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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_pk276
_database_code_depnum_ccdc_archive 'CCDC 1044484'
_audit_update_record             
;
2015-01-20 deposited with the CCDC.
2015-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
1-(2,5-Dihydro-1-1H-pyrrol-1-yl)-3-iodoprop-2-yn-1-one
_chemical_name_common            ?
_chemical_melting_point          441
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H6 I N O'
_chemical_formula_weight         247.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'


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                   10.5832(5)
_cell_length_b                   15.6631(6)
_cell_length_c                   9.8457(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.447(5)
_cell_angle_gamma                90.00
_cell_volume                     1621.77(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    1987
_cell_measurement_theta_min      3.8700
_cell_measurement_theta_max      28.3610


_exptl_crystal_description       'thin platelet'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.023
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    3.880
_exptl_absorpt_correction_T_min  0.82549
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180(2)
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.3385
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3819
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0370
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         25.67
_reflns_number_total             1542
_reflns_number_gt                1270
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0383P)²+5.4810P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1542
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0843
_refine_ls_wR_factor_gt          0.0780
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I I 0.78585(3) 0.47051(2) 0.23780(4) 0.03855(16) Uani 1 1 d . . .
O O 0.7951(3) 0.8073(2) 0.1981(4) 0.0400(9) Uani 1 1 d . . .
N N 0.9445(4) 0.7769(3) 0.0584(4) 0.0312(10) Uani 1 1 d . . .
C1 C 0.8579(4) 0.7551(3) 0.1402(5) 0.0268(11) Uani 1 1 d . . .
C2 C 0.8409(4) 0.6640(3) 0.1625(5) 0.0311(11) Uani 1 1 d . . .
C3 C 0.8250(5) 0.5908(3) 0.1888(6) 0.0357(12) Uani 1 1 d . . .
C4 C 1.0205(5) 0.7184(4) -0.0167(6) 0.0418(13) Uani 1 1 d . . .
H4A H 0.9658 0.6825 -0.0820 0.063 Uiso 1 1 calc R . .
H4B H 1.0752 0.6811 0.0463 0.063 Uiso 1 1 calc R . .
C5 C 1.0975(5) 0.7794(5) -0.0890(6) 0.0490(16) Uani 1 1 d . . .
H5 H 1.1582 0.7624 -0.1479 0.059 Uiso 1 1 calc R . .
C6 C 1.0722(6) 0.8593(5) -0.0621(6) 0.0494(16) Uani 1 1 d . . .
H6 H 1.1124 0.9068 -0.0990 0.059 Uiso 1 1 calc R . .
C7 C 0.9725(5) 0.8666(3) 0.0332(6) 0.0368(13) Uani 1 1 d . . .
H7A H 1.0054 0.8962 0.1188 0.055 Uiso 1 1 calc R . .
H7B H 0.8964 0.8971 -0.0099 0.055 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I 0.0386(2) 0.0260(2) 0.0517(3) 0.00091(16) 0.00794(17) 0.00183(15)
O 0.042(2) 0.031(2) 0.050(2) -0.0051(18) 0.0191(18) -0.0014(17)
N 0.034(2) 0.029(2) 0.032(2) -0.0011(19) 0.0103(18) -0.0036(19)
C1 0.028(2) 0.025(3) 0.027(3) 0.000(2) 0.005(2) -0.003(2)
C2 0.027(2) 0.033(3) 0.034(3) -0.006(2) 0.006(2) 0.000(2)
C3 0.038(3) 0.018(2) 0.052(3) -0.002(2) 0.007(2) -0.001(2)
C4 0.042(3) 0.045(3) 0.040(3) -0.007(3) 0.014(3) 0.003(3)
C5 0.044(3) 0.072(5) 0.033(3) -0.007(3) 0.014(3) -0.009(3)
C6 0.048(3) 0.064(4) 0.037(3) 0.007(3) 0.008(3) -0.023(3)
C7 0.036(3) 0.033(3) 0.042(3) 0.009(2) 0.004(2) -0.009(2)

