# Electronic Supplementary Material (ESI) for ChemComm.
# 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_Form_I
_database_code_depnum_ccdc_archive 'CCDC 1480079'
_audit_update_record             
;
2016-05-16 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            '3-Methyl-2-Phenylbutyramide, Salicylic acid'
_chemical_formula_moiety         'C11 H15 N O, C7 H6 O3'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         315.36
_chemical_absolute_configuration .

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   16.2716(15)
_cell_length_b                   21.2062(18)
_cell_length_c                   10.0994(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3484.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6603
_cell_measurement_theta_min      2.2336
_cell_measurement_theta_max      24.8608
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.328
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.196
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344

_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            18028
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11

_refine_special_details          
;
;

_reflns_number_total             6129
_reflns_number_gt                4981
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_gt          0.1387
_refine_ls_wR_factor_ref         0.1507
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_number_reflns         6129
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.2890P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.151
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1951 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.38495(18) 0.44349(11) 0.1221(2) 0.0601(7) Uani d . . . 1 . .
H H1A 0.3652 0.481 0.1174 0.072 Uiso calc U . R 1 . .
H H1B 0.3886 0.4249 0.1976 0.072 Uiso calc U . R 1 . .
C C2 0.40945(18) 0.41447(12) 0.0141(3) 0.0472(6) Uani d . . . 1 . .
O O3 0.40492(14) 0.44016(9) -0.09738(19) 0.0557(5) Uani d . . . 1 . .
C C4 0.4458(2) 0.34918(13) 0.0307(3) 0.0532(7) Uani d . . . 1 . .
H H4 0.4271 0.3328 0.1162 0.064 Uiso calc U . R 1 . .
C C5 0.4163(2) 0.30291(14) -0.0773(3) 0.0640(9) Uani d . . . 1 . .
H H5 0.4367 0.318 -0.163 0.077 Uiso calc U . R 1 . .
C C6 0.3235(3) 0.30025(19) -0.0841(6) 0.0959(14) Uani d . . . 1 . .
H H6A 0.3023 0.2842 -0.0021 0.144 Uiso calc U . R 1 . .
H H6B 0.3072 0.273 -0.1554 0.144 Uiso calc U . R 1 . .
H H6C 0.3022 0.3419 -0.0992 0.144 Uiso calc U . R 1 . .
C C7 0.4507(3) 0.23707(16) -0.0544(5) 0.0873(13) Uani d . . . 1 . .
H H7A 0.4343 0.2224 0.0316 0.131 Uiso calc U . R 1 . .
H H7B 0.5096 0.2383 -0.0593 0.131 Uiso calc U . R 1 . .
H H7C 0.4299 0.2089 -0.1209 0.131 Uiso calc U . R 1 . .
C C8 0.5390(2) 0.35488(13) 0.0372(3) 0.0538(8) Uani d . . . 1 . .
C C9 0.5815(3) 0.32644(19) 0.1397(4) 0.0777(11) Uani d . . . 1 . .
H H9 0.5528 0.3049 0.2052 0.093 Uiso calc U . R 1 . .
C C10 0.6666(3) 0.3298(2) 0.1456(5) 0.0986(15) Uani d . . . 1 . .
H H10 0.6947 0.31 0.2141 0.118 Uiso calc U . R 1 . .
C C11 0.7095(3) 0.3625(2) 0.0501(5) 0.0905(13) Uani d . . . 1 . .
H H11 0.7665 0.3651 0.0546 0.109 Uiso calc U . R 1 . .
C C12 0.6681(3) 0.39109(18) -0.0513(4) 0.0776(11) Uani d . . . 1 . .
H H12 0.697 0.4133 -0.1156 0.093 Uiso calc U . R 1 . .
C C13 0.5828(2) 0.38695(14) -0.0584(4) 0.0617(8) Uani d . . . 1 . .
H H13 0.5551 0.406 -0.1283 0.074 Uiso calc U . R 1 . .
O O21 0.3590(2) 0.57794(11) 1.0658(2) 0.0860(9) Uani d . . . 1 . .
C C22 0.3622(2) 0.59730(14) 0.9525(3) 0.0600(8) Uani d . . . 1 . .
O O23 0.3724(2) 0.55897(10) 0.8514(2) 0.0759(7) Uani d . . . 1 . .
H H23 0.3739 0.5224 0.878 0.114 Uiso calc U . R 1 . .
C C24 0.3539(2) 0.66433(15) 0.9167(3) 0.0652(9) Uani d . . . 1 . .
C C25 0.3472(4) 0.68367(19) 0.7860(4) 0.1018(17) Uani d . . . 1 . .
H H25 0.346 0.6537 0.7188 0.122 Uiso calc U . R 1 . .
C C26 0.3424(4) 0.7468(2) 0.7545(5) 0.116(2) Uani d . . . 1 . .
H H26 0.3383 0.7594 0.6666 0.139 Uiso calc U . R 1 . .
C C27 0.3436(4) 0.79037(19) 0.8523(5) 0.1100(18) Uani d . . . 1 . .
H H27 0.342 0.833 0.8311 0.132 Uiso calc U . R 1 . .
C C28 0.3472(5) 0.77272(19) 0.9786(5) 0.138(3) Uani d . . . 1 . .
H H28 0.3471 0.8034 1.0444 0.165 Uiso calc U . R 1 . .
C C29 0.3510(4) 0.70914(19) 1.0149(4) 0.1102(19) Uani d . . . 1 . .
O O30 0.3539(6) 0.69386(17) 1.1426(3) 0.241(4) Uani d . . . 1 . .
H H30 0.3293 0.6606 1.1544 0.361 Uiso calc U . R 1 . .
N N31 0.3752(2) 0.39059(12) 0.6225(3) 0.0671(8) Uani d . . . 1 . .
H H31A 0.3577 0.3524 0.6191 0.081 Uiso calc U . R 1 . .
H H31B 0.38 0.4093 0.6977 0.081 Uiso calc U . R 1 . .
C C32 0.39470(19) 0.42034(13) 0.5133(3) 0.0513(7) Uani d . . . 1 . .
O O33 0.38870(17) 0.39493(10) 0.4021(2) 0.0645(6) Uani d . . . 1 . .
C C34 0.42834(19) 0.48652(13) 0.5286(3) 0.0503(7) Uani d . . . 1 . .
H H34 0.4073 0.503 0.6126 0.06 Uiso calc U . R 1 . .
C C35 0.39985(19) 0.53210(13) 0.4189(3) 0.0521(7) Uani d . . . 1 . .
H H35 0.425 0.5182 0.3356 0.063 Uiso calc U . R 1 . .
C C36 0.3071(2) 0.53082(19) 0.4002(5) 0.0829(11) Uani d . . . 1 . .
H H36A 0.2807 0.541 0.4825 0.124 Uiso calc U . R 1 . .
H H36B 0.2904 0.4895 0.3722 0.124 Uiso calc U . R 1 . .
H H36C 0.2916 0.5612 0.3343 0.124 Uiso calc U . R 1 . .
C C37 0.4295(3) 0.59927(15) 0.4460(4) 0.0741(10) Uani d . . . 1 . .
H H37A 0.4154 0.6259 0.3725 0.111 Uiso calc U . R 1 . .
H H37B 0.4881 0.5992 0.4576 0.111 Uiso calc U . R 1 . .
H H37C 0.4037 0.615 0.5248 0.111 Uiso calc U . R 1 . .
C C38 0.52081(19) 0.48264(14) 0.5412(3) 0.0554(8) Uani d . . . 1 . .
C C39 0.5662(2) 0.44862(16) 0.4502(5) 0.0749(11) Uani d . . . 1 . .
H H39 0.5401 0.4273 0.3818 0.09 Uiso calc U . R 1 . .
C C40 0.6515(3) 0.4466(2) 0.4619(7) 0.113(2) Uani d . . . 1 . .
H H40 0.6825 0.4238 0.4011 0.136 Uiso calc U . R 1 . .
C C41 0.6894(3) 0.4780(3) 0.5627(9) 0.136(3) Uani d . . . 1 . .
H H41 0.7463 0.4764 0.5707 0.163 Uiso calc U . R 1 . .
C C42 0.6441(4) 0.5121(4) 0.6523(7) 0.133(3) Uani d . . . 1 . .
H H42 0.6706 0.5338 0.72 0.159 Uiso calc U . R 1 . .
C C43 0.5597(3) 0.5145(2) 0.6431(4) 0.0874(13) Uani d . . . 1 . .
H H43 0.5292 0.5372 0.7047 0.105 Uiso calc U . R 1 . .
O O51 0.3872(3) 0.25429(12) 0.5651(3) 0.1145(13) Uani d . . . 1 . .
C C52 0.3845(3) 0.23540(16) 0.4514(4) 0.0735(10) Uani d . . . 1 . .
O O53 0.3767(2) 0.27394(11) 0.3510(2) 0.0908(9) Uani d . . . 1 . .
H H53 0.3857 0.3102 0.3756 0.136 Uiso calc U . R 1 . .
C C54 0.3907(2) 0.16843(15) 0.4164(4) 0.0657(9) Uani d . . . 1 . .
C C55 0.3760(3) 0.14760(17) 0.2876(4) 0.0810(11) Uani d . . . 1 . .
H H55 0.3606 0.1763 0.2226 0.097 Uiso calc U . R 1 . .
C C56 0.3843(3) 0.08439(17) 0.2558(4) 0.0895(13) Uani d . . . 1 . .
H H56 0.3747 0.0706 0.1698 0.107 Uiso calc U . R 1 . .
C C57 0.4068(2) 0.04217(17) 0.3530(5) 0.0789(11) Uani d . . . 1 . .
H H57 0.4133 -0.0002 0.3314 0.095 Uiso calc U . R 1 . .
C C58 0.4193(3) 0.06093(18) 0.4779(5) 0.0936(14) Uani d . . . 1 . .
H H58 0.4342 0.0317 0.5421 0.112 Uiso calc U . R 1 . .
C C59 0.4102(3) 0.12418(18) 0.5117(4) 0.0879(13) Uani d . . . 1 . .
O O60 0.4239(4) 0.14042(15) 0.6383(4) 0.175(3) Uani d . . . 1 . .
H H60 0.4267 0.1789 0.6442 0.263 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.315(4) ?
N1 H1A . 0.86 ?
