# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_glo9476
_database_code_depnum_ccdc_archive 'CCDC 2006231'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2020-05-27 deposited with the CCDC.	2021-03-04 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H18 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         182.26

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.8352(5)
_cell_length_b                   9.3209(4)
_cell_length_c                   11.4836(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.743(3)
_cell_angle_gamma                90
_cell_volume                     996.91(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3813
_cell_measurement_theta_min      5.1655
_cell_measurement_theta_max      66.3913
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400

_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Kappa CCD APEXII'
_diffrn_measurement_method       'phi / omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            14466
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_theta_min         5.17
_diffrn_reflns_theta_max         66.72
_diffrn_reflns_theta_full        66.72
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13

_refine_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.

The hydrogen at N1 atom was refined freely.
;

_reflns_number_total             1752
_reflns_number_gt                1334
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.1017
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.054
_refine_ls_number_reflns         1752
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+0.3186P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.195
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v2016.1-0 (Bruker AXS Inc., 2016)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.65297(12) 0.26082(12) 0.16985(10) 0.0267(3) Uani d . . . 1 . .
N N1 0.62143(15) 0.57753(15) 0.40879(13) 0.0238(3) Uani d . . . 1 . .
H H1 0.6605(19) 0.644(2) 0.3777(16) 0.023(5) Uiso d . . . 1 . .
C C2 0.72191(17) 0.45950(18) 0.45671(14) 0.0231(4) Uani d . . . 1 . .
H H2 0.6716 0.3834 0.4887 0.028 Uiso calc U . R 1 . .
C C3 0.76696(17) 0.39591(18) 0.35198(14) 0.0232(4) Uani d . . . 1 . .
H H3A 0.8284 0.4661 0.3277 0.028 Uiso calc U . R 1 . .
H H3B 0.8252 0.3088 0.3822 0.028 Uiso calc U . R 1 . .
C C4 0.64227(18) 0.35721(17) 0.24053(15) 0.0230(4) Uani d . . . 1 . .
N N5 0.52015(14) 0.43501(15) 0.22081(12) 0.0227(3) Uani d . . . 1 . .
C C6 0.39109(17) 0.39286(18) 0.12023(15) 0.0258(4) Uani d . . . 1 . .
H H6A 0.3295 0.3325 0.1536 0.031 Uiso calc U . R 1 . .
H H6B 0.4197 0.3347 0.0598 0.031 Uiso calc U . R 1 . .
C C7 0.30577(18) 0.52228(19) 0.05565(14) 0.0261(4) Uani d . . . 1 . .
H H7 0.3677 0.5789 0.0183 0.031 Uiso calc U . R 1 . .
C C8 0.26969(18) 0.61702(19) 0.14992(15) 0.0266(4) Uani d . . . 1 . .
H H8A 0.2194 0.7045 0.109 0.032 Uiso calc U . R 1 . .
H H8B 0.2045 0.5646 0.1852 0.032 Uiso calc U . R 1 . .
C C9 0.40569(18) 0.65943(18) 0.25258(15) 0.0267(4) Uani d . . . 1 . .
H H9A 0.4658 0.7203 0.218 0.032 Uiso calc U . R 1 . .
H H9B 0.3791 0.717 0.3144 0.032 Uiso calc U . R 1 . .
C C10 0.49279(17) 0.53046(17) 0.31553(14) 0.0230(4) Uani d . . . 1 . .
H H10 0.4339 0.4755 0.3569 0.028 Uiso calc U . R 1 . .
C C11 0.84928(18) 0.51222(19) 0.56178(14) 0.0260(4) Uani d . . . 1 . .
H H11A 0.8958 0.5915 0.5332 0.039 Uiso calc U . R 1 . .
