# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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. 
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data_han525
_audit_block_doi                 10.5517/ccdc.csd.cc28hf6f
_database_code_depnum_ccdc_archive 'CCDC 2100194'
loop_
_audit_author_name
_audit_author_address
'Michel Simard'
;Universite de montreal
Canada
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2021-11-30 downloaded from the CCDC.
;
_audit_creation_date             2017-08-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H9 N O2'
_chemical_formula_sum            'C6 H9 N O2'
_chemical_formula_weight         127.14
_chemical_absolute_configuration ad
_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 0.0150 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 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   4.8817(2)
_cell_length_b                   8.1667(4)
_cell_length_c                   14.6054(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     582.28(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9469
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.64
_cell_measurement_theta_min      4.71
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1469 before and 0.0783 after correction. The Ratio of minimum to maximum transmission is 0.7548. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Yellow
_exptl_crystal_colour_primary    Yellow
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_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  0.0534
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4745
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.450
_diffrn_reflns_theta_min         5.270
_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 0.998
_diffrn_measured_fraction_theta_max 0.996
_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'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                1306
_reflns_number_total             1329
_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) V8.34A; 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) V8.34A; 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         0.260
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 507 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(12)
_refine_ls_extinction_coef       0.107(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.068
_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)+(0.0617P)²+0.0849P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.0990
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B)
;
_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 0.7429(3) 0.31299(16) 0.83526(8) 0.0254(3) Uani 1 1 d . . . . .
O2 O 1.0148(3) 0.51623(19) 0.78796(10) 0.0318(4) Uani 1 1 d . . . . .
N1 N 0.6879(3) 0.61312(18) 0.65083(10) 0.0194(4) Uani 1 1 d . . . . .
H1A H 0.860(6) 0.646(3) 0.6690(16) 0.027(6) Uiso 1 1 d . . . . .
H1B H 0.570(7) 0.698(4) 0.664(2) 0.044(8) Uiso 1 1 d . . . . .
C1 C 0.6171(3) 0.45603(19) 0.69990(11) 0.0200(4) Uani 1 1 d . . . . .
H1 H 0.4219 0.4589 0.7206 0.024 Uiso 1 1 calc R . . . .
C2 C 0.6573(5) 0.3185(2) 0.62859(13) 0.0312(5) Uani 1 1 d . . . . .
H2A H 0.8380 0.2654 0.6366 0.037 Uiso 1 1 calc R . . . .
H2B H 0.5124 0.2344 0.6348 0.037 Uiso 1 1 calc R . . . .
C3 C 0.6399(4) 0.4009(2) 0.53649(12) 0.0247(4) Uani 1 1 d . . . . .
H3 H 0.7331 0.3490 0.4829 0.030 Uiso 1 1 calc R . . . .
C4 C 0.3993(3) 0.5137(2) 0.51971(12) 0.0233(4) Uani 1 1 d . . . . .
H4A H 0.3438 0.5336 0.4555 0.028 Uiso 1 1 calc R . . . .
H4B H 0.2468 0.5115 0.5644 0.028 Uiso 1 1 calc R . . . .
C5 C 0.6692(4) 0.5822(2) 0.55091(11) 0.0213(4) Uani 1 1 d . . . . .
H5 H 0.7829 0.6483 0.5076 0.026 Uiso 1 1 calc R . . . .
C6 C 0.8074(3) 0.4290(2) 0.78244(11) 0.0194(4) 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
O1 0.0274(6) 0.0257(7) 0.0232(6) 0.0046(4) -0.0036(5) -0.0073(5)
O2 0.0259(7) 0.0358(8) 0.0337(7) 0.0067(6) -0.0078(5) -0.0125(6)
N1 0.0196(7) 0.0164(6) 0.0222(7) -0.0001(5) -0.0012(5) 0.0005(6)
C1 0.0174(7) 0.0184(7) 0.0240(8) 0.0027(6) -0.0009(6) -0.0023(6)
C2 0.0498(12) 0.0172(8) 0.0268(9) -0.0013(7) -0.0133(8) 0.0007(8)
C3 0.0299(9) 0.0205(8) 0.0239(8) -0.0037(6) -0.0040(7) 0.0063(7)
C4 0.0218(8) 0.0250(8) 0.0231(8) 0.0003(6) -0.0029(6) 0.0024(7)
C5 0.0210(8) 0.0219(8) 0.0209(8) 0.0000(6) 0.0015(6) 0.0003(6)
C6 0.0178(7) 0.0197(7) 0.0207(7) -0.0009(6) -0.0002(6) -0.0010(6)

_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 C6 1.261(2) . ?
O2 C6 1.241(2) . ?
N1 H1A 0.92(3) . ?
N1 H1B 0.92(3) . ?
N1 C1 1.510(2) . ?
N1 C5 1.484(2) . ?
C1 H1 1.0000 . ?
C1 C2 1.544(2) . ?
C1 C6 1.538(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.507(2) . ?
C3 H3 1.0000 . ?
C3 C4 1.512(2) . ?
C3 C5 1.502(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.502(2) . ?
C5 H5 1.0000 . ?

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
H1A N1 H1B 107(2) . . ?
C1 N1 H1A 108.8(15) . . ?
C1 N1 H1B 113.4(19) . . ?
C5 N1 H1A 112.9(15) . . ?
C5 N1 H1B 107.2(18) . . ?
C5 N1 C1 107.95(13) . . ?
N1 C1 H1 110.0 . . ?
N1 C1 C2 105.59(13) . . ?
N1 C1 C6 110.86(13) . . ?
C2 C1 H1 110.0 . . ?
C6 C1 H1 110.0 . . ?
C6 C1 C2 110.35(14) . . ?
C1 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
H2A C2 H2B 108.7 . . ?
C3 C2 C1 105.68(13) . . ?
C3 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 117.41(17) . . ?
C4 C3 H3 119.0 . . ?
C5 C3 C2 108.04(14) . . ?
C5 C3 H3 119.0 . . ?
C5 C3 C4 59.78(12) . . ?
C3 C4 H4A 117.8 . . ?
C3 C4 H4B 117.8 . . ?
H4A C4 H4B 114.9 . . ?
C5 C4 C3 59.77(11) . . ?
C5 C4 H4A 117.8 . . ?
C5 C4 H4B 117.8 . . ?
N1 C5 C3 108.15(14) . . ?
N1 C5 C4 114.58(13) . . ?
N1 C5 H5 119.7 . . ?
C3 C5 C4 60.45(12) . . ?
C3 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
O1 C6 C1 115.88(14) . . ?
O2 C6 O1 126.53(16) . . ?
O2 C6 C1 117.47(15) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.92(3) 2.37(3) 3.229(2) 155.1(19) 3_756
N1 H1A O2 0.92(3) 2.17(2) 2.6802(19) 113.8(18) .
N1 H1B O1 0.92(3) 1.79(3) 2.670(2) 158(3) 3_656

