# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_20170301wp_0m
_database_code_depnum_ccdc_archive 'CCDC 1552864'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-08-18 downloaded from the CCDC.
;
_audit_creation_date             2017-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        
'(3aR,5aR,7aS,E)-2,3a,6,6-tetramethyl-3a,4,5,5a,6,7,7a,9,10,10a-decahydro-8H-cyclobuta[6,7]cyclonona[1,2-d]oxazol-8-one oxime'
_chemical_formula_moiety         'C16 H26 N2 O2'
_chemical_formula_sum            'C16 H26 N2 O2'
_chemical_formula_weight         278.39
_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 0.0181 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                   8.9540(4)
_cell_length_b                   8.9365(5)
_cell_length_c                   10.4047(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.970(3)
_cell_angle_gamma                90
_cell_volume                     819.98(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3779
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.540
_cell_measurement_theta_min      4.314
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0703 before and 0.0338 after correction. The Ratio of minimum to maximum transmission is 0.9112. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.128
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             304
_exptl_crystal_preparation       'in methanol'
_exptl_crystal_recrystallization_method 'colourless needle'
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5699
_diffrn_reflns_point_group_measured_fraction_full 0.801
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.540
_diffrn_reflns_theta_min         4.314
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     ?
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.529
_reflns_Friedel_fraction_full    0.598
_reflns_Friedel_fraction_max     0.594
_reflns_number_gt                2315
_reflns_number_total             2415
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.118
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 784 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2415
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.056
_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)+(0.0644P)²+0.0392P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0923
_refine_ls_wR_factor_ref         0.0944
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C006(H006), C00A(H00A), C00C(H00D)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00D(H00E,H00F), C00E(H00G,H00H), C00H(H00O,H00P), C00I(H00Q,
 H00R)
2.c Idealised Me refined as rotating group:
 C00F(H00I,H00J,H00K), C00G(H00L,H00M,H00N), C00J(H00S,H00T,H00U), C00K(H00V,
 H00W,H00X)
2.d Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_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 0.71761(13) 0.6754(2) 0.39463(12) 0.0475(3) Uani 1 1 d . . . . .
O002 O 0.26841(16) 0.7242(2) 0.55992(18) 0.0657(5) Uani 1 1 d . . . . .
H002 H 0.177249 0.708677 0.538352 0.099 Uiso 1 1 calc GR . . . .
N003 N 0.95922(15) 0.6743(2) 0.49669(15) 0.0433(4) Uani 1 1 d . . . . .
N004 N 0.33089(18) 0.6186(2) 0.65558(17) 0.0513(4) Uani 1 1 d . . . . .
C005 C 0.86718(19) 0.6749(2) 0.39067(18) 0.0421(4) Uani 1 1 d . . . . .
C006 C 0.70288(17) 0.6752(3) 0.53214(16) 0.0391(4) Uani 1 1 d . . . . .
H006 H 0.656749 0.580448 0.552010 0.047 Uiso 1 1 calc R . . . .
C007 C 0.6306(2) 0.3386(3) 0.88226(18) 0.0509(5) Uani 1 1 d . . . . .
C008 C 0.87131(17) 0.6790(2) 0.60569(16) 0.0395(4) Uani 1 1 d . . . . .
C009 C 0.4634(2) 0.6578(3) 0.71056(18) 0.0446(5) Uani 1 1 d . . . . .
C00A C 0.6808(2) 0.4583(2) 0.78874(18) 0.0417(4) Uani 1 1 d . . . . .
H00A H 0.656211 0.419950 0.699325 0.050 Uiso 1 1 calc R . . . .
C00B C 0.9157(2) 0.5388(2) 0.6884(2) 0.0457(5) Uani 1 1 d . . . . .
H00B H 1.024997 0.539910 0.715207 0.055 Uiso 1 1 calc R . . . .
H00C H 0.891085 0.452356 0.632361 0.055 Uiso 1 1 calc R . . . .
C00C C 0.5454(2) 0.5574(3) 0.81498(19) 0.0459(5) Uani 1 1 d . . . . .
H00D H 0.579831 0.617850 0.893079 0.055 Uiso 1 1 calc R . . . .