N1 H1B . 0.86 ?
C2 O3 . 1.253(3) ?
C2 C4 . 1.515(4) ?
C4 C8 . 1.522(5) ?
C4 C5 . 1.544(4) ?
C4 H4 . 0.98 ?
C5 C6 . 1.511(6) ?
C5 C7 . 1.522(5) ?
C5 H5 . 0.98 ?
C6 H6A . 0.96 ?
C6 H6B . 0.96 ?
C6 H6C . 0.96 ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
C8 C13 . 1.379(5) ?
C8 C9 . 1.383(5) ?
C9 C10 . 1.389(7) ?
C9 H9 . 0.93 ?
C10 C11 . 1.377(7) ?
C10 H10 . 0.93 ?
C11 C12 . 1.368(6) ?
C11 H11 . 0.93 ?
C12 C13 . 1.393(5) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
O21 C22 . 1.217(4) ?
C22 O23 . 1.315(4) ?
C22 C24 . 1.473(4) ?
O23 H23 . 0.82 ?
C24 C29 . 1.374(5) ?
C24 C25 . 1.387(6) ?
C25 C26 . 1.379(6) ?
C25 H25 . 0.93 ?
C26 C27 . 1.352(7) ?
C26 H26 . 0.93 ?
C27 C28 . 1.331(7) ?
C27 H27 . 0.93 ?
C28 C29 . 1.399(6) ?
C28 H28 . 0.93 ?
C29 O30 . 1.330(5) ?
O30 H30 . 0.82 ?
N31 C32 . 1.310(4) ?
N31 H31A . 0.86 ?
N31 H31B . 0.86 ?
C32 O33 . 1.249(3) ?
C32 C34 . 1.514(4) ?
C34 C38 . 1.512(4) ?
C34 C35 . 1.542(4) ?
C34 H34 . 0.98 ?
C35 C36 . 1.521(5) ?
C35 C37 . 1.529(4) ?
C35 H35 . 0.98 ?
C36 H36A . 0.96 ?
C36 H36B . 0.96 ?
C36 H36C . 0.96 ?
C37 H37A . 0.96 ?
C37 H37B . 0.96 ?
C37 H37C . 0.96 ?
C38 C39 . 1.383(5) ?
C38 C43 . 1.384(5) ?
C39 C40 . 1.393(6) ?
C39 H39 . 0.93 ?
C40 C41 . 1.365(10) ?
C40 H40 . 0.93 ?
C41 C42 . 1.374(10) ?
C41 H41 . 0.93 ?
C42 C43 . 1.376(8) ?
C42 H42 . 0.93 ?
C43 H43 . 0.93 ?
O51 C52 . 1.216(4) ?
C52 O53 . 1.309(4) ?
C52 C54 . 1.467(5) ?
O53 H53 . 0.82 ?
C54 C59 . 1.381(5) ?
C54 C55 . 1.394(5) ?
C55 C56 . 1.385(5) ?
C55 H55 . 0.93 ?
C56 C57 . 1.378(6) ?
C56 H56 . 0.93 ?
C57 C58 . 1.338(6) ?
C57 H57 . 0.93 ?
C58 C59 . 1.392(6) ?
C58 H58 . 0.93 ?
C59 O60 . 1.343(5) ?
O60 H60 . 0.82 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 H1A . . 120.0 ?
C2 N1 H1B . . 120.0 ?
H1A N1 H1B . . 120.0 ?
O3 C2 N1 . . 121.6(2) ?
O3 C2 C4 . . 121.3(2) ?
N1 C2 C4 . . 117.1(2) ?
C2 C4 C8 . . 108.7(2) ?
C2 C4 C5 . . 112.4(2) ?
C8 C4 C5 . . 113.0(3) ?
C2 C4 H4 . . 107.5 ?
C8 C4 H4 . . 107.5 ?
C5 C4 H4 . . 107.5 ?
C6 C5 C7 . . 109.9(3) ?
C6 C5 C4 . . 111.5(3) ?
C7 C5 C4 . . 111.1(3) ?
C6 C5 H5 . . 108.1 ?
C7 C5 H5 . . 108.1 ?
C4 C5 H5 . . 108.1 ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C5 C7 H7A . . 109.5 ?
C5 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C5 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C13 C8 C9 . . 118.7(3) ?
C13 C8 C4 . . 121.6(3) ?
C9 C8 C4 . . 119.7(3) ?
C8 C9 C10 . . 120.5(4) ?
C8 C9 H9 . . 119.7 ?
C10 C9 H9 . . 119.7 ?
C11 C10 C9 . . 120.1(4) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C12 C11 C10 . . 119.9(4) ?
C12 C11 H11 . . 120.1 ?
C10 C11 H11 . . 120.1 ?
C11 C12 C13 . . 120.1(4) ?
C11 C12 H12 . . 120.0 ?
C13 C12 H12 . . 120.0 ?
C8 C13 C12 . . 120.7(3) ?
C8 C13 H13 . . 119.7 ?
C12 C13 H13 . . 119.7 ?
O21 C22 O23 . . 121.8(3) ?
O21 C22 C24 . . 123.5(3) ?
O23 C22 C24 . . 114.7(3) ?
C22 O23 H23 . . 109.5 ?
C29 C24 C25 . . 118.7(3) ?
C29 C24 C22 . . 119.6(3) ?
C25 C24 C22 . . 121.7(3) ?
C26 C25 C24 . . 120.7(4) ?
C26 C25 H25 . . 119.6 ?
C24 C25 H25 . . 119.6 ?
C27 C26 C25 . . 119.6(4) ?
C27 C26 H26 . . 120.2 ?
C25 C26 H26 . . 120.2 ?
C28 C27 C26 . . 120.6(4) ?
C28 C27 H27 . . 119.7 ?
C26 C27 H27 . . 119.7 ?
C27 C28 C29 . . 121.6(4) ?
C27 C28 H28 . . 119.2 ?
C29 C28 H28 . . 119.2 ?
O30 C29 C24 . . 122.0(4) ?
O30 C29 C28 . . 119.4(4) ?
C24 C29 C28 . . 118.6(4) ?
C29 O30 H30 . . 109.5 ?
C32 N31 H31A . . 120.0 ?
C32 N31 H31B . . 120.0 ?
H31A N31 H31B . . 120.0 ?
O33 C32 N31 . . 122.0(3) ?
O33 C32 C34 . . 121.3(3) ?
N31 C32 C34 . . 116.6(2) ?
C38 C34 C32 . . 108.5(2) ?
C38 C34 C35 . . 113.2(2) ?
C32 C34 C35 . . 113.5(2) ?
C38 C34 H34 . . 107.1 ?
C32 C34 H34 . . 107.1 ?
C35 C34 H34 . . 107.1 ?
C36 C35 C37 . . 110.6(3) ?
C36 C35 C34 . . 112.1(3) ?
C37 C35 C34 . . 111.1(3) ?
C36 C35 H35 . . 107.6 ?
C37 C35 H35 . . 107.6 ?
C34 C35 H35 . . 107.6 ?
C35 C36 H36A . . 109.5 ?
C35 C36 H36B . . 109.5 ?
H36A C36 H36B . . 109.5 ?
C35 C36 H36C . . 109.5 ?
H36A C36 H36C . . 109.5 ?
H36B C36 H36C . . 109.5 ?
C35 C37 H37A . . 109.5 ?
C35 C37 H37B . . 109.5 ?
H37A C37 H37B . . 109.5 ?
C35 C37 H37C . . 109.5 ?
H37A C37 H37C . . 109.5 ?
H37B C37 H37C . . 109.5 ?
C39 C38 C43 . . 120.3(4) ?
C39 C38 C34 . . 120.3(3) ?
C43 C38 C34 . . 119.4(3) ?
C38 C39 C40 . . 119.5(5) ?
C38 C39 H39 . . 120.2 ?
C40 C39 H39 . . 120.2 ?
C41 C40 C39 . . 119.9(6) ?
C41 C40 H40 . . 120.1 ?
C39 C40 H40 . . 120.1 ?
C40 C41 C42 . . 120.4(5) ?
C40 C41 H41 . . 119.8 ?
C42 C41 H41 . . 119.8 ?
C41 C42 C43 . . 120.7(6) ?
C41 C42 H42 . . 119.7 ?
C43 C42 H42 . . 119.7 ?
C42 C43 C38 . . 119.2(6) ?
C42 C43 H43 . . 120.4 ?
C38 C43 H43 . . 120.4 ?
O51 C52 O53 . . 121.9(3) ?
O51 C52 C54 . . 123.0(3) ?
O53 C52 C54 . . 115.1(3) ?
C52 O53 H53 . . 109.5 ?
C59 C54 C55 . . 118.3(3) ?
C59 C54 C52 . . 120.3(3) ?
C55 C54 C52 . . 121.3(3) ?
C56 C55 C54 . . 120.4(4) ?
C56 C55 H55 . . 119.8 ?
C54 C55 H55 . . 119.8 ?
C57 C56 C55 . . 119.3(4) ?
C57 C56 H56 . . 120.3 ?
C55 C56 H56 . . 120.3 ?
C58 C57 C56 . . 121.2(4) ?
C58 C57 H57 . . 119.4 ?
C56 C57 H57 . . 119.4 ?
C57 C58 C59 . . 120.1(4) ?
C57 C58 H58 . . 119.9 ?
C59 C58 H58 . . 119.9 ?
O60 C59 C54 . . 121.8(4) ?
O60 C59 C58 . . 117.6(4) ?
C54 C59 C58 . . 120.5(4) ?
C59 O60 H60 . . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O3 C2 C4 C8 . . . . 82.6(3) ?
N1 C2 C4 C8 . . . . -95.6(3) ?
O3 C2 C4 C5 . . . . -43.3(4) ?
N1 C2 C4 C5 . . . . 138.4(3) ?
C2 C4 C5 C6 . . . . -54.4(4) ?
C8 C4 C5 C6 . . . . -178.0(3) ?
C2 C4 C5 C7 . . . . -177.4(3) ?
C8 C4 C5 C7 . . . . 59.1(4) ?
C2 C4 C8 C13 . . . . -52.2(4) ?
C5 C4 C8 C13 . . . . 73.3(4) ?
C2 C4 C8 C9 . . . . 128.9(3) ?
C5 C4 C8 C9 . . . . -105.5(3) ?
