# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_dvd49
_database_code_depnum_ccdc_archive 'CCDC 1437633'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;
_audit_creation_date             2015-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 N O3'
_chemical_formula_sum            'C15 H19 N O3'
_chemical_formula_weight         261.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H19 N O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.6016(4)
_cell_length_b                   19.0377(7)
_cell_length_c                   11.3636(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.352(3)
_cell_angle_gamma                90
_cell_volume                     2681.80(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1978
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.8040
_cell_measurement_theta_min      3.2980
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97173
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11740
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.698
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -97.00  -62.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031 -178.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega  -36.00  -10.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031  -83.0000 -164.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -93.00    7.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031    0.0000 -180.0000 100
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0150428000
_diffrn_orient_matrix_UB_12      0.0081624000
_diffrn_orient_matrix_UB_13      0.0611158000
_diffrn_orient_matrix_UB_21      0.0237965000
_diffrn_orient_matrix_UB_22      0.0313658000
_diffrn_orient_matrix_UB_23      -0.0150990000
_diffrn_orient_matrix_UB_31      -0.0493938000
_diffrn_orient_matrix_UB_32      0.0176315000
_diffrn_orient_matrix_UB_33      -0.0015233000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4779
_reflns_number_total             6113
_reflns_odcompleteness_completeness 77.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         6113
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+0.8749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1264
_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:
 C1(H1), C2(H2), C1A(H1A), C2A(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B), C3A(H3AB,H3AC), C4A(H4AA,H4AB),
 C7A(H7AA,H7AB)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14), C10A(H10A), C11A(H11A), C13A(H13A),
 C14A(H14A)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C15(H15A,H15B,H15C), C8A(H8AA,H8AB,H8AC), C15A(H15D,H15E,H15F)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O3A(H3AA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.05543(8) 0.12281(6) 0.51275(10) 0.0218(3) Uani 1 1 d . . . . .
O2 O 0.82994(9) 0.29529(6) 0.07279(10) 0.0227(3) Uani 1 1 d . . . . .
O3 O 0.68916(8) 0.28739(6) 0.16806(10) 0.0201(3) Uani 1 1 d . . . . .
H3 H 0.6582 0.3096 0.1101 0.030 Uiso 1 1 calc GR . . . .
N1 N 0.91847(9) 0.12627(6) 0.35509(11) 0.0132(3) Uani 1 1 d . . . . .
C1 C 0.84039(10) 0.16246(8) 0.26230(13) 0.0123(3) Uani 1 1 d . . . . .
H1 H 0.7682 0.1524 0.2789 0.015 Uiso 1 1 calc R . . . .
C2 C 0.85583(11) 0.24339(8) 0.26985(13) 0.0135(3) Uani 1 1 d . . . . .
H2 H 0.8279 0.2604 0.3397 0.016 Uiso 1 1 calc R . . . .
C3 C 0.97528(11) 0.26130(8) 0.28697(14) 0.0162(3) Uani 1 1 d . . . . .
H3A H 0.9849 0.3118 0.2846 0.019 Uiso 1 1 calc R . . . .
H3B H 1.0071 0.2404 0.2236 0.019 Uiso 1 1 calc R . . . .
C4 C 1.02931(11) 0.23243(8) 0.40801(14) 0.0171(3) Uani 1 1 d . . . . .
H4A H 1.1069 0.2362 0.4144 0.021 Uiso 1 1 calc R . . . .
H4B H 1.0086 0.2613 0.4705 0.021 Uiso 1 1 calc R . . . .
C5 C 1.00113(11) 0.15702(8) 0.42893(13) 0.0155(3) Uani 1 1 d . . . . .
C6 C 0.79174(11) 0.27822(8) 0.15863(13) 0.0143(3) Uani 1 1 d . . . . .
C7 C 0.89488(12) 0.05139(8) 0.37379(14) 0.0167(3) Uani 1 1 d . . . . .
H7A H 0.9617 0.0273 0.4053 0.020 Uiso 1 1 calc R . . . .
H7B H 0.8651 0.0303 0.2973 0.020 Uiso 1 1 calc R . . . .
C8 C 0.81635(14) 0.04104(9) 0.45888(15) 0.0253(4) Uani 1 1 d . . . . .
H8A H 0.7490 0.0633 0.4267 0.038 Uiso 1 1 calc GR . . . .
H8B H 0.8456 0.0615 0.5350 0.038 Uiso 1 1 calc GR . . . .
H8C H 0.8047 -0.0083 0.4688 0.038 Uiso 1 1 calc GR . . . .
C9 C 0.84519(11) 0.13216(7) 0.13962(13) 0.0129(3) Uani 1 1 d . . . . .
C10 C 0.94212(11) 0.11017(8) 0.10819(13) 0.0155(3) Uani 1 1 d . . . . .
H10 H 1.0059 0.1134 0.1637 0.019 Uiso 1 1 calc R . . . .
C11 C 0.94423(12) 0.08342(8) -0.00540(14) 0.0180(3) Uani 1 1 d . . . . .
H11 H 1.0096 0.0695 -0.0250 0.022 Uiso 1 1 calc R . . . .
C12 C 0.84988(12) 0.07708(8) -0.09042(14) 0.0180(3) Uani 1 1 d . . . . .
C13 C 0.75320(12) 0.09963(8) -0.05908(14) 0.0194(3) Uani 1 1 d . . . . .
H13 H 0.6895 0.0968 -0.1148 0.023 Uiso 1 1 calc R . . . .
C14 C 0.75090(11) 0.12631(8) 0.05427(14) 0.0162(3) Uani 1 1 d . . . . .
H14 H 0.6855 0.1405 0.0736 0.019 Uiso 1 1 calc R . . . .
C15 C 0.85190(14) 0.04546(10) -0.21172(15) 0.0266(4) Uani 1 1 d . . . . .
H15A H 0.9215 0.0530 -0.2327 0.040 Uiso 1 1 calc GR . . . .
H15B H 0.7975 0.0673 -0.2703 0.040 Uiso 1 1 calc GR . . . .
H15C H 0.8380 -0.0041 -0.2094 0.040 Uiso 1 1 calc GR . . . .
O1A O 0.56227(8) 0.14519(6) 0.50077(10) 0.0191(2) Uani 1 1 d . . . . .
O2A O 0.30386(9) 0.30124(7) 0.05842(11) 0.0257(3) Uani 1 1 d . . . . .
O3A O 0.18265(8) 0.31060(7) 0.17940(10) 0.0222(3) Uani 1 1 d . . . . .
H3AA H 0.1473 0.3308 0.1216 0.033 Uiso 1 1 calc GR . . . .
N1A N 0.40960(9) 0.14714(6) 0.36272(11) 0.0126(3) Uani 1 1 d . . . . .
C1A C 0.33352(11) 0.17921(8) 0.26341(13) 0.0124(3) Uani 1 1 d . . . . .
H1A H 0.2607 0.1713 0.2798 0.015 Uiso 1 1 calc R . . . .
C2A C 0.35079(11) 0.25973(8) 0.26171(13) 0.0140(3) Uani 1 1 d . . . . .
H2A H 0.3314 0.2795 0.3346 0.017 Uiso 1 1 calc R . . . .
C3A C 0.46931(11) 0.27592(8) 0.26234(14) 0.0158(3) Uani 1 1 d . . . . .
H3AB H 0.4797 0.3262 0.2569 0.019 Uiso 1 1 calc R . . . .
H3AC H 0.4924 0.2538 0.1943 0.019 Uiso 1 1 calc R . . . .
C4A C 0.53553(11) 0.24782(8) 0.37858(14) 0.0170(3) Uani 1 1 d . . . . .
H4AA H 0.6106 0.2457 0.3696 0.020 Uiso 1 1 calc R . . . .
H4AB H 0.5305 0.2811 0.4420 0.020 Uiso 1 1 calc R . . . .
C5A C 0.50280(11) 0.17639(8) 0.41715(13) 0.0138(3) Uani 1 1 d . . . . .
C6A C 0.27784(11) 0.29261(8) 0.15473(14) 0.0150(3) Uani 1 1 d . . . . .
C7A C 0.37716(12) 0.07951(8) 0.40886(14) 0.0174(3) Uani 1 1 d . . . . .
H7AA H 0.2992 0.0755 0.3899 0.021 Uiso 1 1 calc R . . . .
H7AB H 0.3980 0.0792 0.4953 0.021 Uiso 1 1 calc R . . . .
C8A C 0.42685(13) 0.01624(8) 0.35824(15) 0.0233(4) Uani 1 1 d . . . . .
H8AA H 0.4011 0.0136 0.2736 0.035 Uiso 1 1 calc GR . . . .
H8AB H 0.4069 -0.0257 0.3957 0.035 Uiso 1 1 calc GR . . . .
H8AC H 0.5040 0.0208 0.3734 0.035 Uiso 1 1 calc GR . . . .
C9A C 0.33944(11) 0.14266(8) 0.14542(13) 0.0127(3) Uani 1 1 d . . . . .
C10A C 0.43708(11) 0.11944(8) 0.11713(13) 0.0151(3) Uani 1 1 d . . . . .
H10A H 0.5007 0.1257 0.1719 0.018 Uiso 1 1 calc R . . . .
C11A C 0.44010(11) 0.08708(8) 0.00789(14) 0.0163(3) Uani 1 1 d . . . . .
H11A H 0.5061 0.0726 -0.0095 0.020 Uiso 1 1 calc R . . . .
C12A C 0.34624(12) 0.07588(8) -0.07610(13) 0.0159(3) Uani 1 1 d . . . . .
C13A C 0.24866(12) 0.09938(8) -0.04748(14) 0.0179(3) Uani 1 1 d . . . . .
H13A H 0.1850 0.0932 -0.1022 0.021 Uiso 1 1 calc R . . . .
C14A C 0.24536(11) 0.13179(8) 0.06145(13) 0.0159(3) Uani 1 1 d . . . . .
H14A H 0.1795 0.1465 0.0787 0.019 Uiso 1 1 calc R . . . .
C15A C 0.35002(13) 0.03969(9) -0.19292(15) 0.0219(3) Uani 1 1 d . . . . .
H15D H 0.3336 -0.0092 -0.1862 0.033 Uiso 1 1 calc GR . . . .
H15E H 0.4208 0.0445 -0.2120 0.033 Uiso 1 1 calc GR . . . .
H15F H 0.2980 0.0607 -0.2551 0.033 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.2511(18) . ?
O2 C6 1.2074(18) . ?
O3 H3 0.8200 . ?
O3 C6 1.3276(17) . ?
N1 C1 1.4770(17) . ?
N1 C5 1.3482(18) . ?
N1 C7 1.4793(19) . ?
C1 H1 0.9800 . ?
C1 C2 1.553(2) . ?
C1 C9 1.520(2) . ?
C2 H2 0.9800 . ?
C2 C3 1.5214(19) . ?
C2 C6 1.524(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.523(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.508(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.516(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.397(2) . ?
C9 C14 1.3966(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.392(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.396(2) . ?
C12 C13 1.397(2) . ?
C12 C15 1.509(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.390(2) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O1A C5A 1.2495(18) . ?
O2A C6A 1.2088(19) . ?
O3A H3AA 0.8200 . ?
O3A C6A 1.3251(18) . ?
N1A C1A 1.4753(17) . ?
N1A C5A 1.3457(17) . ?
N1A C7A 1.4753(18) . ?
C1A H1A 0.9800 . ?
C1A C2A 1.549(2) . ?
C1A C9A 1.524(2) . ?
C2A H2A 0.9800 . ?
C2A C3A 1.5238(19) . ?
C2A C6A 1.521(2) . ?
C3A H3AB 0.9700 . ?
C3A H3AC 0.9700 . ?
C3A C4A 1.527(2) . ?
C4A H4AA 0.9700 . ?
C4A H4AB 0.9700 . ?
C4A C5A 1.509(2) . ?
C7A H7AA 0.9700 . ?
C7A H7AB 0.9700 . ?
C7A C8A 1.518(2) . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
C9A C10A 1.398(2) . ?
C9A C14A 1.3973(19) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.392(2) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.396(2) . ?
C12A C13A 1.401(2) . ?
C12A C15A 1.504(2) . ?
C13A H13A 0.9300 . ?
C13A C14A 1.390(2) . ?
C14A H14A 0.9300 . ?
C15A H15D 0.9600 . ?
C15A H15E 0.9600 . ?
C15A H15F 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
C6 O3 H3 109.5 . . ?
C1 N1 C7 115.25(11) . . ?
C5 N1 C1 125.65(12) . . ?
C5 N1 C7 118.80(12) . . ?
N1 C1 H1 107.1 . . ?
N1 C1 C2 111.25(11) . . ?
N1 C1 C9 110.28(11) . . ?
C2 C1 H1 107.1 . . ?
C9 C1 H1 107.1 . . ?
C9 C1 C2 113.69(12) . . ?
C1 C2 H2 108.3 . . ?
C3 C2 C1 109.90(11) . . ?
C3 C2 H2 108.3 . . ?
C3 C2 C6 111.92(12) . . ?
C6 C2 C1 110.08(11) . . ?
C6 C2 H2 108.3 . . ?
C2 C3 H3A 110.1 . . ?
C2 C3 H3B 110.1 . . ?
C2 C3 C4 107.82(12) . . ?
H3A C3 H3B 108.5 . . ?
C4 C3 H3A 110.1 . . ?
C4 C3 H3B 110.1 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 C3 113.96(12) . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
O1 C5 N1 120.23(14) . . ?
O1 C5 C4 120.24(13) . . ?
N1 C5 C4 119.52(13) . . ?
O2 C6 O3 124.41(14) . . ?
O2 C6 C2 123.94(13) . . ?
O3 C6 C2 111.65(12) . . ?
N1 C7 H7A 109.0 . . ?
N1 C7 H7B 109.0 . . ?
N1 C7 C8 112.83(13) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C1 121.93(12) . . ?
C14 C9 C1 119.88(12) . . ?
C14 C9 C10 118.19(14) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.65(13) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.16(14) . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 118.06(14) . . ?
C11 C12 C15 120.98(14) . . ?
C13 C12 C15 120.95(14) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.86(13) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.06(14) . . ?
C13 C14 H14 119.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6A O3A H3AA 109.5 . . ?
C1A N1A C7A 116.72(11) . . ?
C5A N1A C1A 125.02(12) . . ?
C5A N1A C7A 118.19(12) . . ?
N1A C1A H1A 107.0 . . ?
N1A C1A C2A 110.22(11) . . ?
N1A C1A C9A 110.86(11) . . ?
C2A C1A H1A 107.0 . . ?
C9A C1A H1A 107.0 . . ?
C9A C1A C2A 114.31(12) . . ?
C1A C2A H2A 108.2 . . ?
C3A C2A C1A 109.87(11) . . ?
C3A C2A H2A 108.2 . . ?
C6A C2A C1A 110.56(12) . . ?
C6A C2A H2A 108.2 . . ?
C6A C2A C3A 111.82(12) . . ?
C2A C3A H3AB 110.0 . . ?
C2A C3A H3AC 110.0 . . ?
C2A C3A C4A 108.42(12) . . ?
H3AB C3A H3AC 108.4 . . ?
C4A C3A H3AB 110.0 . . ?
C4A C3A H3AC 110.0 . . ?
C3A C4A H4AA 108.4 . . ?
C3A C4A H4AB 108.4 . . ?
H4AA C4A H4AB 107.4 . . ?
C5A C4A C3A 115.57(12) . . ?
C5A C4A H4AA 108.4 . . ?
C5A C4A H4AB 108.4 . . ?
O1A C5A N1A 120.50(13) . . ?
O1A C5A C4A 119.43(12) . . ?
N1A C5A C4A 120.07(12) . . ?
O2A C6A O3A 124.03(14) . . ?
O2A C6A C2A 123.80(13) . . ?
O3A C6A C2A 112.17(13) . . ?
N1A C7A H7AA 108.9 . . ?
N1A C7A H7AB 108.9 . . ?
N1A C7A C8A 113.48(12) . . ?
H7AA C7A H7AB 107.7 . . ?
C8A C7A H7AA 108.9 . . ?
C8A C7A H7AB 108.9 . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C10A C9A C1A 122.06(12) . . ?
C14A C9A C1A 119.91(12) . . ?
C14A C9A C10A 118.03(14) . . ?
C9A C10A H10A 119.6 . . ?
C11A C10A C9A 120.73(13) . . ?
C11A C10A H10A 119.6 . . ?
C10A C11A H11A 119.3 . . ?
C10A C11A C12A 121.43(13) . . ?
C12A C11A H11A 119.3 . . ?
C11A C12A C13A 117.63(14) . . ?
C11A C12A C15A 121.07(14) . . ?
C13A C12A C15A 121.31(13) . . ?
C12A C13A H13A 119.5 . . ?
C14A C13A C12A 121.09(13) . . ?
C14A C13A H13A 119.5 . . ?
C9A C14A H14A 119.5 . . ?
C13A C14A C9A 121.08(13) . . ?
C13A C14A H14A 119.5 . . ?
C12A C15A H15D 109.5 . . ?
C12A C15A H15E 109.5 . . ?
C12A C15A H15F 109.5 . . ?
H15D C15A H15E 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 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
N1 C1 C2 C3 44.32(16) . . . . ?
N1 C1 C2 C6 168.03(11) . . . . ?
N1 C1 C9 C10 -36.31(18) . . . . ?
N1 C1 C9 C14 144.28(13) . . . . ?
C1 N1 C5 O1 172.36(13) . . . . ?
C1 N1 C5 C4 -9.1(2) . . . . ?
C1 N1 C7 C8 -84.70(15) . . . . ?
C1 C2 C3 C4 -64.82(15) . . . . ?
C1 C2 C6 O2 -97.00(17) . . . . ?
C1 C2 C6 O3 83.05(15) . . . . ?
C1 C9 C10 C11 -179.20(13) . . . . ?
C1 C9 C14 C13 179.18(14) . . . . ?
C2 C1 C9 C10 89.43(16) . . . . ?
C2 C1 C9 C14 -89.98(16) . . . . ?
C2 C3 C4 C5 48.81(16) . . . . ?
C3 C2 C6 O2 25.5(2) . . . . ?
C3 C2 C6 O3 -154.42(13) . . . . ?
C3 C4 C5 O1 165.74(14) . . . . ?
C3 C4 C5 N1 -12.84(19) . . . . ?
C5 N1 C1 C2 -7.21(19) . . . . ?
C5 N1 C1 C9 119.90(15) . . . . ?
C5 N1 C7 C8 89.47(16) . . . . ?
C6 C2 C3 C4 172.55(12) . . . . ?
C7 N1 C1 C2 166.50(12) . . . . ?
C7 N1 C1 C9 -66.39(15) . . . . ?
C7 N1 C5 O1 -1.2(2) . . . . ?
C7 N1 C5 C4 177.43(13) . . . . ?
C9 C1 C2 C3 -80.91(14) . . . . ?
C9 C1 C2 C6 42.80(15) . . . . ?
C9 C10 C11 C12 -0.7(2) . . . . ?
C10 C9 C14 C13 -0.3(2) . . . . ?
C10 C11 C12 C13 1.2(2) . . . . ?
C10 C11 C12 C15 -177.59(15) . . . . ?
C11 C12 C13 C14 -1.2(2) . . . . ?
C12 C13 C14 C9 0.8(2) . . . . ?
C14 C9 C10 C11 0.2(2) . . . . ?
C15 C12 C13 C14 177.56(15) . . . . ?
N1A C1A C2A C3A 52.36(15) . . . . ?
N1A C1A C2A C6A 176.25(11) . . . . ?
N1A C1A C9A C10A -38.28(18) . . . . ?
N1A C1A C9A C14A 142.03(13) . . . . ?
C1A N1A C5A O1A -179.99(13) . . . . ?
C1A N1A C5A C4A 0.9(2) . . . . ?
C1A N1A C7A C8A 98.07(14) . . . . ?
C1A C2A C3A C4A -62.73(15) . . . . ?
C1A C2A C6A O2A -90.89(18) . . . . ?
C1A C2A C6A O3A 89.09(15) . . . . ?
C1A C9A C10A C11A -179.10(13) . . . . ?
C1A C9A C14A C13A 179.19(14) . . . . ?
C2A C1A C9A C10A 87.04(16) . . . . ?
C2A C1A C9A C14A -92.65(15) . . . . ?
C2A C3A C4A C5A 41.97(17) . . . . ?
C3A C2A C6A O2A 31.9(2) . . . . ?
C3A C2A C6A O3A -148.15(13) . . . . ?
C3A C4A C5A O1A 169.39(13) . . . . ?
C3A C4A C5A N1A -11.5(2) . . . . ?
C5A N1A C1A C2A -21.49(18) . . . . ?
C5A N1A C1A C9A 106.10(15) . . . . ?
C5A N1A C7A C8A -84.96(16) . . . . ?
C6A C2A C3A C4A 174.12(12) . . . . ?
C7A N1A C1A C2A 155.25(12) . . . . ?
C7A N1A C1A C9A -77.16(14) . . . . ?
C7A N1A C5A O1A 3.3(2) . . . . ?
C7A N1A C5A C4A -175.82(13) . . . . ?
C9A C1A C2A C3A -73.30(14) . . . . ?
C9A C1A C2A C6A 50.59(15) . . . . ?
C9A C10A C11A C12A -0.9(2) . . . . ?
C10A C9A C14A C13A -0.5(2) . . . . ?
C10A C11A C12A C13A 1.0(2) . . . . ?
C10A C11A C12A C15A -178.86(14) . . . . ?
C11A C12A C13A C14A -0.9(2) . . . . ?
C12A C13A C14A C9A 0.7(2) . . . . ?
C14A C9A C10A C11A 0.6(2) . . . . ?
C15A C12A C13A C14A 178.95(15) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_dvd73
_database_code_depnum_ccdc_archive 'CCDC 1438073'
_audit_update_record             
;
2015-11-20 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;
_audit_creation_date             2015-11-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H16 F N O3, C2 H3 N'
_chemical_formula_sum            'C16 H19 F N2 O3'
_chemical_formula_weight         306.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H19 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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6754(4)
_cell_length_b                   8.1698(2)
_cell_length_c                   17.8582(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.365(3)
_cell_angle_gamma                90
_cell_volume                     1557.49(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2025
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.3950
_cell_measurement_theta_min      3.1310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.306
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9759
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.742
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -95.00  -61.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2518  178.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   74.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -       21.1893    0.0000  150.0000 118