C00D C 0.5960(2) 0.8022(3) 0.5509(2) 0.0498(5) Uani 1 1 d . . . . .
H00E H 0.508911 0.798074 0.481103 0.060 Uiso 1 1 calc R . . . .
H00F H 0.647450 0.896371 0.543055 0.060 Uiso 1 1 calc R . . . .
C00E C 0.8448(2) 0.5149(3) 0.8109(2) 0.0493(5) Uani 1 1 d . . . . .
H00G H 0.907199 0.444004 0.866936 0.059 Uiso 1 1 calc R . . . .
H00H H 0.848645 0.609076 0.857694 0.059 Uiso 1 1 calc R . . . .
C00F C 0.9057(2) 0.6764(4) 0.25711(19) 0.0561(5) Uani 1 1 d . . . . .
H00I H 0.865221 0.588453 0.210746 0.084 Uiso 1 1 calc GR . . . .
H00J H 1.013848 0.678024 0.263123 0.084 Uiso 1 1 calc GR . . . .
H00K H 0.862714 0.763856 0.211320 0.084 Uiso 1 1 calc GR . . . .
C00G C 0.9185(2) 0.8226(3) 0.6807(2) 0.0543(5) Uani 1 1 d . . . . .
H00L H 1.026666 0.823695 0.707474 0.081 Uiso 1 1 calc GR . . . .
H00M H 0.870624 0.827391 0.756331 0.081 Uiso 1 1 calc GR . . . .
H00N H 0.888088 0.907346 0.625642 0.081 Uiso 1 1 calc GR . . . .
C00H C 0.4731(3) 0.4132(3) 0.8567(2) 0.0546(5) Uani 1 1 d . . . . .
H00O H 0.402415 0.366451 0.787035 0.066 Uiso 1 1 calc R . . . .
H00P H 0.428077 0.424736 0.934452 0.066 Uiso 1 1 calc R . . . .
C00I C 0.5396(2) 0.8005(3) 0.6813(2) 0.0508(5) Uani 1 1 d . . . . .
H00Q H 0.625155 0.818543 0.750523 0.061 Uiso 1 1 calc R . . . .
H00R H 0.468738 0.882438 0.682117 0.061 Uiso 1 1 calc R . . . .
C00J C 0.6395(3) 0.1782(4) 0.8391(3) 0.0693(6) Uani 1 1 d . . . . .
H00S H 0.595925 0.169884 0.748381 0.104 Uiso 1 1 calc GR . . . .
H00T H 0.584512 0.115536 0.889610 0.104 Uiso 1 1 calc GR . . . .
H00U H 0.743641 0.147217 0.851920 0.104 Uiso 1 1 calc GR . . . .
C00K C 0.7077(3) 0.3576(4) 1.0243(2) 0.0761(9) Uani 1 1 d . . . . .
H00V H 0.812892 0.331144 1.032763 0.114 Uiso 1 1 calc GR . . . .
H00W H 0.659555 0.293784 1.079060 0.114 Uiso 1 1 calc GR . . . .
H00X H 0.699217 0.459931 1.050221 0.114 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
O001 C005 1.347(2) . ?
O001 C006 1.459(2) . ?
O002 H002 0.8200 . ?
O002 N004 1.415(3) . ?
N003 C005 1.257(3) . ?
N003 C008 1.489(2) . ?
N004 C009 1.274(3) . ?
C005 C00F 1.489(3) . ?
C006 H006 0.9800 . ?
C006 C008 1.569(2) . ?
C006 C00D 1.518(3) . ?
C007 C00A 1.564(3) . ?
C007 C00H 1.541(3) . ?
C007 C00J 1.508(4) . ?
C007 C00K 1.529(3) . ?
C008 C00B 1.533(3) . ?
C008 C00G 1.523(3) . ?
C009 C00C 1.499(3) . ?
C009 C00I 1.502(3) . ?
C00A H00A 0.9800 . ?
C00A C00C 1.563(3) . ?
C00A C00E 1.532(3) . ?
C00B H00B 0.9700 . ?
C00B H00C 0.9700 . ?
