# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2018

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1847372'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;
_audit_creation_method           'MoPro v16                '
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H4 N2 O4'
_chemical_formula_weight         168.11
_chemical_absolute_configuration .

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
H H 0.0000 0.0000
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
N N 0.0061 0.0033
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
O O 0.0106 0.0060
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'

loop_
_symmetry_equiv_pos_as_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                   5.6628
_cell_length_b                   5.3723
_cell_length_c                   10.91430(10)
_cell_angle_alpha                90.
_cell_angle_beta                 92.0210(10)
_cell_angle_gamma                90.
_cell_volume                     331.831(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    53740
_cell_measurement_theta_min      3.5890
_cell_measurement_theta_max      65.1240

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_F_000             172
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      90(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_power             50
_diffrn_source_current           24
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            69397
_diffrn_reflns_av_unetI/netI     0.0056
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.00762
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.74
_diffrn_reflns_theta_max         55.52
_reflns_number_total             4276
_reflns_number_gt                4077
_reflns_threshold_expression     >2.0sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refinement of F² against reflections.
 The threshold expression of F² > 2sigma(F²) is
 used for calculating R-factors(gt) and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'calc w =1/[5.*σ²(Fo²)]'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
# refall refxyz hetero heteroxyz constr 

_refine_ls_extinction_method     'Isotropic Gaussian'
_refine_ls_extinction_coef       0.02818
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?
###  Notice MoPro refines Rogers parameter (Eta f" multiplier)

_refine_ls_number_reflns         4276
_refine_ls_number_parameters     207
_refine_ls_number_restraints     80
# R-factors: R(F)  &  wR2(I) 
_refine_ls_R_factor_all          0.0115
_refine_ls_R_factor_gt           0.0107
_refine_ls_wR_factor_ref         0.0244
_refine_ls_wR_factor_gt          0.0241
_refine_ls_goodness_of_fit_ref   0.928
# GOF(I) computed assuming  all parameters refined:     248
_refine_ls_restrained_S_all      1.517
_refine_ls_shift/su_max          0.066
_refine_ls_shift/su_mean         0.003

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        55.52
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_diff_density_rms         ?
###  to get diff_density_max min & rms : 
###  run MoPro  : WRIT FOUR   to create FOURier file 
### run VMoPro : FOUR  FastFourierTransform  
### to get a 3D grid (Xplor format) on whole unit-cell
###  To get max min rms statistics
###  run VMoPro: GRID STAT   or 
###  open 3D xplor grid with MoProViewer 

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.689166(15) 0.105238(14) 0.143458(7) 0.013470(14) Uani 1 d . . . .
O O1 0.56523(5) 0.01475(4) 0.22193(3) 0.019776(19) Uani 1 d . . . .
O O2 0.88950(6) 0.03465(6) 0.123100(17) 0.02020(2) Uani 1 d . . . .
C C1 0.590366(13) 0.310342(15) 0.068668(7) 0.011639(14) Uani 1 d . . . .
C C2 0.379755(14) 0.417781(17) 0.103307(8) 0.013592(16) Uani 1 d . . . .
C C3 0.712987(14) 0.387186(17) -0.032910(8) 0.013487(15) Uani 1 d . . . .
H H2 0.2930(5) 0.3515(6) 0.18321(19) 0.0297(12) Uani 1 d D . . .
H H3 0.8751(3) 0.2970(5) -0.0563(3) 0.0276(12) Uani 1 d D . . .


_geom_special_details            
;                                    
;

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
N1 O2 1.2239(3) . ?
N1 O1 1.2267(3) . ?
N1 C1 1.47012(11) . ?
C1 C2 1.38935(11) . ?
C1 C3 1.39140(12) . ?
C2 C3 1.39123(12) 3_665 ?
C2 H2 1.0765(10) . ?
C3 C2 1.39123(12) 3_665 ?
C3 H3 1.0768(10) . ?

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 N1 O1 124.11(2) . . . ?
O2 N1 C1 117.935(14) . . . ?
O1 N1 C1 117.956(13) . . . ?
N1 C1 C2 118.283(6) . . . ?
N1 C1 C3 118.291(7) . . . ?
C2 C1 C3 123.425(7) . . . ?
C1 C2 C3 118.265(7) . . 3_665 ?
C1 C2 H2 120.23(16) . . . ?
C3 C2 H2 121.51(16) 3_665 . . ?
C1 C3 C2 118.309(7) . . 3_665 ?
C1 C3 H3 120.60(16) . . . ?
C2 C3 H3 121.09(16) 3_665 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C1 C2 H2 . . . . 0.2(2) ?
N1 C1 C3 H3 . . . . 0.6(2) ?
O1 N1 C1 C2 . . . . 10.34(3) ?
O1 N1 C1 C3 . . . . -169.83(3) ?
O2 N1 C1 C2 . . . . -170.01(3) ?
O2 N1 C1 C3 . . . . 9.81(3) ?
C2 C1 C3 H3 . . . . -179.6(2) ?
C3 C1 C2 H2 . . . . -179.6(2) ?

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
### Notice sigmas on distances involving HYDROGEN atoms 
### is generally not recommended.
### this may cause reading errors in checkcif
C2 H2 O1 1.0765(10) 2.471(3) 3.2555(3) 128.80(15) 2
C3 H3 O2 1.0768(10) 2.3562(17) 3.3657(3) 155.49(12) 3_755
####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1847374'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;
_audit_creation_method           'MoPro v16                '
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H7 B Cl N O2'
_chemical_formula_weight         159.38
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1507 0.1611 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0014 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_space_group_IT_number           7
_symmetry_space_group_name_H-M   Pc
_space_group_name_Hall           'P -2yc'

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

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

_cell_length_a                   6.20620(5)
_cell_length_b                   5.25334(4)
_cell_length_c                   11.18373(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.5034(8)
_cell_angle_gamma                90
_cell_volume                     351.359(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    25830
_cell_measurement_theta_min      3.3830
_cell_measurement_theta_max      65.0110

_exptl_crystal_description       colourless
_exptl_crystal_colour            block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             164
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.467
_shelx_estimated_absorpt_T_min   0.873
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.686
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_power             50
_diffrn_source_current           24
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            31805
_diffrn_reflns_av_unetI/netI     0.0090
_diffrn_reflns_av_R_equivalents  0.0121
_diffrn_reflns_av_sigmaI/netI    0.00878
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.41
_diffrn_reflns_theta_max         58.52
_reflns_number_total             7501
_reflns_number_gt                7480
_reflns_threshold_expression     >2.0sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refinement of F² against reflections.
 The threshold expression of F² > 2sigma(F²) is
 used for calculating R-factors(gt) and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'calc w =1/[2.25*σ²(Fo²)]'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
# refall refxyz hetero heteroxyz constr 

_refine_ls_extinction_method     'Isotropic Gaussian'
_refine_ls_extinction_coef       0.06130

_refine_ls_abs_structure_details 'Rogers (1981),  2660 Friedel pairs'
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  1.
###  Notice MoPro refines Rogers parameter (Eta f" multiplier)

