# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_MaproptileneCarbamate
_database_code_depnum_ccdc_archive 'CCDC 1947399'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2019-08-15 deposited with the CCDC.	2019-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C21 H22 N O2), 2(C20 H24 N), H2 O'
_chemical_formula_sum            'C82 H94 N4 O5'
_chemical_formula_weight         1215.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.9101(4)
_cell_length_b                   11.0141(5)
_cell_length_c                   17.3483(8)
_cell_angle_alpha                84.2353(14)
_cell_angle_beta                 78.5292(13)
_cell_angle_gamma                85.5819(13)
_cell_volume                     1657.22(13)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.6088
_cell_measurement_theta_max      80.1924

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             654
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.582
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6582
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest CMOS diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            22153
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.609
_diffrn_reflns_theta_max         80.576
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6778
_reflns_number_gt                6205
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Apex3 v2018.7-2 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev946 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
A water molecule is disordered over two mutually exclusive positions 
related by an inversion center and was refined as half occupied. 

Water H atom positions were refined and O-H were restrained to 0.84(2) 
Angstrom.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0449P)²+0.6118P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0054(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6778
_refine_ls_number_parameters     424
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1114
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_restrained_S_all      1.104
_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 0.26600(11) 0.37976(9) 0.02212(6) 0.0353(2) Uani 1 1 d . . . . .
O2 O 0.04141(11) 0.29650(10) 0.03071(6) 0.0340(2) Uani 1 1 d . . . . .
O3 O 0.5579(3) 0.4313(2) 0.04763(14) 0.0412(5) Uani 0.5 1 d D . P A -1
H3A H 0.594(5) 0.498(3) 0.026(2) 0.062 Uiso 0.5 1 d D U P B -1
H3B H 0.471(3) 0.424(4) 0.035(3) 0.062 Uiso 0.5 1 d D U P C -1
N1 N 0.09213(12) 0.57637(9) 0.07779(6) 0.0222(2) Uani 1 1 d . . . . .
H1A H 0.048674 0.613954 0.037754 0.027 Uiso 1 1 calc R U . . .
H1AB H 0.150477 0.510177 0.059178 0.027 Uiso 1 1 calc R U . . .
N2 N 0.25584(13) 0.17380(10) 0.03149(6) 0.0265(2) Uani 1 1 d . . . . .
C1 C 0.62936(13) 0.72345(11) 0.23748(7) 0.0198(2) Uani 1 1 d . . . . .
C2 C 0.68647(14) 0.81456(11) 0.18008(7) 0.0233(3) Uani 1 1 d . . . . .
H2 H 0.638099 0.836165 0.136124 0.028 Uiso 1 1 calc R U . . .
C3 C 0.81491(15) 0.87411(12) 0.18723(8) 0.0272(3) Uani 1 1 d . . . . .
H3 H 0.852438 0.937577 0.148600 0.033 Uiso 1 1 calc R U . . .
C4 C 0.88816(15) 0.84152(12) 0.25014(8) 0.0278(3) Uani 1 1 d . . . . .
H4 H 0.975171 0.882933 0.254813 0.033 Uiso 1 1 calc R U . . .
C5 C 0.83413(14) 0.74782(12) 0.30668(8) 0.0251(3) Uani 1 1 d . . . . .
H5 H 0.885805 0.723813 0.349173 0.030 Uiso 1 1 calc R U . . .
C6 C 0.70517(13) 0.68996(11) 0.30071(7) 0.0207(2) Uani 1 1 d . . . . .
C7 C 0.63152(14) 0.58891(11) 0.35815(7) 0.0223(3) Uani 1 1 d . . . . .
H7 H 0.685174 0.568935 0.403688 0.027 Uiso 1 1 calc R U . . .
C8 C 0.46580(14) 0.63234(11) 0.38445(7) 0.0219(3) Uani 1 1 d . . . . .
C9 C 0.39180(15) 0.64123(12) 0.46219(7) 0.0258(3) Uani 1 1 d . . . . .
H9 H 0.444278 0.615525 0.504157 0.031 Uiso 1 1 calc R U . . .
C10 C 0.24083(15) 0.68783(13) 0.47829(8) 0.0291(3) Uani 1 1 d . . . . .
H10 H 0.189007 0.692839 0.531410 0.035 Uiso 1 1 calc R U . . .
C11 C 0.16553(15) 0.72715(13) 0.41664(8) 0.0286(3) Uani 1 1 d . . . . .
H11 H 0.063112 0.761218 0.427764 0.034 Uiso 1 1 calc R U . . .
C12 C 0.23918(14) 0.71700(12) 0.33849(8) 0.0242(3) Uani 1 1 d . . . . .
H12 H 0.186823 0.743610 0.296603 0.029 Uiso 1 1 calc R U . . .
C13 C 0.38919(14) 0.66790(11) 0.32207(7) 0.0203(2) Uani 1 1 d . . . . .
C14 C 0.63230(15) 0.47711(11) 0.31031(7) 0.0246(3) Uani 1 1 d . . . . .
H14A H 0.739336 0.448183 0.289585 0.030 Uiso 1 1 calc R U . . .
H14B H 0.580714 0.409580 0.345050 0.030 Uiso 1 1 calc R U . . .
C15 C 0.54811(14) 0.51395(11) 0.24136(7) 0.0221(3) Uani 1 1 d . . . . .
H15A H 0.460427 0.461819 0.246280 0.027 Uiso 1 1 calc R U . . .
H15B H 0.618846 0.500155 0.190861 0.027 Uiso 1 1 calc R U . . .
C16 C 0.48813(13) 0.65160(11) 0.24037(7) 0.0197(2) Uani 1 1 d . . . . .
C17 C 0.40742(14) 0.68886(11) 0.17096(7) 0.0226(3) Uani 1 1 d . . . . .
H17A H 0.485783 0.691826 0.121677 0.027 Uiso 1 1 calc R U . . .
H17B H 0.360127 0.772606 0.176681 0.027 Uiso 1 1 calc R U . . .
C18 C 0.28283(14) 0.60512(11) 0.16207(7) 0.0229(3) Uani 1 1 d . . . . .
H18A H 0.331025 0.524938 0.146562 0.028 Uiso 1 1 calc R U . . .
H18B H 0.211543 0.591346 0.213315 0.028 Uiso 1 1 calc R U . . .
C19 C 0.19415(14) 0.66232(11) 0.10005(7) 0.0242(3) Uani 1 1 d . . . . .
H19A H 0.131221 0.734488 0.120436 0.029 Uiso 1 1 calc R U . . .
H19B H 0.267745 0.691050 0.052281 0.029 Uiso 1 1 calc R U . . .
C20 C -0.03126(15) 0.53357(13) 0.14284(8) 0.0295(3) Uani 1 1 d . . . . .
H20A H -0.090531 0.604224 0.165960 0.044 Uiso 1 1 calc R U . . .
H20B H 0.013989 0.483738 0.183414 0.044 Uiso 1 1 calc R U . . .
H20C H -0.099056 0.484384 0.122294 0.044 Uiso 1 1 calc R U . . .
C21 C 0.58673(15) 0.16407(11) 0.26546(7) 0.0236(3) Uani 1 1 d . . . . .
C22 C 0.70392(16) 0.20219(12) 0.20447(8) 0.0289(3) Uani 1 1 d . . . . .
H22 H 0.682520 0.228148 0.153675 0.035 Uiso 1 1 calc R U . . .
C23 C 0.85300(17) 0.20236(13) 0.21781(10) 0.0364(3) Uani 1 1 d . . . . .
H23 H 0.932988 0.228597 0.175955 0.044 Uiso 1 1 calc R U . . .
C24 C 0.88553(17) 0.16457(14) 0.29162(10) 0.0378(3) Uani 1 1 d . . . . .
H24 H 0.987936 0.162902 0.299894 0.045 Uiso 1 1 calc R U . . .
C25 C 0.76831(17) 0.12913(13) 0.35350(9) 0.0335(3) Uani 1 1 d . . . . .
H25 H 0.790072 0.104193 0.404352 0.040 Uiso 1 1 calc R U . . .
C26 C 0.61935(16) 0.13027(11) 0.34078(8) 0.0265(3) Uani 1 1 d . . . . .
C27 C 0.48083(16) 0.09844(12) 0.40268(8) 0.0283(3) Uani 1 1 d . . . . .
H27 H 0.506704 0.081272 0.456381 0.034 Uiso 1 1 calc R U . . .
C28 C 0.36130(15) 0.20299(12) 0.39987(7) 0.0259(3) Uani 1 1 d . . . . .
C29 C 0.28665(16) 0.26557(13) 0.46351(8) 0.0315(3) Uani 1 1 d . . . . .
H29 H 0.308623 0.243389 0.514629 0.038 Uiso 1 1 calc R U . . .
C30 C 0.17974(16) 0.36074(14) 0.45202(8) 0.0333(3) Uani 1 1 d . . . . .
H30 H 0.130025 0.404923 0.495214 0.040 Uiso 1 1 calc R U . . .
C31 C 0.14525(16) 0.39156(13) 0.37806(9) 0.0320(3) Uani 1 1 d . . . . .
H31 H 0.071851 0.456762 0.370655 0.038 Uiso 1 1 calc R U . . .
C32 C 0.21784(15) 0.32725(12) 0.31411(8) 0.0263(3) Uani 1 1 d . . . . .
H32 H 0.192562 0.347655 0.263523 0.032 Uiso 1 1 calc R U . . .
C33 C 0.32675(14) 0.23365(11) 0.32476(7) 0.0232(3) Uani 1 1 d . . . . .
C34 C 0.41473(18) -0.01360(12) 0.37628(8) 0.0319(3) Uani 1 1 d . . . . .
H34A H 0.490241 -0.084498 0.375411 0.038 Uiso 1 1 calc R U . . .
H34B H 0.320015 -0.035971 0.413934 0.038 Uiso 1 1 calc R U . . .
C35 C 0.37876(16) 0.01970(11) 0.29290(8) 0.0259(3) Uani 1 1 d . . . . .
H35A H 0.268618 0.009952 0.294524 0.031 Uiso 1 1 calc R U . . .
H35B H 0.439060 -0.037105 0.256081 0.031 Uiso 1 1 calc R U . . .
C36 C 0.41796(15) 0.15471(11) 0.26163(7) 0.0228(3) Uani 1 1 d . . . . .
C37 C 0.37824(15) 0.18927(12) 0.18030(7) 0.0253(3) Uani 1 1 d . . . . .
H37A H 0.415324 0.271369 0.161000 0.030 Uiso 1 1 calc R U . . .
H37B H 0.265148 0.195489 0.186280 0.030 Uiso 1 1 calc R U . . .
C38 C 0.44396(16) 0.10126(12) 0.11700(7) 0.0270(3) Uani 1 1 d . . . . .
H38A H 0.555433 0.085365 0.115195 0.032 Uiso 1 1 calc R U . . .
H38B H 0.394624 0.022444 0.131106 0.032 Uiso 1 1 calc R U . . .
C39 C 0.41703(15) 0.15441(12) 0.03585(7) 0.0256(3) Uani 1 1 d . . . . .
H39A H 0.466155 0.233384 0.022343 0.031 Uiso 1 1 calc R U . . .
H39B H 0.467181 0.098229 -0.003968 0.031 Uiso 1 1 calc R U . . .
C40 C 0.16830(19) 0.06663(14) 0.03890(10) 0.0395(4) Uani 1 1 d . . . . .
H40A H 0.072018 0.088790 0.020380 0.059 Uiso 1 1 calc R U . . .
H40B H 0.145674 0.033991 0.094371 0.059 Uiso 1 1 calc R U . . .
H40C H 0.227860 0.004464 0.006985 0.059 Uiso 1 1 calc R U . . .
C41 C 0.18456(15) 0.28859(12) 0.02770(7) 0.0251(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 C41 1.2684(17) . ?
O2 C41 1.2627(16) . ?
O3 H3A 0.847(19) . ?
O3 H3B 0.860(19) . ?
N1 C20 1.4779(16) . ?
N1 C19 1.4892(15) . ?
N1 H1A 0.9100 . ?
N1 H1AB 0.9100 . ?
N2 C41 1.3720(16) . ?
N2 C40 1.4455(18) . ?
N2 C39 1.4515(17) . ?
C1 C2 1.3906(17) . ?
C1 C6 1.4039(17) . ?
C1 C16 1.5273(16) . ?
C2 C3 1.3942(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3836(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3943(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3822(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.5139(17) . ?
C7 C8 1.5114(17) . ?
C7 C14 1.5515(17) . ?
C7 H7 1.0000 . ?
C8 C9 1.3878(17) . ?
C8 C13 1.3992(17) . ?
C9 C10 1.3870(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3951(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3886(17) . ?
C12 H12 0.9500 . ?
C13 C16 1.5324(16) . ?
C14 C15 1.5398(17) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5678(16) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5280(16) . ?
C17 C18 1.5366(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5178(17) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.3875(18) . ?
C21 C26 1.4025(18) . ?
C21 C36 1.5301(18) . ?
C22 C23 1.393(2) . ?
C22 H22 0.9500 . ?
C23 C24 1.385(2) . ?
C23 H23 0.9500 . ?
C24 C25 1.389(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.3870(19) . ?
C25 H25 0.9500 . ?
C26 C27 1.5045(19) . ?
C27 C28 1.5110(19) . ?
C27 C34 1.5531(18) . ?
C27 H27 1.0000 . ?
C28 C29 1.3881(19) . ?
C28 C33 1.4006(18) . ?
C29 C30 1.388(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.382(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.3975(19) . ?
C31 H31 0.9500 . ?
C32 C33 1.3848(18) . ?
C32 H32 0.9500 . ?
C33 C36 1.5312(17) . ?
C34 C35 1.5457(18) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.5717(17) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.5266(17) . ?
C37 C38 1.5359(17) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.5263(17) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 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
H3A O3 H3B 109(4) . . ?
C20 N1 C19 114.54(10) . . ?
C20 N1 H1A 108.6 . . ?
C19 N1 H1A 108.6 . . ?
C20 N1 H1AB 108.6 . . ?
C19 N1 H1AB 108.6 . . ?
H1A N1 H1AB 107.6 . . ?
C41 N2 C40 120.47(12) . . ?
C41 N2 C39 121.96(11) . . ?
C40 N2 C39 117.31(11) . . ?
C2 C1 C6 119.33(11) . . ?
C2 C1 C16 126.87(11) . . ?
C6 C1 C16 113.81(10) . . ?
C1 C2 C3 119.82(12) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.54(12) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.92(12) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 119.81(12) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 120.54(11) . . ?
C5 C6 C7 125.81(11) . . ?
C1 C6 C7 113.64(10) . . ?
C8 C7 C6 106.20(10) . . ?
C8 C7 C14 107.10(10) . . ?
C6 C7 C14 106.82(10) . . ?
C8 C7 H7 112.1 . . ?
C6 C7 H7 112.1 . . ?
C14 C7 H7 112.1 . . ?
C9 C8 C13 120.82(12) . . ?
C9 C8 C7 125.35(11) . . ?
C13 C8 C7 113.81(10) . . ?
C10 C9 C8 119.66(12) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 119.90(12) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 120.49(12) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 119.85(12) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C8 119.23(11) . . ?
C12 C13 C16 126.96(11) . . ?
C8 C13 C16 113.77(10) . . ?
C15 C14 C7 109.45(10) . . ?
C15 C14 H14A 109.8 . . ?
C7 C14 H14A 109.8 . . ?
C15 C14 H14B 109.8 . . ?
C7 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C14 C15 C16 111.36(9) . . ?
C14 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C16 C15 H15B 109.4 . . ?
H15A C15 H15B 108.0 . . ?
C1 C16 C17 113.10(10) . . ?
C1 C16 C13 104.84(9) . . ?
C17 C16 C13 115.06(10) . . ?
C1 C16 C15 105.37(9) . . ?
C17 C16 C15 111.36(9) . . ?
C13 C16 C15 106.35(9) . . ?
C16 C17 C18 115.60(10) . . ?
C16 C17 H17A 108.4 . . ?
C18 C17 H17A 108.4 . . ?
C16 C17 H17B 108.4 . . ?
C18 C17 H17B 108.4 . . ?
H17A C17 H17B 107.4 . . ?
C19 C18 C17 110.48(10) . . ?
C19 C18 H18A 109.6 . . ?
C17 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
N1 C19 C18 113.02(10) . . ?
N1 C19 H19A 109.0 . . ?
C18 C19 H19A 109.0 . . ?
N1 C19 H19B 109.0 . . ?
C18 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 119.26(12) . . ?
C22 C21 C36 127.39(12) . . ?
C26 C21 C36 113.35(11) . . ?
C21 C22 C23 119.92(13) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C24 C23 C22 120.53(14) . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23 C24 C25 119.94(13) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C26 C25 C24 119.76(14) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C21 120.53(13) . . ?
C25 C26 C27 125.49(12) . . ?
C21 C26 C27 113.98(11) . . ?
C26 C27 C28 107.62(10) . . ?
C26 C27 C34 106.68(11) . . ?
C28 C27 C34 106.50(11) . . ?
C26 C27 H27 111.9 . . ?
C28 C27 H27 111.9 . . ?
C34 C27 H27 111.9 . . ?
C29 C28 C33 120.36(13) . . ?
C29 C28 C27 125.89(12) . . ?
C33 C28 C27 113.74(11) . . ?
C30 C29 C28 119.60(13) . . ?
C30 C29 H29 120.2 . . ?
C28 C29 H29 120.2 . . ?
C31 C30 C29 120.32(12) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C32 120.30(13) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C33 C32 C31 119.73(13) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C32 C33 C28 119.66(12) . . ?
C32 C33 C36 126.75(11) . . ?
C28 C33 C36 113.59(11) . . ?
C35 C34 C27 108.80(10) . . ?
C35 C34 H34A 109.9 . . ?
C27 C34 H34A 109.9 . . ?
C35 C34 H34B 109.9 . . ?
C27 C34 H34B 109.9 . . ?
H34A C34 H34B 108.3 . . ?
C34 C35 C36 111.48(10) . . ?
C34 C35 H35A 109.3 . . ?
C36 C35 H35A 109.3 . . ?
C34 C35 H35B 109.3 . . ?
C36 C35 H35B 109.3 . . ?
H35A C35 H35B 108.0 . . ?
C37 C36 C21 114.92(10) . . ?
C37 C36 C33 112.77(10) . . ?
C21 C36 C33 105.63(10) . . ?
C37 C36 C35 111.68(10) . . ?
C21 C36 C35 106.03(10) . . ?
C33 C36 C35 105.05(10) . . ?
C36 C37 C38 115.92(10) . . ?
C36 C37 H37A 108.3 . . ?
C38 C37 H37A 108.3 . . ?
C36 C37 H37B 108.3 . . ?
C38 C37 H37B 108.3 . . ?
H37A C37 H37B 107.4 . . ?
C39 C38 C37 111.09(10) . . ?
C39 C38 H38A 109.4 . . ?
C37 C38 H38A 109.4 . . ?
C39 C38 H38B 109.4 . . ?
C37 C38 H38B 109.4 . . ?
H38A C38 H38B 108.0 . . ?
N2 C39 C38 113.36(11) . . ?
N2 C39 H39A 108.9 . . ?
C38 C39 H39A 108.9 . . ?
N2 C39 H39B 108.9 . . ?
C38 C39 H39B 108.9 . . ?
H39A C39 H39B 107.7 . . ?
N2 C40 H40A 109.5 . . ?
N2 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
N2 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O2 C41 O1 124.21(12) . . ?
O2 C41 N2 117.66(12) . . ?
O1 C41 N2 118.13(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
C6 C1 C2 C3 -2.03(18) . . . . ?
C16 C1 C2 C3 178.17(11) . . . . ?
C1 C2 C3 C4 1.39(19) . . . . ?
C2 C3 C4 C5 0.46(19) . . . . ?
C3 C4 C5 C6 -1.65(19) . . . . ?
C4 C5 C6 C1 1.00(18) . . . . ?
C4 C5 C6 C7 -178.74(12) . . . . ?
C2 C1 C6 C5 0.85(17) . . . . ?
C16 C1 C6 C5 -179.33(11) . . . . ?
C2 C1 C6 C7 -179.39(11) . . . . ?
C16 C1 C6 C7 0.44(14) . . . . ?
C5 C6 C7 C8 124.69(13) . . . . ?
C1 C6 C7 C8 -55.06(13) . . . . ?
C5 C6 C7 C14 -121.25(13) . . . . ?
C1 C6 C7 C14 59.00(13) . . . . ?
C6 C7 C8 C9 -124.52(13) . . . . ?
C14 C7 C8 C9 121.61(13) . . . . ?
C6 C7 C8 C13 53.77(13) . . . . ?
C14 C7 C8 C13 -60.10(13) . . . . ?
C13 C8 C9 C10 -1.09(18) . . . . ?
C7 C8 C9 C10 177.08(12) . . . . ?
C8 C9 C10 C11 -1.07(19) . . . . ?
C9 C10 C11 C12 1.81(19) . . . . ?
C10 C11 C12 C13 -0.38(19) . . . . ?
C11 C12 C13 C8 -1.75(18) . . . . ?
C11 C12 C13 C16 -179.04(11) . . . . ?
C9 C8 C13 C12 2.50(18) . . . . ?
C7 C8 C13 C12 -175.87(11) . . . . ?
C9 C8 C13 C16 -179.87(11) . . . . ?
C7 C8 C13 C16 1.77(14) . . . . ?
C8 C7 C14 C15 56.60(13) . . . . ?
C6 C7 C14 C15 -56.85(13) . . . . ?
C7 C14 C15 C16 0.09(14) . . . . ?
C2 C1 C16 C17 0.03(17) . . . . ?
C6 C1 C16 C17 -179.78(10) . . . . ?
C2 C1 C16 C13 -126.08(12) . . . . ?
C6 C1 C16 C13 54.11(12) . . . . ?
C2 C1 C16 C15 121.90(12) . . . . ?
C6 C1 C16 C15 -57.91(12) . . . . ?
C12 C13 C16 C1 121.92(13) . . . . ?
C8 C13 C16 C1 -55.49(12) . . . . ?
C12 C13 C16 C17 -2.97(17) . . . . ?
C8 C13 C16 C17 179.62(10) . . . . ?
C12 C13 C16 C15 -126.76(12) . . . . ?
C8 C13 C16 C15 55.82(13) . . . . ?
C14 C15 C16 C1 55.86(12) . . . . ?
C14 C15 C16 C17 178.85(10) . . . . ?
C14 C15 C16 C13 -55.08(12) . . . . ?
C1 C16 C17 C18 169.38(10) . . . . ?
C13 C16 C17 C18 -70.17(13) . . . . ?
C15 C16 C17 C18 50.94(14) . . . . ?
C16 C17 C18 C19 170.77(10) . . . . ?
C20 N1 C19 C18 63.04(14) . . . . ?
C17 C18 C19 N1 169.20(10) . . . . ?
C26 C21 C22 C23 2.30(19) . . . . ?
C36 C21 C22 C23 -178.42(12) . . . . ?
C21 C22 C23 C24 0.1(2) . . . . ?
C22 C23 C24 C25 -1.7(2) . . . . ?
C23 C24 C25 C26 0.8(2) . . . . ?
C24 C25 C26 C21 1.6(2) . . . . ?
C24 C25 C26 C27 -177.83(13) . . . . ?
C22 C21 C26 C25 -3.13(18) . . . . ?
C36 C21 C26 C25 177.49(11) . . . . ?
C22 C21 C26 C27 176.33(11) . . . . ?
C36 C21 C26 C27 -3.04(15) . . . . ?
C25 C26 C27 C28 127.31(13) . . . . ?
C21 C26 C27 C28 -52.12(14) . . . . ?
C25 C26 C27 C34 -118.72(14) . . . . ?
C21 C26 C27 C34 61.84(14) . . . . ?
C26 C27 C28 C29 -126.95(13) . . . . ?
C34 C27 C28 C29 118.97(14) . . . . ?
C26 C27 C28 C33 53.95(14) . . . . ?
C34 C27 C28 C33 -60.14(14) . . . . ?
C33 C28 C29 C30 -1.41(19) . . . . ?
C27 C28 C29 C30 179.53(12) . . . . ?
C28 C29 C30 C31 1.3(2) . . . . ?
C29 C30 C31 C32 -0.1(2) . . . . ?
C30 C31 C32 C33 -1.13(19) . . . . ?
C31 C32 C33 C28 1.05(18) . . . . ?
C31 C32 C33 C36 -179.50(12) . . . . ?
C29 C28 C33 C32 0.22(18) . . . . ?
C27 C28 C33 C32 179.38(11) . . . . ?
C29 C28 C33 C36 -179.30(11) . . . . ?
C27 C28 C33 C36 -0.14(15) . . . . ?
C26 C27 C34 C35 -56.93(14) . . . . ?
C28 C27 C34 C35 57.79(14) . . . . ?
C27 C34 C35 C36 -0.58(16) . . . . ?
C22 C21 C36 C37 1.40(18) . . . . ?
C26 C21 C36 C37 -179.29(10) . . . . ?
C22 C21 C36 C33 -123.57(13) . . . . ?
C26 C21 C36 C33 55.74(13) . . . . ?
C22 C21 C36 C35 125.26(13) . . . . ?
C26 C21 C36 C35 -55.42(13) . . . . ?
C32 C33 C36 C37 0.32(17) . . . . ?
C28 C33 C36 C37 179.80(10) . . . . ?
C32 C33 C36 C21 126.62(13) . . . . ?
C28 C33 C36 C21 -53.91(13) . . . . ?
C32 C33 C36 C35 -121.53(13) . . . . ?
C28 C33 C36 C35 57.94(13) . . . . ?
C34 C35 C36 C37 -178.33(11) . . . . ?
C34 C35 C36 C21 55.80(13) . . . . ?
C34 C35 C36 C33 -55.76(14) . . . . ?
C21 C36 C37 C38 68.76(14) . . . . ?
C33 C36 C37 C38 -170.09(11) . . . . ?
C35 C36 C37 C38 -52.05(15) . . . . ?
C36 C37 C38 C39 -171.58(11) . . . . ?
C41 N2 C39 C38 107.54(13) . . . . ?
C40 N2 C39 C38 -66.66(15) . . . . ?
C37 C38 C39 N2 -62.64(14) . . . . ?
C40 N2 C41 O2 -0.18(18) . . . . ?
C39 N2 C41 O2 -174.21(11) . . . . ?
C40 N2 C41 O1 179.21(12) . . . . ?
C39 N2 C41 O1 5.19(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3A O1 0.847(19) 1.92(2) 2.739(2) 162(4) 2_665 yes
O3 H3B O1 0.860(19) 1.98(2) 2.832(3) 168(4) . yes
N1 H1A O2 0.91 1.75 2.6503(14) 171.8 2_565 yes
N1 H1AB O1 0.91 1.80 2.7074(14) 179.8 . yes