C00B C00E 1.535(3) . ?
C00C H00D 0.9800 . ?
C00C C00H 1.538(3) . ?
C00D H00E 0.9700 . ?
C00D H00F 0.9700 . ?
C00D C00I 1.527(3) . ?
C00E H00G 0.9700 . ?
C00E H00H 0.9700 . ?
C00F H00I 0.9600 . ?
C00F H00J 0.9600 . ?
C00F H00K 0.9600 . ?
C00G H00L 0.9600 . ?
C00G H00M 0.9600 . ?
C00G H00N 0.9600 . ?
C00H H00O 0.9700 . ?
C00H H00P 0.9700 . ?
C00I H00Q 0.9700 . ?
C00I H00R 0.9700 . ?
C00J H00S 0.9600 . ?
C00J H00T 0.9600 . ?
C00J H00U 0.9600 . ?
C00K H00V 0.9600 . ?
C00K H00W 0.9600 . ?
C00K H00X 0.9600 . ?

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
C005 O001 C006 106.81(13) . . ?
N004 O002 H002 109.5 . . ?
C005 N003 C008 108.39(13) . . ?
C009 N004 O002 110.89(19) . . ?
O001 C005 C00F 114.87(16) . . ?
N003 C005 O001 118.51(16) . . ?
N003 C005 C00F 126.62(17) . . ?
O001 C006 H006 108.7 . . ?
O001 C006 C008 103.64(12) . . ?
O001 C006 C00D 106.95(16) . . ?
C008 C006 H006 108.7 . . ?
C00D C006 H006 108.7 . . ?
C00D C006 C008 119.68(18) . . ?
C00H C007 C00A 87.12(16) . . ?
C00J C007 C00A 115.42(18) . . ?
C00J C007 C00H 117.0(2) . . ?
C00J C007 C00K 110.8(2) . . ?
C00K C007 C00A 113.25(19) . . ?
C00K C007 C00H 111.5(2) . . ?
N003 C008 C006 102.60(13) . . ?
N003 C008 C00B 106.52(16) . . ?
N003 C008 C00G 106.12(16) . . ?
C00B C008 C006 112.96(16) . . ?
C00G C008 C006 115.23(18) . . ?
C00G C008 C00B 112.27(15) . . ?
N004 C009 C00C 117.5(2) . . ?
N004 C009 C00I 124.2(2) . . ?
C00C C009 C00I 118.19(16) . . ?
C007 C00A H00A 108.1 . . ?
C00C C00A C007 87.92(16) . . ?
C00C C00A H00A 108.1 . . ?
C00E C00A C007 120.25(16) . . ?
C00E C00A H00A 108.1 . . ?
C00E C00A C00C 122.58(19) . . ?
C008 C00B H00B 107.7 . . ?
C008 C00B H00C 107.7 . . ?
C008 C00B C00E 118.40(17) . . ?
H00B C00B H00C 107.1 . . ?
C00E C00B H00B 107.7 . . ?
C00E C00B H00C 107.7 . . ?
C009 C00C C00A 120.65(16) . . ?
C009 C00C H00D 108.4 . . ?
C009 C00C C00H 121.89(17) . . ?
C00A C00C H00D 108.4 . . ?
C00H C00C C00A 87.22(17) . . ?
C00H C00C H00D 108.4 . . ?
C006 C00D H00E 108.6 . . ?
C006 C00D H00F 108.6 . . ?
C006 C00D C00I 114.82(18) . . ?
H00E C00D H00F 107.5 . . ?
C00I C00D H00E 108.6 . . ?
C00I C00D H00F 108.6 . . ?
C00A C00E C00B 116.41(16) . . ?
C00A C00E H00G 108.2 . . ?
C00A C00E H00H 108.2 . . ?
C00B C00E H00G 108.2 . . ?
C00B C00E H00H 108.2 . . ?
H00G C00E H00H 107.3 . . ?
C005 C00F H00I 109.5 . . ?
C005 C00F H00J 109.5 . . ?
C005 C00F H00K 109.5 . . ?
H00I C00F H00J 109.5 . . ?
H00I C00F H00K 109.5 . . ?
