# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_compound_10e
_database_code_depnum_ccdc_archive 'CCDC 1045024'
_audit_update_record             
;
2017-09-21 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;

_audit_creation_date             2014-10-15T15:48:08-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_name_common            rotaxane
_chemical_formula_moiety         'C31 H33 Cl N5 O4'
_chemical_formula_sum            'C31 H33 Cl N5 O4'
_chemical_formula_weight         575.07
_chemical_melting_point          'up 523K'

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6985(7)
_cell_length_b                   11.4602(9)
_cell_length_c                   14.9575(12)
_cell_angle_alpha                80.519(4)
_cell_angle_beta                 73.258(4)
_cell_angle_gamma                76.892(4)
_cell_volume                     1541.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.443
_cell_measurement_theta_max      26.42

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.302
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.122
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             606


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

_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'XPREP (Bruker, 2006)'
_exptl_absorpt_special_details   
;
 XPREP (Bruker, 2006) was used to perform the Gaussian absorption
        correction based on the face-indexed crystal size
;
_exptl_absorpt_correction_T_min  0.6432
_exptl_absorpt_correction_T_max  0.9184

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

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_number            43020
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.83
_diffrn_reflns_theta_max         27.24
_diffrn_reflns_theta_full        27.24
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_reflns_number_total             6748
_reflns_number_gt                5116
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   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)+(0.0876P)²+0.1699P] 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       none
_refine_ls_number_reflns         6748
_refine_ls_number_parameters     372
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1495
_refine_ls_wR_factor_gt          0.1417
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.154
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
#                   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
C2 C 0.52034(19) 0.31471(16) 0.61987(13) 0.0228(4) Uani 1 1 d . . .
C4 C 0.6877(2) 0.41948(17) 0.49326(15) 0.0274(4) Uani 1 1 d . . .
H4A H 0.6541 0.481 0.5362 0.033 Uiso 1 1 calc R . .
H4B H 0.6617 0.4543 0.4353 0.033 Uiso 1 1 calc R . .
C5 C 0.85274(19) 0.38293(15) 0.47313(14) 0.0231(4) Uani 1 1 d . . .
C6 C 0.9386(2) 0.36977(17) 0.38190(14) 0.0256(4) Uani 1 1 d . . .
H6 H 0.8941 0.3828 0.3328 0.031 Uiso 1 1 calc R . .
C7 C 1.0898(2) 0.33734(17) 0.36356(14) 0.0265(4) Uani 1 1 d . . .
H7 H 1.1457 0.3285 0.3022 0.032 Uiso 1 1 calc R . .
C8 C 1.15915(19) 0.31787(16) 0.43548(14) 0.0241(4) Uani 1 1 d . . .
C9 C 1.0729(2) 0.33113(17) 0.52707(14) 0.0269(4) Uani 1 1 d . . .
H9 H 1.1172 0.3182 0.5762 0.032 Uiso 1 1 calc R . .
C10 C 0.9217(2) 0.36346(17) 0.54518(14) 0.0267(4) Uani 1 1 d . . .
H10 H 0.8656 0.3722 0.6065 0.032 Uiso 1 1 calc R . .
C11 C 1.3243(2) 0.28690(17) 0.41608(16) 0.0288(4) Uani 1 1 d . . .
H11A H 1.367 0.3414 0.3639 0.035 Uiso 1 1 calc R . .
H11B H 1.3526 0.2983 0.4707 0.035 Uiso 1 1 calc R . .
C13 C 1.52591(19) 0.11789(17) 0.38276(13) 0.0224(4) Uani 1 1 d . . .
C14 C 1.58303(19) -0.00733(17) 0.35604(13) 0.0233(4) Uani 1 1 d . . .
C15 C 1.7289(2) -0.03342(19) 0.30408(15) 0.0304(4) Uani 1 1 d . . .
H15 H 1.786 0.0257 0.2891 0.037 Uiso 1 1 calc R . .
C16 C 1.7892(2) -0.14675(19) 0.27463(15) 0.0342(5) Uani 1 1 d . . .
H16 H 1.8861 -0.1632 0.2391 0.041 Uiso 1 1 calc R . .
C17 C 1.7055(2) -0.23536(18) 0.29803(14) 0.0276(4) Uani 1 1 d . . .
H17 H 1.7455 -0.3108 0.2768 0.033 Uiso 1 1 calc R . .
C18 C 1.56155(19) -0.21261(16) 0.35313(12) 0.0220(4) Uani 1 1 d . . .
C19 C 1.49996(19) -0.09779(16) 0.38162(12) 0.0214(4) Uani 1 1 d . . .
H19 H 1.4034 -0.0817 0.4177 0.026 Uiso 1 1 calc R . .
C20 C 0.9660(2) 0.01228(17) 0.45851(14) 0.0287(4) Uani 1 1 d . . .
C22 C 1.16509(18) -0.02982(16) 0.31707(12) 0.0206(4) Uani 1 1 d . . .
C23 C 1.24316(19) -0.11316(16) 0.24477(13) 0.0226(4) Uani 1 1 d . . .
C24 C 1.38165(19) -0.10883(16) 0.18385(13) 0.0225(4) Uani 1 1 d . . .
H24 H 1.4407 -0.0534 0.1796 0.027 Uiso 1 1 calc R . .
C25 C 1.41214(19) -0.20375(17) 0.13168(13) 0.0235(4) Uani 1 1 d . . .
C251 C 1.55393(19) -0.24299(17) 0.06257(13) 0.0240(4) Uani 1 1 d . . .
C252 C 1.5855(2) -0.18288(18) -0.02727(14) 0.0299(4) Uani 1 1 d . . .
H252 H 1.5138 -0.1234 -0.0463 0.036 Uiso 1 1 calc R . .
C253 C 1.7235(2) -0.21078(19) -0.08918(14) 0.0325(5) Uani 1 1 d . . .
H253 H 1.7442 -0.1712 -0.1496 0.039 Uiso 1 1 calc R . .
C254 C 1.8291(2) -0.29870(19) -0.05888(14) 0.0298(4) Uani 1 1 d . . .
C255 C 1.8002(2) -0.35956(18) 0.02963(14) 0.0288(4) Uani 1 1 d . . .
H255 H 1.8725 -0.4187 0.0484 0.035 Uiso 1 1 calc R . .
C256 C 1.6618(2) -0.33173(18) 0.09088(13) 0.0261(4) Uani 1 1 d . . .
H256 H 1.6413 -0.3725 0.1509 0.031 Uiso 1 1 calc R . .
C261 C 1.2675(2) -0.36786(18) 0.12928(15) 0.0308(5) Uani 1 1 d . . .
C262 C 1.3546(2) -0.47969(19) 0.17244(18) 0.0412(5) Uani 1 1 d . . .
H26A H 1.4572 -0.4768 0.1512 0.062 Uiso 1 1 calc R . .
H26B H 1.338 -0.5504 0.1537 0.062 Uiso 1 1 calc R . .
H26C H 1.3235 -0.4823 0.2396 0.062 Uiso 1 1 calc R . .
C263 C 1.3152(3) -0.3592(2) 0.02252(17) 0.0468(6) Uani 1 1 d . . .
H26G H 1.4177 -0.3562 0.0011 0.07 Uiso 1 1 calc R . .
H26H H 1.2599 -0.2875 -0.0028 0.07 Uiso 1 1 calc R . .
H26I H 1.298 -0.4285 0.002 0.07 Uiso 1 1 calc R . .
C264 C 1.1046(2) -0.3716(2) 0.16286(19) 0.0443(6) Uani 1 1 d . . .
H26D H 1.0741 -0.3769 0.2302 0.066 Uiso 1 1 calc R . .
H26E H 1.0869 -0.4407 0.1423 0.066 Uiso 1 1 calc R . .
H26F H 1.05 -0.2997 0.1373 0.066 Uiso 1 1 calc R . .
N3 N 0.61296(16) 0.31856(14) 0.53385(11) 0.0248(3) Uani 1 1 d . . .
H3 H 0.6289 0.2593 0.5014 0.03 Uiso 1 1 calc R . .
N12 N 1.38281(16) 0.16281(14) 0.39376(11) 0.0239(3) Uani 1 1 d . . .
H12 H 1.3256 0.1189 0.3877 0.029 Uiso 1 1 calc R . .
N21 N 1.05023(17) -0.06200(14) 0.38363(11) 0.0277(4) Uani 1 1 d . . .
H21 H 1.0254 -0.1289 0.3821 0.033 Uiso 1 1 calc R . .
N26 N 1.29276(17) -0.25868(14) 0.16160(11) 0.0256(4) Uani 1 1 d . . .
N27 N 1.18899(17) -0.20412(14) 0.23149(11) 0.0272(4) Uani 1 1 d . . .
O1 O 1.50267(16) -0.39277(12) 0.32664(10) 0.0311(3) Uani 1 1 d . . .
O2 O 1.61133(14) 0.17754(12) 0.39298(10) 0.0295(3) Uani 1 1 d . . .
O3 O 1.20752(13) 0.06442(11) 0.31526(9) 0.0246(3) Uani 1 1 d . . .
O5 O 1.6771(2) -0.6085(2) 0.25330(17) 0.0816(7) Uani 1 1 d . . .
Cl1 Cl 2.00447(5) -0.33119(6) -0.13349(4) 0.04379(18) Uani 1 1 d . . .
H20A H 0.9566 0.101 0.4337 0.05 Uiso 1 1 d D . .
H20B H 0.8654 -0.0024 0.4808 0.05 Uiso 1 1 d D . .
H5A H 1.6055 -0.5357 0.2923 0.05 Uiso 1 1 d D . .
H5B H 1.6221 -0.6746 0.3024 0.05 Uiso 1 1 d 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
C2 O1 1.238(2) 2_756 ?
C2 N3 1.341(2) . ?
C2 C18 1.498(3) 2_756 ?
C4 N3 1.459(2) . ?
C4 C5 1.512(2) . ?
C5 C10 1.388(3) . ?
C5 C6 1.391(3) . ?
C6 C7 1.386(3) . ?
C7 C8 1.389(3) . ?
C8 C9 1.397(3) . ?
C8 C11 1.512(2) . ?
C9 C10 1.385(3) . ?
C11 N12 1.462(2) . ?
C13 O2 1.241(2) . ?
C13 N12 1.338(2) . ?
C13 C14 1.492(3) . ?
C14 C19 1.393(3) . ?
C14 C15 1.395(2) . ?
C15 C16 1.385(3) . ?
C16 C17 1.381(3) . ?
C17 C18 1.392(2) . ?
C18 C19 1.397(3) . ?
C18 C2 1.498(3) 2_756 ?
C20 N21 1.455(2) . ?
C20 C20 1.525(4) 2_756 ?
C22 O3 1.234(2) . ?
C22 N21 1.340(2) . ?
C22 C23 1.482(2) . ?
C23 N27 1.334(2) . ?
C23 C24 1.395(2) . ?
C24 C25 1.371(3) . ?
C25 N26 1.370(2) . ?
C25 C251 1.488(2) . ?
C251 C252 1.388(3) . ?
C251 C256 1.393(3) . ?
C252 C253 1.393(2) . ?
C253 C254 1.385(3) . ?
C254 C255 1.374(3) . ?
C254 Cl1 1.7418(19) . ?
C255 C256 1.392(2) . ?
C261 N26 1.505(3) . ?
C261 C263 1.522(3) . ?
C261 C264 1.522(3) . ?
C261 C262 1.524(3) . ?
N26 N27 1.349(2) . ?
O1 C2 1.238(2) 2_756 ?