_refine_diff_density_max         0.274
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_NortryptileneCarbamate
_database_code_depnum_ccdc_archive 'CCDC 1947402'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2019-08-15 deposited with the CCDC.	2019-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 N O2, C19 H22 N'
_chemical_formula_sum            'C39 H42 N2 O2'
_chemical_formula_weight         570.74

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.8194(6)
_cell_length_b                   27.0609(15)
_cell_length_c                   11.5232(6)
_cell_angle_alpha                90
_cell_angle_beta                 111.9021(18)
_cell_angle_gamma                90
_cell_volume                     3130.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9244
_cell_measurement_theta_min      2.4291
_cell_measurement_theta_max      28.7551

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             1224
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.370
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.074
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6174
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            89404
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.526
_diffrn_reflns_theta_max         28.772
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8095
_reflns_number_gt                7038
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Apex3 v2018.1-0 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev946 (Hübschle et al., 2011)
;
_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)+(0.0353P)²+2.4499P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0070(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8095
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1269
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_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
N1 N 1.04373(13) 0.05123(5) 0.92138(12) 0.0255(3) Uani 1 1 d . . . . .
H1D H 0.959454 0.039288 0.884116 0.031 Uiso 1 1 calc R U . . .
H1E H 1.098054 0.025364 0.957941 0.031 Uiso 1 1 calc R U . . .
C1 C 1.04673(19) 0.08715(7) 1.01909(17) 0.0379(4) Uani 1 1 d . . . . .
H1A H 0.987032 0.114806 0.980540 0.057 Uiso 1 1 calc R U . . .
H1B H 1.137723 0.099543 1.061059 0.057 Uiso 1 1 calc R U . . .
H1C H 1.017407 0.070917 1.080420 0.057 Uiso 1 1 calc R U . . .
C2 C 1.08652(16) 0.07305(6) 0.82463(14) 0.0273(3) Uani 1 1 d . . . . .
H2A H 1.182475 0.081343 0.862047 0.033 Uiso 1 1 calc R U . . .
H2B H 1.036395 0.103968 0.792801 0.033 Uiso 1 1 calc R U . . .
C3 C 1.06224(16) 0.03709(6) 0.71684(14) 0.0278(3) Uani 1 1 d . . . . .
H3A H 1.104103 0.004882 0.749652 0.033 Uiso 1 1 calc R U . . .
H3B H 0.965328 0.031719 0.673194 0.033 Uiso 1 1 calc R U . . .
C4 C 1.11993(15) 0.05733(5) 0.62644(14) 0.0258(3) Uani 1 1 d . . . . .
H4 H 1.207425 0.046957 0.637246 0.031 Uiso 1 1 calc R U . . .
C5 C 1.05987(14) 0.08849(5) 0.53243(14) 0.0224(3) Uani 1 1 d . . . . .
C6 C 1.13485(14) 0.10806(5) 0.45618(13) 0.0230(3) Uani 1 1 d . . . . .
C7 C 1.19625(15) 0.07361(6) 0.40380(14) 0.0271(3) Uani 1 1 d . . . . .
H7 H 1.186109 0.039329 0.415709 0.033 Uiso 1 1 calc R U . . .
C8 C 1.27128(15) 0.08836(7) 0.33518(15) 0.0322(3) Uani 1 1 d . . . . .
H8 H 1.312410 0.064517 0.300826 0.039 Uiso 1 1 calc R U . . .
C9 C 1.28543(16) 0.13835(7) 0.31740(15) 0.0346(4) Uani 1 1 d . . . . .
H9 H 1.336716 0.149007 0.270752 0.041 Uiso 1 1 calc R U . . .
C10 C 1.22509(15) 0.17260(7) 0.36742(16) 0.0321(3) Uani 1 1 d . . . . .
H10 H 1.235956 0.206740 0.354562 0.038 Uiso 1 1 calc R U . . .
C11 C 1.14811(14) 0.15871(6) 0.43671(14) 0.0256(3) Uani 1 1 d . . . . .
C12 C 1.08805(17) 0.20096(6) 0.48457(18) 0.0335(4) Uani 1 1 d . . . . .
H12A H 1.022918 0.217944 0.411052 0.040 Uiso 1 1 calc R U . . .
H12B H 1.160173 0.224886 0.526455 0.040 Uiso 1 1 calc R U . . .
C13 C 1.01847(16) 0.18931(6) 0.57447(16) 0.0300(3) Uani 1 1 d . . . . .
H13A H 1.082803 0.173211 0.650014 0.036 Uiso 1 1 calc R U . . .
H13B H 0.989542 0.220626 0.600914 0.036 Uiso 1 1 calc R U . . .
C14 C 0.89925(15) 0.15612(6) 0.51801(14) 0.0250(3) Uani 1 1 d . . . . .
C15 C 0.76937(16) 0.17365(6) 0.48496(15) 0.0306(3) Uani 1 1 d . . . . .
H15 H 0.754855 0.207660 0.495909 0.037 Uiso 1 1 calc R U . . .
C16 C 0.66077(16) 0.14203(7) 0.43618(16) 0.0337(4) Uani 1 1 d . . . . .
H16 H 0.572903 0.154409 0.414959 0.040 Uiso 1 1 calc R U . . .
C17 C 0.68079(16) 0.09260(7) 0.41862(15) 0.0317(3) Uani 1 1 d . . . . .
H17 H 0.606847 0.070888 0.385838 0.038 Uiso 1 1 calc R U . . .
C18 C 0.81028(15) 0.07469(6) 0.44928(14) 0.0273(3) Uani 1 1 d . . . . .
H18 H 0.823989 0.040818 0.435975 0.033 Uiso 1 1 calc R U . . .
C19 C 0.91981(14) 0.10621(5) 0.49937(13) 0.0228(3) Uani 1 1 d . . . . .
O1 O 0.79567(11) 0.02530(5) 0.79269(12) 0.0354(3) Uani 1 1 d . . . . .
O2 O 0.75282(12) 0.00794(5) 0.96473(11) 0.0377(3) Uani 1 1 d . . . . .
N2 N 0.58170(12) 0.01845(5) 0.77872(12) 0.0266(3) Uani 1 1 d . . . . .
C20 C 0.71724(15) 0.01761(6) 0.84963(15) 0.0278(3) Uani 1 1 d . . . . .
C21 C 0.48770(17) 0.01227(7) 0.84045(17) 0.0342(4) Uani 1 1 d . . . . .
H21A H 0.402783 0.000080 0.780052 0.051 Uiso 1 1 calc R U . . .
H21B H 0.473547 0.044131 0.874012 0.051 Uiso 1 1 calc R U . . .
H21C H 0.523332 -0.011553 0.908949 0.051 Uiso 1 1 calc R U . . .
C22 C 0.53247(15) 0.04294(6) 0.65763(14) 0.0262(3) Uani 1 1 d . . . . .
H22A H 0.450189 0.026127 0.602674 0.031 Uiso 1 1 calc R U . . .
H22B H 0.599630 0.039564 0.618736 0.031 Uiso 1 1 calc R U . . .
C23 C 0.50236(15) 0.09806(6) 0.66554(14) 0.0268(3) Uani 1 1 d . . . . .
H23A H 0.464988 0.112122 0.580126 0.032 Uiso 1 1 calc R U . . .
H23B H 0.434704 0.101694 0.703766 0.032 Uiso 1 1 calc R U . . .
C24 C 0.62549(15) 0.12622(5) 0.74181(14) 0.0247(3) Uani 1 1 d . . . . .
H24 H 0.698670 0.124106 0.715401 0.030 Uiso 1 1 calc R U . . .
C25 C 0.64340(14) 0.15396(5) 0.84288(14) 0.0229(3) Uani 1 1 d . . . . .
C26 C 0.53507(14) 0.16196(5) 0.89217(14) 0.0247(3) Uani 1 1 d . . . . .
C27 C 0.41774(15) 0.18671(6) 0.82171(17) 0.0311(3) Uani 1 1 d . . . . .
H27 H 0.404783 0.198012 0.739938 0.037 Uiso 1 1 calc R U . . .
C28 C 0.31955(17) 0.19493(7) 0.8706(2) 0.0406(4) Uani 1 1 d . . . . .
H28 H 0.240704 0.212327 0.822746 0.049 Uiso 1 1 calc R U . . .
C29 C 0.33661(18) 0.17787(8) 0.9883(2) 0.0441(5) Uani 1 1 d . . . . .
H29 H 0.269288 0.183217 1.021281 0.053 Uiso 1 1 calc R U . . .
C30 C 0.45209(19) 0.15294(7) 1.05826(19) 0.0407(4) Uani 1 1 d . . . . .
H30 H 0.462965 0.140956 1.138983 0.049 Uiso 1 1 calc R U . . .
C31 C 0.55298(16) 0.14510(6) 1.01207(16) 0.0294(3) Uani 1 1 d . . . . .
C32 C 0.68244(17) 0.12093(6) 1.09004(16) 0.0330(3) Uani 1 1 d . . . . .
H32A H 0.705871 0.095676 1.039538 0.040 Uiso 1 1 calc R U . . .
H32B H 0.672694 0.104175 1.162519 0.040 Uiso 1 1 calc R U . . .
C33 C 0.79373(17) 0.15945(7) 1.13642(15) 0.0352(4) Uani 1 1 d . . . . .
H33A H 0.765106 0.185433 1.181507 0.042 Uiso 1 1 calc R U . . .
H33B H 0.873118 0.143230 1.198091 0.042 Uiso 1 1 calc R U . . .
C34 C 0.83615(15) 0.18460(6) 1.03950(14) 0.0265(3) Uani 1 1 d . . . . .
C35 C 0.95317(16) 0.21271(7) 1.08767(17) 0.0343(4) Uani 1 1 d . . . . .
H35 H 0.994230 0.216796 1.175705 0.041 Uiso 1 1 calc R U . . .
C36 C 1.01100(16) 0.23464(7) 1.01269(19) 0.0392(4) Uani 1 1 d . . . . .
H36 H 1.089982 0.253661 1.048642 0.047 Uiso 1 1 calc R U . . .
C37 C 0.95316(17) 0.22872(6) 0.88499(18) 0.0355(4) Uani 1 1 d . . . . .
H37 H 0.993604 0.242710 0.832253 0.043 Uiso 1 1 calc R U . . .
C38 C 0.83520(15) 0.20215(6) 0.83372(15) 0.0278(3) Uani 1 1 d . . . . .
H38 H 0.795128 0.198782 0.745414 0.033 Uiso 1 1 calc R U . . .
C39 C 0.77329(14) 0.18006(5) 0.90866(14) 0.0228(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
N1 C1 1.479(2) . ?
N1 C2 1.4802(19) . ?
N1 H1D 0.9100 . ?
N1 H1E 0.9100 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.522(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.503(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.335(2) . ?
C4 H4 0.9500 . ?
C5 C19 1.497(2) . ?
C5 C6 1.4975(19) . ?
C6 C7 1.405(2) . ?
C6 C11 1.405(2) . ?
C7 C8 1.387(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.403(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.517(2) . ?
C12 C13 1.523(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.506(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.395(2) . ?
C14 C19 1.398(2) . ?
C15 C16 1.391(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.398(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.398(2) . ?
C18 H18 0.9500 . ?
O1 C20 1.269(2) . ?
O2 C20 1.263(2) . ?
N2 C20 1.3873(19) . ?
N2 C21 1.4518(19) . ?
N2 C22 1.4546(19) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.537(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.501(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.338(2) . ?
C24 H24 0.9500 . ?
C25 C26 1.497(2) . ?
C25 C39 1.501(2) . ?
C26 C27 1.397(2) . ?
C26 C31 1.398(2) . ?
C27 C28 1.394(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.378(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.384(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.398(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.503(2) . ?
C32 C33 1.530(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.518(2) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.402(2) . ?
C34 C39 1.409(2) . ?
C35 C36 1.376(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.377(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.390(2) . ?
C37 H37 0.9500 . ?
C38 C39 1.408(2) . ?
C38 H38 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
C1 N1 C2 112.77(13) . . ?
C1 N1 H1D 109.0 . . ?
C2 N1 H1D 109.0 . . ?
C1 N1 H1E 109.0 . . ?
C2 N1 H1E 109.0 . . ?
H1D N1 H1E 107.8 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 110.63(12) . . ?
N1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
C3 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 C3 C2 110.05(12) . . ?
C4 C3 H3A 109.7 . . ?
C2 C3 H3A 109.7 . . ?
C4 C3 H3B 109.7 . . ?
C2 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C5 C4 C3 126.18(14) . . ?
C5 C4 H4 116.9 . . ?
C3 C4 H4 116.9 . . ?
C4 C5 C19 123.31(13) . . ?
C4 C5 C6 119.56(13) . . ?
C19 C5 C6 117.12(12) . . ?
C7 C6 C11 119.08(14) . . ?
C7 C6 C5 117.64(13) . . ?
C11 C6 C5 123.28(13) . . ?
C8 C7 C6 121.68(15) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C9 C8 C7 119.09(15) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C10 C9 C8 119.95(15) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 122.17(16) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C10 C11 C6 118.02(14) . . ?
C10 C11 C12 115.52(14) . . ?
C6 C11 C12 126.45(14) . . ?
C11 C12 C13 118.60(13) . . ?
C11 C12 H12A 107.7 . . ?
C13 C12 H12A 107.7 . . ?
C11 C12 H12B 107.7 . . ?
C13 C12 H12B 107.7 . . ?
H12A C12 H12B 107.1 . . ?
C14 C13 C12 112.99(13) . . ?
C14 C13 H13A 109.0 . . ?
C12 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C15 C14 C19 119.24(14) . . ?
C15 C14 C13 121.90(14) . . ?
C19 C14 C13 118.86(13) . . ?
C16 C15 C14 120.93(15) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 119.97(15) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 119.72(15) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C17 C18 C19 120.53(15) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 119.59(14) . . ?
C18 C19 C5 122.09(13) . . ?
C14 C19 C5 118.32(13) . . ?
C20 N2 C21 119.29(13) . . ?
C20 N2 C22 120.05(13) . . ?
C21 N2 C22 116.72(13) . . ?
O2 C20 O1 125.21(15) . . ?
O2 C20 N2 117.58(14) . . ?
O1 C20 N2 117.18(14) . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 C23 113.29(12) . . ?
N2 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
N2 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C24 C23 C22 111.46(13) . . ?
C24 C23 H23A 109.3 . . ?
C22 C23 H23A 109.3 . . ?
C24 C23 H23B 109.3 . . ?
C22 C23 H23B 109.3 . . ?
H23A C23 H23B 108.0 . . ?
C25 C24 C23 127.10(14) . . ?
C25 C24 H24 116.5 . . ?
C23 C24 H24 116.5 . . ?
C24 C25 C26 122.14(13) . . ?
C24 C25 C39 120.52(13) . . ?
C26 C25 C39 117.30(12) . . ?
C27 C26 C31 119.47(14) . . ?
C27 C26 C25 121.29(14) . . ?
C31 C26 C25 119.23(13) . . ?
C28 C27 C26 120.41(17) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C27 120.12(17) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C30 119.81(16) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C29 C30 C31 121.05(18) . . ?
C29 C30 H30 119.5 . . ?
C31 C30 H30 119.5 . . ?
C30 C31 C26 119.13(16) . . ?
C30 C31 C32 121.64(16) . . ?
C26 C31 C32 119.18(14) . . ?
C31 C32 C33 110.42(14) . . ?
C31 C32 H32A 109.6 . . ?
C33 C32 H32A 109.6 . . ?
C31 C32 H32B 109.6 . . ?
C33 C32 H32B 109.6 . . ?
H32A C32 H32B 108.1 . . ?
C34 C33 C32 117.57(14) . . ?
C34 C33 H33A 107.9 . . ?
C32 C33 H33A 107.9 . . ?
C34 C33 H33B 107.9 . . ?
C32 C33 H33B 107.9 . . ?
H33A C33 H33B 107.2 . . ?
C35 C34 C39 118.36(15) . . ?
C35 C34 C33 115.36(14) . . ?
C39 C34 C33 126.19(14) . . ?
C36 C35 C34 122.72(16) . . ?
C36 C35 H35 118.6 . . ?
C34 C35 H35 118.6 . . ?
C35 C36 C37 119.27(15) . . ?
C35 C36 H36 120.4 . . ?
C37 C36 H36 120.4 . . ?
C36 C37 C38 119.59(16) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C37 C38 C39 122.02(15) . . ?
C37 C38 H38 119.0 . . ?
C39 C38 H38 119.0 . . ?
C38 C39 C34 117.97(14) . . ?
C38 C39 C25 117.38(13) . . ?
C34 C39 C25 124.64(13) . . ?

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
C1 N1 C2 C3 -171.61(13) . . . . ?
N1 C2 C3 C4 -173.70(12) . . . . ?
C2 C3 C4 C5 -85.44(19) . . . . ?
C3 C4 C5 C19 -3.1(2) . . . . ?
C3 C4 C5 C6 175.64(14) . . . . ?
C4 C5 C6 C7 52.94(19) . . . . ?
C19 C5 C6 C7 -128.22(14) . . . . ?
C4 C5 C6 C11 -126.00(16) . . . . ?
C19 C5 C6 C11 52.84(19) . . . . ?
C11 C6 C7 C8 1.1(2) . . . . ?
C5 C6 C7 C8 -177.93(14) . . . . ?
C6 C7 C8 C9 -0.3(2) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?
C8 C9 C10 C11 -0.2(2) . . . . ?
C9 C10 C11 C6 0.9(2) . . . . ?
C9 C10 C11 C12 -179.68(15) . . . . ?
C7 C6 C11 C10 -1.3(2) . . . . ?
C5 C6 C11 C10 177.61(14) . . . . ?
C7 C6 C11 C12 179.34(15) . . . . ?
C5 C6 C11 C12 -1.7(2) . . . . ?
C10 C11 C12 C13 -172.17(15) . . . . ?
C6 C11 C12 C13 7.2(2) . . . . ?
C11 C12 C13 C14 -62.0(2) . . . . ?
C12 C13 C14 C15 -107.93(17) . . . . ?
C12 C13 C14 C19 72.65(18) . . . . ?
C19 C14 C15 C16 1.2(2) . . . . ?
C13 C14 C15 C16 -178.17(15) . . . . ?
C14 C15 C16 C17 -0.7(2) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C16 C17 C18 C19 1.0(2) . . . . ?
C17 C18 C19 C14 -0.4(2) . . . . ?
C17 C18 C19 C5 -179.52(14) . . . . ?
C15 C14 C19 C18 -0.7(2) . . . . ?
C13 C14 C19 C18 178.78(14) . . . . ?
C15 C14 C19 C5 178.45(13) . . . . ?
C13 C14 C19 C5 -2.1(2) . . . . ?
C4 C5 C19 C18 -68.4(2) . . . . ?
C6 C5 C19 C18 112.83(15) . . . . ?
C4 C5 C19 C14 112.55(17) . . . . ?
C6 C5 C19 C14 -66.25(18) . . . . ?
C21 N2 C20 O2 4.9(2) . . . . ?
C22 N2 C20 O2 161.87(14) . . . . ?
C21 N2 C20 O1 -176.99(14) . . . . ?
C22 N2 C20 O1 -20.0(2) . . . . ?
C20 N2 C22 C23 -88.83(17) . . . . ?
C21 N2 C22 C23 68.71(18) . . . . ?
N2 C22 C23 C24 61.93(17) . . . . ?
C22 C23 C24 C25 -123.59(17) . . . . ?
C23 C24 C25 C26 -2.1(2) . . . . ?
C23 C24 C25 C39 -179.76(14) . . . . ?
C24 C25 C26 C27 -63.9(2) . . . . ?
C39 C25 C26 C27 113.80(16) . . . . ?
C24 C25 C26 C31 117.32(17) . . . . ?
C39 C25 C26 C31 -64.98(18) . . . . ?
C31 C26 C27 C28 0.5(2) . . . . ?
C25 C26 C27 C28 -178.29(14) . . . . ?
C26 C27 C28 C29 -1.2(2) . . . . ?
C27 C28 C29 C30 0.6(3) . . . . ?
C28 C29 C30 C31 0.6(3) . . . . ?
C29 C30 C31 C26 -1.3(3) . . . . ?
C29 C30 C31 C32 176.08(17) . . . . ?
C27 C26 C31 C30 0.7(2) . . . . ?
C25 C26 C31 C30 179.52(15) . . . . ?
C27 C26 C31 C32 -176.73(14) . . . . ?
C25 C26 C31 C32 2.1(2) . . . . ?
C30 C31 C32 C33 -104.90(18) . . . . ?
C26 C31 C32 C33 72.48(19) . . . . ?
C31 C32 C33 C34 -66.87(19) . . . . ?
C32 C33 C34 C35 -169.02(15) . . . . ?
C32 C33 C34 C39 7.5(2) . . . . ?
C39 C34 C35 C36 -2.1(2) . . . . ?
C33 C34 C35 C36 174.73(16) . . . . ?
C34 C35 C36 C37 -0.5(3) . . . . ?
C35 C36 C37 C38 2.1(3) . . . . ?
C36 C37 C38 C39 -1.2(2) . . . . ?
C37 C38 C39 C34 -1.4(2) . . . . ?
C37 C38 C39 C25 177.64(14) . . . . ?
C35 C34 C39 C38 3.0(2) . . . . ?
C33 C34 C39 C38 -173.49(15) . . . . ?
C35 C34 C39 C25 -176.02(14) . . . . ?
C33 C34 C39 C25 7.5(2) . . . . ?
C24 C25 C39 C38 40.5(2) . . . . ?
C26 C25 C39 C38 -137.25(14) . . . . ?
C24 C25 C39 C34 -140.53(15) . . . . ?
C26 C25 C39 C34 41.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1D O1 0.91 1.73 2.6316(17) 169.2 . yes
N1 H1E O2 0.91 1.77 2.6413(17) 159.1 3_757 yes

