# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_nc193ter-b
_database_code_depnum_ccdc_archive 'CCDC 1412260'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-09-25 downloaded from the CCDC.
;

_audit_creation_date             2012-05-24T15:05:39-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H28 N4 O2'
_chemical_formula_sum            'C16 H28 N4 O2'
_chemical_formula_weight         308.42

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  -P2yn
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   5.9879(5)
_cell_length_b                   19.2936(13)
_cell_length_c                   13.5403(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.795(7)
_cell_angle_gamma                90
_cell_volume                     1564.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2114
_cell_measurement_theta_min      3.0021
_cell_measurement_theta_max      31.6457

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       'planar // (0 1 0)'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.02
_exptl_crystal_density_diffrn    1.31
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 0 0.01
0 -1 0 0.01
0 0 1 0.14
0 0 -1 0.15
1 0 0 0.135
-1 0 0 0.155
-1 0 -3 0.18
1 0 8 0.15
-1 0 -1 0.16
1 2 -20 0.15

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.9772
_exptl_absorpt_correction_T_max  0.9982

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed X-ray tube'
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3622
_diffrn_orient_matrix_ub_11      -0.0136334901
_diffrn_orient_matrix_ub_12      0.0284068581
_diffrn_orient_matrix_ub_13      0.0326144649
_diffrn_orient_matrix_ub_21      0.0131611421
_diffrn_orient_matrix_ub_22      0.0233566082
_diffrn_orient_matrix_ub_23      -0.0399587035
_diffrn_orient_matrix_ub_31      -0.1169603847
_diffrn_orient_matrix_ub_32      -0.0006575053
_diffrn_orient_matrix_ub_33      -0.0090785539
_diffrn_measurement_device       'Kappa-geometry diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0925
_diffrn_reflns_av_unetI/netI     0.1378
_diffrn_reflns_number            13412
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             3861
_reflns_number_gt                1649
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
        WinGX (Farrugia, 1999)
        PLATON (Spek, 1990-2003)
        PARST (Nardelli, 1999)
        enCIFer (Allen et al., 2004)
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0289P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3861
_refine_ls_number_parameters     204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1647
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.0903
_refine_ls_wR_factor_gt          0.0711
_refine_ls_goodness_of_fit_ref   0.842
_refine_ls_restrained_S_all      0.842
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.041

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2507(3) 0.11799(10) 0.50360(15) 0.0251(5) Uani 1 1 d . . .
C2 C 0.2171(3) 0.09299(9) 0.39808(14) 0.0270(5) Uani 1 1 d . . .
H2 H 0.3597 0.1026 0.363 0.032 Uiso 1 1 calc R . .
C3 C 0.0341(4) 0.13267(10) 0.34263(15) 0.0323(5) Uani 1 1 d . . .
H3A H 0.0538 0.126 0.2708 0.039 Uiso 1 1 calc R . .
H3B H -0.1128 0.113 0.3602 0.039 Uiso 1 1 calc R . .
C4 C 0.2320(3) 0.23979(10) 0.32328(13) 0.0285(5) Uani 1 1 d . . .
H4A H 0.2386 0.2301 0.2516 0.034 Uiso 1 1 calc R . .
H4B H 0.3676 0.22 0.355 0.034 Uiso 1 1 calc R . .
C5 C 0.2278(3) 0.31655(10) 0.33975(13) 0.0289(5) Uani 1 1 d . . .
H5A H 0.365 0.3378 0.3132 0.035 Uiso 1 1 calc R . .
H5B H 0.0975 0.3371 0.3047 0.035 Uiso 1 1 calc R . .
C6 C 0.2321(4) 0.40586(10) 0.46210(14) 0.0316(5) Uani 1 1 d . . .
H6A H 0.1112 0.4299 0.4251 0.038 Uiso 1 1 calc R . .
H6B H 0.3767 0.4226 0.4367 0.038 Uiso 1 1 calc R . .
C7 C 0.2163(4) 0.42353(10) 0.57114(15) 0.0386(6) Uani 1 1 d . . .
H7A H 0.1981 0.4742 0.5788 0.046 Uiso 1 1 calc R . .
H7B H 0.3565 0.4098 0.6055 0.046 Uiso 1 1 calc R . .
C8 C 0.0199(4) 0.38655(11) 0.61818(17) 0.0415(6) Uani 1 1 d . . .
H8A H 0.0275 0.3933 0.6906 0.05 Uiso 1 1 calc R . .
H8B H -0.1212 0.4075 0.5936 0.05 Uiso 1 1 calc R . .
C9 C 0.2103(3) 0.27862(10) 0.64348(14) 0.0309(5) Uani 1 1 d . . .
H9A H 0.2143 0.2907 0.7146 0.037 Uiso 1 1 calc R . .
H9B H 0.3491 0.2962 0.6135 0.037 Uiso 1 1 calc R . .
C10 C 0.2001(4) 0.20175(10) 0.63231(13) 0.0295(5) Uani 1 1 d . . .
H10A H 0.3357 0.1806 0.6622 0.035 Uiso 1 1 calc R . .
H10B H 0.0685 0.1836 0.6674 0.035 Uiso 1 1 calc R . .
C11 C 0.0062(3) 0.21954(10) 0.46921(14) 0.0239(5) Uani 1 1 d . . .
C12 C 0.0119(3) 0.29999(10) 0.48871(14) 0.0242(5) Uani 1 1 d . . .
C13 C 0.1809(4) 0.01490(10) 0.39347(15) 0.0339(5) Uani 1 1 d . . .
H13A H 0.272 -0.0074 0.4461 0.041 Uiso 1 1 calc R . .
H13B H 0.022 0.0048 0.4067 0.041 Uiso 1 1 calc R . .
C14 C 0.2417(4) -0.01630(12) 0.29491(15) 0.0449(6) Uani 1 1 d . . .
H14A H 0.1992 -0.0659 0.2944 0.054 Uiso 1 1 calc R . .
H14B H 0.1547 0.0072 0.242 0.054 Uiso 1 1 calc R . .
C15 C -0.2181(3) 0.19037(10) 0.50354(15) 0.0340(5) Uani 1 1 d . . .
H15A H -0.2551 0.2105 0.5677 0.051 Uiso 1 1 calc R . .
H15B H -0.2073 0.1399 0.5097 0.051 Uiso 1 1 calc R . .
H15C H -0.3352 0.2022 0.4551 0.051 Uiso 1 1 calc R . .
C16 C -0.2054(3) 0.33035(10) 0.44473(16) 0.0359(6) Uani 1 1 d . . .
H16A H -0.3286 0.3218 0.49 0.054 Uiso 1 1 calc R . .
H16B H -0.2383 0.3082 0.381 0.054 Uiso 1 1 calc R . .
H16C H -0.1876 0.3804 0.4351 0.054 Uiso 1 1 calc R . .
N1 N 0.1841(3) 0.18304(8) 0.52747(11) 0.0220(4) Uani 1 1 d . . .
N2 N 0.0336(3) 0.20682(8) 0.36417(11) 0.0256(4) Uani 1 1 d . . .
N3 N 0.2138(3) 0.33060(8) 0.44513(11) 0.0224(4) Uani 1 1 d . . .
N4 N 0.0180(3) 0.31173(8) 0.59620(12) 0.0292(4) Uani 1 1 d . . .
O1 O 0.3488(2) 0.08118(7) 0.56437(10) 0.0385(4) Uani 1 1 d . . .
O2 O 0.4725(3) -0.01054(8) 0.27428(11) 0.0510(5) Uani 1 1 d . . .
H2O H 0.551(4) -0.0350(13) 0.3234(18) 0.077 Uiso 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 O1 1.230(2) . ?
C1 N1 1.357(2) . ?
C1 C2 1.519(3) . ?
C2 C3 1.526(3) . ?
C2 C13 1.523(3) . ?
C2 H2 1 . ?
C3 N2 1.460(2) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 N2 1.463(2) . ?
C4 C5 1.498(3) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 N3 1.456(2) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 N3 1.474(2) . ?
C6 C7 1.520(3) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 C8 1.523(3) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 N4 1.474(2) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 N4 1.457(2) . ?
C9 C10 1.492(3) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 N1 1.467(2) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C11 N2 1.455(2) . ?
C11 N1 1.493(2) . ?
C11 C15 1.534(3) . ?
C11 C12 1.575(3) . ?
C12 N4 1.473(2) . ?
C12 N3 1.476(2) . ?
C12 C16 1.539(3) . ?
C13 C14 1.513(3) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 O2 1.418(3) . ?
C14 H14A 0.99 . ?
C14 H14B 0.99 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
O2 H2O 0.93(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 120.91(18) . . ?
O1 C1 C2 120.11(17) . . ?
N1 C1 C2 118.83(17) . . ?
C1 C2 C3 112.85(16) . . ?
C1 C2 C13 111.69(16) . . ?
C3 C2 C13 112.03(17) . . ?
C1 C2 H2 106.6 . . ?
C3 C2 H2 106.6 . . ?
C13 C2 H2 106.6 . . ?
N2 C3 C2 113.38(16) . . ?
N2 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
N2 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
N2 C4 C5 110.98(16) . . ?
N2 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108 . . ?
N3 C5 C4 109.35(16) . . ?
N3 C5 H5A 109.8 . . ?
C4 C5 H5A 109.8 . . ?
N3 C5 H5B 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
N3 C6 C7 111.53(16) . . ?
N3 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
N3 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108 . . ?
C6 C7 C8 111.11(18) . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108 . . ?
N4 C8 C7 112.22(17) . . ?
N4 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
N4 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N4 C9 C10 111.11(17) . . ?
N4 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
N4 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108 . . ?
N1 C10 C9 110.17(16) . . ?
N1 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
N1 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
N2 C11 N1 110.34(15) . . ?
N2 C11 C15 110.21(16) . . ?
N1 C11 C15 106.75(15) . . ?
N2 C11 C12 109.13(15) . . ?
N1 C11 C12 111.26(15) . . ?
C15 C11 C12 109.13(16) . . ?
N4 C12 N3 108.91(15) . . ?
N4 C12 C16 109.47(16) . . ?
N3 C12 C16 112.68(16) . . ?
N4 C12 C11 108.51(15) . . ?
N3 C12 C11 110.08(15) . . ?
C16 C12 C11 107.10(16) . . ?
C14 C13 C2 113.19(18) . . ?
C14 C13 H13A 108.9 . . ?
C2 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C2 C13 H13B 108.9 . . ?
H13A C13 H13B 107.8 . . ?
O2 C14 C13 112.92(19) . . ?
O2 C14 H14A 109 . . ?
C13 C14 H14A 109 . . ?
O2 C14 H14B 109 . . ?
C13 C14 H14B 109 . . ?
H14A C14 H14B 107.8 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C1 N1 C10 116.28(16) . . ?
C1 N1 C11 121.33(15) . . ?
C10 N1 C11 115.57(15) . . ?
C11 N2 C3 111.17(15) . . ?
C11 N2 C4 113.57(15) . . ?
C3 N2 C4 110.26(16) . . ?
C5 N3 C6 109.33(15) . . ?
C5 N3 C12 112.09(15) . . ?
C6 N3 C12 113.05(15) . . ?
C9 N4 C12 112.06(15) . . ?
C9 N4 C8 109.69(16) . . ?
C12 N4 C8 110.50(16) . . ?
C14 O2 H2O 107.5(16) . . ?