H00J C00F H00K 109.5 . . ?
C008 C00G H00L 109.5 . . ?
C008 C00G H00M 109.5 . . ?
C008 C00G H00N 109.5 . . ?
H00L C00G H00M 109.5 . . ?
H00L C00G H00N 109.5 . . ?
H00M C00G H00N 109.5 . . ?
C007 C00H H00O 113.7 . . ?
C007 C00H H00P 113.7 . . ?
C00C C00H C007 89.64(16) . . ?
C00C C00H H00O 113.7 . . ?
C00C C00H H00P 113.7 . . ?
H00O C00H H00P 111.0 . . ?
C009 C00I C00D 114.83(18) . . ?
C009 C00I H00Q 108.6 . . ?
C009 C00I H00R 108.6 . . ?
C00D C00I H00Q 108.6 . . ?
C00D C00I H00R 108.6 . . ?
H00Q C00I H00R 107.5 . . ?
C007 C00J H00S 109.5 . . ?
C007 C00J H00T 109.5 . . ?
C007 C00J H00U 109.5 . . ?
H00S C00J H00T 109.5 . . ?
H00S C00J H00U 109.5 . . ?
H00T C00J H00U 109.5 . . ?
C007 C00K H00V 109.5 . . ?
C007 C00K H00W 109.5 . . ?
C007 C00K H00X 109.5 . . ?
H00V C00K H00W 109.5 . . ?
H00V C00K H00X 109.5 . . ?
H00W C00K H00X 109.5 . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_exptl_crystal_mounting_method '10 mg'
_olex2_submission_original_sample_id 29-13
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cu_20161118_0m
_database_code_depnum_ccdc_archive 'CCDC 1519447'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-08-18 downloaded from the CCDC.
;
_audit_creation_date             2017-05-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        MSJ42-11
_chemical_formula_moiety         'C14 H23 N O2'
_chemical_formula_sum            'C14 H23 N O2'
_chemical_formula_weight         237.33
_chemical_absolute_configuration syn
_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 0.0181 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      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                   8.1257(8)
_cell_length_b                   10.3350(10)
_cell_length_c                   16.0543(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1348.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4310
_cell_measurement_temperature    293
_cell_measurement_theta_max      68.445
_cell_measurement_theta_min      6.104
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0495 before and 0.0358 after correction.
The Ratio of minimum to maximum transmission is 0.8367.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_preparation       'in MeOH-water'
_exptl_crystal_recrystallization_method -
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_av_unetI/netI     0.0338
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5708
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.445
_diffrn_reflns_theta_min         6.104
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_special_details          -
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                2304
_reflns_number_total             2387
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.198
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 906 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(2)
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2387
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0412
_refine_ls_restrained_S_all      1.083
_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)+(0.0739P)²+0.1500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1199
_refine_special_details          ShelXS
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C004(H004), C007(H007), C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00C(H00F,H00G), C00E(H00H,H00I), C00H(H00P,H00Q), C009(H00R,
 H00S)
2.c Idealised Me refined as rotating group:
 C00B(H00C,H00D,H00E), C00F(H00J,H00K,H00L), C00G(H00M,H00N,H00O)
2.d Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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 1.0704(2) 0.15557(17) 0.35198(15) 0.0593(5) Uani 1 1 d . . . . .
H001 H 1.165018 0.180634 0.344659 0.089 Uiso 1 1 calc GR . . . .
O002 O 0.3868(2) 0.2549(2) 0.32555(16) 0.0704(6) Uani 1 1 d . . . . .
N003 N 0.6504(2) 0.28233(18) 0.36772(12) 0.0397(4) Uani 1 1 d . . . . .
C00A C 1.0352(3) 0.3751(2) 0.3954(2) 0.0521(6) Uani 1 1 d . . . . .
H00A H 1.051136 0.344844 0.452036 0.062 Uiso 1 1 calc R . . . .
H00B H 1.143432 0.392397 0.372522 0.062 Uiso 1 1 calc R . . . .
C00B C 0.9372(4) 0.2988(3) 0.25437(17) 0.0650(8) Uani 1 1 d . . . . .
