# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_goebeld190213_0ma
_audit_block_doi                 10.5517/ccdc.csd.cc221gj4
_database_code_depnum_ccdc_archive 'CCDC 1908035'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1021/acs.orglett.9b01350 2019
loop_
_audit_author_name
_audit_author_address
'Enno Lork'
;University of Bremen
Germany
;
_audit_update_record             
;
2019-04-04 deposited with the CCDC.	2020-05-04 downloaded from the CCDC.
;
_audit_creation_date             2019-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
dgoebel@uni-bremen.de
e.lork@uni-bremen.de
nachtsheim@uni-bremen.de
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H12 N2 O2'
_chemical_formula_sum            'C12 H12 N2 O2'
_chemical_formula_weight         216.24
_chemical_melting_point          ?
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'

_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.
;
_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'
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                   19.3821(5)
_cell_length_b                   6.6585(2)
_cell_length_c                   8.0463(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1038.42(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8399
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      33.15
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.972
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6573
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1246 before and 0.0610 after correction. The Ratio of minimum to maximum transmission is 0.8805. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16938
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.184
_diffrn_reflns_theta_min         3.291
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker VENTURE area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1763
_reflns_number_total             2131
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         2131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0627P)²+0.2702P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1155
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.62054(4) 0.250000 0.66368(11) 0.01675(19) Uani 1 2 d S T P . .
H1 H 0.6465(12) 0.250000 0.563(3) 0.045(6) Uiso 1 2 d S T P . .
O2 O 0.57138(4) 0.250000 0.15987(10) 0.01558(19) Uani 1 2 d S T P . .
N1 N 0.40971(6) 0.250000 0.11315(14) 0.0210(2) Uani 1 2 d S T P . .
N2 N 0.65422(5) 0.250000 0.35623(12) 0.0140(2) Uani 1 2 d S T P . .
C1 C 0.55421(6) 0.250000 0.61545(14) 0.0117(2) Uani 1 2 d S T P . .
C2 C 0.53486(5) 0.250000 0.44661(13) 0.01007(19) Uani 1 2 d S T P . .
C3 C 0.46374(6) 0.250000 0.40758(14) 0.0114(2) Uani 1 2 d S T P . .
C4 C 0.41409(6) 0.250000 0.53278(14) 0.0126(2) Uani 1 2 d S T P . .
H4 H 0.366445 0.250000 0.505074 0.015 Uiso 1 2 calc RS T P . .
C5 C 0.43451(6) 0.250000 0.69833(15) 0.0133(2) Uani 1 2 d S T P . .
H5 H 0.400595 0.250000 0.783562 0.016 Uiso 1 2 calc RS T P . .
C6 C 0.50362(6) 0.250000 0.74019(14) 0.0133(2) Uani 1 2 d S T P . .
H6 H 0.516942 0.250000 0.853815 0.016 Uiso 1 2 calc RS T P . .
C7 C 0.43738(6) 0.250000 0.23992(15) 0.0141(2) Uani 1 2 d S T P . .
C8 C 0.58950(6) 0.250000 0.32117(13) 0.0109(2) Uani 1 2 d S T P . .
C9 C 0.63556(6) 0.250000 0.06606(16) 0.0196(3) Uani 1 2 d S T P . .
H9 H 0.6350(6) 0.130(2) -0.0013(15) 0.023 Uiso 1 1 d R . . . .
C10 C 0.69339(6) 0.250000 0.19802(14) 0.0130(2) Uani 1 2 d S T P . .
C11 C 0.73790(5) 0.43814(14) 0.18908(12) 0.02007(19) Uani 1 1 d . . . . .
H11A H 0.772719 0.434090 0.277325 0.030 Uiso 1 1 calc GR . . . .
H11B H 0.708764 0.557166 0.203493 0.030 Uiso 1 1 calc GR . . . .
H11C H 0.760850 0.444241 0.080680 0.030 Uiso 1 1 calc GR . . . .


_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 H1 0.96(3) . ?
O1 C1 1.3429(13) . ?
O2 C8 1.3445(13) . ?
O2 C9 1.4551(14) . ?
N1 C7 1.1525(16) . ?