_iucr_refine_instructions_details 
;

    han525.res created by SHELXL-2014/7

TITL han525_a.res in P2(1)2(1)2(1)
REM Old TITL han525 in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.125, Rweak 0.030, Alpha 0.001, Orientation as input
REM Flack x = 0.273 ( 0.060 ) from Parsons' quotients
REM Formula found by SHELXT: C6 N O2
rem N1-H1A 0.887 2.397 155.30 3.224 O1 [ -x+2, y+1/2, -z+3/2 ]
rem N1-H1A 0.887 2.187 114.40 2.678 O2
rem N1-H1B 0.941 1.772 158.97 2.671 O1 [ -x+1, y+1/2, -z+3/2 ]
CELL 1.34139 4.8817 8.1667 14.6054 90 90 90
ZERR 4 0.0002 0.0004 0.0006 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 N O
DISP C 0.015 0.007 57.748
DISP H -0 0 0.648
DISP N 0.025 0.014 110.512
DISP O 0.041 0.025 193.954
UNIT 24 36 4 8
EQIV $1 2-X,0.5+Y,1.5-Z
EQIV $2 1-X,0.5+Y,1.5-Z
 
L.S. 10
PLAN  5
TEMP -123
HTAB N1 O1_$1
HTAB N1 O2
HTAB N1 O1_$2
HTAB
BOND $H
list 4
fmap 2
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\han525_w5.hkl">
REM </olex2.extras>
 
WGHT    0.061700    0.084900
EXTI    0.106984
FVAR       2.03022
O1    4    0.742891    0.312994    0.835259    11.00000    0.02737    0.02567 =
         0.02325    0.00461   -0.00360   -0.00729
O2    4    1.014825    0.516228    0.787963    11.00000    0.02590    0.03576 =
         0.03370    0.00668   -0.00778   -0.01250
N1    3    0.687945    0.613116    0.650834    11.00000    0.01964    0.01643 =
         0.02225   -0.00014   -0.00125    0.00052
H1A   2    0.859954    0.646310    0.669026    11.00000    0.02712
H1B   2    0.569736    0.698214    0.664060    11.00000    0.04418
C1    1    0.617148    0.456031    0.699903    11.00000    0.01743    0.01844 =
         0.02405    0.00267   -0.00093   -0.00234
AFIX  13
H1    2    0.421949    0.458892    0.720605    11.00000   -1.20000
AFIX   0
C2    1    0.657275    0.318538    0.628594    11.00000    0.04976    0.01721 =
         0.02678   -0.00128   -0.01328    0.00072
AFIX  23
H2A   2    0.837955    0.265395    0.636630    11.00000   -1.20000
H2B   2    0.512428    0.234430    0.634833    11.00000   -1.20000
AFIX   0
C3    1    0.639889    0.400944    0.536493    11.00000    0.02989    0.02046 =
         0.02387   -0.00375   -0.00403    0.00630
AFIX  13
H3    2    0.733058    0.349035    0.482869    11.00000   -1.20000
AFIX   0
C4    1    0.399326    0.513655    0.519711    11.00000    0.02176    0.02496 =
         0.02308    0.00027   -0.00286    0.00236
AFIX  23
H4A   2    0.343811    0.533587    0.455476    11.00000   -1.20000
H4B   2    0.246818    0.511479    0.564373    11.00000   -1.20000
AFIX   0
C5    1    0.669168    0.582187    0.550912    11.00000    0.02098    0.02187 =
         0.02095   -0.00002    0.00146    0.00030
AFIX  13
H5    2    0.782906    0.648283    0.507590    11.00000   -1.20000
AFIX   0
C6    1    0.807407    0.428975    0.782444    11.00000    0.01785    0.01975 =
         0.02071   -0.00088   -0.00018   -0.00103
HKLF 4
 
REM  han525_a.res in P2(1)2(1)2(1)
REM R1 =  0.0357 for    1306 Fo > 4sig(Fo)  and  0.0364 for all    1329 data
REM     91 parameters refined using      0 restraints
 
END  
     
WGHT      0.0617      0.0850 

REM Instructions for potential hydrogen bonds
HTAB N1 O1_$1
HTAB N1 O2
HTAB N1 O1_$2
EQIV $3 x-1, y, z
HTAB C1 O2_$3
EQIV $4 -x+2, y-1/2, -z+3/2
HTAB C2 O2_$4
EQIV $5 -x+3/2, -y+1, z-1/2
HTAB C4 O2_$5
HTAB C5 O1_$5

REM Highest difference peak  0.260,  deepest hole -0.222,  1-sigma level  0.048
Q1    1   0.6962  0.4845  0.5421  11.00000  0.05    0.26
Q2    1   0.7106  0.4453  0.7372  11.00000  0.05    0.23
Q3    1   0.5044  0.4438  0.5228  11.00000  0.05    0.21
Q4    1   0.5279  0.4728  0.5387  11.00000  0.05    0.18
Q5    1   0.5096  0.5909  0.5242  11.00000  0.05    0.17

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0357 for 1306 Fo > 4sig(Fo) and 0.0364 for all 4782 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.26, deepest hole -0.22
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0364
  REM R1_gt = 0.0357
  REM wR_ref = 0.0990
  REM GOOF = 1.068
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 4782
  REM Reflections_gt = 1306
  REM Parameters = n/a
  REM Hole = -0.22
  REM Peak = 0.26
  REM Flack = -0.02(12)

