# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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/. 
# 
# 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_872_4a
_database_code_depnum_ccdc_archive 'CCDC 1026939'
_audit_update_record             
;
2014-09-29 deposited with the CCDC.
2014-12-09 downloaded from the CCDC.
;

_chemical_name_systematic        
5-Chloro-1',1''-dimethyl-4'-(4-methylphenyl)-5''-[(4-methylphenyl)methylidene]-dispiro[3H-indole-3,2'-pyrrolidine-3',3''-piperidine]-2(1H),4''-dione

_chemical_formula_sum            'C32 H32 Cl1 N3 O2'
_chemical_formula_moiety         'C32 H32 Cl1 N3 O2'
_chemical_formula_iupac          'C32 H32 Cl1 N3 O2'
_chemical_formula_weight         526.08
_chemical_melting_point          514(1)
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1 '
_symmetry_space_group_name_Hall  ?

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2

_cell_length_a                   11.6216(6)
_cell_length_b                   20.8276(9)
_cell_length_c                   11.8949(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.3419(17)
_cell_angle_gamma                90
_cell_volume                     2861.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4788
_cell_measurement_theta_min      3
_cell_measurement_theta_max      30
_cell_measurement_temperature    298(2)

_exptl_crystal_description       Needle
_exptl_crystal_colour            Colorless
_exptl_crystal_size_min          0.08
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_max          0.16
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112

_exptl_absorpt_coefficient_mu    0.166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  1.00
_exptl_absorpt_correction_T_max  1.00

_chemical_absolute_configuration rm

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius 590 KappaCCD'
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'

_diffrn_reflns_number            9983
_diffrn_reflns_av_R_equivalents  0.151

_diffrn_reflns_theta_min         3.039
_diffrn_reflns_theta_max         28.188
_diffrn_reflns_theta_full        25.087
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -14
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              25
_reflns_limit_l_min              0
_reflns_limit_l_max              15
_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0

_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. 
;





loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   difmap
_reflns_threshold_expression     I>2.0σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.10P)² + 0.00P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

_reflns_number_total             4939
_reflns_number_gt                1569
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_gt          0.1331
_refine_ls_R_factor_all          0.3533
_refine_ls_wR_factor_all         0.2459
_refine_ls_number_reflns         1569
_refine_ls_number_restraints     147
_refine_ls_number_parameters     236
_refine_ls_wR_factor_ref         0.1331
_refine_ls_goodness_of_fit_ref   1.0301
_refine_ls_shift/su_max          0.0062096
_refine_ls_shift/su_mean         0.0004345
_refine_diff_density_min         -0.33
_refine_diff_density_max         0.27