H H11B 0.918 0.4336 0.591 0.039 Uiso calc U . R 1 . .
H H11C 0.8164 0.5456 0.6291 0.039 Uiso calc U . R 1 . .
C C12 0.17147(19) 0.4752(2) -0.04780(16) 0.0306(4) Uani d . . . 1 . .
H H12A 0.1119 0.4147 -0.0138 0.046 Uiso calc U . R 1 . .
H H12B 0.1998 0.4208 -0.1093 0.046 Uiso calc U . R 1 . .
H H12C 0.1166 0.5601 -0.0866 0.046 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C4 . 1.2377(19) ?
N1 C10 . 1.439(2) ?
N1 C2 . 1.463(2) ?
N1 H1 . 0.864(19) ?
C2 C11 . 1.515(2) ?
C2 C3 . 1.529(2) ?
C2 H2 . 1.0 ?
C3 C4 . 1.504(2) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 N5 . 1.358(2) ?
N5 C6 . 1.469(2) ?
N5 C10 . 1.495(2) ?
C6 C7 . 1.520(2) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 C8 . 1.525(2) ?
C7 C12 . 1.530(2) ?
C7 H7 . 1.0 ?
C8 C9 . 1.524(2) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C10 . 1.518(2) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 H10 . 1.0 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 N1 C2 . . 112.14(13) ?
C10 N1 H1 . . 108.2(11) ?
C2 N1 H1 . . 111.0(12) ?
N1 C2 C11 . . 109.96(13) ?
N1 C2 C3 . . 109.10(13) ?
C11 C2 C3 . . 112.20(14) ?
N1 C2 H2 . . 108.5 ?
C11 C2 H2 . . 108.5 ?
C3 C2 H2 . . 108.5 ?
C4 C3 C2 . . 113.53(14) ?
C4 C3 H3A . . 108.9 ?
C2 C3 H3A . . 108.9 ?
C4 C3 H3B . . 108.9 ?
C2 C3 H3B . . 108.9 ?
H3A C3 H3B . . 107.7 ?
O1 C4 N5 . . 122.35(15) ?
O1 C4 C3 . . 120.94(15) ?
N5 C4 C3 . . 116.69(14) ?
C4 N5 C6 . . 118.87(14) ?
C4 N5 C10 . . 123.55(13) ?
C6 N5 C10 . . 114.79(13) ?
N5 C6 C7 . . 111.94(14) ?
N5 C6 H6A . . 109.2 ?
C7 C6 H6A . . 109.2 ?
N5 C6 H6B . . 109.2 ?
C7 C6 H6B . . 109.2 ?
H6A C6 H6B . . 107.9 ?
C6 C7 C8 . . 109.34(13) ?
C6 C7 C12 . . 110.79(14) ?
C8 C7 C12 . . 112.18(14) ?
C6 C7 H7 . . 108.1 ?
C8 C7 H7 . . 108.1 ?
C12 C7 H7 . . 108.1 ?
C9 C8 C7 . . 110.66(14) ?
C9 C8 H8A . . 109.5 ?
C7 C8 H8A . . 109.5 ?
C9 C8 H8B . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 108.1 ?
C10 C9 C8 . . 112.57(14) ?
C10 C9 H9A . . 109.1 ?
C8 C9 H9A . . 109.1 ?
C10 C9 H9B . . 109.1 ?
C8 C9 H9B . . 109.1 ?
H9A C9 H9B . . 107.8 ?
N1 C10 N5 . . 113.72(13) ?
N1 C10 C9 . . 109.87(13) ?
N5 C10 C9 . . 109.32(13) ?
N1 C10 H10 . . 107.9 ?
N5 C10 H10 . . 107.9 ?
C9 C10 H10 . . 107.9 ?
C2 C11 H11A . . 109.5 ?
C2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C7 C12 H12A . . 109.5 ?
C7 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C7 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 N1 C2 C11 . . . . -175.18(13) ?
C10 N1 C2 C3 . . . . 61.37(17) ?
N1 C2 C3 C4 . . . . -51.64(18) ?
C11 C2 C3 C4 . . . . -173.74(14) ?
C2 C3 C4 O1 . . . . -152.79(15) ?
C2 C3 C4 N5 . . . . 28.6(2) ?
O1 C4 N5 C6 . . . . 7.1(2) ?
C3 C4 N5 C6 . . . . -174.24(14) ?
O1 C4 N5 C10 . . . . 167.16(15) ?
C3 C4 N5 C10 . . . . -14.2(2) ?
C4 N5 C6 C7 . . . . -142.53(15) ?
C10 N5 C6 C7 . . . . 55.74(18) ?
N5 C6 C7 C8 . . . . -55.37(18) ?
N5 C6 C7 C12 . . . . -179.51(14) ?
C6 C7 C8 C9 . . . . 55.64(18) ?
C12 C7 C8 C9 . . . . 178.97(14) ?
C7 C8 C9 C10 . . . . -56.21(19) ?
C2 N1 C10 N5 . . . . -46.55(19) ?
C2 N1 C10 C9 . . . . -169.44(14) ?
C4 N5 C10 N1 . . . . 22.9(2) ?
C6 N5 C10 N1 . . . . -176.30(13) ?
C4 N5 C10 C9 . . . . 146.12(15) ?
C6 N5 C10 C9 . . . . -53.11(18) ?
C8 C9 C10 N1 . . . . 178.34(14) ?
C8 C9 C10 N5 . . . . 52.89(18) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1 O1 2_655 0.864(19) 2.344(19) 3.1536(19) 156.1(16) ?


