# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_jml160_cu
_database_code_depnum_ccdc_archive 'CCDC 1566497'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2017-11-02 downloaded from the CCDC.
;
_audit_creation_date             2016-07-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 tert-Butyl N-{[(4aR*,8aR*)-octahydropyrano[4,3-b]pyran-4a-yl]methyl}carbamate 
;
_chemical_formula_moiety         'C14 H25 N O4'
_chemical_formula_sum            'C14 H25 N O4'
_chemical_formula_weight         271.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H25 N1 O4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.04739(18)
_cell_length_b                   12.2038(2)
_cell_length_c                   10.96322(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.7913(16)
_cell_angle_gamma                90.00
_cell_volume                     1477.35(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3537
_cell_measurement_temperature    120.01(19)
_cell_measurement_theta_max      73.6110
_cell_measurement_theta_min      5.3490
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.740
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43b (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.220
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             592
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -3 6 0.0557
-6 1 3 0.0641
7 -2 -2 0.0275
-7 1 1 0.0653
7 2 2 0.0457
4 5 5 0.0877
-7 0 0 0.0770
-5 -5 0 0.0887
3 -5 5 0.0689
-3 5 -5 0.0427
3 7 -2 0.0518
-2 -7 -2 0.0841
4 -1 -6 0.0534
5 3 -4 0.0415
6 1 4 0.0452

_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-3.0004 -3.0011 5.9997 -0.3648 -0.6389 -0.6834
-6.0003 0.9989 2.9990 -0.4140 0.1335 -0.8266
7.0002 -1.9988 -1.9987 0.4016 -0.3630 0.8869
-7.0000 0.9989 0.9985 -0.2129 0.3704 -0.8935
6.9995 2.0007 2.0023 -0.3532 -0.3927 0.9133
3.9990 5.0000 5.0022 -0.9296 -0.2530 0.5474
-6.9999 -0.0010 -0.0018 -0.0242 0.3778 -0.9001
-4.9995 -5.0007 -0.0018 0.4148 -0.1503 -0.8303
2.9998 -5.0002 5.0009 -0.0689 -1.0394 0.0441
-2.9998 5.0002 -5.0009 0.0689 1.0394 -0.0441
2.9997 7.0007 -1.9988 -0.3900 0.6092 0.7098
-1.9992 -7.0001 -2.0015 0.8026 -0.2974 -0.4577
4.0006 -0.9988 -5.9999 0.7139 0.2488 0.6621
5.0001 3.0012 -3.9990 0.1672 0.3480 0.8788
5.9994 1.0004 4.0022 -0.4748 -0.6057 0.6855

_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6401
_diffrn_reflns_theta_full        73.75
_diffrn_reflns_theta_max         73.75
_diffrn_reflns_theta_min         4.00
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(19)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  29.00   1.00    2.00    --  -38.50  57.00   0.00   93
  2  ω     79.00 106.00   1.00    2.00    --   42.71  37.00-150.00   27
  3  ω     38.00  63.00   1.00    2.00    --   42.71  37.00-180.00   25
  4  ω     31.00 144.00   1.00    8.00    --  104.98 -15.00-120.00  113
  5  ω     86.00 126.00   1.00    8.00    --  104.98 -30.00   0.00   40
  6  ω     87.00 119.00   1.00    8.00    --  104.98  45.00  60.00   32
  7  ω    124.00 175.00   1.00    8.00    --  104.98  45.00  60.00   51
  8  ω     86.00 119.00   1.00    8.00    --  104.98 -45.00 120.00   33
  9  ω     66.00  93.00   1.00    8.00    --  104.98 -61.00 -60.00   27
 10  ω     65.00  92.00   1.00    8.00    --  104.98 -62.00-151.96   27
 11  ω     37.00 127.00   1.00    8.00    --  104.98 -64.00 -94.96   90
 12  ω     37.00  92.00   1.00    8.00    --  104.98 -64.00-126.58   55
 13  ω   -106.00 -18.00   1.00    2.00    --  -38.50 -37.00-180.00   88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0034961000
_diffrn_orient_matrix_UB_12      -0.0864043000
_diffrn_orient_matrix_UB_13      -0.1022753000
_diffrn_orient_matrix_UB_21      -0.0539672000
_diffrn_orient_matrix_UB_22      0.0840406000
_diffrn_orient_matrix_UB_23      -0.0914416000
_diffrn_orient_matrix_UB_31      0.1285894000
_diffrn_orient_matrix_UB_32      0.0374848000
_diffrn_orient_matrix_UB_33      -0.0308441000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2549
_reflns_number_total             2882
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2882
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0374
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0393P)²+0.4832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0880
_refine_ls_wR_factor_ref         0.0918
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B),
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.52076(8) 0.63570(7) 0.54603(8) 0.0228(2) Uani 1 d . . .
N1 N 0.66469(9) 0.39541(8) 0.65170(10) 0.0226(2) Uani 1 d . . .
H1 H 0.6139 0.3886 0.5911 0.027 Uiso 1 calc . . R
C1 C 0.72238(10) 0.59331(10) 0.63408(11) 0.0184(2) Uani 1 d . . .