N2 C8 1.2858(14) . ?
N2 C10 1.4822(15) . ?
C1 C2 1.4094(16) . ?
C1 C6 1.4032(15) . ?
C2 C3 1.4137(15) . ?
C2 C8 1.4629(14) . ?
C3 C4 1.3932(15) . ?
C3 C7 1.4426(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3896(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.3811(16) . ?
C6 H6 0.9500 . ?
C9 H9 0.968(14) 7_565 ?
C9 H9 0.968(14) . ?
C9 C10 1.5438(17) . ?
C10 C11 1.5227(11) . ?
C10 C11 1.5227(11) 7_565 ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

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 105.0(14) . . ?
C8 O2 C9 106.10(9) . . ?
C8 N2 C10 108.14(9) . . ?
O1 C1 C2 122.23(10) . . ?
O1 C1 C6 117.54(10) . . ?
C6 C1 C2 120.24(10) . . ?
C1 C2 C3 118.26(10) . . ?
C1 C2 C8 118.19(9) . . ?
C3 C2 C8 123.54(10) . . ?
C2 C3 C7 123.58(10) . . ?
C4 C3 C2 120.86(10) . . ?
C4 C3 C7 115.56(10) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.76(10) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.67(11) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.21(11) . . ?
C5 C6 H6 119.9 . . ?
N1 C7 C3 173.01(12) . . ?
O2 C8 C2 118.48(9) . . ?
N2 C8 O2 117.82(10) . . ?
N2 C8 C2 123.70(10) . . ?
O2 C9 H9 106.3(8) . . ?
O2 C9 H9 106.3(8) . 7_565 ?
O2 C9 C10 105.30(9) . . ?
H9 C9 H9 111.9(15) . 7_565 ?
C10 C9 H9 113.1(8) . 7_565 ?
C10 C9 H9 113.1(8) . . ?
N2 C10 C9 102.64(9) . . ?
N2 C10 C11 109.31(6) . . ?
N2 C10 C11 109.31(6) . 7_565 ?
C11 C10 C9 112.26(6) . . ?
C11 C10 C9 112.26(6) 7_565 . ?
C11 C10 C11 110.71(10) . 7_565 ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 180.000(0) . . . . ?
O1 C1 C2 C8 0.000(0) . . . . ?
O1 C1 C6 C5 180.000(0) . . . . ?
O2 C9 C10 N2 0.0 . . . . ?
O2 C9 C10 C11 117.26(7) . . . 7_565 ?
O2 C9 C10 C11 -117.26(7) . . . . ?
C1 C2 C3 C4 0.000(0) . . . . ?
C1 C2 C3 C7 180.000(0) . . . . ?
C1 C2 C8 O2 180.000(0) . . . . ?
C1 C2 C8 N2 0.000(0) . . . . ?
C2 C1 C6 C5 0.000(0) . . . . ?
C2 C3 C4 C5 0.000(0) . . . . ?
C3 C2 C8 O2 0.000(0) . . . . ?
C3 C2 C8 N2 180.0 . . . . ?
C3 C4 C5 C6 0.000(0) . . . . ?
C4 C5 C6 C1 0.000(0) . . . . ?
C6 C1 C2 C3 0.000(0) . . . . ?
C6 C1 C2 C8 180.000(0) . . . . ?
C7 C3 C4 C5 180.000(0) . . . . ?
C8 O2 C9 C10 0.0 . . . . ?
C8 N2 C10 C9 0.0 . . . . ?
C8 N2 C10 C11 119.34(7) . . . . ?
C8 N2 C10 C11 -119.34(7) . . . 7_565 ?
C8 C2 C3 C4 180.000(0) . . . . ?
C8 C2 C3 C7 0.000(0) . . . . ?
C9 O2 C8 N2 0.0 . . . . ?
C9 O2 C8 C2 180.0 . . . . ?
C10 N2 C8 O2 0.0 . . . . ?
C10 N2 C8 C2 180.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_goebeld191115_0m
_database_code_depnum_ccdc_archive 'CCDC 1970921'
loop_
_audit_author_name
_audit_author_address
'Daniel Duvinage'
;University of Bremen
Germany
;
_audit_update_record             
;
2019-12-09 deposited with the CCDC.	2020-05-04 downloaded from the CCDC.