C13 C8 C9 C10 . . . . -0.4(5) ?
C4 C8 C9 C10 . . . . 178.4(4) ?
C8 C9 C10 C11 . . . . 1.0(7) ?
C9 C10 C11 C12 . . . . -0.6(7) ?
C10 C11 C12 C13 . . . . -0.3(6) ?
C9 C8 C13 C12 . . . . -0.5(5) ?
C4 C8 C13 C12 . . . . -179.4(3) ?
C11 C12 C13 C8 . . . . 0.9(6) ?
O21 C22 C24 C29 . . . . 7.1(7) ?
O23 C22 C24 C29 . . . . -173.7(5) ?
O21 C22 C24 C25 . . . . -171.5(5) ?
O23 C22 C24 C25 . . . . 7.7(6) ?
C29 C24 C25 C26 . . . . 3.6(9) ?
C22 C24 C25 C26 . . . . -177.7(5) ?
C24 C25 C26 C27 . . . . -0.5(10) ?
C25 C26 C27 C28 . . . . -1.9(11) ?
C26 C27 C28 C29 . . . . 1.0(12) ?
C25 C24 C29 O30 . . . . 177.4(7) ?
C22 C24 C29 O30 . . . . -1.2(10) ?
C25 C24 C29 C28 . . . . -4.4(9) ?
C22 C24 C29 C28 . . . . 176.9(6) ?
C27 C28 C29 O30 . . . . -179.6(8) ?
C27 C28 C29 C24 . . . . 2.2(12) ?
O33 C32 C34 C38 . . . . -87.5(4) ?
N31 C32 C34 C38 . . . . 90.1(3) ?
O33 C32 C34 C35 . . . . 39.3(4) ?
N31 C32 C34 C35 . . . . -143.1(3) ?
C38 C34 C35 C36 . . . . 175.0(3) ?
C32 C34 C35 C36 . . . . 50.7(4) ?
C38 C34 C35 C37 . . . . -60.6(3) ?
C32 C34 C35 C37 . . . . 175.1(3) ?
C32 C34 C38 C39 . . . . 50.7(4) ?
C35 C34 C38 C39 . . . . -76.3(4) ?
C32 C34 C38 C43 . . . . -130.6(3) ?
C35 C34 C38 C43 . . . . 102.4(3) ?
C43 C38 C39 C40 . . . . 0.1(5) ?
C34 C38 C39 C40 . . . . 178.7(3) ?
C38 C39 C40 C41 . . . . 0.0(7) ?
C39 C40 C41 C42 . . . . -0.4(8) ?
C40 C41 C42 C43 . . . . 0.8(9) ?
C41 C42 C43 C38 . . . . -0.7(8) ?
C39 C38 C43 C42 . . . . 0.3(6) ?
C34 C38 C43 C42 . . . . -178.4(4) ?
O51 C52 C54 C59 . . . . -8.1(7) ?
O53 C52 C54 C59 . . . . 171.1(4) ?
O51 C52 C54 C55 . . . . 171.0(5) ?
O53 C52 C54 C55 . . . . -9.7(6) ?
C59 C54 C55 C56 . . . . -2.6(7) ?
C52 C54 C55 C56 . . . . 178.3(4) ?
C54 C55 C56 C57 . . . . 0.3(7) ?
C55 C56 C57 C58 . . . . 1.2(7) ?
C56 C57 C58 C59 . . . . -0.3(7) ?
C55 C54 C59 O60 . . . . -178.9(5) ?
C52 C54 C59 O60 . . . . 0.2(8) ?
C55 C54 C59 C58 . . . . 3.4(7) ?
C52 C54 C59 C58 . . . . -177.4(4) ?
C57 C58 C59 O60 . . . . -179.8(6) ?
C57 C58 C59 C54 . . . . -2.0(8) ?



####################################################################### 
# 
# 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_Form_II
_database_code_depnum_ccdc_archive 'CCDC 1480080'
_audit_update_record             
;
2016-05-16 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_weight         315.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.882(4)
_cell_length_b                   20.953(8)
_cell_length_c                   16.215(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.913(11)
_cell_angle_gamma                90
_cell_volume                     3350(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3281
_cell_measurement_theta_min      3
_cell_measurement_theta_max      20

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4205
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21286
_diffrn_reflns_av_unetI/netI     0.1597
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.675
_diffrn_reflns_theta_max         27.699
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measured_fraction_theta_full 0.871
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_point_group_measured_fraction_max 0.644
_reflns_number_total             10125
_reflns_number_gt                6088
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.488
_reflns_Friedel_fraction_max     0.435
_reflns_Friedel_fraction_full    0.498

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1409P)²+8.3710P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1578 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.7(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         10125
_refine_ls_number_parameters     845
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.1735
_refine_ls_R_factor_gt           0.1089
_refine_ls_wR_factor_ref         0.3014
_refine_ls_wR_factor_gt          0.2653
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.1178(9) 0.5650(4) 0.9006(5) 0.036(2) Uani 1 1 d . . . . .
H1 H 0.1142 0.5287 0.8785 0.043 Uiso 1 1 calc R U . . .
O2 O 0.3019(8) 0.5790(3) 0.8283(5) 0.0286(18) Uani 1 1 d . . . . .
O3 O 0.3580(9) 0.6935(4) 0.7793(5) 0.039(2) Uani 1 1 d . . . . .
H3 H 0.3877 0.6578 0.7957 0.047 Uiso 1 1 calc R U . . .
O4 O 0.1524(8) 0.4422(3) 0.8952(5) 0.0241(17) Uani 1 1 d . . . . .
O5 O 0.6190(9) 0.2756(4) 0.8979(5) 0.036(2) Uani 1 1 d . . . . .
H5 H 0.6502 0.3127 0.9042 0.043 Uiso 1 1 calc R U . . .
O6 O 0.8193(8) 0.2575(4) 0.8465(5) 0.0278(18) Uani 1 1 d . . . . .
O7 O 0.9048(9) 0.1409(4) 0.8389(6) 0.040(2) Uani 1 1 d . . . . .
H7 H 0.9057 0.1807 0.8326 0.048 Uiso 1 1 calc R U . . .
O8 O 0.6484(7) 0.3978(3) 0.8742(4) 0.0210(17) Uani 1 1 d . . . . .
O9 O 0.5924(8) 0.4356(3) 0.6365(5) 0.0276(18) Uani 1 1 d . . . . .
H9 H 0.6170 0.4730 0.6259 0.033 Uiso 1 1 calc R U . . .
O10 O 0.8124(8) 0.4136(4) 0.6255(5) 0.0278(18) Uani 1 1 d . . . . .
O11 O 0.8789(9) 0.2937(4) 0.6081(6) 0.043(2) Uani 1 1 d . . . . .
H11 H 0.8938 0.3331 0.6114 0.052 Uiso 1 1 calc R U . . .
O12 O 0.6402(7) 0.5550(3) 0.5887(4) 0.0217(17) Uani 1 1 d . . . . .
O13 O 0.0881(8) 0.7211(3) 0.6244(5) 0.0282(18) Uani 1 1 d . . . . .
H13 H 0.1085 0.6838 0.6110 0.034 Uiso 1 1 calc R U . . .
O14 O 0.2920(9) 0.7444(3) 0.5814(5) 0.0302(19) Uani 1 1 d . . . . .
O15 O 0.3512(9) 0.8608(3) 0.5445(5) 0.033(2) Uani 1 1 d . . . . .
H15 H 0.3573 0.8209 0.5408 0.039 Uiso 1 1 calc R U . . .
O16 O 0.1452(7) 0.6023(3) 0.5943(5) 0.0227(17) Uani 1 1 d . . . . .
N1 N 0.3731(9) 0.4457(4) 0.8689(5) 0.024(2) Uani 1 1 d . . . . .
H1A H 0.3638 0.4846 0.8490 0.029 Uiso 1 1 calc R U . . .
H1B H 0.4527 0.4267 0.8703 0.029 Uiso 1 1 calc R U . . .
N2 N 0.8726(9) 0.3937(4) 0.8573(5) 0.022(2) Uani 1 1 d . . . . .
H2A H 0.8658 0.3556 0.8346 0.026 Uiso 1 1 calc R U . . .
H2B H 0.9521 0.4126 0.8638 0.026 Uiso 1 1 calc R U . . .
N3 N 0.8648(9) 0.5504(4) 0.6061(5) 0.022(2) Uani 1 1 d . . . . .
H3A H 0.8622 0.5122 0.6285 0.027 Uiso 1 1 calc R U . . .
H3B H 0.9433 0.5691 0.6003 0.027 Uiso 1 1 calc R U . . .
N4 N 0.3708(9) 0.6104(4) 0.6102(5) 0.024(2) Uani 1 1 d . . . . .
H4A H 0.3671 0.6512 0.6228 0.028 Uiso 1 1 calc R U . . .
H4B H 0.4499 0.5912 0.6088 0.028 Uiso 1 1 calc R U . . .
C1 C 0.2081(12) 0.6006(5) 0.8648(6) 0.023(3) Uani 1 1 d . . . . .
C2 C 0.1830(11) 0.6705(5) 0.8726(6) 0.021(2) Uani 1 1 d . . . . .
C3 C 0.2604(12) 0.7129(5) 0.8275(7) 0.026(3) Uani 1 1 d . . . . .
C4 C 0.2349(13) 0.7775(5) 0.8333(7) 0.034(3) Uani 1 1 d . . . . .
H4 H 0.2827 0.8067 0.8012 0.041 Uiso 1 1 calc R U . . .
C5 C 0.1413(14) 0.7999(6) 0.8849(7) 0.038(3) Uani 1 1 d . . . . .
H2 H 0.1276 0.8446 0.8900 0.045 Uiso 1 1 calc R U . . .
C6 C 0.0672(15) 0.7584(6) 0.9295(8) 0.042(3) Uani 1 1 d . . . . .
H6 H 0.0009 0.7741 0.9641 0.050 Uiso 1 1 calc R U . . .
C7 C 0.0895(13) 0.6939(6) 0.9236(6) 0.031(3) Uani 1 1 d . . . . .
H8 H 0.0396 0.6651 0.9552 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2662(11) 0.4153(5) 0.8971(6) 0.021(2) Uani 1 1 d . . . . .
C9 C 0.2849(11) 0.3484(5) 0.9293(6) 0.021(2) Uani 1 1 d . . . . .
