# 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_uny120
_database_code_depnum_ccdc_archive 'CCDC 1470615'
_audit_update_record             
;
2016-03-25 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;
_audit_creation_date             2016-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H21 N O3'
_chemical_formula_sum            'C20 H21 N O3'
_chemical_formula_weight         323.38
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H21 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                   6.1741(3)
_cell_length_b                   22.3708(7)
_cell_length_c                   12.6253(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.267(4)
_cell_angle_gamma                90
_cell_volume                     1697.25(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2416
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.0321
_cell_measurement_theta_min      2.7260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93749
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7371
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.196
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -99.00  -74.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  178.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -79.00   22.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -19.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
  3 omega  -48.00   43.00   1.0000  170.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   38.0000  150.0000 91
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0716010000
_diffrn_orient_matrix_UB_12      0.0082269000
_diffrn_orient_matrix_UB_13      0.0342084000
_diffrn_orient_matrix_UB_21      -0.0861687000
_diffrn_orient_matrix_UB_22      0.0060156000
_diffrn_orient_matrix_UB_23      -0.0464800000
_diffrn_orient_matrix_UB_31      -0.0369584000
_diffrn_orient_matrix_UB_32      -0.0300343000
_diffrn_orient_matrix_UB_33      0.0000532000
_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                3151
_reflns_number_total             3881
_reflns_odcompleteness_completeness 99.53
_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 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_computing_structure_solution    ?
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.045
_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     219
_refine_ls_number_reflns         3881
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      1.031
_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)+(0.0385P)²+0.7152P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0942
_refine_ls_wR_factor_ref         0.1010
_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 Riding coordinates:
 O3(H3)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.d Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.67531(17) 0.35242(4) 0.41745(8) 0.0194(2) Uani 1 1 d . . . . .
O2 O -0.17092(17) 0.26183(5) 0.09927(8) 0.0208(2) Uani 1 1 d . . . . .
O3 O 0.03531(16) 0.19864(4) 0.02857(8) 0.0175(2) Uani 1 1 d . . . . .
H3 H -0.0883 0.1859 -0.0041 0.026 Uiso 1 1 d R . . . .
N1 N 0.36430(19) 0.35905(5) 0.27848(9) 0.0129(2) Uani 1 1 d . . . . .
C1 C 0.1959(2) 0.33570(6) 0.18193(10) 0.0120(3) Uani 1 1 d . . . . .
H1 H 0.0467 0.3378 0.2001 0.014 Uiso 1 1 calc R . . . .
C2 C 0.2356(2) 0.27007(6) 0.15386(10) 0.0116(3) Uani 1 1 d . . . . .
H2 H 0.3378 0.2703 0.1028 0.014 Uiso 1 1 calc R . . . .
C3 C 0.3488(2) 0.23171(6) 0.25484(11) 0.0132(3) Uani 1 1 d . . . . .
C4 C 0.5686(2) 0.26418(6) 0.30926(11) 0.0154(3) Uani 1 1 d . . . . .
H4A H 0.6408 0.2420 0.3759 0.018 Uiso 1 1 calc R . . . .
H4B H 0.6701 0.2628 0.2590 0.018 Uiso 1 1 calc R . . . .
C5 C 0.5400(2) 0.32819(6) 0.33918(11) 0.0140(3) Uani 1 1 d . . . . .
C6 C 0.0104(2) 0.24386(6) 0.09132(11) 0.0139(3) Uani 1 1 d . . . . .
C7 C 0.3244(2) 0.41909(6) 0.31210(11) 0.0139(3) Uani 1 1 d . . . . .