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 0.5089(2) 0.66945(18) 1.0707(2) 0.1842 1.0000 Uani . . . . . .
O1 O 0.8105(4) 0.7080(3) 0.8197(5) 0.0940 1.0000 Uani . . . . . .
O2 O 0.6575(4) 0.5103(3) 0.5373(5) 0.0854 1.0000 Uani . . . . . .
N1 N 0.6542(5) 0.6560(3) 0.5111(5) 0.0642 1.0000 Uani D . . . . .
N2 N 0.5064(6) 0.5481(3) 0.6295(5) 0.0704 1.0000 Uani D . . . . .
N3 N 0.7687(7) 0.5266(4) 0.7785(5) 0.0877 1.0000 Uani D . . . . .
C1 C 0.9036(7) 0.5995(4) 0.7277(7) 0.0749 1.0000 Uani D . . . . .
C2 C 1.0073(7) 0.6195(5) 0.6711(9) 0.0777 1.0000 Uani D . . . . .
C3 C 1.0644(10) 0.6743(5) 0.7130(7) 0.1141 1.0000 Uani D . . . . .
C4 C 1.1611(11) 0.6957(5) 0.6655(12) 0.1236 1.0000 Uani D . . . . .
C5 C 1.2054(9) 0.6638(7) 0.5794(12) 0.1080 1.0000 Uani D . . . . .
C6 C 1.1509(11) 0.6089(7) 0.5386(7) 0.1149 1.0000 Uani D . . . . .
C7 C 1.0519(10) 0.5880(4) 0.5852(9) 0.0969 1.0000 Uani D . . . . .
C8 C 1.3144(8) 0.6854(5) 0.5309(8) 0.1508 1.0000 Uani D . . . . .
C9 C 0.8803(7) 0.5274(4) 0.7330(7) 0.0926 1.0000 Uani D . . . . .
C10 C 0.7177(7) 0.4626(5) 0.7938(8) 0.1182 1.0000 Uani D . . . . .
C11 C 0.6943(7) 0.5730(4) 0.7142(7) 0.0664 1.0000 Uani . . . . . .
C12 C 0.6008(8) 0.5962(3) 0.7839(7) 0.0664 1.0000 Uani D . . . . .
C13 C 0.6059(8) 0.6232(4) 0.8900(8) 0.0885 1.0000 Uani D . . . . .
C14 C 0.5052(11) 0.6350(3) 0.9370(7) 0.1027 1.0000 Uani D . . . . .
C15 C 0.3977(8) 0.6212(3) 0.8815(8) 0.0948 1.0000 Uani D . . . . .
C16 C 0.3911(7) 0.5925(3) 0.7761(8) 0.0797 1.0000 Uani D . . . . .
C17 C 0.4926(9) 0.5803(3) 0.7309(7) 0.0667 1.0000 Uani D . . . . .
C18 C 0.6208(8) 0.5412(4) 0.6122(7) 0.0690 1.0000 Uani D . . . . .
C19 C 0.7824(6) 0.6257(4) 0.6790(6) 0.0643 1.0000 Uani D . . . . .
C20 C 0.7585(7) 0.6915(4) 0.7286(7) 0.0707 1.0000 Uani . . . . . .
C21 C 0.6702(6) 0.7335(4) 0.6676(6) 0.0650 1.0000 Uani D . . . . .
C22 C 0.6226(6) 0.7780(4) 0.7282(7) 0.0718 1.0000 Uani D . . . . .
C23 C 0.5366(6) 0.8275(4) 0.6921(8) 0.0668 1.0000 Uani D . . . . .
C24 C 0.5213(7) 0.8554(4) 0.5860(8) 0.0857 1.0000 Uani D . . . . .
C25 C 0.4394(9) 0.9031(4) 0.5626(8) 0.1069 1.0000 Uani D . . . . .
C26 C 0.3715(7) 0.9244(4) 0.6384(12) 0.0995 1.0000 Uani D . . . . .
C27 C 0.3869(7) 0.8982(5) 0.7442(10) 0.1010 1.0000 Uani D . . . . .
C28 C 0.4681(8) 0.8508(4) 0.7705(7) 0.0843 1.0000 Uani D . . . . .
C29 C 0.2855(8) 0.9797(5) 0.6098(8) 0.1664 1.0000 Uani D . . . . .
C30 C 0.6396(5) 0.7224(4) 0.5434(6) 0.0647 1.0000 Uani D . . . . .
C31 C 0.7719(6) 0.6348(4) 0.5500(6) 0.0722 1.0000 Uani D . . . . .
C32 C 0.6225(6) 0.6466(4) 0.3909(6) 0.0836 1.0000 Uani D . . . . .
H103 H 0.769(3) 0.4380(15) 0.847(4) 0.1420 1.0000 Uiso D . . . . .
H101 H 0.644(3) 0.4668(13) 0.821(4) 0.1420 1.0000 Uiso D . . . . .
H102 H 0.709(4) 0.4406(15) 0.722(2) 0.1420 1.0000 Uiso D . . . . .
H241 H 0.5664(15) 0.8422(9) 0.5303(18) 0.1007 1.0000 Uiso D . . . . .
H251 H 0.4309(18) 0.9208(9) 0.4903(18) 0.1263 1.0000 Uiso D . . . . .