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 C2 N3 123.01(17) 2_756 . ?
O1 C2 C18 120.89(16) 2_756 2_756 ?
N3 C2 C18 116.03(15) . 2_756 ?
N3 C4 C5 112.70(15) . . ?
C10 C5 C6 118.69(17) . . ?
C10 C5 C4 120.65(17) . . ?
C6 C5 C4 120.66(18) . . ?
C7 C6 C5 120.53(18) . . ?
C6 C7 C8 120.92(18) . . ?
C7 C8 C9 118.50(17) . . ?
C7 C8 C11 121.50(18) . . ?
C9 C8 C11 119.97(18) . . ?
C10 C9 C8 120.43(18) . . ?
C9 C10 C5 120.92(18) . . ?
N12 C11 C8 112.17(15) . . ?
O2 C13 N12 122.05(17) . . ?
O2 C13 C14 119.74(16) . . ?
N12 C13 C14 118.20(16) . . ?
C19 C14 C15 119.43(17) . . ?
C19 C14 C13 123.65(16) . . ?
C15 C14 C13 116.90(17) . . ?
C16 C15 C14 120.47(18) . . ?
C17 C16 C15 119.94(17) . . ?
C16 C17 C18 120.46(17) . . ?
C17 C18 C19 119.58(17) . . ?
C17 C18 C2 117.63(16) . 2_756 ?
C19 C18 C2 122.79(16) . 2_756 ?
C14 C19 C18 120.04(16) . . ?
N21 C20 C20 112.09(19) . 2_756 ?
O3 C22 N21 122.39(16) . . ?
O3 C22 C23 120.10(15) . . ?
N21 C22 C23 117.50(16) . . ?
N27 C23 C24 111.56(16) . . ?
N27 C23 C22 123.29(16) . . ?
C24 C23 C22 125.13(17) . . ?
C25 C24 C23 105.26(16) . . ?
N26 C25 C24 106.57(15) . . ?
N26 C25 C251 127.95(16) . . ?
C24 C25 C251 125.28(17) . . ?
C252 C251 C256 119.45(16) . . ?
C252 C251 C25 120.31(16) . . ?
C256 C251 C25 119.88(17) . . ?
C251 C252 C253 120.68(18) . . ?
C254 C253 C252 118.63(18) . . ?
C255 C254 C253 121.71(17) . . ?
C255 C254 Cl1 118.80(15) . . ?
C253 C254 Cl1 119.47(15) . . ?
C254 C255 C256 119.32(18) . . ?
C255 C256 C251 120.19(18) . . ?
N26 C261 C263 109.58(17) . . ?
N26 C261 C264 108.67(15) . . ?
C263 C261 C264 109.2(2) . . ?
N26 C261 C262 108.33(17) . . ?
C263 C261 C262 111.16(18) . . ?
C264 C261 C262 109.81(19) . . ?
C2 N3 C4 122.52(16) . . ?
C13 N12 C11 119.61(15) . . ?
C22 N21 C20 122.31(16) . . ?
N27 N26 C25 111.53(15) . . ?
N27 N26 C261 119.15(15) . . ?
C25 N26 C261 129.30(15) . . ?
C23 N27 N26 105.07(14) . . ?