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_DespiramineCarbamate
_database_code_depnum_ccdc_archive 'CCDC 1947401'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2019-08-15 deposited with the CCDC.	2019-10-17 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT110_JD_Despiramine_CO2_0m 
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ...          ? Check 
RESPONSE: The structure is modulated along the c-axis direction with molecules
related by pseudo-translation in clearly shifted positions. Satellite 
diffraction peaks along c are clearly resolved. Refinement in the smaller 
size unit cell leads to excessivly large ADPs for a large fraction of 
atoms. 
;
_vrf_PLAT112_JD_Despiramine_CO2_0m 
;
PROBLEM: ADDSYM Detects New (Pseudo) Symm. Elem       c/2        100 %Fit  
RESPONSE: See response above.
;
_vrf_PLAT113_JD_Despiramine_CO2_0m 
;
PROBLEM: ADDSYM Suggests Possible Pseudo/New  Space Group      P21/c Check 
RESPONSE: See response above.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 N2 O2, C18 H23 N2'
_chemical_formula_sum            'C37 H44 N4 O2'
_chemical_formula_weight         576.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.9559(3)
_cell_length_b                   33.9149(10)
_cell_length_c                   20.7715(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.3341(10)
_cell_angle_gamma                90
_cell_volume                     6257.5(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9806
_cell_measurement_theta_min      4.4609
_cell_measurement_theta_max      72.1090

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_F_000             2480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.595
_shelx_estimated_absorpt_T_min   0.885
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6575
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  
;
Bruker AXS D8 Quest CMOS diffractometer with PhotonII charge-integrating pixel 
array detector (CPAD)
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 7.4074
_diffrn_reflns_number            35000
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.509
_diffrn_reflns_theta_max         72.175
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             11830
_reflns_number_gt                10748
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Apex3 v2017.3-0 (Bruker, 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev946 (Hübschle et al., 2011)
;
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
Ammonium NH2+ H atoms were refined and their N-H bond distances were
restrained to be similar to each other.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²+2.0300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11830
_refine_ls_number_parameters     791
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1092
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_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
N1A N 1.53043(11) 0.42931(3) 0.13122(5) 0.0257(2) Uani 1 1 d . . . . .
N2A N 1.10262(11) 0.46607(3) 0.18846(5) 0.0283(2) Uani 1 1 d D . . . .
H2AA H 1.0687(17) 0.4903(4) 0.1676(7) 0.034 Uiso 1 1 d D U . . .
H2AB H 1.1252(17) 0.4715(5) 0.2336(6) 0.034 Uiso 1 1 d D U . . .
C1A C 1.56565(13) 0.41004(4) 0.19277(6) 0.0257(2) Uani 1 1 d . . . . .
C2A C 1.64388(14) 0.42922(4) 0.24602(6) 0.0293(3) Uani 1 1 d . . . . .
H2A H 1.674558 0.455840 0.242180 0.035 Uiso 1 1 calc R U . . .
C3A C 1.67714(17) 0.40954(4) 0.30470(6) 0.0374(3) Uani 1 1 d . . . . .
H3A H 1.731445 0.422550 0.340870 0.045 Uiso 1 1 calc R U . . .
C4A C 1.63085(18) 0.37084(5) 0.31033(7) 0.0419(3) Uani 1 1 d . . . . .
H4A H 1.654569 0.357174 0.350253 0.050 Uiso 1 1 calc R U . . .
C5A C 1.55008(17) 0.35207(4) 0.25782(7) 0.0373(3) Uani 1 1 d . . . . .
H5A H 1.516955 0.325721 0.262338 0.045 Uiso 1 1 calc R U . . .
C6A C 1.51671(14) 0.37126(4) 0.19848(6) 0.0302(3) Uani 1 1 d . . . . .
C7A C 1.43601(16) 0.35127(4) 0.13963(7) 0.0351(3) Uani 1 1 d . . . . .
H7AA H 1.354252 0.368545 0.119202 0.042 Uiso 1 1 calc R U . . .
H7AB H 1.390164 0.326436 0.152685 0.042 Uiso 1 1 calc R U . . .
C8A C 1.54508(17) 0.34228(4) 0.09087(7) 0.0374(3) Uani 1 1 d . . . . .
H8AA H 1.621661 0.323624 0.111545 0.045 Uiso 1 1 calc R U . . .
H8AB H 1.488268 0.328442 0.053522 0.045 Uiso 1 1 calc R U . . .
C9A C 1.62751(14) 0.37679(4) 0.06447(6) 0.0298(3) Uani 1 1 d . . . . .
C10A C 1.71953(15) 0.36722(5) 0.01731(6) 0.0358(3) Uani 1 1 d . . . . .
H10A H 1.730838 0.340249 0.006577 0.043 Uiso 1 1 calc R U . . .
C11A C 1.79483(15) 0.39530(5) -0.01442(6) 0.0376(3) Uani 1 1 d . . . . .
H11A H 1.856867 0.387611 -0.046080 0.045 Uiso 1 1 calc R U . . .
C12A C 1.77903(14) 0.43458(5) 0.00034(6) 0.0342(3) Uani 1 1 d . . . . .
H12A H 1.827872 0.454256 -0.021945 0.041 Uiso 1 1 calc R U . . .
C13A C 1.69114(13) 0.44518(4) 0.04804(6) 0.0289(3) Uani 1 1 d . . . . .
H13A H 1.681500 0.472268 0.058403 0.035 Uiso 1 1 calc R U . . .
C14A C 1.61627(13) 0.41685(4) 0.08128(6) 0.0256(2) Uani 1 1 d . . . . .
C15A C 1.49394(14) 0.47139(4) 0.13356(6) 0.0276(3) Uani 1 1 d . . . . .
H15A H 1.463192 0.481031 0.088844 0.033 Uiso 1 1 calc R U . . .
H15B H 1.585187 0.486117 0.151632 0.033 Uiso 1 1 calc R U . . .
C16A C 1.36789(14) 0.47976(4) 0.17474(6) 0.0294(3) Uani 1 1 d . . . . .
H16A H 1.408938 0.477982 0.221218 0.035 Uiso 1 1 calc R U . . .
H16B H 1.331085 0.507017 0.166180 0.035 Uiso 1 1 calc R U . . .
C17A C 1.23660(14) 0.45141(4) 0.16111(6) 0.0294(3) Uani 1 1 d . . . . .
H17A H 1.211657 0.447955 0.113630 0.035 Uiso 1 1 calc R U . . .
H17B H 1.265791 0.425363 0.180253 0.035 Uiso 1 1 calc R U . . .
C18A C 0.97748(16) 0.43748(5) 0.17981(8) 0.0422(3) Uani 1 1 d . . . . .
H18A H 0.889009 0.448890 0.196089 0.063 Uiso 1 1 calc R U . . .
H18B H 1.007382 0.413328 0.203989 0.063 Uiso 1 1 calc R U . . .
H18C H 0.952951 0.431221 0.133610 0.063 Uiso 1 1 calc R U . . .
N1B N 0.45083(11) 0.58004(3) 0.36409(5) 0.0250(2) Uani 1 1 d . . . . .
N2B N 0.88803(11) 0.54595(3) 0.31447(5) 0.0293(2) Uani 1 1 d D . . . .
H2BA H 0.9166(17) 0.5216(4) 0.3356(7) 0.035 Uiso 1 1 d D U . . .
H2BB H 0.8759(17) 0.5398(5) 0.2696(6) 0.035 Uiso 1 1 d D U . . .
C1B C 0.40682(13) 0.59859(4) 0.30253(6) 0.0253(2) Uani 1 1 d . . . . .
C2B C 0.32549(14) 0.57840(4) 0.25126(6) 0.0287(3) Uani 1 1 d . . . . .
H2B H 0.299718 0.551518 0.256441 0.034 Uiso 1 1 calc R U . . .
C3B C 0.28181(16) 0.59727(4) 0.19264(6) 0.0367(3) Uani 1 1 d . . . . .
H3B H 0.224918 0.583493 0.157986 0.044 Uiso 1 1 calc R U . . .
C4B C 0.32153(18) 0.63631(5) 0.18486(7) 0.0418(3) Uani 1 1 d . . . . .
H4B H 0.290583 0.649488 0.145025 0.050 Uiso 1 1 calc R U . . .
C5B C 0.40645(17) 0.65613(4) 0.23524(7) 0.0378(3) Uani 1 1 d . . . . .
H5B H 0.435576 0.682671 0.229177 0.045 Uiso 1 1 calc R U . . .
C6B C 0.44967(14) 0.63770(4) 0.29459(6) 0.0299(3) Uani 1 1 d . . . . .
C7B C 0.53483(16) 0.65882(4) 0.35122(7) 0.0348(3) Uani 1 1 d . . . . .
H7BA H 0.575373 0.683901 0.336298 0.042 Uiso 1 1 calc R U . . .
H7BB H 0.620714 0.642394 0.370201 0.042 Uiso 1 1 calc R U . . .
C8B C 0.43225(17) 0.66735(4) 0.40270(7) 0.0377(3) Uani 1 1 d . . . . .
H8BA H 0.490954 0.682602 0.437886 0.045 Uiso 1 1 calc R U . . .
H8BB H 0.349734 0.684616 0.382934 0.045 Uiso 1 1 calc R U . . .
C9B C 0.36175(14) 0.63250(4) 0.43345(6) 0.0304(3) Uani 1 1 d . . . . .
C10B C 0.28052(16) 0.64160(5) 0.48483(7) 0.0381(3) Uani 1 1 d . . . . .
H10B H 0.269287 0.668514 0.495912 0.046 Uiso 1 1 calc R U . . .
C11B C 0.21601(15) 0.61316(5) 0.52010(6) 0.0405(3) Uani 1 1 d . . . . .
H11B H 0.161379 0.620567 0.554509 0.049 Uiso 1 1 calc R U . . .
C12B C 0.23167(15) 0.57401(5) 0.50491(6) 0.0367(3) Uani 1 1 d . . . . .
H12B H 0.190095 0.554121 0.529467 0.044 Uiso 1 1 calc R U . . .
C13B C 0.30872(14) 0.56379(4) 0.45339(6) 0.0303(3) Uani 1 1 d . . . . .
H13B H 0.317677 0.536738 0.442637 0.036 Uiso 1 1 calc R U . . .
C14B C 0.37365(13) 0.59240(4) 0.41682(6) 0.0263(2) Uani 1 1 d . . . . .
C15B C 0.49280(13) 0.53832(4) 0.36203(6) 0.0270(2) Uani 1 1 d . . . . .
H15C H 0.403484 0.522741 0.344240 0.032 Uiso 1 1 calc R U . . .
H15D H 0.525422 0.528964 0.406765 0.032 Uiso 1 1 calc R U . . .
C16B C 0.61887(14) 0.53130(4) 0.32069(6) 0.0283(3) Uani 1 1 d . . . . .
H16C H 0.658413 0.504226 0.328466 0.034 Uiso 1 1 calc R U . . .
H16D H 0.577866 0.533435 0.274250 0.034 Uiso 1 1 calc R U . . .
C17B C 0.74683(13) 0.56061(4) 0.33572(6) 0.0272(3) Uani 1 1 d . . . . .
H17C H 0.718626 0.585887 0.313591 0.033 Uiso 1 1 calc R U . . .
H17D H 0.763298 0.565664 0.383037 0.033 Uiso 1 1 calc R U . . .
C18B C 1.01289(16) 0.57417(5) 0.32998(8) 0.0431(3) Uani 1 1 d . . . . .
H18D H 1.105999 0.562730 0.318037 0.065 Uiso 1 1 calc R U . . .
H18E H 1.025596 0.579893 0.376608 0.065 Uiso 1 1 calc R U . . .
H18F H 0.989962 0.598636 0.305602 0.065 Uiso 1 1 calc R U . . .
N1C N 0.75314(12) 0.67277(3) 0.14226(5) 0.0286(2) Uani 1 1 d . . . . .
N2C N 0.76015(12) 0.54892(3) 0.08392(5) 0.0276(2) Uani 1 1 d . . . . .
O2C O 0.82577(11) 0.52937(3) 0.18776(4) 0.0374(2) Uani 1 1 d . . . . .
C2C C 0.85347(14) 0.67515(4) 0.03733(6) 0.0287(3) Uani 1 1 d . . . . .
H2C H 0.912873 0.652423 0.048952 0.034 Uiso 1 1 calc R U . . .
C3C C 0.85740(15) 0.69260(4) -0.02289(6) 0.0316(3) Uani 1 1 d . . . . .
H3C H 0.917775 0.681524 -0.052704 0.038 Uiso 1 1 calc R U . . .
C4C C 0.77325(15) 0.72616(4) -0.03943(6) 0.0323(3) Uani 1 1 d . . . . .
H4C H 0.777400 0.738518 -0.080206 0.039 Uiso 1 1 calc R U . . .
C5C C 0.68296(14) 0.74165(4) 0.00370(6) 0.0289(3) Uani 1 1 d . . . . .
H5C H 0.625796 0.764766 -0.007819 0.035 Uiso 1 1 calc R U . . .
C6C C 0.67436(13) 0.72392(4) 0.06390(6) 0.0259(2) Uani 1 1 d . . . . .
