# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ada121
_database_code_depnum_ccdc_archive 'CCDC 1906861'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2019-04-01 deposited with the CCDC.	2019-11-18 downloaded from the CCDC.
;
_audit_creation_date             2019-02-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H20 Co N4 O6, 2(N O3)'
_chemical_formula_sum            'C20 H20 Co N6 O12'
_chemical_formula_weight         595.35
_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 0.0137 0.0067 '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'
Co Co -0.6630 2.9050 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0137 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0387 0.0241 '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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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                   7.6304(5)
_cell_length_b                   17.6827(13)
_cell_length_c                   17.7371(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2393.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7016
_cell_measurement_temperature    100
_cell_measurement_theta_max      60.403
_cell_measurement_theta_min      4.338
_shelx_estimated_absorpt_T_max   0.810
_shelx_estimated_absorpt_T_min   0.644
_exptl_absorpt_coefficient_mu    4.386
_exptl_absorpt_correction_T_max  0.3107
_exptl_absorpt_correction_T_min  0.1768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1380 before and 0.0909 after correction. The Ratio of minimum to maximum transmission is 0.5690. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light purple'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    purple
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1220
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1211
_diffrn_reflns_av_unetI/netI     0.0762
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20193
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.790
_diffrn_reflns_theta_min         4.337
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1718
_reflns_number_total             2735
_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       
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_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         0.363
_refine_diff_density_min         -0.512
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       0.00032(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2735
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1301
_refine_ls_R_factor_gt           0.0730
_refine_ls_restrained_S_all      1.111
_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)+(0.0407P)²+7.3908P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1376
_refine_ls_wR_factor_ref         0.1607
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), N2(H2C), C3(H3), C5(H5), C7(H7), C8(H8), C10(H10)
;
_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
Co1 Co 1.000000 0.500000 0.500000 0.0235(2) Uani 1 2 d S T P . .
C1 C 0.9328(6) 0.5428(3) 0.3316(2) 0.0259(10) Uani 1 1 d . . . . .
O1 O 0.9387(4) 0.49411(18) 0.38419(16) 0.0271(7) Uani 1 1 d . . . . .
N1 N 0.9209(5) 0.6181(2) 0.34889(19) 0.0249(8) Uani 1 1 d . . . . .
H1 H 0.917761 0.630907 0.396803 0.030 Uiso 1 1 calc R . . . .
C2 C 0.9363(7) 0.5252(3) 0.2539(3) 0.0341(12) Uani 1 1 d . . . . .
H2 H 0.941777 0.473892 0.238192 0.041 Uiso 1 1 calc R . . . .
O2 O 0.7482(4) 0.47150(18) 0.52712(17) 0.0290(7) Uani 1 1 d . . . . .
H2A H 0.689737 0.454241 0.487569 0.043 Uiso 1 1 d GR . . . .
H2B H 0.689614 0.510935 0.544585 0.043 Uiso 1 1 d GR . . . .
N2 N 0.9842(5) 0.8418(2) 0.12101(19) 0.0239(8) Uani 1 1 d . . . . .
H2C H 1.028643 0.886397 0.131743 0.029 Uiso 1 1 calc R . . . .
C3 C 0.9317(7) 0.5817(3) 0.2011(3) 0.0324(11) Uani 1 1 d . . . . .
H3 H 0.936321 0.568574 0.149218 0.039 Uiso 1 1 calc R . . . .
O3 O 0.9286(4) 0.88428(17) 0.00219(16) 0.0272(7) Uani 1 1 d . . . . .
C4 C 0.9204(6) 0.6586(3) 0.2213(2) 0.0252(10) Uani 1 1 d . . . . .
C5 C 0.9138(6) 0.6741(3) 0.2967(2) 0.0257(10) Uani 1 1 d . . . . .
H5 H 0.903910 0.725105 0.312918 0.031 Uiso 1 1 calc R . . . .
C6 C 0.9165(6) 0.7188(3) 0.1633(2) 0.0254(10) Uani 1 1 d . . . . .
C7 C 0.8437(6) 0.7050(3) 0.0907(2) 0.0291(11) Uani 1 1 d . . . . .
H7 H 0.793216 0.657070 0.079894 0.035 Uiso 1 1 calc R . . . .