#__ type_ start__ end____ width___ exp.time_
  3 omega  -69.00   10.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2518  -77.0000   60.0000 79

#__ type_ start__ end____ width___ exp.time_
  4 omega  -73.00    8.00   1.0000  200.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.2518  -77.0000  -60.0000 81
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0132185000
_diffrn_orient_matrix_UB_12      -0.0285785000
_diffrn_orient_matrix_UB_13      -0.0367138000
_diffrn_orient_matrix_UB_21      0.0605491000
_diffrn_orient_matrix_UB_22      -0.0354589000
_diffrn_orient_matrix_UB_23      -0.0018217000
_diffrn_orient_matrix_UB_31      -0.0239338000
_diffrn_orient_matrix_UB_32      -0.0739271000
_diffrn_orient_matrix_UB_33      0.0150469000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2593
_reflns_number_total             3491
_reflns_odcompleteness_completeness 96.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3491
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      1.030
_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)+(0.0269P)²+0.5337P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0818
_refine_ls_wR_factor_ref         0.0912
_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:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C2S(H2SA,H2SB,H2SC)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F -0.01069(9) -0.31149(11) 0.51678(6) 0.0284(3) Uani 1 1 d . . . . .
O1 O 0.45286(11) 0.41685(12) 0.38087(7) 0.0223(3) Uani 1 1 d . . . . .
O2 O 0.50560(11) -0.19532(12) 0.43182(7) 0.0216(3) Uani 1 1 d . . . . .
O3 O 0.43592(11) -0.29292(12) 0.32173(6) 0.0210(3) Uani 1 1 d . . . . .
H3 H 0.4387 -0.3831 0.3443 0.031 Uiso 1 1 calc GR . . . .
N1 N 0.31538(12) 0.21758(14) 0.34253(7) 0.0153(3) Uani 1 1 d . . . . .
C1 C 0.31029(14) 0.04110(17) 0.32759(9) 0.0148(3) Uani 1 1 d . . . . .
H1 H 0.2801 0.0239 0.2751 0.018 Uiso 1 1 calc R . . . .
C2 C 0.45231(14) -0.00835(17) 0.33238(9) 0.0151(3) Uani 1 1 d . . . . .
H2 H 0.4864 -0.0135 0.2804 0.018 Uiso 1 1 calc R . . . .
C3 C 0.51650(15) 0.13192(17) 0.37391(10) 0.0175(3) Uani 1 1 d . . . . .
H3A H 0.5299 0.1040 0.4273 0.021 Uiso 1 1 calc R . . . .
H3B H 0.5983 0.1581 0.3510 0.021 Uiso 1 1 calc R . . . .
C4 C 0.42689(15) 0.27304(17) 0.36585(9) 0.0161(3) Uani 1 1 d . . . . .
C5 C 0.46889(14) -0.17362(17) 0.36848(9) 0.0146(3) Uani 1 1 d . . . . .
C6 C 0.20251(15) 0.31922(18) 0.33733(10) 0.0203(4) Uani 1 1 d . . . . .
H6A H 0.2253 0.4342 0.3483 0.024 Uiso 1 1 calc R . . . .
H6B H 0.1423 0.2831 0.3759 0.024 Uiso 1 1 calc R . . . .
C7 C 0.13917(15) 0.3116(2) 0.26107(10) 0.0221(4) Uani 1 1 d . . . . .
H7A H 0.1129 0.1974 0.2510 0.026 Uiso 1 1 calc R . . . .
H7B H 0.0628 0.3803 0.2619 0.026 Uiso 1 1 calc R . . . .
C8 C 0.22303(17) 0.3690(3) 0.19833(11) 0.0362(5) Uani 1 1 d . . . . .
H8A H 0.1776 0.3615 0.1506 0.054 Uiso 1 1 calc GR . . . .
H8B H 0.2980 0.2998 0.1965 0.054 Uiso 1 1 calc GR . . . .
H8C H 0.2478 0.4828 0.2073 0.054 Uiso 1 1 calc GR . . . .
C9 C 0.22387(14) -0.04930(17) 0.38029(9) 0.0151(3) Uani 1 1 d . . . . .
C10 C 0.14772(14) -0.17220(18) 0.35096(10) 0.0179(4) Uani 1 1 d . . . . .
H10 H 0.1496 -0.1947 0.2988 0.021 Uiso 1 1 calc R . . . .
C11 C 0.06904(15) -0.26232(19) 0.39691(10) 0.0204(4) Uani 1 1 d . . . . .
H11 H 0.0177 -0.3470 0.3771 0.024 Uiso 1 1 calc R . . . .
C12 C 0.06787(15) -0.22535(19) 0.47155(10) 0.0194(4) Uani 1 1 d . . . . .
C13 C 0.14163(15) -0.10539(18) 0.50316(10) 0.0208(4) Uani 1 1 d . . . . .
H13 H 0.1385 -0.0835 0.5554 0.025 Uiso 1 1 calc R . . . .
C14 C 0.22061(15) -0.01734(18) 0.45677(9) 0.0181(4) Uani 1 1 d . . . . .
H14 H 0.2729 0.0655 0.4774 0.022 Uiso 1 1 calc R . . . .
N1S N 0.80898(15) 0.4177(2) 0.34620(9) 0.0355(4) Uani 1 1 d . . . . .
C1S C 0.76133(16) 0.4519(2) 0.40101(11) 0.0234(4) Uani 1 1 d . . . . .
C2S C 0.70302(16) 0.4959(2) 0.47172(10) 0.0254(4) Uani 1 1 d . . . . .
H2SA H 0.7673 0.5355 0.5067 0.038 Uiso 1 1 calc GR . . . .
H2SB H 0.6617 0.3995 0.4930 0.038 Uiso 1 1 calc GR . . . .
H2SC H 0.6409 0.5822 0.4631 0.038 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
F1 C12 1.3636(18) . ?
O1 C4 1.2362(17) . ?
O2 C5 1.2078(19) . ?
O3 H3 0.8400 . ?
O3 C5 1.3293(18) . ?
N1 C1 1.4671(18) . ?
N1 C4 1.338(2) . ?
N1 C6 1.4659(19) . ?
C1 H1 1.0000 . ?
C1 C2 1.571(2) . ?
C1 C9 1.514(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.525(2) . ?
C2 C5 1.506(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.504(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.518(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.513(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.392(2) . ?
C9 C14 1.391(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.389(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.367(2) . ?
C12 C13 1.376(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.387(2) . ?
C14 H14 0.9500 . ?
N1S C1S 1.141(2) . ?
C1S C2S 1.456(3) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 O3 H3 109.5 . . ?
C4 N1 C1 114.92(12) . . ?
C4 N1 C6 123.87(12) . . ?
C6 N1 C1 121.05(13) . . ?
N1 C1 H1 108.7 . . ?
N1 C1 C2 102.02(12) . . ?
N1 C1 C9 112.85(12) . . ?
C2 C1 H1 108.7 . . ?
C9 C1 H1 108.7 . . ?
C9 C1 C2 115.62(12) . . ?
C1 C2 H2 108.5 . . ?
C3 C2 C1 105.28(12) . . ?
C3 C2 H2 108.5 . . ?
C5 C2 C1 111.38(12) . . ?
C5 C2 H2 108.5 . . ?
C5 C2 C3 114.47(13) . . ?
C2 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C4 C3 C2 104.24(13) . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
O1 C4 N1 125.97(14) . . ?
O1 C4 C3 124.48(15) . . ?
N1 C4 C3 109.52(12) . . ?
O2 C5 O3 124.30(13) . . ?
O2 C5 C2 124.68(14) . . ?
O3 C5 C2 111.01(13) . . ?
N1 C6 H6A 108.9 . . ?
N1 C6 H6B 108.9 . . ?
N1 C6 C7 113.25(13) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 112.91(14) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C1 118.33(14) . . ?
C14 C9 C1 122.53(14) . . ?
C14 C9 C10 119.11(14) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 120.92(16) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 121.0 . . ?
C12 C11 C10 117.92(15) . . ?
C12 C11 H11 121.0 . . ?
F1 C12 C11 118.23(14) . . ?
F1 C12 C13 118.49(15) . . ?
C11 C12 C13 123.28(15) . . ?
C12 C13 H13 120.9 . . ?
C12 C13 C14 118.22(16) . . ?
C14 C13 H13 120.9 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.55(15) . . ?
C13 C14 H14 119.7 . . ?
N1S C1S C2S 178.83(19) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 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
F1 C12 C13 C14 -179.50(14) . . . . ?
N1 C1 C2 C3 17.93(15) . . . . ?
N1 C1 C2 C5 142.55(13) . . . . ?
N1 C1 C9 C10 139.17(14) . . . . ?
N1 C1 C9 C14 -42.7(2) . . . . ?
N1 C6 C7 C8 -60.16(18) . . . . ?
C1 N1 C4 O1 179.17(15) . . . . ?
C1 N1 C4 C3 -2.83(19) . . . . ?
C1 N1 C6 C7 -57.49(19) . . . . ?
C1 C2 C3 C4 -19.74(16) . . . . ?
C1 C2 C5 O2 -104.26(17) . . . . ?
C1 C2 C5 O3 74.80(16) . . . . ?
C1 C9 C10 C11 178.24(14) . . . . ?
C1 C9 C14 C13 -178.76(14) . . . . ?
C2 C1 C9 C10 -103.92(16) . . . . ?
C2 C1 C9 C14 74.17(18) . . . . ?
C2 C3 C4 O1 -167.39(15) . . . . ?
C2 C3 C4 N1 14.57(17) . . . . ?
C3 C2 C5 O2 15.0(2) . . . . ?
C3 C2 C5 O3 -165.91(13) . . . . ?
C4 N1 C1 C2 -9.76(17) . . . . ?
C4 N1 C1 C9 114.95(15) . . . . ?
C4 N1 C6 C7 127.44(15) . . . . ?
C5 C2 C3 C4 -142.40(13) . . . . ?
C6 N1 C1 C2 174.76(13) . . . . ?
C6 N1 C1 C9 -60.54(19) . . . . ?
C6 N1 C4 O1 -5.5(3) . . . . ?
C6 N1 C4 C3 172.51(14) . . . . ?
C9 C1 C2 C3 -104.91(15) . . . . ?
C9 C1 C2 C5 19.71(18) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C10 C9 C14 C13 -0.7(2) . . . . ?
C10 C11 C12 F1 178.92(13) . . . . ?
C10 C11 C12 C13 -0.9(2) . . . . ?
C11 C12 C13 C14 0.3(2) . . . . ?
C12 C13 C14 C9 0.5(2) . . . . ?
C14 C9 C10 C11 0.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_dvd-73
_database_code_depnum_ccdc_archive 'CCDC 1442357'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;
_audit_creation_date             2015-12-14
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H16 F N O3'
_chemical_formula_sum            'C14 H16 F N O3'
_chemical_formula_weight         265.28
_chemical_melting_point          ?
_chemical_oxdiff_formula         'O3 C12 H20'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 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                   9.9465(16)
_cell_length_b                   15.9223(18)
_cell_length_c                   8.4185(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.142(11)
_cell_angle_gamma                90.00
_cell_volume                     1332.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1539
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3750
_cell_measurement_theta_min      3.5210
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6163
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.28
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9783
_diffrn_measured_fraction_theta_max 0.9783
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    2.00   95.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4968   38.0000 -150.0000 93

