# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1571889'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H10 N O2, Cl'
_chemical_formula_sum            'C4 H10 Cl N O2'
_chemical_formula_weight         139.58

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_H-M_alt        'P 21/m'
_space_group_name_Hall           '-P 2yb'

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

_cell_length_a                   5.9059(3)
_cell_length_b                   6.3964(3)
_cell_length_c                   8.9893(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.064(2)
_cell_angle_gamma                90
_cell_volume                     334.36(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7632
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      33.07

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             148
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.323
_exptl_crystal_size_mid          0.227
_exptl_crystal_size_min          0.204
_exptl_absorpt_coefficient_mu    0.487
_shelx_estimated_absorpt_T_min   0.858
_shelx_estimated_absorpt_T_max   0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7907
_exptl_absorpt_correction_T_max  0.8499
_exptl_absorpt_process_details   'SADABS (Bruker, 2015)'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16556
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.301
_diffrn_reflns_theta_max         33.303
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             1386
_reflns_number_gt                1235
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_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)+(0.0522P)²+0.1748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1386
_refine_ls_number_parameters     71
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0781
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   0.831
_refine_ls_restrained_S_all      0.831
_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
Cl1 Cl 0.71198(5) 0.7500 0.06328(4) 0.01834(10) Uani 1 2 d S T P . .
O2 O 0.61552(17) 0.7500 0.48426(12) 0.0232(2) Uani 1 2 d S T P . .
O1 O 0.35164(18) 0.7500 0.27333(12) 0.0265(2) Uani 1 2 d S T P . .
N1 N 0.1636(2) 0.7500 0.92122(13) 0.0179(2) Uani 1 2 d S T P . .
C1 C 0.4163(2) 0.7500 0.42342(14) 0.0164(2) Uani 1 2 d S T P . .
C4 C 0.0815(2) 0.7500 0.75544(15) 0.0206(2) Uani 1 2 d S T P . .
C3 C 0.2840(2) 0.7500 0.67362(16) 0.0206(2) Uani 1 2 d S T P . .
C2 C 0.2144(2) 0.7500 0.50405(15) 0.0212(3) Uani 1 2 d S T P . .
H1 H 0.467(4) 0.7500 0.228(3) 0.041(6) Uiso 1 2 d S . P . .
H4 H -0.010(3) 0.874(3) 0.7316(16) 0.038(4) Uiso 1 1 d . . . . .
H3 H 0.378(3) 0.870(3) 0.705(2) 0.050(5) Uiso 1 1 d . . . . .
H2 H 0.120(3) 0.865(3) 0.4692(18) 0.043(4) Uiso 1 1 d . . . . .
H1A H 0.051(3) 0.7500 0.972(2) 0.025(5) Uiso 1 2 d S . P . .
H1B H 0.249(3) 0.860(3) 0.9500(17) 0.040(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.2077(16) . ?
O1 C1 1.3364(16) . ?
O1 H1 0.85(3) . ?
N1 C4 1.4844(17) . ?
N1 H1A 0.87(2) . ?
N1 H1B 0.879(16) . ?
C1 C2 1.5000(19) . ?
C4 C3 1.5093(18) . ?
C4 H4 0.965(16) . ?
C3 C2 1.5079(19) . ?
C3 H3 0.962(18) . ?
C2 H2 0.943(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 111.6(16) . . ?
C4 N1 H1A 112.4(14) . . ?
C4 N1 H1B 111.4(10) . . ?
H1A N1 H1B 107.2(12) . . ?
O2 C1 O1 122.76(12) . . ?
O2 C1 C2 125.11(12) . . ?
O1 C1 C2 112.13(11) . . ?
N1 C4 C3 109.97(11) . . ?
N1 C4 H4 107.2(9) . . ?
C3 C4 H4 110.7(9) . . ?
C4 C3 C2 113.16(12) . . ?
C4 C3 H3 108.6(10) . . ?
C2 C3 H3 110.0(11) . . ?
C1 C2 C3 112.90(11) . . ?
C1 C2 H2 108.1(10) . . ?
C3 C2 H2 112.1(10) . . ?

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
N1 C4 C3 C2 180.000(0) . . . . ?
O2 C1 C2 C3 0.000(0) . . . . ?
O1 C1 C2 C3 180.000(0) . . . . ?
C4 C3 C2 C1 180.000(0) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 Cl1 0.85(3) 2.25(3) 3.0820(11) 167(2) .
N1 H1A Cl1 0.87(2) 2.29(2) 3.1521(12) 169.5(18) 1_456
N1 H1B Cl1 0.879(16) 2.837(15) 3.2671(12) 111.8(12) 1_556
N1 H1B Cl1 0.879(16) 2.508(16) 3.2790(3) 146.9(13) 3_676

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.094

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1571896'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N O2, Cl O4'
_chemical_formula_sum            'C6 H14 Cl N O6'
_chemical_formula_weight         231.63