C7C C 0.57532(14) 0.73930(4) 0.11114(6) 0.0319(3) Uani 1 1 d . . . . .
H7CA H 0.514509 0.717374 0.125517 0.038 Uiso 1 1 calc R U . . .
H7CB H 0.505275 0.759162 0.089328 0.038 Uiso 1 1 calc R U . . .
C8C C 0.66735(16) 0.75803(4) 0.17033(7) 0.0353(3) Uani 1 1 d . . . . .
H8CA H 0.725276 0.780198 0.154877 0.042 Uiso 1 1 calc R U . . .
H8CB H 0.595959 0.769425 0.197915 0.042 Uiso 1 1 calc R U . . .
C9C C 0.77662(15) 0.73196(4) 0.21294(6) 0.0311(3) Uani 1 1 d . . . . .
C10C C 0.84244(16) 0.74867(5) 0.27145(7) 0.0380(3) Uani 1 1 d . . . . .
H10C H 0.813426 0.774566 0.282096 0.046 Uiso 1 1 calc R U . . .
C11C C 0.94803(18) 0.72904(5) 0.31447(7) 0.0432(4) Uani 1 1 d . . . . .
H11C H 0.990779 0.741381 0.353589 0.052 Uiso 1 1 calc R U . . .
C12C C 0.99008(18) 0.69141(5) 0.29970(7) 0.0432(4) Uani 1 1 d . . . . .
H12C H 1.062227 0.677520 0.328687 0.052 Uiso 1 1 calc R U . . .
C13C C 0.92660(16) 0.67381(4) 0.24224(7) 0.0370(3) Uani 1 1 d . . . . .
H13C H 0.957276 0.647966 0.232144 0.044 Uiso 1 1 calc R U . . .
C14C C 0.81851(14) 0.69325(4) 0.19885(6) 0.0298(3) Uani 1 1 d . . . . .
C15C C 0.75281(15) 0.62967(4) 0.14407(6) 0.0305(3) Uani 1 1 d . . . . .
H15E H 0.737208 0.620728 0.188091 0.037 Uiso 1 1 calc R U . . .
H15F H 0.851856 0.619721 0.134913 0.037 Uiso 1 1 calc R U . . .
C16C C 0.62960(14) 0.61263(4) 0.09464(6) 0.0314(3) Uani 1 1 d . . . . .
H16E H 0.531245 0.623758 0.102360 0.038 Uiso 1 1 calc R U . . .
H16F H 0.648345 0.620461 0.050460 0.038 Uiso 1 1 calc R U . . .
C17C C 0.62280(14) 0.56790(4) 0.09851(6) 0.0299(3) Uani 1 1 d . . . . .
H17E H 0.603916 0.560179 0.142717 0.036 Uiso 1 1 calc R U . . .
H17F H 0.537180 0.558332 0.067579 0.036 Uiso 1 1 calc R U . . .
C18C C 0.80082(17) 0.55461(5) 0.01914(6) 0.0370(3) Uani 1 1 d . . . . .
H18G H 0.709321 0.557941 -0.011688 0.056 Uiso 1 1 calc R U . . .
H18H H 0.856671 0.531543 0.006800 0.056 Uiso 1 1 calc R U . . .
H18I H 0.863937 0.578175 0.018561 0.056 Uiso 1 1 calc R U . . .
C19C C 0.86563(14) 0.53431(4) 0.13212(6) 0.0272(3) Uani 1 1 d . . . . .
O1C O 0.99332(10) 0.52566(3) 0.11609(5) 0.0372(2) Uani 1 1 d . . . . .
C1C C 0.76284(13) 0.69078(4) 0.08088(6) 0.0254(2) Uani 1 1 d . . . . .
N1D N 1.21826(12) 0.46102(3) 0.42062(5) 0.0267(2) Uani 1 1 d . . . . .
N2D N 1.24617(12) 0.33694(3) 0.36378(5) 0.0285(2) Uani 1 1 d . . . . .
C1D C 1.17826(15) 0.31802(4) 0.30587(6) 0.0299(3) Uani 1 1 d . . . . .
C2D C 1.06732(17) 0.33841(4) 0.26514(7) 0.0379(3) Uani 1 1 d . . . . .
H2D H 1.036719 0.363756 0.277858 0.046 Uiso 1 1 calc R U . . .
C3D C 1.00079(19) 0.32257(5) 0.20663(7) 0.0450(4) Uani 1 1 d . . . . .
H3D H 0.926425 0.337086 0.179768 0.054 Uiso 1 1 calc R U . . .
C4D C 1.04345(18) 0.28567(5) 0.18787(7) 0.0443(4) Uani 1 1 d . . . . .
H4D H 0.999289 0.274536 0.147962 0.053 Uiso 1 1 calc R U . . .
C5D C 1.15158(17) 0.26510(5) 0.22808(7) 0.0390(3) Uani 1 1 d . . . . .
H5D H 1.180453 0.239708 0.214819 0.047 Uiso 1 1 calc R U . . .
C6D C 1.22044(15) 0.28003(4) 0.28748(6) 0.0314(3) Uani 1 1 d . . . . .
C7D C 1.33307(16) 0.25294(4) 0.32601(7) 0.0360(3) Uani 1 1 d . . . . .
H7DA H 1.404013 0.243456 0.296578 0.043 Uiso 1 1 calc R U . . .
H7DB H 1.277719 0.229645 0.339230 0.043 Uiso 1 1 calc R U . . .
C8D C 1.42537(14) 0.26970(4) 0.38650(7) 0.0318(3) Uani 1 1 d . . . . .
H8DA H 1.496657 0.249375 0.405955 0.038 Uiso 1 1 calc R U . . .
H8DB H 1.484825 0.292463 0.374169 0.038 Uiso 1 1 calc R U . . .
C9D C 1.32713(13) 0.28263(4) 0.43562(6) 0.0266(2) Uani 1 1 d . . . . .
C10D C 1.31778(14) 0.26165(4) 0.49290(6) 0.0313(3) Uani 1 1 d . . . . .
H10D H 1.373180 0.237867 0.500734 0.038 Uiso 1 1 calc R U . . .
C11D C 1.22921(15) 0.27492(4) 0.53843(6) 0.0349(3) Uani 1 1 d . . . . .
H11D H 1.224134 0.260322 0.577133 0.042 Uiso 1 1 calc R U . . .
C12D C 1.14830(15) 0.30944(4) 0.52735(6) 0.0335(3) Uani 1 1 d . . . . .
H12D H 1.090031 0.319091 0.559111 0.040 Uiso 1 1 calc R U . . .
C13D C 1.15202(14) 0.33007(4) 0.46982(6) 0.0298(3) Uani 1 1 d . . . . .
H13D H 1.094557 0.353521 0.462004 0.036 Uiso 1 1 calc R U . . .
C14D C 1.23962(13) 0.31657(4) 0.42342(6) 0.0257(2) Uani 1 1 d . . . . .
C15D C 1.23900(15) 0.38002(4) 0.36554(6) 0.0307(3) Uani 1 1 d . . . . .
H15G H 1.138082 0.388131 0.375286 0.037 Uiso 1 1 calc R U . . .
H15H H 1.252476 0.390555 0.322210 0.037 Uiso 1 1 calc R U . . .
C16D C 1.35831(14) 0.39789(4) 0.41609(7) 0.0309(3) Uani 1 1 d . . . . .
H16G H 1.458474 0.387260 0.409970 0.037 Uiso 1 1 calc R U . . .
H16H H 1.337015 0.390437 0.460095 0.037 Uiso 1 1 calc R U . . .
C17D C 1.36012(14) 0.44272(4) 0.41022(6) 0.0291(3) Uani 1 1 d . . . . .
H17G H 1.441288 0.453377 0.442334 0.035 Uiso 1 1 calc R U . . .
H17H H 1.383708 0.449903 0.366436 0.035 Uiso 1 1 calc R U . . .
C18D C 1.17165(17) 0.45624(5) 0.48436(6) 0.0386(3) Uani 1 1 d . . . . .
H18J H 1.260197 0.457244 0.517337 0.058 Uiso 1 1 calc R U . . .
H18K H 1.121147 0.430740 0.486718 0.058 Uiso 1 1 calc R U . . .
H18L H 1.102063 0.477491 0.492200 0.058 Uiso 1 1 calc R U . . .
C19D C 1.11912(14) 0.47572(4) 0.37033(6) 0.0272(3) Uani 1 1 d . . . . .
O1D O 0.98824(11) 0.48425(3) 0.38315(5) 0.0407(2) Uani 1 1 d . . . . .
O2D O 1.16659(11) 0.48086(3) 0.31637(4) 0.0385(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
N1A C14A 1.4316(15) . ?
N1A C1A 1.4346(16) . ?
N1A C15A 1.4660(16) . ?
N2A C18A 1.4756(18) . ?
N2A C17A 1.4778(15) . ?
N2A H2AA 0.960(13) . ?
N2A H2AB 0.952(13) . ?
C1A C2A 1.3926(17) . ?
C1A C6A 1.3962(18) . ?
C2A C3A 1.3883(19) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.386(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.384(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.392(2) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.5001(18) . ?
C7A C8A 1.5251(19) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A C9A 1.523(2) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A C10A 1.3966(18) . ?
C9A C14A 1.4093(18) . ?
C10A C11A 1.382(2) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.378(2) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.3892(18) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.4027(18) . ?
C13A H13A 0.9500 . ?
C15A C16A 1.5275(16) . ?
C15A H15A 0.9900 . ?
C15A H15B 0.9900 . ?
C16A C17A 1.5173(17) . ?
C16A H16A 0.9900 . ?
C16A H16B 0.9900 . ?
C17A H17A 0.9900 . ?
C17A H17B 0.9900 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
N1B C14B 1.4306(15) . ?
N1B C1B 1.4346(15) . ?
N1B C15B 1.4658(16) . ?
N2B C18B 1.4759(19) . ?
N2B C17B 1.4778(16) . ?
N2B H2BA 0.956(13) . ?
N2B H2BB 0.948(13) . ?
C1B C2B 1.3912(17) . ?
C1B C6B 1.3962(18) . ?
C2B C3B 1.3869(19) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.386(2) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.386(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3924(19) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.4999(18) . ?
C7B C8B 1.524(2) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B C9B 1.519(2) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C9B C10B 1.4005(18) . ?
C9B C14B 1.4106(19) . ?
C10B C11B 1.382(2) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.376(2) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.3893(18) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.4032(18) . ?
C13B H13B 0.9500 . ?
C15B C16B 1.5221(17) . ?
C15B H15C 0.9900 . ?
C15B H15D 0.9900 . ?
C16B C17B 1.5191(17) . ?
C16B H16C 0.9900 . ?
C16B H16D 0.9900 . ?
C17B H17C 0.9900 . ?
C17B H17D 0.9900 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
N1C C14C 1.4253(17) . ?
N1C C1C 1.4263(15) . ?
N1C C15C 1.4621(17) . ?
N2C C19C 1.3779(16) . ?
N2C C18C 1.4510(16) . ?
N2C C17C 1.4542(17) . ?
O2C C19C 1.2637(15) . ?
C2C C3C 1.3884(18) . ?
C2C C1C 1.3947(17) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.384(2) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.3847(19) . ?
C4C H4C 0.9500 . ?
C5C C6C 1.3985(17) . ?
C5C H5C 0.9500 . ?
C6C C1C 1.3945(17) . ?
C6C C7C 1.4980(17) . ?
C7C C8C 1.5282(19) . ?
C7C H7CA 0.9900 . ?
C7C H7CB 0.9900 . ?
C8C C9C 1.5170(19) . ?
C8C H8CA 0.9900 . ?
C8C H8CB 0.9900 . ?
C9C C10C 1.4011(19) . ?
C9C C14C 1.4064(19) . ?
C10C C11C 1.386(2) . ?
C10C H10C 0.9500 . ?
C11C C12C 1.376(2) . ?
C11C H11C 0.9500 . ?
C12C C13C 1.390(2) . ?
C12C H12C 0.9500 . ?
C13C C14C 1.4004(19) . ?
C13C H13C 0.9500 . ?
C15C C16C 1.5221(18) . ?
C15C H15E 0.9900 . ?
C15C H15F 0.9900 . ?
C16C C17C 1.5209(18) . ?
C16C H16E 0.9900 . ?
C16C H16F 0.9900 . ?
C17C H17E 0.9900 . ?
C17C H17F 0.9900 . ?
C18C H18G 0.9800 . ?
C18C H18H 0.9800 . ?
C18C H18I 0.9800 . ?
C19C O1C 1.2656(16) . ?
N1D C19D 1.3753(15) . ?
N1D C18D 1.4473(16) . ?
N1D C17D 1.4547(16) . ?
N2D C14D 1.4263(16) . ?
N2D C1D 1.4288(17) . ?
N2D C15D 1.4632(17) . ?
C1D C2D 1.4022(19) . ?
C1D C6D 1.4092(19) . ?
C2D C3D 1.391(2) . ?
C2D H2D 0.9500 . ?
C3D C4D 1.379(2) . ?
C3D H3D 0.9500 . ?
C4D C5D 1.384(2) . ?
C4D H4D 0.9500 . ?
C5D C6D 1.4016(19) . ?
C5D H5D 0.9500 . ?
C6D C7D 1.515(2) . ?
C7D C8D 1.523(2) . ?
C7D H7DA 0.9900 . ?
C7D H7DB 0.9900 . ?
C8D C9D 1.4954(17) . ?
C8D H8DA 0.9900 . ?
C8D H8DB 0.9900 . ?
C9D C14D 1.3975(17) . ?
C9D C10D 1.3980(18) . ?
C10D C11D 1.385(2) . ?
C10D H10D 0.9500 . ?
C11D C12D 1.381(2) . ?
C11D H11D 0.9500 . ?
C12D C13D 1.3889(19) . ?
C12D H12D 0.9500 . ?
C13D C14D 1.3953(17) . ?
C13D H13D 0.9500 . ?
C15D C16D 1.5248(18) . ?
C15D H15G 0.9900 . ?
C15D H15H 0.9900 . ?
C16D C17D 1.5256(18) . ?
C16D H16G 0.9900 . ?
C16D H16H 0.9900 . ?
C17D H17G 0.9900 . ?
C17D H17H 0.9900 . ?
C18D H18J 0.9800 . ?
C18D H18K 0.9800 . ?
C18D H18L 0.9800 . ?
C19D O2D 1.2605(15) . ?
C19D O1D 1.2683(16) . ?