C8 C 0.8455(6) 0.7595(3) 0.0364(3) 0.0279(11) Uani 1 1 d . . . . .
H8 H 0.796330 0.749136 -0.011741 0.033 Uiso 1 1 calc R . . . .
C9 C 0.9195(6) 0.8312(3) 0.0508(2) 0.0256(10) Uani 1 1 d . . . . .
C10 C 0.9855(6) 0.7886(3) 0.1759(2) 0.0256(10) Uani 1 1 d . . . . .
H10 H 1.035127 0.800156 0.223696 0.031 Uiso 1 1 calc R . . . .
N3 N 0.5114(5) 0.3771(2) 0.3803(2) 0.0308(9) Uani 1 1 d . . . . .
O4 O 0.4991(5) 0.4296(2) 0.4283(2) 0.0548(12) Uani 1 1 d . . . . .
O5 O 0.3871(4) 0.3651(2) 0.33685(18) 0.0370(9) Uani 1 1 d . . . . .
O6 O 0.6476(5) 0.3395(2) 0.3780(2) 0.0421(9) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Co1 0.0281(5) 0.0214(4) 0.0211(4) 0.0008(4) 0.0004(4) 0.0002(4)
C1 0.025(2) 0.023(3) 0.030(2) 0.0015(19) -0.001(2) 0.000(2)
O1 0.0359(17) 0.0225(17) 0.0229(15) -0.0011(13) 0.0003(13) 0.0025(15)
N1 0.032(2) 0.025(2) 0.0179(18) -0.0001(15) -0.0003(16) 0.0034(18)
C2 0.052(3) 0.022(2) 0.028(3) -0.002(2) -0.004(2) 0.001(2)
O2 0.0317(18) 0.0263(18) 0.0289(16) -0.0014(14) 0.0018(14) 0.0003(15)
N2 0.028(2) 0.0198(19) 0.0241(19) 0.0006(14) -0.0008(17) -0.0036(17)
C3 0.045(3) 0.028(3) 0.023(2) -0.003(2) -0.005(2) 0.000(2)
O3 0.0362(17) 0.0236(16) 0.0217(15) 0.0019(14) 0.0001(14) 0.0002(14)
C4 0.026(2) 0.024(3) 0.025(2) 0.0019(18) 0.001(2) 0.000(2)
C5 0.027(3) 0.021(2) 0.029(2) -0.0006(19) 0.001(2) 0.000(2)
C6 0.023(2) 0.028(3) 0.025(2) 0.0011(19) 0.0012(19) 0.001(2)
C7 0.035(3) 0.023(3) 0.030(2) -0.003(2) -0.003(2) -0.005(2)
C8 0.034(3) 0.025(3) 0.025(2) -0.0018(19) -0.007(2) -0.004(2)
C9 0.024(2) 0.030(3) 0.023(2) -0.0010(19) 0.0011(19) -0.001(2)
C10 0.027(2) 0.027(2) 0.022(2) 0.0018(18) 0.000(2) -0.003(2)
N3 0.029(2) 0.030(2) 0.034(2) -0.0016(17) 0.0027(19) -0.001(2)
O4 0.037(2) 0.061(3) 0.066(3) -0.039(2) -0.007(2) 0.015(2)
O5 0.034(2) 0.041(2) 0.0356(19) 0.0011(16) -0.0020(16) -0.0075(17)
O6 0.034(2) 0.039(2) 0.053(2) -0.0070(18) 0.0010(18) 0.0076(18)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O1 2.109(3) 5_766 ?
Co1 O1 2.109(3) . ?
Co1 O2 2.044(3) . ?
Co1 O2 2.044(3) 5_766 ?
Co1 O3 2.118(3) 3_745 ?
Co1 O3 2.118(3) 7_576 ?
C1 O1 1.270(5) . ?
C1 N1 1.369(6) . ?
C1 C2 1.414(7) . ?
N1 H1 0.8800 . ?
N1 C5 1.357(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.369(7) . ?
O2 H2A 0.8855 . ?
O2 H2B 0.8844 . ?
N2 H2C 0.8800 . ?
N2 C9 1.352(6) . ?
N2 C10 1.354(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.408(7) . ?
O3 C9 1.278(5) . ?
C4 C5 1.366(6) . ?
C4 C6 1.481(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.425(6) . ?
C6 C10 1.361(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.362(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.411(7) . ?
C10 H10 0.9500 . ?
N3 O4 1.263(5) . ?
N3 O5 1.241(5) . ?
N3 O6 1.235(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Co1 O1 180.0 5_766 . ?
O1 Co1 O3 90.49(12) 5_766 3_745 ?
O1 Co1 O3 89.51(12) . 3_745 ?
O1 Co1 O3 90.49(12) . 7_576 ?
O1 Co1 O3 89.51(12) 5_766 7_576 ?
O2 Co1 O1 90.48(12) . . ?
O2 Co1 O1 89.52(12) . 5_766 ?
O2 Co1 O1 90.48(12) 5_766 5_766 ?
O2 Co1 O1 89.52(12) 5_766 . ?
O2 Co1 O2 180.0 . 5_766 ?
O2 Co1 O3 90.45(12) . 3_745 ?
O2 Co1 O3 90.45(12) 5_766 7_576 ?
O2 Co1 O3 89.55(12) 5_766 3_745 ?
O2 Co1 O3 89.55(12) . 7_576 ?
O3 Co1 O3 180.0 7_576 3_745 ?
O1 C1 N1 119.8(4) . . ?
O1 C1 C2 124.5(4) . . ?
N1 C1 C2 115.7(4) . . ?
C1 O1 Co1 133.6(3) . . ?
C1 N1 H1 118.0 . . ?
C5 N1 C1 124.1(4) . . ?
C5 N1 H1 118.0 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(4) . . ?
C3 C2 H2 119.8 . . ?
Co1 O2 H2A 111.8 . . ?
Co1 O2 H2B 111.3 . . ?
H2A O2 H2B 107.1 . . ?
C9 N2 H2C 117.7 . . ?
C9 N2 C10 124.7(4) . . ?
C10 N2 H2C 117.7 . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.1(4) . . ?
C4 C3 H3 118.9 . . ?
C9 O3 Co1 137.5(3) . 3_755 ?
C3 C4 C6 121.3(4) . . ?
C5 C4 C3 116.4(4) . . ?
C5 C4 C6 122.3(4) . . ?
N1 C5 C4 121.3(4) . . ?
N1 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C7 C6 C4 120.8(4) . . ?
C10 C6 C4 122.1(4) . . ?
C10 C6 C7 117.1(4) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 120.9(4) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.7(4) . . ?
C9 C8 H8 119.6 . . ?
N2 C9 C8 116.0(4) . . ?
O3 C9 N2 120.0(4) . . ?
O3 C9 C8 124.0(4) . . ?
N2 C10 C6 120.6(4) . . ?
N2 C10 H10 119.7 . . ?
C6 C10 H10 119.7 . . ?
O5 N3 O4 119.2(4) . . ?
O6 N3 O4 118.7(4) . . ?
O6 N3 O5 122.1(4) . . ?