C8 C 0.1336(2) 0.43063(7) 0.34730(11) 0.0188(3) Uani 1 1 d . . . . .
H8 H 0.0288 0.3998 0.3490 0.023 Uiso 1 1 calc R . . . .
C9 C 0.0968(3) 0.48846(7) 0.38039(12) 0.0248(3) Uani 1 1 d . . . . .
H9 H -0.0364 0.4972 0.4030 0.030 Uiso 1 1 calc R . . . .
C10 C 0.2516(3) 0.53334(7) 0.38083(12) 0.0268(4) Uani 1 1 d . . . . .
H10 H 0.2264 0.5723 0.4053 0.032 Uiso 1 1 calc R . . . .
C11 C 0.4416(3) 0.52116(6) 0.34579(12) 0.0244(3) Uani 1 1 d . . . . .
H11 H 0.5484 0.5518 0.3461 0.029 Uiso 1 1 calc R . . . .
C12 C 0.4777(3) 0.46428(6) 0.30989(12) 0.0191(3) Uani 1 1 d . . . . .
H12 H 0.6073 0.4562 0.2838 0.023 Uiso 1 1 calc R . . . .
C13 C 0.1880(2) 0.37574(6) 0.08374(11) 0.0132(3) Uani 1 1 d . . . . .
C14 C -0.0165(3) 0.39153(7) 0.01323(12) 0.0208(3) Uani 1 1 d . . . . .
H14 H -0.1518 0.3781 0.0288 0.025 Uiso 1 1 calc R . . . .
C15 C -0.0229(3) 0.42638(7) -0.07862(13) 0.0267(4) Uani 1 1 d . . . . .
H15 H -0.1611 0.4366 -0.1258 0.032 Uiso 1 1 calc R . . . .
C16 C 0.1746(3) 0.44582(6) -0.10007(12) 0.0226(3) Uani 1 1 d . . . . .
H16 H 0.1727 0.4701 -0.1620 0.027 Uiso 1 1 calc R . . . .
C17 C 0.3790(3) 0.42987(6) -0.03076(12) 0.0198(3) Uani 1 1 d . . . . .
H17 H 0.5141 0.4433 -0.0467 0.024 Uiso 1 1 calc R . . . .
C18 C 0.3859(2) 0.39487(6) 0.06045(11) 0.0170(3) Uani 1 1 d . . . . .
H18 H 0.5246 0.3841 0.1066 0.020 Uiso 1 1 calc R . . . .
C19 C 0.4109(2) 0.16928(6) 0.22098(12) 0.0182(3) Uani 1 1 d . . . . .
H19A H 0.2750 0.1461 0.1933 0.027 Uiso 1 1 calc GR . . . .
H19B H 0.5030 0.1488 0.2841 0.027 Uiso 1 1 calc GR . . . .
H19C H 0.4941 0.1730 0.1639 0.027 Uiso 1 1 calc GR . . . .
C20 C 0.2000(3) 0.22557(6) 0.33391(11) 0.0188(3) Uani 1 1 d . . . . .
H20A H 0.1651 0.2653 0.3580 0.028 Uiso 1 1 calc GR . . . .
H20B H 0.2765 0.2021 0.3970 0.028 Uiso 1 1 calc GR . . . .
H20C H 0.0619 0.2053 0.2980 0.028 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 1.2608(16) . ?
O2 C6 1.2149(17) . ?
O3 H3 0.8300 . ?
O3 C6 1.3155(16) . ?
N1 C1 1.5025(16) . ?
N1 C5 1.3635(17) . ?
N1 C7 1.4469(16) . ?
C1 H1 1.0000 . ?
C1 C2 1.5430(17) . ?
C1 C13 1.5209(17) . ?
C2 H2 1.0000 . ?
C2 C3 1.5626(18) . ?
C2 C6 1.5483(18) . ?
C3 C4 1.5533(19) . ?
C3 C19 1.5346(18) . ?
C3 C20 1.5101(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5016(18) . ?
C7 C8 1.376(2) . ?
C7 C12 1.390(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.385(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.373(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.386(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.4124(19) . ?
C13 C18 1.3886(19) . ?
C14 H14 0.9500 . ?
C14 C15 1.390(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.379(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.407(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.385(2) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C6 O3 H3 110.0 . . ?
C5 N1 C1 126.37(11) . . ?
C5 N1 C7 118.19(11) . . ?
C7 N1 C1 115.34(10) . . ?
N1 C1 H1 107.5 . . ?
N1 C1 C2 113.60(10) . . ?
N1 C1 C13 110.09(10) . . ?
C2 C1 H1 107.5 . . ?
C13 C1 H1 107.5 . . ?
C13 C1 C2 110.50(10) . . ?
C1 C2 H2 107.4 . . ?
C1 C2 C3 113.59(10) . . ?
C1 C2 C6 107.83(11) . . ?
C3 C2 H2 107.4 . . ?
C6 C2 H2 107.4 . . ?
C6 C2 C3 112.91(10) . . ?
C4 C3 C2 106.61(10) . . ?
C19 C3 C2 111.48(11) . . ?
C19 C3 C4 107.48(11) . . ?
C20 C3 C2 111.30(11) . . ?
C20 C3 C4 110.62(11) . . ?
C20 C3 C19 109.27(11) . . ?
C3 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.59(11) . . ?
C5 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
O1 C5 N1 121.42(12) . . ?
O1 C5 C4 120.82(12) . . ?
N1 C5 C4 117.76(12) . . ?
O2 C6 O3 122.79(13) . . ?
O2 C6 C2 124.70(12) . . ?
O3 C6 C2 112.50(11) . . ?
C8 C7 N1 119.03(12) . . ?
C8 C7 C12 120.52(13) . . ?
C12 C7 N1 120.45(12) . . ?
C7 C8 H8 120.6 . . ?
C7 C8 C9 118.79(14) . . ?
C9 C8 H8 120.6 . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.92(15) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.66(14) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.08(15) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 120.0 . . ?