O2 O 0.77905(8) 0.78763(7) 0.64709(9) 0.0281(2) Uani 1 d . . .
C2 C 0.64250(11) 0.60683(10) 0.51882(11) 0.0208(3) Uani 1 d . . .
H2A H 0.6765 0.6633 0.4679 0.025 Uiso 1 calc . . R
H2B H 0.6420 0.5388 0.4731 0.025 Uiso 1 calc . . R
O3 O 0.81745(9) 0.30949(8) 0.75847(9) 0.0300(2) Uani 1 d . . .
C3 C 0.51712(11) 0.74148(10) 0.60295(12) 0.0227(3) Uani 1 d . . .
H3A H 0.4337 0.7611 0.6174 0.027 Uiso 1 calc . . R
H3B H 0.5503 0.7959 0.5488 0.027 Uiso 1 calc . . R
O4 O 0.68899(8) 0.21841(7) 0.62582(8) 0.0218(2) Uani 1 d . . .
C4 C 0.58910(11) 0.74165(10) 0.72309(11) 0.0221(3) Uani 1 d . . .
H4A H 0.5490 0.6950 0.7810 0.026 Uiso 1 calc . . R
H4B H 0.5912 0.8154 0.7560 0.026 Uiso 1 calc . . R
C5 C 0.71822(11) 0.70119(10) 0.70782(11) 0.0209(3) Uani 1 d . . .
H5 H 0.7568 0.6896 0.7885 0.025 Uiso 1 calc . . R
C6 C 0.90437(13) 0.76419(12) 0.63065(18) 0.0389(4) Uani 1 d . . .
H6A H 0.9437 0.7493 0.7093 0.047 Uiso 1 calc . . R
H6B H 0.9433 0.8275 0.5955 0.047 Uiso 1 calc . . R
C7 C 0.91881(13) 0.66613(13) 0.54760(16) 0.0367(4) Uani 1 d . . .
H7A H 1.0041 0.6495 0.5399 0.044 Uiso 1 calc . . R
H7B H 0.8848 0.6826 0.4670 0.044 Uiso 1 calc . . R
C8 C 0.85361(11) 0.56748(11) 0.60103(13) 0.0266(3) Uani 1 d . . .
H8A H 0.8980 0.5429 0.6737 0.032 Uiso 1 calc . . R
H8B H 0.8533 0.5081 0.5423 0.032 Uiso 1 calc . . R
C9 C 0.67370(11) 0.50035(10) 0.71337(11) 0.0211(3) Uani 1 d . . .
H9A H 0.7265 0.4924 0.7852 0.025 Uiso 1 calc . . R
H9B H 0.5941 0.5208 0.7406 0.025 Uiso 1 calc . . R
C10 C 0.73250(11) 0.30810(10) 0.68542(11) 0.0204(3) Uani 1 d . . .
C11 C 0.74992(12) 0.11161(10) 0.63752(12) 0.0226(3) Uani 1 d . . .
C12 C 0.87314(13) 0.11838(12) 0.58089(14) 0.0322(3) Uani 1 d . . .
H12A H 0.8638 0.1432 0.4980 0.048 Uiso 1 calc . . GR
H12B H 0.9103 0.0473 0.5823 0.048 Uiso 1 calc . . GR
H12C H 0.9233 0.1690 0.6265 0.048 Uiso 1 calc . . GR
C13 C 0.75604(14) 0.07359(12) 0.76946(12) 0.0320(3) Uani 1 d . . .
H13A H 0.8113 0.1194 0.8157 0.048 Uiso 1 calc . . GR
H13B H 0.7837 -0.0009 0.7731 0.048 Uiso 1 calc . . GR
H13C H 0.6770 0.0783 0.8031 0.048 Uiso 1 calc . . GR
C14 C 0.66598(13) 0.03762(11) 0.56226(13) 0.0292(3) Uani 1 d . . .
H14A H 0.5873 0.0370 0.5971 0.044 Uiso 1 calc . . GR
H14B H 0.6981 -0.0355 0.5621 0.044 Uiso 1 calc . . GR
H14C H 0.6594 0.0645 0.4800 0.044 Uiso 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 C2 1.4306(15) . ?
O1 C3 1.4350(15) . ?
N1 H1 0.8600 . ?
N1 C9 1.4501(16) . ?
N1 C10 1.3476(16) . ?
C1 C2 1.5275(16) . ?
C1 C5 1.5464(16) . ?
C1 C8 1.5380(16) . ?
C1 C9 1.5366(17) . ?
O2 C5 1.4267(15) . ?
O2 C6 1.4306(17) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
O3 C10 1.2146(16) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.5171(17) . ?
O4 C10 1.3552(15) . ?
O4 C11 1.4707(14) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.5237(17) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.515(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.5290(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C11 C12 1.5160(19) . ?
C11 C13 1.5185(18) . ?
C11 C14 1.5193(19) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C2 O1 C3 110.58(9) . . ?
C9 N1 H1 118.6 . . ?
C10 N1 H1 118.6 . . ?
C10 N1 C9 122.74(10) . . ?
C2 C1 C5 108.34(10) . . ?