H292 H 0.281(5) 0.989(2) 0.531(2) 0.1973 1.0000 Uiso D . . . . .
H293 H 0.310(4) 1.0169(15) 0.653(5) 0.1973 1.0000 Uiso D . . . . .
H291 H 0.210(2) 0.9667(18) 0.628(5) 0.1973 1.0000 Uiso D . . . . .
H271 H 0.3422(16) 0.9129(10) 0.799(2) 0.1156 1.0000 Uiso D . . . . .
H281 H 0.4779(17) 0.8340(9) 0.8439(17) 0.0975 1.0000 Uiso D . . . . .
H221 H 0.6482(14) 0.7781(9) 0.8053(17) 0.0836 1.0000 Uiso D . . . . .
H301 H 0.689(2) 0.7496(12) 0.501(2) 0.0767 1.0000 Uiso D . . . . .
H302 H 0.5586(18) 0.7348(13) 0.525(2) 0.0767 1.0000 Uiso D . . . . .
H322 H 0.545(2) 0.6618(19) 0.370(2) 0.0966 1.0000 Uiso D . . . . .
H323 H 0.675(3) 0.6698(17) 0.349(2) 0.0966 1.0000 Uiso D . . . . .
H321 H 0.627(3) 0.6012(10) 0.374(2) 0.0966 1.0000 Uiso D . . . . .
H312 H 0.828(2) 0.6667(12) 0.532(2) 0.0844 1.0000 Uiso D . . . . .
H311 H 0.787(2) 0.5940(11) 0.513(2) 0.0844 1.0000 Uiso D . . . . .
H31 H 1.037(2) 0.6967(11) 0.7730(15) 0.1314 1.0000 Uiso D . . . . .
H41 H 1.197(2) 0.7338(9) 0.693(2) 0.1473 1.0000 Uiso D . . . . .
H83 H 1.316(3) 0.7314(10) 0.528(5) 0.1846 1.0000 Uiso D . . . . .
H81 H 1.381(2) 0.670(3) 0.578(4) 0.1846 1.0000 Uiso D . . . . .
H82 H 1.314(4) 0.668(3) 0.455(3) 0.1846 1.0000 Uiso D . . . . .
H61 H 1.179(2) 0.5857(12) 0.4803(14) 0.1554 1.0000 Uiso D . . . . .
H71 H 1.015(2) 0.5511(9) 0.5562(18) 0.1157 1.0000 Uiso D . . . . .
H11 H 0.916(2) 0.6155(12) 0.8054(18) 0.0900 1.0000 Uiso D . . . . .
H92 H 0.939(2) 0.5056(13) 0.783(2) 0.1105 1.0000 Uiso D . . . . .
H91 H 0.876(2) 0.5081(13) 0.6582(19) 0.1105 1.0000 Uiso D . . . . .
H21 H 0.4515 0.5271 0.5913 0.0808 1.0000 Uiso DR . . . . .
H151 H 0.3306(19) 0.6313(6) 0.9139(19) 0.1146 1.0000 Uiso D . . . . .
H161 H 0.3196(18) 0.5812(6) 0.7375(19) 0.0952 1.0000 Uiso D . . . . .
H131 H 0.6770(19) 0.6340(6) 0.9300(19) 0.1043 1.0000 Uiso D . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1762(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 . C14 . 1.741(8) yes
O1 . C20 . 1.230(7) yes
O2 . C18 . 1.215(8) yes
N1 . C30 . 1.450(8) yes
N1 . C31 . 1.463(7) yes
N1 . C32 . 1.450(7) yes
N2 . C17 . 1.405(8) yes
N2 . C18 . 1.375(8) yes
N2 . H21 . 0.861 no
N3 . C9 . 1.460(9) yes
N3 . C10 . 1.478(9) yes
N3 . C11 . 1.458(8) yes
C1 . C2 . 1.504(10) yes
C1 . C9 . 1.529(10) yes
C1 . C19 . 1.561(9) yes
C1 . H11 . 0.978(18) no
C2 . C3 . 1.385(10) yes
C2 . C7 . 1.363(10) yes
C3 . C4 . 1.387(11) yes
C3 . H31 . 0.936(18) no
C4 . C5 . 1.367(12) yes
C4 . H41 . 0.941(18) no
C5 . C6 . 1.370(12) yes
C5 . C8 . 1.518(12) yes
C6 . C7 . 1.400(11) yes
C6 . H61 . 0.933(18) no
C7 . H71 . 0.929(18) no
C8 . H83 . 0.959(18) no
C8 . H81 . 0.959(18) no
C8 . H82 . 0.964(18) no
C9 . H92 . 0.967(18) no
C9 . H91 . 0.973(18) no
C10 . H103 . 0.967(18) no
C10 . H101 . 0.960(18) no
C10 . H102 . 0.962(18) no
C11 . C12 . 1.517(9) yes
C11 . C18 . 1.553(9) yes
C11 . C19 . 1.589(9) yes
C12 . C13 . 1.377(10) yes
C12 . C17 . 1.383(9) yes
C13 . C14 . 1.373(10) yes
C13 . H131 . 0.935(18) no
C14 . C15 . 1.378(9) yes