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.2863(3)
_cell_length_b                   5.6138(3)
_cell_length_c                   17.4559(9)
_cell_angle_alpha                82.962(2)
_cell_angle_beta                 86.746(2)
_cell_angle_gamma                88.924(2)
_cell_volume                     513.26(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.360
_exptl_absorpt_coefficient_mu    0.378
_shelx_estimated_absorpt_T_min   0.833
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7267
_exptl_absorpt_correction_T_max  0.8014
_exptl_absorpt_process_details   'SADABS (Bruker, 2015)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13688
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.355
_diffrn_reflns_theta_max         27.264
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2284
_reflns_number_gt                2074
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0312P)²+0.2789P]
 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     SHELXL
_refine_ls_extinction_coef       0.094(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2284
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0286
_refine_ls_wR_factor_ref         0.0726
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.010
_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
Cl1 Cl 0.84426(6) 0.28921(5) 0.89777(2) 0.01838(12) Uani 1 1 d . . . . .
C1 C -0.2470(3) 0.5444(3) 0.57159(8) 0.0212(3) Uani 1 1 d . . . . .
N1 N 0.3131(3) 0.7932(2) 0.89739(7) 0.0208(3) Uani 1 1 d . . . . .
O2 O -0.2846(2) 0.6916(2) 0.51622(6) 0.0318(3) Uani 1 1 d . . . . .
O1 O -0.3701(2) 0.3410(2) 0.58628(7) 0.0302(3) Uani 1 1 d . . . . .
C2 C -0.0565(3) 0.5753(3) 0.63002(8) 0.0223(3) Uani 1 1 d . . . . .
O3 O 0.7534(2) 0.4750(2) 0.94214(7) 0.0338(3) Uani 1 1 d . . . . .
C3 C 0.0538(3) 0.8250(3) 0.62198(9) 0.0282(3) Uani 1 1 d . . . . .
O4 O 1.1175(2) 0.29665(19) 0.89075(7) 0.0305(3) Uani 1 1 d . . . . .
C4 C 0.2612(3) 0.8473(3) 0.67796(9) 0.0285(3) Uani 1 1 d . . . . .
O6 O 0.7445(2) 0.3239(2) 0.82263(6) 0.0312(3) Uani 1 1 d . . . . .
C6 C 0.3877(3) 0.8394(3) 0.81337(8) 0.0235(3) Uani 1 1 d . . . . .
O5 O 0.7721(2) 0.05756(19) 0.93707(7) 0.0317(3) Uani 1 1 d . . . . .
C5 C 0.1703(3) 0.8197(3) 0.76258(8) 0.0213(3) Uani 1 1 d . . . . .
H1A H 0.444(4) 0.808(4) 0.9261(12) 0.042(5) Uiso 1 1 d . . . . .
H1B H 0.255(4) 0.656(4) 0.9081(12) 0.047(6) Uiso 1 1 d . . . . .
H1C H 0.208(5) 0.888(4) 0.9105(13) 0.053(7) Uiso 1 1 d . . . . .
H2A H -0.130(3) 0.527(3) 0.6798(10) 0.025(4) Uiso 1 1 d . . . . .
H5A H 0.088(4) 0.670(4) 0.7769(11) 0.035(5) Uiso 1 1 d . . . . .
H3B H -0.076(4) 0.943(3) 0.6298(11) 0.033(5) Uiso 1 1 d . . . . .
H6A H 0.510(4) 0.726(4) 0.8037(11) 0.040(5) Uiso 1 1 d . . . . .
H6B H 0.458(4) 0.993(4) 0.8045(12) 0.042(5) Uiso 1 1 d . . . . .
H4B H 0.352(4) 0.993(4) 0.6649(12) 0.045(6) Uiso 1 1 d . . . . .
H4A H 0.395(4) 0.734(4) 0.6706(12) 0.045(6) Uiso 1 1 d . . . . .
H5B H 0.041(4) 0.934(4) 0.7718(12) 0.047(6) Uiso 1 1 d . . . . .
H2B H 0.070(4) 0.457(3) 0.6237(11) 0.033(5) Uiso 1 1 d . . . . .
H3A H 0.123(4) 0.867(4) 0.5712(12) 0.041(5) Uiso 1 1 d . . . . .
H1 H -0.463(4) 0.334(4) 0.5560(13) 0.045(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 O6 1.4314(11) . ?
Cl1 O3 1.4336(11) . ?
Cl1 O5 1.4413(11) . ?
Cl1 O4 1.4434(11) . ?
C1 O2 1.2154(18) . ?
C1 O1 1.3152(18) . ?
C1 C2 1.500(2) . ?
N1 C6 1.4896(19) . ?
N1 H1A 0.89(2) . ?
N1 H1B 0.83(2) . ?
N1 H1C 0.81(2) . ?
O1 H1 0.75(2) . ?
C2 C3 1.516(2) . ?
C2 H2A 0.941(18) . ?
C2 H2B 0.947(19) . ?
C3 C4 1.526(2) . ?
C3 H3B 0.962(19) . ?
C3 H3A 0.94(2) . ?
C4 C5 1.518(2) . ?
C4 H4B 0.95(2) . ?
C4 H4A 0.96(2) . ?
C6 C5 1.505(2) . ?
C6 H6A 0.92(2) . ?
C6 H6B 0.94(2) . ?
C5 H5A 0.95(2) . ?
C5 H5B 0.95(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O6 Cl1 O3 110.19(7) . . ?
O6 Cl1 O5 110.05(7) . . ?
O3 Cl1 O5 110.07(7) . . ?
O6 Cl1 O4 109.84(7) . . ?
O3 Cl1 O4 108.65(7) . . ?
O5 Cl1 O4 107.99(7) . . ?
O2 C1 O1 123.14(13) . . ?
O2 C1 C2 123.71(13) . . ?
O1 C1 C2 113.14(12) . . ?
C6 N1 H1A 111.3(14) . . ?
C6 N1 H1B 110.3(15) . . ?
H1A N1 H1B 109.2(19) . . ?
C6 N1 H1C 112.2(16) . . ?
H1A N1 H1C 105(2) . . ?
H1B N1 H1C 108(2) . . ?
C1 O1 H1 109.3(17) . . ?
C1 C2 C3 113.66(12) . . ?
C1 C2 H2A 108.8(11) . . ?
C3 C2 H2A 112.8(10) . . ?
C1 C2 H2B 105.7(11) . . ?
C3 C2 H2B 111.7(11) . . ?
H2A C2 H2B 103.5(15) . . ?
C2 C3 C4 112.80(13) . . ?
C2 C3 H3B 111.0(11) . . ?
C4 C3 H3B 108.8(11) . . ?
C2 C3 H3A 110.1(12) . . ?
C4 C3 H3A 108.3(12) . . ?
H3B C3 H3A 105.6(16) . . ?
C5 C4 C3 114.55(13) . . ?
C5 C4 H4B 110.4(13) . . ?
C3 C4 H4B 111.3(13) . . ?
C5 C4 H4A 109.2(13) . . ?
C3 C4 H4A 110.5(13) . . ?
H4B C4 H4A 99.9(18) . . ?
N1 C6 C5 113.10(12) . . ?
N1 C6 H6A 106.3(12) . . ?
C5 C6 H6A 109.4(12) . . ?
N1 C6 H6B 107.0(13) . . ?
C5 C6 H6B 110.9(12) . . ?
H6A C6 H6B 109.9(18) . . ?
C6 C5 C4 110.80(12) . . ?
C6 C5 H5A 109.8(11) . . ?
C4 C5 H5A 111.0(12) . . ?
C6 C5 H5B 111.0(13) . . ?
C4 C5 H5B 110.9(13) . . ?
H5A C5 H5B 103.2(17) . . ?

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
O2 C1 C2 C3 10.0(2) . . . . ?
O1 C1 C2 C3 -169.98(13) . . . . ?
C1 C2 C3 C4 -175.71(13) . . . . ?
C2 C3 C4 C5 -66.1(2) . . . . ?
N1 C6 C5 C4 -175.19(13) . . . . ?
C3 C4 C5 C6 178.89(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.75(2) 1.91(2) 2.6515(16) 176(2) 2_466
N1 H1A O3 0.89(2) 2.46(2) 2.9878(17) 118.3(16) .
N1 H1A O5 0.89(2) 2.28(2) 3.0245(17) 141.4(18) 1_565
N1 H1B O3 0.83(2) 2.63(2) 3.0186(18) 110.5(17) 2_667
N1 H1B O4 0.83(2) 2.22(2) 3.0091(17) 159(2) 1_455
N1 H1C Cl1 0.81(2) 2.93(3) 3.6933(14) 159(2) 1_465
N1 H1C O4 0.81(2) 2.32(2) 2.9823(17) 140(2) 1_465
N1 H1C O5 0.81(2) 2.52(3) 3.2754(18) 157(2) 1_465
C6 H6A O6 0.92(2) 2.55(2) 3.416(2) 156.9(17) .
C6 H6B O6 0.94(2) 2.48(2) 3.3641(19) 157.3(17) 1_565
O1 H1 O2 0.75(2) 1.91(2) 2.6515(16) 176(2) 2_466
N1 H1A O3 0.89(2) 2.46(2) 2.9878(17) 118.3(16) .
N1 H1A O5 0.89(2) 2.28(2) 3.0245(17) 141.4(18) 1_565
N1 H1B O3 0.83(2) 2.63(2) 3.0186(18) 110.5(17) 2_667
N1 H1B O4 0.83(2) 2.22(2) 3.0091(17) 159(2) 1_455
N1 H1C Cl1 0.81(2) 2.93(3) 3.6933(14) 159(2) 1_465
N1 H1C O4 0.81(2) 2.32(2) 2.9823(17) 140(2) 1_465
N1 H1C O5 0.81(2) 2.52(3) 3.2754(18) 157(2) 1_465
C6 H6A O6 0.92(2) 2.55(2) 3.416(2) 156.9(17) .
C6 H6B O6 0.94(2) 2.48(2) 3.3641(19) 157.3(17) 1_565