H00C H 1.042805 0.314270 0.229526 0.098 Uiso 1 1 calc GR . . . .
H00D H 0.871181 0.375570 0.250316 0.098 Uiso 1 1 calc GR . . . .
H00E H 0.883344 0.229094 0.225703 0.098 Uiso 1 1 calc GR . . . .
C00C C 0.9429(3) 0.5035(2) 0.39978(19) 0.0515(6) Uani 1 1 d . . . . .
H00F H 1.001645 0.562673 0.436022 0.062 Uiso 1 1 calc R . . . .
H00G H 0.937768 0.541797 0.344691 0.062 Uiso 1 1 calc R . . . .
C00D C 0.9595(3) 0.2631(2) 0.34515(15) 0.0422(5) Uani 1 1 d . . . . .
C00E C 0.5709(3) 0.0704(3) 0.34732(19) 0.0565(7) Uani 1 1 d . . . . .
H00H H 0.536933 0.026534 0.296741 0.068 Uiso 1 1 calc R . . . .
H00I H 0.521369 0.027152 0.394722 0.068 Uiso 1 1 calc R . . . .
C00F C 0.6560(4) 0.7073(3) 0.3909(2) 0.0637(8) Uani 1 1 d . . . . .
H00J H 0.753337 0.756434 0.403215 0.096 Uiso 1 1 calc GR . . . .
H00K H 0.560890 0.761509 0.397154 0.096 Uiso 1 1 calc GR . . . .
H00L H 0.661615 0.675878 0.334726 0.096 Uiso 1 1 calc GR . . . .
C00G C 0.6370(5) 0.6389(3) 0.54017(19) 0.0707(9) Uani 1 1 d . . . . .
H00M H 0.626707 0.565635 0.576529 0.106 Uiso 1 1 calc GR . . . .
H00N H 0.543941 0.694995 0.547453 0.106 Uiso 1 1 calc GR . . . .
H00O H 0.736125 0.685226 0.553268 0.106 Uiso 1 1 calc GR . . . .
C00H C 0.7558(3) 0.0719(3) 0.3548(2) 0.0635(8) Uani 1 1 d . . . . .
H00P H 0.806714 0.054454 0.301345 0.076 Uiso 1 1 calc R . . . .
H00Q H 0.792534 0.007136 0.394454 0.076 Uiso 1 1 calc R . . . .
C004 C 0.7709(3) 0.4835(2) 0.43250(13) 0.0379(5) Uani 1 1 d . . . . .
H004 H 0.778471 0.429071 0.482349 0.045 Uiso 1 1 calc R . . . .
C005 C 0.6438(3) 0.5931(2) 0.45078(16) 0.0471(6) Uani 1 1 d . . . . .
C006 C 0.5222(3) 0.2110(3) 0.34497(16) 0.0470(6) Uani 1 1 d . . . . .
C007 C 0.6444(3) 0.4226(2) 0.37452(14) 0.0390(5) Uani 1 1 d . . . . .
H007 H 0.654971 0.460841 0.318926 0.047 Uiso 1 1 calc R . . . .
C008 C 0.8004(3) 0.2091(2) 0.38548(14) 0.0394(5) Uani 1 1 d . . . . .
H008 H 0.815991 0.206103 0.445976 0.047 Uiso 1 1 calc R . . . .
C009 C 0.5096(3) 0.4942(2) 0.42307(19) 0.0538(6) Uani 1 1 d . . . . .
H00R H 0.462744 0.444525 0.468518 0.065 Uiso 1 1 calc R . . . .
H00S H 0.424214 0.531123 0.388182 0.065 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 H001 0.8200 . ?
O001 C00D 1.435(3) . ?
O002 C006 1.230(3) . ?
N003 C006 1.327(3) . ?
N003 C007 1.455(3) . ?
N003 C008 1.463(3) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00A C00C 1.526(3) . ?
C00A C00D 1.539(3) . ?
C00B H00C 0.9600 . ?
C00B H00D 0.9600 . ?
C00B H00E 0.9600 . ?
C00B C00D 1.514(4) . ?
C00C H00F 0.9700 . ?