_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
I C3 1.999(5) . ?
O C1 1.233(6) . ?
N C1 1.331(6) . ?
N C7 1.463(6) . ?
N C4 1.472(7) . ?
C1 C2 1.458(7) . ?
C2 C3 1.192(7) . ?
C4 C5 1.488(8) . ?
C5 C6 1.313(9) . ?
C6 C7 1.493(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N C7 121.0(4) . . ?
C1 N C4 126.7(4) . . ?
C7 N C4 112.3(4) . . ?
O C1 N 123.6(4) . . ?
O C1 C2 119.8(4) . . ?
N C1 C2 116.6(4) . . ?
C3 C2 C1 175.8(6) . . ?
C2 C3 I 175.7(5) . . ?
N C4 C5 101.5(4) . . ?
C6 C5 C4 112.4(5) . . ?
C5 C6 C7 112.0(5) . . ?
N C7 C6 101.7(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
C7 N C1 O 1.1(8) . . . . ?
C4 N C1 O -178.3(5) . . . . ?
C7 N C1 C2 -177.7(4) . . . . ?
C4 N C1 C2 2.9(8) . . . . ?
C1 N C4 C5 179.7(5) . . . . ?
C7 N C4 C5 0.3(6) . . . . ?
N C4 C5 C6 0.0(7) . . . . ?
C4 C5 C6 C7 -0.2(8) . . . . ?
C1 N C7 C6 -179.8(5) . . . . ?
C4 N C7 C6 -0.4(6) . . . . ?
C5 C6 C7 N 0.4(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.67
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.032
_refine_diff_density_min         -0.850
_refine_diff_density_rms         0.128
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
####################################################################### 
# 
# 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_pk248
_database_code_depnum_ccdc_archive 'CCDC 1044485'
_audit_update_record             
;
2015-01-20 deposited with the CCDC.
2015-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        3-Iodo-1-(pyrrolidin-1-yl)prop-2-yn-1-one
_chemical_name_common            ?
_chemical_melting_point          425
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H8 I N O'
_chemical_formula_weight         249.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+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                   10.3440(3)
_cell_length_b                   15.8341(5)
_cell_length_c                   10.4832(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.996(3)
_cell_angle_gamma                90
_cell_volume                     1707.63(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    179.95(10)
_cell_measurement_reflns_used    1615
_cell_measurement_theta_min      3.9110
_cell_measurement_theta_max      25.6900
_exptl_crystal_description       'prismatic, cut from larger crystal'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.937
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    3.686
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.98118
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      179.95(10)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            4166
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.930
_diffrn_reflns_theta_max         27.102
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1855
_reflns_number_gt                1416
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0203P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1855
_refine_ls_number_parameters     110
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0680
_refine_ls_wR_factor_gt          0.0571
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I 0.21833(3) 1.02479(2) 0.25814(3) 0.03834(13) Uani 1 1 d . . . . .
O O 0.2136(3) 0.6898(2) 0.2884(3) 0.0406(8) Uani 1 1 d . . . . .
N N 0.0688(3) 0.7193(3) 0.4289(3) 0.0330(9) Uani 1 1 d . . . . .
C1 C 0.1515(4) 0.7420(3) 0.3453(4) 0.0293(10) Uani 1 1 d . . . . .
C2 C 0.1673(4) 0.8318(3) 0.3244(4) 0.0340(11) Uani 1 1 d . . . . .
C3 C 0.1825(4) 0.9038(3) 0.2994(4) 0.0374(11) Uani 1 1 d . . . . .
C4 C 0.0418(4) 0.6310(3) 0.4548(4) 0.0398(12) Uani 1 1 d D . . . .
H4A H 0.1199 0.6008 0.4938 0.048 Uiso 1 1 calc R U . A 1
H4B H 0.0045 0.6008 0.3768 0.048 Uiso 1 1 calc R U . A 1
C5A C -0.058(3) 0.644(3) 0.550(3) 0.056(11) Uani 0.435(14) 1 d D . P B 1
H5A1 H -0.0539 0.5976 0.6133 0.067 Uiso 0.435(14) 1 calc R U P B 1
H5A2 H -0.1471 0.6460 0.5048 0.067 Uiso 0.435(14) 1 calc R U P B 1
C6A C -0.0262(11) 0.7319(8) 0.6220(10) 0.040(4) Uani 0.435(14) 1 d D . P B 1
H6A1 H -0.1001 0.7543 0.6647 0.048 Uiso 0.435(14) 1 calc R U P B 1
H6A2 H 0.0533 0.7295 0.6833 0.048 Uiso 0.435(14) 1 calc R U P B 1
C5B C -0.048(3) 0.631(3) 0.562(2) 0.057(9) Uani 0.565(14) 1 d D . P B 2
H5B1 H -0.1078 0.5814 0.5553 0.069 Uiso 0.565(14) 1 calc R U P B 2
H5B2 H 0.0013 0.6313 0.6482 0.069 Uiso 0.565(14) 1 calc R U P B 2
C6B C -0.1179(10) 0.7091(8) 0.5351(11) 0.062(4) Uani 0.565(14) 1 d D . P B 2
H6B1 H -0.1612 0.7276 0.6102 0.074 Uiso 0.565(14) 1 calc R U P B 2
H6B2 H -0.1845 0.7024 0.4607 0.074 Uiso 0.565(14) 1 calc R U P B 2
C7 C -0.0065(4) 0.7774(4) 0.5029(4) 0.0453(14) Uani 1 1 d D . . . .
H7A H 0.0421 0.8305 0.5224 0.054 Uiso 1 1 calc R U . B 1
H7B H -0.0911 0.7911 0.4542 0.054 Uiso 1 1 calc R U . B 1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I 0.0403(2) 0.0290(2) 0.0462(2) 0.00125(16) 0.00687(14) 0.00052(14)
O 0.050(2) 0.0287(19) 0.047(2) -0.0044(16) 0.0245(15) -0.0043(16)
N 0.0314(19) 0.041(3) 0.027(2) -0.0022(18) 0.0068(15) -0.0035(18)
C1 0.025(2) 0.033(3) 0.029(3) -0.003(2) 0.0017(18) -0.006(2)
C2 0.033(2) 0.038(3) 0.031(3) -0.006(2) 0.0045(18) -0.001(2)
C3 0.037(3) 0.036(3) 0.038(3) -0.003(2) 0.001(2) -0.001(2)
C4 0.045(3) 0.045(3) 0.029(3) 0.002(2) 0.002(2) -0.012(3)
C5A 0.051(15) 0.08(3) 0.033(13) 0.028(13) 0.004(10) -0.037(14)
C6A 0.046(7) 0.045(8) 0.030(7) 0.003(6) 0.011(5) 0.002(6)
C5B 0.086(17) 0.060(13) 0.030(11) -0.017(13) 0.028(10) -0.034(10)
C6B 0.058(7) 0.086(10) 0.045(7) 0.007(6) 0.023(6) 0.011(7)
C7 0.035(3) 0.060(4) 0.044(3) -0.006(3) 0.015(2) 0.005(3)

_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
I C3 2.007(5) . ?
O C1 1.237(5) . ?
N C1 1.337(5) . ?
N C4 1.457(6) . ?
N C7 1.476(6) . ?
C1 C2 1.451(7) . ?
C2 C3 1.184(7) . ?
C4 C5A 1.530(17) . ?
C4 C5B 1.535(14) . ?
C5A C6A 1.59(5) . ?
C6A C7 1.474(10) . ?
C5B C6B 1.45(4) . ?
C6B C7 1.641(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N C4 121.9(4) . . ?
C1 N C7 125.9(4) . . ?
C4 N C7 112.2(3) . . ?
O C1 N 122.5(4) . . ?
O C1 C2 120.6(4) . . ?
N C1 C2 116.9(4) . . ?
C3 C2 C1 175.6(5) . . ?
C2 C3 I 177.0(4) . . ?
N C4 C5A 98(2) . . ?
N C4 C5B 106.5(15) . . ?
C4 C5A C6A 108(2) . . ?
C7 C6A C5A 93.8(16) . . ?
C6B C5B C4 100(2) . . ?
C5B C6B C7 105.1(12) . . ?
C6A C7 N 105.6(6) . . ?
N C7 C6B 96.8(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
C4 N C1 O -2.7(7) . . . . ?
C7 N C1 O 178.5(4) . . . . ?
C4 N C1 C2 178.0(4) . . . . ?
C7 N C1 C2 -0.8(6) . . . . ?
C1 N C4 C5A -178.3(16) . . . . ?
C7 N C4 C5A 0.6(16) . . . . ?
C1 N C4 C5B 175.8(13) . . . . ?
C7 N C4 C5B -5.3(14) . . . . ?
N C4 C5A C6A -29(3) . . . . ?
C4 C5A C6A C7 45(3) . . . . ?
N C4 C5B C6B 30.9(18) . . . . ?
C4 C5B C6B C7 -43.1(17) . . . . ?
C5A C6A C7 N -42.4(14) . . . . ?
C1 N C7 C6A -151.3(6) . . . . ?
C4 N C7 C6A 29.8(7) . . . . ?
C1 N C7 C6B 159.6(6) . . . . ?
C4 N C7 C6B -19.3(6) . . . . ?
C5B C6B C7 N 39.5(12) . . . . ?