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1571895'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N O2, N O3'
_chemical_formula_sum            'C6 H14 N2 O5'
_chemical_formula_weight         194.19

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   4.8399(5)
_cell_length_b                   8.3511(7)
_cell_length_c                   23.167(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.273(4)
_cell_angle_gamma                90
_cell_volume                     936.14(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    823
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      18.90

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.124
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_max          0.20
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8056
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_process_details   'SADABS (Bruker, 2015)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24903
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_av_R_equivalents  0.0813
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.593
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2150
_reflns_number_gt                1282
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.2000P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.02(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2150
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2061
_refine_ls_R_factor_gt           0.1438
_refine_ls_wR_factor_ref         0.4744
_refine_ls_wR_factor_gt          0.4324
_refine_ls_goodness_of_fit_ref   1.804
_refine_ls_restrained_S_all      1.804
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.8982(10) 0.1938(5) 0.5089(2) 0.0540(13) Uani 1 1 d . . . . .
N2A N 0.136(3) 1.2247(12) 0.2926(4) 0.0538(14) Uani 0.590(5) 1 d . . P A 1
N2B N 0.035(4) 1.2062(17) 0.3041(6) 0.0538(14) Uani 0.410(5) 1 d . . P A 2
O2 O 0.7347(10) 0.0089(5) 0.44932(19) 0.0677(13) Uani 1 1 d . . . . .
O5 O 0.0355(11) 1.1225(6) 0.34182(19) 0.0752(17) Uani 1 1 d . . . . .
O4A O 0.340(2) 1.2275(8) 0.2829(3) 0.0677(13) Uani 0.590(5) 1 d . . P A 1
O4B O 0.147(3) 1.1251(12) 0.2586(5) 0.0677(13) Uani 0.410(5) 1 d . . P A 2
O3A O 0.0272(19) 1.3465(9) 0.2820(3) 0.0677(13) Uani 0.590(5) 1 d . . P A 1
O3B O -0.193(3) 1.2774(13) 0.2846(5) 0.0677(13) Uani 0.410(5) 1 d . . P A 2
C1 C 0.7328(10) 0.1488(5) 0.4689(2) 0.0386(14) Uani 1 1 d . . . . .
N1 N 0.5767(12) 0.9258(5) 0.31272(18) 0.0538(14) Uani 1 1 d . . . . .
C4 C 0.4792(11) 0.5361(6) 0.3949(3) 0.0413(15) Uani 1 1 d . . . . .
C5 C 0.6307(12) 0.6735(6) 0.3669(2) 0.0451(15) Uani 1 1 d . . . . .
C2 C 0.5374(13) 0.2667(6) 0.4446(3) 0.0434(15) Uani 1 1 d . . . . .
C6 C 0.4326(13) 0.8010(7) 0.3444(2) 0.0467(15) Uani 1 1 d . . . . .
C3 C 0.6799(11) 0.4161(6) 0.4212(3) 0.0458(15) Uani 1 1 d . . . . .
H4B H 0.348(10) 0.476(6) 0.3622(19) 0.026(11) Uiso 1 1 d . . . . .
H3A H 0.785(12) 0.470(7) 0.453(2) 0.046(15) Uiso 1 1 d . . . . .
H5A H 0.735(13) 0.621(8) 0.332(3) 0.062(17) Uiso 1 1 d . . . . .
H6B H 0.261(13) 0.756(7) 0.314(3) 0.060(18) Uiso 1 1 d . . . . .
H2A H 0.398(10) 0.236(5) 0.420(2) 0.020(11) Uiso 1 1 d . . . . .
H2B H 0.420(12) 0.266(6) 0.468(2) 0.031(16) Uiso 1 1 d . . . . .
H6A H 0.344(10) 0.851(6) 0.375(2) 0.025(11) Uiso 1 1 d . . . . .
H5B H 0.803(10) 0.725(6) 0.3968(19) 0.032(12) Uiso 1 1 d . . . . .
H4A H 0.355(16) 0.571(9) 0.419(3) 0.08(2) Uiso 1 1 d . . . . .
H3B H 0.870(13) 0.385(8) 0.396(3) 0.060(17) Uiso 1 1 d . . . . .
H1 H 1.022(15) 0.139(9) 0.521(3) 0.05(2) Uiso 1 1 d . . . . .
H1A H 0.4869 0.9867 0.3000 0.050 Uiso 1 1 d . U . . .
H1B H 0.7084 0.9652 0.3299 0.050 Uiso 1 1 d . U . . .
H1C H 0.6781 0.8873 0.2823 0.050 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.269(7) . ?
O1 H1 0.80(7) . ?
N2A O4A 1.014(13) . ?
N2A O3A 1.170(12) . ?
N2A O5 1.514(11) . ?
N2B O5 1.119(15) . ?
N2B O3B 1.323(19) . ?
N2B O4B 1.375(17) . ?
O2 C1 1.253(6) . ?
O4A O3A 1.809(12) . ?
C1 C2 1.468(8) . ?
N1 C6 1.461(7) . ?
N1 H1A 0.727(5) . ?
N1 H1B 0.814(5) . ?
N1 H1C 0.925(5) . ?
C4 C3 1.514(8) . ?
C4 C5 1.515(8) . ?
C4 H4B 1.10(5) . ?
C4 H4A 0.87(7) . ?
C5 C6 1.518(8) . ?
C5 H5A 1.06(7) . ?
C5 H5B 1.15(5) . ?
C2 C3 1.530(8) . ?
C2 H2A 0.91(5) . ?
C2 H2B 0.79(6) . ?
C6 H6B 1.14(6) . ?
C6 H6A 0.94(5) . ?
C3 H3A 0.99(6) . ?
C3 H3B 1.13(6) . ?

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 O1 H1 123(5) . . ?
O4A N2A O3A 111.7(11) . . ?
O4A N2A O5 120.7(11) . . ?
O3A N2A O5 119.8(10) . . ?
O5 N2B O3B 122.3(14) . . ?
O5 N2B O4B 107.2(12) . . ?
O3B N2B O4B 107.5(13) . . ?
N2A O4A O3A 36.9(7) . . ?
N2A O3A O4A 31.4(7) . . ?
O2 C1 O1 122.0(5) . . ?
O2 C1 C2 119.8(5) . . ?
O1 C1 C2 118.2(4) . . ?
C6 N1 H1A 114.5(6) . . ?
C6 N1 H1B 114.8(5) . . ?
H1A N1 H1B 111.7(5) . . ?
C6 N1 H1C 113.7(4) . . ?
H1A N1 H1C 104.9(5) . . ?
H1B N1 H1C 95.2(5) . . ?
C3 C4 C5 111.2(5) . . ?
C3 C4 H4B 109(2) . . ?
C5 C4 H4B 109(2) . . ?
C3 C4 H4A 114(5) . . ?
C5 C4 H4A 111(5) . . ?
H4B C4 H4A 101(6) . . ?
C4 C5 C6 111.8(5) . . ?
C4 C5 H5A 105(4) . . ?
C6 C5 H5A 110(3) . . ?
C4 C5 H5B 112(2) . . ?
C6 C5 H5B 113(2) . . ?
H5A C5 H5B 105(4) . . ?
C1 C2 C3 113.0(5) . . ?
C1 C2 H2A 121(3) . . ?
C3 C2 H2A 110(3) . . ?
C1 C2 H2B 102(4) . . ?
C3 C2 H2B 126(4) . . ?
H2A C2 H2B 83(4) . . ?
N1 C6 C5 111.6(5) . . ?
N1 C6 H6B 106(3) . . ?
C5 C6 H6B 115(3) . . ?
N1 C6 H6A 107(3) . . ?
C5 C6 H6A 110(3) . . ?
H6B C6 H6A 106(4) . . ?
C4 C3 C2 113.1(5) . . ?
C4 C3 H3A 108(3) . . ?
C2 C3 H3A 110(3) . . ?
C4 C3 H3B 118(3) . . ?
C2 C3 H3B 112(3) . . ?
H3A C3 H3B 94(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
O3B N2B O5 N2A -176(4) . . . . ?
O4B N2B O5 N2A 59(3) . . . . ?
O4A N2A O5 N2B -178(4) . . . . ?
O3A N2A O5 N2B 35(3) . . . . ?
O5 N2A O4A O3A -149.0(16) . . . . ?
O5 N2A O3A O4A 149.3(18) . . . . ?
C3 C4 C5 C6 -175.7(5) . . . . ?
O2 C1 C2 C3 -122.7(6) . . . . ?
O1 C1 C2 C3 56.4(7) . . . . ?
C4 C5 C6 N1 -174.6(4) . . . . ?
C5 C4 C3 C2 -174.2(5) . . . . ?
C1 C2 C3 C4 178.6(5) . . . . ?