####################################################################### 
# 
# 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_mo_compound_9c
_database_code_depnum_ccdc_archive 'CCDC 1459084'
_audit_update_record             
;
2017-09-21 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;

_audit_creation_date             2016-03-07T14:23:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
'1,2-bis(aminocarbonyl-(5'-phenyl)-(1'-tert-butyl)-1H-pyrazole-3'-il)-ethane'
;
_chemical_name_common            'thread 1,3-pyrazole'
_chemical_formula_moiety         'C30 H36 N6 O2'
_chemical_formula_sum            'C30 H36 N6 O2'
_chemical_formula_weight         512.65
_chemical_melting_point          none

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.9687(3)
_cell_length_b                   12.1818(6)
_cell_length_c                   16.6042(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.584(2)
_cell_angle_gamma                90
_cell_volume                     1389.88(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9017
_cell_measurement_theta_min      2.488
_cell_measurement_theta_max      29.595

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             548

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

_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   
;
'SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
absorption correction based on the indexed faces of the cystal.'
;
_exptl_absorpt_correction_T_min  0.7255
_exptl_absorpt_correction_T_max  0.7461

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

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.099
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_number            95541
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         30.1
_diffrn_reflns_theta_full        30.1
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_reflns_number_total             4058
_reflns_number_gt                3185
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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)+(0.0801P)²+0.2968P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         4058
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.066
_refine_ls_R_factor_gt           0.0506
_refine_ls_wR_factor_ref         0.1538
_refine_ls_wR_factor_gt          0.1384
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.043

#----------------------------------------------------------------------------#
#                   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
N1 N 0.32784(14) 0.74204(8) 0.35403(6) 0.0338(2) Uani 1 1 d . . .
O1 O 0.63532(16) 0.41651(8) 0.38850(7) 0.0570(3) Uani 1 1 d . . .
N2 N 0.47930(14) 0.69194(8) 0.40101(6) 0.0363(2) Uani 1 1 d . . .
N32 N 0.74453(15) 0.54977(10) 0.47883(7) 0.0446(3) Uani 1 1 d . . .
H32 H 0.7214 0.6141 0.4964 0.054 Uiso 1 1 calc R . .
C5 C 0.22460(15) 0.66978(9) 0.30031(6) 0.0317(2) Uani 1 1 d . . .
C51 C 0.04546(16) 0.69352(9) 0.24170(7) 0.0326(2) Uani 1 1 d . . .
C4 C 0.31807(16) 0.57024(10) 0.31272(7) 0.0356(2) Uani 1 1 d . . .
H4 H 0.2848 0.5049 0.2849 0.043 Uiso 1 1 calc R . .
C3 C 0.47344(16) 0.58833(9) 0.37595(7) 0.0335(2) Uani 1 1 d . . .
C31 C 0.62396(16) 0.50941(10) 0.41442(8) 0.0372(3) Uani 1 1 d . . .
C56 C -0.13262(18) 0.70767(11) 0.26764(8) 0.0410(3) Uani 1 1 d . . .
H56 H -0.1399 0.7032 0.323 0.049 Uiso 1 1 calc R . .
C52 C 0.0515(2) 0.69619(12) 0.15889(8) 0.0451(3) Uani 1 1 d . . .
H52 H 0.1691 0.6856 0.1405 0.054 Uiso 1 1 calc R . .
C33 C 0.91203(18) 0.49016(13) 0.52036(9) 0.0459(3) Uani 1 1 d . . .
C11 C 0.2999(2) 0.86144(10) 0.37027(8) 0.0416(3) Uani 1 1 d . . .
C55 C -0.29906(18) 0.72834(12) 0.21161(10) 0.0475(3) Uani 1 1 d . . .
H55 H -0.4169 0.7399 0.2296 0.057 Uiso 1 1 calc R . .
C54 C -0.2913(2) 0.73192(12) 0.12947(9) 0.0504(3) Uani 1 1 d . . .
H54 H -0.4033 0.746 0.0919 0.06 Uiso 1 1 calc R . .
C53 C -0.1169(2) 0.71462(14) 0.10314(9) 0.0536(4) Uani 1 1 d . . .
H53 H -0.1118 0.7153 0.0475 0.064 Uiso 1 1 calc R . .
C13 C 0.1941(3) 0.91873(13) 0.29504(11) 0.0702(5) Uani 1 1 d . . .
H13A H 0.0676 0.8865 0.2795 0.105 Uiso 1 1 calc R . .
H13B H 0.267 0.9108 0.2512 0.105 Uiso 1 1 calc R . .
H13C H 0.1804 0.9953 0.3067 0.105 Uiso 1 1 calc R . .
C12 C 0.4997(3) 0.91368(14) 0.39333(14) 0.0724(5) Uani 1 1 d . . .
H12A H 0.5695 0.9077 0.3483 0.109 Uiso 1 1 calc R . .
H12B H 0.5707 0.8766 0.44 0.109 Uiso 1 1 calc R . .
H12C H 0.4851 0.9897 0.4063 0.109 Uiso 1 1 calc R . .
C14 C 0.1885(4) 0.86905(17) 0.44073(13) 0.0792(6) Uani 1 1 d . . .
H14A H 0.0626 0.836 0.4254 0.119 Uiso 1 1 calc R . .
H14B H 0.1733 0.9448 0.4544 0.119 Uiso 1 1 calc R . .
H14C H 0.2588 0.8312 0.4872 0.119 Uiso 1 1 calc R . .
H33A H 0.940(3) 0.5130(15) 0.5774(12) 0.058(5) Uiso 1 1 d . . .
H33B H 0.883(3) 0.4122(17) 0.5219(11) 0.066(5) 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
N1 N2 1.3494(13) . ?
N1 C5 1.3691(14) . ?
N1 C11 1.4980(15) . ?
O1 C31 1.2180(16) . ?
N2 C3 1.3275(15) . ?
N32 C31 1.3389(17) . ?
N32 C33 1.4481(15) . ?
N32 H32 0.86 . ?
C5 C4 1.3756(16) . ?
C5 C51 1.4780(15) . ?
C51 C52 1.3830(17) . ?
C51 C56 1.3904(16) . ?
C4 C3 1.3944(16) . ?
C4 H4 0.93 . ?
C3 C31 1.4864(15) . ?
C56 C55 1.3838(18) . ?
C56 H56 0.93 . ?
C52 C53 1.3864(19) . ?
C52 H52 0.93 . ?
C33 C33 1.515(3) 3_766 ?
C33 H33A 0.976(19) . ?
C33 H33B 0.97(2) . ?
C11 C14 1.511(2) . ?
C11 C13 1.511(2) . ?
C11 C12 1.521(2) . ?
C55 C54 1.375(2) . ?
C55 H55 0.93 . ?
C54 C53 1.375(2) . ?
C54 H54 0.93 . ?
C53 H53 0.93 . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?