_refine_ls_number_reflns         7501
_refine_ls_number_parameters     334
_refine_ls_number_restraints     154
# R-factors: R(F)  &  wR2(I) 
_refine_ls_R_factor_all          0.0063
_refine_ls_R_factor_gt           0.0063
_refine_ls_wR_factor_ref         0.0139
_refine_ls_wR_factor_gt          0.0139
_refine_ls_goodness_of_fit_ref   0.989
# GOF(I) computed assuming  all parameters refined:     462
_refine_ls_restrained_S_all      127.046
_refine_ls_shift/su_max          -0.088
_refine_ls_shift/su_mean         -0.001

_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_diff_density_rms         ?
###  to get diff_density_max min & rms : 
###  run MoPro  : WRIT FOUR   to create FOURier file 
### run VMoPro : FOUR  FastFourierTransform  
### to get a 3D grid (Xplor format) on whole unit-cell
###  To get max min rms statistics
###  run VMoPro: GRID STAT   or 
###  open 3D xplor grid with MoProViewer 

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl CL1 0.0654(6) -0.325320(6) 0.3141(3) 0.010959(10) Uani 1 d . . . .
O O1 0.9643(6) 0.80657(5) 0.5623(3) 0.014864(17) Uani 1 d . . . .
O O2 0.7452(6) 0.87904(2) 0.7017(3) 0.012663(14) Uani 1 d . . . .
N N1 0.3339(6) 0.118455(16) 0.4649(3) 0.011637(12) Uani 1 d . . . .
C C1 0.6265(6) 0.510485(16) 0.5557(3) 0.009835(12) Uani 1 d . . . .
C C2 0.4540(6) 0.448015(18) 0.6098(3) 0.011445(13) Uani 1 d . . . .
C C3 0.3089(6) 0.249901(18) 0.5633(3) 0.012333(13) Uani 1 d . . . .
C C4 0.4946(6) 0.171341(18) 0.4089(3) 0.012453(14) Uani 1 d . . . .
C C5 0.6443(6) 0.36667(2) 0.4531(3) 0.011797(13) Uani 1 d . . . .
B B1 0.7919(6) 0.73980(2) 0.6097(3) 0.010610(15) Uani 1 d . . . .
H H1 0.2242(9) -0.0284(8) 0.4304(5) 0.02339 Uani 1 d D U . .
H H2 0.4356(8) 0.5540(8) 0.6902(5) 0.02805 Uani 1 d D U . .
H H3 0.1749(9) 0.2018(9) 0.6053(5) 0.02857 Uani 1 d D U . .
H H4 0.5072(9) 0.0595(8) 0.3290(5) 0.02803 Uani 1 d D U . .
H H5 0.7739(8) 0.4102(8) 0.4071(5) 0.03019 Uani 1 d D U . .
H H1O 0.9779(12) 0.7180(12) 0.4863(6) 0.02920 Uani 1 d D U . .
H H2O 0.8506(11) 1.0198(10) 0.7300(6) 0.02273 Uani 1 d D U . .


_geom_special_details            
;                                    
;

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 B1 1.3611(3) . ?
O1 H1O 0.991(5) . ?
O2 B1 1.35593(16) . ?
O2 H2O 0.982(5) . ?
N1 C4 1.34164(13) . ?
N1 C3 1.34250(14) . ?
N1 H1 1.033(2) . ?
C1 C2 1.40240(11) . ?
C1 C5 1.40265(14) . ?
C1 B1 1.59341(13) . ?
C2 C3 1.38366(12) . ?
C2 H2 1.089(2) . ?
C3 H3 1.089(2) . ?
C4 C5 1.38362(12) . ?
C4 H4 1.089(2) . ?
C5 H5 1.088(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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
B1 O1 H1O 117.9(3) . . . ?
B1 O2 H2O 113.0(3) . . . ?
C4 N1 C3 122.655(8) . . . ?
C4 N1 H1 118.54(10) . . . ?
C3 N1 H1 118.81(10) . . . ?
C2 C1 C5 117.590(7) . . . ?
C2 C1 B1 120.160(7) . . . ?
C5 C1 B1 122.246(7) . . . ?
C3 C2 C1 120.573(7) . . . ?
C3 C2 H2 119.61(10) . . . ?
C1 C2 H2 119.81(10) . . . ?
N1 C3 C2 119.290(8) . . . ?
N1 C3 H3 120.21(10) . . . ?
C2 C3 H3 120.49(10) . . . ?
N1 C4 C5 119.883(7) . . . ?
N1 C4 H4 119.76(10) . . . ?
C5 C4 H4 120.36(10) . . . ?
C4 C5 C1 120.005(8) . . . ?
C4 C5 H5 119.79(10) . . . ?
C1 C5 H5 120.19(10) . . . ?
O2 B1 O1 120.465(13) . . . ?
O2 B1 C1 116.645(8) . . . ?
O1 B1 C1 122.765(12) . . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 B1 O2 H2O . . . . -2.7(7) ?
O1 B1 C1 C2 . . . . 179.0(6) ?
O1 B1 C1 C5 . . . . -1.8(6) ?
O2 B1 O1 H1O . . . . -170.2(8) ?
O2 B1 C1 C2 . . . . -5.1(6) ?
O2 B1 C1 C5 . . . . 174.1(6) ?
N1 C4 C5 C1 . . . . -0.6(5) ?
N1 C4 C5 H5 . . . . -179.6(7) ?
N1 C3 C2 C1 . . . . -0.4(5) ?
N1 C3 C2 H2 . . . . -179.3(7) ?
C1 C2 C3 H3 . . . . -179.9(8) ?
C1 C5 C4 H4 . . . . 179.8(7) ?
C1 B1 O2 H2O . . . . -178.7(7) ?
C1 B1 O1 H1O . . . . 5.6(8) ?
C2 C3 N1 C4 . . . . -0.2(6) ?
C2 C3 N1 H1 . . . . -179.6(7) ?
C2 C1 C5 C4 . . . . 0.0(6) ?
C2 C1 C5 H5 . . . . 179.0(7) ?
C3 N1 C4 C5 . . . . 0.7(5) ?
C3 N1 C4 H4 . . . . -179.7(7) ?
C3 C2 C1 C5 . . . . 0.5(5) ?
C3 C2 C1 B1 . . . . 179.7(5) ?
C4 N1 C3 H3 . . . . 179.3(7) ?
C4 C5 C1 B1 . . . . -179.2(6) ?
C5 C4 N1 H1 . . . . -179.9(7) ?
C5 C1 C2 H2 . . . . 179.4(7) ?
B1 C1 C2 H2 . . . . -1.4(7) ?
B1 C1 C5 H5 . . . . -0.2(7) ?
H1 N1 C4 H4 . . . . -0.2(8) ?
H1 N1 C3 H3 . . . . -0.1(9) ?
H2 C2 C3 H3 . . . . 1.2(9) ?
H4 C4 C5 H5 . . . . 0.8(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
### Notice sigmas on distances involving HYDROGEN atoms 
### is generally not recommended.
### this may cause reading errors in checkcif
N1 H1 O1 1.033(2) 2.608(2) 3.2350(3) 118.81(13) 1_445
C3 H3 O1 1.089(2) 2.432(2) 3.1598(3) 123.01(13) 1_445
N1 H1 CL1 1.033(2) 2.100(2) 3.09102(9) 159.99(6) 1
O1 H1O C5 0.991(5) 2.724(6) 3.0789(2) 101.5(4) 1
C3 H3 CL1 1.089(2) 2.680(2) 3.54605(11) 136.11(12) 2
C4 H4 O2 1.089(2) 2.331(2) 3.12699(17) 128.42(11) 2_564
O1 H1O CL1 0.991(5) 2.149(5) 3.0834(3) 156.5(3) 1_665
O2 H2O CL1 0.982(5) 2.137(5) 3.11272(10) 172.21(9) 2_665
####################################################################### 
# 
# 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_I_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1847373'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;
_audit_creation_method           'MoPro v16                '
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N2 O8'
_chemical_formula_weight         338.27
_chemical_absolute_configuration ad