  
;
_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_han527
_audit_block_doi                 10.5517/ccdc.csd.cc28hf9j
_database_code_depnum_ccdc_archive 'CCDC 2100197'
loop_
_audit_author_name
_audit_author_address
'Michel Simard'
;Universite de montreal
Canada
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2021-11-30 downloaded from the CCDC.
;
_audit_creation_date             2017-08-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C7 H12 N O2, H2 O'
_chemical_formula_sum            'C7 H14 Cl N O3'
_chemical_formula_weight         195.64
_chemical_absolute_configuration ad
_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 0.0150 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'
Cl Cl 0.3290 0.5400 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0250 0.0140 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0410 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   7.2340(6)
_cell_length_b                   10.1941(8)
_cell_length_c                   13.0701(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     963.84(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9852
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.87
_cell_measurement_theta_min      2.94
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.155
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5013
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1685 before and 0.1209 after correction. The Ratio of minimum to maximum transmission is 0.6667. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_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 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  0.0574
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10311
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.724
_diffrn_reflns_theta_min         4.786
_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 0.997
_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'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                2163
_reflns_number_total             2213
_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) V8.34A; 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) V8.34A; 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         0.206
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 873 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(12)
_refine_ls_extinction_coef       0.022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.070
_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)+(0.0405P)²+0.1290P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0777
_refine_ls_wR_factor_ref         0.0789
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
;
_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
Cl1 Cl -0.01351(6) 0.28194(5) 0.67117(4) 0.03319(17) Uani 1 1 d . . . . .
O1 O 0.4611(2) 0.37335(15) 0.56882(13) 0.0373(4) Uani 1 1 d . . . . .
O2 O 0.4729(2) 0.58879(15) 0.60201(14) 0.0433(4) Uani 1 1 d . . . . .
H2 H 0.362(5) 0.581(3) 0.630(2) 0.050(8) Uiso 1 1 d . . . . .
N1 N 0.7822(3) 0.37369(18) 0.46085(14) 0.0295(4) Uani 1 1 d . . . . .
H1A H 0.683(5) 0.326(4) 0.438(3) 0.066(10) Uiso 1 1 d . . . . .
H1B H 0.852(4) 0.326(3) 0.506(2) 0.038(7) Uiso 1 1 d . . . . .
C1 C 0.7161(3) 0.49998(19) 0.50580(15) 0.0286(4) Uani 1 1 d . . . . .
H1 H 0.8113 0.5352 0.5540 0.034 Uiso 1 1 calc R . . . .
C2 C 0.6990(3) 0.5913(2) 0.41279(18) 0.0400(5) Uani 1 1 d . . . . .
H2A H 0.5785 0.5789 0.3782 0.048 Uiso 1 1 calc R . . . .
H2B H 0.7109 0.6843 0.4336 0.048 Uiso 1 1 calc R . . . .
C3 C 0.8583(3) 0.5512(3) 0.34269(19) 0.0414(5) Uani 1 1 d . . . . .
H3 H 0.8325 0.5643 0.2682 0.050 Uiso 1 1 calc R . . . .
C4 C 1.0559(4) 0.5933(3) 0.3760(3) 0.0524(7) Uani 1 1 d . . . . .
H4A H 1.1324 0.6275 0.3191 0.063 Uiso 1 1 calc R . . . .
H4B H 1.0573 0.6543 0.4349 0.063 Uiso 1 1 calc R . . . .
C5 C 1.1006(3) 0.4501(2) 0.4051(2) 0.0399(5) Uani 1 1 d . . . . .
H5A H 1.2008 0.4109 0.3635 0.048 Uiso 1 1 calc R . . . .
H5B H 1.1245 0.4375 0.4790 0.048 Uiso 1 1 calc R . . . .
C6 C 0.9069(3) 0.4078(2) 0.37179(16) 0.0338(5) Uani 1 1 d . . . . .
H6 H 0.9036 0.3441 0.3137 0.041 Uiso 1 1 calc R . . . .
C7 C 0.5358(3) 0.47888(19) 0.56229(15) 0.0297(4) Uani 1 1 d . . . . .
O3 O 0.1333(2) 0.57136(18) 0.66427(14) 0.0401(4) Uani 1 1 d . . . . .
H3A H 0.091(7) 0.492(5) 0.681(4) 0.099(15) Uiso 1 1 d . . . . .
H3B H 0.088(5) 0.621(4) 0.706(3) 0.061(10) 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
Cl1 0.0321(2) 0.0318(3) 0.0357(3) -0.00021(17) 0.00477(19) -0.00082(19)
O1 0.0322(8) 0.0294(7) 0.0502(9) -0.0035(6) 0.0069(6) -0.0037(6)
O2 0.0407(9) 0.0289(7) 0.0602(10) -0.0079(7) 0.0174(8) -0.0010(7)
N1 0.0265(8) 0.0255(8) 0.0366(9) 0.0000(7) 0.0004(7) 0.0012(7)
C1 0.0275(9) 0.0244(9) 0.0341(10) -0.0001(8) 0.0003(8) 0.0004(8)
C2 0.0390(11) 0.0360(11) 0.0449(12) 0.0115(10) 0.0097(9) 0.0108(9)
C3 0.0417(11) 0.0408(13) 0.0417(12) 0.0113(10) 0.0095(10) 0.0114(10)
C4 0.0426(13) 0.0348(13) 0.0796(19) 0.0066(12) 0.0172(13) 0.0008(11)
C5 0.0307(11) 0.0400(12) 0.0490(13) 0.0029(10) 0.0076(9) 0.0035(9)
C6 0.0344(10) 0.0323(11) 0.0348(11) -0.0001(8) 0.0043(8) 0.0037(8)
C7 0.0283(10) 0.0290(10) 0.0318(9) -0.0005(7) -0.0014(7) 0.0012(8)
O3 0.0413(8) 0.0334(9) 0.0455(9) -0.0063(8) 0.0083(8) -0.0006(7)

_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 C7 1.207(3) . ?
O2 H2 0.89(3) . ?
O2 C7 1.316(2) . ?
N1 H1A 0.92(4) . ?
N1 H1B 0.91(3) . ?
N1 C1 1.494(3) . ?
N1 C6 1.513(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.536(3) . ?
C1 C7 1.514(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.528(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.555(4) . ?
C3 C6 1.550(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.543(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.530(3) . ?
C6 H6 1.0000 . ?
O3 H3A 0.89(5) . ?
O3 H3B 0.81(4) . ?

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
C7 O2 H2 114(2) . . ?
H1A N1 H1B 111(3) . . ?
C1 N1 H1A 110(2) . . ?
C1 N1 H1B 112.5(17) . . ?
C1 N1 C6 107.17(16) . . ?
C6 N1 H1A 110(2) . . ?
C6 N1 H1B 106.8(17) . . ?
N1 C1 H1 109.7 . . ?
N1 C1 C2 103.70(16) . . ?
N1 C1 C7 110.19(16) . . ?
C2 C1 H1 109.7 . . ?
C7 C1 H1 109.7 . . ?
C7 C1 C2 113.73(17) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 C1 104.56(18) . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C2 C3 H3 114.0 . . ?
C2 C3 C4 116.8(2) . . ?
C2 C3 C6 106.03(19) . . ?
C4 C3 H3 114.0 . . ?
C6 C3 H3 114.0 . . ?
C6 C3 C4 89.06(19) . . ?
C3 C4 H4A 113.6 . . ?
C3 C4 H4B 113.6 . . ?
H4A C4 H4B 110.9 . . ?
C5 C4 C3 90.01(19) . . ?
C5 C4 H4A 113.6 . . ?
C5 C4 H4B 113.6 . . ?
C4 C5 H5A 113.6 . . ?
C4 C5 H5B 113.6 . . ?
H5A C5 H5B 110.9 . . ?
C6 C5 C4 90.26(19) . . ?
C6 C5 H5A 113.6 . . ?
C6 C5 H5B 113.6 . . ?
N1 C6 C3 105.70(17) . . ?
N1 C6 C5 113.09(18) . . ?
N1 C6 H6 114.9 . . ?
C3 C6 H6 114.9 . . ?
C5 C6 C3 90.66(19) . . ?
C5 C6 H6 114.9 . . ?
O1 C7 O2 125.17(19) . . ?
O1 C7 C1 123.15(18) . . ?
O2 C7 C1 111.69(17) . . ?
H3A O3 H3B 105(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
O2 H2 O3 0.89(3) 1.71(4) 2.594(2) 171(3) .
N1 H1A Cl1 0.92(4) 2.29(4) 3.173(2) 161(3) 4_556
N1 H1B Cl1 0.91(3) 2.42(3) 3.2581(19) 154(2) 1_655
N1 H1B O1 0.91(3) 2.39(3) 2.858(2) 112(2) 4_556
O3 H3A Cl1 0.89(5) 2.28(5) 3.1369(19) 162(4) .
O3 H3B Cl1 0.81(4) 2.36(4) 3.1599(19) 169(3) 3_556