;
_audit_creation_date             2019-11-27
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 N2 O2'
_chemical_formula_sum            'C12 H12 N2 O2'
_chemical_formula_weight         216.24
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7920(3)
_cell_length_b                   12.0885(5)
_cell_length_c                   14.1497(5)
_cell_angle_alpha                112.3500(10)
_cell_angle_beta                 93.1240(10)
_cell_angle_gamma                95.396(2)
_cell_volume                     1064.57(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8256
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.34
_cell_measurement_theta_min      2.84
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1245 before and 0.0557 after correction. The Ratio of minimum to maximum transmission is 0.9485. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26149
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.495
_diffrn_reflns_theta_min         2.836
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3460
_reflns_number_total             4419
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.521
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.073
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0904P)²+0.4348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1407
_refine_ls_wR_factor_ref         0.1545
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C29(H29A,H29B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C23(H23), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C11'(H11D,H11E,H11F), C31(H31A,H31B,H31C), C31'(H31D,
 H31E,H31F)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.6995(2) 0.53302(12) 0.09448(10) 0.0191(3) Uani 1 1 d . . . . .
H1 H 0.704446 0.569754 0.054646 0.029 Uiso 1 1 calc GR . . . .
N1 N 0.8883(3) 0.91419(15) 0.58770(13) 0.0196(4) Uani 1 1 d . . . . .
C1 C 0.7333(3) 0.61273(16) 0.19182(14) 0.0134(4) Uani 1 1 d . . . . .
O2 O 0.7687(2) 0.90427(11) 0.16310(10) 0.0153(3) Uani 1 1 d . . . . .
N2 N 0.7423(2) 0.71644(14) 0.03985(12) 0.0150(4) Uani 1 1 d . . . . .
C2 C 0.7637(3) 0.73816(16) 0.21763(13) 0.0113(4) Uani 1 1 d . . . . .
C3 C 0.8009(3) 0.81676(16) 0.32002(14) 0.0122(4) Uani 1 1 d . . . . .
H3 H 0.821496 0.901321 0.337556 0.015 Uiso 1 1 calc R . . . .
C4 C 0.8079(3) 0.77136(16) 0.39661(14) 0.0127(4) Uani 1 1 d . . . . .
C5 C 0.7777(3) 0.64656(17) 0.37094(14) 0.0144(4) Uani 1 1 d . . . . .
H5 H 0.783033 0.615837 0.423523 0.017 Uiso 1 1 calc R . . . .
C6 C 0.7404(3) 0.56862(17) 0.26980(14) 0.0157(4) Uani 1 1 d . . . . .
H6 H 0.719224 0.484183 0.252832 0.019 Uiso 1 1 calc R . . . .
C7 C 0.8523(3) 0.85244(16) 0.50289(14) 0.0142(4) Uani 1 1 d . . . . .
C8 C 0.7580(3) 0.78332(16) 0.13508(14) 0.0125(4) Uani 1 1 d . . . . .
C9 C 0.7676(3) 0.92310(16) 0.06736(14) 0.0157(4) Uani 1 1 d . . . . .
H9A H 0.895500 0.967218 0.063747 0.019 Uiso 1 1 calc R . . . .
H9B H 0.658759 0.969761 0.061311 0.019 Uiso 1 1 calc R . . . .
C10 C 0.7354(3) 0.79529(16) -0.01861(14) 0.0146(4) Uani 1 1 d . . . . .
C11 C 0.9001(3) 0.77380(17) -0.09025(15) 0.0194(4) Uani 1 1 d . . . . .
H11A H 1.029267 0.790447 -0.049902 0.029 Uiso 1 1 calc GR . . . .
H11B H 0.896452 0.827398 -0.127540 0.029 Uiso 1 1 calc GR . . . .
H11C H 0.880608 0.689751 -0.139354 0.029 Uiso 1 1 calc GR . . . .
C11' C 0.5322(3) 0.76752(18) -0.07947(15) 0.0202(4) Uani 1 1 d . . . . .