C15 . C16 . 1.382(9) yes
C15 . H151 . 0.931(18) no
C16 . C17 . 1.372(9) yes
C16 . H161 . 0.935(18) no
C19 . C20 . 1.528(9) yes
C19 . C31 . 1.538(8) yes
C20 . C21 . 1.477(10) yes
C21 . C22 . 1.332(9) yes
C21 . C30 . 1.499(9) yes
C22 . C23 . 1.467(10) yes
C22 . H221 . 0.933(18) no
C23 . C24 . 1.383(9) yes
C23 . C28 . 1.379(9) yes
C24 . C25 . 1.383(10) yes
C24 . H241 . 0.931(18) no
C25 . C26 . 1.338(10) yes
C25 . H251 . 0.931(18) no
C26 . C27 . 1.365(11) yes
C26 . C29 . 1.537(11) yes
C27 . C28 . 1.377(10) yes
C27 . H271 . 0.933(18) no
C28 . H281 . 0.936(18) no
C29 . H292 . 0.961(18) no
C29 . H293 . 0.958(18) no
C29 . H291 . 0.962(18) no
C30 . H301 . 0.981(18) no
C30 . H302 . 0.978(18) no
C31 . H312 . 0.971(18) no
C31 . H311 . 0.979(18) no
C32 . H322 . 0.962(18) no
C32 . H323 . 0.960(18) no
C32 . H321 . 0.970(18) no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C30 . N1 . C31 . 109.7(5) yes
C30 . N1 . C32 . 111.4(6) yes
C31 . N1 . C32 . 113.5(6) yes
C17 . N2 . C18 . 112.5(7) yes
C17 . N2 . H21 . 123.2 no
C18 . N2 . H21 . 122.7 no
C9 . N3 . C10 . 116.2(8) yes
C9 . N3 . C11 . 107.3(7) yes
C10 . N3 . C11 . 116.1(7) yes
C2 . C1 . C9 . 116.4(8) yes
C2 . C1 . C19 . 118.2(7) yes
C9 . C1 . C19 . 101.7(7) yes
C2 . C1 . H11 . 106.8(14) no
C9 . C1 . H11 . 107.7(15) no
C19 . C1 . H11 . 105.2(15) no
C1 . C2 . C3 . 116.2(11) yes
C1 . C2 . C7 . 126.4(11) yes
C3 . C2 . C7 . 117.4(8) yes
C2 . C3 . C4 . 119.7(9) yes
C2 . C3 . H31 . 119.9(14) no
C4 . C3 . H31 . 120.5(14) no
C3 . C4 . C5 . 122.6(11) yes
C3 . C4 . H41 . 118.4(14) no
C5 . C4 . H41 . 119.0(14) no
C4 . C5 . C6 . 118.2(11) yes
C4 . C5 . C8 . 122.7(15) yes
C6 . C5 . C8 . 119.0(14) yes
C5 . C6 . C7 . 119.1(10) yes
C5 . C6 . H61 . 120.8(14) no
C7 . C6 . H61 . 120.1(14) no
C6 . C7 . C2 . 123.0(9) yes
C6 . C7 . H71 . 118.5(14) no
C2 . C7 . H71 . 118.6(13) no
C5 . C8 . H83 . 109.5(17) no
C5 . C8 . H81 . 109.1(16) no
H83 . C8 . H81 . 109.8(17) no
C5 . C8 . H82 . 109.1(17) no
H83 . C8 . H82 . 109.5(17) no
H81 . C8 . H82 . 109.8(17) no
C1 . C9 . N3 . 101.2(8) yes
C1 . C9 . H92 . 111.7(16) no
N3 . C9 . H92 . 111.2(16) no
C1 . C9 . H91 . 111.1(16) no
N3 . C9 . H91 . 112.1(16) no
H92 . C9 . H91 . 109.4(16) no
N3 . C10 . H103 . 109.5(16) no
N3 . C10 . H101 . 110.3(16) no
H103 . C10 . H101 . 109.3(17) no
N3 . C10 . H102 . 109.1(16) no
H103 . C10 . H102 . 109.3(17) no
H101 . C10 . H102 . 109.4(17) no
N3 . C11 . C12 . 110.1(7) yes
N3 . C11 . C18 . 111.7(7) yes
C12 . C11 . C18 . 101.4(7) yes
N3 . C11 . C19 . 103.6(6) yes
C12 . C11 . C19 . 116.4(7) yes
C18 . C11 . C19 . 113.9(7) yes
C11 . C12 . C13 . 132.1(8) yes
C11 . C12 . C17 . 110.2(8) yes
C13 . C12 . C17 . 117.4(8) yes
C12 . C13 . C14 . 119.6(8) yes
C12 . C13 . H131 . 120.7(13) no
C14 . C13 . H131 . 119.7(13) no
Cl1 . C14 . C13 . 120.6(9) yes
Cl1 . C14 . C15 . 117.0(9) yes
C13 . C14 . C15 . 122.4(8) yes
C14 . C15 . C16 . 118.7(8) yes
C14 . C15 . H151 . 120.7(13) no
C16 . C15 . H151 . 120.6(13) no