C00C H00G 0.9700 . ?
C00C C004 1.507(3) . ?
C00D C008 1.550(3) . ?
C00E H00H 0.9700 . ?
C00E H00I 0.9700 . ?
C00E C00H 1.508(4) . ?
C00E C006 1.506(4) . ?
C00F H00J 0.9600 . ?
C00F H00K 0.9600 . ?
C00F H00L 0.9600 . ?
C00F C005 1.525(3) . ?
C00G H00M 0.9600 . ?
C00G H00N 0.9600 . ?
C00G H00O 0.9600 . ?
C00G C005 1.512(4) . ?
C00H H00P 0.9700 . ?
C00H H00Q 0.9700 . ?
C00H C008 1.544(3) . ?
C004 H004 0.9800 . ?
C004 C005 1.561(3) . ?
C004 C007 1.523(3) . ?
C005 C009 1.560(4) . ?
C007 H007 0.9800 . ?
C007 C009 1.534(3) . ?
C008 H008 0.9800 . ?
C009 H00R 0.9700 . ?
C009 H00S 0.9700 . ?

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
C00D O001 H001 109.5 . . ?
C006 N003 C007 123.2(2) . . ?
C006 N003 C008 114.83(19) . . ?
C007 N003 C008 121.94(17) . . ?
H00A C00A H00B 107.0 . . ?
C00C C00A H00A 107.6 . . ?
C00C C00A H00B 107.6 . . ?
C00C C00A C00D 118.8(2) . . ?
C00D C00A H00A 107.6 . . ?
C00D C00A H00B 107.6 . . ?
H00C C00B H00D 109.5 . . ?
H00C C00B H00E 109.5 . . ?
H00D C00B H00E 109.5 . . ?
C00D C00B H00C 109.5 . . ?
C00D C00B H00D 109.5 . . ?
C00D C00B H00E 109.5 . . ?
C00A C00C H00F 109.5 . . ?
C00A C00C H00G 109.5 . . ?
H00F C00C H00G 108.1 . . ?
C004 C00C C00A 110.64(19) . . ?
C004 C00C H00F 109.5 . . ?
C004 C00C H00G 109.5 . . ?
O001 C00D C00A 106.94(18) . . ?
O001 C00D C00B 109.7(2) . . ?
O001 C00D C008 102.29(17) . . ?
C00A C00D C008 112.66(19) . . ?
C00B C00D C00A 111.7(2) . . ?
C00B C00D C008 112.9(2) . . ?
H00H C00E H00I 108.9 . . ?
C00H C00E H00H 110.8 . . ?
C00H C00E H00I 110.8 . . ?
C006 C00E H00H 110.8 . . ?
C006 C00E H00I 110.8 . . ?
C006 C00E C00H 104.7(2) . . ?
H00J C00F H00K 109.5 . . ?
H00J C00F H00L 109.5 . . ?
H00K C00F H00L 109.5 . . ?
C005 C00F H00J 109.5 . . ?
C005 C00F H00K 109.5 . . ?
C005 C00F H00L 109.5 . . ?
H00M C00G H00N 109.5 . . ?
H00M C00G H00O 109.5 . . ?
H00N C00G H00O 109.5 . . ?
C005 C00G H00M 109.5 . . ?
C005 C00G H00N 109.5 . . ?
C005 C00G H00O 109.5 . . ?
C00E C00H H00P 110.6 . . ?
C00E C00H H00Q 110.6 . . ?
C00E C00H C008 105.6(2) . . ?
H00P C00H H00Q 108.8 . . ?
C008 C00H H00P 110.6 . . ?
C008 C00H H00Q 110.6 . . ?
C00C C004 H004 107.7 . . ?
C00C C004 C005 125.39(19) . . ?
C00C C004 C007 118.0(2) . . ?
C005 C004 H004 107.7 . . ?
C007 C004 H004 107.7 . . ?
C007 C004 C005 88.20(17) . . ?
C00F C005 C004 113.6(2) . . ?
C00F C005 C009 111.9(2) . . ?
C00G C005 C00F 111.0(2) . . ?
C00G C005 C004 115.5(2) . . ?