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
_geom_hbond_publ_flag
N1 H1 O3 0.88 1.89 2.720(4) 156.5 7_576 yes
C2 H2 O5 0.95 2.38 3.278(6) 158.4 6_656 yes
O2 H2A O4 0.89 1.85 2.690(5) 158.3 . yes
O2 H2B O4 0.88 1.85 2.692(5) 159.1 5_666 yes
N2 H2C O1 0.88 1.94 2.759(5) 153.9 3_755 yes
C5 H5 O6 0.95 2.36 3.295(6) 167.0 8_765 yes
C8 H8 O6 0.95 2.54 3.309(6) 138.0 2_664 yes
C10 H10 O5 0.95 2.39 3.304(6) 162.2 8_765 yes

_shelx_res_file                  
;
TITL ada121_a.res in Pbca
    ada121.res
    created by SHELXL-2018/3 at 08:45:26 on 01-Feb-2019
REM Old TITL ada121 in Pbca
REM SHELXT solution in Pbca
REM R1 0.146, Rweak 0.013, Alpha 0.033, Orientation as input
REM Formula found by SHELXT: C22 N4 O12 Co
CELL 1.34139 7.6304 17.6827 17.7371 90 90 90
ZERR 4 0.0005 0.0013 0.0011 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Co N O
DISP C 0.0137 0.0067 57.1
DISP Co -0.663 2.905 22108.7
DISP H -0 0 0.648
DISP N 0.0241 0.0137 109.9
DISP O 0.0387 0.0241 193.4
UNIT 80 80 4 24 48
EQIV $1 2-X,0.5+Y,0.5-Z
EQIV $2 +X,1.5-Y,0.5+Z
EQIV $3 0.5+X,+Y,0.5-Z
EQIV $4 1-X,1-Y,1-Z
EQIV $5 1.5-X,0.5+Y,+Z
EQIV $6 1.5-X,1-Y,-0.5+Z

L.S. 14
PLAN  11
SIZE 0.05 0.07 0.11
TEMP -173.15
HTAB N1 O3_$2
HTAB C2 O5_$3
HTAB O2 O4
HTAB O2 O4_$4
HTAB N2 O1_$1
HTAB C5 O6_$5
HTAB C8 O6_$6
HTAB C10 O5_$5
HTAB
BOND $H
list 4
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\ada121.hkl">
REM </olex2.extras>

WGHT    0.040700    7.390800
EXTI    0.000317
FVAR       0.25231
CO1   3    1.000000    0.500000    0.500000    10.50000    0.02807    0.02140 =
         0.02107    0.00078    0.00042    0.00017
C1    1    0.932801    0.542792    0.331626    11.00000    0.02480    0.02256 =
         0.03025    0.00154   -0.00099   -0.00005
O1    5    0.938665    0.494108    0.384188    11.00000    0.03591    0.02254 =
         0.02289   -0.00107    0.00029    0.00249
N1    4    0.920932    0.618053    0.348892    11.00000    0.03213    0.02475 =
         0.01793   -0.00012   -0.00034    0.00341
AFIX  43
H1    2    0.917761    0.630907    0.396803    11.00000   -1.20000
AFIX   0
C2    1    0.936260    0.525198    0.253902    11.00000    0.05234    0.02216 =
         0.02772   -0.00191   -0.00357    0.00115
AFIX  43
H2    2    0.941777    0.473892    0.238192    11.00000   -1.20000
AFIX   0
O2    5    0.748190    0.471496    0.527120    11.00000    0.03166    0.02632 =
         0.02893   -0.00139    0.00180    0.00035
AFIX   7
H2A   2    0.689737    0.454241    0.487569    11.00000   -1.50000
H2B   2    0.689614    0.510935    0.544585    11.00000   -1.50000
AFIX   0
N2    4    0.984213    0.841752    0.121010    11.00000    0.02793    0.01979 =
         0.02411    0.00058   -0.00077   -0.00362
AFIX  43
H2C   2    1.028643    0.886397    0.131743    11.00000   -1.20000
AFIX   0
C3    1    0.931705    0.581673    0.201124    11.00000    0.04538    0.02837 =
         0.02334   -0.00280   -0.00471    0.00016
AFIX  43
H3    2    0.936321    0.568574    0.149218    11.00000   -1.20000
AFIX   0
O3    5    0.928623    0.884278    0.002191    11.00000    0.03619    0.02361 =
         0.02171    0.00191    0.00007    0.00017
C4    1    0.920397    0.658552    0.221297    11.00000    0.02571    0.02443 =
         0.02546    0.00195    0.00088   -0.00041
C5    1    0.913752    0.674077    0.296704    11.00000    0.02748    0.02094 =
         0.02870   -0.00056    0.00126   -0.00034
AFIX  43
H5    2    0.903910    0.725105    0.312918    11.00000   -1.20000
AFIX   0
C6    1    0.916491    0.718803    0.163332    11.00000    0.02301    0.02775 =
         0.02541    0.00106    0.00115    0.00126
C7    1    0.843703    0.704978    0.090657    11.00000    0.03483    0.02291 =
         0.02967   -0.00277   -0.00264   -0.00505
AFIX  43
H7    2    0.793216    0.657070    0.079894    11.00000   -1.20000
AFIX   0
C8    1    0.845476    0.759489    0.036375    11.00000    0.03374    0.02452 =
         0.02530   -0.00178   -0.00679   -0.00351
AFIX  43
H8    2    0.796330    0.749136   -0.011741    11.00000   -1.20000
AFIX   0
C9    1    0.919515    0.831153    0.050849    11.00000    0.02386    0.03005 =
         0.02287   -0.00101    0.00107   -0.00079
C10   1    0.985545    0.788612    0.175933    11.00000    0.02702    0.02742 =
         0.02226    0.00184    0.00017   -0.00307
AFIX  43
H10   2    1.035127    0.800156    0.223696    11.00000   -1.20000
AFIX   0

N3    4    0.511400    0.377126    0.380302    11.00000    0.02857    0.02990 =
         0.03401   -0.00157    0.00274   -0.00063
O4    5    0.499123    0.429616    0.428285    11.00000    0.03664    0.06121 =
         0.06644   -0.03930   -0.00718    0.01482
O5    5    0.387082    0.365082    0.336850    11.00000    0.03430    0.04101 =
         0.03563    0.00111   -0.00197   -0.00750
O6    5    0.647634    0.339485    0.378042    11.00000    0.03362    0.03932 =
         0.05348   -0.00701    0.00099    0.00765
HKLF 4