_iucr_refine_instructions_details 
;

    han527.res created by SHELXL-2014/7

TITL han527_a.res in P2(1)2(1)2(1)
REM Old TITL han527 in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.101, Rweak 0.028, Alpha 0.001, Orientation as input
REM Flack x = 0.319 ( 0.006 ) from Parsons' quotients
REM Formula found by SHELXT: C7 N O3 Cl
rem O2-H2 0.887 1.715 170.90 2.594 O3
rem N1-H1A 0.921 2.290 160.59 3.173 Cl1 [ x+1/2, -y+1/2, -z+1 ]
rem N1-H1B 0.911 2.416 153.80 3.258 Cl1 [ x+1, y, z ]
rem N1-H1B 0.911 2.389 111.99 2.858 O1 [ x+1/2, -y+1/2, -z+1 ]
rem O3-H3A 0.889 2.278 162.31 3.137 Cl1
rem O3-H3B 0.810 2.361 168.84 3.160 Cl1 [ -x, y+1/2, -z+3/2 ]
CELL 1.34139 7.234 10.1941 13.0701 90 90 90
ZERR 4 0.0006 0.0008 0.001 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 Cl N O
DISP C 0.015 0.007 57.748
DISP Cl 0.329 0.54 4086.178
DISP H -0 0 0.648
DISP N 0.025 0.014 110.512
DISP O 0.041 0.025 193.954
UNIT 28 56 4 4 12
EQIV $1 0.5+X,0.5-Y,1-Z
EQIV $2 1+X,+Y,+Z
EQIV $3 -X,0.5+Y,1.5-Z
 
L.S. 10
PLAN  5
TEMP -123
HTAB O2 O3
HTAB N1 Cl1_$1
HTAB N1 Cl1_$2
HTAB N1 O1_$1
HTAB O3 Cl1
HTAB O3 Cl1_$3
HTAB
BOND $H
list 4
fmap 2
ACTA
REM <olex2.extras>
REM <HklSrc "%.\\han527_w12.hkl">
REM </olex2.extras>
 
WGHT    0.040500    0.129000
EXTI    0.022031
FVAR       1.18968
CL1   3   -0.013508    0.281939    0.671167    11.00000    0.03209    0.03177 =
         0.03571   -0.00021    0.00477   -0.00082
O1    5    0.461146    0.373350    0.568819    11.00000    0.03223    0.02943 =
         0.05019   -0.00348    0.00694   -0.00373
O2    5    0.472887    0.588791    0.602012    11.00000    0.04072    0.02886 =
         0.06017   -0.00786    0.01740   -0.00096
H2    2    0.361548    0.581339    0.629789    11.00000    0.04952
N1    4    0.782219    0.373689    0.460845    11.00000    0.02653    0.02548 =
         0.03660   -0.00004    0.00043    0.00124
H1A   2    0.682915    0.325606    0.437662    11.00000    0.06554
H1B   2    0.851510    0.326076    0.505631    11.00000    0.03796
C1    1    0.716126    0.499979    0.505803    11.00000    0.02750    0.02436 =
         0.03407   -0.00009    0.00025    0.00044
AFIX  13
H1    2    0.811309    0.535181    0.554018    11.00000   -1.20000
AFIX   0
C2    1    0.698997    0.591294    0.412789    11.00000    0.03902    0.03605 =
         0.04487    0.01146    0.00969    0.01083
AFIX  23
H2A   2    0.578533    0.578944    0.378159    11.00000   -1.20000
H2B   2    0.710867    0.684288    0.433607    11.00000   -1.20000
AFIX   0
C3    1    0.858320    0.551157    0.342692    11.00000    0.04170    0.04076 =
         0.04169    0.01132    0.00947    0.01137
AFIX  13
H3    2    0.832537    0.564273    0.268224    11.00000   -1.20000
AFIX   0
C4    1    1.055924    0.593316    0.376006    11.00000    0.04264    0.03483 =
         0.07961    0.00661    0.01721    0.00080
AFIX  23
H4A   2    1.132411    0.627528    0.319146    11.00000   -1.20000
H4B   2    1.057334    0.654345    0.434921    11.00000   -1.20000
AFIX   0
C5    1    1.100643    0.450124    0.405067    11.00000    0.03067    0.04004 =
         0.04895    0.00292    0.00757    0.00346
AFIX  23
H5A   2    1.200751    0.410904    0.363454    11.00000   -1.20000
H5B   2    1.124472    0.437455    0.478998    11.00000   -1.20000
AFIX   0
C6    1    0.906856    0.407821    0.371790    11.00000    0.03435    0.03231 =
         0.03484   -0.00013    0.00433    0.00372
AFIX  13
H6    2    0.903583    0.344068    0.313669    11.00000   -1.20000
AFIX   0
C7    1    0.535847    0.478883    0.562289    11.00000    0.02825    0.02904 =
         0.03183   -0.00048   -0.00144    0.00116
 
O3    5    0.133271    0.571359    0.664274    11.00000    0.04134    0.03336 =
         0.04554   -0.00631    0.00829   -0.00064
H3A   2    0.090794    0.492448    0.681126    11.00000    0.09945
H3B   2    0.087759    0.620689    0.705847    11.00000    0.06134
HKLF 4
 
REM  han527_a.res in P2(1)2(1)2(1)
REM R1 =  0.0301 for    2163 Fo > 4sig(Fo)  and  0.0308 for all    2213 data
REM    130 parameters refined using      0 restraints
 
END  
     
WGHT      0.0405      0.1290 

REM Instructions for potential hydrogen bonds
HTAB O2 O3
HTAB N1 Cl1_$1
HTAB N1 Cl1_$2
HTAB N1 O1_$1
EQIV $4 x+3/2, -y+1/2, -z+1
HTAB C5 Cl1_$4
HTAB O3 Cl1
HTAB O3 Cl1_$3

REM Highest difference peak  0.206,  deepest hole -0.237,  1-sigma level  0.051
Q1    1   0.0229  0.4161  0.6454  11.00000  0.05    0.21
Q2    1   0.0744  0.3362  0.6438  11.00000  0.05    0.18
Q3    1   0.6883  0.5437  0.4580  11.00000  0.05    0.17
Q4    1   0.7249  0.3582  0.4460  11.00000  0.05    0.15
Q5    1   0.1382  0.4246  0.6572  11.00000  0.05    0.14

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0301 for 2163 Fo > 4sig(Fo) and 0.0308 for all 10360 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.21, deepest hole -0.24
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0308
  REM R1_gt = 0.0301
  REM wR_ref = 0.0789
  REM GOOF = 1.070
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 10360
  REM Reflections_gt = 2163
  REM Parameters = n/a
  REM Hole = -0.24
  REM Peak = 0.21
  REM Flack = 0.003(12)