_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_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
H H 0.0000 0.0000
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
N N 0.0061 0.0033
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'
O O 0.0106 0.0060
'Clementi & Roetti 1974. Atomic Data & Nuclear Data Tables. 14, 177'

loop_
_symmetry_equiv_pos_as_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                   4.54400(10)
_cell_length_b                   15.2652(2)
_cell_length_c                   20.3342(2)
_cell_angle_alpha                90.
_cell_angle_beta                 90.
_cell_angle_gamma                90.
_cell_volume                     1410.48(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    28381
_cell_measurement_theta_min      2.0070
_cell_measurement_theta_max      57.7740

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      90(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_power             50
_diffrn_source_current           24
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            89157
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.02355
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         57.00
_reflns_number_total             18682
_reflns_number_gt                17264
_reflns_threshold_expression     >2.0sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refinement of F² against reflections.
 The threshold expression of F² > 2sigma(F²) is
 used for calculating R-factors(gt) and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'calc w =1/[1.15*σ²(Fo²)]'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
# refall refxyz hetero heteroxyz constr 

_refine_ls_extinction_method     none

_refine_ls_abs_structure_details 'Rogers (1981),  8135 Friedel pairs'
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  1.
###  Notice MoPro refines Rogers parameter (Eta f" multiplier)

_refine_ls_number_reflns         18682
_refine_ls_number_parameters     747
_refine_ls_number_restraints     361
# R-factors: R(F)  &  wR2(I) 
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0181
_refine_ls_wR_factor_ref         0.0307
_refine_ls_wR_factor_gt          0.0300
_refine_ls_goodness_of_fit_ref   1.036
# GOF(I) computed assuming  all parameters refined:    1022
_refine_ls_restrained_S_all      260.020
_refine_ls_shift/su_max          -0.062
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        26.60
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_diff_density_rms         ?
###  to get diff_density_max min & rms : 
###  run MoPro  : WRIT FOUR   to create FOURier file 
### run VMoPro : FOUR  FastFourierTransform  
### to get a 3D grid (Xplor format) on whole unit-cell
###  To get max min rms statistics
###  run VMoPro: GRID STAT   or 
###  open 3D xplor grid with MoProViewer 

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 -0.02040(5) 0.182806(13) 0.654575(10) 0.01268(3) Uani 1 d . . . .
H H1A 0.6638(18) 0.7650(4) 0.7404(3) 0.02895 Uani 1 d D U . .
H H1 -0.1584(14) 0.2322(4) 0.6584(4) 0.02325 Uani 1 d D U . .
C C1 0.13709(4) 0.188477(9) 0.600791(7) 0.00985(3) Uani 1 d . . . .
O O2 0.12508(5) 0.246991(13) 0.560271(9) 0.01343(3) Uani 1 d . . . .
H H2A 0.3234(17) 0.6375(5) 0.7530(2) 0.02800 Uani 1 d D U . .
H H2 0.4721(12) 0.1067(4) 0.6390(2) 0.02332 Uani 1 d D U . .
C C2 0.34866(4) 0.111926(9) 0.592907(7) 0.00952(3) Uani 1 d . . . .
O O3 0.54064(4) 0.126417(11) 0.539684(8) 0.01239(3) Uani 1 d . . . .
H H3O 0.5007(17) 0.1832(3) 0.5195(3) 0.02282 Uani 1 d D U . .
H H3 0.0357(11) 0.0165(4) 0.6252(2) 0.02311 Uani 1 d D U . .
C C3 0.17797(4) 0.025683(10) 0.582248(7) 0.00942(3) Uani 1 d . . . .
C C4 0.39033(4) -0.051845(9) 0.581337(7) 0.00965(3) Uani 1 d . . . .
H H4A 0.4128(17) 0.5942(4) 0.5439(2) 0.02624 Uani 1 d D U . .
H H4 -0.1496(11) 0.0649(4) 0.5285(3) 0.02299 Uani 1 d D U . .
O O4 0.02028(4) 0.026266(11) 0.522997(8) 0.01217(3) Uani 1 d . . . .
O O6 0.41451(4) -0.101994(12) 0.535519(9) 0.01308(3) Uani 1 d . . . .
O O5 0.54305(5) -0.057067(12) 0.636683(10) 0.01259(3) Uani 1 d . . . .
H H5A 0.7423(16) 0.7248(4) 0.5408(2) 0.02788 Uani 1 d D U . .
H H5O 0.6827(14) -0.1059(4) 0.6343(4) 0.02342 Uani 1 d D U . .
O O2A -0.36830(4) 0.305876(12) 0.673128(8) 0.01393(3) Uani 1 d . . . .
C C3A 0.33740(4) 0.603305(11) 0.649598(7) 0.01159(3) Uani 1 d . . . .
C C4A 0.45491(5) 0.629687(11) 0.589020(8) 0.01362(4) Uani 1 d . . . .
C C5A 0.64146(5) 0.701259(11) 0.585677(8) 0.01369(4) Uani 1 d . . . .
C C6A 0.14733(4) 0.525321(11) 0.655918(7) 0.01136(3) Uani 1 d . . . .
C C7A 0.11746(5) 0.481540(13) 0.716258(8) 0.01473(4) Uani 1 d . . . .
C C8A -0.06000(5) 0.408366(13) 0.721427(8) 0.01451(4) Uani 1 d . . . .
C C9A -0.18333(4) 0.418345(12) 0.609213(8) 0.01281(4) Uani 1 d . . . .
C C10A -0.00862(4) 0.491942(11) 0.602157(8) 0.01266(4) Uani 1 d . . . .
C C2A 0.41147(5) 0.653107(14) 0.704931(8) 0.01652(4) Uani 1 d . . . .
N N2A -0.20523(4) 0.378027(10) 0.667964(7) 0.01147(3) Uani 1 d . . . .
O O1A 0.89285(4) 0.814531(11) 0.636890(8) 0.01390(3) Uani 1 d . . . .
H H10A -0.0012(16) 0.5232(4) 0.55448(19) 0.02585 Uani 1 d D U . .
H H9A -0.3087(14) 0.3888(4) 0.5698(3) 0.02657 Uani 1 d D U . .
H H8A -0.0880(18) 0.3712(4) 0.7663(2) 0.02859 Uani 1 d D U . .
H H7A 0.2360(16) 0.5020(5) 0.7598(2) 0.02808 Uani 1 d D U . .
C C1A 0.59882(5) 0.723815(14) 0.699555(9) 0.01670(4) Uani 1 d . . . .
N N1A 0.71259(4) 0.746403(10) 0.640628(7) 0.01164(3) Uani 1 d . . . .