C2 C1 C8 110.59(10) . . ?
C2 C1 C9 110.14(10) . . ?
C8 C1 C5 109.96(10) . . ?
C9 C1 C5 108.43(10) . . ?
C9 C1 C8 109.34(10) . . ?
C5 O2 C6 112.50(10) . . ?
O1 C2 C1 112.13(9) . . ?
O1 C2 H2A 109.2 . . ?
O1 C2 H2B 109.2 . . ?
C1 C2 H2A 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
O1 C3 H3A 109.4 . . ?
O1 C3 H3B 109.4 . . ?
O1 C3 C4 110.96(10) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C10 O4 C11 121.28(9) . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C3 C4 C5 111.79(10) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C1 C5 H5 109.3 . . ?
O2 C5 C1 111.31(10) . . ?
O2 C5 C4 105.54(10) . . ?
O2 C5 H5 109.3 . . ?
C4 C5 C1 112.12(10) . . ?
C4 C5 H5 109.3 . . ?
O2 C6 H6A 109.5 . . ?
O2 C6 H6B 109.5 . . ?
O2 C6 C7 110.74(12) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
C6 C7 H7A 109.8 . . ?
C6 C7 H7B 109.8 . . ?
C6 C7 C8 109.39(12) . . ?
H7A C7 H7B 108.2 . . ?
C8 C7 H7A 109.8 . . ?
C8 C7 H7B 109.8 . . ?
C1 C8 H8A 109.0 . . ?
C1 C8 H8B 109.0 . . ?
C7 C8 C1 112.81(11) . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N1 C9 C1 114.11(10) . . ?
N1 C9 H9A 108.7 . . ?
N1 C9 H9B 108.7 . . ?
C1 C9 H9A 108.7 . . ?
C1 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
N1 C10 O4 108.70(10) . . ?
O3 C10 N1 125.54(12) . . ?
O3 C10 O4 125.75(11) . . ?
O4 C11 C12 109.29(10) . . ?
O4 C11 C13 111.13(10) . . ?
O4 C11 C14 102.09(10) . . ?
C12 C11 C13 113.14(12) . . ?
C12 C11 C14 110.53(11) . . ?
C13 C11 C14 110.12(11) . . ?
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 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C4 C5 53.88(14) . . . . ?
O2 C6 C7 C8 -57.21(17) . . . . ?
C2 O1 C3 C4 -61.66(13) . . . . ?
C2 C1 C5 O2 -69.34(12) . . . . ?
C2 C1 C5 C4 48.62(13) . . . . ?
C2 C1 C8 C7 71.66(15) . . . . ?
C2 C1 C9 N1 57.50(13) . . . . ?
C3 O1 C2 C1 64.63(13) . . . . ?
C3 C4 C5 C1 -48.36(14) . . . . ?
C3 C4 C5 O2 72.98(12) . . . . ?
C5 C1 C2 O1 -56.87(13) . . . . ?
C5 C1 C8 C7 -47.95(15) . . . . ?
C5 C1 C9 N1 175.90(9) . . . . ?
C5 O2 C6 C7 63.97(16) . . . . ?
C6 O2 C5 C1 -60.80(14) . . . . ?
C6 O2 C5 C4 177.33(11) . . . . ?
C6 C7 C8 C1 50.77(16) . . . . ?
C8 C1 C2 O1 -177.44(10) . . . . ?
C8 C1 C5 O2 51.63(13) . . . . ?
C8 C1 C5 C4 169.59(10) . . . . ?
C8 C1 C9 N1 -64.22(13) . . . . ?
C9 N1 C10 O3 -9.7(2) . . . . ?
C9 N1 C10 O4 169.31(10) . . . . ?
C9 C1 C2 O1 61.59(13) . . . . ?
C9 C1 C5 O2 171.12(9) . . . . ?
C9 C1 C5 C4 -70.91(12) . . . . ?
C9 C1 C8 C7 -166.89(12) . . . . ?
C10 N1 C9 C1 114.36(13) . . . . ?
C10 O4 C11 C12 -66.04(14) . . . . ?
C10 O4 C11 C13 59.53(15) . . . . ?
C10 O4 C11 C14 176.90(10) . . . . ?
C11 O4 C10 N1 175.68(10) . . . . ?
C11 O4 C10 O3 -5.27(19) . . . . ?

_olex2_date_sample_data_collection 2016-07-18
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.264
_oxdiff_exptl_absorpt_empirical_full_min 0.880

####################################################################### 
# 
# 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_jml397_cu
_database_code_depnum_ccdc_archive 'CCDC 1566499'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2017-11-02 downloaded from the CCDC.