H11D H 0.510591 0.682302 -0.125861 0.030 Uiso 1 1 calc GR . . . .
H11E H 0.526604 0.817863 -0.119664 0.030 Uiso 1 1 calc GR . . . .
H11F H 0.428727 0.784540 -0.032032 0.030 Uiso 1 1 calc GR . . . .
C21 C 0.2444(3) 0.60991(16) 0.26507(14) 0.0132(4) Uani 1 1 d . . . . .
O21 O 0.2269(2) 0.51407(11) 0.29103(10) 0.0184(3) Uani 1 1 d . . . . .
H21 H 0.240221 0.537381 0.355283 0.028 Uiso 1 1 calc GR . . . .
N21 N 0.2877(3) 0.97960(16) 0.14132(13) 0.0221(4) Uani 1 1 d . . . . .
N22 N 0.2870(2) 0.66405(14) 0.48140(12) 0.0158(4) Uani 1 1 d . . . . .
C22 C 0.2858(3) 0.72925(16) 0.33957(14) 0.0117(4) Uani 1 1 d . . . . .
O22 O 0.3642(2) 0.86243(11) 0.51666(10) 0.0166(3) Uani 1 1 d . . . . .
C23 C 0.2991(3) 0.82552(16) 0.30789(14) 0.0120(4) Uani 1 1 d . . . . .
H23 H 0.326584 0.905858 0.357354 0.014 Uiso 1 1 calc R . . . .
C24 C 0.2723(3) 0.80412(17) 0.20422(14) 0.0128(4) Uani 1 1 d . . . . .
C25 C 0.2347(3) 0.68573(17) 0.13053(14) 0.0148(4) Uani 1 1 d . . . . .
H25 H 0.218485 0.671451 0.059572 0.018 Uiso 1 1 calc R . . . .
C26 C 0.2213(3) 0.59028(17) 0.16131(14) 0.0159(4) Uani 1 1 d . . . . .
H26 H 0.196099 0.510192 0.111234 0.019 Uiso 1 1 calc R . . . .
C27 C 0.2816(3) 0.90308(17) 0.17068(14) 0.0143(4) Uani 1 1 d . . . . .
C28 C 0.3106(3) 0.74856(16) 0.44795(14) 0.0124(4) Uani 1 1 d . . . . .
C29 C 0.3753(3) 0.85447(17) 0.61723(14) 0.0173(4) Uani 1 1 d . . . . .
H29A H 0.275290 0.899505 0.659325 0.021 Uiso 1 1 calc R . . . .
H29B H 0.509002 0.887705 0.654330 0.021 Uiso 1 1 calc R . . . .
C30 C 0.3322(3) 0.71818(17) 0.59451(14) 0.0157(4) Uani 1 1 d . . . . .
C31 C 0.1525(3) 0.6900(2) 0.64529(16) 0.0224(5) Uani 1 1 d . . . . .
H31A H 0.038399 0.723555 0.625948 0.034 Uiso 1 1 calc GR . . . .
H31B H 0.182800 0.725808 0.720062 0.034 Uiso 1 1 calc GR . . . .
H31C H 0.120682 0.602425 0.622477 0.034 Uiso 1 1 calc GR . . . .
C31' C 0.5137(3) 0.66787(19) 0.62301(15) 0.0200(4) Uani 1 1 d . . . . .
H31D H 0.484470 0.580244 0.600673 0.030 Uiso 1 1 calc GR . . . .
H31E H 0.546851 0.704244 0.697597 0.030 Uiso 1 1 calc GR . . . .
H31F H 0.626525 0.686789 0.589071 0.030 Uiso 1 1 calc GR . . . .


_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 H1 0.8400 . ?
O1 C1 1.339(2) . ?
N1 C7 1.144(2) . ?
C1 C2 1.410(3) . ?
C1 C6 1.397(3) . ?
O2 C8 1.355(2) . ?
O2 C9 1.456(2) . ?
N2 C8 1.273(2) . ?
N2 C10 1.483(2) . ?
C2 C3 1.391(2) . ?
C2 C8 1.465(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.389(3) . ?
C4 C5 1.403(3) . ?