_geom_special_details            
;                                    
;

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 1.3098(3) . ?
O1 H1 0.983(3) . ?
H1A C1A 1.084(3) . ?
C1 O2 1.2164(3) . ?
C1 C2 1.5217(2) . ?
H2A C2A 1.082(3) . ?
H2 C2 1.095(3) . ?
C2 O3 1.4076(2) . ?
C2 C3 1.5433(2) . ?
O3 H3O 0.976(3) . ?
H3 C3 1.096(3) . ?
C3 O4 1.4018(2) . ?
C3 C4 1.5271(2) . ?
C4 O5 1.3246(2) . ?
C4 O6 1.2109(2) . ?
H4A C4A 1.082(3) . ?
H4 O4 0.978(3) . ?
O5 H5O 0.980(3) . ?
H5A C5A 1.082(3) . ?
O2A N2A 1.3316(3) . ?
C3A C6A 1.4764(3) . ?
C3A C2A 1.3990(2) . ?
C3A C4A 1.4017(2) . ?
C4A C5A 1.3845(3) . ?
C5A N1A 1.3520(2) . ?
C6A C10A 1.3989(2) . ?
C6A C7A 1.4037(2) . ?
C7A C8A 1.3817(3) . ?
C7A H7A 1.083(3) . ?
C8A N2A 1.3535(2) . ?
C8A H8A 1.082(3) . ?
C9A N2A 1.3476(2) . ?
C9A C10A 1.3831(3) . ?
C9A H9A 1.082(3) . ?
C10A H10A 1.081(3) . ?
C2A C1A 1.3790(3) . ?
O1A N1A 1.3260(3) . ?
C1A N1A 1.3498(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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 111.3(4) . . . ?
O1 C1 O2 126.127(16) . . . ?
O1 C1 C2 112.481(14) . . . ?
O2 C1 C2 121.391(14) . . . ?
O3 C2 C1 110.603(12) . . . ?
O3 C2 C3 109.728(12) . . . ?
O3 C2 H2 110.6(3) . . . ?
C1 C2 C3 110.633(11) . . . ?
C1 C2 H2 106.8(3) . . . ?
C3 C2 H2 108.3(3) . . . ?
C2 O3 H3O 110.3(4) . . . ?
O4 C3 C4 108.510(12) . . . ?
O4 C3 C2 111.850(12) . . . ?
O4 C3 H3 112.6(3) . . . ?
C4 C3 C2 110.196(11) . . . ?
C4 C3 H3 106.4(3) . . . ?
C2 C3 H3 107.1(3) . . . ?
O5 C4 O6 124.621(16) . . . ?
O5 C4 C3 111.555(14) . . . ?
O6 C4 C3 123.824(14) . . . ?
C3 O4 H4 108.0(4) . . . ?
C4 O5 H5O 110.0(4) . . . ?
C6A C3A C2A 120.591(14) . . . ?
C6A C3A C4A 122.075(14) . . . ?
C2A C3A C4A 117.324(13) . . . ?
C5A C4A C3A 120.206(14) . . . ?
C5A C4A H4A 117.5(3) . . . ?
C3A C4A H4A 122.3(3) . . . ?
N1A C5A C4A 120.532(15) . . . ?
N1A C5A H5A 115.2(4) . . . ?
C4A C5A H5A 124.2(3) . . . ?
C3A C6A C10A 121.470(14) . . . ?
C3A C6A C7A 121.101(14) . . . ?
C10A C6A C7A 117.428(13) . . . ?
C8A C7A C6A 120.520(14) . . . ?
C8A C7A H7A 117.5(4) . . . ?
C6A C7A H7A 122.0(3) . . . ?
N2A C8A C7A 120.006(16) . . . ?
N2A C8A H8A 116.1(4) . . . ?
C7A C8A H8A 123.9(4) . . . ?
N2A C9A C10A 120.355(14) . . . ?
N2A C9A H9A 115.3(4) . . . ?
C10A C9A H9A 124.4(3) . . . ?
C9A C10A C6A 120.369(14) . . . ?
C9A C10A H10A 118.0(3) . . . ?
C6A C10A H10A 121.6(3) . . . ?
C1A C2A C3A 120.670(15) . . . ?
C1A C2A H2A 118.2(3) . . . ?
C3A C2A H2A 121.1(3) . . . ?
O2A N2A C9A 119.260(14) . . . ?
O2A N2A C8A 119.407(15) . . . ?
C9A N2A C8A 121.318(14) . . . ?
N1A C1A C2A 120.449(16) . . . ?
N1A C1A H1A 115.4(4) . . . ?
C2A C1A H1A 124.2(3) . . . ?
O1A N1A C1A 119.199(15) . . . ?
O1A N1A C5A 120.004(15) . . . ?
C1A N1A C5A 120.790(14) . . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 O3 . . . . -171.97(3) ?
O1 C1 C2 C3 . . . . 66.24(2) ?
O1 C1 C2 H2 . . . . -51.5(3) ?
H1A C1A N1A O1A . . . . 0.8(7) ?
H1A C1A N1A C5A . . . . -178.3(7) ?
H1A C1A C2A C3A . . . . 179.7(7) ?
H1A C1A C2A H2A . . . . -0.1(9) ?
H1 O1 C1 O2 . . . . 1.4(7) ?
H1 O1 C1 C2 . . . . -178.9(6) ?
C1 C2 O3 H3O . . . . 1.3(5) ?
C1 C2 C3 O4 . . . . 64.90(2) ?
C1 C2 C3 C4 . . . . -174.30(2) ?
C1 C2 C3 H3 . . . . -58.9(2) ?
O2 C1 C2 O3 . . . . 7.77(3) ?
O2 C1 C2 C3 . . . . -114.02(2) ?
O2 C1 C2 H2 . . . . 128.2(3) ?
H2A C2A C1A N1A . . . . -179.5(7) ?
H2A C2A C3A C6A . . . . -2.9(7) ?
H2A C2A C3A C4A . . . . 178.2(7) ?
H2 C2 O3 H3O . . . . -116.9(6) ?
H2 C2 C3 O4 . . . . -178.3(6) ?
H2 C2 C3 C4 . . . . -57.5(6) ?
H2 C2 C3 H3 . . . . 57.9(6) ?
C2 C3 O4 H4 . . . . -73.6(3) ?
C2 C3 C4 O5 . . . . 58.34(2) ?
C2 C3 C4 O6 . . . . -121.69(3) ?
O3 C2 C3 O4 . . . . -57.40(2) ?
O3 C2 C3 C4 . . . . 63.39(2) ?
O3 C2 C3 H3 . . . . 178.8(3) ?
H3O O3 C2 C3 . . . . 123.6(6) ?
H3 C3 O4 H4 . . . . 47.1(6) ?
H3 C3 C4 O5 . . . . -57.4(5) ?
H3 C3 C4 O6 . . . . 122.5(6) ?
C3 C4 O5 H5O . . . . -177.9(5) ?
C4 C3 O4 H4 . . . . 164.6(4) ?
H4A C4A C5A N1A . . . . -177.4(7) ?
H4A C4A C5A H5A . . . . 1.7(9) ?
H4A C4A C3A C6A . . . . -0.1(7) ?
H4A C4A C3A C2A . . . . 178.7(7) ?
O4 C3 C4 O5 . . . . -178.88(2) ?
O4 C3 C4 O6 . . . . 1.08(3) ?
O6 C4 O5 H5O . . . . 2.1(6) ?
H5A C5A N1A O1A . . . . 0.4(7) ?
H5A C5A N1A C1A . . . . 179.4(7) ?
H5A C5A C4A C3A . . . . 179.2(7) ?
O2A N2A C9A C10A . . . . -178.15(2) ?
O2A N2A C9A H9A . . . . 1.5(5) ?
O2A N2A C8A C7A . . . . 177.93(3) ?
O2A N2A C8A H8A . . . . -0.4(5) ?
C3A C6A C10A C9A . . . . 179.45(3) ?
C3A C6A C10A H10A . . . . -2.0(5) ?
C3A C6A C7A C8A . . . . -179.67(3) ?
C3A C6A C7A H7A . . . . -1.6(6) ?
C3A C2A C1A N1A . . . . 0.37(3) ?
C3A C4A C5A N1A . . . . 0.06(3) ?
C4A C5A N1A O1A . . . . 179.60(3) ?
C4A C5A N1A C1A . . . . -1.36(3) ?
C4A C3A C6A C10A . . . . -22.78(3) ?
C4A C3A C6A C7A . . . . 156.92(3) ?
C4A C3A C2A C1A . . . . -1.59(3) ?
C5A N1A C1A C2A . . . . 1.15(3) ?
C5A C4A C3A C6A . . . . -177.48(3) ?
C5A C4A C3A C2A . . . . 1.38(3) ?
C6A C3A C2A C1A . . . . 177.29(3) ?
C6A C10A C9A N2A . . . . 0.00(3) ?
C6A C10A C9A H9A . . . . -179.6(5) ?
C6A C7A C8A N2A . . . . 0.43(3) ?
C6A C7A C8A H8A . . . . 178.7(5) ?
C7A C8A N2A C9A . . . . -0.68(3) ?
C7A C6A C3A C2A . . . . -21.91(3) ?
C7A C6A C10A C9A . . . . -0.25(3) ?
C7A C6A C10A H10A . . . . 178.3(5) ?
C8A N2A C9A C10A . . . . 0.45(3) ?
C8A N2A C9A H9A . . . . -179.9(5) ?
C8A C7A C6A C10A . . . . 0.03(3) ?
C9A N2A C8A H8A . . . . -179.1(5) ?
C10A C6A C3A C2A . . . . 158.40(3) ?
C10A C6A C7A H7A . . . . 178.1(5) ?
C2A C1A N1A O1A . . . . -179.80(3) ?
N2A C9A C10A H10A . . . . -178.6(5) ?
N2A C8A C7A H7A . . . . -177.7(5) ?
H10A C10A C9A H9A . . . . 1.8(8) ?
H8A C8A C7A H7A . . . . 0.5(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
### Notice sigmas on distances involving HYDROGEN atoms 
### is generally not recommended.
### this may cause reading errors in checkcif
C3 H3 O5 1.096(3) 2.515(5) 3.3383(3) 131.0(3) 1_455
O4 H4 O3 0.978(3) 1.707(3) 2.6837(2) 176.16(7) 1_455
C10A H10A O6 1.081(3) 2.224(3) 3.2835(2) 166.31(17) 4_456
C9A H9A O4 1.082(3) 2.418(6) 3.1235(2) 121.6(3) 4_456
O5 H5O O1A 0.980(3) 1.546(3) 2.5236(3) 174.65(12) 1_545
O5 H5O N1A 0.980(3) 2.262(5) 3.0984(2) 142.5(3) 1_545
O1 H1 O2A 0.983(3) 1.505(3) 2.4841(3) 172.98(16) 1
O1 H1 N2A 0.983(3) 2.245(5) 3.1081(2) 145.8(3) 1
O3 H3O O2 0.976(3) 2.132(7) 2.6700(3) 113.0(4) 1
C1A H1A O2A 1.084(3) 2.298(7) 3.0608(3) 125.8(4) 3_556
C2A H2A O1 1.082(3) 2.431(5) 3.3948(3) 147.6(3) 3_556
O3 H3O O2 0.976(3) 2.022(5) 2.8307(3) 138.8(3) 4_556
C4A H4A O4 1.082(3) 2.340(5) 3.3082(2) 148.1(3) 4_556
C5A H5A O6 1.082(3) 2.556(7) 3.1478(3) 113.5(4) 4_556
C8A H8A O1A 1.082(3) 2.326(5) 3.3059(2) 149.7(3) 3_646
C2 H2 O1 1.095(3) 2.602(5) 3.3110(3) 121.7(3) 1_655
C7A H7A O5 1.083(3) 2.500(5) 3.4160(3) 141.7(3) 3_656
####################################################################### 
# 
# 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_BOH2N_Cl_2
_database_code_depnum_ccdc_archive 'CCDC 1847375'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C5 H7 B Cl N O2'
_chemical_formula_weight         159.38
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1507 0.1611 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0014 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_space_group_IT_number           7
_symmetry_space_group_name_H-M   Pc
_space_group_name_Hall           'P -2yc'