;
_audit_creation_date             2017-06-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 (4aR*,9bS*)-8-Methoxy-4a-(prop-2-en-1-yl)-2H,3H,4H,4aH,5H,9bH-indeno[2,1-e][1,3] oxazin-2-one
;
_chemical_formula_moiety         'C15 H17 N O3'
_chemical_formula_sum            'C15 H17 N O3'
_chemical_formula_weight         259.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C30 H34 N2 O6'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7483(5)
_cell_length_b                   9.9314(7)
_cell_length_c                   11.0967(8)
_cell_angle_alpha                63.764(7)
_cell_angle_beta                 79.148(6)
_cell_angle_gamma                74.800(6)
_cell_volume                     641.49(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2337
_cell_measurement_temperature    119.97(16)
_cell_measurement_theta_max      73.6950
_cell_measurement_theta_min      5.0600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.762
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.903
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             276
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 3 6 0.0549
-4 1 0 0.0568
4 0 1 0.0559
1 -3 -6 0.0171
1 6 3 0.0515
-1 2 7 0.0456
-1 -6 -3 0.0141
-3 3 -2 0.0672
-1 6 2 0.0617
3 4 6 0.0711
3 2 -3 0.0213
-3 -2 3 0.0374
0 6 0 0.0487
0 -5 1 0.0259

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0000 3.0000 6.0000 -0.3987 0.2678 -0.8086
-4.0000 1.0000 0.0000 -0.2222 -0.7134 -0.6653
4.0000 0.0000 1.0000 0.2363 0.7742 0.4959
1.0000 -3.0000 -6.0000 0.3987 -0.2678 0.8086
1.0000 6.0000 3.0000 0.5254 0.2791 -0.7160
-1.0000 2.0000 7.0000 -0.6478 0.3788 -0.7477
-1.0000 -6.0000 -3.0000 -0.5254 -0.2791 0.7160
-3.0000 3.0000 -2.0000 0.3644 -0.7633 -0.6495
-1.0000 6.0000 2.0000 0.4660 -0.1510 -0.9368
3.0000 4.0000 6.0000 0.0866 0.9310 -0.3735
3.0000 2.0000 -3.0000 0.8810 0.2085 0.3453
-3.0000 -2.0000 3.0000 -0.8810 -0.2085 -0.3453
-0.0000 6.0000 0.0000 0.7894 -0.1506 -0.6907
0.0000 -5.0000 1.0000 -0.7754 0.2114 0.5213

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4223
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.970
_diffrn_reflns_theta_min         4.458
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      119.97(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3095
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00 -13.00   1.00    1.00    --  -38.50 -57.00  90.00   29
  2  ω    -59.00 -17.00   1.00    1.00    --  -38.50 -65.00  56.67   42
  3  ω    -96.00 -62.00   1.00    1.00    --  -38.50 -65.00  56.67   34
  4  ω    -64.00 -20.00   1.00    1.00    --  -38.50  63.00 -90.00   44
  5  ω    -65.00  29.00   1.00    1.00    --  -38.50  65.00 -45.44   94
  6  ω     78.00 109.00   1.00    1.00    --   42.96  37.00 120.00   31
  7  ω    148.00 174.00   1.00    4.00    --  104.98  45.00  90.00   26
  8  ω     97.00 174.00   1.00    4.00    --  104.98  45.00 -90.00   77
  9  ω     84.00 126.00   1.00    4.00    --  104.98  45.00  90.00   42
 10  ω     73.00 100.00   1.00    4.00    --  104.98 -65.00  25.58   27
 11  ω     61.00  93.00   1.00    4.00    --  104.98 -65.00   5.56   32
 12  ω     56.00 119.00   1.00    4.00    --  104.98 -64.00 -44.72   63
 13  ω     50.00  96.00   1.00    4.00    --  104.98 -65.00-112.49   46
 14  ω     39.00 124.00   1.00    4.00    --  104.98 -30.00 -90.00   85
 15  ω     52.00 113.00   1.00    4.00    --  104.98 -65.00  81.10   61
 16  ω     52.00 112.00   1.00    4.00    --  104.98 -64.00 164.23   60
 17  ω     31.00 141.00   1.00    4.00    --  104.98 -15.00  90.00  110
 18  ω     31.00  66.00   1.00    1.00    --   42.96 -65.00 -25.82   35
 19  ω     17.00  53.00   1.00    1.00    --   42.96  63.00  48.85   36
 20  ω     22.00  87.00   1.00    1.00    --   42.96  65.00-175.43   65
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0884466000
_diffrn_orient_matrix_UB_12      0.1315749000
_diffrn_orient_matrix_UB_13      -0.1174983000
_diffrn_orient_matrix_UB_21      0.1720831000
_diffrn_orient_matrix_UB_22      -0.0251018000
_diffrn_orient_matrix_UB_23      0.0858641000
_diffrn_orient_matrix_UB_31      0.1375550000
_diffrn_orient_matrix_UB_32      -0.1151190000
_diffrn_orient_matrix_UB_33      -0.0542760000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2070
_reflns_number_total             2397
_reflns_odcompleteness_completeness 96.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.028
_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)+(0.0496P)²+0.1214P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0996
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C8(H8), C9(H9), C14(H14)
2.d X=CH2 refined with riding coordinates:
 C15(H15A,H15B)
2.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_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 0.40576(17) 0.91319(12) 0.36596(11) 0.0268(3) Uani 1 1 d . . . . .
N1 N 0.69079(18) 0.13528(14) 0.90361(12) 0.0196(3) Uani 1 1 d . . . . .