_refine_diff_density_max         1.212
_refine_diff_density_min         -0.834
_refine_diff_density_rms         0.113

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1571894'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H14 N O2), 2(I), H2 O'
_chemical_formula_sum            'C12 H30 I2 N2 O5'
_chemical_formula_weight         536.18

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                   30.237(2)
_cell_length_b                   5.0915(3)
_cell_length_c                   12.8358(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.163(2)
_cell_angle_gamma                90
_cell_volume                     1973.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9830
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      27.30

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.134
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_max          0.366
_exptl_absorpt_coefficient_mu    3.207
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2389
_exptl_absorpt_correction_T_max  0.3330
_exptl_absorpt_process_details   'SADABS (Bruker, 2015)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24581
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.699
_diffrn_reflns_theta_max         27.301
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2222
_reflns_number_gt                2003
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0134P)²+1.7484P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00148(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2222
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0165
_refine_ls_R_factor_gt           0.0132
_refine_ls_wR_factor_ref         0.0324
_refine_ls_wR_factor_gt          0.0312
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.005
_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
H1B H 0.5404(7) 0.249(5) 0.0831(17) 0.039(6) Uiso 1 1 d . . . . .
H1C H 0.5545(7) 0.510(5) 0.0633(18) 0.037(6) Uiso 1 1 d . . . . .
H1A H 0.5391(7) 0.446(4) 0.1647(17) 0.033(5) Uiso 1 1 d . . . . .
H6B H 0.6142(6) 0.243(4) 0.0896(14) 0.018(4) Uiso 1 1 d . . . . .
H6A H 0.5968(6) 0.163(3) 0.1968(16) 0.019(5) Uiso 1 1 d . . . . .
H2B H 0.6533(7) 0.838(3) 0.3892(15) 0.020(5) Uiso 1 1 d . . . . .
H5A H 0.6062(6) 0.602(3) 0.2552(14) 0.017(4) Uiso 1 1 d . . . . .
H5B H 0.6293(6) 0.664(4) 0.1561(16) 0.024(5) Uiso 1 1 d . . . . .
H2A H 0.6787(7) 0.630(3) 0.4503(16) 0.024(5) Uiso 1 1 d . . . . .
H4B H 0.6847(6) 0.343(3) 0.1980(16) 0.023(5) Uiso 1 1 d . . . . .
H3A H 0.7286(7) 0.573(4) 0.3149(15) 0.026(5) Uiso 1 1 d . . . . .
H4A H 0.6649(6) 0.302(4) 0.3031(16) 0.026(5) Uiso 1 1 d . . . . .
H3B H 0.7033(7) 0.784(5) 0.2493(17) 0.035(6) Uiso 1 1 d . . . . .
I1 I 0.44113(2) 0.12973(2) 0.08401(2) 0.02087(5) Uani 1 1 d . . . . .
O1 O 0.69625(4) 1.0893(2) 0.52711(10) 0.0255(3) Uani 1 1 d . . . . .
O2 O 0.74765(4) 1.0255(2) 0.41170(9) 0.0251(3) Uani 1 1 d . . . . .
C1 C 0.71192(5) 0.9708(3) 0.44566(12) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.68171(5) 0.7633(3) 0.39836(12) 0.0179(3) Uani 1 1 d . . . . .
C3 C 0.69887(5) 0.6476(3) 0.29920(13) 0.0205(3) Uani 1 1 d . . . . .
C4 C 0.66917(5) 0.4321(3) 0.25076(14) 0.0204(3) Uani 1 1 d . . . . .
C5 C 0.62480(5) 0.5284(3) 0.20316(13) 0.0188(3) Uani 1 1 d . . . . .
C6 C 0.60020(5) 0.3031(3) 0.14938(13) 0.0193(3) Uani 1 1 d . . . . .
N1 N 0.55443(5) 0.3814(3) 0.11190(12) 0.0217(3) Uani 1 1 d . . . . .
O3 O 0.5000 0.6761(4) 0.2500 0.0274(4) Uani 1 2 d S T P . .
H1 H 0.7111(8) 1.184(4) 0.5432(18) 0.033 Uiso 1 1 d . U . . .
H3C H 0.5138(7) 0.773(5) 0.2879(16) 0.033 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3176(19) . ?
O1 H1 0.68(2) . ?
O2 C1 1.2194(19) . ?
C1 C2 1.503(2) . ?
C2 C3 1.520(2) . ?
C2 H2B 0.94(2) . ?
C2 H2A 0.96(2) . ?
C3 C4 1.528(2) . ?
C3 H3A 0.99(2) . ?
C3 H3B 0.96(2) . ?
C4 C5 1.524(2) . ?
C4 H4B 0.96(2) . ?
C4 H4A 0.96(2) . ?
C5 C6 1.513(2) . ?
C5 H5A 0.972(18) . ?
C5 H5B 0.931(19) . ?
C6 N1 1.494(2) . ?
C6 H6B 0.948(18) . ?
C6 H6A 0.945(19) . ?
N1 H1B 0.87(2) . ?
N1 H1C 0.90(2) . ?
N1 H1A 0.90(2) . ?
O3 H3C 0.79(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 108(2) . . ?
O2 C1 O1 122.91(14) . . ?
O2 C1 C2 123.18(14) . . ?
O1 C1 C2 113.91(13) . . ?
C1 C2 C3 112.52(13) . . ?
C1 C2 H2B 107.3(11) . . ?
C3 C2 H2B 113.8(12) . . ?
C1 C2 H2A 107.2(12) . . ?
C3 C2 H2A 111.0(11) . . ?
H2B C2 H2A 104.5(16) . . ?
C2 C3 C4 113.52(13) . . ?
C2 C3 H3A 109.1(11) . . ?
C4 C3 H3A 108.5(11) . . ?
C2 C3 H3B 110.1(13) . . ?
C4 C3 H3B 110.4(13) . . ?
H3A C3 H3B 104.8(17) . . ?
C5 C4 C3 114.64(13) . . ?
C5 C4 H4B 108.8(12) . . ?
C3 C4 H4B 109.2(11) . . ?
C5 C4 H4A 110.8(12) . . ?
C3 C4 H4A 108.1(12) . . ?
H4B C4 H4A 104.8(15) . . ?
C6 C5 C4 109.81(13) . . ?
C6 C5 H5A 108.5(10) . . ?
C4 C5 H5A 112.3(11) . . ?
C6 C5 H5B 110.6(12) . . ?
C4 C5 H5B 109.8(12) . . ?
H5A C5 H5B 105.8(15) . . ?
N1 C6 C5 111.58(14) . . ?
N1 C6 H6B 105.8(11) . . ?
C5 C6 H6B 112.7(11) . . ?
N1 C6 H6A 106.0(12) . . ?
C5 C6 H6A 110.2(12) . . ?
H6B C6 H6A 110.3(16) . . ?
C6 N1 H1B 110.6(15) . . ?
C6 N1 H1C 112.3(14) . . ?
H1B N1 H1C 107(2) . . ?
C6 N1 H1A 111.1(13) . . ?
H1B N1 H1A 110.1(19) . . ?
H1C N1 H1A 105.9(19) . . ?