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
C14A N1A C1A 115.72(10) . . ?
C14A N1A C15A 117.00(10) . . ?
C1A N1A C15A 116.01(9) . . ?
C18A N2A C17A 111.92(11) . . ?
C18A N2A H2AA 108.4(9) . . ?
C17A N2A H2AA 109.9(9) . . ?
C18A N2A H2AB 108.0(9) . . ?
C17A N2A H2AB 111.3(9) . . ?
H2AA N2A H2AB 107.2(13) . . ?
C2A C1A C6A 120.27(12) . . ?
C2A C1A N1A 121.75(11) . . ?
C6A C1A N1A 117.98(11) . . ?
C3A C2A C1A 120.17(13) . . ?
C3A C2A H2A 119.9 . . ?
C1A C2A H2A 119.9 . . ?
C4A C3A C2A 119.77(13) . . ?
C4A C3A H3A 120.1 . . ?
C2A C3A H3A 120.1 . . ?
C5A C4A C3A 120.05(13) . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C4A C5A C6A 120.94(13) . . ?
C4A C5A H5A 119.5 . . ?
C6A C5A H5A 119.5 . . ?
C5A C6A C1A 118.78(12) . . ?
C5A C6A C7A 122.46(12) . . ?
C1A C6A C7A 118.71(12) . . ?
C6A C7A C8A 110.41(11) . . ?
C6A C7A H7AA 109.6 . . ?
C8A C7A H7AA 109.6 . . ?
C6A C7A H7AB 109.6 . . ?
C8A C7A H7AB 109.6 . . ?
H7AA C7A H7AB 108.1 . . ?
C9A C8A C7A 117.81(11) . . ?
C9A C8A H8AA 107.9 . . ?
C7A C8A H8AA 107.9 . . ?
C9A C8A H8AB 107.9 . . ?
C7A C8A H8AB 107.9 . . ?
H8AA C8A H8AB 107.2 . . ?
C10A C9A C14A 117.71(13) . . ?
C10A C9A C8A 115.50(12) . . ?
C14A C9A C8A 126.76(11) . . ?
C11A C10A C9A 122.82(13) . . ?
C11A C10A H10A 118.6 . . ?
C9A C10A H10A 118.6 . . ?
C12A C11A C10A 119.33(12) . . ?
C12A C11A H11A 120.3 . . ?
C10A C11A H11A 120.3 . . ?
C11A C12A C13A 119.49(13) . . ?
C11A C12A H12A 120.3 . . ?
C13A C12A H12A 120.3 . . ?
C12A C13A C14A 121.59(13) . . ?
C12A C13A H13A 119.2 . . ?
C14A C13A H13A 119.2 . . ?
C13A C14A C9A 118.99(11) . . ?
C13A C14A N1A 119.27(11) . . ?
C9A C14A N1A 121.74(11) . . ?
N1A C15A C16A 112.53(10) . . ?
N1A C15A H15A 109.1 . . ?
C16A C15A H15A 109.1 . . ?
N1A C15A H15B 109.1 . . ?
C16A C15A H15B 109.1 . . ?
H15A C15A H15B 107.8 . . ?
C17A C16A C15A 112.85(10) . . ?
C17A C16A H16A 109.0 . . ?
C15A C16A H16A 109.0 . . ?
C17A C16A H16B 109.0 . . ?
C15A C16A H16B 109.0 . . ?
H16A C16A H16B 107.8 . . ?
N2A C17A C16A 111.28(10) . . ?
N2A C17A H17A 109.4 . . ?
C16A C17A H17A 109.4 . . ?
N2A C17A H17B 109.4 . . ?
C16A C17A H17B 109.4 . . ?
H17A C17A H17B 108.0 . . ?
N2A C18A H18A 109.5 . . ?
N2A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
N2A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C14B N1B C1B 116.69(10) . . ?
C14B N1B C15B 117.12(10) . . ?
C1B N1B C15B 116.09(9) . . ?
C18B N2B C17B 111.71(11) . . ?
C18B N2B H2BA 108.1(10) . . ?
C17B N2B H2BA 110.0(9) . . ?
C18B N2B H2BB 110.3(10) . . ?
C17B N2B H2BB 111.9(10) . . ?
H2BA N2B H2BB 104.5(13) . . ?
C2B C1B C6B 120.14(11) . . ?
C2B C1B N1B 121.58(11) . . ?
C6B C1B N1B 118.27(11) . . ?
C3B C2B C1B 120.42(12) . . ?
C3B C2B H2B 119.8 . . ?
C1B C2B H2B 119.8 . . ?
C4B C3B C2B 119.70(13) . . ?
C4B C3B H3B 120.2 . . ?
C2B C3B H3B 120.2 . . ?
C3B C4B C5B 119.96(13) . . ?
C3B C4B H4B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C4B C5B C6B 120.96(13) . . ?
C4B C5B H5B 119.5 . . ?
C6B C5B H5B 119.5 . . ?
C5B C6B C1B 118.78(12) . . ?
C5B C6B C7B 122.42(12) . . ?
C1B C6B C7B 118.75(11) . . ?
C6B C7B C8B 110.44(11) . . ?
C6B C7B H7BA 109.6 . . ?
C8B C7B H7BA 109.6 . . ?
C6B C7B H7BB 109.6 . . ?
C8B C7B H7BB 109.6 . . ?
H7BA C7B H7BB 108.1 . . ?
C9B C8B C7B 117.88(11) . . ?
C9B C8B H8BA 107.8 . . ?
C7B C8B H8BA 107.8 . . ?
C9B C8B H8BB 107.8 . . ?
C7B C8B H8BB 107.8 . . ?
H8BA C8B H8BB 107.2 . . ?
C10B C9B C14B 117.50(13) . . ?
C10B C9B C8B 115.68(12) . . ?
C14B C9B C8B 126.79(11) . . ?
C11B C10B C9B 122.92(14) . . ?
C11B C10B H10B 118.5 . . ?
C9B C10B H10B 118.5 . . ?
C12B C11B C10B 119.35(12) . . ?
C12B C11B H11B 120.3 . . ?
C10B C11B H11B 120.3 . . ?
C11B C12B C13B 119.52(14) . . ?
C11B C12B H12B 120.2 . . ?
C13B C12B H12B 120.2 . . ?
C12B C13B C14B 121.68(13) . . ?
C12B C13B H13B 119.2 . . ?
C14B C13B H13B 119.2 . . ?
C13B C14B C9B 118.99(11) . . ?
C13B C14B N1B 119.07(11) . . ?
C9B C14B N1B 121.94(11) . . ?
N1B C15B C16B 112.26(10) . . ?
N1B C15B H15C 109.2 . . ?
C16B C15B H15C 109.2 . . ?
N1B C15B H15D 109.2 . . ?
C16B C15B H15D 109.2 . . ?
H15C C15B H15D 107.9 . . ?
C17B C16B C15B 112.10(10) . . ?
C17B C16B H16C 109.2 . . ?
C15B C16B H16C 109.2 . . ?
C17B C16B H16D 109.2 . . ?
C15B C16B H16D 109.2 . . ?
H16C C16B H16D 107.9 . . ?
N2B C17B C16B 111.73(10) . . ?
N2B C17B H17C 109.3 . . ?
C16B C17B H17C 109.3 . . ?
N2B C17B H17D 109.3 . . ?
C16B C17B H17D 109.3 . . ?
H17C C17B H17D 107.9 . . ?
N2B C18B H18D 109.5 . . ?
N2B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
N2B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C14C N1C C1C 117.59(10) . . ?
C14C N1C C15C 117.90(10) . . ?
C1C N1C C15C 116.84(10) . . ?
C19C N2C C18C 119.45(11) . . ?
C19C N2C C17C 121.83(10) . . ?
C18C N2C C17C 116.97(10) . . ?
C3C C2C C1C 120.40(12) . . ?
C3C C2C H2C 119.8 . . ?
C1C C2C H2C 119.8 . . ?
C4C C3C C2C 119.91(12) . . ?
C4C C3C H3C 120.0 . . ?
C2C C3C H3C 120.0 . . ?
C3C C4C C5C 119.73(12) . . ?
C3C C4C H4C 120.1 . . ?
C5C C4C H4C 120.1 . . ?
C4C C5C C6C 121.24(12) . . ?
C4C C5C H5C 119.4 . . ?
C6C C5C H5C 119.4 . . ?
C1C C6C C5C 118.58(11) . . ?
C1C C6C C7C 118.67(11) . . ?
C5C C6C C7C 122.74(11) . . ?
C6C C7C C8C 111.60(11) . . ?
C6C C7C H7CA 109.3 . . ?
C8C C7C H7CA 109.3 . . ?
C6C C7C H7CB 109.3 . . ?
C8C C7C H7CB 109.3 . . ?
H7CA C7C H7CB 108.0 . . ?
C9C C8C C7C 117.94(11) . . ?
C9C C8C H8CA 107.8 . . ?
C7C C8C H8CA 107.8 . . ?
C9C C8C H8CB 107.8 . . ?
C7C C8C H8CB 107.8 . . ?
H8CA C8C H8CB 107.2 . . ?
C10C C9C C14C 117.65(13) . . ?
C10C C9C C8C 116.04(12) . . ?
C14C C9C C8C 126.30(12) . . ?
C11C C10C C9C 122.82(14) . . ?
C11C C10C H10C 118.6 . . ?
C9C C10C H10C 118.6 . . ?
C12C C11C C10C 119.04(13) . . ?
C12C C11C H11C 120.5 . . ?
C10C C11C H11C 120.5 . . ?
C11C C12C C13C 119.75(14) . . ?
C11C C12C H12C 120.1 . . ?
C13C C12C H12C 120.1 . . ?
C12C C13C C14C 121.60(14) . . ?
C12C C13C H13C 119.2 . . ?
C14C C13C H13C 119.2 . . ?
C13C C14C C9C 119.11(12) . . ?
C13C C14C N1C 118.61(12) . . ?
C9C C14C N1C 122.28(11) . . ?
N1C C15C C16C 111.46(10) . . ?
N1C C15C H15E 109.3 . . ?
C16C C15C H15E 109.3 . . ?
N1C C15C H15F 109.3 . . ?
C16C C15C H15F 109.3 . . ?
H15E C15C H15F 108.0 . . ?
C17C C16C C15C 111.94(10) . . ?
C17C C16C H16E 109.2 . . ?
C15C C16C H16E 109.2 . . ?
C17C C16C H16F 109.2 . . ?
C15C C16C H16F 109.2 . . ?
H16E C16C H16F 107.9 . . ?
N2C C17C C16C 112.95(10) . . ?
N2C C17C H17E 109.0 . . ?
C16C C17C H17E 109.0 . . ?
N2C C17C H17F 109.0 . . ?
C16C C17C H17F 109.0 . . ?
H17E C17C H17F 107.8 . . ?
N2C C18C H18G 109.5 . . ?
N2C C18C H18H 109.5 . . ?
H18G C18C H18H 109.5 . . ?
N2C C18C H18I 109.5 . . ?
H18G C18C H18I 109.5 . . ?
H18H C18C H18I 109.5 . . ?
O2C C19C O1C 125.45(11) . . ?
O2C C19C N2C 117.70(11) . . ?
O1C C19C N2C 116.80(11) . . ?
C6C C1C C2C 120.08(11) . . ?
C6C C1C N1C 118.28(11) . . ?
C2C C1C N1C 121.60(11) . . ?
C19D N1D C18D 120.13(11) . . ?
C19D N1D C17D 122.22(10) . . ?
C18D N1D C17D 116.58(10) . . ?
C14D N2D C1D 116.97(10) . . ?
C14D N2D C15D 117.07(10) . . ?
C1D N2D C15D 117.01(10) . . ?
C2D C1D C6D 118.76(12) . . ?
C2D C1D N2D 118.63(12) . . ?
C6D C1D N2D 122.60(12) . . ?
C3D C2D C1D 121.88(15) . . ?
C3D C2D H2D 119.1 . . ?
C1D C2D H2D 119.1 . . ?
C4D C3D C2D 119.60(15) . . ?
C4D C3D H3D 120.2 . . ?
C2D C3D H3D 120.2 . . ?
C3D C4D C5D 118.99(13) . . ?
C3D C4D H4D 120.5 . . ?
C5D C4D H4D 120.5 . . ?
C4D C5D C6D 122.99(14) . . ?
C4D C5D H5D 118.5 . . ?
C6D C5D H5D 118.5 . . ?
C5D C6D C1D 117.77(13) . . ?
C5D C6D C7D 115.75(13) . . ?
C1D C6D C7D 126.48(12) . . ?
C6D C7D C8D 117.65(11) . . ?
C6D C7D H7DA 107.9 . . ?
C8D C7D H7DA 107.9 . . ?
C6D C7D H7DB 107.9 . . ?
C8D C7D H7DB 107.9 . . ?
H7DA C7D H7DB 107.2 . . ?
C9D C8D C7D 111.57(11) . . ?
C9D C8D H8DA 109.3 . . ?
C7D C8D H8DA 109.3 . . ?
C9D C8D H8DB 109.3 . . ?
C7D C8D H8DB 109.3 . . ?
H8DA C8D H8DB 108.0 . . ?
C14D C9D C10D 118.71(11) . . ?
C14D C9D C8D 118.88(11) . . ?
C10D C9D C8D 122.40(12) . . ?
C11D C10D C9D 121.18(12) . . ?
C11D C10D H10D 119.4 . . ?
C9D C10D H10D 119.4 . . ?
C12D C11D C10D 119.73(12) . . ?
C12D C11D H11D 120.1 . . ?
C10D C11D H11D 120.1 . . ?
C11D C12D C13D 120.06(12) . . ?
C11D C12D H12D 120.0 . . ?
C13D C12D H12D 120.0 . . ?
C12D C13D C14D 120.42(12) . . ?
C12D C13D H13D 119.8 . . ?
C14D C13D H13D 119.8 . . ?
C13D C14D C9D 119.79(11) . . ?
C13D C14D N2D 122.01(11) . . ?
C9D C14D N2D 118.18(11) . . ?
N2D C15D C16D 112.64(10) . . ?
N2D C15D H15G 109.1 . . ?
C16D C15D H15G 109.1 . . ?
N2D C15D H15H 109.1 . . ?
C16D C15D H15H 109.1 . . ?
H15G C15D H15H 107.8 . . ?
C15D C16D C17D 110.78(10) . . ?
C15D C16D H16G 109.5 . . ?
C17D C16D H16G 109.5 . . ?
C15D C16D H16H 109.5 . . ?
C17D C16D H16H 109.5 . . ?
H16G C16D H16H 108.1 . . ?
N1D C17D C16D 113.25(10) . . ?
N1D C17D H17G 108.9 . . ?
C16D C17D H17G 108.9 . . ?
N1D C17D H17H 108.9 . . ?
C16D C17D H17H 108.9 . . ?
H17G C17D H17H 107.7 . . ?
N1D C18D H18J 109.5 . . ?
N1D C18D H18K 109.5 . . ?
H18J C18D H18K 109.5 . . ?
N1D C18D H18L 109.5 . . ?
H18J C18D H18L 109.5 . . ?
H18K C18D H18L 109.5 . . ?
O2D C19D O1D 125.51(11) . . ?
O2D C19D N1D 117.86(11) . . ?
O1D C19D N1D 116.58(11) . . ?