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
O2 H2O O1 0.93(2) 1.86(2) 2.777(2) 168(2) 3_656

_iucr_refine_instruction_details 
;
TITL NC193ter-b at 170 K in P2(1)/n (#14 in standard setting)
CELL  0.71073   5.9879  19.2936  13.5403   90.000   90.795   90.000
ZERR     4.00   0.0005   0.0013   0.0009    0.000    0.007    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  64   112  16   8
MERG   2
OMIT     0   0   2
SHEL   13 0.75
EQIV   $1  -x+1, -y, -z+1
HTAB   O2 O1_$1
FMAP   2
PLAN   20
SIZE     0.02   0.29   0.29
ACTA
BOND   $H
L.S.   4
TEMP  -103.00
WGHT    0.027600
FVAR       0.56802
MOLE    1
C1    1    0.250655    0.117997    0.503604    11.00000    0.01988    0.02747 =
         0.02821    0.00450    0.00201   -0.00211
C2    1    0.217113    0.092993    0.398090    11.00000    0.03166    0.02588 =
         0.02351    0.00000    0.00159   -0.00055
AFIX  13
H2    2    0.359686    0.102580    0.363003    11.00000   -1.20000
AFIX   0
C3    1    0.034068    0.132671    0.342639    11.00000    0.03995    0.03040 =
         0.02659   -0.00313   -0.00513    0.00144
AFIX  23
H3A   2    0.053784    0.126017    0.270788    11.00000   -1.20000
H3B   2   -0.112812    0.112980    0.360183    11.00000   -1.20000
AFIX   0
C4    1    0.231987    0.239786    0.323280    11.00000    0.03675    0.03310 =
         0.01579    0.00222    0.00245    0.00442
AFIX  23
H4A   2    0.238528    0.230142    0.251566    11.00000   -1.20000
H4B   2    0.367526    0.219948    0.355010    11.00000   -1.20000
AFIX   0
C5    1    0.227826    0.316556    0.339756    11.00000    0.02713    0.03672 =
         0.02308    0.00436    0.00185    0.00185
AFIX  23
H5A   2    0.365029    0.337762    0.313174    11.00000   -1.20000
H5B   2    0.097508    0.337083    0.304756    11.00000   -1.20000
AFIX   0
C6    1    0.232118    0.405859    0.462090    11.00000    0.02954    0.02895 =
         0.03637    0.00123    0.00188    0.00044
AFIX  23
H6A   2    0.111187    0.429918    0.425139    11.00000   -1.20000
H6B   2    0.376682    0.422598    0.436695    11.00000   -1.20000
AFIX   0
C7    1    0.216307    0.423534    0.571135    11.00000    0.04694    0.02625 =
         0.04262   -0.00678    0.00139   -0.00017
AFIX  23
H7A   2    0.198116    0.474240    0.578825    11.00000   -1.20000
H7B   2    0.356452    0.409774    0.605478    11.00000   -1.20000
AFIX   0
C8    1    0.019872    0.386538    0.618185    11.00000    0.04944    0.03609 =
         0.03931   -0.00956    0.00813    0.00379
AFIX  23
H8A   2    0.027460    0.393240    0.690642    11.00000   -1.20000
H8B   2   -0.121199    0.407503    0.593608    11.00000   -1.20000
AFIX   0
C9    1    0.210304    0.278612    0.643482    11.00000    0.03695    0.03858 =
         0.01744   -0.00347    0.00211   -0.00320
AFIX  23
H9A   2    0.214280    0.290659    0.714556    11.00000   -1.20000
H9B   2    0.349113    0.296184    0.613488    11.00000   -1.20000
AFIX   0
C10   1    0.200052    0.201752    0.632305    11.00000    0.03529    0.03557 =
         0.01777   -0.00021   -0.00027   -0.00030
AFIX  23
H10A  2    0.335656    0.180608    0.662166    11.00000   -1.20000
H10B  2    0.068492    0.183550    0.667400    11.00000   -1.20000
AFIX   0
C11   1    0.006188    0.219536    0.469202    11.00000    0.02152    0.02710 =
         0.02296   -0.00062   -0.00137    0.00158
C12   1    0.011865    0.299987    0.488709    11.00000    0.01866    0.02969 =
         0.02450   -0.00092    0.00252    0.00345
C13   1    0.180875    0.014910    0.393483    11.00000    0.03980    0.02872 =
         0.03331   -0.00424    0.00464   -0.00071
AFIX  23
H13A  2    0.271957   -0.007439    0.446096    11.00000   -1.20000
H13B  2    0.021999    0.004779    0.406721    11.00000   -1.20000
AFIX   0
C14   1    0.241644   -0.016305    0.294905    11.00000    0.06164    0.03324 =
         0.03997   -0.00329   -0.00048    0.00622
AFIX  23
H14A  2    0.199149   -0.065893    0.294412    11.00000   -1.20000
H14B  2    0.154702    0.007212    0.241979    11.00000   -1.20000
AFIX   0
C15   1   -0.218089    0.190377    0.503539    11.00000    0.02396    0.03576 =
         0.04259    0.00050    0.00340   -0.00187
AFIX 137
H15A  2   -0.255062    0.210462    0.567748    11.00000   -1.50000
H15B  2   -0.207289    0.139873    0.509681    11.00000   -1.50000
H15C  2   -0.335185    0.202167    0.455122    11.00000   -1.50000
AFIX   0
C16   1   -0.205369    0.330353    0.444736    11.00000    0.02356    0.03191 =
         0.05226    0.00064   -0.00006    0.00283
AFIX 137
H16A  2   -0.328574    0.321806    0.490046    11.00000   -1.50000
H16B  2   -0.238333    0.308210    0.381049    11.00000   -1.50000
H16C  2   -0.187536    0.380380    0.435112    11.00000   -1.50000
AFIX   0
N1    3    0.184131    0.183041    0.527461    11.00000    0.02359    0.02523 =
         0.01721   -0.00081   -0.00083    0.00112
N2    3    0.033577    0.206825    0.364168    11.00000    0.02977    0.02543 =
         0.02160   -0.00169   -0.00402    0.00020
N3    3    0.213792    0.330602    0.445135    11.00000    0.02250    0.02146 =
         0.02335    0.00026    0.00144   -0.00030
N4    3    0.018012    0.311724    0.596195    11.00000    0.03145    0.02733 =
         0.02902   -0.00487    0.00703    0.00318
O1    4    0.348789    0.081183    0.564376    11.00000    0.04760    0.03481 =
         0.03279    0.00638   -0.00787    0.00956
O2    4    0.472492   -0.010534    0.274279    11.00000    0.06779    0.05131 =
         0.03448    0.01187    0.01243    0.02264
H2O   2    0.550735   -0.035004    0.323303    11.00000   -1.50000
HKLF    4
 