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
N2 N1 C5 111.19(9) . . ?
N2 N1 C11 116.60(9) . . ?
C5 N1 C11 132.19(10) . . ?
C3 N2 N1 105.57(9) . . ?
C31 N32 C33 123.03(12) . . ?
C31 N32 H32 118.5 . . ?
C33 N32 H32 118.5 . . ?
N1 C5 C4 106.54(10) . . ?
N1 C5 C51 126.71(10) . . ?
C4 C5 C51 126.74(10) . . ?
C52 C51 C56 118.77(11) . . ?
C52 C51 C5 119.81(10) . . ?
C56 C51 C5 121.33(10) . . ?
C5 C4 C3 105.22(10) . . ?
C5 C4 H4 127.4 . . ?
C3 C4 H4 127.4 . . ?
N2 C3 C4 111.45(10) . . ?
N2 C3 C31 119.84(10) . . ?
C4 C3 C31 128.70(11) . . ?
O1 C31 N32 123.67(12) . . ?
O1 C31 C3 122.13(12) . . ?
N32 C31 C3 114.20(11) . . ?
C55 C56 C51 120.38(12) . . ?
C55 C56 H56 119.8 . . ?
C51 C56 H56 119.8 . . ?
C51 C52 C53 120.35(12) . . ?
C51 C52 H52 119.8 . . ?
C53 C52 H52 119.8 . . ?
N32 C33 C33 110.88(14) . 3_766 ?
N32 C33 H33A 109.4(11) . . ?
C33 C33 H33A 110.1(11) 3_766 . ?
N32 C33 H33B 110.3(11) . . ?
C33 C33 H33B 110.8(11) 3_766 . ?
H33A C33 H33B 105.2(15) . . ?
N1 C11 C14 107.34(12) . . ?
N1 C11 C13 111.09(11) . . ?
C14 C11 C13 111.64(15) . . ?
N1 C11 C12 108.09(11) . . ?
C14 C11 C12 110.26(15) . . ?
C13 C11 C12 108.37(14) . . ?
C54 C55 C56 120.39(12) . . ?
C54 C55 H55 119.8 . . ?
C56 C55 H55 119.8 . . ?
C55 C54 C53 119.58(12) . . ?
C55 C54 H54 120.2 . . ?
C53 C54 H54 120.2 . . ?
C54 C53 C52 120.48(13) . . ?
C54 C53 H53 119.8 . . ?
C52 C53 H53 119.8 . . ?
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 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

# 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_compound_8e
_database_code_depnum_ccdc_archive 'CCDC 1498649'
_audit_update_record             
;
2017-09-21 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;

_audit_creation_date             2016-12-13T22:36:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
"'1,2-bis(aminocarbonyl-(3'-(4"-chlorophenyl)-1'-        (1',1'-tert-butyl)-1H-pyrazole-5'-il))-ethane'"
_chemical_name_common            1,5-thread-p-Ph-Cl
_chemical_formula_moiety         'C15 H17 Cl N3 O'
_chemical_formula_sum            'C15 H17 Cl N3 O'
_chemical_formula_weight         290.77
_chemical_melting_point          none

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  -C2yc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   26.6417(8)
_cell_length_b                   11.3041(3)
_cell_length_c                   9.7939(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.318(2)
_cell_angle_gamma                90
_cell_volume                     2948.76(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.8435
_cell_measurement_theta_max      27.393

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.77
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.44
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.31
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1224

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

_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   
;
'SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
absorption correction based on the indexed faces of the cystal.'
;
_exptl_absorpt_correction_T_min  0.9460
_exptl_absorpt_correction_T_max  1.0000