  
;
_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_han562
_audit_block_doi                 10.5517/ccdc.csd.cc28hf8h
_database_code_depnum_ccdc_archive 'CCDC 2100196'
loop_
_audit_author_name
_audit_author_address
'Michel Simard'
;Universite de montreal
Canada
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2021-11-30 downloaded from the CCDC.
;
_audit_creation_date             2017-08-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H11 N O2'
_chemical_formula_sum            'C7 H11 N O2'
_chemical_formula_weight         141.17
_chemical_absolute_configuration ad
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.28430(7)
_cell_length_b                   9.55030(13)
_cell_length_c                   6.61740(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.1230(4)
_cell_angle_gamma                90
_cell_volume                     329.734(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9896
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.26
_cell_measurement_theta_min      6.78
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.860
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0981 before and 0.0248 after correction. The Ratio of minimum to maximum transmission is 0.8970. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             152
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.04
_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 Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. 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 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0142
_diffrn_reflns_av_unetI/netI     0.0065
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13824
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.336
_diffrn_reflns_theta_min         6.776
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.867
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.974
_reflns_number_gt                1295
_reflns_number_total             1296
_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) V8.34A; 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) V8.34A; 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         0.234
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 600 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.05(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         1296
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0286
_refine_ls_R_factor_gt           0.0286
_refine_ls_restrained_S_all      1.048
_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)+(0.0498P)²+0.0863P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0762
_refine_ls_wR_factor_ref         0.0762
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
;
_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 0.7003(2) 0.44089(14) 0.5053(2) 0.0181(3) Uani 1 1 d . . . . .
O2 O 0.7407(3) 0.67148(16) 0.4637(3) 0.0251(4) Uani 1 1 d . . . . .
N1 N 0.1847(3) 0.44074(16) 0.4023(2) 0.0145(3) Uani 1 1 d . . . . .
C1 C 0.3184(3) 0.57961(19) 0.4219(3) 0.0147(4) Uani 1 1 d . . . . .
H1 H 0.2609 0.6334 0.5361 0.018 Uiso 1 1 calc R . . . .
C2 C 0.2207(4) 0.6537(2) 0.2186(3) 0.0186(4) Uani 1 1 d . . . . .
H2A H 0.0600 0.7051 0.2266 0.022 Uiso 1 1 calc R . . . .
H2B H 0.3502 0.7206 0.1836 0.022 Uiso 1 1 calc R . . . .
C3 C 0.1741(4) 0.5367(2) 0.0600(3) 0.0212(4) Uani 1 1 d . . . . .
H3 H 0.0350 0.5574 -0.0572 0.025 Uiso 1 1 calc R . . . .
C4 C 0.4171(4) 0.4672(2) -0.0042(3) 0.0225(4) Uani 1 1 d . . . . .
H4A H 0.4104 0.4602 -0.1542 0.027 Uiso 1 1 calc R . . . .
H4B H 0.5802 0.5101 0.0613 0.027 Uiso 1 1 calc R . . . .
C5 C 0.3525(4) 0.3285(2) 0.0971(3) 0.0193(4) Uani 1 1 d . . . . .
H5A H 0.2966 0.2527 -0.0022 0.023 Uiso 1 1 calc R . . . .
H5B H 0.4901 0.2954 0.2058 0.023 Uiso 1 1 calc R . . . .
C6 C 0.1292(3) 0.4017(2) 0.1798(3) 0.0179(4) Uani 1 1 d . . . . .
H6 H -0.0420 0.3570 0.1366 0.021 Uiso 1 1 calc R . . . .
C7 C 0.6131(3) 0.5620(2) 0.4677(3) 0.0159(4) Uani 1 1 d . . . . .
H1A H 0.032(6) 0.448(3) 0.448(4) 0.025(6) Uiso 1 1 d . . . . .
H1B H 0.281(6) 0.371(3) 0.475(4) 0.023(6) 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 0.0123(6) 0.0169(7) 0.0256(7) 0.0023(5) 0.0048(5) 0.0011(5)
O2 0.0139(6) 0.0151(7) 0.0479(9) -0.0069(7) 0.0096(6) -0.0032(6)
N1 0.0098(7) 0.0136(8) 0.0209(8) -0.0001(6) 0.0042(6) 0.0001(6)
C1 0.0117(8) 0.0128(9) 0.0203(8) -0.0020(7) 0.0049(7) -0.0013(7)
C2 0.0170(9) 0.0162(10) 0.0234(9) 0.0034(8) 0.0061(7) 0.0039(7)
C3 0.0188(10) 0.0236(10) 0.0209(9) 0.0022(8) 0.0026(7) 0.0043(8)
C4 0.0249(9) 0.0237(10) 0.0206(9) 0.0012(8) 0.0083(7) 0.0051(9)
C5 0.0165(9) 0.0177(9) 0.0244(10) -0.0052(7) 0.0057(7) -0.0005(7)
C6 0.0117(7) 0.0202(9) 0.0216(9) -0.0039(7) 0.0024(6) -0.0007(7)
C7 0.0129(8) 0.0175(9) 0.0181(8) -0.0037(7) 0.0052(6) -0.0003(8)

_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 C7 1.255(2) . ?
O2 C7 1.247(2) . ?
N1 C1 1.499(2) . ?
N1 C6 1.502(2) . ?
N1 H1A 0.91(3) . ?
N1 H1B 0.93(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.535(3) . ?
C1 C7 1.548(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.526(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.563(3) . ?
C3 C6 1.552(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.547(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.545(2) . ?
C6 H6 1.0000 . ?

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 C6 108.73(14) . . ?
C1 N1 H1A 109.4(18) . . ?
C1 N1 H1B 112.1(18) . . ?
C6 N1 H1A 107.5(17) . . ?
C6 N1 H1B 109.8(18) . . ?
H1A N1 H1B 109(2) . . ?
N1 C1 H1 109.0 . . ?
N1 C1 C2 104.07(14) . . ?
N1 C1 C7 111.51(15) . . ?
C2 C1 H1 109.0 . . ?
C2 C1 C7 114.18(15) . . ?
C7 C1 H1 109.0 . . ?
C1 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 C1 105.12(15) . . ?
C3 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
C2 C3 H3 114.0 . . ?
C2 C3 C4 116.59(17) . . ?
C2 C3 C6 106.15(16) . . ?
C4 C3 H3 114.0 . . ?
C6 C3 H3 114.0 . . ?
C6 C3 C4 89.12(14) . . ?
C3 C4 H4A 113.7 . . ?
C3 C4 H4B 113.7 . . ?
H4A C4 H4B 110.9 . . ?
C5 C4 C3 89.93(15) . . ?
C5 C4 H4A 113.7 . . ?
C5 C4 H4B 113.7 . . ?
C4 C5 H5A 113.7 . . ?
C4 C5 H5B 113.7 . . ?
H5A C5 H5B 110.9 . . ?
C6 C5 C4 89.95(14) . . ?
C6 C5 H5A 113.7 . . ?
C6 C5 H5B 113.7 . . ?
N1 C6 C3 105.81(16) . . ?
N1 C6 C5 114.72(14) . . ?
N1 C6 H6 114.4 . . ?
C3 C6 H6 114.4 . . ?
C5 C6 C3 90.46(14) . . ?
C5 C6 H6 114.4 . . ?
O1 C7 C1 117.72(16) . . ?
O2 C7 O1 126.47(16) . . ?
O2 C7 C1 115.81(17) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.91(3) 1.85(3) 2.751(2) 170(3) 1_455
N1 H1A O2 0.91(3) 2.64(3) 3.290(2) 129(2) 1_455
N1 H1B O2 0.93(3) 1.96(3) 2.728(2) 140(3) 2_646

_iucr_refine_instructions_details 
;

    han562.res created by SHELXL-2014/7

TITL han562_a.res in P2(1)
REM Old TITL han562 in P2(1)
REM SHELXT solution in P2(1)
REM R1 0.092, Rweak 0.026, Alpha 0.005, Orientation as input
REM Flack x = 0.072 ( 0.030 ) from Parsons' quotients
REM Formula found by SHELXT: C7 N O2
rem N1-H1A 0.909 1.853 169.77 2.752 O1 [ x-1, y, z ]
rem N1-H1A 0.909 2.640 129.20 3.291 O2 [ x-1, y, z ]
rem N1-H1B 0.928 1.955 139.60 2.728 O2 [ -x+1, y-1/2, -z+1 ]
CELL 1.54178 5.2843 9.5503 6.6174 90 99.123 90
ZERR 2 0.00007 0.00013 0.00009 0 0.0004 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O
UNIT 14 22 2 4
EQIV $1 -1+X,+Y,+Z
EQIV $2 1-X,-0.5+Y,1-Z
 