H1 H 0.6970 0.0402 0.9573 0.024 Uiso 1 1 calc R . . . .
C1 C 0.5617(2) 0.81677(17) 0.44524(14) 0.0212(3) Uani 1 1 d . . . . .
O2 O 0.48642(14) 0.36331(11) 0.76997(10) 0.0202(2) Uani 1 1 d . . . . .
C2 C 0.5226(2) 0.67201(17) 0.53235(14) 0.0205(3) Uani 1 1 d . . . . .
H2 H 0.3975 0.6472 0.5356 0.025 Uiso 1 1 calc R . . . .
O3 O 0.34351(15) 0.16752(12) 0.91025(11) 0.0252(3) Uani 1 1 d . . . . .
C3 C 0.6737(2) 0.56662(16) 0.61347(13) 0.0186(3) Uani 1 1 d . . . . .
C4 C 0.6802(2) 0.40180(16) 0.70466(13) 0.0181(3) Uani 1 1 d . . . . .
H4 H 0.7367 0.3421 0.6509 0.022 Uiso 1 1 calc R . . . .
C5 C 0.83657(19) 0.36262(15) 0.80478(13) 0.0163(3) Uani 1 1 d . . . . .
C6 C 0.9994(2) 0.45592(16) 0.70969(14) 0.0188(3) Uani 1 1 d . . . . .
H6A H 1.0762 0.4824 0.7589 0.023 Uiso 1 1 calc R . . . .
H6B H 1.0947 0.4000 0.6624 0.023 Uiso 1 1 calc R . . . .
C7 C 0.8641(2) 0.59849(17) 0.61273(13) 0.0186(3) Uani 1 1 d . . . . .
C8 C 0.8998(2) 0.74340(17) 0.52774(14) 0.0204(3) Uani 1 1 d . . . . .
H8 H 1.0242 0.7681 0.5263 0.024 Uiso 1 1 calc R . . . .
C9 C 0.7486(2) 0.85349(17) 0.44357(14) 0.0214(3) Uani 1 1 d . . . . .
H9 H 0.7732 0.9508 0.3868 0.026 Uiso 1 1 calc R . . . .
C10 C 0.4421(3) 1.05891(18) 0.26636(15) 0.0283(3) Uani 1 1 d . . . . .
H10A H 0.3278 1.1105 0.2115 0.043 Uiso 1 1 calc GR . . . .
H10B H 0.5658 1.0442 0.2107 0.043 Uiso 1 1 calc GR . . . .
H10C H 0.4571 1.1198 0.3101 0.043 Uiso 1 1 calc GR . . . .
C11 C 0.8881(2) 0.18808(16) 0.86647(14) 0.0184(3) Uani 1 1 d . . . . .
H11A H 0.9732 0.1514 0.8019 0.022 Uiso 1 1 calc R . . . .
H11B H 0.9628 0.1494 0.9457 0.022 Uiso 1 1 calc R . . . .
C12 C 0.5031(2) 0.21650(16) 0.86449(14) 0.0193(3) Uani 1 1 d . . . . .
C13 C 0.7457(2) 0.42194(16) 0.91537(13) 0.0194(3) Uani 1 1 d . . . . .
H13A H 0.7242 0.5329 0.8756 0.023 Uiso 1 1 calc R . . . .
H13B H 0.6129 0.3938 0.9524 0.023 Uiso 1 1 calc R . . . .
C14 C 0.8865(2) 0.35650(17) 1.02708(15) 0.0233(3) Uani 1 1 d . . . . .
H14 H 1.0270 0.3519 1.0030 0.028 Uiso 1 1 calc R . . . .
C15 C 0.8246(3) 0.30525(19) 1.15668(16) 0.0307(4) Uani 1 1 d . . . . .
H15A H 0.6852 0.3081 1.1844 0.037 Uiso 1 1 calc R . . . .
H15B H 0.9203 0.2663 1.2203 0.037 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3688(17) . ?
O1 C10 1.4303(18) . ?
N1 H1 0.8600 . ?
N1 C11 1.4787(16) . ?
N1 C12 1.3436(18) . ?
C1 C2 1.395(2) . ?
C1 C9 1.397(2) . ?
O2 C4 1.4291(16) . ?
O2 C12 1.3582(17) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(2) . ?
O3 C12 1.2266(18) . ?
C3 C4 1.4899(19) . ?
C3 C7 1.3996(19) . ?
C4 H4 0.9800 . ?
C4 C5 1.5306(18) . ?
C5 C6 1.5530(18) . ?
C5 C11 1.5228(19) . ?
C5 C13 1.5478(19) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.5299(19) . ?
C7 C8 1.384(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.407(2) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.5067(19) . ?
C14 H14 0.9300 . ?
C14 C15 1.319(2) . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C10 117.70(12) . . ?
C11 N1 H1 115.8 . . ?
C12 N1 H1 115.8 . . ?
C12 N1 C11 128.45(12) . . ?
O1 C1 C2 114.73(12) . . ?
O1 C1 C9 125.15(13) . . ?
C2 C1 C9 120.12(13) . . ?
C12 O2 C4 113.43(10) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.45(13) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 C4 129.35(12) . . ?