####################################################################### 
# 
# 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_glo9508
_database_code_depnum_ccdc_archive 'CCDC 2006232'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut WWU University of Muenster
Germany
;
_audit_update_record             
;
2020-05-27 deposited with the CCDC.	2021-03-04 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H20 Cl2 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         255.18
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.3482(5)
_cell_length_b                   6.0629(3)
_cell_length_c                   13.2849(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.642(2)
_cell_angle_gamma                90
_cell_volume                     644.24(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1130
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             272

_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173.(2)

_diffrn_source                   'Mo rotating anode'
_diffrn_source_type              'Mo rotating anode'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Montel mirror'

_diffrn_measurement_device_type  'rotating anode Nonius FR591'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            4170
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_unetI/netI     0.0396
_diffrn_reflns_theta_min         4.22
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_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.

The hydrogens at O1 and N1 atoms were refined freely.
;

_reflns_number_total             1959
_reflns_number_gt                1802
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0644
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1517
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_number_reflns         1959
_refine_ls_number_parameters     150
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0782P)²+0.9832P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.271
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 645 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(13)

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'

_computing_data_collection       
;

Collect (Nonius B.V., 1998)
;
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.3077(6) -0.0168(12) 0.8767(4) 0.0273(10) Uani d . . D 1 . .
H H1A 0.371(8) 0.098(13) 0.912(5) 0.022(17) Uiso d . . . 1 . .
H H1B 0.344(9) -0.153(7) 0.899(6) 0.05(2) Uiso d . . D 1 . .
O O1 -0.0501(6) -0.2946(9) 0.6404(3) 0.0385(12) Uani d . . . 1 . .
C C2 0.1345(7) 0.0058(13) 0.8883(4) 0.0288(13) Uani d . . . 1 . .
H H2 0.0881 0.1536 0.8617 0.035 Uiso calc U . R 1 . .