C4 C7 1.445(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.375(3) . ?
C6 H6 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.547(3) . ?
C10 C11 1.525(3) . ?
C10 C11' 1.524(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?
C21 O21 1.339(2) . ?
C21 C22 1.416(3) . ?
C21 C26 1.393(3) . ?
O21 H21 0.8400 . ?
N21 C27 1.148(2) . ?
N22 C28 1.280(2) . ?
N22 C30 1.482(2) . ?
C22 C23 1.395(2) . ?
C22 C28 1.458(3) . ?
O22 C28 1.350(2) . ?
O22 C29 1.461(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.388(3) . ?
C24 C25 1.403(3) . ?
C24 C27 1.443(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.377(3) . ?
C26 H26 0.9500 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.549(3) . ?
C30 C31 1.526(3) . ?
C30 C31' 1.525(3) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C31' H31D 0.9800 . ?
C31' H31E 0.9800 . ?
C31' H31F 0.9800 . ?

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 109.5 . . ?
O1 C1 C2 122.42(16) . . ?
O1 C1 C6 118.13(16) . . ?
C6 C1 C2 119.44(17) . . ?
C8 O2 C9 105.26(13) . . ?
C8 N2 C10 107.92(15) . . ?
C1 C2 C8 118.94(16) . . ?
C3 C2 C1 119.95(16) . . ?
C3 C2 C8 121.10(16) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 C2 119.86(16) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 120.20(17) . . ?
C3 C4 C7 120.08(16) . . ?
C5 C4 C7 119.70(17) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.09(17) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.46(17) . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C4 178.23(19) . . ?
O2 C8 C2 117.16(15) . . ?
N2 C8 O2 118.57(16) . . ?
N2 C8 C2 124.26(16) . . ?
O2 C9 H9A 110.7 . . ?
O2 C9 H9B 110.7 . . ?
O2 C9 C10 105.29(14) . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
N2 C10 C9 102.63(14) . . ?
N2 C10 C11 109.93(15) . . ?
N2 C10 C11' 108.62(15) . . ?
C11 C10 C9 112.25(15) . . ?
C11' C10 C9 112.38(16) . . ?
C11' C10 C11 110.68(16) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11' H11D 109.5 . . ?
C10 C11' H11E 109.5 . . ?
C10 C11' H11F 109.5 . . ?
H11D C11' H11E 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?
O21 C21 C22 122.05(16) . . ?
O21 C21 C26 118.34(17) . . ?
C26 C21 C22 119.61(17) . . ?
C21 O21 H21 109.5 . . ?
C28 N22 C30 108.09(15) . . ?
C21 C22 C28 119.07(16) . . ?
C23 C22 C21 119.41(17) . . ?
C23 C22 C28 121.52(16) . . ?
C28 O22 C29 105.61(14) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.08(17) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 C25 120.36(17) . . ?
C23 C24 C27 120.57(17) . . ?
C25 C24 C27 119.06(17) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.83(17) . . ?
C26 C25 H25 120.1 . . ?
C21 C26 H26 119.7 . . ?
C25 C26 C21 120.69(18) . . ?
C25 C26 H26 119.7 . . ?
N21 C27 C24 178.1(2) . . ?
N22 C28 C22 123.96(17) . . ?
N22 C28 O22 118.32(16) . . ?
O22 C28 C22 117.71(16) . . ?
O22 C29 H29A 110.7 . . ?
O22 C29 H29B 110.7 . . ?
O22 C29 C30 105.16(14) . . ?
H29A C29 H29B 108.8 . . ?
C30 C29 H29A 110.7 . . ?
C30 C29 H29B 110.7 . . ?
N22 C30 C29 102.67(14) . . ?
N22 C30 C31 109.64(16) . . ?
N22 C30 C31' 108.67(15) . . ?
C31 C30 C29 112.08(16) . . ?
C31' C30 C29 112.19(17) . . ?
C31' C30 C31 111.20(16) . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C31' H31D 109.5 . . ?
C30 C31' H31E 109.5 . . ?
C30 C31' H31F 109.5 . . ?
H31D C31' H31E 109.5 . . ?
H31D C31' H31F 109.5 . . ?