REM  ada121_a.res in Pbca
REM wR2 = 0.160716, GooF = S = 1.11134, Restrained GooF = 1.11134 for all data
REM R1 = 0.073007 for 1718 Fo > 4sig(Fo) and 0.130107 for all 2735 data
REM 180 parameters refined using 0 restraints

END

WGHT      0.0407      7.3919

REM Instructions for potential hydrogen bonds
HTAB N1 O3_$2
HTAB C2 O5_$3
HTAB O2 O4
HTAB O2 O4_$4
HTAB N2 O1_$1
HTAB C5 O6_$5
HTAB C8 O6_$6
HTAB C10 O5_$5

REM Highest difference peak  0.363,  deepest hole -0.512,  1-sigma level  0.094
Q1    1   0.8151  0.5006  0.5081  11.00000  0.05    0.36
Q2    1   0.8346  0.4377  0.5177  11.00000  0.05    0.33
Q3    1   1.0886  0.5376  0.5163  11.00000  0.05    0.33
Q4    1   1.0972  0.9044  0.0584  11.00000  0.05    0.33
Q5    1   0.8363  0.9240  0.0195  11.00000  0.05    0.32
Q6    1   1.0123  0.7376  0.1594  11.00000  0.05    0.31
Q7    1   1.0066  0.5798  0.3406  11.00000  0.05    0.31
Q8    1   1.0521  0.4982  0.3963  11.00000  0.05    0.30
Q9    1   0.6211  0.4564  0.4538  11.00000  0.05    0.30
Q10   1   0.5097  0.3294  0.3166  11.00000  0.05    0.30
Q11   1   0.5791  0.4192  0.5038  11.00000  0.05    0.29
;
_shelx_res_checksum              50739
_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_jw1184
_database_code_depnum_ccdc_archive 'CCDC 1906863'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2019-04-01 deposited with the CCDC.	2019-11-18 downloaded from the CCDC.
;
_audit_creation_date             2019-02-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 N2 O2, 2(H2 O)'
_chemical_formula_sum            'C10 H12 N2 O4'
_chemical_formula_weight         224.22
_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 0.0181 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'

_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/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                   8.9683(15)
_cell_length_b                   3.8091(7)
_cell_length_c                   14.749(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.476(13)
_cell_angle_gamma                90
_cell_volume                     503.68(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1383
_cell_measurement_temperature    100
_cell_measurement_theta_max      66.763
_cell_measurement_theta_min      5.842
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.891
_exptl_absorpt_coefficient_mu    0.980
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.5322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1046 before and 0.0608 after correction. The Ratio of minimum to maximum transmission is 0.7069. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light Colorless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker microstar diffractometer equipped with a Platinum 135 CCD Detector,
a Helios optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 512 x 512 pixel mode.
The initial unit cell parameters were determined by a least-squares fit
of the angular setting of strong reflections, collected by a 110.0 degree
scan in 110 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4085
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.687
_diffrn_reflns_theta_min         5.709
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker Platinum 135 CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Bruker Microstar/FR591 generator'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                606
_reflns_number_total             915
_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       
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_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         0.360
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         915
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1054
_refine_ls_R_factor_gt           0.0696
_refine_ls_restrained_S_all      1.100
_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)+(0.1637P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2046
_refine_ls_wR_factor_ref         0.2481
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O2-H2A = O2-H2B
 0.85 with sigma of 0.02
 O2-H2A \\sim O2-H2B
 with sigma of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5)
;
_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 0.5000(3) 0.2027(7) 0.39250(18) 0.0338(8) Uani 1 1 d . . . . .
N1 N 0.6852(4) 0.2003(7) 0.5007(2) 0.0288(8) Uani 1 1 d . . . . .
H1 H 0.631(5) 0.097(12) 0.534(3) 0.035 Uiso 1 1 d R . . . .
C1 C 0.6316(4) 0.2870(9) 0.4164(2) 0.0285(9) Uani 1 1 d . . . . .
C2 C 0.7325(4) 0.4735(9) 0.3614(3) 0.0293(9) Uani 1 1 d . . . . .
H2 H 0.701826 0.544325 0.302059 0.035 Uiso 1 1 calc R . . . .
C3 C 0.8743(4) 0.5530(9) 0.3932(2) 0.0285(9) Uani 1 1 d . . . . .
H3 H 0.940601 0.674850 0.355043 0.034 Uiso 1 1 calc R . . . .
C4 C 0.9232(4) 0.4548(9) 0.4826(2) 0.0280(9) Uani 1 1 d . . . . .
C5 C 0.8248(4) 0.2771(9) 0.5330(2) 0.0271(9) Uani 1 1 d . . . . .
H5 H 0.853730 0.203867 0.592404 0.033 Uiso 1 1 calc R . . . .
O2 O 0.3621(3) 0.4869(9) 0.2406(2) 0.0520(10) Uani 1 1 d D . . . .
H2A H 0.397(5) 0.430(14) 0.2937(16) 0.078 Uiso 1 1 d DR . . . .
H2B H 0.305(4) 0.665(7) 0.251(4) 0.078 Uiso 1 1 d DR . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0263(15) 0.0398(14) 0.0350(15) -0.0002(11) -0.0034(11) -0.0023(11)
N1 0.0294(18) 0.0302(15) 0.0268(17) -0.0033(12) 0.0005(13) 0.0000(12)
C1 0.0251(19) 0.0297(17) 0.0307(19) -0.0041(14) 0.0020(15) 0.0003(14)
C2 0.0291(19) 0.0307(17) 0.0280(17) -0.0015(14) -0.0005(14) -0.0018(14)
C3 0.0276(19) 0.0301(17) 0.0280(19) -0.0019(14) 0.0036(15) -0.0012(13)
C4 0.027(2) 0.0269(15) 0.0304(19) -0.0047(14) -0.0014(15) 0.0024(13)
C5 0.0220(18) 0.0306(17) 0.0287(19) -0.0016(14) -0.0002(14) -0.0006(13)
O2 0.050(2) 0.073(2) 0.0325(16) -0.0040(16) -0.0066(14) 0.0095(17)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.264(4) . ?
N1 H1 0.80(5) . ?
N1 C1 1.363(5) . ?
N1 C5 1.359(4) . ?
C1 C2 1.421(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.429(5) . ?
C4 C4 1.497(6) 3_766 ?
C4 C5 1.350(5) . ?
C5 H5 0.9500 . ?
O2 H2A 0.866(13) . ?
O2 H2B 0.866(13) . ?