C11 C12 C7 119.98(14) . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C1 121.21(12) . . ?
C18 C13 C1 119.26(12) . . ?
C18 C13 C14 119.48(13) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.08(14) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 118.91(14) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.36(13) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.84(14) . . ?
C18 C17 H17 119.6 . . ?
C13 C18 H18 120.3 . . ?
C17 C18 C13 119.32(13) . . ?
C17 C18 H18 120.3 . . ?
C3 C19 H19A 109.5 . . ?
C3 C19 H19B 109.5 . . ?
C3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C3 C20 H20A 109.5 . . ?
C3 C20 H20B 109.5 . . ?
C3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 29.93(15) . . . . ?
N1 C1 C2 C6 155.84(10) . . . . ?
N1 C1 C13 C14 -138.14(13) . . . . ?
N1 C1 C13 C18 44.76(16) . . . . ?
N1 C7 C8 C9 179.52(12) . . . . ?
N1 C7 C12 C11 -177.78(13) . . . . ?
C1 N1 C5 O1 178.32(12) . . . . ?
C1 N1 C5 C4 -1.24(19) . . . . ?
C1 N1 C7 C8 62.53(16) . . . . ?
C1 N1 C7 C12 -118.13(13) . . . . ?
C1 C2 C3 C4 -55.90(14) . . . . ?
C1 C2 C3 C19 -172.91(11) . . . . ?
C1 C2 C3 C20 64.81(14) . . . . ?
C1 C2 C6 O2 -25.60(17) . . . . ?
C1 C2 C6 O3 155.37(11) . . . . ?
C1 C13 C14 C15 -177.69(13) . . . . ?
C1 C13 C18 C17 178.09(12) . . . . ?
C2 C1 C13 C14 95.57(15) . . . . ?
C2 C1 C13 C18 -81.54(15) . . . . ?
C2 C3 C4 C5 55.47(14) . . . . ?
C3 C2 C6 O2 100.71(15) . . . . ?
C3 C2 C6 O3 -78.32(13) . . . . ?
C3 C4 C5 O1 151.93(12) . . . . ?
C3 C4 C5 N1 -28.50(17) . . . . ?
C5 N1 C1 C2 0.30(17) . . . . ?
C5 N1 C1 C13 -124.22(13) . . . . ?
C5 N1 C7 C8 -114.05(14) . . . . ?
C5 N1 C7 C12 65.29(17) . . . . ?
C6 C2 C3 C4 -179.07(10) . . . . ?
C6 C2 C3 C19 63.91(14) . . . . ?
C6 C2 C3 C20 -58.36(14) . . . . ?
C7 N1 C1 C2 -175.94(11) . . . . ?
C7 N1 C1 C13 59.53(14) . . . . ?
C7 N1 C5 O1 -5.52(19) . . . . ?
C7 N1 C5 C4 174.91(11) . . . . ?
C7 C8 C9 C10 -1.7(2) . . . . ?
C8 C7 C12 C11 1.5(2) . . . . ?
C8 C9 C10 C11 1.6(2) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 C7 -1.7(2) . . . . ?
C12 C7 C8 C9 0.2(2) . . . . ?
C13 C1 C2 C3 154.23(11) . . . . ?
C13 C1 C2 C6 -79.85(13) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C13 C18 C17 0.9(2) . . . . ?
C14 C15 C16 C17 0.9(2) . . . . ?
C15 C16 C17 C18 -0.5(2) . . . . ?
C16 C17 C18 C13 -0.4(2) . . . . ?
C18 C13 C14 C15 -0.6(2) . . . . ?
C19 C3 C4 C5 175.11(11) . . . . ?
C20 C3 C4 C5 -65.68(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_uny076
_database_code_depnum_ccdc_archive 'CCDC 1470616'
_audit_update_record             
;
2016-03-25 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;
_audit_creation_date             2016-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 N O3'
_chemical_formula_sum            'C18 H17 N O3'
_chemical_formula_weight         295.32
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H17 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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.2973(3)
_cell_length_b                   9.6961(3)
_cell_length_c                   17.2808(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.402(3)
_cell_angle_gamma                90
_cell_volume                     1460.10(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3659
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.8700
_cell_measurement_theta_min      5.0600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.744
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             624
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9351
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.975
_diffrn_reflns_theta_min         5.075
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -42.00   27.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354   38.0000  150.0000 69