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
C14A N1A C1A C2A 106.91(13) . . . . ?
C15A N1A C1A C2A -35.80(15) . . . . ?
C14A N1A C1A C6A -74.19(14) . . . . ?
C15A N1A C1A C6A 143.09(11) . . . . ?
C6A C1A C2A C3A 1.69(18) . . . . ?
N1A C1A C2A C3A -179.44(11) . . . . ?
C1A C2A C3A C4A -0.7(2) . . . . ?
C2A C3A C4A C5A -0.8(2) . . . . ?
C3A C4A C5A C6A 1.3(2) . . . . ?
C4A C5A C6A C1A -0.3(2) . . . . ?
C4A C5A C6A C7A 176.97(13) . . . . ?
C2A C1A C6A C5A -1.19(18) . . . . ?
N1A C1A C6A C5A 179.89(11) . . . . ?
C2A C1A C6A C7A -178.57(11) . . . . ?
N1A C1A C6A C7A 2.52(17) . . . . ?
C5A C6A C7A C8A -106.46(15) . . . . ?
C1A C6A C7A C8A 70.81(16) . . . . ?
C6A C7A C8A C9A -59.40(17) . . . . ?
C7A C8A C9A C10A -176.56(12) . . . . ?
C7A C8A C9A C14A 1.3(2) . . . . ?
C14A C9A C10A C11A -2.11(19) . . . . ?
C8A C9A C10A C11A 175.95(13) . . . . ?
C9A C10A C11A C12A -0.3(2) . . . . ?
C10A C11A C12A C13A 1.76(19) . . . . ?
C11A C12A C13A C14A -0.72(19) . . . . ?
C12A C13A C14A C9A -1.75(18) . . . . ?
C12A C13A C14A N1A 178.33(11) . . . . ?
C10A C9A C14A C13A 3.07(17) . . . . ?
C8A C9A C14A C13A -174.74(12) . . . . ?
C10A C9A C14A N1A -177.01(11) . . . . ?
C8A C9A C14A N1A 5.18(19) . . . . ?
C1A N1A C14A C13A -127.09(12) . . . . ?
C15A N1A C14A C13A 15.25(15) . . . . ?
C1A N1A C14A C9A 53.00(15) . . . . ?
C15A N1A C14A C9A -164.67(11) . . . . ?
C14A N1A C15A C16A 163.81(10) . . . . ?
C1A N1A C15A C16A -53.97(14) . . . . ?
N1A C15A C16A C17A -45.09(15) . . . . ?
C18A N2A C17A C16A -175.81(11) . . . . ?
C15A C16A C17A N2A -165.47(10) . . . . ?
C14B N1B C1B C2B -108.23(13) . . . . ?
C15B N1B C1B C2B 36.30(15) . . . . ?
C14B N1B C1B C6B 72.72(14) . . . . ?
C15B N1B C1B C6B -142.75(11) . . . . ?
C6B C1B C2B C3B -2.24(18) . . . . ?
N1B C1B C2B C3B 178.73(11) . . . . ?
C1B C2B C3B C4B 1.0(2) . . . . ?
C2B C3B C4B C5B 1.0(2) . . . . ?
C3B C4B C5B C6B -1.7(2) . . . . ?
C4B C5B C6B C1B 0.4(2) . . . . ?
C4B C5B C6B C7B -176.85(13) . . . . ?
C2B C1B C6B C5B 1.50(18) . . . . ?
N1B C1B C6B C5B -179.44(11) . . . . ?
C2B C1B C6B C7B 178.90(11) . . . . ?
N1B C1B C6B C7B -2.04(17) . . . . ?
C5B C6B C7B C8B 106.49(15) . . . . ?
C1B C6B C7B C8B -70.81(16) . . . . ?
C6B C7B C8B C9B 60.94(16) . . . . ?
C7B C8B C9B C10B 173.98(12) . . . . ?
C7B C8B C9B C14B -4.0(2) . . . . ?
C14B C9B C10B C11B 1.57(19) . . . . ?
C8B C9B C10B C11B -176.63(13) . . . . ?
C9B C10B C11B C12B 0.3(2) . . . . ?
C10B C11B C12B C13B -1.61(19) . . . . ?
C11B C12B C13B C14B 1.09(19) . . . . ?
C12B C13B C14B C9B 0.79(18) . . . . ?
C12B C13B C14B N1B -179.64(11) . . . . ?
C10B C9B C14B C13B -2.05(17) . . . . ?
C8B C9B C14B C13B 175.92(12) . . . . ?
C10B C9B C14B N1B 178.39(11) . . . . ?
C8B C9B C14B N1B -3.64(19) . . . . ?
C1B N1B C14B C13B 128.10(12) . . . . ?
C15B N1B C14B C13B -16.05(15) . . . . ?
C1B N1B C14B C9B -52.34(15) . . . . ?
C15B N1B C14B C9B 163.50(11) . . . . ?
C14B N1B C15B C16B -159.37(10) . . . . ?
C1B N1B C15B C16B 56.26(13) . . . . ?
N1B C15B C16B C17B 46.47(14) . . . . ?
C18B N2B C17B C16B -179.13(11) . . . . ?
C15B C16B C17B N2B 159.58(10) . . . . ?
C1C C2C C3C C4C 1.27(19) . . . . ?
C2C C3C C4C C5C -1.40(19) . . . . ?
C3C C4C C5C C6C -0.29(19) . . . . ?
C4C C5C C6C C1C 2.09(18) . . . . ?
C4C C5C C6C C7C -178.57(12) . . . . ?
C1C C6C C7C C8C 70.24(15) . . . . ?
C5C C6C C7C C8C -109.09(14) . . . . ?
C6C C7C C8C C9C -62.05(15) . . . . ?
C7C C8C C9C C10C -171.13(12) . . . . ?
C7C C8C C9C C14C 9.64(19) . . . . ?
C14C C9C C10C C11C 1.47(19) . . . . ?
C8C C9C C10C C11C -177.83(13) . . . . ?
C9C C10C C11C C12C -0.4(2) . . . . ?
C10C C11C C12C C13C 0.1(2) . . . . ?
C11C C12C C13C C14C -0.9(2) . . . . ?
C12C C13C C14C C9C 1.9(2) . . . . ?
C12C C13C C14C N1C -177.19(12) . . . . ?
C10C C9C C14C C13C -2.16(18) . . . . ?
C8C C9C C14C C13C 177.07(12) . . . . ?
C10C C9C C14C N1C 176.91(11) . . . . ?
C8C C9C C14C N1C -3.9(2) . . . . ?
C1C N1C C14C C13C -124.35(13) . . . . ?
C15C N1C C14C C13C 24.20(17) . . . . ?
C1C N1C C14C C9C 56.57(16) . . . . ?
C15C N1C C14C C9C -154.87(12) . . . . ?
C14C N1C C15C C16C 156.87(11) . . . . ?
C1C N1C C15C C16C -54.34(14) . . . . ?
N1C C15C C16C C17C -176.99(10) . . . . ?
C19C N2C C17C C16C 102.02(13) . . . . ?
C18C N2C C17C C16C -62.81(15) . . . . ?
C15C C16C C17C N2C -62.33(14) . . . . ?
C18C N2C C19C O2C -179.29(12) . . . . ?
C17C N2C C19C O2C 16.24(18) . . . . ?
C18C N2C C19C O1C -1.72(18) . . . . ?
C17C N2C C19C O1C -166.19(11) . . . . ?
C5C C6C C1C C2C -2.21(18) . . . . ?
C7C C6C C1C C2C 178.43(11) . . . . ?
C5C C6C C1C N1C -179.81(11) . . . . ?
C7C C6C C1C N1C 0.83(17) . . . . ?
C3C C2C C1C C6C 0.57(19) . . . . ?
C3C C2C C1C N1C 178.09(11) . . . . ?
C14C N1C C1C C6C -71.84(15) . . . . ?
C15C N1C C1C C6C 139.27(12) . . . . ?
C14C N1C C1C C2C 110.60(14) . . . . ?
C15C N1C C1C C2C -38.29(16) . . . . ?
C14D N2D C1D C2D 124.32(13) . . . . ?
C15D N2D C1D C2D -22.04(17) . . . . ?
C14D N2D C1D C6D -56.94(16) . . . . ?
C15D N2D C1D C6D 156.70(12) . . . . ?
C6D C1D C2D C3D -1.6(2) . . . . ?
N2D C1D C2D C3D 177.23(13) . . . . ?
C1D C2D C3D C4D 0.5(2) . . . . ?
C2D C3D C4D C5D 0.3(2) . . . . ?
C3D C4D C5D C6D 0.1(2) . . . . ?
C4D C5D C6D C1D -1.11(19) . . . . ?
C4D C5D C6D C7D 178.30(13) . . . . ?
C2D C1D C6D C5D 1.81(18) . . . . ?
N2D C1D C6D C5D -176.93(11) . . . . ?
C2D C1D C6D C7D -177.52(12) . . . . ?
N2D C1D C6D C7D 3.7(2) . . . . ?
C5D C6D C7D C8D 172.38(11) . . . . ?
C1D C6D C7D C8D -8.28(19) . . . . ?
C6D C7D C8D C9D 61.11(15) . . . . ?
C7D C8D C9D C14D -71.94(15) . . . . ?
C7D C8D C9D C10D 107.04(14) . . . . ?
C14D C9D C10D C11D -2.91(19) . . . . ?
C8D C9D C10D C11D 178.11(12) . . . . ?
C9D C10D C11D C12D 0.0(2) . . . . ?
C10D C11D C12D C13D 2.1(2) . . . . ?
C11D C12D C13D C14D -1.29(19) . . . . ?
C12D C13D C14D C9D -1.62(19) . . . . ?
C12D C13D C14D N2D 179.95(12) . . . . ?
C10D C9D C14D C13D 3.66(18) . . . . ?
C8D C9D C14D C13D -177.32(11) . . . . ?
C10D C9D C14D N2D -177.85(11) . . . . ?
C8D C9D C14D N2D 1.17(17) . . . . ?
C1D N2D C14D C13D -111.09(14) . . . . ?
C15D N2D C14D C13D 35.25(16) . . . . ?
C1D N2D C14D C9D 70.45(15) . . . . ?
C15D N2D C14D C9D -143.20(11) . . . . ?
C14D N2D C15D C16D 54.44(15) . . . . ?
C1D N2D C15D C16D -159.24(11) . . . . ?
N2D C15D C16D C17D 172.59(10) . . . . ?
C19D N1D C17D C16D -104.84(13) . . . . ?
C18D N1D C17D C16D 63.34(15) . . . . ?
C15D C16D C17D N1D 60.97(14) . . . . ?
C18D N1D C19D O2D 177.18(12) . . . . ?
C17D N1D C19D O2D -15.05(18) . . . . ?
C18D N1D C19D O1D -0.43(18) . . . . ?
C17D N1D C19D O1D 167.33(12) . . . . ?