H31E C31' H31F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_goebeld191114_0m
_database_code_depnum_ccdc_archive 'CCDC 1970920'
loop_
_audit_author_name
_audit_author_address
'Daniel Duvinage'
;University of Bremen
Germany
;
_audit_update_record             
;
2019-12-09 deposited with the CCDC.	2020-05-04 downloaded from the CCDC.
;
_audit_creation_date             2019-12-06
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 N2 O2'
_chemical_formula_sum            'C12 H12 N2 O2'
_chemical_formula_weight         216.24
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.9061(12)
_cell_length_b                   6.6510(6)
_cell_length_c                   13.8072(12)
_cell_angle_alpha                90
_cell_angle_beta                 110.888(3)
_cell_angle_gamma                90
_cell_volume                     1107.30(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1659
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      30.36
_cell_measurement_theta_min      3.00
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1246 before and 0.0548 after correction. The Ratio of minimum to maximum transmission is 0.9324. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27844
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.748
_diffrn_reflns_theta_min         3.158
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker PHOTON area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2146
_reflns_number_total             2600
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.358
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2600
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+0.3841P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1044
_refine_ls_wR_factor_ref         0.1109
_refine_special_details          ?
_olex2_refinement_description    
;
1. Others
 Fixed Uiso: H1(0.039) H3(0.018) H4(0.019) H6(0.023) H9A(0.024) H9B(0.024)
 H11A(0.052) H11B(0.052) H11C(0.052) H11D(0.04) H11E(0.04) H11F(0.04)
 Fixed X: H1(0.420103) H3(0.410953) H4(0.598356) H6(0.682589) H9A(0.086845)
 H9B(0.091868) H11A(0.146598) H11B(0.038166) H11C(0.147022) H11D(0.148877)
 H11E(0.0379) H11F(0.143765)
 Fixed Y: H1(0.314984) H3(0.237277) H4(0.225903) H6(0.289352) H9A(0.376689)
 H9B(0.13676) H11A(0.140358) H11B(0.121271) H11C(-0.00532) H11D(0.605326)
 H11E(0.499114) H11F(0.514514)
 Fixed Z: H1(0.214143) H3(0.529504) H4(0.634405) H6(0.37834) H9A(0.293544)
 H9B(0.280321) H11A(0.050918) H11B(0.080981) H11C(0.143307) H11D(0.183334)
 H11E(0.108618) H11F(0.074389)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.48939(7) 0.31266(16) 0.24346(7) 0.0257(2) Uani 1 1 d . . . . .
H1 H 0.420103 0.314984 0.214143 0.039 Uiso 1 1 calc GR . . . .
N1 N 0.86434(9) 0.23536(17) 0.63109(9) 0.0259(3) Uani 1 1 d . . . . .
C1 C 0.51538(10) 0.28735(18) 0.34583(9) 0.0173(3) Uani 1 1 d . . . . .
C2 C 0.43405(9) 0.27005(16) 0.39185(9) 0.0146(2) Uani 1 1 d . . . . .
N2 N 0.28381(8) 0.29623(17) 0.22614(8) 0.0221(2) Uani 1 1 d . . . . .
O2 O 0.24006(7) 0.25848(13) 0.36936(6) 0.0192(2) Uani 1 1 d . . . . .
C3 C 0.46609(10) 0.24770(16) 0.49898(9) 0.0153(2) Uani 1 1 d . . . . .
H3 H 0.410953 0.237277 0.529504 0.018 Uiso 1 1 calc R . . . .
C4 C 0.57687(10) 0.24049(17) 0.56142(9) 0.0161(2) Uani 1 1 d . . . . .
H4 H 0.598356 0.225903 0.634405 0.019 Uiso 1 1 calc R . . . .
C5 C 0.65659(9) 0.25514(17) 0.51483(9) 0.0162(3) Uani 1 1 d . . . . .
C6 C 0.62697(10) 0.27893(19) 0.40828(9) 0.0188(3) Uani 1 1 d . . . . .
H6 H 0.682589 0.289352 0.378340 0.023 Uiso 1 1 calc R . . . .