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_number            40005
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_full        27.57
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             3402
_reflns_number_gt                2790
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   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)+(0.0544P)²+1.4448P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         3402
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   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
Cl1 Cl 0.286954(17) 0.61681(5) 0.87124(4) 0.06878(17) Uani 1 1 d . . .
O1 O 0.06391(5) 0.93745(10) 0.07067(9) 0.0605(3) Uani 1 1 d . . .
C34 C 0.24298(6) 0.65037(15) 0.74261(14) 0.0489(4) Uani 1 1 d . . .
C35 C 0.21250(7) 0.74713(16) 0.75544(15) 0.0596(4) Uani 1 1 d . . .
H35 H 0.2146 0.7939 0.8335 0.072 Uiso 1 1 calc R . .
C36 C 0.17861(7) 0.77458(15) 0.65133(15) 0.0577(4) Uani 1 1 d . . .
H36 H 0.1578 0.84 0.66 0.069 Uiso 1 1 calc R . .
C31 C 0.17525(5) 0.70591(13) 0.53411(12) 0.0419(3) Uani 1 1 d . . .
C3 C 0.14058(5) 0.73869(13) 0.42110(12) 0.0413(3) Uani 1 1 d . . .
C4 C 0.11956(6) 0.84851(13) 0.39306(13) 0.0430(3) Uani 1 1 d . . .
H4 H 0.1229 0.917 0.4451 0.052 Uiso 1 1 calc R . .
C5 C 0.09269(5) 0.83511(12) 0.27182(12) 0.0403(3) Uani 1 1 d . . .
C51 C 0.06802(6) 0.93378(13) 0.19590(12) 0.0430(3) Uani 1 1 d . . .
C53 C 0.02689(6) 1.12565(13) 0.22720(15) 0.0501(4) Uani 1 1 d . . .
H53A H 0.0275 1.1276 0.1282 0.06 Uiso 1 1 calc R . .
H53B H 0.0438 1.196 0.2616 0.06 Uiso 1 1 calc R . .
C11 C 0.08040(6) 0.65140(14) 0.10939(14) 0.0467(3) Uani 1 1 d . . .
C12 C 0.08243(8) 0.51996(16) 0.14288(19) 0.0647(5) Uani 1 1 d . . .
H12A H 0.0597 0.503 0.2149 0.097 Uiso 1 1 calc R . .
H12B H 0.1159 0.4989 0.1717 0.097 Uiso 1 1 calc R . .
H12C H 0.073 0.4751 0.0632 0.097 Uiso 1 1 calc R . .
C13 C 0.02640(6) 0.68319(17) 0.06891(16) 0.0579(4) Uani 1 1 d . . .
H13A H 0.0244 0.7659 0.0474 0.087 Uiso 1 1 calc R . .
H13B H 0.0048 0.666 0.1434 0.087 Uiso 1 1 calc R . .
H13C H 0.0161 0.6376 -0.0095 0.087 Uiso 1 1 calc R . .
C14 C 0.11632(7) 0.68059(19) -0.00478(16) 0.0658(5) Uani 1 1 d . . .
H14A H 0.1146 0.7637 -0.0247 0.099 Uiso 1 1 calc R . .
H14B H 0.107 0.6363 -0.0851 0.099 Uiso 1 1 calc R . .
H14C H 0.1499 0.6601 0.0235 0.099 Uiso 1 1 calc R . .
C33 C 0.23985(7) 0.58034(17) 0.62877(17) 0.0609(4) Uani 1 1 d . . .
H33 H 0.2604 0.5142 0.6215 0.073 Uiso 1 1 calc R . .
C32 C 0.20598(6) 0.60848(15) 0.52465(16) 0.0551(4) Uani 1 1 d . . .
H32 H 0.2039 0.561 0.4472 0.066 Uiso 1 1 calc R . .
N52 N 0.05323(5) 1.02158(11) 0.27651(11) 0.0504(3) Uani 1 1 d . . .
H52 H 0.0597 1.016 0.3627 0.06 Uiso 1 1 calc R . .
N1 N 0.09769(4) 0.71934(10) 0.23401(10) 0.0411(3) Uani 1 1 d . . .
N2 N 0.12724(5) 0.66020(11) 0.32517(11) 0.0448(3) Uani 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
Cl1 C34 1.7424(15) . ?
O1 C51 1.2296(15) . ?
C34 C33 1.368(2) . ?
C34 C35 1.370(3) . ?
C35 C36 1.382(2) . ?
C36 C31 1.3871(19) . ?
C31 C32 1.377(2) . ?
C31 C3 1.4726(18) . ?
C3 N2 1.3345(17) . ?
C3 C4 1.387(2) . ?
C4 C5 1.3807(18) . ?
C5 N1 1.3674(18) . ?
C5 C51 1.485(2) . ?
C51 N52 1.3334(18) . ?
C53 N52 1.4472(19) . ?
C53 C53 1.511(3) 2 ?
C11 N1 1.5052(16) . ?
C11 C12 1.522(2) . ?
C11 C14 1.524(2) . ?
C11 C13 1.526(2) . ?
C33 C32 1.383(2) . ?
N1 N2 1.3535(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
C33 C34 C35 120.77(14) . . ?
C33 C34 Cl1 119.38(14) . . ?
C35 C34 Cl1 119.85(12) . . ?
C34 C35 C36 119.36(14) . . ?
C35 C36 C31 120.92(16) . . ?
C32 C31 C36 118.44(13) . . ?
C32 C31 C3 120.96(12) . . ?
C36 C31 C3 120.58(14) . . ?
N2 C3 C4 110.86(12) . . ?
N2 C3 C31 120.93(13) . . ?
C4 C3 C31 128.14(13) . . ?
C5 C4 C3 105.74(12) . . ?
N1 C5 C4 106.62(12) . . ?
N1 C5 C51 128.88(12) . . ?
C4 C5 C51 124.26(13) . . ?
O1 C51 N52 123.01(14) . . ?
O1 C51 C5 123.57(13) . . ?
N52 C51 C5 113.32(11) . . ?
N52 C53 C53 110.94(11) . 2 ?
N1 C11 C12 108.34(12) . . ?
N1 C11 C14 107.39(12) . . ?
C12 C11 C14 110.45(15) . . ?
N1 C11 C13 111.07(12) . . ?
C12 C11 C13 108.32(14) . . ?
C14 C11 C13 111.24(14) . . ?
C34 C33 C32 119.62(16) . . ?
C31 C32 C33 120.88(14) . . ?
C51 N52 C53 123.72(12) . . ?
N2 N1 C5 110.66(11) . . ?
N2 N1 C11 116.45(11) . . ?
C5 N1 C11 132.69(12) . . ?
C3 N2 N1 106.11(12) . . ?

# 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_compound_8c
_database_code_depnum_ccdc_archive 'CCDC 1498468'
_audit_update_record             
;
2017-09-21 deposited with the CCDC.
2017-10-04 downloaded from the CCDC.
;

_audit_creation_date             2017-04-08T09:48:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
'1,2-bis(aminocarbonyl-(3'-phenyl)-(1'(tert-butyl)-1H-pyrazole-5'-il)ethane'
;
_chemical_name_common            thread-1,5-fenil
_chemical_formula_moiety         'C30 H36 N6 O2'
_chemical_formula_sum            'C30 H36 N6 O2'
_chemical_formula_weight         512.65
_chemical_melting_point          none

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  -P2ybc
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.0096(10)
_cell_length_b                   18.5432(14)
_cell_length_c                   12.0412(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.744(3)
_cell_angle_gamma                90
_cell_volume                     2853.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9906
_cell_measurement_theta_min      4.2025
_cell_measurement_theta_max      68.089

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1096

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

_exptl_absorpt_coefficient_mu    0.612
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   
;
'SADABS (version 2012/1; Bruker, 2012) was used to perform the numerical
absorption correction based on the indexed faces of the cystal.'
;
_exptl_absorpt_correction_T_min  0.6743
_exptl_absorpt_correction_T_max  0.7531

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

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean none
_diffrn_measurement_device_type  'D8 Quest'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_number            22676
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.2
_diffrn_reflns_theta_max         68.18
_diffrn_reflns_theta_full        68.18
_diffrn_measured_fraction_theta_full 0.963
_diffrn_measured_fraction_theta_max 0.963
_reflns_number_total             5035
_reflns_number_gt                4506
_reflns_threshold_expression     >2σ(I)

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

_computing_data_collection       'BRUKER APEX-III'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
#                   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)+(0.1612P)²+5.3603P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       none
_refine_ls_number_reflns         5035
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0996
_refine_ls_wR_factor_ref         0.3454
_refine_ls_wR_factor_gt          0.3381
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_restrained_S_all      1.176
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.576
_refine_diff_density_min         -0.539
_refine_diff_density_rms         0.175

#----------------------------------------------------------------------------#
#                   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 0.0181 0.0091 '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 0.0311 0.018 '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'