L.S. 10
PLAN  5
TEMP -173
HTAB N1 O1_$1
HTAB N1 O2_$1
HTAB N1 O2_$2
HTAB
BOND $H
list 4
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\han562_w2.hkl">
REM </olex2.extras>
 
WGHT    0.049800    0.086300
FVAR       2.58481
O1    4    0.700264    0.440890    0.505261    11.00000    0.01227    0.01689 =
         0.02559    0.00230    0.00482    0.00107
O2    4    0.740712    0.671484    0.463663    11.00000    0.01386    0.01511 =
         0.04791   -0.00686    0.00964   -0.00324
N1    3    0.184662    0.440740    0.402268    11.00000    0.00975    0.01359 =
         0.02086   -0.00006    0.00420    0.00012
C1    1    0.318400    0.579612    0.421942    11.00000    0.01172    0.01282 =
         0.02034   -0.00202    0.00494   -0.00128
AFIX  13
H1    2    0.260871    0.633448    0.536076    11.00000   -1.20000
AFIX   0
C2    1    0.220737    0.653661    0.218593    11.00000    0.01700    0.01624 =
         0.02343    0.00340    0.00608    0.00387
AFIX  23
H2A   2    0.060001    0.705126    0.226599    11.00000   -1.20000
H2B   2    0.350168    0.720572    0.183571    11.00000   -1.20000
AFIX   0
C3    1    0.174073    0.536706    0.059993    11.00000    0.01884    0.02362 =
         0.02093    0.00221    0.00264    0.00434
AFIX  13
H3    2    0.035012    0.557414   -0.057222    11.00000   -1.20000
AFIX   0
C4    1    0.417098    0.467209   -0.004206    11.00000    0.02488    0.02372 =
         0.02057    0.00118    0.00832    0.00508
AFIX  23
H4A   2    0.410444    0.460189   -0.154218    11.00000   -1.20000
H4B   2    0.580217    0.510101    0.061273    11.00000   -1.20000
AFIX   0
C5    1    0.352539    0.328456    0.097097    11.00000    0.01653    0.01771 =
         0.02437   -0.00516    0.00574   -0.00049
AFIX  23
H5A   2    0.296619    0.252743   -0.002168    11.00000   -1.20000
H5B   2    0.490099    0.295394    0.205848    11.00000   -1.20000
AFIX   0
C6    1    0.129169    0.401675    0.179766    11.00000    0.01170    0.02019 =
         0.02160   -0.00395    0.00239   -0.00071
AFIX  13
H6    2   -0.042033    0.357020    0.136584    11.00000   -1.20000
AFIX   0
C7    1    0.613102    0.561990    0.467731    11.00000    0.01289    0.01748 =
         0.01810   -0.00373    0.00523   -0.00026
H1A   2    0.031912    0.448265    0.448050    11.00000    0.02508
H1B   2    0.281473    0.371134    0.475264    11.00000    0.02313
HKLF 4
 
REM  han562_a.res in P2(1)
REM R1 =  0.0286 for    1295 Fo > 4sig(Fo)  and  0.0286 for all    1296 data
REM     99 parameters refined using      1 restraints
 
END  
     
WGHT      0.0498      0.0860 

REM Instructions for potential hydrogen bonds
HTAB C2 O2_$1
HTAB C5 O1
HTAB N1 O1_$1
HTAB N1 O2_$1
HTAB N1 O2_$2

REM Highest difference peak  0.234,  deepest hole -0.140,  1-sigma level  0.037
Q1    1   0.4571  0.5690  0.4336  11.00000  0.05    0.23
Q2    1   0.1791  0.5989  0.1321  11.00000  0.05    0.17
Q3    1   0.1060  0.4764  0.1193  11.00000  0.05    0.16
Q4    1   0.8575  0.4375  0.5275  11.00000  0.05    0.16
Q5    1   0.2753  0.6206  0.3319  11.00000  0.05    0.15

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0286 for 1295 Fo > 4sig(Fo) and 0.0286 for all 13895 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.23, deepest hole -0.14
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0286
  REM R1_gt = 0.0286
  REM wR_ref = 0.0762
  REM GOOF = 1.048
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 13895
  REM Reflections_gt = 1295
  REM Parameters = n/a
  REM Hole = -0.14
  REM Peak = 0.23
  REM Flack = -0.05(12)