REM  NC193ter-b at 170 K in P2(1)/n (#14 in standard setting)
REM R1 =  0.0534 for   1649 Fo > 4sig(Fo)  and  0.1648 for all   3861 data
REM    204 parameters refined using      0 restraints
 
END
 
WGHT      0.0275      0.0000
REM Highest difference peak  0.201,  deepest hole -0.183,  1-sigma level  0.041
Q1    1   0.0029  0.2609  0.4714  11.00000  0.05    0.20
Q2    1   0.2777  0.2986  0.4961  11.00000  0.05    0.20
Q3    1  -0.0860  0.2820  0.6408  11.00000  0.05    0.17
Q4    1   0.1735  0.1021  0.4546  11.00000  0.05    0.16
Q5    1  -0.0025  0.3579  0.7013  11.00000  0.05    0.16
Q6    1   0.2238  0.2020  0.5670  11.00000  0.05    0.16
Q7    1   0.1438  0.1098  0.3799  11.00000  0.05    0.15
Q8    1   0.3432  0.5014  0.6040  11.00000  0.05    0.15
Q9    1   0.2535  0.0683  0.4471  11.00000  0.05    0.14
Q10   1   0.0961  0.3148  0.4558  11.00000  0.05    0.14
Q11   1  -0.1036  0.1207  0.2938  11.00000  0.05    0.14
Q12   1  -0.0948  0.3074  0.4637  11.00000  0.05    0.14
Q13   1   0.2686  0.1608  0.4988  11.00000  0.05    0.14
Q14   1   0.5021  0.4055  0.3584  11.00000  0.05    0.13
Q15   1   0.0806  0.2022  0.5031  11.00000  0.05    0.13
Q16   1   0.3946  0.0374  0.5725  11.00000  0.05    0.13
Q17   1   0.4317  0.3475  0.3391  11.00000  0.05    0.13
Q18   1  -0.0547  0.2106  0.3219  11.00000  0.05    0.13
Q19   1   0.2987  0.4554  0.5827  11.00000  0.05    0.13
Q20   1   0.0544  0.2993  0.5324  11.00000  0.05    0.13

;


# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_nc281-c
_database_code_depnum_ccdc_archive 'CCDC 1412261'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-09-25 downloaded from the CCDC.
;

_audit_creation_date             2012-10-15T18:04:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H26 N4 O2'
_chemical_formula_sum            'C15 H26 N4 O2'
_chemical_formula_weight         294.4

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n
_symmetry_space_group_name_Hall  -P2yn
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   11.7908(8)
_cell_length_b                   10.4516(8)
_cell_length_c                   12.3326(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.971(6)
_cell_angle_gamma                90
_cell_volume                     1505.10(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    2384
_cell_measurement_theta_min      2.9591
_cell_measurement_theta_max      31.6801

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       'rectangles, hygroscopic'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 1 0.03
-1 0 -1 0.02
1 0 -1 0.04
-1 0 1 0.04
0 -1 0 0.095
0 1 0 0.095
-4 1 17 0.03
8 1 1 0.03
9 4 13 0.035
1 -1 -3 0.055
-17 -1 2 0.03
-1 0 -8 0.025
-1 -2 -2 0.07
2 -1 1 0.06
1 -3 3 0.08
-3 -3 1 0.08
1 2 -1 0.085
-3 3 1 0.075

_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.9795
_exptl_absorpt_correction_T_max  0.9956

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed X-ray tube'
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3622
_diffrn_orient_matrix_ub_11      0.0157469091
_diffrn_orient_matrix_ub_12      -0.0375286364
_diffrn_orient_matrix_ub_13      -0.0433735937
_diffrn_orient_matrix_ub_21      0.0536520374
_diffrn_orient_matrix_ub_22      0.0315500391
_diffrn_orient_matrix_ub_23      0.0050501106
_diffrn_orient_matrix_ub_31      0.0235632541
_diffrn_orient_matrix_ub_32      -0.0467715848
_diffrn_orient_matrix_ub_33      0.038188314
_diffrn_measurement_device       'Kappa-geometry diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0875
_diffrn_reflns_number            10760
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_full        25.68
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             2854
_reflns_number_gt                1598
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
;
_computing_structure_solution    'SIR-92 (Altomare et al., 1992)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
        WinGX (Farrugia, 1999)
        PLATON (Spek, 1990-2003)
        enCIFer (Allen et al., 2004)
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0281P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2854
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0701
_refine_ls_wR_factor_gt          0.0634
_refine_ls_goodness_of_fit_ref   0.805
_refine_ls_restrained_S_all      0.805
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.036