_refine_diff_density_max         0.600
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.122

_shelxl_version_number           2014/6

_shelx_res_file                  
;
TITL PK248 C7H8INO C2/c OD MAR14
CELL 0.71073  10.343959  15.834100  10.483249  90.0000  95.9963  90.0000
ZERR   8.00   0.000346   0.000510   0.000385   0.0000   0.0029   0.0000
LATT 7
SYMM  x,-y, z+1/2
SFAC C H N O I
UNIT 56 64 8 8 8
MORE 1
TEMP -93
SHEL 11. 0.78
L.S. 8
BOND
FMAP 2
PLAN -10
DFIX  1.54 0.02 C4 C5A C4 C5B C6A C6B C7 C6A C7 C6B
CONF
ACTA
WGHT    0.020300
FVAR       1.58565   0.43468
MOLE   1
I     5    0.218328    1.024789    0.258135    11.00000    0.04028    0.02902 =
         0.04622    0.00125    0.00687    0.00052
O     4    0.213565    0.689805    0.288419    11.00000    0.05002    0.02868 =
         0.04707   -0.00444    0.02452   -0.00432
N     3    0.068765    0.719339    0.428939    11.00000    0.03143    0.04139 =
         0.02711   -0.00216    0.00682   -0.00354
C1    1    0.151495    0.741986    0.345288    11.00000    0.02536    0.03276 =
         0.02947   -0.00274    0.00168   -0.00649
C2    1    0.167325    0.831816    0.324377    11.00000    0.03291    0.03834 =
         0.03098   -0.00629    0.00453   -0.00103
C3    1    0.182503    0.903826    0.299388    11.00000    0.03725    0.03631 =
         0.03796   -0.00274    0.00093   -0.00116
C4    1    0.041769    0.631030    0.454799    11.00000    0.04502    0.04484 =
         0.02934    0.00240    0.00240   -0.01150
AFIX  23
H4A   2    0.119916    0.600831    0.493784    11.00000   -1.20000
H4B   2    0.004509    0.600786    0.376834    11.00000   -1.20000
AFIX   0
PART 1
C5A   1   -0.058403    0.644463    0.550430    21.00000    0.05062    0.08462 =
         0.03316    0.02831    0.00397   -0.03702
AFIX  23
H5A1  2   -0.053884    0.597638    0.613319    21.00000   -1.20000
H5A2  2   -0.147147    0.645959    0.504824    21.00000   -1.20000
AFIX   0
C6A   1   -0.026219    0.731948    0.622049    21.00000    0.04568    0.04534 =
         0.03011    0.00290    0.01077    0.00164
AFIX  23
H6A1  2   -0.100060    0.754280    0.664735    21.00000   -1.20000
H6A2  2    0.053270    0.729509    0.683347    21.00000   -1.20000
AFIX   0
PART 2
C5B   1   -0.048454    0.630637    0.562180   -21.00000    0.08595    0.06002 =
         0.03013   -0.01718    0.02800   -0.03356
AFIX  23
H5B1  2   -0.107776    0.581408    0.555347   -21.00000   -1.20000
H5B2  2    0.001258    0.631293    0.648159   -21.00000   -1.20000
AFIX   0
C6B   1   -0.117949    0.709057    0.535059   -21.00000    0.05848    0.08622 =
         0.04499    0.00702    0.02299    0.01146
AFIX  23
H6B1  2   -0.161205    0.727557    0.610197   -21.00000   -1.20000
H6B2  2   -0.184515    0.702433    0.460736   -21.00000   -1.20000
AFIX   0
PART 0

C7    1   -0.006534    0.777363    0.502915    11.00000    0.03480    0.05964 =
         0.04362   -0.00629    0.01469    0.00496
AFIX  23
H7A   2    0.042093    0.830464    0.522357    11.00000   -1.20000
H7B   2   -0.091076    0.791143    0.454172    11.00000   -1.20000
AFIX   0
HKLF 4

REM  PK248 C7H8INO C2/c OD MAR14
REM R1 =  0.0336 for    1416 Fo > 4sig(Fo)  and  0.0530 for all    1855 data
REM    110 parameters refined using      5 restraints

END

WGHT      0.0182      0.0000

REM Highest difference peak  0.600,  deepest hole -0.489,  1-sigma level  0.122
Q1    1   0.1763  1.0260  0.3212  11.00000  0.05    0.60
Q2    1   0.0614  0.7841  0.5625  11.00000  0.05    0.60
Q3    1   0.3366  1.0239  0.2118  11.00000  0.05    0.57
Q4    1  -0.0446  0.7276  0.5954  11.00000  0.05    0.52
Q5    1   0.1805  0.5878  0.4917  11.00000  0.05    0.48
Q6    1   0.1562  1.0775  0.1481  11.00000  0.05    0.47
Q7    1  -0.0513  0.8279  0.4324  11.00000  0.05    0.40
Q8    1   0.1608  0.8158  0.5350  11.00000  0.05    0.40
Q9    1  -0.0730  0.6467  0.4964  11.00000  0.05    0.40
Q10   1   0.1886  1.0124  0.0851  11.00000  0.05    0.40
;
_shelx_res_checksum              17569

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
####################################################################### 
# 
# 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_pk257_Abs
_database_code_depnum_ccdc_archive 'CCDC 1044486'
_audit_update_record             
;
2015-01-20 deposited with the CCDC.
2015-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        3-Iodo-1-(piperidin-1-yl)prop-2-yn-1-one
_chemical_name_common            ?
_chemical_melting_point          394
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H10 I N O'
_chemical_formula_weight         263.07

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   9.1784(3)
_cell_length_b                   8.6829(3)
_cell_length_c                   11.5199(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.699(3)
_cell_angle_gamma                90
_cell_volume                     917.07(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.1(5)
_cell_measurement_reflns_used    2383
_cell_measurement_theta_min      4.0880
_cell_measurement_theta_max      28.0720