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
O2 C1 C2 C3 -4.8(2) . . . . ?
O1 C1 C2 C3 174.95(14) . . . . ?
C1 C2 C3 C4 178.85(14) . . . . ?
C2 C3 C4 C5 69.73(19) . . . . ?
C3 C4 C5 C6 174.92(14) . . . . ?
C4 C5 C6 N1 173.65(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1C I1 0.90(2) 2.64(2) 3.5460(16) 176.3(19) 5_665
N1 H1A O3 0.90(2) 2.03(2) 2.9026(18) 162.5(19) .
C6 H6B I1 0.948(18) 3.309(19) 3.8704(16) 120.0(13) 5_655
C6 H6A I1 0.945(19) 3.10(2) 3.8111(17) 133.2(13) 2_655
C2 H2B I1 0.94(2) 3.26(2) 4.1741(16) 166.4(15) 2_665
O1 H1 O2 0.68(2) 2.00(2) 2.6822(17) 177(3) 7_676
O3 H3C I1 0.79(2) 2.76(2) 3.5528(12) 177(2) 2_665

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.063

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelxl_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1571892'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H14 N O2, Cl'
_chemical_formula_sum            'C6 H14 Cl N O2'
_chemical_formula_weight         167.63

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   11.2287(6)
_cell_length_b                   8.5257(4)
_cell_length_c                   9.1381(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.510(2)
_cell_angle_gamma                90
_cell_volume                     857.22(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9950
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.18

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.392
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8219
_exptl_absorpt_correction_T_max  0.8620
_exptl_absorpt_process_details   'SADABS (Bruker, 2015)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24417
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_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         3.023
_diffrn_reflns_theta_max         27.194
_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             1897
_reflns_number_gt                1661
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0286P)²+0.3207P]
 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         1897
_refine_ls_number_parameters     107
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0638
_refine_ls_wR_factor_gt          0.0611
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
Cl1 Cl 0.93564(2) 0.76475(3) 0.47790(3) 0.01675(9) Uani 1 1 d . . . . .
O2 O 0.78912(8) 0.46790(10) 0.69286(11) 0.0252(2) Uani 1 1 d . . . . .
O1 O 0.71317(8) 0.70242(11) 0.61549(10) 0.0226(2) Uani 1 1 d . . . . .
N1 N 0.05360(9) 0.53426(13) 0.74282(12) 0.0158(2) Uani 1 1 d . . . . .
C1 C 0.71600(10) 0.57072(14) 0.69515(13) 0.0169(2) Uani 1 1 d . . . . .
C2 C 0.61899(10) 0.56811(16) 0.78703(13) 0.0211(3) Uani 1 1 d . . . . .
H2A H 0.6337 0.6559 0.8593 0.025 Uiso 1 1 calc R U . . .
H2B H 0.6264 0.4693 0.8450 0.025 Uiso 1 1 calc R U . . .
C3 C 0.48935(10) 0.58101(16) 0.69705(13) 0.0197(3) Uani 1 1 d . . . . .
H3A H 0.4821 0.6765 0.6343 0.024 Uiso 1 1 calc R U . . .
H3B H 0.4715 0.4892 0.6299 0.024 Uiso 1 1 calc R U . . .
C4 C 0.39696(10) 0.58838(15) 0.79830(13) 0.0186(3) Uani 1 1 d . . . . .
H4A H 0.4139 0.5025 0.8724 0.022 Uiso 1 1 calc R U . . .
H4B H 0.4069 0.6889 0.8536 0.022 Uiso 1 1 calc R U . . .
C5 C 0.26632(10) 0.57472(15) 0.71389(13) 0.0184(3) Uani 1 1 d . . . . .
H5A H 0.2481 0.6619 0.6413 0.022 Uiso 1 1 calc R U . . .
H5B H 0.2558 0.4748 0.6575 0.022 Uiso 1 1 calc R U . . .
C6 C 0.17843(10) 0.57991(14) 0.82001(13) 0.0153(2) Uani 1 1 d . . . . .
H6A H 0.2068 0.5076 0.9046 0.018 Uiso 1 1 calc R U . . .
H6B H 0.1767 0.6873 0.8608 0.018 Uiso 1 1 calc R U . . .
H1 H 0.7730(16) 0.704(2) 0.5771(19) 0.036(5) Uiso 1 1 d . . . . .
H1A H 0.0530(14) 0.441(2) 0.6976(17) 0.028(4) Uiso 1 1 d . . . . .
H1C H 0.0247(14) 0.606(2) 0.6672(18) 0.033(4) Uiso 1 1 d . . . . .
H1B H 0.0022(15) 0.5320(19) 0.8082(18) 0.033(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.2041(15) . ?
O1 C1 1.3350(15) . ?
O1 H1 0.818(18) . ?
N1 C6 1.4897(15) . ?
N1 H1A 0.893(17) . ?
N1 H1C 0.933(17) . ?
N1 H1B 0.911(17) . ?
C1 C2 1.5024(16) . ?
C2 C3 1.5262(16) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5229(16) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5195(16) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5159(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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 O1 H1 108.6(12) . . ?
C6 N1 H1A 111.8(10) . . ?
C6 N1 H1C 109.5(10) . . ?
H1A N1 H1C 105.8(13) . . ?
C6 N1 H1B 110.8(10) . . ?
H1A N1 H1B 109.7(14) . . ?
H1C N1 H1B 109.2(14) . . ?
O2 C1 O1 123.02(11) . . ?
O2 C1 C2 124.88(11) . . ?
O1 C1 C2 112.09(10) . . ?
C1 C2 C3 114.69(10) . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C3 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C4 C3 C2 111.57(10) . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C5 C4 C3 113.21(10) . . ?
C5 C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C6 C5 C4 111.03(10) . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
N1 C6 C5 111.14(9) . . ?
N1 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
N1 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?