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

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

_cell_length_a                   6.20620(5)
_cell_length_b                   5.25334(4)
_cell_length_c                   11.18373(9)
_cell_angle_alpha                90
_cell_angle_beta                 105.5034(8)
_cell_angle_gamma                90
_cell_volume                     351.359(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    25830
_cell_measurement_theta_min      3.3830
_cell_measurement_theta_max      65.0110

_exptl_crystal_description       colourless
_exptl_crystal_colour            block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_F_000             164
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.467
_shelx_estimated_absorpt_T_min   0.873
_shelx_estimated_absorpt_T_max   0.892
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.686
_exptl_absorpt_correction_T_max  0.892
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_power             50
_diffrn_source_current           24
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            31805
_diffrn_reflns_av_unetI/netI     0.0090
_diffrn_reflns_av_R_equivalents  0.0121
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.407
_diffrn_reflns_theta_max         58.524
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.736
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             7501
_reflns_number_gt                7484
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.549
_reflns_Friedel_fraction_max     0.523
_reflns_Friedel_fraction_full    0.961
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_structure_solution    Sir2014
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2637 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration ad
_refine_ls_abs_structure_Flack   0.010(6)
_refine_ls_number_reflns         7501
_refine_ls_number_parameters     119
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0136
_refine_ls_R_factor_gt           0.0135
_refine_ls_wR_factor_ref         0.0459
_refine_ls_wR_factor_gt          0.0457
_refine_ls_goodness_of_fit_ref   0.450
_refine_ls_restrained_S_all      0.450
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.04986(2) -0.32535(2) 0.30580(2) 0.01088(1) Uani 1 1 d . . . . .
O1 O 0.94859(4) 0.80629(4) 0.55399(3) 0.01488(3) Uani 1 1 d . . . . .
O2 O 0.72955(3) 0.87893(3) 0.69346(2) 0.01265(2) Uani 1 1 d . . . . .
H2O H 0.829(3) 0.999(3) 0.7256(16) 0.038(4) Uiso 1 1 d . . . . .
N1 N 0.31836(3) 0.11851(3) 0.45657(2) 0.01163(2) Uani 1 1 d . . . . .
C1 C 0.61091(3) 0.51059(4) 0.54737(2) 0.00981(2) Uani 1 1 d . . . . .
C2 C 0.43852(4) 0.44791(4) 0.60158(2) 0.01149(2) Uani 1 1 d . . . . .
C3 C 0.29335(4) 0.24978(4) 0.55497(2) 0.01225(2) Uani 1 1 d . . . . .
C4 C 0.47902(5) 0.17144(4) 0.40056(3) 0.01242(3) Uani 1 1 d . . . . .
C5 C 0.62880(4) 0.36665(5) 0.44484(2) 0.01180(2) Uani 1 1 d . . . . .
B1 B 0.77646(4) 0.73996(5) 0.60141(2) 0.01062(3) Uani 1 1 d . . . . .
H1 H 0.234(3) -0.007(3) 0.4295(15) 0.035(4) Uiso 1 1 d . . . . .
H2 H 0.425(3) 0.544(3) 0.6700(16) 0.029(3) Uiso 1 1 d . . . . .
H1O H 0.972(3) 0.734(4) 0.4815(17) 0.043(5) Uiso 1 1 d . . . . .
H3 H 0.187(3) 0.192(2) 0.5819(15) 0.019(3) Uiso 1 1 d . . . . .
H4 H 0.489(3) 0.068(3) 0.3383(15) 0.028(3) Uiso 1 1 d . . . . .
H5 H 0.743(3) 0.407(3) 0.4089(14) 0.029(3) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 B1 1.3589(3) . ?
O1 H1O 0.942(19) . ?
O2 B1 1.3557(3) . ?
O2 H2O 0.887(18) . ?
N1 C4 1.3408(4) . ?
N1 C3 1.3425(3) . ?
N1 H1 0.845(17) . ?
C1 C5 1.4025(3) . ?
C1 C2 1.4026(3) . ?
C1 B1 1.5940(3) . ?
C2 C3 1.3841(3) . ?
C2 H2 0.938(16) . ?
C3 H3 0.851(18) . ?
C4 C5 1.3838(3) . ?
C4 H4 0.899(15) . ?
C5 H5 0.926(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
B1 O1 H1O 123.6(13) . . ?
B1 O2 H2O 114.9(12) . . ?
C4 N1 C3 122.674(18) . . ?
C4 N1 H1 117.5(12) . . ?
C3 N1 H1 119.8(12) . . ?
C5 C1 C2 117.583(18) . . ?
C5 C1 B1 122.252(18) . . ?
C2 C1 B1 120.162(18) . . ?
C3 C2 C1 120.58(2) . . ?
C3 C2 H2 121.4(10) . . ?
C1 C2 H2 118.0(10) . . ?
N1 C3 C2 119.258(19) . . ?
N1 C3 H3 112.3(10) . . ?
C2 C3 H3 128.5(10) . . ?
N1 C4 C5 119.92(2) . . ?
N1 C4 H4 116.8(10) . . ?
C5 C4 H4 123.2(10) . . ?
C4 C5 C1 119.99(2) . . ?
C4 C5 H5 122.2(10) . . ?
C1 C5 H5 117.8(10) . . ?
O2 B1 O1 120.60(2) . . ?
O2 B1 C1 116.580(19) . . ?
O1 B1 C1 122.69(2) . . ?

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
C5 C1 C2 C3 0.35(4) . . . . ?
B1 C1 C2 C3 179.72(2) . . . . ?
C4 N1 C3 C2 -0.14(4) . . . . ?
C1 C2 C3 N1 -0.38(4) . . . . ?
C3 N1 C4 C5 0.68(4) . . . . ?
N1 C4 C5 C1 -0.69(4) . . . . ?
C2 C1 C5 C4 0.18(4) . . . . ?
B1 C1 C5 C4 -179.18(2) . . . . ?
C5 C1 B1 O2 174.19(2) . . . . ?
C2 C1 B1 O2 -5.15(3) . . . . ?
C5 C1 B1 O1 -1.82(4) . . . . ?
C2 C1 B1 O1 178.84(3) . . . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_14DNB_BNI_b
_database_code_depnum_ccdc_archive 'CCDC 1847376'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H4 N2 O4'
_chemical_formula_weight         168.11

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   5.66357(3)
_cell_length_b                   5.37326(3)
_cell_length_c                   10.91612(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.0201(5)
_cell_angle_gamma                90
_cell_volume                     331.991(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    53740
_cell_measurement_theta_min      3.5890
_cell_measurement_theta_max      65.1240

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_F_000             172
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.758
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      90(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_power             50
_diffrn_source_current           24
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            69397
_diffrn_reflns_av_unetI/netI     0.0056
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.735
_diffrn_reflns_theta_max         55.161
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4276
_reflns_number_gt                4093
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;


_computing_data_collection       'CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_structure_solution    Sir2014
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0634P)²+0.0129P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4276
_refine_ls_number_parameters     63
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.1041
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.68916(4) 0.10521(4) 0.14348(2) 0.01343(3) Uani 1 1 d . . . . .
O1 O 0.56543(4) 0.01495(5) 0.22216(2) 0.01978(4) Uani 1 1 d . . . . .
O2 O 0.89034(4) 0.03576(5) 0.12331(2) 0.02023(4) Uani 1 1 d . . . . .
C1 C 0.59036(3) 0.31048(4) 0.06864(2) 0.01159(3) Uani 1 1 d . . . . .
C2 C 0.37975(4) 0.41777(4) 0.10329(2) 0.01349(4) Uani 1 1 d . . . . .
C3 C 0.71297(4) 0.38720(4) -0.03290(2) 0.01341(4) Uani 1 1 d . . . . .
H2 H 0.2997(17) 0.3683(19) 0.1701(9) 0.032(2) Uiso 1 1 d . . . . .
H3 H 0.8663(15) 0.3059(19) -0.0508(9) 0.038(2) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 O2 1.2262(3) . ?
N1 O1 1.2273(3) . ?
N1 C1 1.4714(3) . ?
C1 C2 1.3893(3) . ?
C1 C3 1.3910(3) . ?
C2 C3 1.3914(3) 3_665 ?
C3 C2 1.3914(3) 3_665 ?