C7 C 0.77284(10) 0.24482(18) 0.57916(9) 0.0193(3) Uani 1 1 d . . . . .
C8 C 0.31697(9) 0.27606(17) 0.32446(9) 0.0162(2) Uani 1 1 d . . . . .
C9 C 0.13270(10) 0.26431(19) 0.28419(9) 0.0203(3) Uani 1 1 d . . . . .
H9A H 0.086845 0.376689 0.293544 0.024 Uiso 1 1 calc R . . . .
H9B H 0.091868 0.136760 0.280321 0.024 Uiso 1 1 calc R . . . .
C10 C 0.16076(9) 0.2952(2) 0.18516(9) 0.0196(3) Uani 1 1 d . . . . .
C11 C 0.11944(11) 0.1224(2) 0.10820(11) 0.0350(4) Uani 1 1 d . . . . .
H11A H 0.146598 0.140358 0.050918 0.052 Uiso 1 1 calc GR . . . .
H11B H 0.038166 0.121271 0.080981 0.052 Uiso 1 1 calc GR . . . .
H11C H 0.147022 -0.005320 0.143307 0.052 Uiso 1 1 calc GR . . . .
C11' C 0.11911(11) 0.4965(2) 0.13325(10) 0.0267(3) Uani 1 1 d . . . . .
H11D H 0.148877 0.605326 0.183334 0.040 Uiso 1 1 calc GR . . . .
H11E H 0.037900 0.499114 0.108618 0.040 Uiso 1 1 calc GR . . . .
H11F H 0.143765 0.514514 0.074389 0.040 Uiso 1 1 calc GR . . . .


_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 H1 0.8400 . ?
O1 C1 1.3418(14) . ?
N1 C7 1.1441(16) . ?
C1 C2 1.4122(16) . ?
C1 C6 1.3912(16) . ?
C2 C3 1.3947(16) . ?
C2 C8 1.4656(16) . ?
N2 C8 1.2766(16) . ?
N2 C10 1.4837(15) . ?
O2 C8 1.3500(14) . ?
O2 C9 1.4637(14) . ?
C3 H3 0.9500 . ?
C3 C4 1.3823(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3978(16) . ?
C5 C6 1.3909(17) . ?
C5 C7 1.4471(16) . ?
C6 H6 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5480(17) . ?
C10 C11 1.5266(18) . ?
C10 C11' 1.5230(18) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11' H11D 0.9800 . ?
C11' H11E 0.9800 . ?
C11' H11F 0.9800 . ?

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 109.5 . . ?
O1 C1 C2 122.51(11) . . ?
O1 C1 C6 118.21(10) . . ?
C6 C1 C2 119.28(11) . . ?
C1 C2 C8 118.39(10) . . ?
C3 C2 C1 119.94(11) . . ?
C3 C2 C8 121.66(10) . . ?
C8 N2 C10 108.22(10) . . ?
C8 O2 C9 105.62(9) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.98(10) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.55(10) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C7 119.11(11) . . ?
C6 C5 C4 121.66(11) . . ?
C6 C5 C7 119.23(10) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.58(10) . . ?
C5 C6 H6 120.2 . . ?
N1 C7 C5 179.02(13) . . ?
N2 C8 C2 123.84(11) . . ?
N2 C8 O2 118.35(10) . . ?
O2 C8 C2 117.81(10) . . ?
O2 C9 H9A 110.7 . . ?
O2 C9 H9B 110.7 . . ?
O2 C9 C10 105.11(9) . . ?
H9A C9 H9B 108.8 . . ?
C10 C9 H9A 110.7 . . ?
C10 C9 H9B 110.7 . . ?
N2 C10 C9 102.67(9) . . ?
N2 C10 C11 109.25(10) . . ?
N2 C10 C11' 109.01(10) . . ?
C11 C10 C9 112.40(11) . . ?
C11' C10 C9 112.21(10) . . ?
C11' C10 C11 110.92(11) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C11' H11D 109.5 . . ?
C10 C11' H11E 109.5 . . ?
C10 C11' H11F 109.5 . . ?
H11D C11' H11E 109.5 . . ?
H11D C11' H11F 109.5 . . ?
H11E C11' H11F 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