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32580(15) 0.39849(16) 0.34974(14) 0.0217(4) Uani 1 1 d . . .
C2 C 0.42472(14) 0.35116(16) 0.29360(13) 0.0218(4) Uani 1 1 d . . .
H2 H 0.489 0.4132 0.3128 0.026 Uiso 1 1 calc R . .
C3 C 0.46953(14) 0.22036(16) 0.33514(13) 0.0246(4) Uani 1 1 d . . .
H3A H 0.4181 0.1532 0.2995 0.029 Uiso 1 1 calc R . .
H3B H 0.5463 0.2068 0.3132 0.029 Uiso 1 1 calc R . .
C4 C 0.57275(14) 0.28302(17) 0.50977(14) 0.0267(4) Uani 1 1 d . . .
H4A H 0.5582 0.3747 0.4929 0.032 Uiso 1 1 calc R . .
H4B H 0.6447 0.2585 0.4823 0.032 Uiso 1 1 calc R . .
C5 C 0.58601(14) 0.26345(17) 0.63204(14) 0.0269(5) Uani 1 1 d . . .
H5A H 0.6051 0.1731 0.6507 0.032 Uiso 1 1 calc R . .
H5B H 0.6478 0.3187 0.6691 0.032 Uiso 1 1 calc R . .
C6 C 0.46823(15) 0.29808(18) 0.78285(14) 0.0315(5) Uani 1 1 d . . .
H6A H 0.4945 0.3806 0.8168 0.038 Uiso 1 1 calc R . .
H6B H 0.5136 0.2278 0.8213 0.038 Uiso 1 1 calc R . .
C7 C 0.33899(15) 0.27829(18) 0.78503(13) 0.0299(5) Uani 1 1 d . . .
H7A H 0.3253 0.199 0.8252 0.036 Uiso 1 1 calc R . .
H7B H 0.3064 0.3515 0.8213 0.036 Uiso 1 1 calc R . .
C8 C 0.25486(15) 0.39934(16) 0.62844(13) 0.0248(4) Uani 1 1 d . . .
H8A H 0.3202 0.4577 0.6501 0.03 Uiso 1 1 calc R . .
H8B H 0.1891 0.4304 0.663 0.03 Uiso 1 1 calc R . .
C9 C 0.22411(14) 0.40178(17) 0.50637(13) 0.0253(4) Uani 1 1 d . . .
H9A H 0.1572 0.3457 0.4845 0.03 Uiso 1 1 calc R . .
H9B H 0.2032 0.4899 0.482 0.03 Uiso 1 1 calc R . .
C10 C 0.36673(13) 0.22871(15) 0.48984(13) 0.0183(4) Uani 1 1 d . . .
C11 C 0.38215(14) 0.21697(16) 0.61588(13) 0.0206(4) Uani 1 1 d . . .
C12 C 0.39516(15) 0.35418(18) 0.16908(13) 0.0293(5) Uani 1 1 d . . .
H12A H 0.3305 0.2951 0.1469 0.035 Uiso 1 1 calc R . .
H12B H 0.3697 0.4415 0.1461 0.035 Uiso 1 1 calc R . .
C13 C 0.49466(15) 0.31676(18) 0.11006(14) 0.0332(5) Uani 1 1 d . . .
H13A H 0.5133 0.2253 0.1237 0.04 Uiso 1 1 calc R . .
H13B H 0.4731 0.3288 0.0302 0.04 Uiso 1 1 calc R . .
C14 C 0.28013(14) 0.12799(15) 0.43770(13) 0.0258(5) Uani 1 1 d . . .
H14A H 0.2535 0.1516 0.3615 0.039 Uiso 1 1 calc R . .
H14B H 0.2147 0.1245 0.4787 0.039 Uiso 1 1 calc R . .
H14C H 0.3172 0.0439 0.4398 0.039 Uiso 1 1 calc R . .
C15 C 0.39804(15) 0.07487(16) 0.64729(14) 0.0270(5) Uani 1 1 d . . .
H15A H 0.4336 0.068 0.7238 0.041 Uiso 1 1 calc R . .
H15B H 0.4474 0.0338 0.5998 0.041 Uiso 1 1 calc R . .
H15C H 0.3233 0.0323 0.6383 0.041 Uiso 1 1 calc R . .
N1 N 0.32119(11) 0.35775(13) 0.45422(11) 0.0196(3) Uani 1 1 d . . .
N2 N 0.47768(11) 0.20608(12) 0.45405(11) 0.0197(3) Uani 1 1 d . . .
N3 N 0.47719(11) 0.29735(13) 0.66564(11) 0.0212(4) Uani 1 1 d . . .
N4 N 0.28584(11) 0.26868(13) 0.66823(11) 0.0220(4) Uani 1 1 d . . .
O1 O 0.25750(10) 0.47817(11) 0.30587(10) 0.0308(3) Uani 1 1 d . . .
O2 O 0.59231(10) 0.39307(11) 0.14746(11) 0.0403(4) Uani 1 1 d . . .
H2O H 0.6514 0.3472 0.1539 0.06 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 O1 1.2304(19) . ?
C1 N1 1.3653(19) . ?
C1 C2 1.519(2) . ?
C2 C12 1.527(2) . ?
C2 C3 1.528(2) . ?
C2 H2 1 . ?
C3 N2 1.4638(19) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 N2 1.470(2) . ?
C4 C5 1.508(2) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 N3 1.4460(19) . ?
C5 H5A 0.99 . ?
C5 H5B 0.99 . ?
C6 N3 1.464(2) . ?
C6 C7 1.542(2) . ?
C6 H6A 0.99 . ?
C6 H6B 0.99 . ?
C7 N4 1.492(2) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 N4 1.480(2) . ?
C8 C9 1.499(2) . ?
C8 H8A 0.99 . ?
C8 H8B 0.99 . ?
C9 N1 1.4628(19) . ?
C9 H9A 0.99 . ?
C9 H9B 0.99 . ?
C10 N2 1.4567(19) . ?
C10 N1 1.495(2) . ?
C10 C14 1.543(2) . ?
C10 C11 1.545(2) . ?
C11 N3 1.465(2) . ?
C11 N4 1.484(2) . ?
C11 C15 1.540(2) . ?
C12 C13 1.515(2) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C13 O2 1.424(2) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
O2 H2O 0.84 . ?

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
O1 C1 N1 121.11(16) . . ?
O1 C1 C2 121.13(16) . . ?
N1 C1 C2 117.52(15) . . ?
C1 C2 C12 111.65(14) . . ?
C1 C2 C3 112.96(14) . . ?
C12 C2 C3 112.06(15) . . ?
C1 C2 H2 106.6 . . ?
C12 C2 H2 106.6 . . ?
C3 C2 H2 106.6 . . ?
N2 C3 C2 113.49(14) . . ?
N2 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
N2 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
N2 C4 C5 111.08(14) . . ?
N2 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N2 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108 . . ?
N3 C5 C4 106.27(13) . . ?
N3 C5 H5A 110.5 . . ?
C4 C5 H5A 110.5 . . ?
N3 C5 H5B 110.5 . . ?
C4 C5 H5B 110.5 . . ?
H5A C5 H5B 108.7 . . ?
N3 C6 C7 102.91(13) . . ?
N3 C6 H6A 111.2 . . ?
C7 C6 H6A 111.2 . . ?
N3 C6 H6B 111.2 . . ?
C7 C6 H6B 111.2 . . ?
H6A C6 H6B 109.1 . . ?
N4 C7 C6 106.02(13) . . ?
N4 C7 H7A 110.5 . . ?
C6 C7 H7A 110.5 . . ?
N4 C7 H7B 110.5 . . ?
C6 C7 H7B 110.5 . . ?
H7A C7 H7B 108.7 . . ?
N4 C8 C9 111.28(14) . . ?
N4 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N4 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108 . . ?
N1 C9 C8 109.95(14) . . ?
N1 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
N1 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N2 C10 N1 111.01(13) . . ?
N2 C10 C14 109.46(13) . . ?
N1 C10 C14 107.64(13) . . ?
N2 C10 C11 107.86(13) . . ?
N1 C10 C11 110.77(13) . . ?
C14 C10 C11 110.11(14) . . ?
N3 C11 N4 101.30(13) . . ?
N3 C11 C15 112.85(14) . . ?
N4 C11 C15 108.40(14) . . ?
N3 C11 C10 110.63(13) . . ?
N4 C11 C10 114.74(13) . . ?
C15 C11 C10 108.84(13) . . ?
C13 C12 C2 113.19(14) . . ?
C13 C12 H12A 108.9 . . ?
C2 C12 H12A 108.9 . . ?
C13 C12 H12B 108.9 . . ?
C2 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
O2 C13 C12 110.18(15) . . ?
O2 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
O2 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C1 N1 C9 116.93(13) . . ?
C1 N1 C10 119.93(13) . . ?
C9 N1 C10 115.20(13) . . ?
C10 N2 C3 110.49(13) . . ?
C10 N2 C4 115.35(13) . . ?
C3 N2 C4 110.63(13) . . ?
C5 N3 C6 118.20(13) . . ?
C5 N3 C11 113.39(13) . . ?
C6 N3 C11 105.11(12) . . ?
C8 N4 C11 111.13(13) . . ?
C8 N4 C7 108.02(13) . . ?
C11 N4 C7 101.55(12) . . ?
C13 O2 H2O 109.5 . . ?