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00   64.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4968  -99.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega   39.00   68.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4968  178.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega  -47.00   28.00   1.0000   23.0000
omega____ theta____ kappa____ phi______ frames
    -       23.4968  -77.0000  -90.0000 75
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0520354000
_diffrn_orient_matrix_UB_12      -0.0037319000
_diffrn_orient_matrix_UB_13      -0.0547970000
_diffrn_orient_matrix_UB_21      0.0479973000
_diffrn_orient_matrix_UB_22      -0.0048914000
_diffrn_orient_matrix_UB_23      0.0637695000
_diffrn_orient_matrix_UB_31      -0.0096950000
_diffrn_orient_matrix_UB_32      -0.0441748000
_diffrn_orient_matrix_UB_33      -0.0022631000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2327
_reflns_number_total             3007
_reflns_odcompleteness_completeness 97.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3007
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0597
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.039
_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)+(0.0429P)²+0.3867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0947
_refine_ls_wR_factor_ref         0.1077
_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. 
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 1.16613(9) 0.67426(7) 0.43887(11) 0.0327(3) Uani 1 1 d . . .
O1 O 0.44291(11) 0.46031(6) 0.69834(12) 0.0223(3) Uani 1 1 d . . .
N1 N 0.62725(12) 0.54644(7) 0.73128(14) 0.0172(3) Uani 1 1 d . . .
O3 O 0.59174(12) 0.81851(7) 0.64063(14) 0.0281(3) Uani 1 1 d . . .
H3 H 0.5702 0.8634 0.6802 0.042 Uiso 1 1 calc R . .
C3 C 0.42995(15) 0.60911(9) 0.63231(18) 0.0194(3) Uani 1 1 d . . .
H3A H 0.3646 0.6277 0.7075 0.023 Uiso 1 1 calc R . .
H3B H 0.3843 0.6002 0.5298 0.023 Uiso 1 1 calc R . .
C8 C 0.50499(15) 0.75938(9) 0.68036(17) 0.0189(3) Uani 1 1 d . . .
C13 C 0.95063(16) 0.61314(10) 0.43341(18) 0.0241(3) Uani 1 1 d . . .
H13 H 0.9695 0.5850 0.3400 0.029 Uiso 1 1 calc R . .
O2 O 0.40949(12) 0.77279(7) 0.76129(15) 0.0323(3) Uani 1 1 d . . .
C4 C 0.49841(15) 0.52982(9) 0.68953(16) 0.0177(3) Uani 1 1 d . . .
C14 C 0.82656(15) 0.60432(10) 0.50158(18) 0.0211(3) Uani 1 1 d . . .
H14 H 0.7610 0.5702 0.4533 0.025 Uiso 1 1 calc R . .
C5 C 0.71938(15) 0.48368(9) 0.80075(17) 0.0202(3) Uani 1 1 d . . .
H5A H 0.8043 0.4867 0.7480 0.024 Uiso 1 1 calc R . .
H5B H 0.6820 0.4282 0.7817 0.024 Uiso 1 1 calc R . .
C12 C 1.04530(15) 0.66462(10) 0.50763(18) 0.0231(3) Uani 1 1 d . . .
C1 C 0.66487(14) 0.63571(9) 0.71781(16) 0.0169(3) Uani 1 1 d . . .
H1 H 0.6689 0.6611 0.8239 0.020 Uiso 1 1 calc R . .
C2 C 0.54252(14) 0.67349(9) 0.61911(16) 0.0170(3) Uani 1 1 d . . .
H2 H 0.5664 0.6783 0.5076 0.020 Uiso 1 1 calc R . .
C10 C 0.89843(15) 0.69700(10) 0.71423(18) 0.0219(3) Uani 1 1 d . . .
H10 H 0.8812 0.7244 0.8089 0.026 Uiso 1 1 calc R . .
C11 C 1.02291(16) 0.70713(10) 0.64593(19) 0.0250(4) Uani 1 1 d . . .
H11 H 1.0887 0.7416 0.6926 0.030 Uiso 1 1 calc R . .
C7 C 0.8394(2) 0.42782(12) 1.0467(2) 0.0377(4) Uani 1 1 d . . .
H7A H 0.8557 0.4377 1.1582 0.056 Uiso 1 1 calc R . .
H7B H 0.9231 0.4296 0.9935 0.056 Uiso 1 1 calc R . .
H7C H 0.7986 0.3736 1.0315 0.056 Uiso 1 1 calc R . .
C9 C 0.79963(14) 0.64641(9) 0.64249(17) 0.0180(3) Uani 1 1 d . . .
C6 C 0.74527(19) 0.49546(11) 0.97798(19) 0.0317(4) Uani 1 1 d . . .
H6A H 0.6605 0.4933 1.0312 0.038 Uiso 1 1 calc R . .
H6B H 0.7849 0.5503 0.9975 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
F1 C12 1.3621(17) . ?
O1 C4 1.2402(18) . ?
N1 C4 1.3425(19) . ?
N1 C5 1.4630(18) . ?
N1 C1 1.4752(18) . ?
O3 H3 0.8200 . ?
O3 C8 1.3283(18) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.505(2) . ?
C3 C2 1.525(2) . ?
C8 O2 1.2085(18) . ?
C8 C2 1.513(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.387(2) . ?
C13 C12 1.380(2) . ?
C14 H14 0.9300 . ?
C14 C9 1.397(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.516(2) . ?
C12 C11 1.372(2) . ?
C1 H1 0.9800 . ?
C1 C2 1.5677(19) . ?
C1 C9 1.514(2) . ?
C2 H2 0.9800 . ?
C10 H10 0.9300 . ?
C10 C11 1.394(2) . ?
C10 C9 1.391(2) . ?
C11 H11 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7 C6 1.527(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 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
C4 N1 C5 123.19(12) . . ?
C4 N1 C1 114.35(12) . . ?
C5 N1 C1 122.14(12) . . ?
C8 O3 H3 109.5 . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
C4 C3 C2 105.22(12) . . ?
C2 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
O3 C8 C2 112.58(12) . . ?
O2 C8 O3 123.26(14) . . ?
O2 C8 C2 124.11(14) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C12 C13 C14 118.37(14) . . ?
O1 C4 N1 125.66(14) . . ?
O1 C4 C3 124.79(14) . . ?
N1 C4 C3 109.54(12) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C9 120.29(14) . . ?
C9 C14 H14 119.9 . . ?
N1 C5 H5A 109.0 . . ?
N1 C5 H5B 109.0 . . ?
N1 C5 C6 112.94(12) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
F1 C12 C13 118.19(14) . . ?
F1 C12 C11 118.61(14) . . ?
C11 C12 C13 123.20(14) . . ?
N1 C1 H1 109.2 . . ?
N1 C1 C2 102.49(11) . . ?
N1 C1 C9 111.83(11) . . ?
C2 C1 H1 109.2 . . ?
C9 C1 H1 109.2 . . ?
C9 C1 C2 114.63(11) . . ?
C3 C2 C1 105.13(11) . . ?
C3 C2 H2 109.1 . . ?
C8 C2 C3 113.05(12) . . ?
C8 C2 C1 111.26(11) . . ?
C8 C2 H2 109.1 . . ?
C1 C2 H2 109.1 . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.79(14) . . ?
C12 C11 C10 117.89(14) . . ?
C12 C11 H11 121.1 . . ?
C10 C11 H11 121.1 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
C14 C9 C1 120.17(13) . . ?
C10 C9 C14 119.45(14) . . ?
C10 C9 C1 120.37(13) . . ?
C5 C6 C7 111.39(14) . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?

####################################################################### 
# 
# 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_dvd-34
_database_code_depnum_ccdc_archive 'CCDC 1442376'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;
_audit_creation_date             2015-12-14
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C16 H21 N O4'
_chemical_formula_sum            'C16 H21 N O4'
_chemical_formula_weight         291.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'O3 C12 H20'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.4049(2)
_cell_length_b                   21.3010(6)
_cell_length_c                   10.8631(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.374(3)
_cell_angle_gamma                90.00
_cell_volume                     1457.85(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8007
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.8240
_cell_measurement_theta_min      3.3270
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23949
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.70
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9991
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -42.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031  178.0000 -120.0000 60

#__ type_ start__ end____ width___ exp.time_
  2 omega    4.00   72.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   38.0000  -90.0000 68

#__ type_ start__ end____ width___ exp.time_
  3 omega   28.00   69.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968 -108.0000  162.0000 41

#__ type_ start__ end____ width___ exp.time_
  4 omega  -25.00   68.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -99.0000  -90.0000 93

#__ type_ start__ end____ width___ exp.time_
  5 omega   -4.00   64.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   77.0000  150.0000 68

#__ type_ start__ end____ width___ exp.time_
  6 omega   -3.00   88.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   77.0000  -90.0000 91

#__ type_ start__ end____ width___ exp.time_
  7 omega   -4.00   97.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   77.0000   30.0000 101

#__ type_ start__ end____ width___ exp.time_
  8 omega  -16.00   99.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968    0.0000 -150.0000 115

#__ type_ start__ end____ width___ exp.time_
  9 omega  -25.00   68.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -99.0000   90.0000 93

#__ type_ start__ end____ width___ exp.time_
 10 omega  -44.00   70.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -19.0000   90.0000 114
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0514484000
_diffrn_orient_matrix_UB_12      -0.0276806000
_diffrn_orient_matrix_UB_13      -0.0152881000
_diffrn_orient_matrix_UB_21      -0.0416929000
_diffrn_orient_matrix_UB_22      -0.0167377000
_diffrn_orient_matrix_UB_23      0.0465776000
_diffrn_orient_matrix_UB_31      -0.0910838000
_diffrn_orient_matrix_UB_32      -0.0079437000
_diffrn_orient_matrix_UB_33      -0.0446937000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2959
_reflns_number_total             3349
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0732P)²+0.7915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1302
_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. 
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O3 O 0.28271(16) 0.28962(5) 0.46178(9) 0.0188(2) Uani 1 1 d . . .
H3 H 0.2104 0.3076 0.4022 0.028 Uiso 1 1 calc R . .
O1 O 1.02178(16) 0.14631(5) 0.80065(9) 0.0176(2) Uani 1 1 d . . .
O2 O 0.53492(17) 0.29685(5) 0.34377(10) 0.0233(3) Uani 1 1 d . . .
N1 N 0.73092(17) 0.14760(5) 0.64815(10) 0.0120(2) Uani 1 1 d . . .
C1 C 0.5851(2) 0.17836(6) 0.54538(12) 0.0120(3) Uani 1 1 d . . .
H1 H 0.4408 0.1712 0.5606 0.014 Uiso 1 1 calc R . .
C10 C 0.5975(2) 0.14876(6) 0.41895(12) 0.0135(3) Uani 1 1 d . . .
O4 O 0.59565(19) 0.06797(5) 0.06796(10) 0.0245(3) Uani 1 1 d . . .
C2 C 0.6217(2) 0.25023(6) 0.54919(12) 0.0126(3) Uani 1 1 d . . .
H2 H 0.5839 0.2663 0.6268 0.015 Uiso 1 1 calc R . .
C9 C 0.4778(2) 0.28184(6) 0.43982(13) 0.0140(3) Uani 1 1 d . . .
C5 C 0.9099(2) 0.17413(6) 0.71066(12) 0.0134(3) Uani 1 1 d . . .
C4 C 0.9791(2) 0.23834(7) 0.67353(13) 0.0159(3) Uani 1 1 d . . .
H4A H 1.1277 0.2361 0.6665 0.019 Uiso 1 1 calc R . .
H4B H 0.9673 0.2676 0.7403 0.019 Uiso 1 1 calc R . .
C11 C 0.7862(2) 0.12630(6) 0.38906(13) 0.0160(3) Uani 1 1 d . . .
H11 H 0.9106 0.1293 0.4481 0.019 Uiso 1 1 calc R . .
C12 C 0.7937(2) 0.09932(7) 0.27252(13) 0.0180(3) Uani 1 1 d . . .
H12 H 0.9215 0.0846 0.2544 0.022 Uiso 1 1 calc R . .
C3 C 0.8550(2) 0.26456(6) 0.55170(13) 0.0147(3) Uani 1 1 d . . .
H3A H 0.8766 0.3095 0.5476 0.018 Uiso 1 1 calc R . .
H3B H 0.9021 0.2451 0.4807 0.018 Uiso 1 1 calc R . .
C6 C 0.6725(2) 0.08529(6) 0.69455(13) 0.0159(3) Uani 1 1 d . . .
H6 H 0.7155 0.0858 0.7858 0.019 Uiso 1 1 calc R . .
C15 C 0.4132(2) 0.14414(6) 0.32777(13) 0.0162(3) Uani 1 1 d . . .
H15 H 0.2854 0.1590 0.3455 0.019 Uiso 1 1 calc R . .
C13 C 0.6081(2) 0.09468(6) 0.18387(13) 0.0181(3) Uani 1 1 d . . .
C14 C 0.4177(2) 0.11774(7) 0.21134(13) 0.0188(3) Uani 1 1 d . . .
H14 H 0.2940 0.1154 0.1518 0.023 Uiso 1 1 calc R . .
C8 C 0.7976(3) 0.03272(7) 0.64550(16) 0.0247(3) Uani 1 1 d . . .
H8A H 0.7552 0.0295 0.5564 0.037 Uiso 1 1 calc R . .
H8B H 0.7697 -0.0063 0.6837 0.037 Uiso 1 1 calc R . .
H8C H 0.9466 0.0419 0.6656 0.037 Uiso 1 1 calc R . .
C16 C 0.7807(3) 0.03617(8) 0.04254(15) 0.0271(3) Uani 1 1 d . . .
H16A H 0.7459 0.0140 -0.0354 0.041 Uiso 1 1 calc R . .
H16B H 0.8297 0.0069 0.1086 0.041 Uiso 1 1 calc R . .
H16C H 0.8903 0.0663 0.0375 0.041 Uiso 1 1 calc R . .
C7 C 0.4346(2) 0.07223(7) 0.66683(15) 0.0206(3) Uani 1 1 d . . .
H7A H 0.3611 0.1048 0.7029 0.031 Uiso 1 1 calc R . .
H7B H 0.4067 0.0325 0.7022 0.031 Uiso 1 1 calc R . .
H7C H 0.3861 0.0712 0.5779 0.031 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
O3 C9 1.3238(17) . ?
O1 C5 1.2522(17) . ?
O2 C9 1.2094(17) . ?
N1 C1 1.4738(16) . ?
N1 C5 1.3470(17) . ?
N1 C6 1.4912(16) . ?
C1 C10 1.5263(18) . ?
C1 C2 1.5481(18) . ?
C10 C11 1.3918(19) . ?
C10 C15 1.4010(19) . ?
O4 C13 1.3709(17) . ?
O4 C16 1.434(2) . ?
C2 C9 1.5232(18) . ?
C2 C3 1.5205(18) . ?
C5 C4 1.5146(19) . ?
C4 C3 1.5219(19) . ?
C11 C12 1.3989(19) . ?
C12 C13 1.392(2) . ?
C6 C8 1.528(2) . ?
C6 C7 1.5246(19) . ?
C15 C14 1.389(2) . ?
C13 C14 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
C1 N1 C6 119.23(10) . . ?
C5 N1 C1 124.12(11) . . ?
C5 N1 C6 116.47(11) . . ?
N1 C1 C10 111.69(10) . . ?
N1 C1 C2 110.32(10) . . ?
C10 C1 C2 113.61(11) . . ?
C11 C10 C1 122.68(12) . . ?
C11 C10 C15 117.87(12) . . ?
C15 C10 C1 119.45(12) . . ?
C13 O4 C16 117.34(12) . . ?
C9 C2 C1 110.43(10) . . ?
C3 C2 C1 110.02(10) . . ?
C3 C2 C9 112.33(11) . . ?
O3 C9 C2 111.90(11) . . ?
O2 C9 O3 124.36(13) . . ?
O2 C9 C2 123.72(12) . . ?
O1 C5 N1 120.69(12) . . ?
O1 C5 C4 118.79(12) . . ?
N1 C5 C4 120.52(12) . . ?
C5 C4 C3 115.52(11) . . ?
C10 C11 C12 121.65(13) . . ?
C13 C12 C11 119.44(13) . . ?
C2 C3 C4 107.44(11) . . ?
N1 C6 C8 110.80(12) . . ?
N1 C6 C7 113.48(11) . . ?
C7 C6 C8 111.45(12) . . ?
C14 C15 C10 121.28(13) . . ?
O4 C13 C12 124.50(14) . . ?
O4 C13 C14 115.70(13) . . ?
C12 C13 C14 119.80(13) . . ?
C15 C14 C13 119.94(13) . . ?