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
O2 O 0.5562(3) 0.74081(18) 0.3076(3) 0.0625(9) Uani 1 1 d . . .
O1 O 0.4099(3) 0.52640(17) 0.6200(3) 0.0645(10) Uani 1 1 d . . .
N52' N 0.5567(3) 0.6262(2) 0.3710(3) 0.0490(9) Uani 1 1 d . . .
H52' H 0.5789 0.5831 0.3633 0.059 Uiso 1 1 calc R . .
N52 N 0.4811(3) 0.6361(2) 0.6532(3) 0.0494(9) Uani 1 1 d . . .
H52 H 0.4846 0.675 0.6925 0.059 Uiso 1 1 calc R . .
N2 N 0.1944(3) 0.6153(2) 0.8153(3) 0.0482(9) Uani 1 1 d . . .
N1 N 0.2367(3) 0.5964(2) 0.7253(3) 0.0465(9) Uani 1 1 d . . .
N1' N 0.7588(3) 0.67520(19) 0.2375(3) 0.0433(8) Uani 1 1 d . . .
N2' N 0.8010(3) 0.6451(2) 0.1537(3) 0.0470(9) Uani 1 1 d . . .
C34' C 0.7801(8) 0.4935(3) -0.1971(5) 0.096(3) Uani 1 1 d . . .
H34' H 0.7922 0.4704 -0.2621 0.116 Uiso 1 1 calc R . .
C33' C 0.8631(7) 0.5184(4) -0.1189(6) 0.089(2) Uani 1 1 d . . .
H33' H 0.9311 0.5117 -0.1308 0.106 Uiso 1 1 calc R . .
C32' C 0.8458(5) 0.5532(3) -0.0229(5) 0.0685(14) Uani 1 1 d . . .
H32' H 0.9023 0.57 0.0298 0.082 Uiso 1 1 calc R . .
C31' C 0.7451(4) 0.5633(2) -0.0044(4) 0.0534(11) Uani 1 1 d . . .
C3' C 0.7264(4) 0.6033(2) 0.0956(3) 0.0464(10) Uani 1 1 d . . .
C4' C 0.6358(4) 0.6061(2) 0.1428(4) 0.0501(10) Uani 1 1 d . . .
H4' H 0.5736 0.5812 0.1188 0.06 Uiso 1 1 calc R . .
C5' C 0.6584(3) 0.6533(2) 0.2322(3) 0.0427(9) Uani 1 1 d . . .
C51' C 0.5863(3) 0.6781(2) 0.3072(3) 0.0439(9) Uani 1 1 d . . .
C53' C 0.4896(4) 0.6379(3) 0.4523(4) 0.0550(12) Uani 1 1 d . . .
H53A H 0.4315 0.6043 0.4379 0.066 Uiso 1 1 calc R . .
H53B H 0.4614 0.6864 0.4437 0.066 Uiso 1 1 calc R . .
C53 C 0.5488(4) 0.6278(3) 0.5712(4) 0.0545(11) Uani 1 1 d . . .
H53C H 0.5799 0.5801 0.5786 0.065 Uiso 1 1 calc R . .
H53D H 0.6049 0.6629 0.5866 0.065 Uiso 1 1 calc R . .
C51 C 0.4134(3) 0.5846(2) 0.6694(3) 0.0440(9) Uani 1 1 d . . .
C5 C 0.3431(3) 0.6034(2) 0.7490(3) 0.0421(9) Uani 1 1 d . . .
C4 C 0.3686(3) 0.6287(2) 0.8578(3) 0.0426(9) Uani 1 1 d . . .
H4 H 0.4351 0.6395 0.8977 0.051 Uiso 1 1 calc R . .
C3 C 0.2737(3) 0.6348(2) 0.8961(3) 0.0411(9) Uani 1 1 d . . .
C31 C 0.2499(3) 0.6599(2) 1.0043(3) 0.0438(9) Uani 1 1 d . . .
C36 C 0.1469(4) 0.6596(3) 1.0208(4) 0.0603(12) Uani 1 1 d . . .
H36 H 0.094 0.6439 0.963 0.072 Uiso 1 1 calc R . .
C35 C 0.1222(5) 0.6822(3) 1.1212(5) 0.0727(15) Uani 1 1 d . . .
H35 H 0.0529 0.6811 1.131 0.087 Uiso 1 1 calc R . .
C34 C 0.1991(5) 0.7065(3) 1.2073(5) 0.0668(14) Uani 1 1 d . . .
H34 H 0.1822 0.7222 1.2751 0.08 Uiso 1 1 calc R . .
C36' C 0.6621(5) 0.5372(3) -0.0830(4) 0.0700(15) Uani 1 1 d . . .
H36' H 0.5941 0.543 -0.0709 0.084 Uiso 1 1 calc R . .
C35' C 0.6796(7) 0.5023(3) -0.1800(5) 0.090(2) Uani 1 1 d . . .
H35' H 0.6235 0.4852 -0.2329 0.108 Uiso 1 1 calc R . .
C11 C 0.1637(4) 0.5751(3) 0.6192(4) 0.0586(12) Uani 1 1 d . . .
C13 C 0.1650(6) 0.4935(4) 0.6108(7) 0.105(3) Uani 1 1 d . . .
H13A H 0.1433 0.4729 0.6759 0.157 Uiso 1 1 calc R . .
H13B H 0.2346 0.4775 0.6076 0.157 Uiso 1 1 calc R . .
H13C H 0.118 0.4784 0.5437 0.157 Uiso 1 1 calc R . .
C12 C 0.1966(5) 0.6117(4) 0.5181(4) 0.0780(17) Uani 1 1 d . . .
H12A H 0.1945 0.663 0.5271 0.117 Uiso 1 1 calc R . .
H12B H 0.1496 0.5979 0.4502 0.117 Uiso 1 1 calc R . .
H12C H 0.2665 0.5971 0.5133 0.117 Uiso 1 1 calc R . .
C14 C 0.0544(4) 0.6022(4) 0.6282(6) 0.088(2) Uani 1 1 d . . .
H14A H 0.0551 0.6539 0.6329 0.132 Uiso 1 1 calc R . .
H14B H 0.0344 0.5824 0.6948 0.132 Uiso 1 1 calc R . .
H14C H 0.0051 0.5873 0.5627 0.132 Uiso 1 1 calc R . .
C32 C 0.3268(4) 0.6843(2) 1.0921(4) 0.0516(11) Uani 1 1 d . . .
H32 H 0.3962 0.6852 1.0831 0.062 Uiso 1 1 calc R . .
C33 C 0.3013(4) 0.7074(3) 1.1923(4) 0.0595(12) Uani 1 1 d . . .
H33 H 0.3537 0.7236 1.2503 0.071 Uiso 1 1 calc R . .
C11' C 0.8233(4) 0.7282(3) 0.3150(4) 0.0511(11) Uani 1 1 d . . .
C12' C 0.9374(4) 0.7105(5) 0.3183(7) 0.103(3) Uani 1 1 d . . .
H12D H 0.9527 0.7143 0.2435 0.155 Uiso 1 1 calc R . .
H12E H 0.9514 0.6623 0.3458 0.155 Uiso 1 1 calc R . .
H12F H 0.9804 0.7437 0.3676 0.155 Uiso 1 1 calc R . .
C13' C 0.7962(7) 0.8032(3) 0.2668(6) 0.099(2) Uani 1 1 d . . .
H13D H 0.8115 0.806 0.192 0.149 Uiso 1 1 calc R . .
H13E H 0.837 0.8385 0.3142 0.149 Uiso 1 1 calc R . .
H13F H 0.7232 0.8124 0.264 0.149 Uiso 1 1 calc R . .
C14' C 0.8003(5) 0.7224(4) 0.4331(4) 0.0721(15) Uani 1 1 d . . .
H14D H 0.728 0.7334 0.4317 0.108 Uiso 1 1 calc R . .
H14E H 0.8434 0.7559 0.4818 0.108 Uiso 1 1 calc R . .
H14F H 0.815 0.6743 0.461 0.108 Uiso 1 1 calc R . .



