046 Uiso 1 1 calc R . . . .
C00E C 1.11541(8) 0.60309(8) 0.70134(15) 0.0391(3) Uani 1 1 d . . . . .
H00D H 1.080657 0.559756 0.657629 0.047 Uiso 1 1 calc R . . . .
H00E H 1.149769 0.593387 0.743621 0.047 Uiso 1 1 calc R . . . .
C00F C 1.09758(8) 0.77223(8) 0.39640(16) 0.0411(3) Uani 1 1 d . . . . .
C00G C 0.79253(8) 0.43205(9) 0.86114(17) 0.0443(3) Uani 1 1 d . . . . .
H00G H 0.768956 0.400031 0.794340 0.053 Uiso 1 1 calc R . . . .
C00H C 1.15340(8) 0.66202(9) 0.60473(16) 0.0413(3) Uani 1 1 d . . . . .
H00F H 1.174673 0.646198 0.539670 0.050 Uiso 1 1 calc R . . . .
H00H H 1.191940 0.703251 0.647621 0.050 Uiso 1 1 calc R . . . .
C00I C 0.75685(8) 0.42863(8) 0.97155(18) 0.0428(4) Uani 1 1 d . . . . .
C00J C 1.10537(7) 0.68458(7) 0.53969(14) 0.0349(3) Uani 1 1 d . . . . .
H00J H 1.070769 0.643358 0.489108 0.042 Uiso 1 1 calc R . . . .
C00K C 1.06229(7) 0.70062(8) 0.63489(15) 0.0367(3) Uani 1 1 d . . . . .
H00K H 1.094365 0.744873 0.681130 0.044 Uiso 1 1 calc R . . . .
C00L C 1.13977(13) 0.84826(12) -0.0079(2) 0.0617(5) Uani 1 1 d . . . . .
C00M C 1.14555(7) 0.74566(8) 0.44483(15) 0.0392(3) Uani 1 1 d . . . . .
C00N C 1.05707(8) 0.54287(10) 0.99247(18) 0.0488(4) Uani 1 1 d . . . . .
C00O C 0.68380(9) 0.37539(9) 0.9860(2) 0.0513(4) Uani 1 1 d . . . . .
C00P C 1.00727(9) 0.71022(10) 0.56417(18) 0.0492(4) Uani 1 1 d . . . . .
H00I H 0.968044 0.663575 0.539679 0.059 Uiso 1 1 calc R . . . .
H00L H 0.988276 0.732307 0.621158 0.059 Uiso 1 1 calc R . . . .
C00Q C 1.03628(9) 0.75476(10) 0.44803(19) 0.0503(4) Uani 1 1 d . . . . .
H00Q H 1.008625 0.771521 0.409001 0.060 Uiso 1 1 calc R . . . .
C00R C 1.12395(10) 0.82070(9) 0.28317(18) 0.0495(4) Uani 1 1 d . . . . .
H00M H 1.086386 0.829332 0.252822 0.059 Uiso 1 1 calc R . . . .
H00N H 1.164399 0.866329 0.308717 0.059 Uiso 1 1 calc R . . . .
C00S C 0.79105(8) 0.47500(8) 1.06950(17) 0.0428(3) Uani 1 1 d . . . . .
H00S H 0.766713 0.472067 1.145239 0.051 Uiso 1 1 calc R . . . .
C00T C 1.13125(8) 0.68457(9) 0.88165(17) 0.0450(4) Uani 1 1 d . . . . .
H00O H 1.157809 0.726259 0.828902 0.067 Uiso 1 1 calc GR . . . .
H00P H 1.163589 0.671773 0.920982 0.067 Uiso 1 1 calc GR . . . .
H00R H 1.106240 0.694684 0.947314 0.067 Uiso 1 1 calc GR . . . .
C00U C 1.16844(11) 0.71777(10) 0.33098(18) 0.0522(4) Uani 1 1 d . . . . .