#__ type_ start__ end____ width___ exp.time_
  2 omega   73.00   99.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   96.00  122.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  138.00  166.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  125.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega  153.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega  140.00  171.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   30.0000 31

#__ type_ start__ end____ width___ exp.time_
  7 omega  114.00  141.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   95.00  144.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   61.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
  9 omega   86.00  111.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega   89.00  123.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
 11 omega   64.00   91.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   70.00  108.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000  -30.0000 38

#__ type_ start__ end____ width___ exp.time_
 13 omega  100.00  138.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -61.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
 14 omega  123.00  149.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega  140.00  178.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
 16 omega  101.00  127.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   30.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   44.00   87.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -74.0000  -45.0000 43

#__ type_ start__ end____ width___ exp.time_
 18 omega   39.00  117.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000  -30.0000 78

#__ type_ start__ end____ width___ exp.time_
 19 omega   81.00  108.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega   42.00   97.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  150.0000 55

#__ type_ start__ end____ width___ exp.time_
 21 omega   32.00   60.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 22 omega   39.00   83.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
 23 omega   50.00   82.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -125.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
 24 omega   38.00  103.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -95.0000 -180.0000 65

#__ type_ start__ end____ width___ exp.time_
 25 omega   62.00   87.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -       41.4354  178.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 26 omega -120.00  -12.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -19.0000  -30.0000 108