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 N1 H1 118(3) . . ?
C5 N1 H1 117(3) . . ?
C5 N1 C1 124.6(3) . . ?
O1 C1 N1 119.9(4) . . ?
O1 C1 C2 124.9(3) . . ?
N1 C1 C2 115.3(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C4 120.9(4) . 3_766 ?
C5 C4 C3 116.7(3) . . ?
C5 C4 C4 122.4(4) . 3_766 ?
N1 C5 H5 119.2 . . ?
C4 C5 N1 121.7(3) . . ?
C4 C5 H5 119.2 . . ?
H2A O2 H2B 104(5) . . ?

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
_geom_hbond_publ_flag
N1 H1 O1 0.80(5) 1.98(5) 2.781(4) 174(4) 3_656 yes
O2 H2A O1 0.866(13) 1.91(2) 2.753(4) 164(5) . yes
O2 H2B O2 0.866(13) 1.941(17) 2.788(5) 166(4) 2 yes

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 -179.8(3) . . . . ?
N1 C1 C2 C3 0.7(5) . . . . ?
C1 N1 C5 C4 0.9(5) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C3 C4 C4 -179.2(4) . . . 3_766 ?
C2 C3 C4 C5 1.1(5) . . . . ?
C3 C4 C5 N1 -1.0(5) . . . . ?
C4 C4 C5 N1 179.3(4) 3_766 . . . ?
C5 N1 C1 O1 179.8(3) . . . . ?
C5 N1 C1 C2 -0.7(5) . . . . ?

_shelx_res_file                  
;
TITL jw1184_a.res in P2(1)/n
    jw1184.res
    created by SHELXL-2018/3 at 08:41:05 on 01-Feb-2019
REM Old TITL jw1184 in P2(1)/n
REM SHELXT solution in P2(1)/n
REM R1 0.164, Rweak 0.004, Alpha 0.023, Orientation as input
REM Formula found by SHELXT: C5 N2 O
CELL 1.54178 8.9683 3.8091 14.7492 90 91.476 90
ZERR 2 0.0015 0.0007 0.0029 0 0.013 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 20 24 4 8
EQIV $1 1-X,-Y,1-Z
EQIV $2 0.5-X,0.5+Y,0.5-Z
DFIX 0.85 O2 H2a O2 H2b
SADI 0.001 O2 H2a O2 H2b

L.S. 30
PLAN  10
SIZE 0.03 0.03 0.12
TEMP -173
HTAB N1 O1_$1
HTAB O2 O2_$2
HTAB O2 O1
BOND $H
list 4
MORE -1
HTAB
CONF
WPDB
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\jw1184.hkl">
REM </olex2.extras>

WGHT    0.163700
FVAR       1.35599
O1    4    0.499989    0.202691    0.392498    11.00000    0.02626    0.03979 =
         0.03504   -0.00021   -0.00340   -0.00230
N1    3    0.685200    0.200336    0.500701    11.00000    0.02939    0.03016 =
         0.02682   -0.00332    0.00051    0.00001
H1    2    0.631294    0.096872    0.534256    11.00000   -1.20000
C1    1    0.631555    0.287026    0.416377    11.00000    0.02514    0.02968 =
         0.03065   -0.00409    0.00203    0.00034
C2    1    0.732506    0.473545    0.361419    11.00000    0.02911    0.03066 =
         0.02796   -0.00146   -0.00045   -0.00180
AFIX  43
H2    2    0.701826    0.544325    0.302059    11.00000   -1.20000
AFIX   0
C3    1    0.874308    0.552964    0.393171    11.00000    0.02764    0.03012 =
         0.02801   -0.00194    0.00363   -0.00119
AFIX  43
H3    2    0.940601    0.674850    0.355043    11.00000   -1.20000
AFIX   0
C4    1    0.923216    0.454751    0.482624    11.00000    0.02672    0.02693 =
         0.03037   -0.00475   -0.00140    0.00242
C5    1    0.824752    0.277087    0.532952    11.00000    0.02205    0.03059 =
         0.02871   -0.00156   -0.00018   -0.00058
AFIX  43
H5    2    0.853730    0.203867    0.592404    11.00000   -1.20000
AFIX   0

O2    4    0.362067    0.486851    0.240571    11.00000    0.05042    0.07258 =
         0.03251   -0.00398   -0.00665    0.00945
H2A   2    0.397396    0.429573    0.293728    11.00000   -1.50000
H2B   2    0.304627    0.664549    0.250721    11.00000   -1.50000
HKLF 4




REM  jw1184_a.res in P2(1)/n
REM wR2 = 0.248099, GooF = S = 1.10104, Restrained GooF = 1.09983 for all data
REM R1 = 0.069607 for 606 Fo > 4sig(Fo) and 0.105409 for all 915 data
REM 82 parameters refined using 3 restraints

END

WGHT      0.1636      0.0000

REM Instructions for potential hydrogen bonds
HTAB N1 O1_$1
EQIV $4 x+1/2, -y+1/2, z+1/2
HTAB C5 O2_$4
HTAB O2 O1
HTAB O2 O2_$2