C15 . C16 . C17 . 118.1(7) yes
C15 . C16 . H161 . 120.7(13) no
C17 . C16 . H161 . 121.2(13) no
N2 . C17 . C12 . 108.7(8) yes
N2 . C17 . C16 . 127.5(9) yes
C12 . C17 . C16 . 123.7(8) yes
C11 . C18 . N2 . 107.2(7) yes
C11 . C18 . O2 . 126.3(9) yes
N2 . C18 . O2 . 126.1(8) yes
C1 . C19 . C11 . 104.0(7) yes
C1 . C19 . C20 . 111.4(6) yes
C11 . C19 . C20 . 111.6(6) yes
C1 . C19 . C31 . 112.5(6) yes
C11 . C19 . C31 . 111.4(6) yes
C20 . C19 . C31 . 106.1(6) yes
C19 . C20 . O1 . 119.9(8) yes
C19 . C20 . C21 . 119.2(7) yes
O1 . C20 . C21 . 120.9(8) yes
C20 . C21 . C22 . 117.1(7) yes
C20 . C21 . C30 . 118.0(8) yes
C22 . C21 . C30 . 125.0(7) yes
C21 . C22 . C23 . 129.9(7) yes
C21 . C22 . H221 . 115.2(13) no
C23 . C22 . H221 . 114.8(13) no
C22 . C23 . C24 . 125.2(8) yes
C22 . C23 . C28 . 118.3(9) yes
C24 . C23 . C28 . 116.3(8) yes
C23 . C24 . C25 . 120.1(8) yes
C23 . C24 . H241 . 119.9(13) no
C25 . C24 . H241 . 119.9(13) no
C24 . C25 . C26 . 123.1(8) yes
C24 . C25 . H251 . 118.1(13) no
C26 . C25 . H251 . 118.7(13) no
C25 . C26 . C27 . 117.5(9) yes
C25 . C26 . C29 . 121.1(12) yes
C27 . C26 . C29 . 121.3(11) yes
C26 . C27 . C28 . 120.9(8) yes
C26 . C27 . H271 . 119.4(13) no
C28 . C27 . H271 . 119.8(13) no
C23 . C28 . C27 . 122.0(8) yes
C23 . C28 . H281 . 118.6(13) no
C27 . C28 . H281 . 119.4(13) no
C26 . C29 . H292 . 109.8(16) no
C26 . C29 . H293 . 109.8(16) no
H292 . C29 . H293 . 109.8(17) no
C26 . C29 . H291 . 109.1(17) no
H292 . C29 . H291 . 109.0(17) no
H293 . C29 . H291 . 109.3(17) no
C21 . C30 . N1 . 112.8(7) yes
C21 . C30 . H301 . 109.2(15) no
N1 . C30 . H301 . 108.9(15) no
C21 . C30 . H302 . 107.3(15) no
N1 . C30 . H302 . 109.3(15) no
H301 . C30 . H302 . 109.4(16) no
C19 . C31 . N1 . 108.7(6) yes
C19 . C31 . H312 . 109.1(15) no
N1 . C31 . H312 . 110.3(15) no
C19 . C31 . H311 . 109.8(15) no
N1 . C31 . H311 . 109.5(15) no
H312 . C31 . H311 . 109.5(16) no
N1 . C32 . H322 . 110.1(16) no
N1 . C32 . H323 . 109.8(16) no
H322 . C32 . H323 . 109.2(16) no
N1 . C32 . H321 . 108.5(16) no
H322 . C32 . H321 . 109.9(16) no
H323 . C32 . H321 . 109.3(17) no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N2 . H21 . O2 2_666 163.2(3) 0.861 2.030 2.865(13) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 15/06/14 at 14:06:18
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT CL   (    1 ,X'S,U'S)  UNTIL C    (   32 ) 
CONT H    (  103 ,X'S)  UNTIL H    (   91 ) 
CONT H    (  151 ,X'S)  UNTIL H    (  131 ) 
RIDE N   (   2,X'S) H   (  21,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 15/06/14 at 14:06:18
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H1-N-R2 
DIST 0.86, 0.02 = 
CONT N ( 2) TO H(21) 
REST 0.084, 0.002 = H(21,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(21) TO N ( 2) TO C(17) 
CONT H(21) TO N ( 2) TO C(18) 
REM            1 H ON SP 3 
DIST 0.98, 0.02 = 
CONT C ( 1) TO H(11) 
REST 0.090, 0.002 = H(11,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(11) TO C ( 1) TO C(2) 