H00T H 1.204264 0.706156 0.359543 0.063 Uiso 1 1 calc R . . . .
H00U H 1.127406 0.673873 0.300579 0.063 Uiso 1 1 calc R . . . .
C00V C 1.19847(11) 0.76951(11) 0.2212(2) 0.0581(5) Uani 1 1 d . . . . .
H00V H 1.242125 0.811930 0.248306 0.070 Uiso 1 1 calc R . . . .
H00W H 1.210205 0.747719 0.150720 0.070 Uiso 1 1 calc R . . . .
C00W C 1.21034(9) 0.80715(10) 0.5065(2) 0.0568(5) Uani 1 1 d . . . . .
H00X H 1.229172 0.848156 0.450880 0.085 Uiso 1 1 calc GR . . . .
H00Y H 1.246192 0.793880 0.520577 0.085 Uiso 1 1 calc GR . . . .
H00Z H 1.196956 0.818604 0.587325 0.085 Uiso 1 1 calc GR . . . .
C00X C 1.09655(13) 0.50595(14) 0.9570(3) 0.0712(7) Uani 1 1 d . . . . .
H010 H 1.070174 0.470454 0.892574 0.107 Uiso 1 1 calc GR . . . .
H011 H 1.102442 0.483187 1.031620 0.107 Uiso 1 1 calc GR . . . .
H012 H 1.142744 0.540145 0.923554 0.107 Uiso 1 1 calc GR . . . .
C00Y C 1.18271(18) 0.90305(19) -0.1039(3) 0.0984(10) Uani 1 1 d . U . . .
H00$ H 1.151913 0.913220 -0.155443 0.148 Uiso 1 1 calc GR . . . .
H00: H 1.206945 0.885818 -0.158029 0.148 Uiso 1 1 calc GR . . . .
H00 H 1.217367 0.945952 -0.060968 0.148 Uiso 1 1 calc GR . . . .
C004 C 0.97381(7) 0.58857(8) 0.93167(14) 0.0372(3) Uani 1 1 d . . . . .
H004 H 0.990730 0.612305 1.015060 0.045 Uiso 1 1 calc R . . . .
C005 C 0.89802(7) 0.53047(8) 0.94627(14) 0.0359(3) Uani 1 1 d . . . . .
C006 C 0.86145(8) 0.52596(8) 1.05591(15) 0.0391(3) Uani 1 1 d . . . . .
H006 H 0.884809 0.558128 1.122619 0.047 Uiso 1 1 calc R . . . .
C007 C 0.86289(8) 0.48265(9) 0.84942(15) 0.0421(3) Uani 1 1 d . . . . .
H007 H 0.887447 0.484754 0.774434 0.050 Uiso 1 1 calc R . . . .
C008 C 1.02449(7) 0.56297(8) 0.88651(15) 0.0374(3) Uani 1 1 d . . . . .
H008 H 0.996981 0.520522 0.832665 0.045 Uiso 1 1 calc R . . . .
C009 C 1.14604(9) 0.78998(9) 0.17728(17) 0.0498(4) Uani 1 1 d . . . . .
H009 H 1.103846 0.747941 0.141879 0.060 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
O001 C00L 1.338(3) . ?
O001 C009 1.4605(19) . ?
O002 C00L 1.200(3) . ?
O003 C00N 1.208(3) . ?
N00A C00O 1.138(2) . ?
C00B C00C 1.5419(19) . ?
C00B C00E 1.5270(19) . ?
C00B C00T 1.536(2) . ?
C00B C008 1.562(2) . ?
C00C C00D 1.526(2) . ?
C00C C00K 1.526(2) . ?
C00D C004 1.563(2) . ?
C00E C00H 1.532(2) . ?
C00F C00M 1.529(2) . ?
C00F C00Q 1.323(2) . ?
C00F C00R 1.516(2) . ?
C00G C00I 1.391(3) . ?
C00G C007 1.389(2) . ?