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
O2 N1 O1 124.23(2) . . ?
O2 N1 C1 117.77(2) . . ?
O1 N1 C1 118.00(2) . . ?
C2 C1 C3 123.469(19) . . ?
C2 C1 N1 118.246(19) . . ?
C3 C1 N1 118.285(18) . . ?
C1 C2 C3 118.234(19) . 3_665 ?
C1 C3 C2 118.296(19) . 3_665 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N1 C1 C2 -169.66(2) . . . . ?
O1 N1 C1 C2 10.17(3) . . . . ?
O2 N1 C1 C3 10.20(3) . . . . ?
O1 N1 C1 C3 -169.96(2) . . . . ?
C3 C1 C2 C3 -0.21(4) . . . 3_665 ?
N1 C1 C2 C3 179.651(19) . . . 3_665 ?
C2 C1 C3 C2 0.21(4) . . . 3_665 ?
N1 C1 C3 C2 -179.650(19) . . . 3_665 ?

_refine_diff_density_max         0.607
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.064

####################################################################### 
# 
# 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_Tart-BPNox_B
_database_code_depnum_ccdc_archive 'CCDC 1847377'
_audit_update_record             
;
2018-06-05 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N2 O8'
_chemical_formula_weight         338.27

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   4.54306(6)
_cell_length_b                   15.2647(2)
_cell_length_c                   20.3244(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1409.47(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    28381
_cell_measurement_theta_min      2.0070
_cell_measurement_theta_max      57.7740