H10 H 0.3750 0.3328 0.9131 0.025 Uiso 1 1 calc R U . . .
C10 C 0.2890(11) 0.3497(4) 1.0256(6) 0.018(2) Uani 1 1 d . . . . .
C11 C 0.1929(13) 0.3789(5) 1.0654(6) 0.029(3) Uani 1 1 d . . . . .
H17 H 0.1240 0.4018 1.0343 0.035 Uiso 1 1 calc R U . . .
C12 C 0.1901(13) 0.3770(5) 1.1540(7) 0.032(3) Uani 1 1 d . . . . .
H12 H 0.1204 0.3975 1.1816 0.038 Uiso 1 1 calc R U . . .
C13 C 0.2957(14) 0.3432(6) 1.1981(7) 0.037(3) Uani 1 1 d . . . . .
H18 H 0.2997 0.3413 1.2567 0.044 Uiso 1 1 calc R U . . .
C14 C 0.3914(13) 0.3134(5) 1.1556(7) 0.033(3) Uani 1 1 d . . . . .
H14 H 0.4605 0.2895 1.1852 0.039 Uiso 1 1 calc R U . . .
C15 C 0.3908(12) 0.3170(5) 1.0699(7) 0.026(3) Uani 1 1 d . . . . .
H19 H 0.4606 0.2969 1.0419 0.031 Uiso 1 1 calc R U . . .
C16 C 0.1766(13) 0.3027(5) 0.8925(6) 0.024(3) Uani 1 1 d . . . . .
H16 H 0.0874 0.3161 0.9126 0.029 Uiso 1 1 calc R U . . .
C17 C 0.2030(14) 0.2340(5) 0.9196(7) 0.034(3) Uani 1 1 d . . . . .
H17A H 0.2896 0.2197 0.9001 0.052 Uiso 1 1 calc R U . . .
H17B H 0.1297 0.2067 0.8961 0.052 Uiso 1 1 calc R U . . .
H17C H 0.2065 0.2315 0.9801 0.052 Uiso 1 1 calc R U . . .
C18 C 0.1654(13) 0.3065(5) 0.7969(7) 0.032(3) Uani 1 1 d . . . . .
H18A H 0.1679 0.3512 0.7795 0.049 Uiso 1 1 calc R U . . .
H18B H 0.0798 0.2871 0.7755 0.049 Uiso 1 1 calc R U . . .
H18C H 0.2414 0.2834 0.7750 0.049 Uiso 1 1 calc R U . . .
C19 C 0.7153(12) 0.2372(5) 0.8766(6) 0.023(2) Uani 1 1 d . . . . .
C20 C 0.6930(12) 0.1703(5) 0.8931(6) 0.021(2) Uani 1 1 d . . . . .
C21 C 0.7906(11) 0.1238(5) 0.8726(6) 0.020(2) Uani 1 1 d . U . . .
C22 C 0.7645(11) 0.0596(5) 0.8871(6) 0.026(3) Uani 1 1 d . U . . .
H22 H 0.8284 0.0282 0.8730 0.031 Uiso 1 1 calc R U . . .
C23 C 0.6488(14) 0.0413(6) 0.9209(7) 0.034(3) Uani 1 1 d . . . . .
H23 H 0.6338 -0.0027 0.9309 0.041 Uiso 1 1 calc R U . . .
C24 C 0.5542(15) 0.0845(6) 0.9410(10) 0.051(4) Uani 1 1 d . . . . .
H24 H 0.4739 0.0710 0.9649 0.062 Uiso 1 1 calc R U . . .
C25 C 0.5765(14) 0.1490(6) 0.9259(7) 0.038(3) Uani 1 1 d . . . . .
H25 H 0.5093 0.1791 0.9388 0.046 Uiso 1 1 calc R U . . .
C26 C 0.7616(11) 0.4229(5) 0.8823(6) 0.020(2) Uani 1 1 d . . . . .
C27 C 0.7825(11) 0.4883(4) 0.9237(6) 0.017(2) Uani 1 1 d . . . . .
H27 H 0.8755 0.5037 0.9132 0.021 Uiso 1 1 calc R U . . .
C28 C 0.7759(12) 0.4788(5) 1.0169(6) 0.023(2) Uani 1 1 d . . . . .
C29 C 0.8806(12) 0.4989(5) 1.0707(7) 0.028(3) Uani 1 1 d . . . . .
H29 H 0.9579 0.5182 1.0495 0.034 Uiso 1 1 calc R U . . .
C30 C 0.8755(14) 0.4917(5) 1.1547(7) 0.034(3) Uani 1 1 d . . . . .
H30 H 0.9489 0.5058 1.1910 0.041 Uiso 1 1 calc R U . . .
C31 C 0.7600(13) 0.4632(5) 1.1866(7) 0.031(3) Uani 1 1 d . . . . .
H31 H 0.7548 0.4585 1.2446 0.037 Uiso 1 1 calc R U . . .
C32 C 0.6591(13) 0.4431(5) 1.1347(7) 0.027(3) Uani 1 1 d . . . . .
H32 H 0.5824 0.4234 1.1562 0.033 Uiso 1 1 calc R U . . .
C33 C 0.6630(14) 0.4502(5) 1.0502(7) 0.033(3) Uani 1 1 d . . . . .
H33 H 0.5892 0.4357 1.0144 0.039 Uiso 1 1 calc R U . . .
C34 C 0.6794(14) 0.5378(5) 0.8881(7) 0.030(3) Uani 1 1 d . . . . .
H34 H 0.5885 0.5266 0.9075 0.036 Uiso 1 1 calc R U . . .
C35 C 0.7180(13) 0.6045(5) 0.9213(7) 0.031(3) Uani 1 1 d . . . . .
H35A H 0.7281 0.6033 0.9819 0.047 Uiso 1 1 calc R U . . .
H35B H 0.6467 0.6350 0.9035 0.047 Uiso 1 1 calc R U . . .
H35C H 0.8039 0.6178 0.8998 0.047 Uiso 1 1 calc R U . . .
C36 C 0.6687(18) 0.5374(6) 0.7947(7) 0.053(4) Uani 1 1 d . . . . .
H36A H 0.7565 0.5490 0.7743 0.080 Uiso 1 1 calc R U . . .
H36B H 0.5998 0.5683 0.7744 0.080 Uiso 1 1 calc R U . . .
H36C H 0.6428 0.4946 0.7748 0.080 Uiso 1 1 calc R U . . .
C37 C 0.6994(13) 0.3960(5) 0.6353(6) 0.025(3) Uani 1 1 d . . . . .
C38 C 0.6629(12) 0.3283(5) 0.6511(6) 0.021(2) Uani 1 1 d . . . . .
C39 C 0.7542(11) 0.2811(5) 0.6330(7) 0.023(2) Uani 1 1 d . . . . .
C40 C 0.7224(12) 0.2170(5) 0.6404(7) 0.026(3) Uani 1 1 d . . . . .
H40 H 0.7837 0.1849 0.6253 0.032 Uiso 1 1 calc R U . . .
C41 C 0.5980(12) 0.2009(5) 0.6707(6) 0.029(3) Uani 1 1 d . . . . .
H41 H 0.5768 0.1572 0.6786 0.035 Uiso 1 1 calc R U . . .
C42 C 0.5051(12) 0.2471(5) 0.6894(7) 0.031(3) Uani 1 1 d . . . . .
H42 H 0.4208 0.2354 0.7099 0.037 Uiso 1 1 calc R U . . .
C43 C 0.5376(12) 0.3115(5) 0.6777(7) 0.028(3) Uani 1 1 d . . . . .
H43 H 0.4733 0.3438 0.6881 0.033 Uiso 1 1 calc R U . . .
C44 C 0.7511(11) 0.5796(5) 0.5815(6) 0.018(2) Uani 1 1 d . . . . .
C45 C 0.7701(12) 0.6456(5) 0.5444(6) 0.023(2) Uani 1 1 d . . . . .
H45 H 0.8586 0.6626 0.5687 0.027 Uiso 1 1 calc R U . . .
C46 C 0.7838(13) 0.6368(5) 0.4521(6) 0.027(3) Uani 1 1 d . . . . .
C47 C 0.6851(13) 0.6051(5) 0.4025(7) 0.032(3) Uani 1 1 d . . . . .
H47 H 0.6078 0.5879 0.4263 0.039 Uiso 1 1 calc R U . . .
C48 C 0.6990(14) 0.5984(5) 0.3195(6) 0.031(3) Uani 1 1 d . . . . .
H48 H 0.6313 0.5761 0.2866 0.037 Uiso 1 1 calc R U . . .
C49 C 0.8079(13) 0.6232(5) 0.2830(6) 0.033(3) Uani 1 1 d . . . . .
H49 H 0.8150 0.6182 0.2252 0.039 Uiso 1 1 calc R U . . .
C50 C 0.9096(13) 0.6561(5) 0.3306(8) 0.036(3) Uani 1 1 d . . . . .
H50 H 0.9863 0.6733 0.3061 0.043 Uiso 1 1 calc R U . . .
C51 C 0.8944(13) 0.6627(5) 0.4152(7) 0.031(3) Uani 1 1 d . . . . .
H51 H 0.9612 0.6854 0.4484 0.037 Uiso 1 1 calc R U . . .
C52 C 0.6598(12) 0.6930(5) 0.5659(6) 0.022(2) Uani 1 1 d . . . . .
H52 H 0.5709 0.6762 0.5419 0.026 Uiso 1 1 calc R U . . .
C53 C 0.6488(14) 0.7014(6) 0.6588(7) 0.036(3) Uani 1 1 d . . . . .
H53A H 0.6289 0.6601 0.6837 0.054 Uiso 1 1 calc R U . . .
H53B H 0.5757 0.7316 0.6684 0.054 Uiso 1 1 calc R U . . .
H53C H 0.7347 0.7180 0.6840 0.054 Uiso 1 1 calc R U . . .
C54 C 0.6834(15) 0.7579(5) 0.5261(8) 0.039(3) Uani 1 1 d . . . . .
H54A H 0.7674 0.7768 0.5509 0.058 Uiso 1 1 calc R U . . .
H54B H 0.6070 0.7863 0.5352 0.058 Uiso 1 1 calc R U . . .
H54C H 0.6910 0.7523 0.4665 0.058 Uiso 1 1 calc R U . . .