_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    3.437
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.586
_exptl_absorpt_correction_T_max  0.818
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      150.1(5)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            4888
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.939
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1876
_reflns_number_gt                1566
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0124P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1876
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0462
_refine_ls_wR_factor_gt          0.0423
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I 0.35820(2) 1.30059(3) 1.04396(2) 0.02082(8) Uani 1 1 d . . . . .
O O 0.3807(3) 0.9351(3) 0.67578(18) 0.0280(6) Uani 1 1 d . . . . .
N N 0.2814(3) 0.7647(3) 0.7980(2) 0.0173(6) Uani 1 1 d . . . . .
C1 C 0.3323(3) 0.9039(4) 0.7716(3) 0.0181(7) Uani 1 1 d . . . . .
C2 C 0.3299(3) 1.0214(4) 0.8610(3) 0.0213(8) Uani 1 1 d . . . . .
C3 C 0.3394(3) 1.1252(4) 0.9296(3) 0.0231(8) Uani 1 1 d . . . . .
C4 C 0.2852(3) 0.6378(4) 0.7158(3) 0.0216(8) Uani 1 1 d . . . . .
H4A H 0.3478 0.5543 0.7488 0.026 Uiso 1 1 calc R U . . .
H4B H 0.3273 0.6736 0.6430 0.026 Uiso 1 1 calc R U . . .
C5 C 0.1321(4) 0.5770(4) 0.6898(3) 0.0246(8) Uani 1 1 d . . . . .
H5A H 0.1360 0.4874 0.6368 0.030 Uiso 1 1 calc R U . . .
H5B H 0.0719 0.6579 0.6504 0.030 Uiso 1 1 calc R U . . .
C6 C 0.0623(4) 0.5289(4) 0.8017(3) 0.0275(8) Uani 1 1 d . . . . .
H6A H -0.0399 0.4969 0.7843 0.033 Uiso 1 1 calc R U . . .
H6B H 0.1159 0.4400 0.8366 0.033 Uiso 1 1 calc R U . . .
C7 C 0.0659(4) 0.6625(4) 0.8874(3) 0.0266(9) Uani 1 1 d . . . . .
H7A H 0.0009 0.7455 0.8566 0.032 Uiso 1 1 calc R U . . .
H7B H 0.0281 0.6272 0.9620 0.032 Uiso 1 1 calc R U . . .
C8 C 0.2182(4) 0.7264(4) 0.9092(3) 0.0242(8) Uani 1 1 d . . . . .
H8A H 0.2143 0.8199 0.9582 0.029 Uiso 1 1 calc R U . . .
H8B H 0.2801 0.6493 0.9512 0.029 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I 0.02155(13) 0.01767(14) 0.02331(14) -0.00216(10) 0.00186(8) 0.00035(10)
O 0.0413(15) 0.0222(15) 0.0212(13) 0.0062(11) 0.0102(11) -0.0020(12)
N 0.0182(14) 0.0148(17) 0.0187(14) 0.0008(12) 0.0014(11) -0.0032(12)
C1 0.0166(17) 0.016(2) 0.0213(18) 0.0014(15) -0.0030(13) 0.0023(15)
C2 0.0227(19) 0.018(2) 0.0233(19) 0.0023(16) 0.0021(14) -0.0025(15)
C3 0.0211(18) 0.024(2) 0.0245(19) 0.0048(17) 0.0019(14) 0.0001(16)
C4 0.0249(18) 0.018(2) 0.0223(18) -0.0014(15) 0.0050(14) 0.0002(15)
C5 0.031(2) 0.019(2) 0.0231(18) -0.0049(16) -0.0032(14) -0.0023(17)
C6 0.0255(19) 0.024(2) 0.033(2) 0.0031(17) 0.0008(15) -0.0065(17)
C7 0.0263(19) 0.025(2) 0.029(2) 0.0041(16) 0.0108(15) -0.0025(16)
C8 0.034(2) 0.027(2) 0.0128(17) 0.0037(15) 0.0050(14) -0.0055(17)

_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
I C3 2.016(4) . ?
O C1 1.239(3) . ?
N C1 1.336(4) . ?
N C4 1.454(4) . ?
N C8 1.469(4) . ?
C1 C2 1.450(5) . ?
C2 C3 1.199(5) . ?
C4 C5 1.518(4) . ?
C5 C6 1.525(4) . ?
C6 C7 1.523(5) . ?
C7 C8 1.514(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N C4 121.2(3) . . ?
C1 N C8 124.1(3) . . ?
C4 N C8 114.8(3) . . ?
O C1 N 123.0(3) . . ?
O C1 C2 119.7(3) . . ?
N C1 C2 117.2(3) . . ?
C3 C2 C1 173.5(3) . . ?
C2 C3 I 179.1(3) . . ?
N C4 C5 110.0(3) . . ?
C4 C5 C6 110.5(3) . . ?
C7 C6 C5 110.0(3) . . ?
C8 C7 C6 112.2(3) . . ?
N C8 C7 109.7(3) . . ?

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
C4 N C1 O 2.5(5) . . . . ?
C8 N C1 O -177.5(3) . . . . ?
C4 N C1 C2 -177.3(3) . . . . ?
C8 N C1 C2 2.7(4) . . . . ?
C1 N C4 C5 -121.8(3) . . . . ?
C8 N C4 C5 58.2(4) . . . . ?
N C4 C5 C6 -56.5(4) . . . . ?
C4 C5 C6 C7 55.1(4) . . . . ?
C5 C6 C7 C8 -54.1(4) . . . . ?
C1 N C8 C7 123.9(3) . . . . ?
C4 N C8 C7 -56.1(4) . . . . ?
C6 C7 C8 N 53.1(4) . . . . ?


_refine_diff_density_max         0.442
_refine_diff_density_min         -0.542
_refine_diff_density_rms         0.116

_shelxl_version_number           2014/6

_shelx_res_file                  
;
TITL PK257 C810NOI P2(1)/c OD APR14
REM P2(1)/c (#14 in standard setting)
CELL 0.71073   9.178398   8.682930  11.519928  90.0000  92.6990  90.0000
ZERR    4.00   0.000325   0.000317   0.000405   0.0000   0.0029   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2
SFAC C H N O I
UNIT 32.00 40.00 4.00 4.00 4.00
EQIV $1 x, 2.5-y, 0.5+z
MORE 0
TEMP -93
SHEL 11. 0.80
L.S. 4
BOND
FMAP 2
PLAN -10
HTAB I O_$1
CONF
ACTA
WGHT    0.012400
FVAR       4.37195
MOLE   1
I     5    0.358199    1.300592    1.043962    11.00000    0.02155    0.01767 =
         0.02331   -0.00216    0.00186    0.00035
O     4    0.380679    0.935129    0.675783    11.00000    0.04132    0.02221 =
         0.02122    0.00618    0.01017   -0.00205
N     3    0.281384    0.764711    0.798034    11.00000    0.01824    0.01485 =
         0.01874    0.00076    0.00141   -0.00318
C1    1    0.332312    0.903868    0.771630    11.00000    0.01659    0.01614 =
         0.02135    0.00144   -0.00300    0.00234
C2    1    0.329880    1.021414    0.860959    11.00000    0.02268    0.01809 =
         0.02328    0.00232    0.00209   -0.00247
C3    1    0.339354    1.125193    0.929600    11.00000    0.02110    0.02383 =
         0.02446    0.00478    0.00186    0.00013
C4    1    0.285192    0.637825    0.715831    11.00000    0.02494    0.01799 =
         0.02234   -0.00140    0.00498    0.00025
AFIX  23
H4A   2    0.347826    0.554303    0.748799    11.00000   -1.20000
H4B   2    0.327329    0.673578    0.643018    11.00000   -1.20000
AFIX   0
C5    1    0.132054    0.576992    0.689765    11.00000    0.03104    0.01927 =
         0.02314   -0.00488   -0.00321   -0.00226
AFIX  23
H5A   2    0.135995    0.487432    0.636822    11.00000   -1.20000
H5B   2    0.071917    0.657881    0.650392    11.00000   -1.20000
AFIX   0
C6    1    0.062324    0.528862    0.801737    11.00000    0.02546    0.02386 =
         0.03319    0.00314    0.00077   -0.00649
AFIX  23
H6A   2   -0.039904    0.496903    0.784271    11.00000   -1.20000
H6B   2    0.115894    0.439964    0.836579    11.00000   -1.20000
AFIX   0
C7    1    0.065855    0.662537    0.887437    11.00000    0.02632    0.02514 =
         0.02918    0.00410    0.01081   -0.00254
AFIX  23
H7A   2    0.000927    0.745511    0.856647    11.00000   -1.20000
H7B   2    0.028075    0.627172    0.961985    11.00000   -1.20000
AFIX   0
C8    1    0.218197    0.726446    0.909229    11.00000    0.03375    0.02659 =
         0.01277    0.00371    0.00504   -0.00555
AFIX  23
H8A   2    0.214341    0.819938    0.958178    11.00000   -1.20000
H8B   2    0.280146    0.649250    0.951165    11.00000   -1.20000