  
;
_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_han528
_audit_block_doi                 10.5517/ccdc.csd.cc28hf7g
_database_code_depnum_ccdc_archive 'CCDC 2100195'
loop_
_audit_author_name
_audit_author_address
'Michel Simard'
;Universite de montreal
Canada
;
_audit_update_record             
;
2021-07-29 deposited with the CCDC.	2021-11-30 downloaded from the CCDC.
;
_audit_creation_date             2017-08-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H19 N O4'
_chemical_formula_sum            'C12 H19 N O4'
_chemical_formula_weight         241.28
_chemical_absolute_configuration ad
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   6.64820(10)
_cell_length_b                   13.0584(2)
_cell_length_c                   14.8798(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1291.79(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.24
_cell_measurement_theta_min      2.97
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.768
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1109 before and 0.0347 after correction. The Ratio of minimum to maximum transmission is 0.8818. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_colour_primary    Colorless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.08
_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 Smart diffractometer equipped with an APEX II CCD Detector,
an Incoatec IMuS source and a Quazar MX mirror. 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 180.0 degree
scan in 180 frames over three different parts of the reciprocal space
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            35128
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.239
_diffrn_reflns_theta_min         6.849
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 8.3
_diffrn_detector_type            'Bruker APEX2 CCD'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Smart APEX'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Quazar MX Mirror Optics'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Microfocus Source'
_diffrn_source_target            Cu
_diffrn_source_type              'Incoatec I\mS High Brilliance Microsource'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                2502
_reflns_number_total             2502
_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) V8.34A; 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) V8.34A; 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         0.193
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.029
_refine_ls_abs_structure_details 
;
 Flack x determined using 1034 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     161
_refine_ls_number_reflns         2502
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0265
_refine_ls_restrained_S_all      1.088
_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)+(0.0388P)²+0.2431P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0689
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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 0.52582(17) 0.49787(8) 0.19395(8) 0.0248(3) Uani 1 1 d . . . . .
O2 O 0.22444(17) 0.56748(9) 0.22385(8) 0.0262(3) Uani 1 1 d . . . . .
H2 H 0.272(4) 0.620(2) 0.1981(17) 0.046(7) Uiso 1 1 d . . . . .
O3 O 0.68349(15) 0.24621(8) 0.35470(7) 0.0195(2) Uani 1 1 d . . . . .
O4 O 0.54234(15) 0.39652(8) 0.40054(7) 0.0188(2) Uani 1 1 d . . . . .
N1 N 0.41633(19) 0.31621(9) 0.28222(8) 0.0170(3) Uani 1 1 d . . . . .
C1 C 0.2695(2) 0.39754(11) 0.26955(9) 0.0180(3) Uani 1 1 d . . . . .
H1 H 0.2118 0.4173 0.3291 0.022 Uiso 1 1 calc R . . . .
C2 C 0.1047(2) 0.34577(12) 0.21207(11) 0.0243(3) Uani 1 1 d . . . . .
H2A H -0.0005 0.3152 0.2508 0.029 Uiso 1 1 calc R . . . .
H2B H 0.0411 0.3959 0.1710 0.029 Uiso 1 1 calc R . . . .
C3 C 0.2161(3) 0.26262(12) 0.15889(11) 0.0264(4) Uani 1 1 d . . . . .
H3 H 0.1295 0.2023 0.1441 0.032 Uiso 1 1 calc R . . . .
C4 C 0.3580(3) 0.29445(14) 0.08033(11) 0.0322(4) Uani 1 1 d . . . . .
H4A H 0.3290 0.2587 0.0231 0.039 Uiso 1 1 calc R . . . .
H4B H 0.3663 0.3694 0.0711 0.039 Uiso 1 1 calc R . . . .
C5 C 0.5392(3) 0.24938(13) 0.13230(10) 0.0277(4) Uani 1 1 d . . . . .
H5A H 0.5908 0.1846 0.1066 0.033 Uiso 1 1 calc R . . . .
H5B H 0.6498 0.2989 0.1420 0.033 Uiso 1 1 calc R . . . .
C6 C 0.4035(2) 0.23415(11) 0.21545(10) 0.0200(3) Uani 1 1 d . . . . .
H6 H 0.4028 0.1632 0.2407 0.024 Uiso 1 1 calc R . . . .
C7 C 0.3587(2) 0.49213(11) 0.22438(9) 0.0179(3) Uani 1 1 d . . . . .
C8 C 0.5579(2) 0.31488(10) 0.34647(9) 0.0159(3) Uani 1 1 d . . . . .
C9 C 0.6839(2) 0.41370(11) 0.47592(9) 0.0172(3) Uani 1 1 d . . . . .
C10 C 0.6064(3) 0.51300(12) 0.51600(11) 0.0267(4) Uani 1 1 d . . . . .
H10A H 0.6171 0.5678 0.4713 0.040 Uiso 1 1 calc GR . . . .
H10B H 0.6868 0.5308 0.5690 0.040 Uiso 1 1 calc GR . . . .
H10C H 0.4654 0.5045 0.5336 0.040 Uiso 1 1 calc GR . . . .
C11 C 0.8955(2) 0.42803(12) 0.43946(11) 0.0237(3) Uani 1 1 d . . . . .
H11A H 0.9430 0.3634 0.4135 0.036 Uiso 1 1 calc GR . . . .
H11B H 0.9854 0.4487 0.4884 0.036 Uiso 1 1 calc GR . . . .
H11C H 0.8946 0.4812 0.3930 0.036 Uiso 1 1 calc GR . . . .
C12 C 0.6703(2) 0.32782(12) 0.54449(10) 0.0225(3) Uani 1 1 d . . . . .
H12A H 0.5300 0.3190 0.5631 0.034 Uiso 1 1 calc GR . . . .
H12B H 0.7527 0.3450 0.5970 0.034 Uiso 1 1 calc GR . . . .
H12C H 0.7196 0.2641 0.5176 0.034 Uiso 1 1 calc GR . . . .

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 0.0264(6) 0.0183(5) 0.0298(6) -0.0006(4) 0.0099(5) -0.0030(5)
O2 0.0220(6) 0.0187(6) 0.0379(6) 0.0101(5) -0.0003(5) 0.0009(4)
O3 0.0220(5) 0.0153(5) 0.0211(5) -0.0035(4) -0.0043(4) 0.0026(4)
O4 0.0214(5) 0.0183(5) 0.0169(5) -0.0039(4) -0.0040(4) 0.0053(4)
N1 0.0207(6) 0.0151(6) 0.0153(5) 0.0012(4) -0.0012(5) 0.0000(5)
C1 0.0171(6) 0.0185(7) 0.0182(6) 0.0048(5) -0.0009(6) -0.0005(6)
C2 0.0225(7) 0.0228(7) 0.0275(8) 0.0073(6) -0.0076(7) -0.0047(6)
C3 0.0318(8) 0.0203(7) 0.0271(8) 0.0012(6) -0.0121(7) -0.0059(7)
C4 0.0523(11) 0.0258(8) 0.0185(7) -0.0008(6) -0.0063(7) -0.0017(8)
C5 0.0374(9) 0.0265(8) 0.0191(7) -0.0058(6) 0.0009(6) -0.0036(7)
C6 0.0271(7) 0.0145(6) 0.0184(7) 0.0005(5) -0.0052(6) -0.0042(6)
C7 0.0219(7) 0.0168(7) 0.0150(6) 0.0009(5) -0.0016(5) -0.0021(6)
C8 0.0182(6) 0.0142(6) 0.0153(6) 0.0012(5) 0.0010(5) -0.0015(5)
C9 0.0181(7) 0.0175(7) 0.0162(6) -0.0028(5) -0.0027(5) 0.0004(6)
C10 0.0293(8) 0.0252(8) 0.0255(8) -0.0105(6) -0.0046(7) 0.0062(7)
C11 0.0225(7) 0.0199(7) 0.0286(8) -0.0030(6) 0.0037(7) -0.0030(6)
C12 0.0247(7) 0.0246(8) 0.0182(7) 0.0007(6) -0.0014(6) -0.0010(6)

_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 C7 1.2024(19) . ?
O2 C7 1.3283(19) . ?
O3 C8 1.2312(17) . ?
O4 C8 1.3398(17) . ?
O4 C9 1.4810(17) . ?
N1 C1 1.4545(18) . ?
N1 C6 1.4639(19) . ?
N1 C8 1.3417(18) . ?
C1 C2 1.546(2) . ?
C1 C7 1.5260(19) . ?
C2 C3 1.534(2) . ?
C3 C4 1.559(2) . ?
C3 C6 1.549(2) . ?
C4 C5 1.548(2) . ?
C5 C6 1.544(2) . ?
C9 C10 1.517(2) . ?
C9 C11 1.520(2) . ?
C9 C12 1.519(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O4 C9 121.75(11) . . ?
C1 N1 C6 114.03(11) . . ?
C8 N1 C1 124.93(12) . . ?
C8 N1 C6 121.00(12) . . ?
N1 C1 C2 103.18(11) . . ?
N1 C1 C7 112.81(12) . . ?
C7 C1 C2 112.67(12) . . ?
C3 C2 C1 104.64(12) . . ?
C2 C3 C4 119.36(14) . . ?
C2 C3 C6 106.13(12) . . ?
C6 C3 C4 89.13(12) . . ?
C5 C4 C3 89.71(12) . . ?
C6 C5 C4 89.67(12) . . ?
N1 C6 C3 103.89(12) . . ?
N1 C6 C5 114.54(12) . . ?
C5 C6 C3 90.22(12) . . ?
O1 C7 O2 124.92(14) . . ?
O1 C7 C1 125.11(14) . . ?
O2 C7 C1 109.97(12) . . ?
O3 C8 O4 124.90(12) . . ?
O3 C8 N1 123.79(13) . . ?
O4 C8 N1 111.30(12) . . ?
O4 C9 C10 102.21(11) . . ?
O4 C9 C11 109.66(11) . . ?
O4 C9 C12 111.06(12) . . ?
C10 C9 C11 110.44(13) . . ?
C10 C9 C12 110.30(12) . . ?
C12 C9 C11 112.69(13) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O3 0.85(3) 1.85(3) 2.6810(15) 167(2) 3_655