C55 C 0.1871(12) 0.7624(5) 0.6028(6) 0.022(2) Uani 1 1 d . . . . .
C56 C 0.1443(13) 0.8302(5) 0.6066(6) 0.025(3) Uani 1 1 d . . . . .
C57 C 0.2348(12) 0.8759(5) 0.5762(6) 0.023(2) Uani 1 1 d . . . . .
C58 C 0.1979(12) 0.9405(5) 0.5781(6) 0.027(3) Uani 1 1 d . . . . .
H58 H 0.2565 0.9720 0.5580 0.032 Uiso 1 1 calc R U . . .
C59 C 0.0769(12) 0.9585(5) 0.6089(6) 0.024(2) Uani 1 1 d . . . . .
H59 H 0.0529 1.0024 0.6095 0.028 Uiso 1 1 calc R U . . .
C60 C -0.0097(11) 0.9140(5) 0.6389(6) 0.024(2) Uani 1 1 d . . . . .
H60 H -0.0930 0.9269 0.6596 0.029 Uiso 1 1 calc R U . . .
C61 C 0.0263(13) 0.8495(5) 0.6386(6) 0.031(3) Uani 1 1 d . . . . .
H61 H -0.0317 0.8187 0.6608 0.037 Uiso 1 1 calc R U . . .
C62 C 0.2579(11) 0.5780(5) 0.5933(6) 0.019(2) Uani 1 1 d . U . . .
C63 C 0.2754(13) 0.5089(5) 0.5677(6) 0.028(3) Uani 1 1 d . . . . .
H63 H 0.3592 0.4932 0.5993 0.034 Uiso 1 1 calc R U . . .
C64 C 0.3056(11) 0.5072(5) 0.4757(6) 0.023(2) Uani 1 1 d . . . . .
C65 C 0.4008(11) 0.4674(5) 0.4475(6) 0.024(2) Uani 1 1 d . . . . .
H65 H 0.4518 0.4406 0.4853 0.029 Uiso 1 1 calc R U . . .
C66 C 0.4241(13) 0.4655(6) 0.3640(7) 0.035(3) Uani 1 1 d . . . . .
H66 H 0.4920 0.4378 0.3458 0.042 Uiso 1 1 calc R U . . .
C67 C 0.3524(10) 0.5023(5) 0.3081(6) 0.021(2) Uani 1 1 d . . . . .
H67 H 0.3703 0.5011 0.2512 0.025 Uiso 1 1 calc R U . . .
C68 C 0.2529(12) 0.5416(5) 0.3354(7) 0.026(3) Uani 1 1 d . . . . .
H68 H 0.1989 0.5664 0.2967 0.031 Uiso 1 1 calc R U . . .
C69 C 0.2307(12) 0.5451(5) 0.4194(7) 0.027(3) Uani 1 1 d . . . . .
H69 H 0.1643 0.5736 0.4380 0.033 Uiso 1 1 calc R U . . .
C70 C 0.1609(12) 0.4652(5) 0.5905(6) 0.025(3) Uani 1 1 d . . . . .
H70 H 0.0755 0.4799 0.5596 0.030 Uiso 1 1 calc R U . . .
C71 C 0.1869(11) 0.3958(5) 0.5649(7) 0.023(2) Uani 1 1 d . . . . .
H71A H 0.2757 0.3819 0.5891 0.035 Uiso 1 1 calc R U . . .
H71B H 0.1855 0.3930 0.5045 0.035 Uiso 1 1 calc R U . . .
H71C H 0.1161 0.3681 0.5848 0.035 Uiso 1 1 calc R U . . .
C72 C 0.1389(12) 0.4680(5) 0.6829(6) 0.027(3) Uani 1 1 d . . . . .
H72A H 0.0674 0.4378 0.6956 0.041 Uiso 1 1 calc R U . . .
H72B H 0.1119 0.5113 0.6976 0.041 Uiso 1 1 calc R U . . .
H72C H 0.2234 0.4566 0.7147 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.327(13) . ?
O1 H1 0.8400 . ?
O2 C1 1.221(13) . ?
O3 C3 1.345(13) . ?
O3 H3 0.8400 . ?
O4 C8 1.256(12) . ?
O5 C19 1.311(13) . ?
O5 H5 0.8400 . ?
O6 C19 1.243(13) . ?
O7 C21 1.335(13) . ?
O7 H7 0.8400 . ?
O8 C26 1.235(12) . ?
O9 C37 1.345(13) . ?
O9 H9 0.8400 . ?
O10 C37 1.196(14) . ?
O11 C39 1.348(14) . ?
O11 H11 0.8400 . ?
O12 C44 1.224(12) . ?
O13 C55 1.370(13) . ?
O13 H13 0.8400 . ?
O14 C55 1.177(13) . ?
O15 C57 1.329(13) . ?
O15 H15 0.8400 . ?
O16 C62 1.226(12) . ?
N1 C8 1.340(13) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
N2 C26 1.342(13) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N3 C44 1.318(13) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C62 1.319(13) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
C1 C2 1.492(14) . ?
C2 C7 1.372(15) . ?
C2 C3 1.409(15) . ?
C3 C4 1.382(15) . ?
C4 C5 1.373(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(17) . ?
C5 H2 0.9500 . ?
C6 C7 1.373(16) . ?
C6 H6 0.9500 . ?
C7 H8 0.9500 . ?
C8 C9 1.503(14) . ?
C9 C16 1.526(15) . ?
C9 C10 1.559(13) . ?
C9 H10 1.0000 . ?
C10 C11 1.333(15) . ?
C10 C15 1.378(14) . ?
C11 C12 1.439(14) . ?
C11 H17 0.9500 . ?
C12 C13 1.414(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.360(18) . ?
C13 H18 0.9500 . ?
C14 C15 1.391(15) . ?
C14 H14 0.9500 . ?
C15 H19 0.9500 . ?
C16 C17 1.522(15) . ?
C16 C18 1.549(14) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.447(15) . ?
C20 C25 1.376(16) . ?
C20 C21 1.425(14) . ?
C21 C22 1.392(15) . ?
C22 C23 1.357(16) . ?
C22 H22 0.9500 . ?
C23 C24 1.358(18) . ?
C23 H23 0.9500 . ?
C24 C25 1.393(17) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.534(13) . ?
C27 C28 1.531(14) . ?
C27 C34 1.537(15) . ?
C27 H27 1.0000 . ?
C28 C29 1.373(15) . ?
C28 C33 1.405(17) . ?
C29 C30 1.374(16) . ?
C29 H29 0.9500 . ?
C30 C31 1.417(18) . ?
C30 H30 0.9500 . ?
C31 C32 1.329(16) . ?
C31 H31 0.9500 . ?
C32 C33 1.381(15) . ?
C32 H32 0.9500 . ?
C33 H33 0.9500 . ?
C34 C36 1.511(16) . ?
C34 C35 1.537(15) . ?
C34 H34 1.0000 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.490(15) . ?
C38 C39 1.383(14) . ?
C38 C43 1.384(16) . ?
C39 C40 1.387(15) . ?
C40 C41 1.395(16) . ?
C40 H40 0.9500 . ?
C41 C42 1.382(16) . ?
C41 H41 0.9500 . ?
C42 C43 1.404(15) . ?
C42 H42 0.9500 . ?
C43 H43 0.9500 . ?
C44 C45 1.524(14) . ?
C45 C46 1.524(14) . ?
C45 C52 1.532(14) . ?
C45 H45 1.0000 . ?
C46 C47 1.390(16) . ?
C46 C51 1.391(16) . ?
C47 C48 1.369(15) . ?
C47 H47 0.9500 . ?
C48 C49 1.367(17) . ?
C48 H48 0.9500 . ?
C49 C50 1.406(17) . ?
C49 H49 0.9500 . ?
C50 C51 1.398(16) . ?
C50 H50 0.9500 . ?
C51 H51 0.9500 . ?
C52 C53 1.528(14) . ?
C52 C54 1.530(14) . ?
C52 H52 1.0000 . ?
C53 H53A 0.9800 . ?
C53 H53B 0.9800 . ?
C53 H53C 0.9800 . ?
C54 H54A 0.9800 . ?
C54 H54B 0.9800 . ?
C54 H54C 0.9800 . ?
C55 C56 1.485(14) . ?
C56 C61 1.368(16) . ?
C56 C57 1.422(15) . ?
C57 C58 1.404(15) . ?
C58 C59 1.379(16) . ?
C58 H58 0.9500 . ?
C59 C60 1.378(15) . ?
C59 H59 0.9500 . ?
C60 C61 1.397(15) . ?
C60 H60 0.9500 . ?
C61 H61 0.9500 . ?
C62 C63 1.518(14) . ?
C63 C70 1.522(16) . ?
C63 C64 1.542(14) . ?
C63 H63 1.0000 . ?
C64 C65 1.358(14) . ?
C64 C69 1.386(15) . ?
C65 C66 1.390(14) . ?
C65 H65 0.9500 . ?
C66 C67 1.353(16) . ?
C66 H66 0.9500 . ?
C67 C68 1.379(15) . ?
C67 H67 0.9500 . ?
C68 C69 1.396(15) . ?
C68 H68 0.9500 . ?
C69 H69 0.9500 . ?
C70 C72 1.530(13) . ?
C70 C71 1.539(14) . ?
C70 H70 1.0000 . ?
C71 H71A 0.9800 . ?
C71 H71B 0.9800 . ?
C71 H71C 0.9800 . ?
C72 H72A 0.9800 . ?
C72 H72B 0.9800 . ?
C72 H72C 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
C1 O1 H1 109.5 . . ?
C3 O3 H3 109.5 . . ?
C19 O5 H5 109.5 . . ?
C21 O7 H7 109.5 . . ?
C37 O9 H9 109.5 . . ?
C39 O11 H11 109.5 . . ?
C55 O13 H13 109.5 . . ?
C57 O15 H15 109.5 . . ?
C8 N1 H1A 120.0 . . ?
C8 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C26 N2 H2A 120.0 . . ?
C26 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C44 N3 H3A 120.0 . . ?
C44 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C62 N4 H4A 120.0 . . ?
C62 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?
O2 C1 O1 124.0(10) . . ?
O2 C1 C2 122.8(10) . . ?
O1 C1 C2 113.3(10) . . ?