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_BetahistidineCarbamicAcid
_database_code_depnum_ccdc_archive 'CCDC 1947400'
loop_
_audit_author_name
_audit_author_address
'Matthias Zeller'
;Purdue University
United States of America
;
_audit_update_record             
;
2019-08-15 deposited with the CCDC.	2019-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H12 N2 O2'
_chemical_formula_weight         180.21

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   11.1385(7)
_cell_length_b                   11.1376(6)
_cell_length_c                   14.7537(9)
_cell_angle_alpha                90.660(2)
_cell_angle_beta                 90.947(2)
_cell_angle_gamma                90.281(2)
_cell_volume                     1829.89(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9135
_cell_measurement_theta_min      2.2732
_cell_measurement_theta_max      33.1908

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.530
_exptl_crystal_size_mid          0.480
_exptl_crystal_size_min          0.370
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6826
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_measurement_device_type  'Bruker AXS D8 Quest CMOS diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            37070
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.273
_diffrn_reflns_theta_max         33.235
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             13618
_reflns_number_gt                10357
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'Apex3 v2018.1-0 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2016)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  
;  
SHELXL-2018/3 (Sheldrick, 2015, 2018), 
SHELXLE Rev946 (Hübschle et al., 2011)
;
_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)+(0.0619P)²+0.6236P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13618
_refine_ls_number_parameters     477
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1273
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_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
O1A O 0.18018(8) 0.47333(7) 0.39434(7) 0.02849(19) Uani 1 1 d . . . . .
O2A O 0.28894(7) 0.63703(7) 0.35790(6) 0.02461(17) Uani 1 1 d . . . . .
H2AA H 0.345936 0.588000 0.360340 0.037 Uiso 1 1 calc R U . . .
N1A N -0.02334(8) 1.02043(8) 0.36364(6) 0.01959(17) Uani 1 1 d . . . . .
N2A N 0.08770(9) 0.64948(8) 0.36190(7) 0.02314(19) Uani 1 1 d . . . . .
C1A C -0.04001(11) 1.13573(10) 0.34121(8) 0.0223(2) Uani 1 1 d . . . . .
H1A H -0.115701 1.158377 0.316400 0.027 Uiso 1 1 calc R U . . .
C2A C 0.04795(12) 1.22320(10) 0.35254(8) 0.0259(2) Uani 1 1 d . . . . .
H2A H 0.033125 1.303934 0.335726 0.031 Uiso 1 1 calc R U . . .
C3A C 0.15798(11) 1.18999(11) 0.38899(9) 0.0271(2) Uani 1 1 d . . . . .
H3A H 0.220009 1.247912 0.398232 0.032 Uiso 1 1 calc R U . . .
C4A C 0.17647(10) 1.07081(10) 0.41188(8) 0.0235(2) Uani 1 1 d . . . . .
H4A H 0.251757 1.046087 0.436220 0.028 Uiso 1 1 calc R U . . .
C5A C 0.08352(9) 0.98777(9) 0.39880(7) 0.01816(18) Uani 1 1 d . . . . .
C6A C 0.09619(11) 0.85761(10) 0.42289(8) 0.0218(2) Uani 1 1 d . . . . .
H6AA H 0.029509 0.834233 0.462678 0.026 Uiso 1 1 calc R U . . .
H6AB H 0.172468 0.846342 0.457067 0.026 Uiso 1 1 calc R U . . .
C7A C 0.09500(11) 0.77602(10) 0.33865(8) 0.0216(2) Uani 1 1 d . . . . .
H7AA H 0.025456 0.796812 0.299334 0.026 Uiso 1 1 calc R U . . .
H7AB H 0.168962 0.790240 0.303963 0.026 Uiso 1 1 calc R U . . .
C8A C -0.02958(11) 0.59999(12) 0.38336(10) 0.0308(3) Uani 1 1 d . . . . .
H8AA H -0.092011 0.658436 0.368145 0.046 Uiso 1 1 calc R U . . .
H8AB H -0.032189 0.582313 0.448219 0.046 Uiso 1 1 calc R U . . .
H8AC H -0.043449 0.525913 0.348167 0.046 Uiso 1 1 calc R U . . .
C9A C 0.18560(10) 0.57959(9) 0.37300(8) 0.02029(19) Uani 1 1 d . . . . .
O1B O 0.68228(8) 1.02933(7) 0.39466(7) 0.02700(18) Uani 1 1 d . . . . .
O2B O 0.78970(7) 0.86888(7) 0.34978(6) 0.02512(17) Uani 1 1 d . . . . .
H2BA H 0.847149 0.917562 0.356117 0.038 Uiso 1 1 calc R U . . .
N1B N 0.47131(8) 0.48099(8) 0.35936(7) 0.02099(18) Uani 1 1 d . . . . .
N2B N 0.59124(9) 0.84801(8) 0.37216(7) 0.02189(18) Uani 1 1 d . . . . .
C1B C 0.45227(11) 0.36774(10) 0.33006(9) 0.0254(2) Uani 1 1 d . . . . .
H1B H 0.377024 0.348276 0.302257 0.031 Uiso 1 1 calc R U . . .
C2B C 0.53702(12) 0.27831(10) 0.33847(9) 0.0284(2) Uani 1 1 d . . . . .
H2B H 0.520475 0.199060 0.317097 0.034 Uiso 1 1 calc R U . . .
C3B C 0.64661(12) 0.30697(11) 0.37881(9) 0.0295(3) Uani 1 1 d . . . . .
H3B H 0.706313 0.247148 0.386438 0.035 Uiso 1 1 calc R U . . .
C4B C 0.66837(11) 0.42407(11) 0.40801(9) 0.0251(2) Uani 1 1 d . . . . .
H4B H 0.743760 0.445772 0.434619 0.030 Uiso 1 1 calc R U . . .
C5B C 0.57822(10) 0.50943(9) 0.39781(7) 0.01896(18) Uani 1 1 d . . . . .
C6B C 0.59407(11) 0.63795(10) 0.42834(8) 0.0217(2) Uani 1 1 d . . . . .
H6BA H 0.670017 0.646513 0.463676 0.026 Uiso 1 1 calc R U . . .
H6BB H 0.527140 0.660945 0.468204 0.026 Uiso 1 1 calc R U . . .
C7B C 0.59667(10) 0.72162(9) 0.34649(8) 0.0209(2) Uani 1 1 d . . . . .
H7BA H 0.671233 0.707138 0.312526 0.025 Uiso 1 1 calc R U . . .
H7BB H 0.527812 0.702007 0.305581 0.025 Uiso 1 1 calc R U . . .
C8B C 0.47526(11) 0.89497(11) 0.39923(10) 0.0289(2) Uani 1 1 d . . . . .
H8BA H 0.468594 0.979015 0.380929 0.043 Uiso 1 1 calc R U . . .
H8BB H 0.468206 0.889828 0.465199 0.043 Uiso 1 1 calc R U . . .
H8BC H 0.410919 0.847682 0.369791 0.043 Uiso 1 1 calc R U . . .
C9B C 0.68776(10) 0.92248(9) 0.37346(7) 0.01925(19) Uani 1 1 d . . . . .
O1C O 0.47509(7) 0.68440(8) 0.10334(7) 0.02987(19) Uani 1 1 d . . . . .
O2C O 0.63950(7) 0.79631(8) 0.13629(6) 0.02480(17) Uani 1 1 d . . . . .
H2CA H 0.589661 0.852623 0.134417 0.037 Uiso 1 1 calc R U . . .
N1C N 1.02400(8) 0.48163(9) 0.13964(7) 0.02090(18) Uani 1 1 d . . . . .
N2C N 0.65503(8) 0.59551(9) 0.13005(7) 0.02247(18) Uani 1 1 d . . . . .
C1C C 1.13896(10) 0.46554(11) 0.16511(8) 0.0236(2) Uani 1 1 d . . . . .
H1C H 1.160358 0.392534 0.193714 0.028 Uiso 1 1 calc R U . . .
C2C C 1.22781(10) 0.55056(12) 0.15156(8) 0.0261(2) Uani 1 1 d . . . . .
H2C H 1.308634 0.535649 0.169471 0.031 Uiso 1 1 calc R U . . .
C3C C 1.19614(10) 0.65781(12) 0.11132(9) 0.0265(2) Uani 1 1 d . . . . .
H3C H 1.254979 0.718004 0.101207 0.032 Uiso 1 1 calc R U . . .
C4C C 1.07707(10) 0.67605(11) 0.08597(8) 0.0233(2) Uani 1 1 d . . . . .
H4C H 1.053194 0.749528 0.059208 0.028 Uiso 1 1 calc R U . . .
C5C C 0.99300(9) 0.58549(10) 0.10019(7) 0.01867(18) Uani 1 1 d . . . . .
C6C C 0.86313(9) 0.59764(11) 0.07249(8) 0.0222(2) Uani 1 1 d . . . . .
H6CA H 0.838924 0.527757 0.034216 0.027 Uiso 1 1 calc R U . . .
H6CB H 0.852957 0.670935 0.035874 0.027 Uiso 1 1 calc R U . . .
C7C C 0.78176(9) 0.60496(11) 0.15491(8) 0.0214(2) Uani 1 1 d . . . . .
H7CA H 0.802702 0.539485 0.197050 0.026 Uiso 1 1 calc R U . . .
H7CB H 0.796343 0.682255 0.187125 0.026 Uiso 1 1 calc R U . . .
C8C C 0.60598(11) 0.47571(11) 0.11341(10) 0.0310(3) Uani 1 1 d . . . . .
H8CA H 0.636466 0.443923 0.056053 0.047 Uiso 1 1 calc R U . . .
H8CB H 0.518153 0.479735 0.109971 0.047 Uiso 1 1 calc R U . . .
H8CC H 0.630307 0.422826 0.162990 0.047 Uiso 1 1 calc R U . . .
C9C C 0.58269(9) 0.69209(10) 0.12177(8) 0.01992(19) Uani 1 1 d . . . . .
O1D O 0.87303(7) 0.29486(8) 0.14989(7) 0.02579(17) Uani 1 1 d . . . . .
H1DA H 0.921324 0.352403 0.144514 0.039 Uiso 1 1 calc R U . . .
O2D O 1.03312(7) 0.18712(8) 0.10596(7) 0.02810(18) Uani 1 1 d . . . . .
N1D N 0.48505(8) -0.02091(9) 0.13908(7) 0.02286(18) Uani 1 1 d . . . . .
N2D N 0.85390(8) 0.09528(9) 0.13068(7) 0.02317(19) Uani 1 1 d . . . . .
C1D C 0.37267(11) -0.03822(13) 0.16757(9) 0.0291(2) Uani 1 1 d . . . . .
H1D H 0.352691 -0.113328 0.193373 0.035 Uiso 1 1 calc R U . . .
C2D C 0.28457(11) 0.04845(14) 0.16106(10) 0.0333(3) Uani 1 1 d . . . . .
H2D H 0.205871 0.033554 0.182262 0.040 Uiso 1 1 calc R U . . .
C3D C 0.31393(11) 0.15744(13) 0.12288(10) 0.0332(3) Uani 1 1 d . . . . .
H3D H 0.255017 0.218258 0.116352 0.040 Uiso 1 1 calc R U . . .
C4D C 0.43041(11) 0.17685(11) 0.09426(9) 0.0268(2) Uani 1 1 d . . . . .
H4D H 0.452480 0.251565 0.068764 0.032 Uiso 1 1 calc R U . . .
C5D C 0.51453(9) 0.08558(10) 0.10333(7) 0.01973(19) Uani 1 1 d . . . . .
C6D C 0.64265(10) 0.09925(11) 0.07434(8) 0.0227(2) Uani 1 1 d . . . . .
H6DA H 0.651426 0.174530 0.039976 0.027 Uiso 1 1 calc R U . . .
H6DB H 0.663835 0.031419 0.033800 0.027 Uiso 1 1 calc R U . . .
C7D C 0.72847(10) 0.10206(11) 0.15659(8) 0.0226(2) Uani 1 1 d . . . . .
H7DA H 0.715779 0.177154 0.191619 0.027 Uiso 1 1 calc R U . . .
H7DB H 0.709632 0.033775 0.196391 0.027 Uiso 1 1 calc R U . . .
C8D C 0.90174(12) -0.02330(12) 0.11006(11) 0.0327(3) Uani 1 1 d . . . . .
H8DA H 0.868089 -0.052205 0.051974 0.049 Uiso 1 1 calc R U . . .
H8DB H 0.879934 -0.079035 0.158066 0.049 Uiso 1 1 calc R U . . .
H8DC H 0.989385 -0.018396 0.106265 0.049 Uiso 1 1 calc R U . . .
C9D C 0.92723(9) 0.19239(10) 0.12729(8) 0.02055(19) 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
O1A C9A 1.2296(13) . ?
O2A C9A 1.3373(13) . ?
O2A H2AA 0.8400 . ?
N1A C1A 1.3428(14) . ?
N1A C5A 1.3440(14) . ?
N2A C9A 1.3517(14) . ?
N2A C8A 1.4564(16) . ?
N2A C7A 1.4566(14) . ?