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
O2 H2O N4 0.84 1.98 2.8228(18) 177.2 4_665

#----------------------------------------------------------------------------#
#                   SHELXL.RES FILE                                          #
#----------------------------------------------------------------------------#

_iucr_refine_instruction_details 
;
TITL NC281-c at 170 K in P2(1)/n
CELL  0.71073  11.7908  10.4516  12.3326   90.000   97.971   90.000
ZERR     4.00   0.0008   0.0008   0.0008    0.000    0.006    0.000
LATT   1
SYMM  1/2 - X, 1/2 + Y, 1/2 - Z
SFAC  C    H    N    O
UNIT  60   104  16   8
MERG   2
SHEL  15 0.82
EQIV   $1 x+1/2, -y+1/2, z-1/2
HTAB   O2 N4_$1
FMAP   2
PLAN   25
SIZE     0.05   0.08   0.19
ACTA
BOND   $H
L.S.  10
TEMP  -103.00
WGHT    0.028100
FVAR       0.64049
MOLE    1
C1    1    0.325804    0.398493    0.349738    11.00000    0.02142    0.01877 =
         0.02427   -0.00054    0.00123   -0.00028
C2    1    0.424717    0.351162    0.293603    11.00000    0.01779    0.02668 =
         0.02115    0.00392    0.00344    0.00148
AFIX  13
H2    2    0.488951    0.413166    0.312838    11.00000   -1.20000
AFIX   0
C3    1    0.469530    0.220364    0.335143    11.00000    0.02317    0.02692 =
         0.02506    0.00109    0.00853    0.00372
AFIX  23
H3A   2    0.418076    0.153195    0.299509    11.00000   -1.20000
H3B   2    0.546286    0.206781    0.313226    11.00000   -1.20000
AFIX   0
C4    1    0.572754    0.283020    0.509771    11.00000    0.01737    0.03113 =
         0.03178    0.00453    0.00350   -0.00044
AFIX  23
H4A   2    0.558248    0.374659    0.492881    11.00000   -1.20000
H4B   2    0.644706    0.258520    0.482272    11.00000   -1.20000
AFIX   0
C5    1    0.586014    0.263452    0.632045    11.00000    0.02012    0.02983 =
         0.02951    0.00275   -0.00085    0.00032
AFIX  23
H5A   2    0.605145    0.173144    0.650660    11.00000   -1.20000
H5B   2    0.647759    0.318720    0.669083    11.00000   -1.20000
AFIX   0
C6    1    0.468231    0.298080    0.782848    11.00000    0.03603    0.03428 =
         0.02256   -0.00231   -0.00140    0.00433
AFIX  23
H6A   2    0.494483    0.380646    0.816825    11.00000   -1.20000
H6B   2    0.513565    0.227803    0.821330    11.00000   -1.20000
AFIX   0
C7    1    0.338991    0.278287    0.785026    11.00000    0.03621    0.03358 =
         0.02012   -0.00175    0.00422    0.00332
AFIX  23
H7A   2    0.325339    0.198985    0.825171    11.00000   -1.20000
H7B   2    0.306404    0.351452    0.821294    11.00000   -1.20000
AFIX   0
C8    1    0.254860    0.399344    0.628439    11.00000    0.02391    0.02549 =
         0.02565   -0.00503    0.00618    0.00485
AFIX  23
H8A   2    0.320217    0.457689    0.650133    11.00000   -1.20000
H8B   2    0.189065    0.430372    0.662980    11.00000   -1.20000
AFIX   0
C9    1    0.224112    0.401781    0.506373    11.00000    0.02388    0.02605 =
         0.02649   -0.00230    0.00500    0.00689
AFIX  23
H9A   2    0.157173    0.345720    0.484465    11.00000   -1.20000
H9B   2    0.203150    0.489941    0.481959    11.00000   -1.20000
AFIX   0
C10   1    0.366731    0.228709    0.489835    11.00000    0.01836    0.01570 =
         0.02022   -0.00048    0.00091   -0.00014
C11   1    0.382150    0.216972    0.615881    11.00000    0.01904    0.01922 =
         0.02396   -0.00203    0.00412    0.00032
C12   1    0.395156    0.354176    0.169081    11.00000    0.02386    0.03959 =
         0.02507    0.00290    0.00522    0.00209
AFIX  23
H12A  2    0.330459    0.295097    0.146907    11.00000   -1.20000
H12B  2    0.369721    0.441527    0.146113    11.00000   -1.20000
AFIX   0
C13   1    0.494656    0.316756    0.110059    11.00000    0.02618    0.04880 =
         0.02526    0.00165    0.00560    0.00451
AFIX  23
H13A  2    0.513259    0.225284    0.123683    11.00000   -1.20000
H13B  2    0.473091    0.328751    0.030233    11.00000   -1.20000
AFIX   0
C14   1    0.280132    0.127987    0.437702    11.00000    0.02520    0.02817 =
         0.02469   -0.00547    0.00594   -0.00541
AFIX 137
H14A  2    0.253467    0.151601    0.361526    11.00000   -1.50000
H14B  2    0.214708    0.124457    0.478710    11.00000   -1.50000
H14C  2    0.317234    0.043949    0.439766    11.00000   -1.50000
AFIX   0
C15   1    0.398040    0.074866    0.647285    11.00000    0.03367    0.02518 =
         0.02347    0.00378    0.00815    0.00037
AFIX 137
H15A  2    0.433551    0.068020    0.723759    11.00000   -1.50000
H15B  2    0.447412    0.033841    0.599789    11.00000   -1.50000
H15C  2    0.323269    0.032292    0.638294    11.00000   -1.50000
AFIX   0
N1    3    0.321192    0.357751    0.454221    11.00000    0.01731    0.02032 =
         0.02184    0.00199    0.00489    0.00328
N2    3    0.477676    0.206082    0.454046    11.00000    0.01689    0.02265 =
         0.02012    0.00170    0.00421    0.00083
N3    3    0.477195    0.297347    0.665636    11.00000    0.01767    0.02701 =
         0.01822   -0.00248   -0.00010   -0.00017
N4    3    0.285841    0.268679    0.668234    11.00000    0.02494    0.02442 =
         0.01717   -0.00141    0.00519    0.00278
O1    4    0.257500    0.478166    0.305870    11.00000    0.03099    0.03241 =
         0.02903    0.00830    0.00421    0.01211
O2    4    0.592313    0.393073    0.147456    11.00000    0.02689    0.04050 =
         0.05676    0.00108    0.01733    0.00359
AFIX 147
H2O   2    0.651366    0.347205    0.153878    11.00000   -1.50000
HKLF    4
 
REM  NC281-c at 170 K in P2(1)/n
REM R1 =  0.0383 for   1598 Fo > 4sig(Fo)  and  0.0896 for all   2854 data
REM    193 parameters refined using      0 restraints
 