C C3 0.0307(8) -0.1734(13) 0.8197(5) 0.0328(15) Uani d . . . 1 . .
H H3A 0.0606 -0.3174 0.8552 0.039 Uiso calc U . R 1 . .
H H3B -0.0888 -0.1457 0.8126 0.039 Uiso calc U . R 1 . .
C C4 0.0538(8) -0.1871(12) 0.7130(4) 0.0298(14) Uani d . . . 1 . .
N N5 0.1792(6) -0.0867(9) 0.6909(4) 0.0252(11) Uani d . . . 1 . .
C C6 0.1906(8) -0.0709(12) 0.5820(4) 0.0335(16) Uani d . . . 1 . .
H H6A 0.1877 0.0861 0.561 0.04 Uiso calc U . R 1 . .
H H6B 0.0935 -0.1462 0.5336 0.04 Uiso calc U . R 1 . .
C C7 0.3513(8) -0.1763(13) 0.5736(5) 0.0346(16) Uani d . . . 1 . .
H H7 0.3582 -0.1507 0.5006 0.042 Uiso calc U . R 1 . .
C C8 0.4985(8) -0.0565(13) 0.6490(5) 0.0381(17) Uani d . . . 1 . .
H H8A 0.6041 -0.1282 0.647 0.046 Uiso calc U . R 1 . .
H H8B 0.5011 0.0981 0.6255 0.046 Uiso calc U . R 1 . .
C C9 0.4868(7) -0.0586(14) 0.7614(5) 0.0379(19) Uani d . . . 1 . .
H H9A 0.5769 0.0348 0.8059 0.046 Uiso calc U . R 1 . .
H H9B 0.5041 -0.211 0.7891 0.046 Uiso calc U . R 1 . .
C C10 0.3175(7) 0.0259(11) 0.7687(4) 0.0281(14) Uani d . . . 1 . .
H H10 0.3098 0.1883 0.7549 0.034 Uiso calc U . R 1 . .
C C11 0.1429(8) -0.0151(17) 1.0030(5) 0.0424(16) Uani d . . . 1 . .
H H11A 0.0306 0.0026 1.0111 0.064 Uiso calc U . R 1 . .
H H11B 0.2167 0.0994 1.0434 0.064 Uiso calc U . R 1 . .
H H11C 0.1868 -0.1608 1.0288 0.064 Uiso calc U . R 1 . .
C C12 0.3514(10) -0.4248(14) 0.5911(6) 0.048(2) Uani d . . . 1 . .
H H12A 0.3371 -0.4551 0.6605 0.073 Uiso calc U . R 1 . .
H H12B 0.4579 -0.487 0.5873 0.073 Uiso calc U . R 1 . .
H H12C 0.2594 -0.4922 0.5368 0.073 Uiso calc U . R 1 . .
Cl Cl1 0.37162(19) 0.4865(3) 0.92481(12) 0.0380(4) Uani d . . . 1 . .
Cl Cl2 -0.1832(3) -0.6540(4) 0.71840(14) 0.0569(6) Uani d . . . 1 . .
H H2A -0.104(11) -0.422(17) 0.669(7) 0.06(3) Uiso d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C10 . 1.484(7) ?
N1 C2 . 1.504(7) ?
N1 H1A . 0.92(7) ?
N1 H1B . 0.90(3) ?
O1 C4 . 1.275(8) ?
O1 H2A . 1.02(10) ?
C2 C11 . 1.510(8) ?
C2 C3 . 1.520(9) ?
C2 H2 . 1.0 ?
C3 C4 . 1.486(8) ?
C3 H3A . 0.99 ?
C3 H3B . 0.99 ?
C4 N5 . 1.315(8) ?
N5 C10 . 1.478(7) ?
N5 C6 . 1.480(7) ?
C6 C7 . 1.519(9) ?
C6 H6A . 0.99 ?
C6 H6B . 0.99 ?
C7 C12 . 1.525(12) ?
C7 C8 . 1.528(9) ?
C7 H7 . 1.0 ?
C8 C9 . 1.525(8) ?
C8 H8A . 0.99 ?
C8 H8B . 0.99 ?
C9 C10 . 1.531(9) ?
C9 H9A . 0.99 ?
C9 H9B . 0.99 ?
C10 H10 . 1.0 ?
C11 H11A . 0.98 ?
C11 H11B . 0.98 ?
C11 H11C . 0.98 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
Cl2 H2A . 1.76(10) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C10 N1 C2 . . 113.9(4) ?
C10 N1 H1A . . 100.(4) ?
C2 N1 H1A . . 108.(4) ?
C10 N1 H1B . . 112.(5) ?
C2 N1 H1B . . 107.(5) ?
H1A N1 H1B . . 116.(6) ?
C4 O1 H2A . . 113.(5) ?
N1 C2 C11 . . 109.1(5) ?