CONT H(11) TO C ( 1) TO C(9) 
CONT H(11) TO C ( 1) TO C(19) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 3) TO H(31) 
REST 0.137, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
PLANAR C ( 3) C(2) C(4) H(31) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 4) TO H(41) 
REST 0.148, 0.002 = H(41,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(41) TO C ( 4) TO C(3) 
CONT H(41) TO C ( 4) TO C(5) 
PLANAR C ( 4) C(3) C(5) H(41) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 6) TO H(61) 
REST 0.138, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO C ( 6) TO C(5) 
CONT H(61) TO C ( 6) TO C(7) 
PLANAR C ( 6) C(5) C(7) H(61) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 7) TO H(71) 
REST 0.116, 0.002 = H(71,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(71) TO C ( 7) TO C(6) 
CONT H(71) TO C ( 7) TO C(2) 
PLANAR C ( 7) C(6) C(2) H(71) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 8) TO H(83) 
CONT C ( 8) TO H(81) 
CONT C ( 8) TO H(82) 
REST 0.226, 0.002 = H(83,U[ISO]) 
REST 0.226, 0.002 = H(81,U[ISO]) 
REST 0.226, 0.002 = H(82,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(5) TO C ( 8) TO H(83) 
CONT C(5) TO C ( 8) TO H(81) 
CONT C(5) TO C ( 8) TO H(82) 
ANGLE 0.0, 2.0 = MEAN H(83) TO C ( 8) TO H(81) 
CONT H(83) TO C ( 8) TO H(82) 
CONT H(81) TO C ( 8) TO H(82) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 9) TO H(92) 
CONT C ( 9) TO H(91) 
REST 0.111, 0.002 = H(92,U[ISO]) 
REST 0.111, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(92) TO C ( 9) TO C(1) 
CONT H(92) TO C ( 9) TO N(3) 
CONT H(91) TO C ( 9) TO C(1) 
CONT H(91) TO C ( 9) TO N(3) 
ANGLE 109.54, 2.0 = 
CONT H(92) TO C ( 9) TO H(91) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 10) TO H(103) 
CONT C ( 10) TO H(101) 
CONT C ( 10) TO H(102) 
REST 0.177, 0.002 = H(103,U[ISO]) 
REST 0.177, 0.002 = H(101,U[ISO]) 
REST 0.177, 0.002 = H(102,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT N(3) TO C ( 10) TO H(103) 
CONT N(3) TO C ( 10) TO H(101) 
CONT N(3) TO C ( 10) TO H(102) 
ANGLE 0.0, 2.0 = MEAN H(103) TO C ( 10) TO H(101) 
CONT H(103) TO C ( 10) TO H(102) 
CONT H(101) TO C ( 10) TO H(102) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 13) TO H(131) 
REST 0.106, 0.002 = H(131,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(131) TO C ( 13) TO C(12) 
CONT H(131) TO C ( 13) TO C(14) 
PLANAR C ( 13) C(12) C(14) H(131) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 15) TO H(151) 
REST 0.114, 0.002 = H(151,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(151) TO C ( 15) TO C(14) 
CONT H(151) TO C ( 15) TO C(16) 
PLANAR C ( 15) C(14) C(16) H(151) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 16) TO H(161) 
REST 0.096, 0.002 = H(161,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(161) TO C ( 16) TO C(15) 
CONT H(161) TO C ( 16) TO C(17) 
PLANAR C ( 16) C(15) C(17) H(161) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 22) TO H(221) 