C00H C00J 1.537(2) . ?
C00I C00O 1.448(2) . ?
C00I C00S 1.386(3) . ?
C00J C00K 1.5423(19) . ?
C00J C00M 1.553(2) . ?
C00K C00P 1.526(2) . ?
C00L C00Y 1.498(3) . ?
C00M C00U 1.549(2) . ?
C00M C00W 1.537(2) . ?
C00N C00X 1.504(3) . ?
C00N C008 1.513(2) . ?
C00P C00Q 1.504(2) . ?
C00R C009 1.512(3) . ?
C00S C006 1.393(2) . ?
C00U C00V 1.529(3) . ?
C00V C009 1.507(3) . ?
C004 C005 1.5192(19) . ?
C004 C008 1.555(2) . ?
C005 C006 1.390(2) . ?
C005 C007 1.396(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00L O001 C009 117.09(15) . . ?
C00C C00B C008 99.31(10) . . ?
C00E C00B C00C 107.46(12) . . ?
C00E C00B C00T 111.01(12) . . ?
C00E C00B C008 116.18(12) . . ?
C00T C00B C00C 112.99(12) . . ?
C00T C00B C008 109.44(13) . . ?
C00D C00C C00B 104.09(12) . . ?
C00K C00C C00B 114.54(11) . . ?
C00K C00C C00D 118.81(12) . . ?
C00C C00D C004 104.49(11) . . ?
C00B C00E C00H 110.82(12) . . ?
C00Q C00F C00M 123.26(15) . . ?
C00Q C00F C00R 120.58(15) . . ?
C00R C00F C00M 116.16(14) . . ?
C007 C00G C00I 119.44(16) . . ?
C00E C00H C00J 113.66(12) . . ?
C00G C00I C00O 120.09(18) . . ?
C00S C00I C00G 120.52(14) . . ?
C00S C00I C00O 119.38(16) . . ?
C00H C00J C00K 112.35(12) . . ?
C00H C00J C00M 112.62(11) . . ?
C00K C00J C00M 112.05(12) . . ?
C00C C00K C00J 109.41(11) . . ?
C00C C00K C00P 110.49(12) . . ?
C00P C00K C00J 109.30(14) . . ?
O001 C00L C00Y 111.0(2) . . ?
O002 C00L O001 124.02(19) . . ?
O002 C00L C00Y 125.0(2) . . ?
C00F C00M C00J 110.23(12) . . ?
C00F C00M C00U 108.23(14) . . ?
C00F C00M C00W 108.69(14) . . ?
C00U C00M C00J 108.64(12) . . ?
C00W C00M C00J 111.22(14) . . ?
C00W C00M C00U 109.79(15) . . ?
O003 C00N C00X 120.64(18) . . ?
O003 C00N C008 122.13(16) . . ?
C00X C00N C008 117.23(17) . . ?
N00A C00O C00I 179.3(3) . . ?
C00Q C00P C00K 112.69(13) . . ?
C00F C00Q C00P 124.60(15) . . ?
C009 C00R C00F 111.71(14) . . ?
C00I C00S C006 119.41(15) . . ?
C00V C00U C00M 113.84(15) . . ?
C009 C00V C00U 110.36(15) . . ?
C005 C004 C00D 111.98(12) . . ?
C005 C004 C008 114.26(12) . . ?
C008 C004 C00D 105.37(12) . . ?
C006 C005 C004 119.89(14) . . ?
C006 C005 C007 118.69(14) . . ?
C007 C005 C004 121.38(13) . . ?
C005 C006 C00S 121.01(15) . . ?
C00G C007 C005 120.92(15) . . ?
C00N C008 C00B 114.84(12) . . ?
C00N C008 C004 114.02(13) . . ?
C004 C008 C00B 104.26(11) . . ?
O001 C009 C00R 110.16(15) . . ?
O001 C009 C00V 106.16(14) . . ?
C00V C009 C00R 111.66(16) . . ?

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