C2 C3 C7 122.97(13) . . ?
C7 C3 C4 107.45(12) . . ?
O2 C4 C3 115.59(11) . . ?
O2 C4 H4 107.8 . . ?
O2 C4 C5 112.59(10) . . ?
C3 C4 H4 107.8 . . ?
C3 C4 C5 104.80(11) . . ?
C5 C4 H4 107.8 . . ?
C4 C5 C6 100.36(10) . . ?
C4 C5 C13 112.49(11) . . ?
C11 C5 C4 103.06(11) . . ?
C11 C5 C6 120.48(11) . . ?
C11 C5 C13 110.43(11) . . ?
C13 C5 C6 109.41(11) . . ?
C5 C6 H6A 111.4 . . ?
C5 C6 H6B 111.4 . . ?
H6A C6 H6B 109.3 . . ?
C7 C6 C5 101.86(10) . . ?
C7 C6 H6A 111.4 . . ?
C7 C6 H6B 111.4 . . ?
C3 C7 C6 109.91(12) . . ?
C8 C7 C3 118.08(13) . . ?
C8 C7 C6 131.99(12) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.28(13) . . ?
C9 C8 H8 119.9 . . ?
C1 C9 C8 120.07(13) . . ?
C1 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C5 107.21(11) . . ?
N1 C11 H11A 110.3 . . ?
N1 C11 H11B 110.3 . . ?
C5 C11 H11A 110.3 . . ?
C5 C11 H11B 110.3 . . ?
H11A C11 H11B 108.5 . . ?
N1 C12 O2 118.52(12) . . ?
O3 C12 N1 124.20(13) . . ?
O3 C12 O2 117.27(12) . . ?
C5 C13 H13A 109.3 . . ?
C5 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 C5 111.46(12) . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 H14 117.7 . . ?
C15 C14 C13 124.59(14) . . ?
C15 C14 H14 117.7 . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?


_olex2_date_sample_data_collection 2017-06-02
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.230
_oxdiff_exptl_absorpt_empirical_full_min 0.864
####################################################################### 
# 
# 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_jml313_cu
_database_code_depnum_ccdc_archive 'CCDC 1566498'
_audit_update_record             
;
2017-08-03 deposited with the CCDC.
2017-11-02 downloaded from the CCDC.
;
_audit_creation_date             2016-11-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.24 svn.r3356 for OlexSys, GUI svn.r5267)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 (4aR*,7aS*)-4a-(Prop-2-en-1-yl)-hexahydro-2H-furo[3,4-e][1,3]oxazin-2-one
;
_chemical_formula_moiety         'C9 H13 N O3'
_chemical_formula_sum            'C9 H13 N O3'
_chemical_formula_weight         183.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C36 H52 N4 O12'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.65800(10)
_cell_length_b                   9.53160(10)
_cell_length_c                   12.1849(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.8050(10)
_cell_angle_gamma                90
_cell_volume                     886.29(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3539
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      73.4770
_cell_measurement_theta_min      3.6140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.859
_exptl_absorpt_correction_T_max  0.854
_exptl_absorpt_correction_T_min  0.776
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392.000
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 5 4 0.1450
-2 5 -3 0.1531
2 -5 3 0.1367
1 -4 -5 0.1196
0 -1 -8 0.1405
-5 0 0 0.2054
5 0 0 0.1049
-1 -5 5 0.1740
-4 3 -3 0.1487
2 -4 4 0.1292
-2 4 -4 0.1455
-1 -4 -6 0.1301
-2 -4 5 0.2105
-1 1 8 0.1476
-4 -3 -1 0.2096
0 -6 -2 0.1658
-2 -2 -6 0.1285
0 2 -7 0.1451
2 0 7 0.1312
3 3 5 0.1602
-3 2 -5 0.1248
2 -3 6 0.1201
4 1 2 0.1133
3 -4 -4 0.1276
3 -1 -7 0.1444

_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0000 5.0000 4.0000 0.3829 0.6900 0.6450
-2.0000 5.0000 -3.0000 0.4950 -0.1676 0.8455
2.0000 -5.0000 3.0000 -0.4950 0.1676 -0.8455
1.0000 -4.0000 -5.0000 -0.1567 -0.7690 -0.4722
0.0000 -1.0000 -8.0000 0.1193 -1.0178 0.0721
-5.0000 0.0000 -0.0000 1.0066 0.0295 -0.0642
5.0000 -0.0000 0.0000 -1.0066 -0.0295 0.0642
-1.0000 -5.0000 5.0000 0.0769 0.4303 -0.9413
-4.0000 3.0000 -3.0000 0.8799 -0.2311 0.5057
2.0000 -4.0000 4.0000 -0.5022 0.3277 -0.7171
-2.0000 4.0000 -4.0000 0.5022 -0.3277 0.7171
-1.0000 -4.0000 -6.0000 0.2620 -0.8797 -0.4692
-2.0000 -4.0000 5.0000 0.2871 0.4739 -0.7971
-1.0000 1.0000 8.0000 0.0820 1.0237 -0.0849