####################################################################### 
# 
# 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_exp_2139
_database_code_depnum_ccdc_archive 'CCDC 1442379'
_audit_update_record             
;
2015-12-14 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;
_audit_creation_date             2015-12-14
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H21 N O4'
_chemical_formula_sum            'C20 H21 N O4'
_chemical_formula_weight         339.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cu I C20 O2 H26'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.3469(6)
_cell_length_b                   27.815(3)
_cell_length_c                   10.8960(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.887(11)
_cell_angle_gamma                90.00
_cell_volume                     1895.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2006
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.6810
_cell_measurement_theta_min      2.9190
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.0555
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4297
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.90
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9810
_diffrn_measured_fraction_theta_max 0.8527
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -60.00    9.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031    0.0000   60.0000 69

#__ type_ start__ end____ width___ exp.time_
  2 omega  -72.00   -7.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031  -57.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  3 omega -101.00  -62.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031 -178.0000   60.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega   36.00   86.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  178.0000    0.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0531565000
_diffrn_orient_matrix_UB_12      0.0203891000
_diffrn_orient_matrix_UB_13      -0.0189558000
_diffrn_orient_matrix_UB_21      -0.0038697000
_diffrn_orient_matrix_UB_22      -0.0103879000
_diffrn_orient_matrix_UB_23      -0.0599442000
_diffrn_orient_matrix_UB_31      -0.1000505000
_diffrn_orient_matrix_UB_32      0.0112008000
_diffrn_orient_matrix_UB_33      -0.0207359000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3395
_reflns_number_total             4297
_reflns_odcompleteness_completeness 98.10
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0549
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0892P)²+0.3311P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1492
_refine_ls_wR_factor_ref         0.1652
_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. 
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O -0.07579(18) 0.22175(4) 0.62301(11) 0.0182(3) Uani 1 1 d . . .
H4 H -0.1418 0.2053 0.5668 0.027 Uiso 1 1 calc R . .
O1 O 0.68166(18) 0.33189(4) 0.95973(11) 0.0189(3) Uani 1 1 d . . .
O3 O 0.18480(19) 0.21697(4) 0.50731(11) 0.0200(3) Uani 1 1 d . . .
O2 O 0.1964(2) 0.52408(4) 0.88893(13) 0.0249(3) Uani 1 1 d . . .
N1 N 0.3916(2) 0.33175(5) 0.80518(12) 0.0118(3) Uani 1 1 d . . .
C5 C 0.5655(2) 0.31024(6) 0.87324(15) 0.0133(3) Uani 1 1 d . . .
C6 C 0.1226(2) 0.22871(6) 0.60263(15) 0.0134(3) Uani 1 1 d . . .
C1 C 0.2285(2) 0.30777(6) 0.71088(14) 0.0128(3) Uani 1 1 d . . .
H1 H 0.0887 0.3139 0.7343 0.015 Uiso 1 1 calc R . .
C14 C 0.2243(2) 0.32986(6) 0.58174(15) 0.0134(3) Uani 1 1 d . . .
C7 C 0.3479(2) 0.38163(6) 0.82878(15) 0.0133(3) Uani 1 1 d . . .
C2 C 0.2627(2) 0.25235(6) 0.71410(15) 0.0135(4) Uani 1 1 d . . .
H2 H 0.2198 0.2399 0.7902 0.016 Uiso 1 1 calc R . .
C8 C 0.1626(3) 0.39375(6) 0.87522(15) 0.0149(4) Uani 1 1 d . . .
H8 H 0.0709 0.3698 0.8939 0.018 Uiso 1 1 calc R . .
C4 C 0.6196(3) 0.25925(6) 0.84193(16) 0.0156(4) Uani 1 1 d . . .
H4A H 0.5905 0.2382 0.9080 0.019 Uiso 1 1 calc R . .
H4B H 0.7716 0.2574 0.8399 0.019 Uiso 1 1 calc R . .
C3 C 0.4975(3) 0.24072(6) 0.71833(15) 0.0152(4) Uani 1 1 d . . .
H3A H 0.5495 0.2561 0.6495 0.018 Uiso 1 1 calc R . .
H3B H 0.5170 0.2063 0.7120 0.018 Uiso 1 1 calc R . .
C19 C 0.0291(3) 0.33320(6) 0.49997(16) 0.0167(4) Uani 1 1 d . . .
H19 H -0.0961 0.3236 0.5264 0.020 Uiso 1 1 calc R . .
C15 C 0.4082(3) 0.34527(6) 0.54001(16) 0.0168(4) Uani 1 1 d . . .
H15 H 0.5395 0.3435 0.5930 0.020 Uiso 1 1 calc R . .
C18 C 0.0202(3) 0.35091(6) 0.37854(16) 0.0192(4) Uani 1 1 d . . .
H18 H -0.1109 0.3523 0.3253 0.023 Uiso 1 1 calc R . .
C12 C 0.4848(3) 0.41718(6) 0.80279(17) 0.0185(4) Uani 1 1 d . . .
H12 H 0.6083 0.4089 0.7726 0.022 Uiso 1 1 calc R . .
C17 C 0.2038(3) 0.36637(6) 0.33632(16) 0.0186(4) Uani 1 1 d . . .
C10 C 0.2546(3) 0.47770(6) 0.86645(17) 0.0188(4) Uani 1 1 d . . .
C9 C 0.1160(3) 0.44199(6) 0.89339(16) 0.0181(4) Uani 1 1 d . . .
H9 H -0.0076 0.4503 0.9235 0.022 Uiso 1 1 calc R . .
C16 C 0.3984(3) 0.36339(6) 0.41963(16) 0.0186(4) Uani 1 1 d . . .
H16 H 0.5234 0.3737 0.3941 0.022 Uiso 1 1 calc R . .
C11 C 0.4403(3) 0.46565(6) 0.82134(17) 0.0204(4) Uani 1 1 d . . .
H11 H 0.5334 0.4895 0.8038 0.024 Uiso 1 1 calc R . .
C20 C 0.1937(3) 0.38650(7) 0.20606(17) 0.0239(4) Uani 1 1 d . . .
H20A H 0.0645 0.3759 0.1540 0.036 Uiso 1 1 calc R . .
H20B H 0.3149 0.3754 0.1721 0.036 Uiso 1 1 calc R . .
H20C H 0.1955 0.4210 0.2096 0.036 Uiso 1 1 calc R . .
C13 C 0.3405(3) 0.56152(6) 0.86801(19) 0.0252(4) Uani 1 1 d . . .
H13A H 0.3505 0.5627 0.7811 0.038 Uiso 1 1 calc R . .
H13B H 0.4793 0.5553 0.9160 0.038 Uiso 1 1 calc R . .
H13C H 0.2885 0.5918 0.8928 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
O4 C6 1.330(2) . ?
O1 C5 1.2473(19) . ?
O3 C6 1.217(2) . ?
O2 C10 1.375(2) . ?
O2 C13 1.430(2) . ?
N1 C5 1.3581(19) . ?
N1 C1 1.4856(19) . ?
N1 C7 1.447(2) . ?
C5 C4 1.512(2) . ?
C6 C2 1.526(2) . ?
C1 C14 1.531(2) . ?
C1 C2 1.556(2) . ?
C14 C19 1.399(2) . ?
C14 C15 1.391(2) . ?
C7 C8 1.400(2) . ?
C7 C12 1.378(2) . ?
C2 C3 1.518(2) . ?
C8 C9 1.395(2) . ?
C4 C3 1.524(2) . ?
C19 C18 1.404(2) . ?
C15 C16 1.396(2) . ?
C18 C17 1.392(3) . ?
C12 C11 1.399(2) . ?
C17 C16 1.404(2) . ?
C17 C20 1.517(2) . ?
C10 C9 1.391(3) . ?
C10 C11 1.394(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
C10 O2 C13 117.13(14) . . ?
C5 N1 C1 125.76(13) . . ?
C5 N1 C7 119.21(13) . . ?
C7 N1 C1 114.92(12) . . ?
O1 C5 N1 121.29(15) . . ?
O1 C5 C4 119.71(13) . . ?
N1 C5 C4 118.99(13) . . ?
O4 C6 C2 111.65(14) . . ?
O3 C6 O4 123.96(14) . . ?
O3 C6 C2 124.38(15) . . ?
N1 C1 C14 110.83(13) . . ?
N1 C1 C2 110.56(12) . . ?
C14 C1 C2 113.49(13) . . ?
C19 C14 C1 119.05(15) . . ?
C15 C14 C1 122.73(14) . . ?
C15 C14 C19 118.18(15) . . ?
C8 C7 N1 119.61(14) . . ?
C12 C7 N1 120.35(15) . . ?
C12 C7 C8 120.02(15) . . ?
C6 C2 C1 110.43(12) . . ?
C3 C2 C6 111.55(13) . . ?
C3 C2 C1 110.12(13) . . ?
C9 C8 C7 119.64(16) . . ?
C5 C4 C3 114.59(13) . . ?
C2 C3 C4 107.61(13) . . ?
C14 C19 C18 120.77(16) . . ?
C14 C15 C16 120.90(14) . . ?
C17 C18 C19 121.26(15) . . ?
C7 C12 C11 120.80(17) . . ?
C18 C17 C16 117.48(16) . . ?
C18 C17 C20 121.33(15) . . ?
C16 C17 C20 121.18(17) . . ?
O2 C10 C9 115.69(16) . . ?
O2 C10 C11 123.88(16) . . ?
C9 C10 C11 120.42(16) . . ?
C10 C9 C8 120.00(16) . . ?
C15 C16 C17 121.40(16) . . ?
C10 C11 C12 119.11(16) . . ?
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.014 0.000 0.000 155 21 ' '
2 -0.051 0.500 0.500 155 21 ' '
_platon_squeeze_details          
;
;