C1A C2A 1.3850(17) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.3840(19) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3890(17) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3944(15) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.5033(15) . ?
C6A C7A 1.5311(16) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
O1B C9B 1.2291(13) . ?
O2B C9B 1.3352(13) . ?
O2B H2BA 0.8400 . ?
N1B C1B 1.3434(15) . ?
N1B C5B 1.3453(14) . ?
N2B C9B 1.3543(14) . ?
N2B C7B 1.4554(14) . ?
N2B C8B 1.4564(15) . ?
C1B C2B 1.3808(18) . ?
C1B H1B 0.9500 . ?
C2B C3B 1.383(2) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.3877(18) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3938(15) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.5043(15) . ?
C6B C7B 1.5344(16) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B H8BA 0.9800 . ?
C8B H8BB 0.9800 . ?
C8B H8BC 0.9800 . ?
O1C C9C 1.2270(13) . ?
O2C C9C 1.3327(14) . ?
O2C H2CA 0.8400 . ?
N1C C1C 1.3420(14) . ?
N1C C5C 1.3449(15) . ?
N2C C9C 1.3525(14) . ?
N2C C7C 1.4556(14) . ?
N2C C8C 1.4561(16) . ?
C1C C2C 1.3848(17) . ?
C1C H1C 0.9500 . ?
C2C C3C 1.3847(19) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.3885(17) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.3930(15) . ?
C4C H4C 0.9500 . ?
C5C C6C 1.5039(15) . ?
C6C C7C 1.5302(15) . ?
C6C H6CA 0.9900 . ?
C6C H6CB 0.9900 . ?
C7C H7CA 0.9900 . ?
C7C H7CB 0.9900 . ?
C8C H8CA 0.9800 . ?
C8C H8CB 0.9800 . ?
C8C H8CC 0.9800 . ?
O1D C9D 1.3352(14) . ?
O1D H1DA 0.8400 . ?
O2D C9D 1.2272(13) . ?
N1D C1D 1.3407(15) . ?
N1D C5D 1.3450(15) . ?
N2D C9D 1.3541(14) . ?
N2D C7D 1.4567(14) . ?
N2D C8D 1.4573(16) . ?
C1D C2D 1.3829(19) . ?
C1D H1D 0.9500 . ?
C2D C3D 1.384(2) . ?
C2D H2D 0.9500 . ?
C3D C4D 1.3878(19) . ?
C3D H3D 0.9500 . ?
C4D C5D 1.3920(16) . ?
C4D H4D 0.9500 . ?
C5D C6D 1.5041(15) . ?
C6D C7D 1.5323(16) . ?
C6D H6DA 0.9900 . ?
C6D H6DB 0.9900 . ?
C7D H7DA 0.9900 . ?
C7D H7DB 0.9900 . ?
C8D H8DA 0.9800 . ?
C8D H8DB 0.9800 . ?
C8D H8DC 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
C9A O2A H2AA 109.5 . . ?
C1A N1A C5A 118.77(9) . . ?
C9A N2A C8A 118.65(10) . . ?
C9A N2A C7A 122.97(9) . . ?
C8A N2A C7A 118.05(9) . . ?
N1A C1A C2A 123.10(11) . . ?
N1A C1A H1A 118.4 . . ?
C2A C1A H1A 118.4 . . ?
C3A C2A C1A 118.30(11) . . ?
C3A C2A H2A 120.8 . . ?
C1A C2A H2A 120.8 . . ?
C2A C3A C4A 119.08(10) . . ?
C2A C3A H3A 120.5 . . ?
C4A C3A H3A 120.5 . . ?
C3A C4A C5A 119.39(11) . . ?
C3A C4A H4A 120.3 . . ?
C5A C4A H4A 120.3 . . ?
N1A C5A C4A 121.35(10) . . ?
N1A C5A C6A 116.15(9) . . ?
C4A C5A C6A 122.50(10) . . ?
C5A C6A C7A 111.94(9) . . ?
C5A C6A H6AA 109.2 . . ?
C7A C6A H6AA 109.2 . . ?
C5A C6A H6AB 109.2 . . ?
C7A C6A H6AB 109.2 . . ?
H6AA C6A H6AB 107.9 . . ?
N2A C7A C6A 112.04(9) . . ?
N2A C7A H7AA 109.2 . . ?
C6A C7A H7AA 109.2 . . ?
N2A C7A H7AB 109.2 . . ?
C6A C7A H7AB 109.2 . . ?
H7AA C7A H7AB 107.9 . . ?
N2A C8A H8AA 109.5 . . ?
N2A C8A H8AB 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
N2A C8A H8AC 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
O1A C9A O2A 123.24(10) . . ?
O1A C9A N2A 123.30(10) . . ?
O2A C9A N2A 113.45(9) . . ?
C9B O2B H2BA 109.5 . . ?
C1B N1B C5B 118.75(10) . . ?
C9B N2B C7B 123.65(9) . . ?
C9B N2B C8B 118.97(9) . . ?
C7B N2B C8B 117.37(9) . . ?
N1B C1B C2B 123.04(12) . . ?
N1B C1B H1B 118.5 . . ?
C2B C1B H1B 118.5 . . ?
C1B C2B C3B 118.35(11) . . ?
C1B C2B H2B 120.8 . . ?
C3B C2B H2B 120.8 . . ?
C2B C3B C4B 119.28(11) . . ?
C2B C3B H3B 120.4 . . ?
C4B C3B H3B 120.4 . . ?
C3B C4B C5B 119.15(11) . . ?
C3B C4B H4B 120.4 . . ?
C5B C4B H4B 120.4 . . ?
N1B C5B C4B 121.41(10) . . ?
N1B C5B C6B 116.06(9) . . ?
C4B C5B C6B 122.53(10) . . ?
C5B C6B C7B 110.60(9) . . ?
C5B C6B H6BA 109.5 . . ?
C7B C6B H6BA 109.5 . . ?
C5B C6B H6BB 109.5 . . ?
C7B C6B H6BB 109.5 . . ?
H6BA C6B H6BB 108.1 . . ?
N2B C7B C6B 112.84(9) . . ?
N2B C7B H7BA 109.0 . . ?
C6B C7B H7BA 109.0 . . ?
N2B C7B H7BB 109.0 . . ?
C6B C7B H7BB 109.0 . . ?
H7BA C7B H7BB 107.8 . . ?
N2B C8B H8BA 109.5 . . ?
N2B C8B H8BB 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
N2B C8B H8BC 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
O1B C9B O2B 123.05(10) . . ?
O1B C9B N2B 123.25(10) . . ?
O2B C9B N2B 113.70(9) . . ?
C9C O2C H2CA 109.5 . . ?
C1C N1C C5C 118.72(10) . . ?
C9C N2C C7C 123.01(10) . . ?
C9C N2C C8C 119.53(9) . . ?
C7C N2C C8C 117.46(10) . . ?
N1C C1C C2C 122.95(11) . . ?
N1C C1C H1C 118.5 . . ?
C2C C1C H1C 118.5 . . ?
C3C C2C C1C 118.48(11) . . ?
C3C C2C H2C 120.8 . . ?
C1C C2C H2C 120.8 . . ?
C2C C3C C4C 119.00(11) . . ?
C2C C3C H3C 120.5 . . ?
C4C C3C H3C 120.5 . . ?
C3C C4C C5C 119.31(11) . . ?
C3C C4C H4C 120.3 . . ?
C5C C4C H4C 120.3 . . ?
N1C C5C C4C 121.52(10) . . ?
N1C C5C C6C 116.18(9) . . ?
C4C C5C C6C 122.30(10) . . ?
C5C C6C C7C 111.61(9) . . ?
C5C C6C H6CA 109.3 . . ?
C7C C6C H6CA 109.3 . . ?
C5C C6C H6CB 109.3 . . ?
C7C C6C H6CB 109.3 . . ?
H6CA C6C H6CB 108.0 . . ?
N2C C7C C6C 112.42(9) . . ?
N2C C7C H7CA 109.1 . . ?
C6C C7C H7CA 109.1 . . ?
N2C C7C H7CB 109.1 . . ?
C6C C7C H7CB 109.1 . . ?
H7CA C7C H7CB 107.9 . . ?
N2C C8C H8CA 109.5 . . ?
N2C C8C H8CB 109.5 . . ?
H8CA C8C H8CB 109.5 . . ?
N2C C8C H8CC 109.5 . . ?
H8CA C8C H8CC 109.5 . . ?
H8CB C8C H8CC 109.5 . . ?
O1C C9C O2C 123.31(11) . . ?
O1C C9C N2C 123.25(10) . . ?
O2C C9C N2C 113.44(9) . . ?
C9D O1D H1DA 109.5 . . ?
C1D N1D C5D 118.99(10) . . ?
C9D N2D C7D 123.28(10) . . ?
C9D N2D C8D 119.38(10) . . ?
C7D N2D C8D 117.32(10) . . ?
N1D C1D C2D 122.89(13) . . ?
N1D C1D H1D 118.6 . . ?
C2D C1D H1D 118.6 . . ?
C1D C2D C3D 118.33(12) . . ?
C1D C2D H2D 120.8 . . ?
C3D C2D H2D 120.8 . . ?
C2D C3D C4D 119.24(12) . . ?
C2D C3D H3D 120.4 . . ?
C4D C3D H3D 120.4 . . ?
C3D C4D C5D 119.22(12) . . ?
C3D C4D H4D 120.4 . . ?
C5D C4D H4D 120.4 . . ?
N1D C5D C4D 121.31(10) . . ?
N1D C5D C6D 116.03(10) . . ?
C4D C5D C6D 122.66(11) . . ?
C5D C6D C7D 110.97(9) . . ?
C5D C6D H6DA 109.4 . . ?
C7D C6D H6DA 109.4 . . ?
C5D C6D H6DB 109.4 . . ?
C7D C6D H6DB 109.4 . . ?
H6DA C6D H6DB 108.0 . . ?
N2D C7D C6D 112.34(10) . . ?
N2D C7D H7DA 109.1 . . ?
C6D C7D H7DA 109.1 . . ?
N2D C7D H7DB 109.1 . . ?
C6D C7D H7DB 109.1 . . ?
H7DA C7D H7DB 107.9 . . ?
N2D C8D H8DA 109.5 . . ?
N2D C8D H8DB 109.5 . . ?
H8DA C8D H8DB 109.5 . . ?
N2D C8D H8DC 109.5 . . ?
H8DA C8D H8DC 109.5 . . ?
H8DB C8D H8DC 109.5 . . ?
O2D C9D O1D 123.15(10) . . ?
O2D C9D N2D 123.56(11) . . ?
O1D C9D N2D 113.29(9) . . ?

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
C5A N1A C1A C2A 0.02(17) . . . . ?
N1A C1A C2A C3A -0.22(18) . . . . ?
C1A C2A C3A C4A 0.63(18) . . . . ?
C2A C3A C4A C5A -0.85(18) . . . . ?
C1A N1A C5A C4A -0.24(16) . . . . ?
C1A N1A C5A C6A 179.71(10) . . . . ?
C3A C4A C5A N1A 0.66(17) . . . . ?
C3A C4A C5A C6A -179.28(11) . . . . ?
N1A C5A C6A C7A 68.11(13) . . . . ?
C4A C5A C6A C7A -111.94(12) . . . . ?
C9A N2A C7A C6A -93.01(13) . . . . ?
C8A N2A C7A C6A 80.34(14) . . . . ?
C5A C6A C7A N2A -170.74(9) . . . . ?
C8A N2A C9A O1A 5.23(18) . . . . ?
C7A N2A C9A O1A 178.54(11) . . . . ?
C8A N2A C9A O2A -175.21(11) . . . . ?
C7A N2A C9A O2A -1.89(16) . . . . ?
C5B N1B C1B C2B 0.79(18) . . . . ?
N1B C1B C2B C3B -0.14(19) . . . . ?
C1B C2B C3B C4B -0.97(19) . . . . ?
C2B C3B C4B C5B 1.42(19) . . . . ?
C1B N1B C5B C4B -0.31(17) . . . . ?
C1B N1B C5B C6B 179.45(10) . . . . ?
C3B C4B C5B N1B -0.78(18) . . . . ?
C3B C4B C5B C6B 179.47(11) . . . . ?
N1B C5B C6B C7B -67.72(13) . . . . ?
C4B C5B C6B C7B 112.04(12) . . . . ?
C9B N2B C7B C6B 103.11(12) . . . . ?
C8B N2B C7B C6B -75.81(13) . . . . ?
C5B C6B C7B N2B 170.17(9) . . . . ?
C7B N2B C9B O1B 179.51(11) . . . . ?
C8B N2B C9B O1B -1.58(18) . . . . ?
C7B N2B C9B O2B -0.68(16) . . . . ?
C8B N2B C9B O2B 178.23(11) . . . . ?
C5C N1C C1C C2C -0.86(17) . . . . ?
N1C C1C C2C C3C 1.13(18) . . . . ?
C1C C2C C3C C4C -0.12(18) . . . . ?
C2C C3C C4C C5C -1.08(18) . . . . ?
C1C N1C C5C C4C -0.42(16) . . . . ?
C1C N1C C5C C6C 179.49(10) . . . . ?
C3C C4C C5C N1C 1.39(17) . . . . ?
C3C C4C C5C C6C -178.52(11) . . . . ?
N1C C5C C6C C7C 67.86(13) . . . . ?
C4C C5C C6C C7C -112.23(12) . . . . ?
C9C N2C C7C C6C -98.74(13) . . . . ?
C8C N2C C7C C6C 81.07(14) . . . . ?
C5C C6C C7C N2C -169.90(9) . . . . ?
C7C N2C C9C O1C -177.88(11) . . . . ?
C8C N2C C9C O1C 2.31(18) . . . . ?
C7C N2C C9C O2C 1.62(16) . . . . ?
C8C N2C C9C O2C -178.19(11) . . . . ?
C5D N1D C1D C2D 0.69(19) . . . . ?
N1D C1D C2D C3D 0.4(2) . . . . ?
C1D C2D C3D C4D -1.2(2) . . . . ?
C2D C3D C4D C5D 0.98(19) . . . . ?
C1D N1D C5D C4D -0.96(17) . . . . ?
C1D N1D C5D C6D 178.98(11) . . . . ?
C3D C4D C5D N1D 0.13(18) . . . . ?
C3D C4D C5D C6D -179.81(11) . . . . ?
N1D C5D C6D C7D -68.53(13) . . . . ?
C4D C5D C6D C7D 111.41(12) . . . . ?
C9D N2D C7D C6D 100.24(13) . . . . ?
C8D N2D C7D C6D -81.48(14) . . . . ?
C5D C6D C7D N2D 170.53(10) . . . . ?
C7D N2D C9D O2D 179.62(11) . . . . ?
C8D N2D C9D O2D 1.37(18) . . . . ?
C7D N2D C9D O1D -0.12(16) . . . . ?
C8D N2D C9D O1D -178.37(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2A H2AA N1B 0.84 1.84 2.6798(13) 177.1 . yes
O2B H2BA N1A 0.84 1.84 2.6779(12) 176.5 1_655 yes
O2C H2CA N1D 0.84 1.83 2.6721(13) 175.6 1_565 yes
O1D H1DA N1C 0.84 1.84 2.6756(13) 176.5 . yes

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.053