#__ type_ start__ end____ width___ exp.time_
 27 omega -111.00  -86.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -      -41.4354  -38.0000 -120.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0931199000
_diffrn_orient_matrix_UB_12      0.1231604000
_diffrn_orient_matrix_UB_13      -0.0391260000
_diffrn_orient_matrix_UB_21      0.1226393000
_diffrn_orient_matrix_UB_22      0.0416214000
_diffrn_orient_matrix_UB_23      -0.0456765000
_diffrn_orient_matrix_UB_31      -0.0698284000
_diffrn_orient_matrix_UB_32      -0.0911685000
_diffrn_orient_matrix_UB_33      -0.0737508000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2553
_reflns_number_total             2995
_reflns_odcompleteness_completeness 95.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     80.07
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.546
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2995
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.034
_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)+(0.0637P)²+0.4229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1185
_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 O(H) groups
2.a Riding coordinates:
 O3(H3)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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 0.36410(12) 0.82267(11) 0.48194(6) 0.0189(2) Uani 1 1 d . . . . .
O2 O 0.50700(13) 0.57327(11) 0.82982(6) 0.0219(2) Uani 1 1 d . . . . .
O3 O 0.43551(13) 0.78139(11) 0.85953(6) 0.0212(2) Uani 1 1 d . . . . .
H3 H 0.4302 0.7401 0.9012 0.032 Uiso 1 1 d R . . . .
N1 N 0.52627(13) 0.73932(12) 0.60386(7) 0.0148(2) Uani 1 1 d . . . . .
C1 C 0.56207(16) 0.68780(14) 0.69015(8) 0.0162(3) Uani 1 1 d . . . . .
H1 H 0.5459 0.5878 0.6882 0.019 Uiso 1 1 calc R . . . .
C2 C 0.45299(16) 0.75502(14) 0.72800(8) 0.0160(3) Uani 1 1 d . . . . .
H2 H 0.4756 0.8539 0.7351 0.019 Uiso 1 1 calc R . . . .
C3 C 0.28613(16) 0.73559(15) 0.66956(8) 0.0174(3) Uani 1 1 d . . . . .
H3A H 0.2654 0.6387 0.6563 0.021 Uiso 1 1 calc R . . . .
H3B H 0.2155 0.7685 0.6956 0.021 Uiso 1 1 calc R . . . .
C4 C 0.26623(16) 0.81792(15) 0.59149(8) 0.0168(3) Uani 1 1 d . . . . .
H4A H 0.1677 0.7948 0.5503 0.020 Uiso 1 1 calc R . . . .
H4B H 0.2645 0.9153 0.6039 0.020 Uiso 1 1 calc R . . . .
C5 C 0.39031(16) 0.79292(14) 0.55531(8) 0.0147(3) Uani 1 1 d . . . . .
C6 C 0.63948(16) 0.71126(15) 0.56607(8) 0.0156(3) Uani 1 1 d . . . . .
C7 C 0.67651(16) 0.57556(15) 0.55580(8) 0.0181(3) Uani 1 1 d . . . . .
H7 H 0.6311 0.5034 0.5743 0.022 Uiso 1 1 calc R . . . .
C8 C 0.78291(18) 0.54888(17) 0.51723(9) 0.0221(3) Uani 1 1 d . . . . .
H8 H 0.8088 0.4583 0.5101 0.026 Uiso 1 1 calc R . . . .
C9 C 0.85007(17) 0.65634(18) 0.48948(9) 0.0238(3) Uani 1 1 d . . . . .
H9 H 0.9199 0.6380 0.4632 0.029 Uiso 1 1 calc R . . . .
C10 C 0.81292(18) 0.79191(17) 0.50102(9) 0.0229(3) Uani 1 1 d . . . . .
H10 H 0.8587 0.8641 0.4827 0.027 Uiso 1 1 calc R . . . .
C11 C 0.70784(17) 0.82040(15) 0.53972(8) 0.0187(3) Uani 1 1 d . . . . .
H11 H 0.6837 0.9111 0.5479 0.022 Uiso 1 1 calc R . . . .
C12 C 0.72879(16) 0.71720(15) 0.74110(8) 0.0165(3) Uani 1 1 d . . . . .
C13 C 0.82487(18) 0.60822(16) 0.77956(8) 0.0224(3) Uani 1 1 d . . . . .
H13 H 0.7869 0.5186 0.7733 0.027 Uiso 1 1 calc R . . . .
C14 C 0.97801(19) 0.63321(19) 0.82749(9) 0.0286(4) Uani 1 1 d . . . . .
H14 H 1.0415 0.5603 0.8535 0.034 Uiso 1 1 calc R . . . .
C15 C 1.03548(18) 0.7659(2) 0.83629(9) 0.0280(4) Uani 1 1 d . . . . .
H15 H 1.1377 0.7824 0.8678 0.034 Uiso 1 1 calc R . . . .
C16 C 0.94009(18) 0.87475(18) 0.79788(9) 0.0259(3) Uani 1 1 d . . . . .
H16 H 0.9785 0.9642 0.8039 0.031 Uiso 1 1 calc R . . . .
C17 C 0.78798(18) 0.85029(16) 0.75067(8) 0.0204(3) Uani 1 1 d . . . . .
H17 H 0.7248 0.9236 0.7251 0.024 Uiso 1 1 calc R . . . .
C18 C 0.47097(16) 0.69264(15) 0.81128(8) 0.0155(3) 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 C5 1.2388(17) . ?
O2 C18 1.2164(19) . ?
O3 H3 0.8403 . ?
O3 C18 1.3175(17) . ?
N1 C1 1.4960(16) . ?
N1 C5 1.3536(18) . ?
N1 C6 1.4448(17) . ?
C1 H1 0.9800 . ?
C1 C2 1.5309(18) . ?
C1 C12 1.5191(19) . ?
C2 H2 0.9800 . ?
C2 C3 1.5394(19) . ?
C2 C18 1.5156(17) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.5224(18) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.5111(18) . ?
C6 C7 1.387(2) . ?
C6 C11 1.390(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.396(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.391(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(2) . ?
C12 C17 1.390(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.396(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(2) . ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O3 H3 109.5 . . ?
C5 N1 C1 125.53(11) . . ?
C5 N1 C6 117.53(11) . . ?
C6 N1 C1 116.34(11) . . ?
N1 C1 H1 108.6 . . ?
N1 C1 C2 109.48(11) . . ?
N1 C1 C12 110.03(11) . . ?
C2 C1 H1 108.6 . . ?
C12 C1 H1 108.6 . . ?
C12 C1 C2 111.50(11) . . ?
C1 C2 H2 108.9 . . ?
C1 C2 C3 109.49(11) . . ?
C3 C2 H2 108.9 . . ?
C18 C2 C1 111.44(11) . . ?
C18 C2 H2 108.9 . . ?
C18 C2 C3 109.06(11) . . ?
C2 C3 H3A 110.2 . . ?
C2 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C4 C3 C2 107.49(11) . . ?
C4 C3 H3A 110.2 . . ?
C4 C3 H3B 110.2 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.08(12) . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
O1 C5 N1 122.12(12) . . ?
O1 C5 C4 118.68(12) . . ?
N1 C5 C4 119.20(11) . . ?
C7 C6 N1 119.26(12) . . ?
C7 C6 C11 121.20(13) . . ?
C11 C6 N1 119.53(13) . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 119.05(14) . . ?
C8 C7 H7 120.5 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.42(14) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.82(14) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.52(14) . . ?
C11 C10 H10 119.7 . . ?
C6 C11 C10 118.97(14) . . ?
C6 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C13 C12 C1 119.27(13) . . ?
C17 C12 C1 121.66(13) . . ?
C17 C12 C13 119.07(14) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.19(15) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.16(15) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.80(15) . . ?
C16 C15 H15 120.1 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.14(16) . . ?
C17 C16 H16 119.9 . . ?
C12 C17 H17 119.7 . . ?
C16 C17 C12 120.65(14) . . ?
C16 C17 H17 119.7 . . ?
O2 C18 O3 124.16(12) . . ?
O2 C18 C2 123.97(12) . . ?
O3 C18 C2 111.78(12) . . ?