REM Highest difference peak  0.360,  deepest hole -0.337,  1-sigma level  0.095
Q1    1   0.4187  0.3211  0.4640  11.00000  0.05    0.36
Q2    1   0.3261  0.9844  0.2973  11.00000  0.05    0.34
Q3    1   0.5725  0.2990  0.5580  11.00000  0.05    0.34
Q4    1   0.9021 -0.2574  0.6021  11.00000  0.05    0.32
Q5    1   0.7655 -0.2042  0.4759  11.00000  0.05    0.28
Q6    1   0.5019  0.3993  0.5272  11.00000  0.05    0.27
Q7    1   0.3841  0.9853  0.1823  11.00000  0.05    0.27
Q8    1   0.5262  0.3463  0.5363  11.00000  0.05    0.27
Q9    1   0.5000  0.0000  0.5000  10.50000  0.05    0.27
Q10   1   0.9183 -0.0160  0.5202  11.00000  0.05    0.26
;
_shelx_res_checksum              84931
_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_ada155
_database_code_depnum_ccdc_archive 'CCDC 1906862'
loop_
_audit_author_name
_audit_author_address
'Thierry Maris'
;University of Montreal
Canada
;
_audit_update_record             
;
2019-04-01 deposited with the CCDC.	2019-11-18 downloaded from the CCDC.
;
_audit_creation_date             2018-08-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 N2 O2'
_chemical_formula_sum            'C10 H8 N2 O2'
_chemical_formula_weight         188.18
_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 0.0137 0.0070 '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 0.0241 0.0136 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0250 '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/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                   6.9152(3)
_cell_length_b                   18.3958(8)
_cell_length_c                   7.2525(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.199(2)
_cell_angle_gamma                90
_cell_volume                     834.80(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7880
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.672
_cell_measurement_theta_min      4.183
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.946
_exptl_absorpt_coefficient_mu    0.567
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5567
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1252 before and 0.0661 after correction. The Ratio of minimum to maximum transmission is 0.7404. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_recrystallization_method 'crystallized from DMSO/EtOH'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_exptl_special_details           
;
X-ray crystallographic data for I were collected from a single crystal
sample, which was mounted on a loop fiber. Data were collected using
a Bruker Venture diffractometer equipped with a Photon 100 CMOS Detector,
a Helios MX optics and a Kappa goniometer. The crystal-to-detector distance 
was 4.0 cm, and the data collection was carried out in 1024 x 1024 pixel mode.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            12285
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.678
_diffrn_reflns_theta_min         4.182
_diffrn_ambient_temperature      150
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1637
_reflns_number_total             1912
_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       
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_computing_data_collection       
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction        
'SAINT (2013) V8.38A; Integration Software for Single Crystal Data. Bruker AXS Inc., Madison, WI 53719-1173.'
_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         0.251
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         1912
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.056
_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)+(0.0744P)²+0.2631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1289
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.75859(17) 0.61326(5) 0.39528(15) 0.0311(3) Uani 1 1 d . . . . .
O2 O 0.64085(18) 0.09560(5) 0.56741(14) 0.0325(3) Uani 1 1 d . . . . .
N1 N 0.76991(18) 0.51520(6) 0.58970(16) 0.0252(3) Uani 1 1 d . . . . .
H1 H 0.804(3) 0.5481(10) 0.699(3) 0.044(5) Uiso 1 1 d . . . . .
N2 N 0.69518(19) 0.19162(6) 0.39910(17) 0.0264(3) Uani 1 1 d . . . . .
H2 H 0.707(3) 0.1566(10) 0.306(3) 0.041(5) Uiso 1 1 d . . . . .
C1 C 0.7456(2) 0.54542(7) 0.40831(19) 0.0246(3) Uani 1 1 d . . . . .
C2 C 0.7038(2) 0.49473(7) 0.2465(2) 0.0277(3) Uani 1 1 d . . . . .
H2A H 0.692(3) 0.5152(9) 0.117(3) 0.040(5) Uiso 1 1 d . . . . .
C3 C 0.6825(2) 0.42268(7) 0.2738(2) 0.0277(3) Uani 1 1 d . . . . .
H3 H 0.649(3) 0.3909(9) 0.155(3) 0.037(4) Uiso 1 1 d . . . . .
C4 C 0.7074(2) 0.39367(7) 0.46484(19) 0.0238(3) Uani 1 1 d . . . . .
C5 C 0.7546(2) 0.44299(7) 0.61903(19) 0.0244(3) Uani 1 1 d . . . . .
H5 H 0.786(3) 0.4302(9) 0.759(3) 0.029(4) Uiso 1 1 d . . . . .
C6 C 0.6903(2) 0.31532(7) 0.49707(19) 0.0239(3) Uani 1 1 d . . . . .
C7 C 0.6545(2) 0.28805(7) 0.6644(2) 0.0263(3) Uani 1 1 d . . . . .
H7 H 0.640(3) 0.3218(9) 0.765(3) 0.038(4) Uiso 1 1 d . . . . .
C8 C 0.6428(2) 0.21563(7) 0.69556(19) 0.0267(3) Uani 1 1 d . . . . .
H8 H 0.619(3) 0.1964(9) 0.814(3) 0.035(4) Uiso 1 1 d . . . . .
C9 C 0.6591(2) 0.16309(7) 0.55656(19) 0.0256(3) Uani 1 1 d . . . . .
C10 C 0.7113(2) 0.26406(7) 0.37018(19) 0.0252(3) Uani 1 1 d . . . . .
H10 H 0.743(3) 0.2754(8) 0.251(3) 0.031(4) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0487(6) 0.0173(5) 0.0304(5) 0.0024(4) 0.0200(5) 0.0004(4)
O2 0.0526(7) 0.0166(5) 0.0261(5) 0.0014(3) 0.0145(5) -0.0009(4)
N1 0.0349(6) 0.0172(6) 0.0219(6) 0.0001(4) 0.0106(5) 0.0007(4)
N2 0.0386(6) 0.0169(6) 0.0236(6) -0.0006(4) 0.0132(5) 0.0009(4)
C1 0.0303(7) 0.0187(6) 0.0241(6) 0.0034(5) 0.0108(5) 0.0005(5)
C2 0.0380(7) 0.0222(7) 0.0213(6) 0.0026(5) 0.0111(5) -0.0007(5)
C3 0.0380(7) 0.0218(7) 0.0215(6) -0.0018(5) 0.0110(6) -0.0019(5)
C4 0.0299(6) 0.0176(6) 0.0225(6) 0.0007(5) 0.0099(5) 0.0008(5)
C5 0.0326(7) 0.0181(6) 0.0212(6) 0.0021(5) 0.0102(5) 0.0014(5)
C6 0.0299(6) 0.0174(6) 0.0217(6) 0.0011(5) 0.0085(5) 0.0012(5)
C7 0.0343(7) 0.0211(7) 0.0226(6) 0.0001(5) 0.0112(5) 0.0023(5)
C8 0.0365(7) 0.0211(7) 0.0220(6) 0.0019(5) 0.0120(5) 0.0014(5)
C9 0.0325(7) 0.0193(6) 0.0211(6) 0.0016(5) 0.0078(5) 0.0009(5)
C10 0.0342(7) 0.0195(7) 0.0218(6) 0.0007(5) 0.0117(5) 0.0006(5)