AFIX   0
HKLF 4

REM  PK257 C810NOI P2(1)/c OD APR14
REM R1 =  0.0252 for    1566 Fo > 4sig(Fo)  and  0.0348 for all    1876 data
REM    100 parameters refined using      0 restraints

END

WGHT      0.0125      0.0000

REM Highest difference peak  0.442,  deepest hole -0.542,  1-sigma level  0.116
Q1    1   0.2236  0.7446  0.8374  11.00000  0.05    0.44
Q2    1   0.3991  1.5186  0.9797  11.00000  0.05    0.43
Q3    1   0.2401  1.3895  0.9395  11.00000  0.05    0.43
Q4    1   0.2119  1.1873  0.8324  11.00000  0.05    0.42
Q5    1   0.1440  0.3823  0.6359  11.00000  0.05    0.39
Q6    1   0.3009  1.5201  1.0423  11.00000  0.05    0.39
Q7    1  -0.0869  0.4731  0.7964  11.00000  0.05    0.38
Q8    1   0.3413  1.0052  0.9208  11.00000  0.05    0.37
Q9    1   0.0155  0.7875  0.8001  11.00000  0.05    0.37
Q10   1   0.2883  1.1044  0.9619  11.00000  0.05    0.36
;
_shelx_res_checksum              51868

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
####################################################################### 
# 
# 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_pk254
_database_code_depnum_ccdc_archive 'CCDC 1044487'
_audit_update_record             
;
2015-01-20 deposited with the CCDC.
2015-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        3-Iodo-1-(morpholin-4-yl)prop-2-yn-1-one
_chemical_name_common            ?
_chemical_melting_point          378
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H8 I N O2'
_chemical_formula_weight         265.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.7638(3)
_cell_length_b                   8.5910(3)
_cell_length_c                   11.4989(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.488(4)
_cell_angle_gamma                90
_cell_volume                     848.40(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2294
_cell_measurement_theta_min      3.5620
_cell_measurement_theta_max      28.6170

_exptl_crystal_description       'block-shaped, cut from larger crystal'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.075
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    3.725
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.87353
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector_area_resol_mean 10.3385
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3984
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0422
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         26.37
_reflns_number_total             1725
_reflns_number_gt                1495
_reflns_threshold_expression     >2sigma(I)
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0158P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1725
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0241
_refine_ls_wR_factor_ref         0.0497
_refine_ls_wR_factor_gt          0.0457
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I 0.65129(2) 0.19738(3) 0.47471(2) 0.02151(9) Uani 1 1 d . . . . .
O1 O 0.6331(3) 0.5707(3) 0.83837(18) 0.0309(6) Uani 1 1 d . . . . .
O2 O 0.9422(3) 0.9969(3) 0.7377(2) 0.0276(6) Uani 1 1 d . . . . .
N N 0.7377(3) 0.7405(4) 0.7266(2) 0.0181(6) Uani 1 1 d . . . . .
C1 C 0.6844(3) 0.6003(4) 0.7482(3) 0.0186(8) Uani 1 1 d . . . . .
C2 C 0.6838(4) 0.4810(5) 0.6585(3) 0.0211(8) Uani 1 1 d . . . . .
C3 C 0.6715(4) 0.3765(5) 0.5892(3) 0.0233(8) Uani 1 1 d . . . . .
C4 C 0.7261(4) 0.8735(4) 0.8042(3) 0.0213(8) Uani 1 1 d . . . . .
H4A H 0.6894 0.8380 0.8758 0.026 Uiso 1 1 calc R U . . .
H4B H 0.6501 0.9498 0.7620 0.026 Uiso 1 1 calc R U . . .
C5 C 0.8844(4) 0.9491(5) 0.8397(3) 0.0266(9) Uani 1 1 d . . . . .
H5A H 0.8765 1.0407 0.8904 0.032 Uiso 1 1 calc R U . . .
H5B H 0.9581 0.8744 0.8865 0.032 Uiso 1 1 calc R U . . .
C6 C 0.9598(4) 0.8641(5) 0.6672(3) 0.0266(9) Uani 1 1 d . . . . .
H6A H 1.0357 0.7918 0.7145 0.032 Uiso 1 1 calc R U . . .
H6B H 1.0025 0.8977 0.5977 0.032 Uiso 1 1 calc R U . . .
C7 C 0.8085(4) 0.7790(4) 0.6243(3) 0.0218(8) Uani 1 1 d . . . . .
H7A H 0.7366 0.8453 0.5678 0.026 Uiso 1 1 calc R U . . .
H7B H 0.8280 0.6824 0.5826 0.026 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I 0.02297(14) 0.01713(16) 0.02476(13) -0.00334(10) 0.00556(10) -0.00036(10)
O1 0.0488(16) 0.0234(17) 0.0245(12) 0.0041(12) 0.0166(12) -0.0043(14)
O2 0.0272(13) 0.0180(15) 0.0391(13) -0.0030(12) 0.0103(11) -0.0049(12)
N 0.0200(15) 0.0161(18) 0.0184(13) -0.0002(13) 0.0046(11) 0.0000(13)
C1 0.0166(17) 0.016(2) 0.0214(16) -0.0017(16) -0.0008(14) 0.0029(16)
C2 0.0216(17) 0.016(2) 0.0262(17) 0.0011(17) 0.0056(14) -0.0028(16)
C3 0.0219(18) 0.020(2) 0.0279(18) 0.0021(17) 0.0036(15) 0.0014(17)
C4 0.0267(19) 0.016(2) 0.0224(16) -0.0039(16) 0.0066(14) 0.0005(17)
C5 0.0292(19) 0.021(2) 0.0292(18) -0.0085(17) 0.0044(15) -0.0011(18)
C6 0.028(2) 0.020(2) 0.0349(19) -0.0038(18) 0.0125(16) -0.0020(18)
C7 0.0263(19) 0.022(2) 0.0189(16) 0.0004(16) 0.0098(14) 0.0012(17)

_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
I C3 2.010(4) . ?
O1 C1 1.236(3) . ?
O2 C6 1.426(4) . ?
O2 C5 1.428(4) . ?
N C1 1.333(5) . ?
N C4 1.465(4) . ?
N C7 1.473(4) . ?
C1 C2 1.453(5) . ?
C2 C3 1.191(5) . ?
C4 C5 1.512(5) . ?
C6 C7 1.508(5) . ?

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
C6 O2 C5 109.5(3) . . ?
C1 N C4 121.4(2) . . ?
C1 N C7 124.8(3) . . ?
C4 N C7 113.7(3) . . ?
O1 C1 N 122.8(3) . . ?
O1 C1 C2 120.0(3) . . ?
N C1 C2 117.2(3) . . ?
C3 C2 C1 173.5(4) . . ?
C2 C3 I 179.0(3) . . ?
N C4 C5 109.1(3) . . ?
O2 C5 C4 111.0(3) . . ?
O2 C6 C7 112.7(3) . . ?
N C7 C6 109.3(3) . . ?