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.133
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_exptl_special_details           
; 
 It should be noted that the esd's of the cell dimensions are probably too low;
 they should be multiplied by a factor of 2 to 10
;
_diffrn_ambient_temperature      90(2)
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Microfocus rotating anode X-ray tube'
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_power             50
_diffrn_source_current           24
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_radiation_monochromator  'Confocal Max Flux optic'
_diffrn_detector_type            'PILATUS 200K'
_diffrn_measurement_device_type  '1/4chi goniometer'
_diffrn_measurement_method       
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            89157
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.668
_diffrn_reflns_theta_max         57.347
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             18682
_reflns_number_gt                16371
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_max     0.914
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.12b (Rigaku OD, 2015)'
_computing_structure_solution    SIR2014
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0497P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 6452 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(11)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         18682
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0827
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.02022(9) 0.18277(2) 0.65465(2) 0.01278(5) Uani 1 1 d . . . . .
H1A H 0.657(3) 0.7609(9) 0.7361(7) 0.023(3) Uiso 1 1 d . . . . .
H1 H -0.146(4) 0.2277(10) 0.6601(8) 0.040(4) Uiso 1 1 d . . . . .
C1 C 0.13705(9) 0.18851(3) 0.60076(2) 0.00987(5) Uani 1 1 d . . . . .
O2 O 0.12515(9) 0.24698(2) 0.56020(2) 0.01349(5) Uani 1 1 d . . . . .
H2A H 0.329(4) 0.6415(10) 0.7481(8) 0.032(4) Uiso 1 1 d . . . . .
H2 H 0.460(3) 0.1109(8) 0.6332(6) 0.018(3) Uiso 1 1 d . . . . .
C2 C 0.34864(9) 0.11195(2) 0.59295(2) 0.00956(5) Uani 1 1 d . . . . .
O3 O 0.54082(8) 0.12641(2) 0.53970(2) 0.01249(5) Uani 1 1 d . . . . .
H3O H 0.505(3) 0.1784(8) 0.5199(7) 0.019(3) Uiso 1 1 d . . . . .
H3 H 0.050(3) 0.0147(8) 0.6215(6) 0.015(2) Uiso 1 1 d . . . . .
C3 C 0.17806(9) 0.02564(3) 0.58229(2) 0.00950(5) Uani 1 1 d . . . . .
C4 C 0.39025(9) -0.05182(2) 0.58132(2) 0.00972(5) Uani 1 1 d . . . . .
H4A H 0.425(3) 0.5997(8) 0.5459(6) 0.019(3) Uiso 1 1 d . . . . .
H4 H -0.140(4) 0.0592(8) 0.5271(7) 0.026(3) Uiso 1 1 d . . . . .
O4 O 0.02026(8) 0.02622(2) 0.52298(2) 0.01223(5) Uani 1 1 d . . . . .
O6 O 0.41442(9) -0.10205(2) 0.53546(2) 0.01322(5) Uani 1 1 d . . . . .
O5 O 0.54308(9) -0.05705(2) 0.63680(2) 0.01267(5) Uani 1 1 d . . . . .
H5A H 0.726(3) 0.7196(8) 0.5459(7) 0.022(3) Uiso 1 1 d . . . . .
H5O H 0.668(5) -0.1028(12) 0.6360(9) 0.052(5) Uiso 1 1 d . . . . .
O2A O -0.36851(9) 0.30582(2) 0.67311(2) 0.01408(5) Uani 1 1 d . . . . .
C3A C 0.33739(10) 0.60333(3) 0.64953(2) 0.01166(5) Uani 1 1 d . . . . .
C4A C 0.45487(12) 0.62976(3) 0.58904(2) 0.01355(6) Uani 1 1 d . . . . .
C5A C 0.64133(12) 0.70117(3) 0.58561(2) 0.01378(6) Uani 1 1 d . . . . .
C6A C 0.14729(10) 0.52531(3) 0.65587(2) 0.01141(5) Uani 1 1 d . . . . .
C7A C 0.11770(12) 0.48152(3) 0.71624(2) 0.01473(6) Uani 1 1 d . . . . .
C8A C -0.05992(12) 0.40838(3) 0.72140(2) 0.01458(6) Uani 1 1 d . . . . .
C9A C -0.18338(11) 0.41841(3) 0.60921(2) 0.01294(6) Uani 1 1 d . . . . .
C10A C -0.00877(11) 0.49188(3) 0.60216(2) 0.01265(6) Uani 1 1 d . . . . .
C2A C 0.41122(13) 0.65307(4) 0.70494(2) 0.01651(7) Uani 1 1 d . . . . .
N2A N -0.20531(9) 0.37804(2) 0.66796(2) 0.01150(5) Uani 1 1 d . . . . .
O1A O 0.89313(9) 0.81460(2) 0.63689(2) 0.01412(5) Uani 1 1 d . . . . .
H10A H -0.003(3) 0.5192(7) 0.5589(6) 0.014(2) Uiso 1 1 d . . . . .
H9A H -0.295(3) 0.3925(7) 0.5715(6) 0.017(3) Uiso 1 1 d . . . . .
H8A H -0.087(3) 0.3758(9) 0.7619(7) 0.023(3) Uiso 1 1 d . . . . .