_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 1.2577(15) . ?
O2 C9 1.2538(15) . ?
N1 H1 0.941(19) . ?
N1 C1 1.3710(16) . ?
N1 C5 1.3566(16) . ?
N2 H2 0.963(19) . ?
N2 C9 1.3727(17) . ?
N2 C10 1.3609(16) . ?
C1 C2 1.4291(18) . ?
C2 H2A 0.983(18) . ?
C2 C3 1.3575(18) . ?
C3 H3 0.986(18) . ?
C3 C4 1.4247(18) . ?
C4 C5 1.3672(18) . ?
C4 C6 1.4730(17) . ?
C5 H5 0.973(17) . ?
C6 C7 1.4287(18) . ?
C6 C10 1.3680(18) . ?
C7 H7 0.992(18) . ?
C7 C8 1.3596(18) . ?
C8 H8 1.001(17) . ?
C8 C9 1.4354(18) . ?
C10 H10 0.997(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 N1 H1 115.5(11) . . ?
C5 N1 H1 120.3(11) . . ?
C5 N1 C1 124.17(11) . . ?
C9 N2 H2 115.4(11) . . ?
C10 N2 H2 120.7(11) . . ?
C10 N2 C9 123.95(11) . . ?
O1 C1 N1 119.41(11) . . ?
O1 C1 C2 125.57(11) . . ?
N1 C1 C2 115.01(11) . . ?
C1 C2 H2A 116.1(10) . . ?
C3 C2 C1 120.90(12) . . ?
C3 C2 H2A 123.0(10) . . ?
C2 C3 H3 116.7(10) . . ?
C2 C3 C4 122.15(12) . . ?
C4 C3 H3 121.1(10) . . ?
C3 C4 C6 122.42(12) . . ?
C5 C4 C3 115.76(11) . . ?
C5 C4 C6 121.79(12) . . ?
N1 C5 C4 121.93(12) . . ?
N1 C5 H5 113.7(9) . . ?
C4 C5 H5 124.3(10) . . ?
C7 C6 C4 122.22(11) . . ?
C10 C6 C4 121.94(12) . . ?
C10 C6 C7 115.83(12) . . ?
C6 C7 H7 120.7(10) . . ?
C8 C7 C6 121.98(12) . . ?
C8 C7 H7 117.4(10) . . ?
C7 C8 H8 122.1(9) . . ?
C7 C8 C9 120.99(12) . . ?
C9 C8 H8 116.9(9) . . ?
O2 C9 N2 119.32(12) . . ?
O2 C9 C8 125.62(12) . . ?
N2 C9 C8 115.05(11) . . ?
N2 C10 C6 122.15(12) . . ?
N2 C10 H10 113.7(9) . . ?
C6 C10 H10 124.2(9) . . ?

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
_geom_hbond_publ_flag
N1 H1 O2 0.941(19) 1.800(19) 2.7287(14) 168.6(17) 2_656 yes
N2 H2 O1 0.963(19) 1.764(19) 2.7053(14) 164.7(16) 2_645 yes

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 -176.71(13) . . . . ?
N1 C1 C2 C3 2.45(19) . . . . ?
C1 N1 C5 C4 -1.7(2) . . . . ?
C1 C2 C3 C4 -2.1(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C2 C3 C4 C6 -178.29(13) . . . . ?
C3 C4 C5 N1 2.01(19) . . . . ?
C3 C4 C6 C7 -161.80(13) . . . . ?
C3 C4 C6 C10 19.3(2) . . . . ?
C4 C6 C7 C8 -178.76(12) . . . . ?
C4 C6 C10 N2 -179.86(12) . . . . ?
C5 N1 C1 O1 178.61(12) . . . . ?
C5 N1 C1 C2 -0.61(18) . . . . ?
C5 C4 C6 C7 20.1(2) . . . . ?
C5 C4 C6 C10 -158.75(13) . . . . ?
C6 C4 C5 N1 -179.81(12) . . . . ?
C6 C7 C8 C9 -2.1(2) . . . . ?
C7 C6 C10 N2 1.18(19) . . . . ?
C7 C8 C9 O2 -176.67(13) . . . . ?
C7 C8 C9 N2 2.45(19) . . . . ?
C9 N2 C10 C6 -0.7(2) . . . . ?
C10 N2 C9 O2 178.05(12) . . . . ?
C10 N2 C9 C8 -1.12(19) . . . . ?
C10 C6 C7 C8 0.2(2) . . . . ?