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
C4 N C1 O1 -5.5(5) . . . . ?
C7 N C1 O1 176.2(3) . . . . ?
C4 N C1 C2 172.6(3) . . . . ?
C7 N C1 C2 -5.8(5) . . . . ?
C1 N C4 C5 128.6(3) . . . . ?
C7 N C4 C5 -52.9(4) . . . . ?
C6 O2 C5 C4 -61.6(4) . . . . ?
N C4 C5 O2 57.6(4) . . . . ?
C5 O2 C6 C7 60.2(4) . . . . ?
C1 N C7 C6 -130.8(3) . . . . ?
C4 N C7 C6 50.8(4) . . . . ?
O2 C6 C7 N -54.0(4) . . . . ?


_refine_diff_density_max         0.451
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.118

_shelxl_version_number           2014/6

_shelx_res_file                  
;
TITL PK254  P2(1)/c C7H8NO2I  OD APR14
REM P2(1)/c (#14 in standard setting)
CELL 0.71073   8.763815   8.590972  11.498876  90.0000 101.4875  90.0000
ZERR    4.00   0.000310   0.000324   0.000387   0.0000   0.0036   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2
SFAC C H N O I
UNIT 28.00 32.00 4.00 8.00 4.00
MORE 0
TEMP -93
SHEL 11. 0.80
L.S. 6
BOND
FMAP 2
PLAN -10
CONF
ACTA
EQIV $1 x, 0.5-y, -0.5+z
HTAB I O1_$1
WGHT    0.015800
FVAR       4.27311
MOLE   1
I     5    0.651286    0.197384    0.474710    11.00000    0.02297    0.01713 =
         0.02476   -0.00334    0.00556   -0.00036
O1    4    0.633064    0.570668    0.838367    11.00000    0.04880    0.02338 =
         0.02450    0.00412    0.01659   -0.00427
O2    4    0.942165    0.996921    0.737661    11.00000    0.02721    0.01798 =
         0.03908   -0.00305    0.01029   -0.00491
N     3    0.737731    0.740510    0.726643    11.00000    0.02003    0.01610 =
         0.01841   -0.00017    0.00461   -0.00004
C1    1    0.684401    0.600267    0.748249    11.00000    0.01658    0.01606 =
         0.02140   -0.00174   -0.00076    0.00295
C2    1    0.683799    0.481038    0.658550    11.00000    0.02162    0.01590 =
         0.02623    0.00112    0.00561   -0.00284
C3    1    0.671483    0.376499    0.589243    11.00000    0.02188    0.01955 =
         0.02792    0.00207    0.00355    0.00138
C4    1    0.726064    0.873515    0.804186    11.00000    0.02671    0.01559 =
         0.02237   -0.00390    0.00658    0.00049
AFIX  23
H4A   2    0.689407    0.838023    0.875821    11.00000   -1.20000
H4B   2    0.650060    0.949814    0.761980    11.00000   -1.20000
AFIX   0
C5    1    0.884372    0.949087    0.839719    11.00000    0.02916    0.02096 =
         0.02921   -0.00849    0.00435   -0.00115
AFIX  23
H5A   2    0.876541    1.040693    0.890436    11.00000   -1.20000
H5B   2    0.958108    0.874390    0.886479    11.00000   -1.20000
AFIX   0
C6    1    0.959827    0.864082    0.667190    11.00000    0.02773    0.01968 =
         0.03489   -0.00375    0.01254   -0.00201
AFIX  23
H6A   2    1.035709    0.791803    0.714545    11.00000   -1.20000
H6B   2    1.002534    0.897660    0.597741    11.00000   -1.20000
AFIX   0
C7    1    0.808524    0.779040    0.624318    11.00000    0.02625    0.02245 =
         0.01886    0.00040    0.00982    0.00117
AFIX  23
H7A   2    0.736631    0.845328    0.567838    11.00000   -1.20000
H7B   2    0.828021    0.682442    0.582646    11.00000   -1.20000

AFIX   0
HKLF 4

REM  PK254  P2(1)/c C7H8NO2I  OD APR14
REM R1 =  0.0241 for    1495 Fo > 4sig(Fo)  and  0.0318 for all    1725 data
REM    100 parameters refined using      0 restraints

END

WGHT      0.0159      0.0000

REM Highest difference peak  0.451,  deepest hole -0.490,  1-sigma level  0.118
Q1    1   0.8604  0.7481  0.4604  11.00000  0.05    0.45
Q2    1   0.7802  0.3000  0.7572  11.00000  0.05    0.44
Q3    1   0.7961  1.1049  0.6868  11.00000  0.05    0.42
Q4    1   0.9024  0.9294  0.5735  11.00000  0.05    0.41
Q5    1   0.8360  0.8548  0.5367  11.00000  0.05    0.40
Q6    1   0.5273  0.0322  0.3183  11.00000  0.05    0.39
Q7    1   1.0563  0.7238  0.7964  11.00000  0.05    0.39
Q8    1   0.3663  0.2816  0.4651  11.00000  0.05    0.38
Q9    1   0.6552  0.8771  0.9702  11.00000  0.05    0.37
Q10   1   0.9279  0.1419  0.5788  11.00000  0.05    0.37
;
_shelx_res_checksum              96141

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
####################################################################### 
# 
# 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_PK286_2
_database_code_depnum_ccdc_archive 'CCDC 1044488'
_audit_update_record             
;
2015-01-20 deposited with the CCDC.
2015-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        '3-Iodopropiolamide acetonitrile complex'
_chemical_name_common            ?
_chemical_melting_point          423
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H5 I N2 O'
_chemical_formula_weight         236.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.8120(4)
_cell_length_b                   8.1725(2)
_cell_length_c                   9.2790(3)
_cell_angle_alpha                90
_cell_angle_beta                 102.202(4)
_cell_angle_gamma                90
_cell_volume                     801.38(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.00(10)
_cell_measurement_reflns_used    2201
_cell_measurement_theta_min      3.3540
_cell_measurement_theta_max      28.8540