_iucr_refine_instructions_details 
;

    han528.res created by SHELXL-2014/7

TITL han528_a.res in P2(1)2(1)2(1)
REM Old TITL han528 in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.102, Rweak 0.030, Alpha 0.006, Orientation as input
REM Flack x = 0.105 ( 0.023 ) from Parsons' quotients
REM Formula found by SHELXT: C12 N O4
rem O2-H2 0.849 1.847 166.69 2.681 O3 [ -x+1, y+1/2, -z+1/2 ]
CELL 1.54178 6.6482 13.0584 14.8798 90 90 90
ZERR 4 0.0001 0.0002 0.0002 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 N O
UNIT 48 76 4 16
EQIV $1 1-X,0.5+Y,0.5-Z
 
L.S. 10
PLAN  5
TEMP -173
HTAB O2 O3_$1
HTAB
list 4
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\han528_w2.hkl">
REM </olex2.extras>
 
WGHT    0.038800    0.243100
FVAR       1.95133
O1    4    0.525823    0.497867    0.193948    11.00000    0.02636    0.01833 =
         0.02979   -0.00065    0.00995   -0.00302
O2    4    0.224441    0.567481    0.223845    11.00000    0.02202    0.01868 =
         0.03787    0.01007   -0.00035    0.00086
H2    2    0.272056    0.620153    0.198129    11.00000    0.04635
O3    4    0.683494    0.246212    0.354703    11.00000    0.02196    0.01530 =
         0.02111   -0.00347   -0.00432    0.00256
O4    4    0.542343    0.396524    0.400544    11.00000    0.02140    0.01825 =
         0.01688   -0.00391   -0.00403    0.00533
N1    3    0.416329    0.316214    0.282223    11.00000    0.02069    0.01513 =
         0.01527    0.00115   -0.00125   -0.00002
C1    1    0.269542    0.397539    0.269554    11.00000    0.01712    0.01851 =
         0.01824    0.00480   -0.00086   -0.00046
AFIX  13
H1    2    0.211760    0.417276    0.329136    11.00000   -1.20000
AFIX   0
C2    1    0.104715    0.345771    0.212066    11.00000    0.02254    0.02279 =
         0.02752    0.00731   -0.00756   -0.00471
AFIX  23
H2A   2   -0.000495    0.315191    0.250754    11.00000   -1.20000
H2B   2    0.041099    0.395861    0.171000    11.00000   -1.20000
AFIX   0
C3    1    0.216099    0.262621    0.158888    11.00000    0.03185    0.02030 =
         0.02711    0.00122   -0.01208   -0.00586
AFIX  13
H3    2    0.129549    0.202299    0.144098    11.00000   -1.20000
AFIX   0
C4    1    0.357995    0.294452    0.080326    11.00000    0.05233    0.02575 =
         0.01845   -0.00080   -0.00631   -0.00171
AFIX  23
H4A   2    0.329047    0.258713    0.023092    11.00000   -1.20000
H4B   2    0.366333    0.369409    0.071079    11.00000   -1.20000
AFIX   0
C5    1    0.539218    0.249378    0.132296    11.00000    0.03743    0.02652 =
         0.01912   -0.00583    0.00085   -0.00363
AFIX  23
H5A   2    0.590839    0.184573    0.106601    11.00000   -1.20000
H5B   2    0.649802    0.298946    0.141953    11.00000   -1.20000
AFIX   0
C6    1    0.403455    0.234148    0.215447    11.00000    0.02710    0.01454 =
         0.01845    0.00055   -0.00515   -0.00418
AFIX  13
H6    2    0.402780    0.163192    0.240723    11.00000   -1.20000
AFIX   0
C7    1    0.358652    0.492134    0.224382    11.00000    0.02189    0.01685 =
         0.01504    0.00087   -0.00158   -0.00212
C8    1    0.557922    0.314876    0.346467    11.00000    0.01823    0.01419 =
         0.01529    0.00116    0.00096   -0.00154
C9    1    0.683861    0.413697    0.475922    11.00000    0.01809    0.01747 =
         0.01617   -0.00282   -0.00275    0.00040
C10   1    0.606427    0.512996    0.515996    11.00000    0.02933    0.02518 =
         0.02546   -0.01054   -0.00459    0.00617
AFIX 137
H10A  2    0.617117    0.567847    0.471301    11.00000   -1.50000
H10B  2    0.686785    0.530752    0.568966    11.00000   -1.50000
H10C  2    0.465363    0.504526    0.533606    11.00000   -1.50000
AFIX   0
C11   1    0.895512    0.428031    0.439455    11.00000    0.02245    0.01992 =
         0.02865   -0.00298    0.00373   -0.00297
AFIX 137
H11A  2    0.943050    0.363444    0.413497    11.00000   -1.50000
H11B  2    0.985413    0.448711    0.488393    11.00000   -1.50000
H11C  2    0.894561    0.481181    0.392960    11.00000   -1.50000
AFIX   0
C12   1    0.670323    0.327821    0.544487    11.00000    0.02470    0.02455 =
         0.01816    0.00065   -0.00137   -0.00095
AFIX 137
H12A  2    0.530000    0.318981    0.563109    11.00000   -1.50000
H12B  2    0.752668    0.345006    0.596991    11.00000   -1.50000
H12C  2    0.719565    0.264061    0.517604    11.00000   -1.50000
AFIX   0
HKLF 4
 
REM  han528_a.res in P2(1)2(1)2(1)
REM R1 =  0.0265 for    2502 Fo > 4sig(Fo)  and  0.0265 for all    2502 data
REM    161 parameters refined using      0 restraints
 
END  
     
WGHT      0.0388      0.2424 

REM Instructions for potential hydrogen bonds
HTAB O2 O3_$1
EQIV $2 -x+1, y-1/2, -z+1/2
HTAB C6 O1_$2
HTAB C11 O3
HTAB C12 O3

REM Highest difference peak  0.193,  deepest hole -0.116,  1-sigma level  0.029
Q1    1   0.7929  0.4193  0.4558  11.00000  0.05    0.19
Q2    1   0.6524  0.4619  0.4988  11.00000  0.05    0.19
Q3    1   0.2948  0.2410  0.1988  11.00000  0.05    0.18
Q4    1   0.6880  0.3650  0.5074  11.00000  0.05    0.17
Q5    1   0.4919  0.2390  0.1800  11.00000  0.05    0.17

  REM The information below was added by Olex2.
  REM
  REM R1 = 0.0265 for 2502 Fo > 4sig(Fo) and 0.0265 for all 35278 data
  REM n/a parameters refined using n/a restraints
  REM Highest difference peak 0.19, deepest hole -0.12
  REM Mean Shift 0, Max Shift 0.000.

  REM +++ Tabular Listing of Refinement Information +++
  REM R1_all = 0.0265
  REM R1_gt = 0.0265
  REM wR_ref = 0.0689
  REM GOOF = 1.088
  REM Shift_max = 0.000
  REM Shift_mean = 0
  REM Reflections_all = 35278
  REM Reflections_gt = 2502
  REM Parameters = n/a
  REM Hole = -0.12
  REM Peak = 0.19
  REM Flack = 0.06(3)

  
;
_olex2_submission_special_instructions 'No special instructions were received'