_shelx_res_file                  
;
TITL ada155_a.res in P2(1)/n
    ada155.res
    created by SHELXL-2018/3 at 09:19:53 on 09-Aug-2018
REM Old TITL ada155 in P2(1)/n
REM SHELXT solution in P2(1)/n
REM R1 0.131, Rweak 0.002, Alpha 0.015, Orientation as input
REM Formula found by SHELXT: C10 N2 O2
CELL 1.34139 6.9152 18.3958 7.2525 90 115.199 90
ZERR 4 0.0003 0.0008 0.0003 0 0.002 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H N O
DISP C 0.0137 0.007 57.1
DISP H -0 0 0.6481
DISP N 0.0241 0.0136 109.9
DISP O 0.0389 0.025 193.4
UNIT 40 32 8 8
EQIV $1 1.5-X,0.5+Y,1.5-Z
EQIV $2 1.5-X,-0.5+Y,0.5-Z

L.S. 30
PLAN  8
SIZE 0.06 0.09 0.1
TEMP -123
HTAB N1 O2_$1
HTAB N2 O1_$2
BOND $H
list 4
fmap 2 53
ACTA
HTAB
CONF
WPDB
MORE -1
REM <olex2.extras>
REM <HklSrc "%.\\ada155.hkl">
REM </olex2.extras>

WGHT    0.074400    0.263100
EXTI    0.020525
FVAR       0.89152
O1    4    0.758591    0.613265    0.395278    11.00000    0.04873    0.01731 =
         0.03043    0.00242    0.02003    0.00043
O2    4    0.640850    0.095599    0.567411    11.00000    0.05260    0.01661 =
         0.02608    0.00142    0.01454   -0.00090
N1    3    0.769912    0.515201    0.589698    11.00000    0.03492    0.01722 =
         0.02186    0.00014    0.01063    0.00072
H1    2    0.803722    0.548052    0.698584    11.00000    0.04436
N2    3    0.695179    0.191616    0.399096    11.00000    0.03856    0.01694 =
         0.02363   -0.00062    0.01320    0.00094
H2    2    0.706680    0.156579    0.305598    11.00000    0.04077
C1    1    0.745608    0.545421    0.408311    11.00000    0.03030    0.01873 =
         0.02406    0.00335    0.01084    0.00048
C2    1    0.703823    0.494726    0.246461    11.00000    0.03804    0.02216 =
         0.02135    0.00256    0.01110   -0.00068
H2A   2    0.692398    0.515215    0.116986    11.00000    0.03966
C3    1    0.682507    0.422676    0.273849    11.00000    0.03799    0.02185 =
         0.02151   -0.00182    0.01104   -0.00195
H3    2    0.649494    0.390921    0.154748    11.00000    0.03716
C4    1    0.707422    0.393672    0.464836    11.00000    0.02988    0.01760 =
         0.02254    0.00068    0.00993    0.00079
C5    1    0.754624    0.442988    0.619030    11.00000    0.03262    0.01811 =
         0.02124    0.00209    0.01016    0.00136
H5    2    0.785542    0.430245    0.758975    11.00000    0.02922
C6    1    0.690300    0.315323    0.497074    11.00000    0.02988    0.01743 =
         0.02167    0.00109    0.00850    0.00120
C7    1    0.654490    0.288052    0.664383    11.00000    0.03431    0.02113 =
         0.02262    0.00008    0.01121    0.00230
H7    2    0.640337    0.321772    0.764617    11.00000    0.03797
C8    1    0.642755    0.215626    0.695564    11.00000    0.03653    0.02106 =
         0.02197    0.00185    0.01198    0.00137
H8    2    0.619247    0.196441    0.813537    11.00000    0.03472
C9    1    0.659120    0.163086    0.556557    11.00000    0.03247    0.01926 =
         0.02112    0.00158    0.00776    0.00091
C10   1    0.711309    0.264056    0.370175    11.00000    0.03422    0.01951 =
         0.02175    0.00075    0.01170    0.00058
H10   2    0.742762    0.275441    0.251288    11.00000    0.03065
HKLF 4




REM  ada155_a.res in P2(1)/n
REM wR2 = 0.1289, GooF = S = 1.056, Restrained GooF = 1.056 for all data
REM R1 = 0.0450 for 1637 Fo > 4sig(Fo) and 0.0518 for all 1912 data
REM 160 parameters refined using 0 restraints

END

WGHT      0.0744      0.2631

REM Instructions for potential hydrogen bonds
HTAB N1 O2_$1
HTAB N2 O1_$2
EQIV $3 -x+3/2, y+1/2, -z+1/2
HTAB C2 O2_$3
EQIV $4 x+1/2, -y+1/2, z+1/2
HTAB C5 O2_$4
EQIV $5 -x+3/2, y-1/2, -z+3/2
HTAB C8 O1_$5

REM Highest difference peak  0.251,  deepest hole -0.285,  1-sigma level  0.063
Q1    1   0.7693  0.5186  0.3393  11.00000  0.05    0.25
Q2    1   0.6795  0.1945  0.6438  11.00000  0.05    0.25
Q3    1   0.6973  0.3569  0.4798  11.00000  0.05    0.21
Q4    1   0.7541  0.4188  0.5464  11.00000  0.05    0.19
Q5    1   0.6399  0.2867  0.4007  11.00000  0.05    0.18
Q6    1   0.9279  0.6173  0.4435  11.00000  0.05    0.18
Q7    1   0.6335  0.2582  0.6692  11.00000  0.05    0.17
Q8    1   0.6661  0.4176  0.5222  11.00000  0.05    0.16
;
_shelx_res_checksum              86636
_olex2_exptl_crystal_mounting_method 'mounted on a Cryoloop'
_olex2_submission_original_sample_id 'Fe-dpy DMSO/EtOH'
_olex2_submission_special_instructions 'No special instructions were received'