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 51.97(15) . . . . ?
N1 C1 C2 C18 172.71(11) . . . . ?
N1 C1 C12 C13 -122.80(13) . . . . ?
N1 C1 C12 C17 57.48(16) . . . . ?
N1 C6 C7 C8 178.28(12) . . . . ?
N1 C6 C11 C10 -177.92(12) . . . . ?
C1 N1 C5 O1 -173.62(13) . . . . ?
C1 N1 C5 C4 6.6(2) . . . . ?
C1 N1 C6 C7 60.49(17) . . . . ?
C1 N1 C6 C11 -120.32(14) . . . . ?
C1 C2 C3 C4 -66.27(14) . . . . ?
C1 C2 C18 O2 -31.30(19) . . . . ?
C1 C2 C18 O3 151.83(12) . . . . ?
C1 C12 C13 C14 -179.22(12) . . . . ?
C1 C12 C17 C16 179.55(12) . . . . ?
C2 C1 C12 C13 115.52(14) . . . . ?
C2 C1 C12 C17 -64.19(16) . . . . ?
C2 C3 C4 C5 48.96(15) . . . . ?
C3 C2 C18 O2 89.70(16) . . . . ?
C3 C2 C18 O3 -87.17(14) . . . . ?
C3 C4 C5 O1 160.08(13) . . . . ?
C3 C4 C5 N1 -20.10(18) . . . . ?
C5 N1 C1 C2 -22.85(18) . . . . ?
C5 N1 C1 C12 -145.72(13) . . . . ?
C5 N1 C6 C7 -111.13(15) . . . . ?
C5 N1 C6 C11 68.06(17) . . . . ?
C6 N1 C1 C2 166.29(11) . . . . ?
C6 N1 C1 C12 43.41(16) . . . . ?
C6 N1 C5 O1 -2.9(2) . . . . ?
C6 N1 C5 C4 177.33(12) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C7 C6 C11 C10 1.3(2) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C8 C9 C10 C11 -0.5(2) . . . . ?
C9 C10 C11 C6 -0.6(2) . . . . ?
C11 C6 C7 C8 -0.9(2) . . . . ?
C12 C1 C2 C3 173.96(11) . . . . ?
C12 C1 C2 C18 -65.29(15) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C13 C12 C17 C16 -0.2(2) . . . . ?
C13 C14 C15 C16 0.6(2) . . . . ?
C14 C15 C16 C17 -0.2(2) . . . . ?
C15 C16 C17 C12 0.0(2) . . . . ?
C17 C12 C13 C14 0.5(2) . . . . ?
C18 C2 C3 C4 171.55(11) . . . . ?

_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_uny098
_database_code_depnum_ccdc_archive 'CCDC 1470618'
_audit_update_record             
;
2016-03-25 deposited with the CCDC.
2016-08-31 downloaded from the CCDC.
;
_audit_creation_date             2016-03-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H18 Cl N O3'
_chemical_formula_sum            'C19 H18 Cl N O3'
_chemical_formula_weight         343.79
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H17 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'
Cl Cl 0.1484 0.1585 '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                   10.15491(19)
_cell_length_b                   11.7971(2)
_cell_length_c                   14.1333(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.8247(17)
_cell_angle_gamma                90
_cell_volume                     1677.37(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11818
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.1698
_cell_measurement_theta_min      2.6555
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0168
_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       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            28349
_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         27.500
_diffrn_reflns_theta_min         2.661
_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  -35.00   44.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531  -57.0000   90.0000 79

#__ type_ start__ end____ width___ exp.time_
  2 omega   13.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531  -99.0000 -150.0000 56

#__ type_ start__ end____ width___ exp.time_
  3 omega   35.00   61.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531  -99.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   -7.00   69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531  -99.0000   60.0000 76

#__ type_ start__ end____ width___ exp.time_
  5 omega   11.00   94.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531   57.0000  -30.0000 83

#__ type_ start__ end____ width___ exp.time_
  6 omega  -46.00   67.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531  -19.0000  150.0000 113

#__ type_ start__ end____ width___ exp.time_
  7 omega  -91.00  -32.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.5593  178.0000 -150.0000 59

#__ type_ start__ end____ width___ exp.time_
  8 omega    6.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531   57.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
  9 omega   35.00   64.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531  178.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
 10 omega    6.00   60.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531   57.0000   60.0000 54

#__ type_ start__ end____ width___ exp.time_
 11 omega    7.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531   57.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
 12 omega    2.00   95.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531   77.0000 -120.0000 93