END
 
WGHT      0.0282      0.0000
REM Highest difference peak  0.156,  deepest hole -0.162,  1-sigma level  0.036
Q1    1   0.3822  0.1591  0.6322  11.00000  0.05    0.16
Q2    1   0.4436  0.2278  0.6367  11.00000  0.05    0.15
Q3    1   0.3071  0.2212  0.6116  11.00000  0.05    0.15
Q4    1   0.3781  0.2410  0.5556  11.00000  0.05    0.15
Q5    1   0.3416  0.2997  0.4763  11.00000  0.05    0.14
Q6    1   0.2325  0.2080  0.6799  11.00000  0.05    0.14
Q7    1   0.3036  0.2684  0.7140  11.00000  0.05    0.13
Q8    1   0.4942  0.1315  0.5035  11.00000  0.05    0.13
Q9    1   0.2413  0.2907  0.6406  11.00000  0.05    0.12
Q10   1   0.4652  0.3096  0.3145  11.00000  0.05    0.12
Q11   1   0.6571  0.3864  0.6635  11.00000  0.05    0.12
Q12   1   0.3871  0.3583  0.3383  11.00000  0.05    0.12
Q13   1   0.5276  0.5225  0.4259  11.00000  0.05    0.12
Q14   1   0.5190  0.2815  0.6478  11.00000  0.05    0.12
Q15   1   0.3948  0.3244  0.2411  11.00000  0.05    0.11
Q16   1   0.3292  0.1999  0.4635  11.00000  0.05    0.11
Q17   1   0.4280  0.1262  0.2877  11.00000  0.05    0.11
Q18   1   0.3220  0.3240  0.8245  11.00000  0.05    0.11
Q19   1   0.3451  0.2002  0.2377  11.00000  0.05    0.11
Q20   1   0.2990  0.3320  0.4026  11.00000  0.05    0.11
Q21   1   0.2621  0.4757  0.2303  11.00000  0.05    0.11
Q22   1   0.2728  0.2834  0.8395  11.00000  0.05    0.11
Q23   1   0.2840  0.1158  0.7968  11.00000  0.05    0.11
Q24   1   0.0884  0.2681  0.4806  11.00000  0.05    0.10
Q25   1   0.3430  0.3611  0.2842  11.00000  0.05    0.10

;

#----------------------------------------------------------------------------#
#                   END OF CIF                                               #
#----------------------------------------------------------------------------#



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
####################################################################### 
# 
# 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_nc526-a
_database_code_depnum_ccdc_archive 'CCDC 1412262'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-09-25 downloaded from the CCDC.
;

_audit_creation_date             2013-12-04T10:36:37-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H27 Cl N4 O'
_chemical_formula_sum            'C16 H27 Cl N4 O'
_chemical_formula_weight         326.87
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pna21
_symmetry_space_group_name_Hall  P2c-2n
_symmetry_Int_Tables_number      33
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   19.2249(8)
_cell_length_b                   13.6646(5)
_cell_length_c                   6.0897(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1599.77(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    6056
_cell_measurement_theta_min      2.9758
_cell_measurement_theta_max      31.5471

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       'planar // (1 0 0)'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.05
0 0 -1 0.02
0 1 0 0.15
0 -1 0 0.13
-1 0 0 0.16
1 0 0 0.19
4 -1 24 0.085
-1 17 12 0.13
-2 -1 -3 0.125
2 2 -5 0.16
-2 -1 2 0.14
2 -3 -1 0.205
-1 14 -19 0.105
2 -1 1 0.19
1 -6 10 0.115
1 1 1 0.195
0 -3 4 0.115

_exptl_crystal_recrystallization_method 
;
from hexane solution, by slow evaporation of solvent at room temperature
;
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.9404
_exptl_absorpt_correction_T_max  0.9829

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed X-ray tube'
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          X-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.3622
_diffrn_orient_matrix_ub_11      -0.0121135237
_diffrn_orient_matrix_ub_12      0.0496949198
_diffrn_orient_matrix_ub_13      0.0098804826
_diffrn_orient_matrix_ub_21      -0.0195191862
_diffrn_orient_matrix_ub_22      -0.0146610448
_diffrn_orient_matrix_ub_23      0.0348209865
_diffrn_orient_matrix_ub_31      0.1141174191
_diffrn_orient_matrix_ub_32      0.0027467641
_diffrn_orient_matrix_ub_33      0.0070104055
_diffrn_measurement_device       'Kappa-geometry diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_number            13686
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             2980
_reflns_number_gt                2434
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlis CCD, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_cell_refinement       
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_data_reduction        
;
        CrysAlis RED, Oxford Diffraction Ltd.,
        Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
        (compiled Nov  6 2009,16:24:50)
;
_computing_structure_solution    'SIR-92 (Altomare et al., 1992)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
        WinGX (Farrugia, 1999)
        PLATON (Spek, 1990-2003)
        enCIFer (Allen et al., 2004)
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0656P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2980
_refine_ls_number_parameters     201
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.102
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.01
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(8)
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.054