#----------------------------------------------------------------------------#
#                   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
O2 C51' 1.228(5) . ?
O1 C51 1.229(5) . ?
N52' C51' 1.332(5) . ?
N52' C53' 1.444(5) . ?
N52' H52' 0.86 . ?
N52 C51 1.338(6) . ?
N52 C53 1.448(5) . ?
N52 H52 0.86 . ?
N2 C3 1.330(5) . ?
N2 N1 1.350(5) . ?
N1 C5 1.367(5) . ?
N1 C11 1.495(6) . ?
N1' N2' 1.355(5) . ?
N1' C5' 1.358(5) . ?
N1' C11' 1.499(6) . ?
N2' C3' 1.334(6) . ?
C34' C35' 1.372(12) . ?
C34' C33' 1.373(11) . ?
C34' H34' 0.93 . ?
C33' C32' 1.380(8) . ?
C33' H33' 0.93 . ?
C32' C31' 1.382(8) . ?
C32' H32' 0.93 . ?
C31' C36' 1.384(8) . ?
C31' C3' 1.472(6) . ?
C3' C4' 1.401(6) . ?
C4' C5' 1.376(6) . ?
C4' H4' 0.93 . ?
C5' C51' 1.490(6) . ?
C53' C53 1.506(7) . ?
C53' H53A 0.97 . ?
C53' H53B 0.97 . ?
C53 H53C 0.97 . ?
C53 H53D 0.97 . ?
C51 C5 1.484(6) . ?
C5 C4 1.373(6) . ?
C4 C3 1.402(6) . ?
C4 H4 0.93 . ?
C3 C31 1.470(6) . ?
C31 C32 1.389(6) . ?
C31 C36 1.390(7) . ?
C36 C35 1.374(7) . ?
C36 H36 0.93 . ?
C35 C34 1.376(8) . ?
C35 H35 0.93 . ?
C34 C33 1.375(8) . ?
C34 H34 0.93 . ?
C36' C35' 1.390(8) . ?
C36' H36' 0.93 . ?
C35' H35' 0.93 . ?
C11 C13 1.516(8) . ?
C11 C12 1.523(8) . ?
C11 C14 1.532(8) . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C12 H12A 0.96 . ?
C12 H12B 0.96 . ?
C12 H12C 0.96 . ?
C14 H14A 0.96 . ?
C14 H14B 0.96 . ?
C14 H14C 0.96 . ?
C32 C33 1.378(7) . ?
C32 H32 0.93 . ?
C33 H33 0.93 . ?
C11' C14' 1.511(6) . ?
C11' C12' 1.513(8) . ?
C11' C13' 1.523(8) . ?
C12' H12D 0.96 . ?
C12' H12E 0.96 . ?
C12' H12F 0.96 . ?
C13' H13D 0.96 . ?
C13' H13E 0.96 . ?
C13' H13F 0.96 . ?
C14' H14D 0.96 . ?
C14' H14E 0.96 . ?
C14' H14F 0.96 . ?