#__ type_ start__ end____ width___ exp.time_
 13 omega  -35.00   -4.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       26.6531  131.0000    5.3825 31
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0378095000
_diffrn_orient_matrix_UB_12      0.0501214000
_diffrn_orient_matrix_UB_13      0.0030006000
_diffrn_orient_matrix_UB_21      -0.0459492000
_diffrn_orient_matrix_UB_22      -0.0306202000
_diffrn_orient_matrix_UB_23      0.0236913000
_diffrn_orient_matrix_UB_31      0.0378050000
_diffrn_orient_matrix_UB_32      0.0128714000
_diffrn_orient_matrix_UB_33      0.0446795000
_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                3496
_reflns_number_total             3845
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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         0.378
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3845
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.028
_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)+(0.0391P)²+0.8740P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0840
_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), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Cl1 Cl 1.00250(3) 0.61260(2) 0.89078(2) 0.02114(9) Uani 1 1 d . . . . .
O1 O 0.57918(9) 0.25695(8) 0.64688(6) 0.02153(19) Uani 1 1 d . . . . .
O2 O 0.47449(10) 0.46901(9) 0.87793(11) 0.0449(3) Uani 1 1 d . . . . .
O3 O 0.61395(9) 0.61227(8) 0.86568(8) 0.0269(2) Uani 1 1 d . . . . .
H3 H 0.5435 0.6505 0.8583 0.040 Uiso 1 1 calc GR . . . .
N1 N 0.71376(9) 0.38995(8) 0.72125(7) 0.01286(19) Uani 1 1 d . . . . .
C1 C 0.78762(11) 0.44441(9) 0.80662(8) 0.0126(2) Uani 1 1 d . . . . .
H1 H 0.7931 0.5273 0.7928 0.015 Uiso 1 1 calc R . . . .
C2 C 0.71002(11) 0.43131(10) 0.89228(8) 0.0150(2) Uani 1 1 d . . . . .
H2 H 0.7681 0.4595 0.9504 0.018 Uiso 1 1 calc R . . . .
C3 C 0.67982(12) 0.30677(10) 0.90849(8) 0.0191(2) Uani 1 1 d . . . . .
H3A H 0.6244 0.3005 0.9607 0.023 Uiso 1 1 calc R . . . .
H3B H 0.7641 0.2657 0.9284 0.023 Uiso 1 1 calc R . . . .
C4 C 0.60679(12) 0.25153(10) 0.81793(9) 0.0200(2) Uani 1 1 d . . . . .
H4A H 0.6298 0.1699 0.8195 0.024 Uiso 1 1 calc R . . . .
H4B H 0.5101 0.2571 0.8207 0.024 Uiso 1 1 calc R . . . .
C5 C 0.63346(11) 0.29892(10) 0.72285(8) 0.0154(2) Uani 1 1 d . . . . .
C6 C 0.72827(11) 0.44099(9) 0.63010(8) 0.0130(2) Uani 1 1 d . . . . .
C7 C 0.82677(12) 0.40527(10) 0.57812(9) 0.0178(2) Uani 1 1 d . . . . .
H7 H 0.8859 0.3462 0.6015 0.021 Uiso 1 1 calc R . . . .
C8 C 0.83791(13) 0.45727(11) 0.49088(9) 0.0215(3) Uani 1 1 d . . . . .
H8 H 0.9050 0.4326 0.4548 0.026 Uiso 1 1 calc R . . . .
C9 C 0.75282(13) 0.54457(11) 0.45551(8) 0.0210(3) Uani 1 1 d . . . . .
C10 C 0.65447(12) 0.57913(11) 0.50926(9) 0.0212(3) Uani 1 1 d . . . . .
H10 H 0.5952 0.6383 0.4862 0.025 Uiso 1 1 calc R . . . .
C11 C 0.64226(11) 0.52791(10) 0.59626(8) 0.0178(2) Uani 1 1 d . . . . .
H11 H 0.5752 0.5523 0.6325 0.021 Uiso 1 1 calc R . . . .
C12 C 0.76507(16) 0.60043(14) 0.36049(10) 0.0326(3) Uani 1 1 d . . . . .
H12A H 0.8491 0.5778 0.3392 0.049 Uiso 1 1 calc GR . . . .
H12B H 0.7632 0.6830 0.3678 0.049 Uiso 1 1 calc GR . . . .
H12C H 0.6908 0.5766 0.3130 0.049 Uiso 1 1 calc GR . . . .
C13 C 0.92947(11) 0.39978(10) 0.82807(8) 0.0141(2) Uani 1 1 d . . . . .
C14 C 1.03429(11) 0.47121(10) 0.86379(8) 0.0157(2) Uani 1 1 d . . . . .
C15 C 1.16522(12) 0.43384(12) 0.88106(8) 0.0207(3) Uani 1 1 d . . . . .
H15 H 1.2352 0.4856 0.9009 0.025 Uiso 1 1 calc R . . . .
C16 C 1.19218(12) 0.31988(12) 0.86885(9) 0.0240(3) Uani 1 1 d . . . . .
H16 H 1.2808 0.2927 0.8825 0.029 Uiso 1 1 calc R . . . .
C17 C 1.09010(13) 0.24554(12) 0.83671(9) 0.0233(3) Uani 1 1 d . . . . .
H17 H 1.1083 0.1672 0.8300 0.028 Uiso 1 1 calc R . . . .
C18 C 0.96079(12) 0.28606(11) 0.81433(8) 0.0186(2) Uani 1 1 d . . . . .
H18 H 0.8923 0.2353 0.7892 0.022 Uiso 1 1 calc R . . . .
C19 C 0.58527(11) 0.50491(10) 0.87808(8) 0.0178(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
Cl1 C14 1.7508(12) . ?
O1 C5 1.2413(15) . ?
O2 C19 1.2017(16) . ?
O3 H3 0.8400 . ?
O3 C19 1.3166(15) . ?
N1 C1 1.4781(14) . ?
N1 C5 1.3504(14) . ?
N1 C6 1.4476(14) . ?
C1 H1 1.0000 . ?
C1 C2 1.5395(15) . ?
C1 C13 1.5249(15) . ?
C2 H2 1.0000 . ?
C2 C3 1.5245(16) . ?
C2 C19 1.5264(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5345(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5134(16) . ?
C6 C7 1.3849(16) . ?
C6 C11 1.3891(16) . ?
C7 H7 0.9500 . ?
C7 C8 1.3955(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3927(19) . ?
C9 C10 1.3954(18) . ?
C9 C12 1.5161(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.3907(17) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.3970(16) . ?
C13 C18 1.3983(17) . ?
C14 C15 1.3905(16) . ?
C15 H15 0.9500 . ?
C15 C16 1.387(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.3863(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3928(17) . ?
C18 H18 0.9500 . ?