####################################################################### 
# 
# 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_dvd72
_database_code_depnum_ccdc_archive 'CCDC 1442947'
_audit_update_record             
;
2015-12-16 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;
_audit_creation_date             2015-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 N O4'
_chemical_formula_sum            'C16 H21 N O4'
_chemical_formula_weight         291.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   23.216(3)
_cell_length_b                   11.7924(16)
_cell_length_c                   23.055(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.933(2)
_cell_angle_gamma                90
_cell_volume                     6126.1(15)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    9847
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      2.22
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2496
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            73928
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.111
_diffrn_reflns_theta_min         1.820
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9957
_reflns_number_total             12171
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     777
_refine_ls_number_reflns         12171
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0405P)²+2.8642P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0870
_refine_ls_wR_factor_ref         0.0948
_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:
 C1(H1), C2(H2), C1A(H1A), C2A(H2A), C1C(H1C), C2C(H2C), C1B(H1B), C2B(H2B)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C3A(H3AB,H3AC), C3C(H3CA,H3CB), C3B(H3BB,H3BC)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15), C11A(H11A), C12A(H12A), C14A(H14A),
 C15A(H15A), C11C(H11C), C12C(H12C), C14C(H14C), C15C(H15C), C11B(H11B),
 C12B(H12B), C14B(H14B), C15B(H15B)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C16(H16A,H16B,H16C),
 C7A(H7AA,H7AB,H7AC), C8A(H8AA,H8AB,H8AC), C9A(H9AA,H9AB,H9AC), C16A(H16D,H16E,
 H16F), C7C(H7CA,H7CB,H7CC), C8C(H8CA,H8CB,H8CC), C9C(H9CA,H9CB,H9CC),
 C16C(H16G,H16H,H16I), C7B(H7BA,H7BB,H7BC), C8B(H8BA,H8BB,H8BC), C9B(H9BA,H9BB,
 H9BC), C16B(H16J,H16K,H16L)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O3A(H3AA), O3C(H3C), O3B(H3BA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.60872(4) 0.08013(8) 0.33620(4) 0.0186(2) Uani 1 1 d . . . . .
O2 O 0.45816(5) 0.40804(10) 0.26395(5) 0.0289(3) Uani 1 1 d . . . . .
O3 O 0.47221(4) 0.42280(8) 0.17119(4) 0.0211(2) Uani 1 1 d . . . . .
H3 H 0.4475 0.4735 0.1681 0.032 Uiso 1 1 calc GR . . . .
O4 O 0.66790(5) 0.72832(8) 0.36571(5) 0.0262(2) Uani 1 1 d . . . . .
N1 N 0.62409(5) 0.22240(9) 0.27294(5) 0.0153(2) Uani 1 1 d . . . . .
C1 C 0.59098(6) 0.31923(11) 0.24003(6) 0.0155(3) Uani 1 1 d . . . . .
H1 H 0.5996 0.3244 0.2005 0.019 Uiso 1 1 calc R . . . .
C2 C 0.52549(6) 0.27972(12) 0.23254(6) 0.0183(3) Uani 1 1 d . . . . .
H2 H 0.5146 0.2315 0.1970 0.022 Uiso 1 1 calc R . . . .
C3 C 0.52826(6) 0.20607(13) 0.28727(7) 0.0219(3) Uani 1 1 d . . . . .
H3A H 0.5208 0.2505 0.3201 0.026 Uiso 1 1 calc R . . . .
H3B H 0.4997 0.1447 0.2783 0.026 Uiso 1 1 calc R . . . .
C4 C 0.59104(6) 0.16117(11) 0.30180(6) 0.0171(3) Uani 1 1 d . . . . .
C5 C 0.48156(6) 0.37678(12) 0.22521(6) 0.0184(3) Uani 1 1 d . . . . .
C6 C 0.68855(6) 0.19862(12) 0.27603(6) 0.0176(3) Uani 1 1 d . . . . .
C7 C 0.69209(7) 0.08283(12) 0.24710(7) 0.0240(3) Uani 1 1 d . . . . .
H7A H 0.6748 0.0262 0.2676 0.036 Uiso 1 1 calc GR . . . .
H7B H 0.7329 0.0642 0.2496 0.036 Uiso 1 1 calc GR . . . .
H7C H 0.6708 0.0855 0.2059 0.036 Uiso 1 1 calc GR . . . .
C8 C 0.72413(6) 0.19992(14) 0.34134(7) 0.0251(3) Uani 1 1 d . . . . .
H8A H 0.7197 0.2723 0.3588 0.038 Uiso 1 1 calc GR . . . .
H8B H 0.7653 0.1868 0.3430 0.038 Uiso 1 1 calc GR . . . .
H8C H 0.7097 0.1414 0.3631 0.038 Uiso 1 1 calc GR . . . .
C9 C 0.71341(7) 0.28912(13) 0.24156(7) 0.0241(3) Uani 1 1 d . . . . .
H9A H 0.6923 0.2871 0.2003 0.036 Uiso 1 1 calc GR . . . .
H9B H 0.7548 0.2748 0.2448 0.036 Uiso 1 1 calc GR . . . .
H9C H 0.7088 0.3625 0.2579 0.036 Uiso 1 1 calc GR . . . .
C10 C 0.60747(6) 0.43083(11) 0.27303(6) 0.0161(3) Uani 1 1 d . . . . .
C11 C 0.62162(6) 0.43724(12) 0.33552(6) 0.0193(3) Uani 1 1 d . . . . .
H11 H 0.6181 0.3727 0.3576 0.023 Uiso 1 1 calc R . . . .
C12 C 0.64060(7) 0.53737(12) 0.36498(6) 0.0222(3) Uani 1 1 d . . . . .
H12 H 0.6499 0.5398 0.4065 0.027 Uiso 1 1 calc R . . . .
C13 C 0.64581(6) 0.63511(12) 0.33237(6) 0.0196(3) Uani 1 1 d . . . . .
C14 C 0.62994(6) 0.63197(12) 0.27018(6) 0.0187(3) Uani 1 1 d . . . . .
H14 H 0.6319 0.6972 0.2481 0.022 Uiso 1 1 calc R . . . .
C15 C 0.61104(6) 0.52960(12) 0.24137(6) 0.0174(3) Uani 1 1 d . . . . .
H15 H 0.6006 0.5276 0.1998 0.021 Uiso 1 1 calc R . . . .
C16 C 0.68248(7) 0.82518(12) 0.33457(7) 0.0239(3) Uani 1 1 d . . . . .
H16A H 0.6472 0.8538 0.3078 0.036 Uiso 1 1 calc GR . . . .
H16B H 0.7106 0.8037 0.3121 0.036 Uiso 1 1 calc GR . . . .
H16C H 0.6994 0.8830 0.3629 0.036 Uiso 1 1 calc GR . . . .
O1A O 0.16062(4) 0.16583(8) 0.53116(4) 0.0220(2) Uani 1 1 d . . . . .
O2A O 0.28694(5) 0.50259(9) 0.49070(4) 0.0256(2) Uani 1 1 d . . . . .
O3A O 0.25905(4) 0.50345(9) 0.39040(4) 0.0216(2) Uani 1 1 d . . . . .
H3AA H 0.2835 0.5547 0.3939 0.032 Uiso 1 1 calc GR . . . .
O4A O 0.10995(5) 0.83216(8) 0.53550(5) 0.0246(2) Uani 1 1 d . . . . .
N1A N 0.12647(5) 0.31638(9) 0.46909(5) 0.0163(2) Uani 1 1 d . . . . .
C1A C 0.14965(6) 0.40700(11) 0.43635(6) 0.0167(3) Uani 1 1 d . . . . .
H1A H 0.1273 0.4060 0.3945 0.020 Uiso 1 1 calc R . . . .
C2A C 0.21484(6) 0.36589(12) 0.43994(6) 0.0198(3) Uani 1 1 d . . . . .
H2A H 0.2150 0.3221 0.4039 0.024 Uiso 1 1 calc R . . . .
C3A C 0.22889(6) 0.28597(13) 0.49354(7) 0.0238(3) Uani 1 1 d . . . . .
H3AB H 0.2522 0.2218 0.4860 0.029 Uiso 1 1 calc R . . . .
H3AC H 0.2506 0.3252 0.5291 0.029 Uiso 1 1 calc R . . . .
C4A C 0.16901(6) 0.24799(12) 0.50045(6) 0.0183(3) Uani 1 1 d . . . . .
C5A C 0.25806(6) 0.46392(12) 0.44421(6) 0.0192(3) Uani 1 1 d . . . . .
C6A C 0.06162(6) 0.29900(12) 0.46622(6) 0.0182(3) Uani 1 1 d . . . . .
C7A C 0.02395(6) 0.39695(13) 0.43384(7) 0.0256(3) Uani 1 1 d . . . . .
H7AA H 0.0347 0.4658 0.4560 0.038 Uiso 1 1 calc GR . . . .
H7AB H -0.0173 0.3811 0.4305 0.038 Uiso 1 1 calc GR . . . .
H7AC H 0.0308 0.4054 0.3946 0.038 Uiso 1 1 calc GR . . . .
C8A C 0.04244(7) 0.19056(13) 0.43032(7) 0.0278(3) Uani 1 1 d . . . . .
H8AA H 0.0442 0.2023 0.3896 0.042 Uiso 1 1 calc GR . . . .
H8AB H 0.0026 0.1717 0.4317 0.042 Uiso 1 1 calc GR . . . .
H8AC H 0.0685 0.1296 0.4472 0.042 Uiso 1 1 calc GR . . . .
C9A C 0.05237(7) 0.29239(15) 0.52954(7) 0.0284(3) Uani 1 1 d . . . . .
H9AA H 0.0714 0.2256 0.5490 0.043 Uiso 1 1 calc GR . . . .
H9AB H 0.0107 0.2891 0.5277 0.043 Uiso 1 1 calc GR . . . .
H9AC H 0.0692 0.3583 0.5517 0.043 Uiso 1 1 calc GR . . . .
C10A C 0.14352(6) 0.52328(11) 0.46239(6) 0.0163(3) Uani 1 1 d . . . . .
C11A C 0.16072(6) 0.54431(12) 0.52387(6) 0.0194(3) Uani 1 1 d . . . . .
H11A H 0.1795 0.4876 0.5496 0.023 Uiso 1 1 calc R . . . .
C12A C 0.15011(6) 0.64870(12) 0.54680(6) 0.0207(3) Uani 1 1 d . . . . .
H12A H 0.1620 0.6620 0.5877 0.025 Uiso 1 1 calc R . . . .
C13A C 0.12148(6) 0.73433(11) 0.50829(6) 0.0187(3) Uani 1 1 d . . . . .
C14A C 0.10572(6) 0.71578(12) 0.44710(6) 0.0184(3) Uani 1 1 d . . . . .
H14A H 0.0880 0.7731 0.4212 0.022 Uiso 1 1 calc R . . . .
C15A C 0.11674(6) 0.61042(12) 0.42505(6) 0.0178(3) Uani 1 1 d . . . . .
H15A H 0.1058 0.5979 0.3840 0.021 Uiso 1 1 calc R . . . .
C16A C 0.08168(7) 0.92212(12) 0.49725(7) 0.0245(3) Uani 1 1 d . . . . .
H16D H 0.1056 0.9423 0.4701 0.037 Uiso 1 1 calc GR . . . .
H16E H 0.0772 0.9869 0.5210 0.037 Uiso 1 1 calc GR . . . .
H16F H 0.0433 0.8975 0.4750 0.037 Uiso 1 1 calc GR . . . .
O1C O 0.07329(4) 1.19972(9) 0.17292(4) 0.0225(2) Uani 1 1 d . . . . .
O2C O -0.03423(5) 0.86020(9) 0.23469(5) 0.0260(2) Uani 1 1 d . . . . .
O3C O 0.00147(4) 0.86519(9) 0.33438(4) 0.0228(2) Uani 1 1 d . . . . .
H3C H -0.0212 0.8117 0.3337 0.034 Uiso 1 1 calc GR . . . .
O4C O 0.14346(5) 0.53442(8) 0.21356(5) 0.0254(2) Uani 1 1 d . . . . .
N1C N 0.11709(5) 1.07645(10) 0.24797(5) 0.0168(2) Uani 1 1 d . . . . .
C1C C 0.10012(6) 0.98369(12) 0.28374(6) 0.0174(3) Uani 1 1 d . . . . .
H1C H 0.1220 0.9925 0.3255 0.021 Uiso 1 1 calc R . . . .
C2C C 0.03273(6) 1.01029(12) 0.27865(6) 0.0192(3) Uani 1 1 d . . . . .
H2C H 0.0296 1.0581 0.3126 0.023 Uiso 1 1 calc R . . . .
C3C C 0.01349(6) 1.07963(12) 0.22159(6) 0.0215(3) Uani 1 1 d . . . . .
H3CA H -0.0065 1.0321 0.1885 0.026 Uiso 1 1 calc R . . . .
H3CB H -0.0131 1.1403 0.2266 0.026 Uiso 1 1 calc R . . . .
C4C C 0.07031(6) 1.12661(12) 0.21096(6) 0.0182(3) Uani 1 1 d . . . . .
C5C C -0.00409(6) 0.90411(12) 0.27918(6) 0.0192(3) Uani 1 1 d . . . . .
C6C C 0.18011(6) 1.10878(12) 0.24967(6) 0.0195(3) Uani 1 1 d . . . . .
C7C C 0.22238(6) 1.04517(13) 0.30023(6) 0.0235(3) Uani 1 1 d . . . . .
H7CA H 0.2148 1.0670 0.3378 0.035 Uiso 1 1 calc GR . . . .
H7CB H 0.2626 1.0635 0.3000 0.035 Uiso 1 1 calc GR . . . .
H7CC H 0.2163 0.9650 0.2946 0.035 Uiso 1 1 calc GR . . . .
C8C C 0.19381(7) 1.07842(15) 0.18980(7) 0.0273(3) Uani 1 1 d . . . . .
H8CA H 0.1893 0.9982 0.1833 0.041 Uiso 1 1 calc GR . . . .
H8CB H 0.2338 1.1002 0.1905 0.041 Uiso 1 1 calc GR . . . .
H8CC H 0.1669 1.1179 0.1581 0.041 Uiso 1 1 calc GR . . . .
C9C C 0.18755(7) 1.23639(13) 0.26258(7) 0.0280(3) Uani 1 1 d . . . . .
H9CA H 0.1646 1.2782 0.2292 0.042 Uiso 1 1 calc GR . . . .
H9CB H 0.2287 1.2565 0.2689 0.042 Uiso 1 1 calc GR . . . .
H9CC H 0.1740 1.2542 0.2977 0.042 Uiso 1 1 calc GR . . . .
C10C C 0.11213(6) 0.86600(12) 0.26219(6) 0.0166(3) Uani 1 1 d . . . . .
C11C C 0.13684(6) 0.78248(12) 0.30396(6) 0.0191(3) Uani 1 1 d . . . . .
H11C H 0.1466 0.8007 0.3444 0.023 Uiso 1 1 calc R . . . .
C12C C 0.14713(6) 0.67339(12) 0.28656(6) 0.0207(3) Uani 1 1 d . . . . .
H12C H 0.1640 0.6196 0.3151 0.025 Uiso 1 1 calc R . . . .
C13C C 0.13206(6) 0.64437(12) 0.22609(6) 0.0195(3) Uani 1 1 d . . . . .
C14C C 0.10772(6) 0.72613(12) 0.18343(6) 0.0189(3) Uani 1 1 d . . . . .
H14C H 0.0978 0.7077 0.1430 0.023 Uiso 1 1 calc R . . . .
C15C C 0.09845(6) 0.83572(12) 0.20201(6) 0.0184(3) Uani 1 1 d . . . . .
H15C H 0.0827 0.8902 0.1734 0.022 Uiso 1 1 calc R . . . .
C16C C 0.12863(7) 0.50022(13) 0.15216(7) 0.0267(3) Uani 1 1 d . . . . .
H16G H 0.1513 0.5440 0.1304 0.040 Uiso 1 1 calc GR . . . .
H16H H 0.0871 0.5125 0.1355 0.040 Uiso 1 1 calc GR . . . .
H16I H 0.1376 0.4212 0.1495 0.040 Uiso 1 1 calc GR . . . .
O1B O 0.34024(4) 0.66486(8) 0.40587(4) 0.0213(2) Uani 1 1 d . . . . .
O2B O 0.20137(5) 0.98740(9) 0.44199(4) 0.0258(2) Uani 1 1 d . . . . .
O3B O 0.23623(4) 1.00168(9) 0.54154(4) 0.0214(2) Uani 1 1 d . . . . .
H3BA H 0.2118 1.0530 0.5378 0.032 Uiso 1 1 calc GR . . . .
O4B O 0.38359(5) 1.34254(8) 0.43409(5) 0.0246(2) Uani 1 1 d . . . . .
N1B N 0.36966(5) 0.80204(10) 0.47838(5) 0.0173(2) Uani 1 1 d . . . . .
C1B C 0.34299(6) 0.89393(12) 0.50713(6) 0.0169(3) Uani 1 1 d . . . . .
H1B H 0.3596 0.8910 0.5504 0.020 Uiso 1 1 calc R . . . .
C2B C 0.27625(6) 0.85634(12) 0.49321(6) 0.0179(3) Uani 1 1 d . . . . .
H2B H 0.2709 0.8067 0.5256 0.022 Uiso 1 1 calc R . . . .
C3B C 0.26773(6) 0.78582(13) 0.43651(6) 0.0210(3) Uani 1 1 d . . . . .
H3BB H 0.2405 0.7236 0.4368 0.025 Uiso 1 1 calc R . . . .
H3BC H 0.2527 0.8320 0.4013 0.025 Uiso 1 1 calc R . . . .
C4B C 0.32932(6) 0.74249(12) 0.43817(6) 0.0182(3) Uani 1 1 d . . . . .
C5B C 0.23377(6) 0.95524(12) 0.48859(6) 0.0186(3) Uani 1 1 d . . . . .
C6B C 0.43539(6) 0.77919(13) 0.49107(6) 0.0208(3) Uani 1 1 d . . . . .
C7B C 0.44666(7) 0.65688(14) 0.51357(7) 0.0301(4) Uani 1 1 d . . . . .
H7BA H 0.4336 0.6479 0.5498 0.045 Uiso 1 1 calc GR . . . .
H7BB H 0.4883 0.6405 0.5212 0.045 Uiso 1 1 calc GR . . . .
H7BC H 0.4251 0.6056 0.4838 0.045 Uiso 1 1 calc GR . . . .
C8B C 0.45656(7) 0.79717(15) 0.43368(7) 0.0287(4) Uani 1 1 d . . . . .
H8BA H 0.4361 0.7456 0.4035 0.043 Uiso 1 1 calc GR . . . .
H8BB H 0.4985 0.7834 0.4416 0.043 Uiso 1 1 calc GR . . . .
H8BC H 0.4484 0.8737 0.4200 0.043 Uiso 1 1 calc GR . . . .
C9B C 0.46887(6) 0.86037(14) 0.53923(7) 0.0273(3) Uani 1 1 d . . . . .
H9BA H 0.4617 0.9371 0.5255 0.041 Uiso 1 1 calc GR . . . .
H9BB H 0.5106 0.8447 0.5473 0.041 Uiso 1 1 calc GR . . . .
H9BC H 0.4553 0.8503 0.5751 0.041 Uiso 1 1 calc GR . . . .
C10B C 0.35326(6) 1.01182(12) 0.48456(6) 0.0168(3) Uani 1 1 d . . . . .
C11B C 0.36719(6) 1.10125(12) 0.52556(6) 0.0190(3) Uani 1 1 d . . . . .
H11B H 0.3703 1.0870 0.5659 0.023 Uiso 1 1 calc R . . . .
C12B C 0.37636(6) 1.21010(12) 0.50754(6) 0.0196(3) Uani 1 1 d . . . . .
H12B H 0.3853 1.2682 0.5355 0.023 Uiso 1 1 calc R . . . .
C13B C 0.37218(6) 1.23278(12) 0.44721(6) 0.0195(3) Uani 1 1 d . . . . .
C14B C 0.35787(6) 1.14574(12) 0.40556(6) 0.0202(3) Uani 1 1 d . . . . .
H14B H 0.3545 1.1603 0.3652 0.024 Uiso 1 1 calc R . . . .
C15B C 0.34851(6) 1.03623(12) 0.42456(6) 0.0194(3) Uani 1 1 d . . . . .
H15B H 0.3389 0.9784 0.3965 0.023 Uiso 1 1 calc R . . . .