-4.0000 -3.0000 -1.0000 0.7947 -0.2118 -0.4939
-0.0000 -6.0000 -2.0000 -0.0211 -0.4708 -0.8850
-2.0000 -2.0000 -6.0000 0.4810 -0.7986 -0.1680
0.0000 2.0000 -7.0000 0.1299 -0.7823 0.5146
2.0000 -0.0000 7.0000 -0.5148 0.8458 -0.1748
3.0000 3.0000 5.0000 -0.6574 0.7078 0.3665
-3.0000 2.0000 -5.0000 0.7018 -0.5196 0.4187
2.0000 -3.0000 6.0000 -0.5253 0.6104 -0.6173
4.0000 1.0000 2.0000 -0.8284 0.2591 0.1512
3.0000 -4.0000 -4.0000 -0.5753 -0.6583 -0.4751
3.0000 -1.0000 -7.0000 -0.5007 -0.9129 0.0820

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0130
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4943
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.677
_diffrn_reflns_theta_min         5.798
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6191
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.9864
_diffrn_measured_fraction_theta_max 0.9593
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -18.00   1.00    1.00    --  -38.50 -37.00   0.00   92
  2  ω    -64.00  30.00   1.00    1.00    --  -38.50  57.00 150.00   94
  3  ω    -59.00  33.00   1.00    1.00    --  -38.50  37.00   0.00   92
  4  ω     35.00 127.00   1.00    1.00    --  104.98 -45.00  30.00   92
  5  ω     83.00 175.00   1.00    1.00    --  104.98  45.00 -60.00   92
  6  ω     65.00 178.00   1.00    1.00    --  104.98  15.00  60.00  113
  7  ω     36.00 132.00   1.00    1.00    --  104.98 -65.00 -15.93   96
  8  ω     36.00 132.00   1.00    1.00    --  104.98 -65.00  11.82   96
  9  ω     16.00 112.00   1.00    1.00    --   42.96  63.00 118.89   96
 10  ω     18.00 111.00   1.00    1.00    --   42.96  57.00-120.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2013103000
_diffrn_orient_matrix_UB_12      0.0088632000
_diffrn_orient_matrix_UB_13      -0.0160198000
_diffrn_orient_matrix_UB_21      -0.0058970000
_diffrn_orient_matrix_UB_22      0.0376299000
_diffrn_orient_matrix_UB_23      0.1225157000
_diffrn_orient_matrix_UB_31      0.0128488000
_diffrn_orient_matrix_UB_32      0.1570504000
_diffrn_orient_matrix_UB_33      -0.0286378000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1590
_reflns_number_total             1726
_reflns_odcompleteness_completeness 98.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         1726
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.072
_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)+(0.0381P)²+0.2977P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0817
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C8(H8)
2.d X=CH2 refined with riding coordinates:
 C9(H9A,H9B)
;
_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 0.02620(11) 0.64325(9) 0.09303(6) 0.0253(2) Uani 1 1 d . . . . .
N1 N 0.13613(11) 0.42438(10) 0.12413(7) 0.0193(2) Uani 1 1 d . . . . .
H1 H 0.1033 0.4021 0.0572 0.023 Uiso 1 1 calc R . . . .
C1 C 0.09278(13) 0.55344(12) 0.15530(8) 0.0189(2) Uani 1 1 d . . . . .
O2 O 0.12564(10) 0.58993(8) 0.26346(6) 0.0204(2) Uani 1 1 d . . . . .
C2 C 0.17252(14) 0.47420(12) 0.33494(8) 0.0196(2) Uani 1 1 d . . . . .
H2 H 0.0695 0.4143 0.3400 0.023 Uiso 1 1 calc R . . . .
O3 O 0.33830(12) 0.39012(9) 0.48708(6) 0.0272(2) Uani 1 1 d . . . . .
C3 C 0.31928(13) 0.38699(11) 0.29209(8) 0.0169(2) Uani 1 1 d . . . . .
C4 C 0.23331(14) 0.31535(11) 0.19021(8) 0.0191(2) Uani 1 1 d . . . . .
H4A H 0.3215 0.2728 0.1481 0.023 Uiso 1 1 calc R . . . .
H4B H 0.1539 0.2426 0.2110 0.023 Uiso 1 1 calc R . . . .
C5 C 0.24527(15) 0.51442(13) 0.44995(9) 0.0239(3) Uani 1 1 d . . . . .
H5A H 0.3235 0.5943 0.4485 0.029 Uiso 1 1 calc R . . . .
H5B H 0.1520 0.5362 0.4964 0.029 Uiso 1 1 calc R . . . .
C6 C 0.36350(15) 0.29823(12) 0.39473(9) 0.0224(3) Uani 1 1 d . . . . .
H6A H 0.2865 0.2175 0.3953 0.027 Uiso 1 1 calc R . . . .
H6B H 0.4838 0.2656 0.3976 0.027 Uiso 1 1 calc R . . . .
C7 C 0.47695(13) 0.47857(11) 0.26483(8) 0.0180(2) Uani 1 1 d . . . . .
H7A H 0.4377 0.5462 0.2086 0.022 Uiso 1 1 calc R . . . .