N1 C2 C3 . . 105.8(5) ?
C11 C2 C3 . . 113.5(6) ?
N1 C2 H2 . . 109.4 ?
C11 C2 H2 . . 109.4 ?
C3 C2 H2 . . 109.4 ?
C4 C3 C2 . . 113.9(5) ?
C4 C3 H3A . . 108.8 ?
C2 C3 H3A . . 108.8 ?
C4 C3 H3B . . 108.8 ?
C2 C3 H3B . . 108.8 ?
H3A C3 H3B . . 107.7 ?
O1 C4 N5 . . 118.7(5) ?
O1 C4 C3 . . 120.2(6) ?
N5 C4 C3 . . 121.0(5) ?
C4 N5 C10 . . 124.8(5) ?
C4 N5 C6 . . 121.8(5) ?
C10 N5 C6 . . 113.4(4) ?
N5 C6 C7 . . 110.5(5) ?
N5 C6 H6A . . 109.6 ?
C7 C6 H6A . . 109.6 ?
N5 C6 H6B . . 109.6 ?
C7 C6 H6B . . 109.6 ?
H6A C6 H6B . . 108.1 ?
C6 C7 C12 . . 111.5(6) ?
C6 C7 C8 . . 108.3(6) ?
C12 C7 C8 . . 113.9(6) ?
C6 C7 H7 . . 107.6 ?
C12 C7 H7 . . 107.6 ?
C8 C7 H7 . . 107.6 ?
C9 C8 C7 . . 111.9(5) ?
C9 C8 H8A . . 109.2 ?
C7 C8 H8A . . 109.2 ?
C9 C8 H8B . . 109.2 ?
C7 C8 H8B . . 109.2 ?
H8A C8 H8B . . 107.9 ?
C8 C9 C10 . . 112.2(5) ?
C8 C9 H9A . . 109.2 ?
C10 C9 H9A . . 109.2 ?
C8 C9 H9B . . 109.2 ?
C10 C9 H9B . . 109.2 ?
H9A C9 H9B . . 107.9 ?
N5 C10 N1 . . 110.3(5) ?
N5 C10 C9 . . 110.6(5) ?
N1 C10 C9 . . 108.0(5) ?
N5 C10 H10 . . 109.3 ?
N1 C10 H10 . . 109.3 ?
C9 C10 H10 . . 109.3 ?
C2 C11 H11A . . 109.5 ?
C2 C11 H11B . . 109.5 ?
H11A C11 H11B . . 109.5 ?
C2 C11 H11C . . 109.5 ?
H11A C11 H11C . . 109.5 ?
H11B C11 H11C . . 109.5 ?
C7 C12 H12A . . 109.5 ?
C7 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C7 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C10 N1 C2 C11 . . . . -173.5(6) ?
C10 N1 C2 C3 . . . . 64.0(7) ?
N1 C2 C3 C4 . . . . -46.6(8) ?
C11 C2 C3 C4 . . . . -166.3(6) ?
C2 C3 C4 O1 . . . . -164.7(6) ?
C2 C3 C4 N5 . . . . 14.2(10) ?
O1 C4 N5 C10 . . . . -174.0(6) ?
C3 C4 N5 C10 . . . . 7.1(10) ?
O1 C4 N5 C6 . . . . 8.0(10) ?
C3 C4 N5 C6 . . . . -170.9(6) ?
C4 N5 C6 C7 . . . . -121.3(7) ?
C10 N5 C6 C7 . . . . 60.5(7) ?
N5 C6 C7 C12 . . . . 66.8(7) ?
N5 C6 C7 C8 . . . . -59.3(7) ?
C6 C7 C8 C9 . . . . 56.1(8) ?
C12 C7 C8 C9 . . . . -68.5(8) ?
C7 C8 C9 C10 . . . . -52.4(9) ?
C4 N5 C10 N1 . . . . 7.8(9) ?
C6 N5 C10 N1 . . . . -174.0(5) ?
C4 N5 C10 C9 . . . . 127.3(6) ?
C6 N5 C10 C9 . . . . -54.5(7) ?
C2 N1 C10 N5 . . . . -44.8(8) ?
C2 N1 C10 C9 . . . . -165.8(6) ?
C8 C9 C10 N5 . . . . 50.0(8) ?
C8 C9 C10 N1 . . . . 170.8(6) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A Cl1 . 0.92(7) 2.36(8) 3.132(7) 142.(5) ?
N1 H1B Cl1 1_545 0.90(3) 2.22(3) 3.093(7) 166.(7) ?
C2 H2 Cl2 1_565 1.0 2.77 3.600(7) 141.2 ?
C7 H7 Cl2 2_556 1.0 2.86 3.731(6) 146.3 ?
O1 H2A Cl2 . 1.02(10) 1.76(10) 2.778(5) 176.(8) ?



#=============================================================================
#  end of cif data for "glo9508"  (compound all-cis-4a)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================