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
C19 O3 H3 109.5 . . ?
C5 N1 C1 124.92(9) . . ?
C5 N1 C6 118.72(9) . . ?
C6 N1 C1 116.35(9) . . ?
N1 C1 H1 107.5 . . ?
N1 C1 C2 109.94(9) . . ?
N1 C1 C13 111.89(9) . . ?
C2 C1 H1 107.5 . . ?
C13 C1 H1 107.5 . . ?
C13 C1 C2 112.33(9) . . ?
C1 C2 H2 107.7 . . ?
C3 C2 C1 110.48(9) . . ?
C3 C2 H2 107.7 . . ?
C3 C2 C19 112.81(10) . . ?
C19 C2 C1 110.12(9) . . ?
C19 C2 H2 107.7 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C2 C3 C4 111.60(9) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C3 C4 H4A 108.0 . . ?
C3 C4 H4B 108.0 . . ?
H4A C4 H4B 107.2 . . ?
C5 C4 C3 117.33(10) . . ?
C5 C4 H4A 108.0 . . ?
C5 C4 H4B 108.0 . . ?
O1 C5 N1 120.05(10) . . ?
O1 C5 C4 120.57(10) . . ?
N1 C5 C4 119.35(10) . . ?
C7 C6 N1 120.93(10) . . ?
C7 C6 C11 120.51(11) . . ?
C11 C6 N1 118.56(10) . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.10(11) . . ?
C8 C7 H7 120.4 . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.41(11) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 C10 118.41(11) . . ?
C8 C9 C12 121.17(12) . . ?
C10 C9 C12 120.42(12) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.73(12) . . ?
C11 C10 H10 119.6 . . ?
C6 C11 C10 119.84(11) . . ?
C6 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C1 121.08(10) . . ?
C14 C13 C18 116.90(10) . . ?
C18 C13 C1 122.02(10) . . ?
C13 C14 Cl1 119.96(9) . . ?
C15 C14 Cl1 117.65(9) . . ?
C15 C14 C13 122.38(11) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 C14 119.05(12) . . ?
C16 C15 H15 120.5 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.16(11) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.81(12) . . ?
C18 C17 H17 120.1 . . ?
C13 C18 H18 119.2 . . ?
C17 C18 C13 121.53(12) . . ?
C17 C18 H18 119.2 . . ?
O2 C19 O3 124.25(11) . . ?
O2 C19 C2 124.03(12) . . ?
O3 C19 C2 111.72(10) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