_exptl_crystal_description       'rectangular prism'
_exptl_crystal_colour            colourless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.956
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    3.924
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.81801
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.3385
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            3655
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.151
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1641
_reflns_number_gt                1409
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2000-2007)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0168P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1641
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0532
_refine_ls_wR_factor_gt          0.0484
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.23408(2) -0.23381(2) 0.31352(2) 0.03016(10) Uani 1 1 d . . . . .
O O 0.4235(2) 0.3297(2) 0.5695(2) 0.0272(5) Uani 1 1 d . . . . .
N1 N 0.4559(3) 0.3561(3) 0.3378(3) 0.0261(6) Uani 1 1 d . . . . .
C1 C 0.4163(3) 0.2764(3) 0.4423(3) 0.0214(7) Uani 1 1 d . . . . .
C2 C 0.3596(3) 0.1155(4) 0.4017(3) 0.0245(7) Uani 1 1 d . . . . .
C3 C 0.3128(3) -0.0158(4) 0.3731(3) 0.0272(7) Uani 1 1 d . . . . .
H1 H 0.487(3) 0.452(4) 0.354(4) 0.037(10) Uiso 1 1 d . . . . .
H2 H 0.449(3) 0.307(4) 0.257(4) 0.023(9) Uiso 1 1 d . . . . .
C4 C 0.1055(3) -0.6540(5) 0.1426(4) 0.0377(9) Uani 1 1 d . . . . .
C5 C 0.0961(4) -0.8067(5) 0.0601(5) 0.0483(10) Uani 1 1 d . . . . .
H5A H 0.0574 -0.7856 -0.0436 0.072 Uiso 1 1 calc R U . . .
H5B H 0.0438 -0.8845 0.1011 0.072 Uiso 1 1 calc R U . . .
H5C H 0.1809 -0.8528 0.0672 0.072 Uiso 1 1 calc R U . . .
N2 N 0.1112(3) -0.5379(4) 0.2075(4) 0.0612(10) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I1 0.02805(15) 0.02324(13) 0.03887(16) -0.00432(9) 0.00639(11) -0.00657(8)
O 0.0395(14) 0.0238(11) 0.0192(11) -0.0015(9) 0.0079(10) -0.0067(10)
N1 0.0373(17) 0.0238(15) 0.0184(15) -0.0061(13) 0.0083(13) -0.0076(13)
C1 0.0207(16) 0.0200(14) 0.0234(17) 0.0018(13) 0.0046(14) 0.0020(12)
C2 0.0281(18) 0.0263(16) 0.0199(16) 0.0008(13) 0.0066(14) -0.0027(14)
C3 0.0274(18) 0.0283(17) 0.0263(17) 0.0025(14) 0.0064(15) -0.0009(14)
C4 0.035(2) 0.039(2) 0.040(2) -0.0016(18) 0.0091(17) -0.0139(17)
C5 0.045(2) 0.045(2) 0.055(3) -0.012(2) 0.012(2) -0.0011(19)
N2 0.065(2) 0.044(2) 0.074(3) -0.0142(19) 0.014(2) -0.0257(18)

_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
I1 C3 2.001(3) . ?
O C1 1.245(4) . ?
N1 C1 1.313(4) . ?
C1 C2 1.466(4) . ?
C2 C3 1.192(4) . ?
C4 N2 1.119(5) . ?
C4 C5 1.457(5) . ?

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
O C1 N1 124.1(3) . . ?
O C1 C2 119.8(3) . . ?
N1 C1 C2 116.1(3) . . ?
C3 C2 C1 178.0(3) . . ?
C2 C3 I1 176.9(3) . . ?
N2 C4 C5 178.7(4) . . ?

_refine_diff_density_max         0.454
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.106

_shelxl_version_number           2014/6

_shelx_res_file                  
;
TITL PK286_2 C3H2NOIxCH3CN P2(1)/c OD Oct14
REM P2(1)/c (#14 in standard setting)
CELL 0.71073  10.812005   8.172459   9.279050  90.0000 102.2019  90.0000
ZERR    4.00   0.000378   0.000212   0.000349   0.0000   0.0037   0.0000
LATT  1
SYMM -x, y+1/2,-z+1/2
SFAC C H N O I
UNIT 20.00 20.00 8.00 4.00 4.00
MORE 0
TEMP -123
LIST 6
L.S. 4
BOND
FMAP 2
PLAN -10
SHEL 11. 0.80
ACTA
WGHT    0.016800
FVAR       4.10290
MOLE   1
I1    5    0.234083   -0.233807    0.313516    11.00000    0.02805    0.02324 =
         0.03887   -0.00432    0.00639   -0.00657
O     4    0.423505    0.329722    0.569455    11.00000    0.03954    0.02378 =
         0.01917   -0.00147    0.00788   -0.00666
N1    3    0.455920    0.356064    0.337826    11.00000    0.03725    0.02379 =
         0.01839   -0.00607    0.00826   -0.00765
C1    1    0.416267    0.276369    0.442289    11.00000    0.02066    0.02003 =
         0.02344    0.00181    0.00456    0.00197
C2    1    0.359558    0.115456    0.401749    11.00000    0.02812    0.02628 =
         0.01988    0.00079    0.00664   -0.00275
C3    1    0.312826   -0.015804    0.373056    11.00000    0.02744    0.02833 =
         0.02627    0.00249    0.00639   -0.00094
H1    2    0.486968    0.452441    0.354000    11.00000    0.03711
H2    2    0.448514    0.306859    0.257413    11.00000    0.02315

MOLE 2
C4    1    0.105535   -0.654005    0.142619    11.00000    0.03514    0.03851 =
         0.03993   -0.00163    0.00909   -0.01392
C5    1    0.096108   -0.806729    0.060071    11.00000    0.04540    0.04511 =
         0.05484   -0.01229    0.01179   -0.00108
AFIX 137
H5A   2    0.057358   -0.785632   -0.043608    11.00000   -1.50000
H5B   2    0.043758   -0.884496    0.101108    11.00000   -1.50000
H5C   2    0.180867   -0.852804    0.067178    11.00000   -1.50000
AFIX   0
N2    3    0.111218   -0.537874    0.207505    11.00000    0.06519    0.04396 =
         0.07434   -0.01420    0.01436   -0.02566

MOLE   2
HKLF 4

REM  PK286_2 C3H2NOIxCH3CN P2(1)/c OD Oct14
REM R1 =  0.0242 for    1409 Fo > 4sig(Fo)  and  0.0314 for all    1641 data
REM     91 parameters refined using      0 restraints

END

WGHT      0.0157      0.0000

REM Highest difference peak  0.454,  deepest hole -0.634,  1-sigma level  0.106
Q1    1   0.1276 -0.2310  0.2504  11.00000  0.05    0.45
Q2    1   0.2153  0.2824  0.3011  11.00000  0.05    0.35
Q3    1   0.3773 -0.2736  0.1504  11.00000  0.05    0.35
Q4    1   0.5663  0.1820  0.3968  11.00000  0.05    0.33
Q5    1   0.2703  0.1814  0.5019  11.00000  0.05    0.33
Q6    1   0.4945  0.0289  0.3531  11.00000  0.05    0.32
Q7    1   0.1596 -0.3086  0.2215  11.00000  0.05    0.32
Q8    1   0.1768 -0.2218  0.3942  11.00000  0.05    0.32
Q9    1   0.3099  0.0983  0.4124  11.00000  0.05    0.32
Q10   1   0.0557 -0.2979  0.2940  11.00000  0.05    0.31
;
_shelx_res_checksum              78256

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1044497'
_audit_update_record             
;
2015-01-20 deposited with the CCDC.
2015-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        3-Iodo-N-methyl-propiolamide
_chemical_name_common            ?
_chemical_melting_point          449
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H4 I N O'
_chemical_formula_weight         208.98

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 2(1)'