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.25084(10) 0.28011(13) 0.1885(4) 0.0372(5) Uani 1 1 d . . .
H1A H 0.2598 0.2104 0.1784 0.045 Uiso 1 1 calc R . .
H1B H 0.2677 0.3106 0.0549 0.045 Uiso 1 1 calc R . .
C2 C 0.17417(10) 0.29728(14) 0.2098(4) 0.0383(5) Uani 1 1 d . . .
H2A H 0.1505 0.2724 0.0808 0.046 Uiso 1 1 calc R . .
H2B H 0.1565 0.2627 0.3372 0.046 Uiso 1 1 calc R . .
C3 C 0.08504(10) 0.41947(16) 0.2320(4) 0.0457(5) Uani 1 1 d . . .
H3A H 0.0638 0.3844 0.3532 0.055 Uiso 1 1 calc R . .
H3B H 0.0653 0.3943 0.0966 0.055 Uiso 1 1 calc R . .
C4 C 0.06812(11) 0.52749(17) 0.2521(5) 0.0550(7) Uani 1 1 d . . .
H4A H 0.0787 0.5601 0.1146 0.066 Uiso 1 1 calc R . .
H4B H 0.0188 0.5354 0.2807 0.066 Uiso 1 1 calc R . .
C5 C 0.10940(11) 0.57440(17) 0.4357(5) 0.0524(6) Uani 1 1 d . . .
H5A H 0.103 0.6448 0.4303 0.063 Uiso 1 1 calc R . .
H5B H 0.0917 0.5513 0.5756 0.063 Uiso 1 1 calc R . .
C6 C 0.21426(10) 0.59779(14) 0.2242(4) 0.0394(5) Uani 1 1 d . . .
H6A H 0.2026 0.6669 0.2232 0.047 Uiso 1 1 calc R . .
H6B H 0.1941 0.5681 0.0943 0.047 Uiso 1 1 calc R . .
C7 C 0.29184(10) 0.58616(13) 0.2179(4) 0.0372(5) Uani 1 1 d . . .
H7A H 0.31 0.6142 0.0831 0.045 Uiso 1 1 calc R . .
H7B H 0.3126 0.6207 0.3407 0.045 Uiso 1 1 calc R . .
C8 C 0.37396(9) 0.45765(13) 0.1489(3) 0.0303(4) Uani 1 1 d . . .
C9 C 0.39914(9) 0.35259(13) 0.1761(4) 0.0335(4) Uani 1 1 d . . .
H9 H 0.388 0.3179 0.0397 0.04 Uiso 1 1 calc R . .
C10 C 0.36229(10) 0.29836(14) 0.3626(4) 0.0393(5) Uani 1 1 d . . .
H10A H 0.3679 0.2285 0.3406 0.047 Uiso 1 1 calc R . .
H10B H 0.3845 0.3152 0.5005 0.047 Uiso 1 1 calc R . .
C11 C 0.27712(9) 0.42489(13) 0.4116(3) 0.0292(4) Uani 1 1 d . . .
C12 C 0.19625(10) 0.44514(14) 0.4241(3) 0.0311(4) Uani 1 1 d . . .
C13 C 0.31140(11) 0.45820(16) 0.6273(4) 0.0421(5) Uani 1 1 d . . .
H13A H 0.3607 0.4645 0.6059 0.063 Uiso 1 1 calc R . .
H13B H 0.3025 0.4106 0.7399 0.063 Uiso 1 1 calc R . .
H13C H 0.2924 0.5202 0.6708 0.063 Uiso 1 1 calc R . .
C14 C 0.17018(11) 0.40275(19) 0.6443(4) 0.0456(5) Uani 1 1 d . . .
H14A H 0.193 0.3415 0.6724 0.068 Uiso 1 1 calc R . .
H14B H 0.1208 0.3925 0.6367 0.068 Uiso 1 1 calc R . .
H14C H 0.1805 0.4478 0.7607 0.068 Uiso 1 1 calc R . .
C15 C 0.47873(10) 0.34682(17) 0.2066(4) 0.0459(6) Uani 1 1 d . . .
H15A H 0.4919 0.3929 0.3203 0.055 Uiso 1 1 calc R . .
H15B H 0.4902 0.2818 0.2593 0.055 Uiso 1 1 calc R . .
C16 C 0.52216(11) 0.36727(18) 0.0067(6) 0.0551(7) Uani 1 1 d . . .
H16A H 0.5707 0.3719 0.0494 0.066 Uiso 1 1 calc R . .
H16B H 0.5085 0.4297 -0.0555 0.066 Uiso 1 1 calc R . .
N1 N 0.28840(8) 0.32072(11) 0.3783(3) 0.0332(4) Uani 1 1 d . . .
N2 N 0.16057(8) 0.40147(11) 0.2328(3) 0.0325(4) Uani 1 1 d . . .
N3 N 0.18478(8) 0.55187(12) 0.4208(3) 0.0370(4) Uani 1 1 d . . .
N4 N 0.30994(8) 0.48203(10) 0.2293(3) 0.0296(3) Uani 1 1 d . . .
O1 O 0.40913(8) 0.51696(10) 0.0463(3) 0.0458(4) Uani 1 1 d . . .
Cl1 Cl 0.51283(3) 0.27366(5) -0.19792(14) 0.0641(2) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 N1 1.471(3) . ?
C1 C2 1.498(3) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C2 N2 1.454(2) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 N2 1.473(2) . ?
C3 C4 1.516(3) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4 C5 1.514(4) . ?
C4 H4A 0.97 . ?
C4 H4B 0.97 . ?
C5 N3 1.484(3) . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C6 N3 1.466(3) . ?
C6 C7 1.500(3) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 N4 1.467(2) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 O1 1.227(2) . ?
C8 N4 1.366(2) . ?
C8 C9 1.524(2) . ?
C9 C10 1.530(3) . ?
C9 C15 1.543(3) . ?
C9 H9 0.98 . ?
C10 N1 1.456(2) . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 N1 1.454(2) . ?
C11 N4 1.497(2) . ?
C11 C13 1.539(3) . ?
C11 C12 1.581(3) . ?
C12 N3 1.475(3) . ?
C12 N2 1.478(2) . ?
C12 C14 1.544(3) . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C15 C16 1.502(4) . ?
C15 H15A 0.97 . ?
C15 H15B 0.97 . ?
C16 Cl1 1.795(3) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?

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
N1 C1 C2 110.85(18) . . ?
N1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.1 . . ?
N2 C2 C1 109.78(15) . . ?
N2 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
N2 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
N2 C3 C4 111.95(16) . . ?
N2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
N2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 111.1(2) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108 . . ?
N3 C5 C4 112.27(19) . . ?
N3 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
N3 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
N3 C6 C7 111.09(17) . . ?
N3 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
N3 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108 . . ?
N4 C7 C6 109.72(15) . . ?
N4 C7 H7A 109.7 . . ?
C6 C7 H7A 109.7 . . ?
N4 C7 H7B 109.7 . . ?
C6 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
O1 C8 N4 121.21(17) . . ?
O1 C8 C9 120.17(18) . . ?
N4 C8 C9 118.49(15) . . ?
C8 C9 C10 112.94(16) . . ?
C8 C9 C15 112.09(16) . . ?
C10 C9 C15 110.20(17) . . ?
C8 C9 H9 107.1 . . ?
C10 C9 H9 107.1 . . ?
C15 C9 H9 107.1 . . ?
N1 C10 C9 113.51(16) . . ?
N1 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
N1 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N1 C11 N4 110.14(15) . . ?
N1 C11 C13 110.16(16) . . ?
N4 C11 C13 107.36(14) . . ?
N1 C11 C12 108.95(13) . . ?
N4 C11 C12 111.06(14) . . ?
C13 C11 C12 109.15(16) . . ?
N3 C12 N2 108.60(16) . . ?
N3 C12 C14 109.53(17) . . ?
N2 C12 C14 112.48(15) . . ?
N3 C12 C11 108.62(14) . . ?
N2 C12 C11 110.34(15) . . ?
C14 C12 C11 107.19(16) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C9 116.4(2) . . ?
C16 C15 H15A 108.2 . . ?
C9 C15 H15A 108.2 . . ?
C16 C15 H15B 108.2 . . ?
C9 C15 H15B 108.2 . . ?
H15A C15 H15B 107.3 . . ?
C15 C16 Cl1 111.98(16) . . ?
C15 C16 H16A 109.2 . . ?
Cl1 C16 H16A 109.2 . . ?
C15 C16 H16B 109.2 . . ?
Cl1 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C11 N1 C10 111.11(14) . . ?
C11 N1 C1 113.93(15) . . ?
C10 N1 C1 110.37(17) . . ?
C2 N2 C3 109.90(15) . . ?
C2 N2 C12 112.82(15) . . ?
C3 N2 C12 113.14(16) . . ?
C6 N3 C12 112.13(16) . . ?
C6 N3 C5 109.79(19) . . ?
C12 N3 C5 110.50(15) . . ?
C8 N4 C7 115.68(14) . . ?
C8 N4 C11 121.24(14) . . ?
C7 N4 C11 116.20(16) . . ?

#----------------------------------------------------------------------------#
#                   SHELXL.RES FILE                                          #
#----------------------------------------------------------------------------#