H7A H 0.224(3) 0.4989(9) 0.7559(7) 0.023(3) Uiso 1 1 d . . . . .
C1A C 0.59873(13) 0.72373(4) 0.69957(2) 0.01665(7) Uani 1 1 d . . . . .
N1A N 0.71254(9) 0.74635(2) 0.64064(2) 0.01174(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.3107(5) . ?
O1 H1 0.898(17) . ?
C1 O2 1.2162(5) . ?
C1 C2 1.5214(6) . ?
C2 O3 1.4079(5) . ?
C2 C3 1.5439(6) . ?
C2 H2 0.961(13) . ?
O3 H3O 0.904(12) . ?
C3 O4 1.4024(5) . ?
C3 C4 1.5257(5) . ?
C3 H3 1.001(13) . ?
C4 O6 1.2119(5) . ?
C4 O5 1.3265(5) . ?
O4 H4 0.890(15) . ?
O5 H5O 0.90(2) . ?
O2A N2A 1.3327(5) . ?
C3A C2A 1.3990(7) . ?
C3A C4A 1.3998(6) . ?
C3A C6A 1.4767(6) . ?
C4A C5A 1.3822(7) . ?
C4A H4A 1.000(13) . ?
C5A N1A 1.3532(6) . ?
C5A H5A 0.938(14) . ?
C6A C10A 1.3980(6) . ?
C6A C7A 1.4039(6) . ?
C7A C8A 1.3816(7) . ?
C7A H7A 0.977(14) . ?
C8A N2A 1.3530(6) . ?
C8A H8A 0.969(13) . ?
C9A N2A 1.3473(6) . ?
C9A C10A 1.3812(7) . ?
C9A H9A 1.001(13) . ?
C10A H10A 0.973(11) . ?
C2A C1A 1.3788(7) . ?
C2A H2A 0.969(16) . ?
O1A N1A 1.3283(5) . ?
C1A N1A 1.3494(6) . ?
C1A H1A 0.970(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 113.4(11) . . ?
O2 C1 O1 126.24(4) . . ?
O2 C1 C2 121.41(4) . . ?
O1 C1 C2 112.35(3) . . ?
O3 C2 C1 110.58(3) . . ?
O3 C2 C3 109.70(3) . . ?
C1 C2 C3 110.67(3) . . ?
O3 C2 H2 109.2(8) . . ?
C1 C2 H2 104.9(8) . . ?
C3 C2 H2 111.7(7) . . ?
C2 O3 H3O 111.6(9) . . ?
O4 C3 C4 108.47(3) . . ?
O4 C3 C2 111.83(3) . . ?
C4 C3 C2 110.24(3) . . ?
O4 C3 H3 112.8(8) . . ?
C4 C3 H3 104.4(7) . . ?
C2 C3 H3 108.9(7) . . ?
O6 C4 O5 124.62(4) . . ?
O6 C4 C3 123.88(4) . . ?
O5 C4 C3 111.50(3) . . ?
C3 O4 H4 110.0(10) . . ?
C4 O5 H5O 111.2(12) . . ?
C2A C3A C4A 117.33(4) . . ?
C2A C3A C6A 120.51(4) . . ?
C4A C3A C6A 122.15(4) . . ?
C5A C4A C3A 120.35(4) . . ?
C5A C4A H4A 113.6(7) . . ?
C3A C4A H4A 126.0(7) . . ?
N1A C5A C4A 120.45(4) . . ?
N1A C5A H5A 117.3(8) . . ?
C4A C5A H5A 122.2(8) . . ?
C10A C6A C7A 117.39(4) . . ?
C10A C6A C3A 121.53(4) . . ?
C7A C6A C3A 121.08(4) . . ?
C8A C7A C6A 120.47(4) . . ?
C8A C7A H7A 116.5(8) . . ?
C6A C7A H7A 123.0(8) . . ?
N2A C8A C7A 120.05(4) . . ?
N2A C8A H8A 116.3(8) . . ?
C7A C8A H8A 123.6(8) . . ?
N2A C9A C10A 120.38(4) . . ?
N2A C9A H9A 117.4(7) . . ?
C10A C9A H9A 122.2(7) . . ?
C9A C10A C6A 120.45(4) . . ?
C9A C10A H10A 117.2(7) . . ?
C6A C10A H10A 122.3(7) . . ?
C1A C2A C3A 120.60(4) . . ?
C1A C2A H2A 116.9(9) . . ?
C3A C2A H2A 122.5(9) . . ?
O2A N2A C9A 119.28(4) . . ?
O2A N2A C8A 119.45(4) . . ?
C9A N2A C8A 121.25(4) . . ?
N1A C1A C2A 120.48(4) . . ?
N1A C1A H1A 115.1(8) . . ?
C2A C1A H1A 124.4(8) . . ?
O1A N1A C1A 119.23(4) . . ?
O1A N1A C5A 119.99(4) . . ?
C1A N1A C5A 120.77(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C1 C2 O3 7.76(6) . . . . ?
O1 C1 C2 O3 -171.91(4) . . . . ?
O2 C1 C2 C3 -114.01(4) . . . . ?
O1 C1 C2 C3 66.32(4) . . . . ?
O3 C2 C3 O4 -57.46(4) . . . . ?
C1 C2 C3 O4 64.82(4) . . . . ?
O3 C2 C3 C4 63.30(4) . . . . ?
C1 C2 C3 C4 -174.41(3) . . . . ?
O4 C3 C4 O6 1.04(6) . . . . ?
C2 C3 C4 O6 -121.72(4) . . . . ?
O4 C3 C4 O5 -178.85(4) . . . . ?
C2 C3 C4 O5 58.39(4) . . . . ?
C2A C3A C4A C5A 1.44(7) . . . . ?
C6A C3A C4A C5A -177.43(5) . . . . ?
C3A C4A C5A N1A 0.01(8) . . . . ?
C2A C3A C6A C10A 158.38(5) . . . . ?
C4A C3A C6A C10A -22.79(7) . . . . ?
C2A C3A C6A C7A -21.96(7) . . . . ?
C4A C3A C6A C7A 156.88(5) . . . . ?
C10A C6A C7A C8A -0.04(7) . . . . ?
C3A C6A C7A C8A -179.72(5) . . . . ?
C6A C7A C8A N2A 0.48(8) . . . . ?
N2A C9A C10A C6A -0.03(7) . . . . ?
C7A C6A C10A C9A -0.18(7) . . . . ?
C3A C6A C10A C9A 179.49(4) . . . . ?
C4A C3A C2A C1A -1.66(8) . . . . ?
C6A C3A C2A C1A 177.23(5) . . . . ?
C10A C9A N2A O2A -178.11(4) . . . . ?
C10A C9A N2A C8A 0.48(7) . . . . ?
C7A C8A N2A O2A 177.88(4) . . . . ?
C7A C8A N2A C9A -0.70(7) . . . . ?
C3A C2A C1A N1A 0.42(9) . . . . ?
C2A C1A N1A O1A -179.86(5) . . . . ?
C2A C1A N1A C5A 1.10(8) . . . . ?
C4A C5A N1A O1A 179.65(4) . . . . ?
C4A C5A N1A C1A -1.32(8) . . . . ?

_refine_diff_density_max         0.565
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.062