C7 C2 C3 120.1(10) . . ?
C7 C2 C1 121.6(10) . . ?
C3 C2 C1 118.3(10) . . ?
O3 C3 C4 118.5(10) . . ?
O3 C3 C2 123.2(10) . . ?
C4 C3 C2 118.3(11) . . ?
C5 C4 C3 120.7(11) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.6(12) . . ?
C4 C5 H2 119.7 . . ?
C6 C5 H2 119.7 . . ?
C7 C6 C5 119.6(12) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C2 C7 C6 120.7(11) . . ?
C2 C7 H8 119.7 . . ?
C6 C7 H8 119.7 . . ?
O4 C8 N1 120.2(9) . . ?
O4 C8 C9 121.1(9) . . ?
N1 C8 C9 118.7(9) . . ?
C8 C9 C16 112.5(8) . . ?
C8 C9 C10 109.1(8) . . ?
C16 C9 C10 111.8(9) . . ?
C8 C9 H10 107.8 . . ?
C16 C9 H10 107.8 . . ?
C10 C9 H10 107.8 . . ?
C11 C10 C15 119.6(10) . . ?
C11 C10 C9 121.5(10) . . ?
C15 C10 C9 118.8(9) . . ?
C10 C11 C12 122.3(11) . . ?
C10 C11 H17 118.9 . . ?
C12 C11 H17 118.9 . . ?
C13 C12 C11 117.0(11) . . ?
C13 C12 H12 121.5 . . ?
C11 C12 H12 121.5 . . ?
C14 C13 C12 119.2(10) . . ?
C14 C13 H18 120.4 . . ?
C12 C13 H18 120.4 . . ?
C13 C14 C15 121.7(11) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C10 C15 C14 120.0(11) . . ?
C10 C15 H19 120.0 . . ?
C14 C15 H19 120.0 . . ?
C17 C16 C9 112.2(9) . . ?
C17 C16 C18 109.6(9) . . ?
C9 C16 C18 111.1(9) . . ?
C17 C16 H16 107.9 . . ?
C9 C16 H16 107.9 . . ?
C18 C16 H16 107.9 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O6 C19 O5 121.8(10) . . ?
O6 C19 C20 123.0(10) . . ?
O5 C19 C20 115.1(10) . . ?
C25 C20 C21 117.8(10) . . ?
C25 C20 C19 121.8(10) . . ?
C21 C20 C19 120.4(10) . . ?
O7 C21 C22 120.0(10) . . ?
O7 C21 C20 121.0(10) . . ?
C22 C21 C20 119.0(10) . . ?
C23 C22 C21 120.8(10) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 121.4(11) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C25 119.0(13) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
C20 C25 C24 121.9(12) . . ?
C20 C25 H25 119.0 . . ?
C24 C25 H25 119.0 . . ?
O8 C26 N2 121.7(9) . . ?
O8 C26 C27 121.4(9) . . ?
N2 C26 C27 116.8(9) . . ?
C28 C27 C26 107.6(8) . . ?
C28 C27 C34 112.8(9) . . ?
C26 C27 C34 111.8(8) . . ?
C28 C27 H27 108.2 . . ?
C26 C27 H27 108.2 . . ?
C34 C27 H27 108.2 . . ?
C29 C28 C33 118.1(10) . . ?
C29 C28 C27 120.4(10) . . ?
C33 C28 C27 121.5(10) . . ?
C28 C29 C30 121.3(11) . . ?
C28 C29 H29 119.4 . . ?
C30 C29 H29 119.4 . . ?
C29 C30 C31 119.5(11) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C32 C31 C30 119.4(11) . . ?
C32 C31 H31 120.3 . . ?
C30 C31 H31 120.3 . . ?
C31 C32 C33 121.6(12) . . ?
C31 C32 H32 119.2 . . ?
C33 C32 H32 119.2 . . ?
C32 C33 C28 120.2(11) . . ?
C32 C33 H33 119.9 . . ?
C28 C33 H33 119.9 . . ?
C36 C34 C27 111.8(10) . . ?
C36 C34 C35 110.8(9) . . ?
C27 C34 C35 109.8(9) . . ?
C36 C34 H34 108.1 . . ?
C27 C34 H34 108.1 . . ?
C35 C34 H34 108.1 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
O10 C37 O9 123.6(10) . . ?
O10 C37 C38 123.7(10) . . ?
O9 C37 C38 112.7(10) . . ?
C39 C38 C43 119.7(10) . . ?
C39 C38 C37 118.4(10) . . ?
C43 C38 C37 121.8(10) . . ?
O11 C39 C38 123.1(10) . . ?
O11 C39 C40 115.6(9) . . ?
C38 C39 C40 121.2(10) . . ?
C39 C40 C41 118.4(10) . . ?
C39 C40 H40 120.8 . . ?
C41 C40 H40 120.8 . . ?
C42 C41 C40 121.5(10) . . ?
C42 C41 H41 119.3 . . ?
C40 C41 H41 119.3 . . ?
C41 C42 C43 118.8(11) . . ?
C41 C42 H42 120.6 . . ?
C43 C42 H42 120.6 . . ?
C38 C43 C42 120.2(11) . . ?
C38 C43 H43 119.9 . . ?
C42 C43 H43 119.9 . . ?
O12 C44 N3 121.7(9) . . ?
O12 C44 C45 123.8(9) . . ?
N3 C44 C45 114.6(9) . . ?
C46 C45 C44 107.4(8) . . ?
C46 C45 C52 114.4(9) . . ?
C44 C45 C52 112.9(8) . . ?
C46 C45 H45 107.2 . . ?
C44 C45 H45 107.2 . . ?
C52 C45 H45 107.2 . . ?
C47 C46 C51 118.6(10) . . ?
C47 C46 C45 121.4(10) . . ?
C51 C46 C45 120.0(10) . . ?
C48 C47 C46 120.3(12) . . ?
C48 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
C49 C48 C47 121.5(11) . . ?
C49 C48 H48 119.3 . . ?
C47 C48 H48 119.3 . . ?
C48 C49 C50 120.2(10) . . ?
C48 C49 H49 119.9 . . ?
C50 C49 H49 119.9 . . ?
C51 C50 C49 117.8(11) . . ?
C51 C50 H50 121.1 . . ?
C49 C50 H50 121.1 . . ?
C46 C51 C50 121.6(12) . . ?
C46 C51 H51 119.2 . . ?
C50 C51 H51 119.2 . . ?
C53 C52 C54 109.7(9) . . ?
C53 C52 C45 113.5(9) . . ?
C54 C52 C45 110.4(9) . . ?
C53 C52 H52 107.7 . . ?
C54 C52 H52 107.7 . . ?
C45 C52 H52 107.7 . . ?
C52 C53 H53A 109.5 . . ?
C52 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C52 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C52 C54 H54A 109.5 . . ?
C52 C54 H54B 109.5 . . ?
H54A C54 H54B 109.5 . . ?
C52 C54 H54C 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
O14 C55 O13 122.1(10) . . ?
O14 C55 C56 125.3(10) . . ?
O13 C55 C56 112.5(10) . . ?
C61 C56 C57 120.3(10) . . ?
C61 C56 C55 123.5(10) . . ?
C57 C56 C55 116.2(10) . . ?
O15 C57 C58 118.1(10) . . ?
O15 C57 C56 123.7(10) . . ?
C58 C57 C56 118.2(11) . . ?
C59 C58 C57 120.3(10) . . ?
C59 C58 H58 119.8 . . ?
C57 C58 H58 119.8 . . ?
C60 C59 C58 121.1(10) . . ?
C60 C59 H59 119.4 . . ?
C58 C59 H59 119.4 . . ?
C59 C60 C61 119.3(11) . . ?
C59 C60 H60 120.3 . . ?
C61 C60 H60 120.3 . . ?
C56 C61 C60 120.7(11) . . ?
C56 C61 H61 119.6 . . ?
C60 C61 H61 119.6 . . ?
O16 C62 N4 122.7(9) . . ?
O16 C62 C63 121.4(9) . . ?
N4 C62 C63 115.9(10) . . ?
C62 C63 C70 114.0(10) . . ?
C62 C63 C64 108.7(8) . . ?
C70 C63 C64 114.7(9) . . ?
C62 C63 H63 106.3 . . ?
C70 C63 H63 106.3 . . ?
C64 C63 H63 106.3 . . ?
C65 C64 C69 118.8(10) . . ?
C65 C64 C63 121.6(10) . . ?
C69 C64 C63 119.6(9) . . ?
C64 C65 C66 120.6(11) . . ?
C64 C65 H65 119.7 . . ?
C66 C65 H65 119.7 . . ?
C67 C66 C65 121.6(12) . . ?
C67 C66 H66 119.2 . . ?
C65 C66 H66 119.2 . . ?
C66 C67 C68 118.5(10) . . ?
C66 C67 H67 120.8 . . ?
C68 C67 H67 120.8 . . ?
C67 C68 C69 120.6(10) . . ?
C67 C68 H68 119.7 . . ?
C69 C68 H68 119.7 . . ?
C64 C69 C68 119.9(10) . . ?
C64 C69 H69 120.0 . . ?
C68 C69 H69 120.0 . . ?
C63 C70 C72 111.9(9) . . ?
C63 C70 C71 111.3(9) . . ?
C72 C70 C71 109.7(8) . . ?
C63 C70 H70 107.9 . . ?
C72 C70 H70 107.9 . . ?
C71 C70 H70 107.9 . . ?
C70 C71 H71A 109.5 . . ?
C70 C71 H71B 109.5 . . ?
H71A C71 H71B 109.5 . . ?
C70 C71 H71C 109.5 . . ?
H71A C71 H71C 109.5 . . ?
H71B C71 H71C 109.5 . . ?
C70 C72 H72A 109.5 . . ?
C70 C72 H72B 109.5 . . ?
H72A C72 H72B 109.5 . . ?
C70 C72 H72C 109.5 . . ?
H72A C72 H72C 109.5 . . ?
H72B C72 H72C 109.5 . . ?