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
O2 C1 C2 C3 -121.06(13) . . . . ?
O1 C1 C2 C3 59.44(14) . . . . ?
C1 C2 C3 C4 -176.25(11) . . . . ?
C2 C3 C4 C5 -170.68(11) . . . . ?
C3 C4 C5 C6 179.02(10) . . . . ?
C4 C5 C6 N1 -168.41(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1C Cl1 0.933(17) 2.265(17) 3.1932(11) 173.7(13) 1_455
N1 H1B Cl1 0.911(17) 2.992(16) 3.4183(11) 110.4(12) 2_646
N1 H1B Cl1 0.911(17) 2.535(17) 3.2312(11) 133.6(13) 4_476
N1 H1B O2 0.911(17) 2.475(16) 2.9676(13) 114.3(12) 1_455
N1 H1A Cl1 0.893(17) 2.399(17) 3.2678(11) 164.2(13) 3_666
C2 H2A O1 0.99 2.63 3.5620(15) 157.5 4_576
C6 H6A Cl1 0.99 2.95 3.6352(12) 127.5 2_646
C6 H6B O2 0.99 2.49 3.3326(15) 143.1 2_656
O1 H1 Cl1 0.818(18) 2.255(18) 3.0589(9) 167.9(16) .
N1 H1C Cl1 0.933(17) 2.265(17) 3.1932(11) 173.7(13) 1_455
N1 H1B Cl1 0.911(17) 2.992(16) 3.4183(11) 110.4(12) 2_646
N1 H1B Cl1 0.911(17) 2.535(17) 3.2312(11) 133.6(13) 4_476
N1 H1B O2 0.911(17) 2.475(16) 2.9676(13) 114.3(12) 1_455
N1 H1A Cl1 0.893(17) 2.399(17) 3.2678(11) 164.2(13) 3_666
C2 H2A O1 0.99 2.63 3.5620(15) 157.5 4_576
C6 H6A Cl1 0.99 2.95 3.6352(12) 127.5 2_646
C6 H6B O2 0.99 2.49 3.3326(15) 143.1 2_656
O1 H1 Cl1 0.818(18) 2.255(18) 3.0589(9) 167.9(16) .

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelxl_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1571890'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H10 N O2, Br'
_chemical_formula_sum            'C4 H10 Br N O2'
_chemical_formula_weight         184.04

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   13.3778(13)
_cell_length_b                   6.4784(6)
_cell_length_c                   15.7657(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1366.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9908
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      27.16

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.789
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    5.935
_shelx_estimated_absorpt_T_min   0.237
_shelx_estimated_absorpt_T_max   0.470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1941
_exptl_absorpt_correction_T_max  0.2739
_exptl_absorpt_process_details   'SADABS (Bruker, 2015)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36170
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0660
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.584
_diffrn_reflns_theta_max         27.216
_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             1521
_reflns_number_gt                1356
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0133P)²+0.5897P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0079(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1521
_refine_ls_number_parameters     114
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0196
_refine_ls_R_factor_gt           0.0152
_refine_ls_wR_factor_ref         0.0365
_refine_ls_wR_factor_gt          0.0352
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
Br1 Br 0.85397(2) 0.27763(2) 0.54602(2) 0.01611(7) Uani 1 1 d . . . . .
O2 O 0.62656(9) 0.29038(19) 0.38598(7) 0.0277(3) Uani 1 1 d . . . . .
O1 O 0.78586(9) 0.32126(19) 0.34580(7) 0.0235(3) Uani 1 1 d . . . . .
N1 N 0.58937(11) 0.2225(2) 0.05861(8) 0.0171(3) Uani 1 1 d . . . . .
C1 C 0.68807(12) 0.3083(2) 0.33065(10) 0.0167(3) Uani 1 1 d . . . . .
C2 C 0.66284(12) 0.3240(2) 0.23810(10) 0.0175(3) Uani 1 1 d . . . . .
C3 C 0.57353(13) 0.1878(2) 0.21579(9) 0.0178(3) Uani 1 1 d . . . . .
C4 C 0.52235(12) 0.2431(2) 0.13301(10) 0.0167(3) Uani 1 1 d . . . . .
H1 H 0.7941(17) 0.317(3) 0.3941(14) 0.041(6) Uiso 1 1 d . . . . .
H1A H 0.6165(14) 0.100(3) 0.0569(11) 0.030(5) Uiso 1 1 d . . . . .
H1B H 0.5599(16) 0.242(3) 0.0124(14) 0.028(5) Uiso 1 1 d . . . . .
H1C H 0.6421(16) 0.320(4) 0.0603(13) 0.042(7) Uiso 1 1 d . . . . .
H3A H 0.5235(13) 0.200(2) 0.2608(12) 0.018(4) Uiso 1 1 d . . . . .
H4B H 0.5000(12) 0.385(3) 0.1331(10) 0.018(4) Uiso 1 1 d . . . . .
H2B H 0.6468(12) 0.466(3) 0.2292(11) 0.023(4) Uiso 1 1 d . . . . .
H2A H 0.7199(16) 0.296(3) 0.2057(10) 0.027(5) Uiso 1 1 d . . . . .
H4A H 0.4685(13) 0.152(3) 0.1226(10) 0.022(4) Uiso 1 1 d . . . . .
H3B H 0.5935(13) 0.046(3) 0.2156(10) 0.024(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.2047(19) . ?
O1 C1 1.3326(19) . ?
O1 H1 0.77(2) . ?
N1 C4 1.482(2) . ?
N1 H1A 0.87(2) . ?
N1 H1B 0.84(2) . ?
N1 H1C 0.95(2) . ?
C1 C2 1.501(2) . ?
C2 C3 1.526(2) . ?
C2 H2B 0.958(18) . ?
C2 H2A 0.94(2) . ?
C3 C4 1.517(2) . ?
C3 H3A 0.978(19) . ?
C3 H3B 0.958(18) . ?
C4 H4B 0.969(16) . ?
C4 H4A 0.946(17) . ?

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 O1 H1 108.4(17) . . ?
C4 N1 H1A 111.0(12) . . ?
C4 N1 H1B 113.0(15) . . ?
H1A N1 H1B 107.6(17) . . ?
C4 N1 H1C 111.6(13) . . ?
H1A N1 H1C 107.4(18) . . ?
H1B N1 H1C 106.0(18) . . ?
O2 C1 O1 123.16(15) . . ?
O2 C1 C2 123.83(15) . . ?
O1 C1 C2 112.99(14) . . ?
C1 C2 C3 111.15(13) . . ?
C1 C2 H2B 105.0(10) . . ?
C3 C2 H2B 110.4(10) . . ?
C1 C2 H2A 109.5(11) . . ?
C3 C2 H2A 113.6(11) . . ?
H2B C2 H2A 106.8(15) . . ?
C4 C3 C2 114.51(13) . . ?
C4 C3 H3A 107.2(10) . . ?
C2 C3 H3A 108.8(10) . . ?
C4 C3 H3B 110.5(10) . . ?
C2 C3 H3B 109.7(11) . . ?
H3A C3 H3B 105.7(13) . . ?
N1 C4 C3 112.74(13) . . ?
N1 C4 H4B 105.9(9) . . ?
C3 C4 H4B 111.3(9) . . ?
N1 C4 H4A 105.5(10) . . ?
C3 C4 H4A 110.2(10) . . ?
H4B C4 H4A 111.1(14) . . ?