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

_cell_length_a                   16.1674(10)
_cell_length_b                   4.1334(3)
_cell_length_c                   9.0094(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     602.07(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    180.1(2)
_cell_measurement_reflns_used    1349
_cell_measurement_theta_min      4.5280
_cell_measurement_theta_max      29.4840

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    5.202
_exptl_absorpt_correction_T_min  0.87902
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      180.1(2)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.3385
_diffrn_reflns_number            1756
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0368
_diffrn_measurement_method       'ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.39
_diffrn_reflns_theta_max         26.37
_reflns_number_total             992
_reflns_number_gt                935
_reflns_threshold_expression     >2sigma(I)
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.998

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0255P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 309 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         992
_refine_ls_number_parameters     65
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0253
_refine_ls_R_factor_gt           0.0232
_refine_ls_wR_factor_ref         0.0547
_refine_ls_wR_factor_gt          0.0528
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I I 1.02366(2) -0.10952(9) 0.41015(10) 0.02398(17) Uani 1 1 d . . . . .
O O 0.8200(3) 0.3471(14) 0.0105(6) 0.0284(13) Uani 1 1 d . . . . .
N N 0.7369(4) 0.4460(16) 0.2085(8) 0.0235(16) Uani 1 1 d . . . . .
H0 H 0.7304 0.4290 0.3052 0.054 Uiso 1 1 calc R U . . .
C1 C 0.8054(5) 0.3306(19) 0.1463(9) 0.0218(18) Uani 1 1 d . . . . .
C2 C 0.8657(4) 0.1900(19) 0.2454(8) 0.0229(16) Uani 1 1 d . . . . .
C3 C 0.9238(5) 0.0701(18) 0.3100(9) 0.0221(16) Uani 1 1 d . . . . .
C4 C 0.6727(5) 0.5987(19) 0.1212(10) 0.032(2) Uani 1 1 d . . . . .
H4A H 0.6964 0.7796 0.0651 0.048 Uiso 1 1 calc R U . . .
H4B H 0.6292 0.6795 0.1872 0.048 Uiso 1 1 calc R U . . .
H4C H 0.6492 0.4406 0.0521 0.048 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I 0.0211(2) 0.0269(2) 0.0240(3) 0.0070(4) -0.0041(4) 0.00205(14)
O 0.024(3) 0.051(3) 0.011(3) -0.001(3) 0.002(2) 0.008(3)
N 0.020(4) 0.034(3) 0.016(4) 0.001(3) 0.003(3) 0.007(3)
C1 0.017(4) 0.026(4) 0.022(5) 0.001(4) -0.001(4) 0.000(3)
C2 0.022(4) 0.029(4) 0.018(4) 0.001(4) 0.003(3) 0.004(3)
C3 0.022(4) 0.028(4) 0.016(4) 0.003(3) -0.001(3) 0.000(3)
C4 0.030(5) 0.041(5) 0.025(4) -0.002(4) -0.003(4) 0.012(4)

_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
I C3 1.993(8) . ?
O C1 1.248(9) . ?
N C1 1.330(11) . ?
N C4 1.446(10) . ?
C1 C2 1.445(11) . ?
C2 C3 1.211(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N C4 121.6(7) . . ?
O C1 N 123.5(8) . . ?
O C1 C2 120.0(7) . . ?
N C1 C2 116.5(7) . . ?
C3 C2 C1 170.2(8) . . ?
C2 C3 I 176.7(7) . . ?

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
C4 N C1 O 0.7(12) . . . . ?
C4 N C1 C2 178.7(7) . . . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.817
_refine_diff_density_rms         0.132

_shelxl_version_number           2014/6

_shelx_res_file                  
;
TITL PK281 C4H4NOI Pca2(1) OD SEPT14
REM Pca2(1) (#29, found as Pc2(1)b in cab setting)
CELL 0.71073  16.167416   4.133417   9.009375  90.0000  90.0000  90.0000
ZERR    4.00   0.001000   0.000265   0.000617   0.0000   0.0000   0.0000
LATT -1
SYMM -x,-y, z+1/2
SYMM  x+1/2,-y, z
SYMM -x+1/2, y, z+1/2
SFAC C H N O I
UNIT 16 16 4 4 4
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
MORE 0
SHEL 11. 0.80
L.S. 4
BOND
FMAP 2
PLAN -10
TEMP -93
CONF
ACTA
REM H.N   2    0.728555    0.459250    0.323041    11.00000    0.07750

WGHT    0.025500
FVAR       5.16539
I     5    1.023664   -0.109521    0.410151    11.00000    0.02106    0.02691 =
         0.02395    0.00696   -0.00405    0.00205
O     4    0.820020    0.347110    0.010464    11.00000    0.02401    0.05073 =
         0.01060   -0.00110    0.00194    0.00803
N     3    0.736864    0.446000    0.208493    11.00000    0.02044    0.03430 =
         0.01564    0.00067    0.00289    0.00694
AFIX  43
H0    2    0.730384    0.429027    0.305162    11.00000   -2.30000
AFIX   0
C1    1    0.805361    0.330600    0.146275    11.00000    0.01692    0.02642 =
         0.02212    0.00100   -0.00146   -0.00035
C2    1    0.865687    0.189954    0.245409    11.00000    0.02184    0.02919 =
         0.01765    0.00090    0.00294    0.00392
C3    1    0.923779    0.070057    0.310012    11.00000    0.02207    0.02806 =
         0.01627    0.00269   -0.00148    0.00040
C4    1    0.672742    0.598748    0.121174    11.00000    0.03022    0.04105 =
         0.02501   -0.00237   -0.00313    0.01153
AFIX 137
H4A   2    0.696417    0.779597    0.065113    11.00000   -1.50000
H4B   2    0.629214    0.679528    0.187184    11.00000   -1.50000
H4C   2    0.649151    0.440608    0.052065    11.00000   -1.50000

MOLE   2
AFIX   0
HKLF 4

REM  PK281 C4H4NOI Pca2(1) OD SEPT14
REM R1 =  0.0232 for     935 Fo > 4sig(Fo)  and  0.0253 for all     992 data
REM     65 parameters refined using      1 restraints

END

WGHT      0.0253      0.0000

REM Highest difference peak  0.471,  deepest hole -0.817,  1-sigma level  0.132
Q1    1   0.5549  0.4769  0.1462  11.00000  0.05    0.47
Q2    1   1.1202  0.0118  0.4136  11.00000  0.05    0.43
Q3    1   0.9465  0.4856  0.1738  11.00000  0.05    0.42
Q4    1   0.9372  0.3853  0.2160  11.00000  0.05    0.42
Q5    1   0.8933  0.5057  0.1248  11.00000  0.05    0.41
Q6    1   0.8136 -0.0074  0.4059  11.00000  0.05    0.39
Q7    1   0.8756  0.4011  0.4138  11.00000  0.05    0.35
Q8    1   0.6020  0.5222  0.1989  11.00000  0.05    0.35
Q9    1   1.1628  0.1677  0.3831  11.00000  0.05    0.33
Q10   1   1.0202 -0.1399  0.5840  11.00000  0.05    0.33
;
_shelx_res_checksum              12061

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: diethyl ether'