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.105

_shelxl_version_number           2014-3



####################################################################### 
# 
# 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_Form_III
_database_code_depnum_ccdc_archive 'CCDC 1480081'
_audit_update_record             
;
2016-05-16 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            
'3-Methyl-2-Phenylbutyramide-Salicylic acid-Polymorph III'
_chemical_formula_moiety         'C11 H15 N O, C7 H6 O3'
_chemical_formula_sum            'C18 H21 N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         315.36

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   10.0661(14)
_cell_length_b                   21.081(3)
_cell_length_c                   16.584(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.060(4)
_cell_angle_gamma                90
_cell_volume                     3465.1(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4485
_cell_measurement_theta_min      2.2706
_cell_measurement_theta_max      21.6600
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1344

_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker SMART X2S'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            46406
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         25.12
_diffrn_reflns_theta_full        25.12
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             6123
_reflns_number_gt                3564
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1506
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.012
_refine_ls_number_reflns         6123
_refine_ls_number_parameters     452
_refine_ls_number_restraints     8
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+0.9202P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.280
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0010(3)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.9070(2) 0.61056(11) 0.87465(15) 0.0617(6) Uani d . . D 1 . .
H H1A 0.898(3) 0.6524(3) 0.8785(19) 0.096(11) Uiso d . . D 1 . .
H H1B 0.9830(15) 0.5928(12) 0.8650(16) 0.075(9) Uiso d . . D 1 . .
C C2 0.7927(2) 0.57870(11) 0.85619(14) 0.0461(6) Uani d . . . 1 . .
O O3 0.68258(16) 0.60368(8) 0.86165(11) 0.0576(5) Uani d . . . 1 . .
C C4 0.8023(2) 0.51166(10) 0.82479(13) 0.0433(6) Uani d . . . 1 . .
H H4 0.8905 0.4949 0.8502 0.052 Uiso calc U . R 1 . .
C C5 0.6947(2) 0.46678(11) 0.84766(14) 0.0476(6) Uani d . . . 1 . .
H H5 0.6059 0.4827 0.8219 0.057 Uiso calc U . R 1 . .
C C6 0.7110(3) 0.40005(12) 0.81557(18) 0.0663(8) Uani d . . . 1 . .
H H6A 0.7988 0.3841 0.8385 0.099 Uiso calc U . R 1 . .
H H6B 0.7014 0.4012 0.757 0.099 Uiso calc U . R 1 . .
H H6C 0.6431 0.3729 0.831 0.099 Uiso calc U . R 1 . .
C C7 0.6990(3) 0.46515(14) 0.93954(16) 0.0737(8) Uani d . . . 1 . .
H H7A 0.6317 0.4363 0.952 0.111 Uiso calc U . R 1 . .
H H7B 0.6816 0.5068 0.9585 0.111 Uiso calc U . R 1 . .
H H7C 0.7865 0.4513 0.9663 0.111 Uiso calc U . R 1 . .
C C8 0.8011(2) 0.51546(11) 0.73294(14) 0.0446(6) Uani d . . . 1 . .
C C9 0.8960(3) 0.48295(13) 0.69833(16) 0.0615(7) Uani d . . . 1 . .
H H9 0.9622 0.4595 0.7317 0.074 Uiso calc U . R 1 . .
C C10 0.8941(3) 0.48474(16) 0.61496(19) 0.0783(9) Uani d . . . 1 . .
H H10 0.9584 0.4625 0.5923 0.094 Uiso calc U . R 1 . .
C C11 0.7970(4) 0.51944(16) 0.56558(18) 0.0796(9) Uani d . . . 1 . .
H H11 0.7957 0.5208 0.5094 0.095 Uiso calc U . R 1 . .
C C12 0.7019(3) 0.55211(13) 0.59890(17) 0.0710(8) Uani d . . . 1 . .
H H12 0.6363 0.5757 0.5653 0.085 Uiso calc U . R 1 . .
C C13 0.7033(3) 0.55004(12) 0.68229(16) 0.0564(7) Uani d . . . 1 . .
H H13 0.6381 0.572 0.7045 0.068 Uiso calc U . R 1 . .
N N21 0.4041(2) 0.55625(11) 0.86428(14) 0.0562(6) Uani d . . D 1 . .
H H21A 0.399(3) 0.5151(4) 0.8759(15) 0.070(8) Uiso d . . D 1 . .
H H21B 0.4822(13) 0.5742(11) 0.8588(15) 0.065(8) Uiso d . . D 1 . .
C C22 0.2892(2) 0.58655(11) 0.84265(13) 0.0442(6) Uani d . . . 1 . .
O O23 0.17894(15) 0.56128(7) 0.84883(10) 0.0512(4) Uani d . . . 1 . .
C C24 0.2959(2) 0.65257(10) 0.80689(14) 0.0456(6) Uani d . . . 1 . .
H H24 0.3858 0.6697 0.828 0.055 Uiso calc U . R 1 . .
C C25 0.1920(3) 0.69835(11) 0.83324(15) 0.0531(6) Uani d . . . 1 . .
H H25 0.1014 0.6818 0.8128 0.064 Uiso calc U . R 1 . .
C C26 0.2109(3) 0.70278(14) 0.92593(17) 0.0814(9) Uani d . . . 1 . .
H H26A 0.2997 0.7184 0.947 0.122 Uiso calc U . R 1 . .
H H26B 0.1999 0.6615 0.9483 0.122 Uiso calc U . R 1 . .
H H26C 0.1449 0.7312 0.9411 0.122 Uiso calc U . R 1 . .
C C27 0.2035(3) 0.76408(12) 0.79636(19) 0.0760(9) Uani d . . . 1 . .
H H27A 0.1393 0.7921 0.8142 0.114 Uiso calc U . R 1 . .
H H27B 0.1854 0.7612 0.7377 0.114 Uiso calc U . R 1 . .
H H27C 0.293 0.7803 0.814 0.114 Uiso calc U . R 1 . .
C C28 0.2835(2) 0.64666(10) 0.71487(14) 0.0459(6) Uani d . . . 1 . .
C C29 0.1763(3) 0.61438(12) 0.66841(15) 0.0539(6) Uani d . . . 1 . .
H H29 0.1114 0.5957 0.6943 0.065 Uiso calc U . R 1 . .
C C30 0.1647(3) 0.60966(13) 0.58464(17) 0.0637(7) Uani d . . . 1 . .
H H30 0.0927 0.5876 0.5545 0.076 Uiso calc U . R 1 . .
C C31 0.2594(3) 0.63753(15) 0.54542(18) 0.0748(8) Uani d . . . 1 . .
H H31 0.2523 0.6341 0.4889 0.09 Uiso calc U . R 1 . .
C C32 0.3643(3) 0.67044(16) 0.5904(2) 0.0816(9) Uani d . . . 1 . .
H H32 0.4273 0.6903 0.564 0.098 Uiso calc U . R 1 . .
C C33 0.3773(3) 0.67449(14) 0.67459(17) 0.0677(8) Uani d . . . 1 . .
H H33 0.4502 0.6962 0.7044 0.081 Uiso calc U . R 1 . .
O O41 0.34922(19) 0.42062(9) 0.88322(15) 0.0859(7) Uani d . . . 1 . .
C C42 0.2360(3) 0.40269(12) 0.88979(16) 0.0559(7) Uani d . . . 1 . .
O O43 0.13718(18) 0.44328(9) 0.88952(12) 0.0631(5) Uani d . . D 1 . .
H H43 0.157(3) 0.4789(6) 0.8791(19) 0.096(12) Uiso d . . D 1 . .
C C44 0.2010(2) 0.33613(11) 0.89782(16) 0.0544(6) Uani d . . . 1 . .
C C45 0.0759(3) 0.31803(13) 0.91392(17) 0.0661(7) Uani d . . . 1 . .
H H45 0.0137 0.349 0.9219 0.079 Uiso calc U . R 1 . .
C C46 0.0420(3) 0.25525(15) 0.9183(2) 0.0825(9) Uani d . . . 1 . .
H H46 -0.042 0.2439 0.9298 0.099 Uiso calc U . R 1 . .
C C47 0.1329(3) 0.20926(15) 0.9056(2) 0.0910(11) Uani d . . . 1 . .
H H47 0.1104 0.1666 0.9086 0.109 Uiso calc U . R 1 . .
C C48 0.2554(4) 0.22575(15) 0.8888(3) 0.1131(14) Uani d . . . 1 . .
H H48 0.3158 0.1944 0.8791 0.136 Uiso calc U . R 1 . .
C C49 0.2911(3) 0.28920(15) 0.8860(3) 0.0940(11) Uani d . . . 1 . .
O O50 0.4140(3) 0.30220(13) 0.8683(3) 0.188(2) Uani d . . D 1 . .
H H50 0.418(6) 0.3399(4) 0.863(3) 0.21(2) Uiso d . . D 1 . .
O O51 0.8320(2) 0.74686(9) 0.85099(14) 0.0830(6) Uani d . . . 1 . .
C C52 0.7222(3) 0.76463(13) 0.86565(17) 0.0604(7) Uani d . . . 1 . .
O O53 0.6323(2) 0.72419(10) 0.88354(15) 0.0771(6) Uani d . . D 1 . .
H H53 0.655(4) 0.6878(6) 0.880(2) 0.127(15) Uiso d . . D 1 . .
C C54 0.6824(3) 0.83146(12) 0.86365(16) 0.0551(6) Uani d . . . 1 . .
C C55 0.5636(3) 0.85094(13) 0.88799(17) 0.0649(7) Uani d . . . 1 . .
H H55 0.5086 0.821 0.907 0.078 Uiso calc U . R 1 . .
C C56 0.5260(3) 0.91372(14) 0.88446(19) 0.0744(8) Uani d . . . 1 . .
H H56 0.447 0.9264 0.9017 0.089 Uiso calc U . R 1 . .
C C57 0.6076(3) 0.95789(14) 0.85481(19) 0.0769(9) Uani d . . . 1 . .
H H57 0.5822 1.0004 0.8515 0.092 Uiso calc U . R 1 . .
C C58 0.7235(3) 0.94009(14) 0.83057(19) 0.0759(9) Uani d . . . 1 . .
H H58 0.777 0.9703 0.8107 0.091 Uiso calc U . R 1 . .
C C59 0.7630(3) 0.87710(13) 0.83521(18) 0.0666(8) Uani d . . . 1 . .
O O60 0.8799(3) 0.86238(12) 0.80991(19) 0.1081(9) Uani d . . D 1 . .
H H60 0.888(4) 0.8253(6) 0.821(3) 0.146(18) Uiso d . . D 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C2 . 1.321(3) ?