H7B H 0.5195 0.5303 0.3302 0.022 Uiso 1 1 calc R . . . .
C8 C 0.62486(14) 0.39471(12) 0.22522(10) 0.0248(3) Uani 1 1 d . . . . .
H8 H 0.6850 0.3346 0.2753 0.030 Uiso 1 1 calc R . . . .
C9 C 0.67592(16) 0.39989(13) 0.12480(11) 0.0314(3) Uani 1 1 d . . . . .
H9A H 0.6189 0.4588 0.0725 0.038 Uiso 1 1 calc R . . . .
H9B H 0.7690 0.3446 0.1061 0.038 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2262(14) . ?
N1 H1 0.8600 . ?
N1 C1 1.3375(14) . ?
N1 C4 1.4770(14) . ?
C1 O2 1.3659(12) . ?
O2 C2 1.4325(13) . ?
C2 H2 0.9800 . ?
C2 C3 1.5248(15) . ?
C2 C5 1.5134(14) . ?
O3 C5 1.4359(14) . ?
O3 C6 1.4516(14) . ?
C3 C4 1.5179(14) . ?
C3 C6 1.5243(14) . ?
C3 C7 1.5484(14) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.4988(15) . ?
C8 H8 0.9300 . ?
C8 C9 1.3163(18) . ?
C9 H9A 0.9300 . ?
C9 H9B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 115.9 . . ?
C1 N1 C4 128.17(9) . . ?
C4 N1 H1 115.9 . . ?
O1 C1 N1 124.51(10) . . ?
O1 C1 O2 116.92(10) . . ?
N1 C1 O2 118.56(9) . . ?
C1 O2 C2 114.03(8) . . ?
O2 C2 H2 109.0 . . ?
O2 C2 C3 111.46(8) . . ?
O2 C2 C5 114.96(9) . . ?
C3 C2 H2 109.0 . . ?
C5 C2 H2 109.0 . . ?
C5 C2 C3 103.32(9) . . ?
C5 O3 C6 110.38(8) . . ?
C2 C3 C7 112.12(9) . . ?
C4 C3 C2 104.10(8) . . ?
C4 C3 C6 118.21(9) . . ?
C4 C3 C7 111.76(8) . . ?
C6 C3 C2 98.11(8) . . ?
C6 C3 C7 111.42(8) . . ?
N1 C4 C3 107.07(8) . . ?
N1 C4 H4A 110.3 . . ?
N1 C4 H4B 110.3 . . ?
C3 C4 H4A 110.3 . . ?
C3 C4 H4B 110.3 . . ?
H4A C4 H4B 108.6 . . ?
C2 C5 H5A 111.3 . . ?
C2 C5 H5B 111.3 . . ?
O3 C5 C2 102.54(9) . . ?
O3 C5 H5A 111.3 . . ?
O3 C5 H5B 111.3 . . ?
H5A C5 H5B 109.2 . . ?
O3 C6 C3 105.44(9) . . ?
O3 C6 H6A 110.7 . . ?
O3 C6 H6B 110.7 . . ?
C3 C6 H6A 110.7 . . ?
C3 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
C3 C7 H7A 109.0 . . ?
C3 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C3 113.10(9) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C7 C8 H8 117.6 . . ?
C9 C8 C7 124.80(11) . . ?
C9 C8 H8 117.6 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?

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
O1 C1 O2 C2 169.03(9) . . . . ?
N1 C1 O2 C2 -11.60(13) . . . . ?
C1 N1 C4 C3 -14.84(14) . . . . ?
C1 O2 C2 C3 50.84(11) . . . . ?
C1 O2 C2 C5 167.98(9) . . . . ?
O2 C2 C3 C4 -69.94(10) . . . . ?
O2 C2 C3 C6 168.18(8) . . . . ?
O2 C2 C3 C7 51.04(11) . . . . ?
O2 C2 C5 O3 -159.29(8) . . . . ?
C2 C3 C4 N1 47.98(10) . . . . ?
C2 C3 C6 O3 -35.00(10) . . . . ?
C2 C3 C7 C8 178.55(9) . . . . ?
C3 C2 C5 O3 -37.62(10) . . . . ?
C3 C7 C8 C9 112.94(12) . . . . ?
C4 N1 C1 O1 172.80(10) . . . . ?
C4 N1 C1 O2 -6.51(16) . . . . ?
C4 C3 C6 O3 -145.84(9) . . . . ?
C4 C3 C7 C8 -65.00(12) . . . . ?
C5 C2 C3 C4 166.06(9) . . . . ?
C5 C2 C3 C6 44.18(10) . . . . ?
C5 C2 C3 C7 -72.96(11) . . . . ?
C5 O3 C6 C3 13.26(11) . . . . ?
C6 O3 C5 C2 15.02(11) . . . . ?
C6 C3 C4 N1 155.43(9) . . . . ?
C6 C3 C7 C8 69.70(12) . . . . ?
C7 C3 C4 N1 -73.23(10) . . . . ?
C7 C3 C6 O3 82.67(10) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_date_sample_data_collection 2016-11-28
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.169
_oxdiff_exptl_absorpt_empirical_full_min 0.686