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
O2 C1 C2 C3 -36.3(2) . . . . ?
O1 C1 C2 C3 145.24(14) . . . . ?
C1 C2 C3 C4 161.38(13) . . . . ?
C2 C3 C4 N1 61.58(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 Br1 0.77(2) 2.54(2) 3.2977(12) 169(2) .
N1 H1A Br1 0.87(2) 2.48(2) 3.3337(14) 164.5(17) 2_654
N1 H1B Br1 0.84(2) 2.91(2) 3.5729(15) 137.0(18) 6_556
N1 H1B O2 0.84(2) 2.19(2) 2.7680(18) 125.8(19) 7_565
N1 H1C Br1 0.95(2) 2.62(2) 3.3315(14) 132.6(17) 2_664
N1 H1C Br1 0.95(2) 2.91(2) 3.5453(15) 125.2(17) 7_565
C2 H2A Br1 0.94(2) 3.128(19) 4.0177(16) 159.4(14) 7_565

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.054

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelxl_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1571893'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ' 2(C6 H14 N O2), 2(Br), H2 O'
_chemical_formula_sum            'C12 H30 Br2 N2 O5'
_chemical_formula_weight         442.20

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'
Br Br -0.2901 2.4595 '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                   29.6835(16)
_cell_length_b                   4.9623(3)
_cell_length_c                   12.5219(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.194(2)
_cell_angle_gamma                90
_cell_volume                     1843.10(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9932
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      27.14

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.272
_exptl_crystal_size_min          0.128
_exptl_absorpt_coefficient_mu    4.418
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3790
_exptl_absorpt_correction_T_max  0.6467
_exptl_absorpt_process_details   'SADABS (Bruker, 2015)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25382
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.747
_diffrn_reflns_theta_max         27.157
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2047
_reflns_number_gt                1835
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0153P)²+1.7059P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00240(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2047
_refine_ls_number_parameters     155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0166
_refine_ls_wR_factor_ref         0.0407
_refine_ls_wR_factor_gt          0.0389
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
H1B H 0.5348(7) 0.259(4) 0.0699(16) 0.038(6) Uiso 1 1 d . . . . .
H1C H 0.5540(7) 0.526(4) 0.0512(16) 0.030(5) Uiso 1 1 d . . . . .
H1A H 0.5340(7) 0.467(4) 0.1521(15) 0.027(5) Uiso 1 1 d . . . . .
H6B H 0.6104(6) 0.219(3) 0.0898(13) 0.017(4) Uiso 1 1 d . . . . .
H6A H 0.5877(6) 0.161(3) 0.1997(14) 0.019(4) Uiso 1 1 d . . . . .
H2B H 0.6488(6) 0.837(3) 0.3918(13) 0.015(4) Uiso 1 1 d . . . . .
H5A H 0.6026(6) 0.612(3) 0.2545(14) 0.020(4) Uiso 1 1 d . . . . .
H5B H 0.6268(6) 0.657(4) 0.1498(14) 0.024(5) Uiso 1 1 d . . . . .
H2A H 0.6752(6) 0.621(3) 0.4544(14) 0.020(4) Uiso 1 1 d . . . . .
H4B H 0.6809(6) 0.313(4) 0.1968(14) 0.024(5) Uiso 1 1 d . . . . .
H3A H 0.7249(6) 0.550(3) 0.3165(13) 0.020(4) Uiso 1 1 d . . . . .
H4A H 0.6579(6) 0.287(4) 0.3076(14) 0.022(4) Uiso 1 1 d . . . . .
H3B H 0.7005(6) 0.778(4) 0.2469(14) 0.022(4) Uiso 1 1 d . . . . .
Br1 Br 0.44393(2) 0.11835(3) 0.08293(2) 0.01976(7) Uani 1 1 d . . . . .
O1 O 0.69425(4) 1.0997(2) 0.52933(9) 0.0209(2) Uani 1 1 d . . . . .
O2 O 0.74714(4) 1.0134(2) 0.41197(8) 0.0206(2) Uani 1 1 d . . . . .
C1 C 0.71023(5) 0.9678(3) 0.44719(11) 0.0148(3) Uani 1 1 d . . . . .
C2 C 0.67854(5) 0.7581(3) 0.40134(12) 0.0153(3) Uani 1 1 d . . . . .
C3 C 0.69586(5) 0.6324(3) 0.29992(12) 0.0175(3) Uani 1 1 d . . . . .
C4 C 0.66479(5) 0.4167(3) 0.25127(12) 0.0177(3) Uani 1 1 d . . . . .
C5 C 0.62093(5) 0.5261(3) 0.20030(12) 0.0166(3) Uani 1 1 d . . . . .
C6 C 0.59446(5) 0.2987(3) 0.14714(12) 0.0165(3) Uani 1 1 d . . . . .
N1 N 0.55025(5) 0.3963(3) 0.10107(11) 0.0195(3) Uani 1 1 d . . . . .
O3 O 0.5000 0.7123(4) 0.2500 0.0253(4) Uani 1 2 d S T P . .
H1 H 0.7117(7) 1.201(4) 0.5457(16) 0.030 Uiso 1 1 d . U . . .
H3C H 0.5144(7) 0.814(4) 0.2883(15) 0.030 Uiso 1 1 d . U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3222(18) . ?
O1 H1 0.75(2) . ?
O2 C1 1.2180(18) . ?
C1 C2 1.502(2) . ?
C2 C3 1.522(2) . ?
C2 H2B 0.968(17) . ?
C2 H2A 0.959(17) . ?
C3 C4 1.524(2) . ?
C3 H3A 0.971(18) . ?
C3 H3B 0.993(18) . ?
C4 C5 1.528(2) . ?
C4 H4B 0.991(18) . ?
C4 H4A 0.982(18) . ?
C5 C6 1.515(2) . ?
C5 H5A 0.983(18) . ?
C5 H5B 0.929(18) . ?
C6 N1 1.4936(19) . ?
C6 H6B 0.961(17) . ?
C6 H6A 0.974(18) . ?
N1 H1B 0.90(2) . ?
N1 H1C 0.91(2) . ?
N1 H1A 0.89(2) . ?
O3 H3C 0.808(19) . ?

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 O1 H1 106.5(16) . . ?
O2 C1 O1 122.96(13) . . ?
O2 C1 C2 123.32(13) . . ?
O1 C1 C2 113.72(13) . . ?
C1 C2 C3 112.11(12) . . ?
C1 C2 H2B 108.7(10) . . ?
C3 C2 H2B 113.5(10) . . ?
C1 C2 H2A 107.9(10) . . ?
C3 C2 H2A 109.5(10) . . ?
H2B C2 H2A 104.8(14) . . ?
C2 C3 C4 113.75(13) . . ?
C2 C3 H3A 108.7(10) . . ?
C4 C3 H3A 108.0(10) . . ?
C2 C3 H3B 108.6(10) . . ?
C4 C3 H3B 109.9(10) . . ?
H3A C3 H3B 107.7(14) . . ?
C3 C4 C5 114.23(12) . . ?
C3 C4 H4B 109.8(11) . . ?
C5 C4 H4B 108.8(11) . . ?
C3 C4 H4A 108.2(10) . . ?
C5 C4 H4A 109.6(10) . . ?
H4B C4 H4A 105.9(14) . . ?
C6 C5 C4 109.79(12) . . ?
C6 C5 H5A 109.4(10) . . ?
C4 C5 H5A 110.6(10) . . ?
C6 C5 H5B 109.4(11) . . ?
C4 C5 H5B 110.7(11) . . ?
H5A C5 H5B 106.9(14) . . ?
N1 C6 C5 111.19(13) . . ?
N1 C6 H6B 107.2(10) . . ?
C5 C6 H6B 111.9(10) . . ?
N1 C6 H6A 106.7(11) . . ?
C5 C6 H6A 110.0(10) . . ?
H6B C6 H6A 109.7(14) . . ?
C6 N1 H1B 110.4(13) . . ?
C6 N1 H1C 111.5(12) . . ?
H1B N1 H1C 108.1(17) . . ?
C6 N1 H1A 110.1(12) . . ?
H1B N1 H1A 109.2(18) . . ?
H1C N1 H1A 107.5(17) . . ?