N1 H1A . 0.890(5) ?
N1 H1B . 0.892(5) ?
C2 O3 . 1.245(3) ?
C2 C4 . 1.515(3) ?
C4 C8 . 1.523(3) ?
C4 C5 . 1.535(3) ?
C4 H4 . 0.98 ?
C5 C7 . 1.517(3) ?
C5 C6 . 1.523(3) ?
C5 H5 . 0.98 ?
C6 H6A . 0.96 ?
C6 H6B . 0.96 ?
C6 H6C . 0.96 ?
C7 H7A . 0.96 ?
C7 H7B . 0.96 ?
C7 H7C . 0.96 ?
C8 C9 . 1.380(3) ?
C8 C13 . 1.385(3) ?
C9 C10 . 1.380(4) ?
C9 H9 . 0.93 ?
C10 C11 . 1.372(4) ?
C10 H10 . 0.93 ?
C11 C12 . 1.371(4) ?
C11 H11 . 0.93 ?
C12 C13 . 1.381(4) ?
C12 H12 . 0.93 ?
C13 H13 . 0.93 ?
N21 C22 . 1.316(3) ?
N21 H21A . 0.892(5) ?
N21 H21B . 0.891(5) ?
C22 O23 . 1.251(3) ?
C22 C24 . 1.519(3) ?
C24 C28 . 1.515(3) ?
C24 C25 . 1.541(3) ?
C24 H24 . 0.98 ?
C25 C26 . 1.518(4) ?
C25 C27 . 1.527(3) ?
C25 H25 . 0.98 ?
C26 H26A . 0.96 ?
C26 H26B . 0.96 ?
C26 H26C . 0.96 ?
C27 H27A . 0.96 ?
C27 H27B . 0.96 ?
C27 H27C . 0.96 ?
C28 C33 . 1.380(3) ?
C28 C29 . 1.389(3) ?
C29 C30 . 1.377(3) ?
C29 H29 . 0.93 ?
C30 C31 . 1.376(4) ?
C30 H30 . 0.93 ?
C31 C32 . 1.370(4) ?
C31 H31 . 0.93 ?
C32 C33 . 1.382(4) ?
C32 H32 . 0.93 ?
C33 H33 . 0.93 ?
O41 C42 . 1.224(3) ?
C42 O43 . 1.311(3) ?
C42 C44 . 1.458(3) ?
O43 H43 . 0.803(5) ?
C44 C49 . 1.379(4) ?
C44 C45 . 1.387(3) ?
C45 C46 . 1.372(4) ?
C45 H45 . 0.93 ?
C46 C47 . 1.375(4) ?
C46 H46 . 0.93 ?
C47 C48 . 1.356(4) ?
C47 H47 . 0.93 ?
C48 C49 . 1.388(4) ?
C48 H48 . 0.93 ?
C49 O50 . 1.349(4) ?
O50 H50 . 0.802(5) ?
O51 C52 . 1.231(3) ?
C52 O53 . 1.315(3) ?
C52 C54 . 1.464(4) ?
O53 H53 . 0.804(5) ?
C54 C55 . 1.389(4) ?
C54 C59 . 1.393(4) ?
C55 C56 . 1.375(4) ?
C55 H55 . 0.93 ?
C56 C57 . 1.387(4) ?
C56 H56 . 0.93 ?
C57 C58 . 1.352(4) ?
C57 H57 . 0.93 ?
C58 C59 . 1.384(4) ?
C58 H58 . 0.93 ?
C59 O60 . 1.353(4) ?
O60 H60 . 0.803(5) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N1 H1A . . 115.(2) ?
C2 N1 H1B . . 119.0(18) ?
H1A N1 H1B . . 122.(3) ?
O3 C2 N1 . . 121.2(2) ?
O3 C2 C4 . . 122.0(2) ?
N1 C2 C4 . . 116.7(2) ?
C2 C4 C8 . . 107.74(19) ?
C2 C4 C5 . . 113.60(19) ?
C8 C4 C5 . . 113.39(18) ?
C2 C4 H4 . . 107.3 ?
C8 C4 H4 . . 107.3 ?
C5 C4 H4 . . 107.3 ?
C7 C5 C6 . . 110.1(2) ?
C7 C5 C4 . . 111.4(2) ?
C6 C5 C4 . . 111.1(2) ?
C7 C5 H5 . . 108.0 ?
C6 C5 H5 . . 108.0 ?
C4 C5 H5 . . 108.0 ?
C5 C6 H6A . . 109.5 ?
C5 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C5 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C5 C7 H7A . . 109.5 ?
C5 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C5 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
C9 C8 C13 . . 118.7(2) ?
C9 C8 C4 . . 120.3(2) ?
C13 C8 C4 . . 121.0(2) ?
C10 C9 C8 . . 120.9(3) ?
C10 C9 H9 . . 119.5 ?
C8 C9 H9 . . 119.5 ?
C11 C10 C9 . . 119.8(3) ?
C11 C10 H10 . . 120.1 ?
C9 C10 H10 . . 120.1 ?
C12 C11 C10 . . 120.1(3) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C11 C12 C13 . . 120.1(3) ?
C11 C12 H12 . . 119.9 ?
C13 C12 H12 . . 119.9 ?
C12 C13 C8 . . 120.4(3) ?
C12 C13 H13 . . 119.8 ?
C8 C13 H13 . . 119.8 ?
C22 N21 H21A . . 116.4(18) ?
C22 N21 H21B . . 121.0(17) ?
H21A N21 H21B . . 122.(2) ?
O23 C22 N21 . . 121.4(2) ?
O23 C22 C24 . . 121.5(2) ?
N21 C22 C24 . . 117.0(2) ?
C28 C24 C22 . . 108.45(19) ?
C28 C24 C25 . . 113.36(18) ?
C22 C24 C25 . . 112.61(18) ?
C28 C24 H24 . . 107.4 ?
C22 C24 H24 . . 107.4 ?
C25 C24 H24 . . 107.4 ?
C26 C25 C27 . . 110.2(2) ?
C26 C25 C24 . . 110.8(2) ?
C27 C25 C24 . . 110.6(2) ?
C26 C25 H25 . . 108.4 ?
C27 C25 H25 . . 108.4 ?
C24 C25 H25 . . 108.4 ?
C25 C26 H26A . . 109.5 ?
C25 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C25 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C25 C27 H27A . . 109.5 ?
C25 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C25 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C33 C28 C29 . . 118.1(2) ?
C33 C28 C24 . . 120.7(2) ?
C29 C28 C24 . . 121.2(2) ?
C30 C29 C28 . . 121.0(2) ?
C30 C29 H29 . . 119.5 ?
C28 C29 H29 . . 119.5 ?
C31 C30 C29 . . 120.2(3) ?
C31 C30 H30 . . 119.9 ?
C29 C30 H30 . . 119.9 ?
C32 C31 C30 . . 119.4(3) ?
C32 C31 H31 . . 120.3 ?
C30 C31 H31 . . 120.3 ?
C31 C32 C33 . . 120.6(3) ?
C31 C32 H32 . . 119.7 ?
C33 C32 H32 . . 119.7 ?
C28 C33 C32 . . 120.7(3) ?
C28 C33 H33 . . 119.6 ?
C32 C33 H33 . . 119.6 ?
O41 C42 O43 . . 121.0(2) ?
O41 C42 C44 . . 123.3(2) ?
O43 C42 C44 . . 115.7(2) ?
C42 O43 H43 . . 113.(2) ?
C49 C44 C45 . . 118.2(3) ?
C49 C44 C42 . . 120.2(2) ?
C45 C44 C42 . . 121.6(2) ?
C46 C45 C44 . . 121.2(3) ?
C46 C45 H45 . . 119.4 ?
C44 C45 H45 . . 119.4 ?
C45 C46 C47 . . 119.6(3) ?
C45 C46 H46 . . 120.2 ?
C47 C46 H46 . . 120.2 ?
C48 C47 C46 . . 120.3(3) ?
C48 C47 H47 . . 119.8 ?
C46 C47 H47 . . 119.8 ?
C47 C48 C49 . . 120.3(3) ?
C47 C48 H48 . . 119.9 ?
C49 C48 H48 . . 119.9 ?
O50 C49 C44 . . 122.4(3) ?
O50 C49 C48 . . 117.1(3) ?
C44 C49 C48 . . 120.4(3) ?
C49 O50 H50 . . 107.(4) ?
O51 C52 O53 . . 121.6(3) ?
O51 C52 C54 . . 122.7(3) ?
O53 C52 C54 . . 115.6(2) ?
C52 O53 H53 . . 113.(3) ?
C55 C54 C59 . . 118.4(2) ?
C55 C54 C52 . . 121.6(2) ?
C59 C54 C52 . . 119.9(2) ?
C56 C55 C54 . . 121.1(3) ?
C56 C55 H55 . . 119.4 ?
C54 C55 H55 . . 119.4 ?
C55 C56 C57 . . 119.1(3) ?
C55 C56 H56 . . 120.5 ?
C57 C56 H56 . . 120.5 ?
C58 C57 C56 . . 120.9(3) ?
C58 C57 H57 . . 119.5 ?
C56 C57 H57 . . 119.5 ?
C57 C58 C59 . . 120.3(3) ?
C57 C58 H58 . . 119.9 ?
C59 C58 H58 . . 119.9 ?
O60 C59 C58 . . 117.4(3) ?
O60 C59 C54 . . 122.4(3) ?
C58 C59 C54 . . 120.2(3) ?
C59 O60 H60 . . 102.(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O51 . 0.890(5) 2.124(11) 2.979(3) 161.(3) ?
N1 H1B O23 1_655 0.892(5) 2.142(7) 3.028(3) 172.(3) ?
N21 H21A O41 . 0.892(5) 2.062(8) 2.939(3) 168.(2) ?
N21 H21B O3 . 0.891(5) 2.103(7) 2.983(3) 169.(2) ?
O43 H43 O23 . 0.803(5) 1.832(7) 2.630(2) 173.(3) ?
O50 H50 O41 . 0.802(5) 1.89(3) 2.603(3) 148.(5) ?
O53 H53 O3 . 0.804(5) 1.831(8) 2.628(3) 171.(4) ?
O60 H60 O51 . 0.803(5) 1.844(19) 2.596(3) 155.(5) ?