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
C51' N52' C53' 124.0(4) . . ?
C51' N52' H52' 118 . . ?
C53' N52' H52' 118 . . ?
C51 N52 C53 121.6(4) . . ?
C51 N52 H52 119.2 . . ?
C53 N52 H52 119.2 . . ?
C3 N2 N1 106.3(3) . . ?
N2 N1 C5 110.9(3) . . ?
N2 N1 C11 117.7(4) . . ?
C5 N1 C11 131.3(4) . . ?
N2' N1' C5' 111.2(3) . . ?
N2' N1' C11' 118.4(3) . . ?
C5' N1' C11' 130.3(3) . . ?
C3' N2' N1' 105.9(3) . . ?
C35' C34' C33' 120.4(6) . . ?
C35' C34' H34' 119.8 . . ?
C33' C34' H34' 119.8 . . ?
C34' C33' C32' 120.1(7) . . ?
C34' C33' H33' 119.9 . . ?
C32' C33' H33' 119.9 . . ?
C33' C32' C31' 120.4(6) . . ?
C33' C32' H32' 119.8 . . ?
C31' C32' H32' 119.8 . . ?
C32' C31' C36' 119.0(5) . . ?
C32' C31' C3' 120.4(5) . . ?
C36' C31' C3' 120.5(5) . . ?
N2' C3' C4' 110.4(4) . . ?
N2' C3' C31' 120.4(4) . . ?
C4' C3' C31' 129.1(4) . . ?
C5' C4' C3' 105.6(4) . . ?
C5' C4' H4' 127.2 . . ?
C3' C4' H4' 127.2 . . ?
N1' C5' C4' 106.8(4) . . ?
N1' C5' C51' 126.0(4) . . ?
C4' C5' C51' 127.1(4) . . ?
O2 C51' N52' 123.7(4) . . ?
O2 C51' C5' 122.1(4) . . ?
N52' C51' C5' 114.2(4) . . ?
N52' C53' C53 111.1(4) . . ?
N52' C53' H53A 109.4 . . ?
C53 C53' H53A 109.4 . . ?
N52' C53' H53B 109.4 . . ?
C53 C53' H53B 109.4 . . ?
H53A C53' H53B 108 . . ?
N52 C53 C53' 111.6(4) . . ?
N52 C53 H53C 109.3 . . ?
C53' C53 H53C 109.3 . . ?
N52 C53 H53D 109.3 . . ?
C53' C53 H53D 109.3 . . ?
H53C C53 H53D 108 . . ?
O1 C51 N52 121.5(4) . . ?
O1 C51 C5 123.2(4) . . ?
N52 C51 C5 115.4(4) . . ?
N1 C5 C4 106.7(4) . . ?
N1 C5 C51 124.4(4) . . ?
C4 C5 C51 128.9(4) . . ?
C5 C4 C3 105.7(4) . . ?
C5 C4 H4 127.1 . . ?
C3 C4 H4 127.1 . . ?
N2 C3 C4 110.4(4) . . ?
N2 C3 C31 118.2(4) . . ?
C4 C3 C31 131.5(4) . . ?
C32 C31 C36 118.0(4) . . ?
C32 C31 C3 122.5(4) . . ?
C36 C31 C3 119.6(4) . . ?
C35 C36 C31 121.0(5) . . ?
C35 C36 H36 119.5 . . ?
C31 C36 H36 119.5 . . ?
C36 C35 C34 120.4(5) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C33 C34 C35 119.4(5) . . ?
C33 C34 H34 120.3 . . ?
C35 C34 H34 120.3 . . ?
C31' C36' C35' 120.5(7) . . ?
C31' C36' H36' 119.7 . . ?
C35' C36' H36' 119.7 . . ?
C34' C35' C36' 119.5(7) . . ?
C34' C35' H35' 120.3 . . ?
C36' C35' H35' 120.3 . . ?
N1 C11 C13 107.9(4) . . ?
N1 C11 C12 109.7(4) . . ?
C13 C11 C12 112.5(6) . . ?
N1 C11 C14 107.6(4) . . ?
C13 C11 C14 110.8(5) . . ?
C12 C11 C14 108.3(5) . . ?
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 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C33 C32 C31 120.7(5) . . ?
C33 C32 H32 119.6 . . ?
C31 C32 H32 119.6 . . ?
C34 C33 C32 120.5(5) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
N1' C11' C14' 110.7(4) . . ?
N1' C11' C12' 107.9(4) . . ?
C14' C11' C12' 109.0(5) . . ?
N1' C11' C13' 107.4(4) . . ?
C14' C11' C13' 110.5(5) . . ?
C12' C11' C13' 111.3(6) . . ?
C11' C12' H12D 109.5 . . ?
C11' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C11' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
C11' C13' H13D 109.5 . . ?
C11' C13' H13E 109.5 . . ?
H13D C13' H13E 109.5 . . ?
C11' C13' H13F 109.5 . . ?
H13D C13' H13F 109.5 . . ?
H13E C13' H13F 109.5 . . ?
C11' C14' H14D 109.5 . . ?
C11' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C11' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 N1 C5 0.4(5) . . . . ?
C3 N2 N1 C11 -177.3(4) . . . . ?
C5' N1' N2' C3' -0.5(5) . . . . ?
C11' N1' N2' C3' -177.3(4) . . . . ?
C35' C34' C33' C32' -0.6(10) . . . . ?
C34' C33' C32' C31' 0.0(9) . . . . ?
C33' C32' C31' C36' 0.8(8) . . . . ?
C33' C32' C31' C3' -177.3(5) . . . . ?
N1' N2' C3' C4' -0.4(5) . . . . ?
N1' N2' C3' C31' 178.5(4) . . . . ?
C32' C31' C3' N2' 16.8(6) . . . . ?
C36' C31' C3' N2' -161.3(5) . . . . ?
C32' C31' C3' C4' -164.5(5) . . . . ?
C36' C31' C3' C4' 17.4(7) . . . . ?
N2' C3' C4' C5' 1.2(5) . . . . ?
C31' C3' C4' C5' -177.6(4) . . . . ?
N2' N1' C5' C4' 1.3(5) . . . . ?
C11' N1' C5' C4' 177.6(4) . . . . ?
N2' N1' C5' C51' -177.0(4) . . . . ?
C11' N1' C5' C51' -0.6(7) . . . . ?
C3' C4' C5' N1' -1.4(5) . . . . ?
C3' C4' C5' C51' 176.8(4) . . . . ?
C53' N52' C51' O2 -3.1(7) . . . . ?
C53' N52' C51' C5' 178.2(4) . . . . ?
N1' C5' C51' O2 64.9(6) . . . . ?
C4' C5' C51' O2 -112.9(5) . . . . ?
N1' C5' C51' N52' -116.3(5) . . . . ?
C4' C5' C51' N52' 65.8(6) . . . . ?
C51' N52' C53' C53 -111.7(5) . . . . ?
C51 N52 C53 C53' 75.4(6) . . . . ?
N52' C53' C53 N52 -177.3(4) . . . . ?
C53 N52 C51 O1 4.3(7) . . . . ?
C53 N52 C51 C5 -175.0(4) . . . . ?
N2 N1 C5 C4 -0.9(5) . . . . ?
C11 N1 C5 C4 176.4(4) . . . . ?
N2 N1 C5 C51 177.8(4) . . . . ?
C11 N1 C5 C51 -4.9(7) . . . . ?
O1 C51 C5 N1 -50.7(6) . . . . ?
N52 C51 C5 N1 128.6(4) . . . . ?
O1 C51 C5 C4 127.7(5) . . . . ?
N52 C51 C5 C4 -53.0(6) . . . . ?
N1 C5 C4 C3 0.9(4) . . . . ?
C51 C5 C4 C3 -177.7(4) . . . . ?
N1 N2 C3 C4 0.2(5) . . . . ?
N1 N2 C3 C31 178.6(3) . . . . ?
C5 C4 C3 N2 -0.8(5) . . . . ?
C5 C4 C3 C31 -178.8(4) . . . . ?
N2 C3 C31 C32 -177.1(4) . . . . ?
C4 C3 C31 C32 0.9(7) . . . . ?
N2 C3 C31 C36 2.7(6) . . . . ?
C4 C3 C31 C36 -179.3(4) . . . . ?
C32 C31 C36 C35 -0.6(7) . . . . ?
C3 C31 C36 C35 179.5(5) . . . . ?
C31 C36 C35 C34 0.8(9) . . . . ?
C36 C35 C34 C33 -0.5(9) . . . . ?
C32' C31' C36' C35' -1.0(8) . . . . ?
C3' C31' C36' C35' 177.1(5) . . . . ?
C33' C34' C35' C36' 0.4(10) . . . . ?
C31' C36' C35' C34' 0.4(9) . . . . ?
N2 N1 C11 C13 -102.4(6) . . . . ?
C5 N1 C11 C13 80.5(7) . . . . ?
N2 N1 C11 C12 134.7(5) . . . . ?
C5 N1 C11 C12 -42.4(7) . . . . ?
N2 N1 C11 C14 17.2(6) . . . . ?
C5 N1 C11 C14 -159.9(5) . . . . ?
C36 C31 C32 C33 0.2(7) . . . . ?
C3 C31 C32 C33 -179.9(4) . . . . ?
C35 C34 C33 C32 0.1(8) . . . . ?
C31 C32 C33 C34 0.0(7) . . . . ?
N2' N1' C11' C14' -146.0(4) . . . . ?
C5' N1' C11' C14' 37.9(6) . . . . ?
N2' N1' C11' C12' -26.8(6) . . . . ?
C5' N1' C11' C12' 157.0(5) . . . . ?
N2' N1' C11' C13' 93.3(5) . . . . ?
C5' N1' C11' C13' -82.9(6) . . . . ?

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
C13 H13B O1 0.96 2.43 3.226(9) 139.7 .
C12 H12C O1 0.96 2.44 3.231(8) 139.3 .
C13' H13F O2 0.96 2.68 3.450(9) 137.6 .
C14' H14D O2 0.96 2.45 3.271(7) 143.4 .

# END of CIF