C00G C005 C009 116.8(2) . . ?
C009 C005 C004 86.15(17) . . ?
O002 C006 N003 124.5(2) . . ?
O002 C006 C00E 126.6(2) . . ?
N003 C006 C00E 108.8(2) . . ?
N003 C007 C004 115.79(18) . . ?
N003 C007 H007 109.3 . . ?
N003 C007 C009 122.9(2) . . ?
C004 C007 H007 109.3 . . ?
C004 C007 C009 88.39(18) . . ?
C009 C007 H007 109.3 . . ?
N003 C008 C00D 115.28(17) . . ?
N003 C008 C00H 102.58(18) . . ?
N003 C008 H008 108.5 . . ?
C00D C008 H008 108.5 . . ?
C00H C008 C00D 113.2(2) . . ?
C00H C008 H008 108.5 . . ?
C005 C009 H00R 114.0 . . ?
C005 C009 H00S 114.0 . . ?
C007 C009 C005 87.83(18) . . ?
C007 C009 H00R 114.0 . . ?
C007 C009 H00S 114.0 . . ?
H00R C009 H00S 111.2 . . ?

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
O001 C00D C008 N003 -163.70(18) . . . . ?
O001 C00D C008 C00H -46.0(3) . . . . ?
N003 C007 C009 C005 143.2(2) . . . . ?
C00A C00C C004 C005 176.0(2) . . . . ?
C00A C00C C004 C007 -74.5(3) . . . . ?
C00A C00D C008 N003 81.8(2) . . . . ?
C00A C00D C008 C00H -160.5(2) . . . . ?
C00B C00D C008 N003 -45.9(3) . . . . ?
C00B C00D C008 C00H 71.8(3) . . . . ?
C00C C00A C00D O001 -179.7(2) . . . . ?
C00C C00A C00D C00B 60.2(3) . . . . ?
C00C C00A C00D C008 -68.1(3) . . . . ?
C00C C004 C005 C00F 34.2(3) . . . . ?
C00C C004 C005 C00G -95.7(3) . . . . ?
C00C C004 C005 C009 146.4(2) . . . . ?
C00C C004 C007 N003 81.0(3) . . . . ?
C00C C004 C007 C009 -152.9(2) . . . . ?
C00D C00A C00C C004 55.8(3) . . . . ?
C00E C00H C008 N003 -16.9(3) . . . . ?
C00E C00H C008 C00D -141.8(2) . . . . ?
C00F C005 C009 C007 91.3(2) . . . . ?
C00G C005 C009 C007 -139.3(2) . . . . ?
C00H C00E C006 O002 167.1(3) . . . . ?
C00H C00E C006 N003 -13.0(3) . . . . ?
C004 C005 C009 C007 -22.63(17) . . . . ?
C004 C007 C009 C005 23.18(17) . . . . ?
C005 C004 C007 N003 -149.28(19) . . . . ?
C005 C004 C007 C009 -23.16(17) . . . . ?
C006 N003 C007 C004 156.2(2) . . . . ?
C006 N003 C007 C009 50.2(3) . . . . ?
C006 N003 C008 C00D 133.1(2) . . . . ?
C006 N003 C008 C00H 9.6(3) . . . . ?
C006 C00E C00H C008 18.3(3) . . . . ?
C007 N003 C006 O002 1.7(4) . . . . ?
C007 N003 C006 C00E -178.2(2) . . . . ?
C007 N003 C008 C00D -46.8(3) . . . . ?
C007 N003 C008 C00H -170.2(2) . . . . ?
C007 C004 C005 C00F -89.4(2) . . . . ?
C007 C004 C005 C00G 140.7(2) . . . . ?
C007 C004 C005 C009 22.80(17) . . . . ?
C008 N003 C006 O002 -178.2(2) . . . . ?
C008 N003 C006 C00E 2.0(3) . . . . ?
C008 N003 C007 C004 -24.0(3) . . . . ?
C008 N003 C007 C009 -130.0(2) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_exptl_crystal_mounting_method -
_olex2_submission_original_sample_id MSJ42-11
_olex2_submission_special_instructions 'No special instructions were received'