_iucr_refine_instruction_details 
;
TITL NC526-a at 297 K in Pna2(1)  (#33 in standard setting)
CELL  0.71073  19.2249  13.6646   6.0897   90.000   90.000   90.000
ZERR     4.00   0.0008   0.0005   0.0002    0.000    0.000    0.000
LATT  -1
SYMM  - X, - Y, 1/2 + Z
SYMM  1/2 - X, 1/2 + Y, 1/2 + Z
SYMM  1/2 + X, 1/2 - Y,   Z
SFAC  C    H    N    O    CL
UNIT  64   108  16   4    4
MERG   2
OMIT     0   2   0
SHEL   13 0.75
FMAP   2
PLAN   25
SIZE     0.07   0.28   0.35
ACTA
BOND   $H
L.S.   4
TEMP    24.00
WGHT    0.065600
FVAR       1.20971
MOLE    1
C1    1    0.250844    0.280113    0.188524    11.00000    0.04634    0.02507 =
         0.04006   -0.00229   -0.00063   -0.00311
AFIX  23
H1A   2    0.259774    0.210391    0.178444    11.00000   -1.20000
H1B   2    0.267667    0.310616    0.054859    11.00000   -1.20000
AFIX   0
C2    1    0.174165    0.297277    0.209801    11.00000    0.04438    0.03012 =
         0.04045   -0.00527   -0.00232   -0.00817
AFIX  23
H2A   2    0.150460    0.272357    0.080787    11.00000   -1.20000
H2B   2    0.156503    0.262670    0.337208    11.00000   -1.20000
AFIX   0
C3    1    0.085037    0.419466    0.231954    11.00000    0.03469    0.04864 =
         0.05371   -0.00860   -0.00714   -0.00371
AFIX  23
H3A   2    0.063828    0.384397    0.353183    11.00000   -1.20000
H3B   2    0.065318    0.394343    0.096609    11.00000   -1.20000
AFIX   0
C4    1    0.068117    0.527490    0.252059    11.00000    0.03500    0.05611 =
         0.07374   -0.01197   -0.00884    0.00647
AFIX  23
H4A   2    0.078731    0.560114    0.114617    11.00000   -1.20000
H4B   2    0.018802    0.535396    0.280683    11.00000   -1.20000
AFIX   0
C5    1    0.109399    0.574395    0.435684    11.00000    0.03963    0.04733 =
         0.07020   -0.01873    0.00092    0.00936
AFIX  23
H5A   2    0.102965    0.644761    0.430328    11.00000   -1.20000
H5B   2    0.091738    0.551339    0.575636    11.00000   -1.20000
AFIX   0
C6    1    0.214261    0.597794    0.224177    11.00000    0.04569    0.02497 =
         0.04765   -0.00023   -0.00664    0.00324
AFIX  23
H6A   2    0.202609    0.666861    0.223170    11.00000   -1.20000
H6B   2    0.194076    0.568104    0.094282    11.00000   -1.20000
AFIX   0
C7    1    0.291842    0.586165    0.217850    11.00000    0.04343    0.02481 =
         0.04340    0.00279    0.00026   -0.00256
AFIX  23
H7A   2    0.309990    0.614154    0.083146    11.00000   -1.20000
H7B   2    0.312591    0.620682    0.340659    11.00000   -1.20000
AFIX   0
C8    1    0.373959    0.457653    0.148927    11.00000    0.03383    0.03225 =
         0.02475    0.00145   -0.00477   -0.00406
C9    1    0.399145    0.352586    0.176136    11.00000    0.03153    0.03361 =
         0.03547    0.00187   -0.00259    0.00136
AFIX  13
H9    2    0.388004    0.317917    0.039722    11.00000   -1.20000
AFIX   0
C10   1    0.362294    0.298362    0.362570    11.00000    0.04218    0.03397 =
         0.04190    0.00943   -0.00198    0.00603
AFIX  23
H10A  2    0.367869    0.228491    0.340627    11.00000   -1.20000
H10B  2    0.384533    0.315214    0.500456    11.00000   -1.20000
AFIX   0
C11   1    0.277116    0.424894    0.411565    11.00000    0.03376    0.03034 =
         0.02349    0.00131   -0.00394   -0.00207
C12   1    0.196253    0.445141    0.424132    11.00000    0.03415    0.03262 =
         0.02661   -0.00413   -0.00082   -0.00249
C13   1    0.311403    0.458203    0.627350    11.00000    0.04316    0.05452 =
         0.02850   -0.00119   -0.00803   -0.00467
AFIX 137
H13A  2    0.360670    0.464542    0.605946    11.00000   -1.50000
H13B  2    0.302531    0.410629    0.739916    11.00000   -1.50000
H13C  2    0.292396    0.520217    0.670793    11.00000   -1.50000
AFIX   0
C14   1    0.170183    0.402745    0.644337    11.00000    0.04406    0.06123 =
         0.03143   -0.00016    0.00677   -0.00554
AFIX 137
H14A  2    0.192999    0.341520    0.672425    11.00000   -1.50000
H14B  2    0.120838    0.392524    0.636722    11.00000   -1.50000
H14C  2    0.180506    0.447838    0.760747    11.00000   -1.50000
AFIX   0
C15   1    0.478730    0.346816    0.206565    11.00000    0.03542    0.04641 =
         0.05593   -0.00240   -0.00928    0.00488
AFIX  23
H15A  2    0.491947    0.392899    0.320313    11.00000   -1.20000
H15B  2    0.490217    0.281818    0.259337    11.00000   -1.20000
AFIX   0
C16   1    0.522163    0.367273    0.006653    11.00000    0.03418    0.04423 =
         0.08686    0.00779    0.00890    0.00073
AFIX  23
H16A  2    0.570658    0.371939    0.049361    11.00000   -1.20000
H16B  2    0.508477    0.429731   -0.055502    11.00000   -1.20000
AFIX   0
N1    3    0.288400    0.320725    0.378259    11.00000    0.03761    0.02856 =
         0.03341    0.00632   -0.00151   -0.00119
N2    3    0.160568    0.401468    0.232814    11.00000    0.03438    0.03077 =
         0.03231   -0.00349   -0.00606   -0.00218
N3    3    0.184785    0.551868    0.420810    11.00000    0.03578    0.03538 =
         0.03987   -0.01055   -0.00001    0.00135
N4    3    0.309942    0.482033    0.229319    11.00000    0.03456    0.02413 =
         0.03016    0.00205    0.00037   -0.00071
O1    4    0.409130    0.516964    0.046302    11.00000    0.04214    0.04058 =
         0.05466    0.01126    0.00779   -0.00731
CL1   5    0.512826    0.273663   -0.197925    11.00000    0.06105    0.07464 =
         0.05664    0.00480    0.00947    0.00493
HKLF    4  1.0  0.00  0.00  1.00  0.00 -1.00  0.00  1.00  0.00  0.00
 
REM  NC526-a at 297 K in Pna2(1)  (#33 in standard setting)
REM R1 =  0.0428 for   2434 Fo > 4sig(Fo)  and  0.0533 for all   2980 data
REM    201 parameters refined using      1 restraints
 
END
 
WGHT      0.0655      0.0000
REM Highest difference peak  0.314,  deepest hole -0.136,  1-sigma level  0.054
Q1    1   0.5073  0.3398 -0.1970  11.00000  0.05    0.31
Q2    1   0.1489  0.5618  0.4219  11.00000  0.05    0.30
Q3    1   0.2355  0.4385  0.4200  11.00000  0.05    0.26
Q4    1   0.1802  0.4234  0.3154  11.00000  0.05    0.26
Q5    1   0.2959  0.4422  0.5083  11.00000  0.05    0.25
Q6    1   0.2994  0.5240  0.2227  11.00000  0.05    0.25
Q7    1   0.2708  0.3008  0.2857  11.00000  0.05    0.24
Q8    1   0.3381  0.4758  0.2140  11.00000  0.05    0.24
Q9    1   0.1816  0.4319  0.5264  11.00000  0.05    0.23
Q10   1   0.4355  0.3498  0.1927  11.00000  0.05    0.23
Q11   1   0.2975  0.4500  0.3158  11.00000  0.05    0.23
Q12   1   0.1232  0.4065  0.2493  11.00000  0.05    0.23
Q13   1   0.1870  0.4946  0.4200  11.00000  0.05    0.23
Q14   1   0.0749  0.4755  0.2206  11.00000  0.05    0.22
Q15   1   0.3341  0.4682  0.1656  11.00000  0.05    0.22
Q16   1   0.4636  0.2706 -0.2018  11.00000  0.05    0.22
Q17   1   0.1685  0.3678  0.2206  11.00000  0.05    0.22
Q18   1   0.2531  0.5924  0.2152  11.00000  0.05    0.21
Q19   1   0.3204  0.3137  0.3818  11.00000  0.05    0.21
Q20   1   0.3880  0.3973  0.1528  11.00000  0.05    0.21
Q21   1   0.3819  0.3450  0.2869  11.00000  0.05    0.21
Q22   1   0.1952  0.5745  0.3325  11.00000  0.05    0.21
Q23   1   0.2136  0.2896  0.2247  11.00000  0.05    0.20
Q24   1   0.2833  0.3545  0.4168  11.00000  0.05    0.19
Q25   1   0.1699  0.4228  0.1229  11.00000  0.05    0.18

;

# The following lines are used to test the character set of files sent by
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# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
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# END of CIF