C16B C 0.38462(8) 1.36888(14) 0.37389(7) 0.0297(4) Uani 1 1 d . . . . .
H16J H 0.3461 1.3551 0.3481 0.045 Uiso 1 1 calc GR . . . .
H16K H 0.4135 1.3220 0.3618 0.045 Uiso 1 1 calc GR . . . .
H16L H 0.3949 1.4472 0.3713 0.045 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.2466(16) . ?
O2 C5 1.2093(17) . ?
O3 H3 0.8200 . ?
O3 C5 1.3276(17) . ?
O4 C13 1.3682(17) . ?
O4 C16 1.4323(18) . ?
N1 C1 1.4796(17) . ?
N1 C4 1.3412(17) . ?
N1 C6 1.5074(17) . ?
C1 H1 0.9800 . ?
C1 C2 1.5596(18) . ?
C1 C10 1.5222(18) . ?
C2 H2 0.9800 . ?
C2 C3 1.5203(19) . ?
C2 C5 1.5151(19) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.5105(19) . ?
C6 C7 1.5306(19) . ?
C6 C8 1.533(2) . ?
C6 C9 1.525(2) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.4004(19) . ?
C10 C15 1.3876(19) . ?
C11 H11 0.9300 . ?
C11 C12 1.380(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.397(2) . ?
C13 C14 1.392(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.3965(19) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O1A C4A 1.2428(17) . ?
O2A C5A 1.2083(17) . ?
O3A H3AA 0.8200 . ?
O3A C5A 1.3305(17) . ?
O4A C13A 1.3699(17) . ?
O4A C16A 1.4336(17) . ?
N1A C1A 1.4823(17) . ?
N1A C4A 1.3432(18) . ?
N1A C6A 1.5050(17) . ?
C1A H1A 0.9800 . ?
C1A C2A 1.5722(19) . ?
C1A C10A 1.5172(19) . ?
C2A H2A 0.9800 . ?
C2A C3A 1.526(2) . ?
C2A C5A 1.518(2) . ?
C3A H3AB 0.9700 . ?
C3A H3AC 0.9700 . ?
C3A C4A 1.505(2) . ?
C6A C7A 1.5304(19) . ?
C6A C8A 1.530(2) . ?
C6A C9A 1.528(2) . ?
C7A H7AA 0.9600 . ?
C7A H7AB 0.9600 . ?
C7A H7AC 0.9600 . ?
C8A H8AA 0.9600 . ?
C8A H8AB 0.9600 . ?
C8A H8AC 0.9600 . ?
C9A H9AA 0.9600 . ?
C9A H9AB 0.9600 . ?
C9A H9AC 0.9600 . ?
C10A C11A 1.3992(19) . ?
C10A C15A 1.3877(19) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.385(2) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.402(2) . ?
C13A C14A 1.387(2) . ?
C14A H14A 0.9300 . ?
C14A C15A 1.389(2) . ?
C15A H15A 0.9300 . ?
C16A H16D 0.9600 . ?
C16A H16E 0.9600 . ?
C16A H16F 0.9600 . ?
O1C C4C 1.2436(17) . ?
O2C C5C 1.2101(17) . ?
O3C H3C 0.8200 . ?
O3C C5C 1.3294(17) . ?
O4C C13C 1.3680(17) . ?
O4C C16C 1.4319(18) . ?
N1C C1C 1.4792(17) . ?
N1C C4C 1.3458(18) . ?
N1C C6C 1.5033(18) . ?
C1C H1C 0.9800 . ?
C1C C2C 1.5721(19) . ?
C1C C10C 1.5223(19) . ?
C2C H2C 0.9800 . ?
C2C C3C 1.522(2) . ?
C2C C5C 1.5178(19) . ?
C3C H3CA 0.9700 . ?
C3C H3CB 0.9700 . ?
C3C C4C 1.504(2) . ?
C6C C7C 1.5276(19) . ?
C6C C8C 1.532(2) . ?
C6C C9C 1.536(2) . ?
C7C H7CA 0.9600 . ?
C7C H7CB 0.9600 . ?
C7C H7CC 0.9600 . ?
C8C H8CA 0.9600 . ?
C8C H8CB 0.9600 . ?
C8C H8CC 0.9600 . ?
C9C H9CA 0.9600 . ?
C9C H9CB 0.9600 . ?
C9C H9CC 0.9600 . ?
C10C C11C 1.4002(19) . ?
C10C C15C 1.3931(19) . ?
C11C H11C 0.9300 . ?
C11C C12C 1.385(2) . ?
C12C H12C 0.9300 . ?
C12C C13C 1.396(2) . ?
C13C C14C 1.396(2) . ?
C14C H14C 0.9300 . ?
C14C C15C 1.394(2) . ?
C15C H15C 0.9300 . ?
C16C H16G 0.9600 . ?
C16C H16H 0.9600 . ?
C16C H16I 0.9600 . ?
O1B C4B 1.2441(17) . ?
O2B C5B 1.2143(17) . ?
O3B H3BA 0.8200 . ?
O3B C5B 1.3266(17) . ?
O4B C13B 1.3694(17) . ?
O4B C16B 1.4282(18) . ?
N1B C1B 1.4814(17) . ?
N1B C4B 1.3460(18) . ?
N1B C6B 1.5073(17) . ?
C1B H1B 0.9800 . ?
C1B C2B 1.5685(18) . ?
C1B C10B 1.5232(19) . ?
C2B H2B 0.9800 . ?
C2B C3B 1.5215(19) . ?
C2B C5B 1.5145(19) . ?
C3B H3BB 0.9700 . ?
C3B H3BC 0.9700 . ?
C3B C4B 1.5101(19) . ?
C6B C7B 1.534(2) . ?
C6B C8B 1.533(2) . ?
C6B C9B 1.529(2) . ?
C7B H7BA 0.9600 . ?
C7B H7BB 0.9600 . ?
C7B H7BC 0.9600 . ?
C8B H8BA 0.9600 . ?
C8B H8BB 0.9600 . ?
C8B H8BC 0.9600 . ?
C9B H9BA 0.9600 . ?
C9B H9BB 0.9600 . ?
C9B H9BC 0.9600 . ?
C10B C11B 1.401(2) . ?
C10B C15B 1.3910(19) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.381(2) . ?
C12B H12B 0.9300 . ?
C12B C13B 1.397(2) . ?
C13B C14B 1.390(2) . ?
C14B H14B 0.9300 . ?
C14B C15B 1.397(2) . ?
C15B H15B 0.9300 . ?
C16B H16J 0.9600 . ?
C16B H16K 0.9600 . ?
C16B H16L 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
C5 O3 H3 109.5 . . ?
C13 O4 C16 117.44(11) . . ?
C1 N1 C6 123.71(11) . . ?
C4 N1 C1 112.41(11) . . ?
C4 N1 C6 123.81(11) . . ?
N1 C1 H1 109.1 . . ?
N1 C1 C2 101.44(10) . . ?
N1 C1 C10 111.95(10) . . ?
C2 C1 H1 109.1 . . ?
C10 C1 H1 109.1 . . ?
C10 C1 C2 115.78(11) . . ?
C1 C2 H2 108.3 . . ?
C3 C2 C1 103.50(11) . . ?
C3 C2 H2 108.3 . . ?
C5 C2 C1 113.50(11) . . ?
C5 C2 H2 108.3 . . ?
C5 C2 C3 114.64(12) . . ?
C2 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
C4 C3 C2 103.31(11) . . ?
C4 C3 H3A 111.1 . . ?
C4 C3 H3B 111.1 . . ?
O1 C4 N1 126.04(13) . . ?
O1 C4 C3 124.21(12) . . ?
N1 C4 C3 109.75(12) . . ?
O2 C5 O3 124.55(13) . . ?
O2 C5 C2 123.92(13) . . ?
O3 C5 C2 111.53(12) . . ?
N1 C6 C7 107.59(11) . . ?
N1 C6 C8 109.78(11) . . ?
N1 C6 C9 109.95(11) . . ?
C7 C6 C8 111.36(12) . . ?
C9 C6 C7 109.30(12) . . ?
C9 C6 C8 108.84(12) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C1 121.96(12) . . ?
C15 C10 C1 120.16(12) . . ?
C15 C10 C11 117.84(12) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.35(13) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 119.97(13) . . ?
C13 C12 H12 120.0 . . ?
O4 C13 C12 115.45(12) . . ?
O4 C13 C14 124.78(13) . . ?
C14 C13 C12 119.77(13) . . ?
C13 C14 H14 120.4 . . ?
C13 C14 C15 119.19(13) . . ?
C15 C14 H14 120.4 . . ?
C10 C15 C14 121.81(12) . . ?
C10 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C5A O3A H3AA 109.5 . . ?
C13A O4A C16A 116.90(11) . . ?
C1A N1A C6A 123.91(11) . . ?
C4A N1A C1A 113.38(11) . . ?
C4A N1A C6A 122.68(11) . . ?
N1A C1A H1A 108.8 . . ?
N1A C1A C2A 102.35(10) . . ?
N1A C1A C10A 111.71(11) . . ?
C2A C1A H1A 108.8 . . ?
C10A C1A H1A 108.8 . . ?
C10A C1A C2A 116.02(11) . . ?
C1A C2A H2A 108.6 . . ?
C3A C2A C1A 104.39(11) . . ?
C3A C2A H2A 108.6 . . ?
C5A C2A C1A 112.42(11) . . ?
C5A C2A H2A 108.6 . . ?
C5A C2A C3A 114.12(12) . . ?
C2A C3A H3AB 110.9 . . ?
C2A C3A H3AC 110.9 . . ?
H3AB C3A H3AC 108.9 . . ?
C4A C3A C2A 104.28(11) . . ?
C4A C3A H3AB 110.9 . . ?
C4A C3A H3AC 110.9 . . ?
O1A C4A N1A 125.37(13) . . ?
O1A C4A C3A 124.59(13) . . ?
N1A C4A C3A 110.03(12) . . ?
O2A C5A O3A 124.35(13) . . ?
O2A C5A C2A 124.18(13) . . ?
O3A C5A C2A 111.45(12) . . ?
N1A C6A C7A 111.51(11) . . ?
N1A C6A C8A 107.18(11) . . ?
N1A C6A C9A 109.53(11) . . ?
C8A C6A C7A 108.01(12) . . ?
C9A C6A C7A 108.02(12) . . ?
C9A C6A C8A 112.63(13) . . ?
C6A C7A H7AA 109.5 . . ?
C6A C7A H7AB 109.5 . . ?
C6A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C6A C8A H8AA 109.5 . . ?
C6A C8A H8AB 109.5 . . ?
C6A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C6A C9A H9AA 109.5 . . ?
C6A C9A H9AB 109.5 . . ?
C6A C9A H9AC 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C11A C10A C1A 122.00(12) . . ?
C15A C10A C1A 119.64(12) . . ?
C15A C10A C11A 118.23(13) . . ?
C10A C11A H11A 119.6 . . ?
C12A C11A C10A 120.70(13) . . ?
C12A C11A H11A 119.6 . . ?
C11A C12A H12A 120.0 . . ?
C11A C12A C13A 119.96(13) . . ?
C13A C12A H12A 120.0 . . ?
O4A C13A C12A 115.58(12) . . ?
O4A C13A C14A 124.46(13) . . ?
C14A C13A C12A 119.95(13) . . ?
C13A C14A H14A 120.4 . . ?
C13A C14A C15A 119.11(13) . . ?
C15A C14A H14A 120.4 . . ?
C10A C15A C14A 122.00(13) . . ?
C10A C15A H15A 119.0 . . ?
C14A C15A H15A 119.0 . . ?
O4A C16A H16D 109.5 . . ?
O4A C16A H16E 109.5 . . ?
O4A C16A H16F 109.5 . . ?
H16D C16A H16E 109.5 . . ?
H16D C16A H16F 109.5 . . ?
H16E C16A H16F 109.5 . . ?
C5C O3C H3C 109.5 . . ?
C13C O4C C16C 117.58(11) . . ?
C1C N1C C6C 124.14(11) . . ?
C4C N1C C1C 113.32(11) . . ?
C4C N1C C6C 122.46(11) . . ?
N1C C1C H1C 108.9 . . ?
N1C C1C C2C 101.82(11) . . ?
N1C C1C C10C 113.45(11) . . ?
C2C C1C H1C 108.9 . . ?
C10C C1C H1C 108.9 . . ?
C10C C1C C2C 114.50(11) . . ?
C1C C2C H2C 108.5 . . ?
C3C C2C C1C 104.56(11) . . ?
C3C C2C H2C 108.5 . . ?
C5C C2C C1C 112.78(11) . . ?
C5C C2C H2C 108.5 . . ?
C5C C2C C3C 113.67(12) . . ?
C2C C3C H3CA 110.8 . . ?
C2C C3C H3CB 110.8 . . ?
H3CA C3C H3CB 108.9 . . ?
C4C C3C C2C 104.61(11) . . ?
C4C C3C H3CA 110.8 . . ?
C4C C3C H3CB 110.8 . . ?
O1C C4C N1C 125.34(13) . . ?
O1C C4C C3C 124.76(12) . . ?
N1C C4C C3C 109.89(12) . . ?
O2C C5C O3C 124.52(13) . . ?
O2C C5C C2C 123.92(13) . . ?
O3C C5C C2C 111.56(11) . . ?
N1C C6C C7C 109.74(11) . . ?
N1C C6C C8C 109.22(11) . . ?
N1C C6C C9C 108.48(12) . . ?
C7C C6C C8C 109.77(12) . . ?
C7C C6C C9C 108.16(12) . . ?
C8C C6C C9C 111.45(13) . . ?
C6C C7C H7CA 109.5 . . ?
C6C C7C H7CB 109.5 . . ?
C6C C7C H7CC 109.5 . . ?
H7CA C7C H7CB 109.5 . . ?
H7CA C7C H7CC 109.5 . . ?
H7CB C7C H7CC 109.5 . . ?
C6C C8C H8CA 109.5 . . ?
C6C C8C H8CB 109.5 . . ?
C6C C8C H8CC 109.5 . . ?
H8CA C8C H8CB 109.5 . . ?
H8CA C8C H8CC 109.5 . . ?
H8CB C8C H8CC 109.5 . . ?
C6C C9C H9CA 109.5 . . ?
C6C C9C H9CB 109.5 . . ?
C6C C9C H9CC 109.5 . . ?
H9CA C9C H9CB 109.5 . . ?
H9CA C9C H9CC 109.5 . . ?
H9CB C9C H9CC 109.5 . . ?
C11C C10C C1C 119.58(12) . . ?
C15C C10C C1C 122.88(12) . . ?
C15C C10C C11C 117.52(13) . . ?
C10C C11C H11C 119.2 . . ?
C12C C11C C10C 121.64(13) . . ?
C12C C11C H11C 119.2 . . ?
C11C C12C H12C 120.1 . . ?
C11C C12C C13C 119.85(13) . . ?
C13C C12C H12C 120.1 . . ?
O4C C13C C12C 115.37(12) . . ?
O4C C13C C14C 124.89(13) . . ?
C12C C13C C14C 119.73(13) . . ?
C13C C14C H14C 120.3 . . ?
C15C C14C C13C 119.33(13) . . ?
C15C C14C H14C 120.3 . . ?
C10C C15C C14C 121.90(13) . . ?
C10C C15C H15C 119.0 . . ?
C14C C15C H15C 119.0 . . ?
O4C C16C H16G 109.5 . . ?
O4C C16C H16H 109.5 . . ?
O4C C16C H16I 109.5 . . ?
H16G C16C H16H 109.5 . . ?
H16G C16C H16I 109.5 . . ?
H16H C16C H16I 109.5 . . ?
C5B O3B H3BA 109.5 . . ?
C13B O4B C16B 118.00(11) . . ?
C1B N1B C6B 123.82(11) . . ?
C4B N1B C1B 113.17(11) . . ?
C4B N1B C6B 122.99(12) . . ?
N1B C1B H1B 109.0 . . ?
N1B C1B C2B 101.56(10) . . ?
N1B C1B C10B 113.46(11) . . ?
C2B C1B H1B 109.0 . . ?
C10B C1B H1B 109.0 . . ?
C10B C1B C2B 114.60(11) . . ?
C1B C2B H2B 108.3 . . ?
C3B C2B C1B 104.36(11) . . ?
C3B C2B H2B 108.3 . . ?
C5B C2B C1B 113.03(11) . . ?
C5B C2B H2B 108.3 . . ?
C5B C2B C3B 114.38(11) . . ?
C2B C3B H3BB 111.0 . . ?
C2B C3B H3BC 111.0 . . ?
H3BB C3B H3BC 109.0 . . ?
C4B C3B C2B 103.69(11) . . ?
C4B C3B H3BB 111.0 . . ?
C4B C3B H3BC 111.0 . . ?
O1B C4B N1B 126.01(13) . . ?
O1B C4B C3B 124.19(13) . . ?
N1B C4B C3B 109.78(12) . . ?
O2B C5B O3B 124.44(13) . . ?
O2B C5B C2B 123.84(13) . . ?
O3B C5B C2B 111.72(11) . . ?
N1B C6B C7B 108.43(12) . . ?
N1B C6B C8B 109.13(11) . . ?
N1B C6B C9B 110.05(11) . . ?
C8B C6B C7B 110.97(13) . . ?
C9B C6B C7B 109.13(12) . . ?
C9B C6B C8B 109.12(13) . . ?
C6B C7B H7BA 109.5 . . ?
C6B C7B H7BB 109.5 . . ?
C6B C7B H7BC 109.5 . . ?
H7BA C7B H7BB 109.5 . . ?
H7BA C7B H7BC 109.5 . . ?
H7BB C7B H7BC 109.5 . . ?
C6B C8B H8BA 109.5 . . ?
C6B C8B H8BB 109.5 . . ?
C6B C8B H8BC 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
C6B C9B H9BA 109.5 . . ?
C6B C9B H9BB 109.5 . . ?
C6B C9B H9BC 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
C11B C10B C1B 119.09(12) . . ?
C15B C10B C1B 123.17(12) . . ?
C15B C10B C11B 117.73(13) . . ?
C10B C11B H11B 119.2 . . ?
C12B C11B C10B 121.58(13) . . ?
C12B C11B H11B 119.2 . . ?
C11B C12B H12B 120.0 . . ?
C11B C12B C13B 119.92(13) . . ?
C13B C12B H12B 120.0 . . ?
O4B C13B C12B 115.48(13) . . ?
O4B C13B C14B 124.91(13) . . ?
C14B C13B C12B 119.61(13) . . ?
C13B C14B H14B 120.2 . . ?
C13B C14B C15B 119.70(13) . . ?
C15B C14B H14B 120.2 . . ?
C10B C15B C14B 121.45(13) . . ?
C10B C15B H15B 119.3 . . ?
C14B C15B H15B 119.3 . . ?
O4B C16B H16J 109.5 . . ?
O4B C16B H16K 109.5 . . ?
O4B C16B H16L 109.5 . . ?
H16J C16B H16K 109.5 . . ?
H16J C16B H16L 109.5 . . ?
H16K C16B H16L 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_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_dvd35
_database_code_depnum_ccdc_archive 'CCDC 1442993'
_audit_update_record             
;
2015-12-16 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;
_audit_creation_date             2015-12-16
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C17 H23 N O4'
_chemical_formula_sum            'C17 H23 N O4'
_chemical_formula_weight         305.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'O3 C20 H18'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   6.5824(9)
_cell_length_b                   21.392(2)
_cell_length_c                   11.5002(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.054(12)
_cell_angle_gamma                90.00
_cell_volume                     1563.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2342
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.0860
_cell_measurement_theta_min      3.3120
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64899
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7643
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         3.20
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9670
_diffrn_measured_fraction_theta_max 0.9670
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -1.00   48.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4081   57.0000  -90.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega  -40.00   42.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4081   57.0000    0.0000 82