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
O2 C1 C2 C3 -5.9(2) . . . . ?
O1 C1 C2 C3 173.78(12) . . . . ?
C1 C2 C3 C4 179.55(12) . . . . ?
C2 C3 C4 C5 70.99(18) . . . . ?
C3 C4 C5 C6 175.58(13) . . . . ?
C4 C5 C6 N1 177.19(12) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A Br1 0.89(2) 3.274(19) 3.4437(14) 93.5(13) .
N1 H1C Br1 0.91(2) 2.44(2) 3.3422(14) 174.3(17) 5_665
N1 H1A O3 0.89(2) 2.02(2) 2.8939(18) 166.2(18) .
C6 H6B Br1 0.961(17) 3.132(17) 3.6918(15) 118.7(12) 5_655
C6 H6A Br1 0.974(18) 2.921(18) 3.7174(15) 139.7(12) 2_655
C2 H2B Br1 0.968(17) 3.114(17) 4.0626(15) 166.9(13) 2_665
O1 H1 O2 0.75(2) 1.93(2) 2.6749(15) 175(2) 7_676
O3 H3C Br1 0.808(19) 2.501(19) 3.3076(11) 176(2) 2_665
N1 H1A Br1 0.89(2) 3.274(19) 3.4437(14) 93.5(13) .
N1 H1C Br1 0.91(2) 2.44(2) 3.3422(14) 174.3(17) 5_665
N1 H1A O3 0.89(2) 2.02(2) 2.8939(18) 166.2(18) .
C6 H6B Br1 0.961(17) 3.132(17) 3.6918(15) 118.7(12) 5_655
C6 H6A Br1 0.974(18) 2.921(18) 3.7174(15) 139.7(12) 2_655
C2 H2B Br1 0.968(17) 3.114(17) 4.0626(15) 166.9(13) 2_665
O1 H1 O2 0.75(2) 1.93(2) 2.6749(15) 175(2) 7_676
O3 H3C Br1 0.808(19) 2.501(19) 3.3076(11) 176(2) 2_665

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.052

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_shelxl_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1571891'
_audit_update_record             
;
2017-08-31 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H10 N O2, I'
_chemical_formula_sum            'C4 H10 I N O2'
_chemical_formula_weight         231.03

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

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

_cell_length_a                   9.5887(4)
_cell_length_b                   6.0522(3)
_cell_length_c                   12.6513(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     734.19(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      28.39

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.090
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.137
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.061
_exptl_absorpt_coefficient_mu    4.286
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3680
_exptl_absorpt_correction_T_max  0.4426
_exptl_absorpt_process_details   'SADABS (Bruker, 2015)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21535
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.665
_diffrn_reflns_theta_max         28.398
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.001
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.001
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.001
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1010
_reflns_number_gt                958
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0105P)²+0.3015P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0074(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1010
_refine_ls_number_parameters     72
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0125
_refine_ls_R_factor_gt           0.0110
_refine_ls_wR_factor_ref         0.0252
_refine_ls_wR_factor_gt          0.0249
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.135
_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
I1 I 0.52462(2) 0.7500 0.13232(2) 0.01699(6) Uani 1 2 d S T P . .
O2 O 0.44505(13) 0.7500 0.50002(10) 0.0175(3) Uani 1 2 d S T P . .
O1 O 0.63060(16) 0.7500 0.39273(11) 0.0244(3) Uani 1 2 d S T P . .
N1 N 0.68417(18) 0.7500 0.87479(12) 0.0176(3) Uani 1 2 d S T P . .
C1 C 0.5703(2) 0.7500 0.48755(13) 0.0147(3) Uani 1 2 d S T P . .
C2 C 0.67853(19) 0.7500 0.57325(13) 0.0169(4) Uani 1 2 d S T P . .
C3 C 0.6195(2) 0.7500 0.68409(13) 0.0172(4) Uani 1 2 d S T P . .
C4 C 0.73708(19) 0.7500 0.76389(14) 0.0171(4) Uani 1 2 d S T P . .
H1A H 0.755(3) 0.7500 0.9162(18) 0.024(6) Uiso 1 2 d S . P . .
H2A H 0.7386(17) 0.877(3) 0.5631(12) 0.029(4) Uiso 1 1 d . . . . .
H4A H 0.7930(16) 0.881(3) 0.7538(11) 0.029(4) Uiso 1 1 d . . . . .
H3A H 0.5627(17) 0.881(3) 0.6951(13) 0.031(4) Uiso 1 1 d . . . . .
H1 H 0.571(4) 0.7500 0.350(2) 0.042(8) Uiso 1 2 d S . P . .
H1B H 0.633(2) 0.870(3) 0.8872(12) 0.037(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C1 1.211(2) . ?
O1 C1 1.332(2) . ?
O1 H1 0.79(3) . ?
N1 C4 1.492(2) . ?
N1 H1A 0.86(3) . ?
N1 H1B 0.89(2) . ?
C1 C2 1.501(2) . ?
C2 C3 1.512(2) . ?
C2 H2A 0.971(17) . ?
C3 C4 1.513(2) . ?
C3 H3A 0.970(17) . ?
C4 H4A 0.968(17) . ?

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 O1 H1 107(2) . . ?
C4 N1 H1A 107.7(16) . . ?
C4 N1 H1B 110.7(11) . . ?
H1A N1 H1B 109.2(14) . . ?
O2 C1 O1 123.24(16) . . ?
O2 C1 C2 126.27(15) . . ?
O1 C1 C2 110.49(16) . . ?
C1 C2 C3 114.26(16) . . ?
C1 C2 H2A 108.3(9) . . ?
C3 C2 H2A 110.2(9) . . ?
C2 C3 C4 109.85(15) . . ?
C2 C3 H3A 110.1(10) . . ?
C4 C3 H3A 108.8(10) . . ?
N1 C4 C3 111.96(15) . . ?
N1 C4 H4A 108.2(9) . . ?
C3 C4 H4A 108.9(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 C3 0.000(0) . . . . ?
O1 C1 C2 C3 180.000(0) . . . . ?
C1 C2 C3 C4 180.000(0) . . . . ?
C2 C3 C4 N1 180.000(0) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O2 0.86(3) 2.11(3) 2.961(2) 173(2) 6_657
C2 H2A I1 0.971(17) 3.318(16) 4.2211(13) 155.6(12) 2_675
C4 H4A I1 0.968(17) 3.224(16) 4.1411(12) 158.8(11) 2_675
C3 H3A I1 0.970(17) 3.235(17) 4.0572(12) 143.6(12) 5_676
O1 H1 I1 0.79(3) 2.79(3) 3.4476(14) 142(3) .
N1 H1B I1 0.89(2) 2.77(2) 3.6295(10) 164.7(14) 5_676
N1 H1A O2 0.86(3) 2.11(3) 2.961(2) 173(2) 6_657
C2 H2A I1 0.971(17) 3.318(16) 4.2211(13) 155.6(12) 2_675
C4 H4A I1 0.968(17) 3.224(16) 4.1411(12) 158.8(11) 2_675
C3 H3A I1 0.970(17) 3.235(17) 4.0572(12) 143.6(12) 5_676
O1 H1 I1 0.79(3) 2.79(3) 3.4476(14) 142(3) .
N1 H1B I1 0.89(2) 2.77(2) 3.6295(10) 164.7(14) 5_676

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.091

_shelxl_version_number           2013-2