REST 0.086, 0.002 = H(221,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(221) TO C ( 22) TO C(21) 
CONT H(221) TO C ( 22) TO C(23) 
PLANAR C ( 22) C(21) C(23) H(221) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 24) TO H(241) 
REST 0.103, 0.002 = H(241,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(241) TO C ( 24) TO C(23) 
CONT H(241) TO C ( 24) TO C(25) 
PLANAR C ( 24) C(23) C(25) H(241) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 25) TO H(251) 
REST 0.128, 0.002 = H(251,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(251) TO C ( 25) TO C(24) 
CONT H(251) TO C ( 25) TO C(26) 
PLANAR C ( 25) C(24) C(26) H(251) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 27) TO H(271) 
REST 0.121, 0.002 = H(271,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(271) TO C ( 27) TO C(26) 
CONT H(271) TO C ( 27) TO C(28) 
PLANAR C ( 27) C(26) C(28) H(271) 
REM            1 H ON SP 2 
DIST 0.93, 0.02 = 
CONT C ( 28) TO H(281) 
REST 0.101, 0.002 = H(281,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(281) TO C ( 28) TO C(23) 
CONT H(281) TO C ( 28) TO C(27) 
PLANAR C ( 28) C(23) C(27) H(281) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 29) TO H(292) 
CONT C ( 29) TO H(293) 
CONT C ( 29) TO H(291) 
REST 0.250, 0.002 = H(292,U[ISO]) 
REST 0.250, 0.002 = H(293,U[ISO]) 
REST 0.250, 0.002 = H(291,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(26) TO C ( 29) TO H(292) 
CONT C(26) TO C ( 29) TO H(293) 
CONT C(26) TO C ( 29) TO H(291) 
ANGLE 0.0, 2.0 = MEAN H(292) TO C ( 29) TO H(293) 
CONT H(292) TO C ( 29) TO H(291) 
CONT H(293) TO C ( 29) TO H(291) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 30) TO H(301) 
CONT C ( 30) TO H(302) 
REST 0.078, 0.002 = H(301,U[ISO]) 
REST 0.078, 0.002 = H(302,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(301) TO C ( 30) TO C(21) 
CONT H(301) TO C ( 30) TO N(1) 
CONT H(302) TO C ( 30) TO C(21) 
CONT H(302) TO C ( 30) TO N(1) 
ANGLE 109.54, 2.0 = 
CONT H(301) TO C ( 30) TO H(302) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 31) TO H(312) 
CONT C ( 31) TO H(311) 
REST 0.087, 0.002 = H(312,U[ISO]) 
REST 0.087, 0.002 = H(311,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(312) TO C ( 31) TO C(19) 
CONT H(312) TO C ( 31) TO N(1) 
CONT H(311) TO C ( 31) TO C(19) 
CONT H(311) TO C ( 31) TO N(1) 
ANGLE 109.54, 2.0 = 
CONT H(312) TO C ( 31) TO H(311) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 32) TO H(322) 
CONT C ( 32) TO H(323) 
CONT C ( 32) TO H(321) 
REST 0.125, 0.002 = H(322,U[ISO]) 
REST 0.125, 0.002 = H(323,U[ISO]) 
REST 0.125, 0.002 = H(321,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT N(1) TO C ( 32) TO H(322) 
CONT N(1) TO C ( 32) TO H(323) 
CONT N(1) TO C ( 32) TO H(321) 
ANGLE 0.0, 2.0 = MEAN H(322) TO C ( 32) TO H(323) 
CONT H(322) TO C ( 32) TO H(321) 
CONT H(323) TO C ( 32) TO H(321) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-butanol'