#__ type_ start__ end____ width___ exp.time_
  3 omega  -14.00   21.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4081  -99.0000  -90.0000 35

#__ type_ start__ end____ width___ exp.time_
  4 omega  -25.00   61.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       21.5018  -99.0000 -120.0000 86
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0153861000
_diffrn_orient_matrix_UB_12      -0.0038454000
_diffrn_orient_matrix_UB_13      -0.0584449000
_diffrn_orient_matrix_UB_21      -0.0328131000
_diffrn_orient_matrix_UB_22      -0.0315899000
_diffrn_orient_matrix_UB_23      -0.0004008000
_diffrn_orient_matrix_UB_31      -0.1055646000
_diffrn_orient_matrix_UB_32      0.0091471000
_diffrn_orient_matrix_UB_33      -0.0259481000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2843
_reflns_number_total             3480
_reflns_odcompleteness_completeness 96.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0767
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0780P)²+2.2421P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1865
_refine_ls_wR_factor_ref         0.1980
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.4456(3) 0.20134(9) 0.35200(17) 0.0222(4) Uani 1 1 d . . .
H4 H 0.3382 0.1868 0.3072 0.033 Uiso 1 1 calc R . .
O1 O 1.1109(3) 0.35289(8) 0.72248(17) 0.0211(4) Uani 1 1 d . . .
O2 O 0.5585(3) 0.41866(9) 0.06272(17) 0.0246(5) Uani 1 1 d . . .
O3 O 0.2176(3) 0.24517(10) 0.44219(18) 0.0271(5) Uani 1 1 d . . .
N1 N 0.7618(3) 0.35554(10) 0.62783(19) 0.0167(5) Uani 1 1 d . . .
C14 C 0.5526(4) 0.39792(12) 0.1743(2) 0.0193(5) Uani 1 1 d . . .
C12 C 0.7606(4) 0.36566(12) 0.3705(2) 0.0195(5) Uani 1 1 d . . .
H12 H 0.8917 0.3584 0.4233 0.023 Uiso 1 1 calc R . .
C15 C 0.3694(4) 0.38744(12) 0.2110(2) 0.0206(6) Uani 1 1 d . . .
H15 H 0.2383 0.3945 0.1582 0.025 Uiso 1 1 calc R . .
C5 C 0.9497(4) 0.32542(12) 0.6627(2) 0.0174(5) Uani 1 1 d . . .
C7 C 0.7407(4) 0.42193(12) 0.6713(2) 0.0195(5) Uani 1 1 d . . .
C11 C 0.5785(4) 0.35473(11) 0.4088(2) 0.0169(5) Uani 1 1 d . . .
C13 C 0.7488(4) 0.38727(13) 0.2549(2) 0.0211(6) Uani 1 1 d . . .
H13 H 0.8714 0.3947 0.2312 0.025 Uiso 1 1 calc R . .
C6 C 0.3962(4) 0.23389(12) 0.4387(2) 0.0188(5) Uani 1 1 d . . .
C1 C 0.5846(4) 0.32883(12) 0.5337(2) 0.0171(5) Uani 1 1 d . . .
H1 H 0.4545 0.3423 0.5526 0.021 Uiso 1 1 calc R . .
C2 C 0.5864(4) 0.25653(12) 0.5364(2) 0.0172(5) Uani 1 1 d . . .
H2 H 0.5647 0.2437 0.6141 0.021 Uiso 1 1 calc R . .
C3 C 0.7986(4) 0.23113(12) 0.5303(2) 0.0185(5) Uani 1 1 d . . .
H3A H 0.8293 0.2441 0.4559 0.022 Uiso 1 1 calc R . .
H3B H 0.7977 0.1858 0.5329 0.022 Uiso 1 1 calc R . .
C16 C 0.3846(4) 0.36624(12) 0.3277(2) 0.0196(5) Uani 1 1 d . . .
H16 H 0.2621 0.3596 0.3519 0.023 Uiso 1 1 calc R . .
C10 C 0.5106(4) 0.44397(12) 0.6310(3) 0.0220(6) Uani 1 1 d . . .
H10A H 0.4637 0.4432 0.5447 0.033 Uiso 1 1 calc R . .
H10B H 0.5005 0.4858 0.6591 0.033 Uiso 1 1 calc R . .
H10C H 0.4241 0.4167 0.6640 0.033 Uiso 1 1 calc R . .
C4 C 0.9644(4) 0.25673(12) 0.6378(2) 0.0188(5) Uani 1 1 d . . .
H4A H 0.9554 0.2337 0.7089 0.023 Uiso 1 1 calc R . .
H4B H 1.1020 0.2485 0.6251 0.023 Uiso 1 1 calc R . .
C9 C 0.8786(4) 0.46697(13) 0.6213(3) 0.0233(6) Uani 1 1 d . . .
H9A H 1.0229 0.4540 0.6477 0.035 Uiso 1 1 calc R . .
H9B H 0.8646 0.5085 0.6499 0.035 Uiso 1 1 calc R . .
H9C H 0.8346 0.4666 0.5349 0.035 Uiso 1 1 calc R . .
C17 C 0.3597(5) 0.42992(14) -0.0215(2) 0.0253(6) Uani 1 1 d . . .
H17A H 0.3818 0.4418 -0.0977 0.038 Uiso 1 1 calc R . .
H17B H 0.2876 0.4629 0.0080 0.038 Uiso 1 1 calc R . .
H17C H 0.2762 0.3925 -0.0312 0.038 Uiso 1 1 calc R . .
C8 C 0.8023(5) 0.42190(14) 0.8101(2) 0.0255(6) Uani 1 1 d . . .
H8A H 0.7158 0.3926 0.8385 0.038 Uiso 1 1 calc R . .
H8B H 0.7820 0.4630 0.8388 0.038 Uiso 1 1 calc R . .
H8C H 0.9474 0.4101 0.8394 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
O4 C6 1.324(3) . ?
O1 C5 1.251(3) . ?
O2 C14 1.368(3) . ?
O2 C17 1.432(3) . ?
O3 C6 1.211(3) . ?
N1 C5 1.359(3) . ?
N1 C7 1.524(3) . ?
N1 C1 1.484(3) . ?
C14 C15 1.395(4) . ?
C14 C13 1.399(4) . ?
C12 C11 1.400(4) . ?
C12 C13 1.390(4) . ?
C15 C16 1.395(4) . ?
C5 C4 1.505(4) . ?
C7 C10 1.538(4) . ?
C7 C9 1.535(4) . ?
C7 C8 1.541(4) . ?
C11 C1 1.531(3) . ?
C11 C16 1.393(4) . ?
C6 C2 1.528(3) . ?
C1 C2 1.547(3) . ?
C2 C3 1.517(4) . ?
C3 C4 1.522(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
C14 O2 C17 116.5(2) . . ?
C5 N1 C7 119.9(2) . . ?
C5 N1 C1 121.0(2) . . ?
C1 N1 C7 118.5(2) . . ?
O2 C14 C15 125.0(2) . . ?
O2 C14 C13 115.4(2) . . ?
C15 C14 C13 119.6(2) . . ?
C13 C12 C11 121.1(2) . . ?
C16 C15 C14 119.5(2) . . ?
O1 C5 N1 121.1(2) . . ?
O1 C5 C4 118.4(2) . . ?
N1 C5 C4 120.4(2) . . ?
N1 C7 C10 110.7(2) . . ?
N1 C7 C9 110.4(2) . . ?
N1 C7 C8 108.5(2) . . ?
C10 C7 C8 106.6(2) . . ?
C9 C7 C10 109.1(2) . . ?
C9 C7 C8 111.5(2) . . ?
C12 C11 C1 122.7(2) . . ?
C16 C11 C12 118.1(2) . . ?
C16 C11 C1 119.2(2) . . ?
C12 C13 C14 120.1(2) . . ?
O4 C6 C2 114.0(2) . . ?
O3 C6 O4 124.0(2) . . ?
O3 C6 C2 122.0(2) . . ?
N1 C1 C11 111.7(2) . . ?
N1 C1 C2 111.7(2) . . ?
C11 C1 C2 112.3(2) . . ?
C6 C2 C1 107.6(2) . . ?
C3 C2 C6 116.1(2) . . ?
C3 C2 C1 111.1(2) . . ?
C2 C3 C4 108.0(2) . . ?
C11 C16 C15 121.7(2) . . ?
C5 C4 C3 115.9(2) . . ?

####################################################################### 
# 
# 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_dvd71c
_database_code_depnum_ccdc_archive 'CCDC 1447518'
_audit_update_record             
;
2016-01-15 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;
_audit_creation_date             2016-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 N O4'
_chemical_formula_sum            'C15 H19 N O4'
_chemical_formula_weight         277.31
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H19 N O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.62011(17)
_cell_length_b                   11.1647(2)
_cell_length_c                   11.78218(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1397.02(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10701
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.6780
_cell_measurement_theta_min      3.1600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.3
_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  0.0330
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21624
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_min         2.647
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -47.00   47.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031   38.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega  -59.00   46.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4031   19.0000  120.0000 105

#__ type_ start__ end____ width___ exp.time_
  3 omega   -7.00   93.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3406   77.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
  4 omega   22.00   65.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3406  -99.0000   90.0000 43

#__ type_ start__ end____ width___ exp.time_
  5 omega   -7.00   92.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3406   77.0000 -180.0000 99

#__ type_ start__ end____ width___ exp.time_
  6 omega   -7.00   92.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3406   77.0000   60.0000 99

#__ type_ start__ end____ width___ exp.time_
  7 omega  -12.00   65.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3406  -99.0000 -120.0000 77

#__ type_ start__ end____ width___ exp.time_
  8 omega   -1.00   63.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3406  -99.0000    0.0000 64

#__ type_ start__ end____ width___ exp.time_
  9 omega  -40.00   51.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3406  -19.0000 -120.0000 91
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0402486000
_diffrn_orient_matrix_UB_12      0.0496394000
_diffrn_orient_matrix_UB_13      0.0101171000
_diffrn_orient_matrix_UB_21      0.0475120000
_diffrn_orient_matrix_UB_22      0.0272150000
_diffrn_orient_matrix_UB_23      0.0334836000
_diffrn_orient_matrix_UB_31      0.0241905000
_diffrn_orient_matrix_UB_32      0.0288599000
_diffrn_orient_matrix_UB_33      -0.0489679000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3128
_reflns_number_total             3198
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0265
_refine_ls_restrained_S_all      1.032
_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)+(0.0398P)²+0.2490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0692
_refine_ls_wR_factor_ref         0.0699
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_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:
 C1(H1), C2(H2), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C13(H13), C14(H14)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C15(H15A,H15B,H15C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.51333(9) 0.87493(10) 0.61444(9) 0.0189(2) Uani 1 1 d . . . . .
O2 O 0.73634(11) 1.07996(11) 0.26700(10) 0.0274(3) Uani 1 1 d . . . . .
O3 O 0.92696(10) 0.99804(10) 0.29691(9) 0.0198(2) Uani 1 1 d . . . . .
H3 H 0.9459 1.0360 0.2378 0.030 Uiso 1 1 calc GR . . . .
O4 O 0.54429(10) 0.73021(11) -0.03736(9) 0.0219(2) Uani 1 1 d . . . . .
N1 N 0.65419(11) 0.78315(11) 0.49483(10) 0.0150(3) Uani 1 1 d . . . . .
C1 C 0.74441(12) 0.81271(12) 0.40423(11) 0.0147(3) Uani 1 1 d . . . . .
H1 H 0.8243 0.7668 0.4158 0.018 Uiso 1 1 calc R . . . .
C2 C 0.76793(14) 0.94921(13) 0.42800(12) 0.0167(3) Uani 1 1 d . . . . .
H2 H 0.8373 0.9565 0.4850 0.020 Uiso 1 1 calc R . . . .
C3 C 0.64537(14) 0.99149(13) 0.48335(13) 0.0198(3) Uani 1 1 d . . . . .
H3A H 0.6616 1.0551 0.5401 0.024 Uiso 1 1 calc R . . . .
H3B H 0.5855 1.0220 0.4258 0.024 Uiso 1 1 calc R . . . .
C4 C 0.59578(13) 0.87900(13) 0.53938(12) 0.0161(3) Uani 1 1 d . . . . .
C5 C 0.63510(13) 0.66102(13) 0.53900(12) 0.0168(3) Uani 1 1 d . . . . .
H5 H 0.5638 0.6642 0.5943 0.020 Uiso 1 1 calc R . . . .
C6 C 0.59930(15) 0.57181(14) 0.44633(13) 0.0225(3) Uani 1 1 d . . . . .
H6A H 0.5252 0.6013 0.4054 0.034 Uiso 1 1 calc GR . . . .
H6B H 0.5800 0.4941 0.4808 0.034 Uiso 1 1 calc GR . . . .
H6C H 0.6697 0.5628 0.3933 0.034 Uiso 1 1 calc GR . . . .
C7 C 0.75256(14) 0.62107(14) 0.60405(13) 0.0226(3) Uani 1 1 d . . . . .
H7A H 0.8225 0.6101 0.5508 0.034 Uiso 1 1 calc GR . . . .
H7B H 0.7353 0.5452 0.6429 0.034 Uiso 1 1 calc GR . . . .
H7C H 0.7751 0.6823 0.6601 0.034 Uiso 1 1 calc GR . . . .
C8 C 0.80594(14) 1.01727(13) 0.32205(13) 0.0181(3) Uani 1 1 d . . . . .
C9 C 0.69210(13) 0.78700(12) 0.28660(12) 0.0149(3) Uani 1 1 d . . . . .
C10 C 0.77023(13) 0.74230(12) 0.20178(12) 0.0165(3) Uani 1 1 d . . . . .
H10 H 0.8559 0.7256 0.2187 0.020 Uiso 1 1 calc R . . . .
C11 C 0.72500(13) 0.72140(13) 0.09193(12) 0.0172(3) Uani 1 1 d . . . . .
H11 H 0.7796 0.6911 0.0349 0.021 Uiso 1 1 calc R . . . .
C12 C 0.59937(13) 0.74534(13) 0.06710(12) 0.0170(3) Uani 1 1 d . . . . .
C13 C 0.51980(14) 0.78860(15) 0.15182(13) 0.0207(3) Uani 1 1 d . . . . .
H13 H 0.4337 0.8037 0.1353 0.025 Uiso 1 1 calc R . . . .
C14 C 0.56602(14) 0.80957(14) 0.25994(13) 0.0202(3) Uani 1 1 d . . . . .
H14 H 0.5112 0.8398 0.3169 0.024 Uiso 1 1 calc R . . . .
C15 C 0.61821(15) 0.67317(15) -0.12320(13) 0.0226(3) Uani 1 1 d . . . . .
H15A H 0.5688 0.6669 -0.1932 0.034 Uiso 1 1 calc GR . . . .
H15B H 0.6423 0.5929 -0.0976 0.034 Uiso 1 1 calc GR . . . .
H15C H 0.6942 0.7207 -0.1376 0.034 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.2454(17) . ?
O2 C8 1.2070(19) . ?
O3 H3 0.8400 . ?
O3 C8 1.3363(18) . ?
O4 C12 1.3732(17) . ?
O4 C15 1.4299(18) . ?
N1 C1 1.4719(17) . ?
N1 C4 1.3437(19) . ?
N1 C5 1.4735(18) . ?
C1 H1 1.0000 . ?
C1 C2 1.5695(19) . ?
C1 C9 1.5204(19) . ?
C2 H2 1.0000 . ?
C2 C3 1.530(2) . ?
C2 C8 1.516(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.513(2) . ?
C5 H5 1.0000 . ?
C5 C6 1.526(2) . ?
C5 C7 1.531(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C9 C10 1.3915(19) . ?
C9 C14 1.398(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.400(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(2) . ?
C12 C13 1.394(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.385(2) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O3 H3 109.5 . . ?
C12 O4 C15 117.06(11) . . ?
C1 N1 C5 123.59(11) . . ?
C4 N1 C1 113.91(12) . . ?
C4 N1 C5 122.38(12) . . ?
N1 C1 H1 109.8 . . ?
N1 C1 C2 101.06(11) . . ?
N1 C1 C9 112.39(11) . . ?
C2 C1 H1 109.8 . . ?
C9 C1 H1 109.8 . . ?
C9 C1 C2 113.84(11) . . ?
C1 C2 H2 108.4 . . ?
C3 C2 C1 103.90(11) . . ?
C3 C2 H2 108.4 . . ?
C8 C2 C1 112.46(11) . . ?
C8 C2 H2 108.4 . . ?
C8 C2 C3 115.00(12) . . ?
C2 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C4 C3 C2 103.05(11) . . ?
C4 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
O1 C4 N1 124.96(14) . . ?
O1 C4 C3 125.78(13) . . ?
N1 C4 C3 109.26(12) . . ?
N1 C5 H5 107.5 . . ?
N1 C5 C6 112.68(12) . . ?
N1 C5 C7 109.53(12) . . ?
C6 C5 H5 107.5 . . ?
C6 C5 C7 111.79(13) . . ?
C7 C5 H5 107.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 O3 124.27(14) . . ?
O2 C8 C2 124.75(14) . . ?
O3 C8 C2 110.98(13) . . ?
C10 C9 C1 120.30(12) . . ?
C10 C9 C14 118.31(13) . . ?
C14 C9 C1 121.38(12) . . ?
C9 C10 H10 119.4 . . ?
C9 C10 C11 121.27(13) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.3 . . ?
C12 C11 C10 119.42(13) . . ?
C12 C11 H11 120.3 . . ?
O4 C12 C11 124.97(13) . . ?
O4 C12 C13 115.22(12) . . ?
C11 C12 C13 119.81(13) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.14(13) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 119.5 . . ?
C13 C14 C9 121.03(14) . . ?
C13 C14 H14 119.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_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_dvd76c
_database_code_depnum_ccdc_archive 'CCDC 1447521'
_audit_update_record             
;
2016-01-15 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;
_audit_creation_date             2016-01-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H17 N O3'
_chemical_formula_sum            'C14 H17 N O3'
_chemical_formula_weight         247.28
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H13 N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   5.9545(5)
_cell_length_b                   10.6290(8)
_cell_length_c                   10.1521(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.878(7)
_cell_angle_gamma                90
_cell_volume                     634.84(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1920
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.8270
_cell_measurement_theta_min      3.8350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81220
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             264
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.25
_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  0.0341
_diffrn_reflns_av_unetI/netI     0.0506
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5642
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         2.792
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -93.00   31.00   1.0000    5.6300
omega____ theta____ kappa____ phi______ frames
    -      -22.4081    0.0000 -120.0000 124

#__ type_ start__ end____ width___ exp.time_
  2 omega  -98.00  -68.00   1.0000    5.6300
omega____ theta____ kappa____ phi______ frames
    -      -22.4081 -178.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
  3 omega  -81.00  -54.00   1.0000    5.6300
omega____ theta____ kappa____ phi______ frames
    -      -22.4081 -178.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega    8.00   65.00   1.0000    5.6300
omega____ theta____ kappa____ phi______ frames
    -       23.3456  -99.0000 -150.0000 57

#__ type_ start__ end____ width___ exp.time_
  5 omega  -76.00  -26.00   1.0000    5.6300
omega____ theta____ kappa____ phi______ frames
    -      -22.4081  119.0000 -135.0000 50

#__ type_ start__ end____ width___ exp.time_
  6 omega    4.00   77.00   1.0000    5.6300
omega____ theta____ kappa____ phi______ frames
    -       23.3456   57.0000 -150.0000 73

#__ type_ start__ end____ width___ exp.time_
  7 omega   -2.00   93.00   1.0000    5.6300
omega____ theta____ kappa____ phi______ frames
    -       23.3456    0.0000 -150.0000 95
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0114048000
_diffrn_orient_matrix_UB_12      -0.0662222000
_diffrn_orient_matrix_UB_13      -0.0070568000
_diffrn_orient_matrix_UB_21      0.1000089000
_diffrn_orient_matrix_UB_22      -0.0020691000
_diffrn_orient_matrix_UB_23      -0.0298458000
_diffrn_orient_matrix_UB_31      0.0663442000
_diffrn_orient_matrix_UB_32      -0.0083271000
_diffrn_orient_matrix_UB_33      0.0636811000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.992
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2542
_reflns_number_total             2768
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_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, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0635P)²+0.0015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1147
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_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:
 C1(H1), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
2.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C14(H14A,H14B,H14C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.3879(4) 0.31058(19) 0.42534(19) 0.0207(4) Uani 1 1 d . . . . .
O2 O 0.0889(4) 0.59221(19) 0.7726(2) 0.0235(5) Uani 1 1 d . . . . .
O3 O 0.4365(4) 0.5396(2) 0.7313(2) 0.0249(5) Uani 1 1 d . . . . .
H3 H 0.4783 0.5878 0.7933 0.037 Uiso 1 1 calc GR . . . .
N1 N -0.0331(4) 0.2602(2) 0.5323(2) 0.0177(5) Uani 1 1 d . . . . .
C1 C 0.1814(4) 0.3183(2) 0.5942(3) 0.0170(6) Uani 1 1 d . . . . .
H1 H 0.2989 0.2988 0.5395 0.020 Uiso 1 1 calc R . . . .
C2 C 0.1263(5) 0.4629(3) 0.5814(3) 0.0171(6) Uani 1 1 d . . . . .
H2 H 0.2010 0.4963 0.5093 0.021 Uiso 1 1 calc R . . . .
C3 C -0.1314(5) 0.4722(3) 0.5366(3) 0.0192(6) Uani 1 1 d . . . . .
H3A H -0.2080 0.4973 0.6101 0.023 Uiso 1 1 calc R . . . .
H3B H -0.1667 0.5325 0.4647 0.023 Uiso 1 1 calc R . . . .
C4 C -0.2004(5) 0.3416(3) 0.4901(3) 0.0178(6) Uani 1 1 d . . . . .
C5 C -0.0433(5) 0.1279(3) 0.4942(3) 0.0224(6) Uani 1 1 d . . . . .
H5A H -0.2010 0.1030 0.4704 0.027 Uiso 1 1 calc R . . . .
H5B H 0.0231 0.0774 0.5699 0.027 Uiso 1 1 calc R . . . .
C6 C 0.0821(6) 0.1016(3) 0.3771(3) 0.0260(7) Uani 1 1 d . . . . .
H6A H 0.0232 0.1551 0.3037 0.039 Uiso 1 1 calc GR . . . .
H6B H 0.0607 0.0152 0.3508 0.039 Uiso 1 1 calc GR . . . .
H6C H 0.2413 0.1180 0.4032 0.039 Uiso 1 1 calc GR . . . .
C7 C 0.2102(5) 0.5381(3) 0.7060(3) 0.0177(6) Uani 1 1 d . . . . .
C8 C 0.2578(5) 0.2680(3) 0.7339(3) 0.0173(6) Uani 1 1 d . . . . .
C9 C 0.4738(5) 0.2152(3) 0.7659(3) 0.0199(6) Uani 1 1 d . . . . .
H9 H 0.5680 0.2100 0.7011 0.024 Uiso 1 1 calc R . . . .
C10 C 0.5502(5) 0.1704(3) 0.8939(3) 0.0230(6) Uani 1 1 d . . . . .
H10 H 0.6945 0.1351 0.9130 0.028 Uiso 1 1 calc R . . . .
C11 C 0.4145(5) 0.1773(3) 0.9936(3) 0.0217(6) Uani 1 1 d . . . . .
C12 C 0.1976(5) 0.2298(3) 0.9611(3) 0.0205(6) Uani 1 1 d . . . . .
H12 H 0.1036 0.2354 1.0260 0.025 Uiso 1 1 calc R . . . .
C13 C 0.1204(5) 0.2741(3) 0.8327(3) 0.0193(6) Uani 1 1 d . . . . .
H13 H -0.0248 0.3080 0.8130 0.023 Uiso 1 1 calc R . . . .
C14 C 0.4972(6) 0.1278(3) 1.1317(3) 0.0307(7) Uani 1 1 d . . . . .
H14A H 0.6492 0.0962 1.1359 0.046 Uiso 1 1 calc GR . . . .
H14B H 0.3991 0.0611 1.1518 0.046 Uiso 1 1 calc GR . . . .
H14C H 0.4959 0.1945 1.1954 0.046 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.249(3) . ?
O2 C7 1.208(4) . ?
O3 H3 0.8200 . ?
O3 C7 1.332(3) . ?
N1 C1 1.470(3) . ?
N1 C4 1.339(4) . ?
N1 C5 1.457(4) . ?
C1 H1 0.9800 . ?
C1 C2 1.572(4) . ?
C1 C8 1.518(4) . ?
C2 H2 0.9800 . ?
C2 C3 1.535(4) . ?
C2 C7 1.515(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.503(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.524(4) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 C9 1.395(4) . ?
C8 C13 1.390(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.393(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(4) . ?
C11 C12 1.399(4) . ?
C11 C14 1.507(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.395(4) . ?
C13 H13 0.9300 . ?
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
C7 O3 H3 109.5 . . ?
C4 N1 C1 114.8(2) . . ?
C4 N1 C5 122.7(2) . . ?
C5 N1 C1 121.1(2) . . ?
N1 C1 H1 108.5 . . ?
N1 C1 C2 102.6(2) . . ?
N1 C1 C8 111.5(2) . . ?
C2 C1 H1 108.5 . . ?
C8 C1 H1 108.5 . . ?
C8 C1 C2 116.7(2) . . ?
C1 C2 H2 107.6 . . ?
C3 C2 C1 105.9(2) . . ?
C3 C2 H2 107.6 . . ?
C7 C2 C1 114.2(2) . . ?
C7 C2 H2 107.6 . . ?
C7 C2 C3 113.5(2) . . ?
C2 C3 H3A 110.9 . . ?
C2 C3 H3B 110.9 . . ?
H3A C3 H3B 108.9 . . ?
C4 C3 C2 104.2(2) . . ?
C4 C3 H3A 110.9 . . ?
C4 C3 H3B 110.9 . . ?
O1 C4 N1 123.9(3) . . ?
O1 C4 C3 126.0(3) . . ?
N1 C4 C3 110.0(2) . . ?
N1 C5 H5A 109.2 . . ?
N1 C5 H5B 109.2 . . ?
N1 C5 C6 112.2(2) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O2 C7 O3 124.1(2) . . ?
O2 C7 C2 124.7(3) . . ?
O3 C7 C2 111.1(2) . . ?
C9 C8 C1 119.5(2) . . ?
C13 C8 C1 122.2(3) . . ?
C13 C8 C9 118.4(2) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 C12 117.9(3) . . ?
C10 C11 C14 121.0(3) . . ?
C12 C11 C14 121.1(3) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.5 . . ?
C8 C13 C12 120.8(3) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
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 . . ?

_shelx_SHELXL_version_number     2014/7
_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_dvd-71-t
_database_code_depnum_ccdc_archive 'CCDC 1452491'
_audit_update_record             
;
2016-02-10 deposited with the CCDC.
2016-05-11 downloaded from the CCDC.
;
_audit_creation_date             2016-02-10
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H19 N O4'
_chemical_formula_sum            'C15 H19 N O4'
_chemical_formula_weight         277.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 N3 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 '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                   9.771(3)
_cell_length_b                   14.4414(16)
_cell_length_c                   10.4314(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.145(17)
_cell_angle_gamma                90.00
_cell_volume                     1406.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2952
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      29.9780
_cell_measurement_theta_min      3.5590
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8394
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.88
_diffrn_ambient_temperature      100.0(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.9652
_diffrn_measured_fraction_theta_max 0.8478
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -80.00    1.00   1.0000    3.8200
omega____ theta____ kappa____ phi______ frames
    -      -20.5643  -38.0000  150.0000 81

#__ type_ start__ end____ width___ exp.time_
  2 omega  -84.00   -2.00   1.0000    3.8200
omega____ theta____ kappa____ phi______ frames
    -      -20.5643  -57.0000  -90.0000 82

#__ type_ start__ end____ width___ exp.time_
  3 omega  -25.00   15.00   1.0000    3.8200
omega____ theta____ kappa____ phi______ frames
    -      -20.5643  -99.0000 -120.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega  -28.00   45.00   1.0000    3.8200
omega____ theta____ kappa____ phi______ frames
    -      -20.5643   57.0000  -30.0000 73

#__ type_ start__ end____ width___ exp.time_
  5 omega  -50.00  -25.00   1.0000    3.8200
omega____ theta____ kappa____ phi______ frames
    -      -20.5643   77.0000 -120.0000 25
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0159776000
_diffrn_orient_matrix_UB_12      0.0029022000
_diffrn_orient_matrix_UB_13      0.0707634000
_diffrn_orient_matrix_UB_21      0.0742333000
_diffrn_orient_matrix_UB_22      -0.0014915000
_diffrn_orient_matrix_UB_23      0.0063724000
_diffrn_orient_matrix_UB_31      0.0011728000
_diffrn_orient_matrix_UB_32      0.0490555000
_diffrn_orient_matrix_UB_33      -0.0040666000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2727
_reflns_number_total             3138
_reflns_odcompleteness_completeness 96.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.025
_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)+(0.0456P)²+0.5411P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0988
_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. 
;
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.99011(10) 0.01451(6) 0.30795(9) 0.0159(2) Uani 1 1 d . . .
O2 O 1.05954(11) 0.39386(6) 0.39307(9) 0.0192(2) Uani 1 1 d . . .
H2 H 1.0359 0.4288 0.3283 0.029 Uiso 1 1 calc R . .
O3 O 0.97069(11) 0.28523(6) 0.23668(9) 0.0206(2) Uani 1 1 d . . .
O4 O 1.60206(10) 0.11698(6) 0.98917(8) 0.0168(2) Uani 1 1 d . . .
N1 N 1.18501(11) 0.11051(6) 0.39172(10) 0.0116(2) Uani 1 1 d . . .
C11 C 1.54094(14) 0.21601(8) 0.78894(12) 0.0149(3) Uani 1 1 d . . .
H11 H 1.6213 0.2532 0.8221 0.018 Uiso 1 1 calc R . .
C10 C 1.44543(13) 0.23300(8) 0.66151(12) 0.0139(2) Uani 1 1 d . . .
H10 H 1.4639 0.2814 0.6102 0.017 Uiso 1 1 calc R . .
C3 C 0.97411(13) 0.15270(8) 0.43737(12) 0.0120(2) Uani 1 1 d . . .
H3A H 0.9632 0.1271 0.5197 0.014 Uiso 1 1 calc R . .
H3B H 0.8803 0.1690 0.3785 0.014 Uiso 1 1 calc R . .
C9 C 1.32359(13) 0.17895(8) 0.61030(11) 0.0119(2) Uani 1 1 d . . .
C1 C 1.22351(13) 0.19695(8) 0.47002(11) 0.0117(2) Uani 1 1 d . . .
H1 H 1.2703 0.2393 0.4226 0.014 Uiso 1 1 calc R . .
C2 C 1.07311(13) 0.23744(8) 0.46669(12) 0.0115(2) Uani 1 1 d . . .
H2A H 1.0759 0.2659 0.5527 0.014 Uiso 1 1 calc R . .
C12 C 1.51446(13) 0.14278(8) 0.86556(12) 0.0132(2) Uani 1 1 d . . .
C8 C 1.31801(15) -0.03930(9) 0.41248(13) 0.0187(3) Uani 1 1 d . . .
H8A H 1.3387 -0.0347 0.5081 0.028 Uiso 1 1 calc R . .
H8B H 1.3966 -0.0688 0.3912 0.028 Uiso 1 1 calc R . .
H8C H 1.2326 -0.0753 0.3767 0.028 Uiso 1 1 calc R . .
C7 C 1.26187(15) 0.05594(9) 0.19821(13) 0.0181(3) Uani 1 1 d . . .
H7A H 1.1768 0.0201 0.1605 0.027 Uiso 1 1 calc R . .
H7B H 1.3405 0.0285 0.1743 0.027 Uiso 1 1 calc R . .
H7C H 1.2470 0.1180 0.1640 0.027 Uiso 1 1 calc R . .
C6 C 1.29587(13) 0.05788(8) 0.35081(12) 0.0141(2) Uani 1 1 d . . .
H6 H 1.3864 0.0914 0.3860 0.017 Uiso 1 1 calc R . .
C13 C 1.39039(13) 0.08927(8) 0.81669(12) 0.0149(3) Uani 1 1 d . . .
H13 H 1.3709 0.0417 0.8688 0.018 Uiso 1 1 calc R . .
C14 C 1.29637(13) 0.10714(8) 0.69041(12) 0.0142(2) Uani 1 1 d . . .
H14 H 1.2144 0.0711 0.6585 0.017 Uiso 1 1 calc R . .
C15 C 1.73783(15) 0.16283(10) 1.03771(14) 0.0235(3) Uani 1 1 d . . .
H15A H 1.7892 0.1572 0.9725 0.035 Uiso 1 1 calc R . .
H15B H 1.7924 0.1348 1.1204 0.035 Uiso 1 1 calc R . .
H15C H 1.7228 0.2271 1.0526 0.035 Uiso 1 1 calc R . .
C5 C 1.02741(13) 0.30712(8) 0.35236(12) 0.0124(2) Uani 1 1 d . . .
C4 C 1.04814(13) 0.08450(8) 0.37002(11) 0.0120(2) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C4 1.2434(14) . ?
O2 H2 0.8200 . ?
O2 C5 1.3303(14) . ?
O3 C5 1.2120(15) . ?
O4 C12 1.3723(15) . ?
O4 C15 1.4349(17) . ?
N1 C1 1.4784(14) . ?
N1 C6 1.4852(15) . ?
N1 C4 1.3426(16) . ?
C11 H11 0.9300 . ?
C11 C10 1.4024(17) . ?
C11 C12 1.3950(17) . ?
C10 H10 0.9300 . ?
C10 C9 1.3918(17) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.5337(16) . ?
C3 C4 1.5121(16) . ?
C9 C1 1.5236(16) . ?
C9 C14 1.4055(16) . ?
C1 H1 0.9800 . ?
C1 C2 1.5726(17) . ?
C2 H2A 0.9800 . ?
C2 C5 1.5233(16) . ?
C12 C13 1.4009(18) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C8 C6 1.5324(16) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C7 C6 1.5275(17) . ?
C6 H6 0.9800 . ?
C13 H13 0.9300 . ?
C13 C14 1.3901(17) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C5 O2 H2 109.5 . . ?
C12 O4 C15 117.52(10) . . ?
C1 N1 C6 120.16(10) . . ?
C4 N1 C1 114.08(9) . . ?
C4 N1 C6 125.67(10) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C12 C11 C10 119.46(11) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 C11 121.37(11) . . ?
C9 C10 H10 119.3 . . ?
H3A C3 H3B 108.9 . . ?
C2 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
C4 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C4 C3 C2 104.62(10) . . ?
C10 C9 C1 120.47(10) . . ?
C10 C9 C14 118.43(11) . . ?
C14 C9 C1 121.10(10) . . ?
N1 C1 C9 111.92(9) . . ?
N1 C1 H1 109.2 . . ?
N1 C1 C2 102.58(9) . . ?
C9 C1 H1 109.2 . . ?
C9 C1 C2 114.56(9) . . ?
C2 C1 H1 109.2 . . ?
C3 C2 C1 103.78(9) . . ?
C3 C2 H2A 111.3 . . ?
C1 C2 H2A 111.3 . . ?
C5 C2 C3 110.41(10) . . ?
C5 C2 C1 108.62(9) . . ?
C5 C2 H2A 111.3 . . ?
O4 C12 C11 125.06(11) . . ?
O4 C12 C13 115.18(11) . . ?
C11 C12 C13 119.76(11) . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
N1 C6 C8 111.88(10) . . ?
N1 C6 C7 110.85(10) . . ?
N1 C6 H6 107.1 . . ?
C8 C6 H6 107.1 . . ?
C7 C6 C8 112.40(10) . . ?
C7 C6 H6 107.1 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.12(11) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 H14 119.6 . . ?
C13 C14 C9 120.82(11) . . ?
C13 C14 H14 119.6 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C5 C2 112.64(10) . . ?
O3 C5 O2 123.99(11) . . ?
O3 C5 C2 123.35(11) . . ?
O1 C4 N1 126.44(11) . . ?
O1 C4 C3 124.35(11) . . ?
N1 C4 C3 109.19(10) . . ?

