# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_dm16916
_database_code_depnum_ccdc_archive 'CCDC 1535226'
_audit_update_record             
;
2017-02-28 deposited with the CCDC.
2017-08-09 downloaded from the CCDC.
;
_audit_creation_date             2016-12-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H4 F2 N8 O11'
_chemical_formula_sum            'C8 H4 F2 N8 O11'
_chemical_formula_weight         426.19
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   10.833(2)
_cell_length_b                   14.932(2)
_cell_length_c                   18.906(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3058.2(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1239
_cell_measurement_temperature    130
_cell_measurement_theta_max      22.78
_cell_measurement_theta_min      2.56
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0484 before and 0.0358 after correction.
The Ratio of minimum to maximum transmission is 0.8906.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            7542
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.188
_diffrn_reflns_theta_min         2.561
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.896
_reflns_number_gt                1503
_reflns_number_total             2354
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.303
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 539 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2354
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      0.955
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0373P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0860
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.33942(16) 0.34649(13) 0.33758(11) 0.0369(5) Uani 1 1 d . . . . .
O1 O 0.0489(2) 0.38187(19) 0.38437(15) 0.0486(7) Uani 1 1 d . . . . .
O2 O 0.1213(3) 0.33974(17) 0.28181(15) 0.0476(7) Uani 1 1 d . . . . .
O3 O 0.20571(19) 0.55304(15) 0.33312(13) 0.0308(5) Uani 1 1 d . . . . .
O4 O 0.3558(2) 0.49289(17) 0.27154(13) 0.0366(6) Uani 1 1 d . . . . .
O5 O 0.39218(19) 0.46634(14) 0.44179(11) 0.0275(5) Uani 1 1 d . . . . .
O6 O 0.500000 0.500000 0.72896(18) 0.0446(9) Uani 1 2 d S T P . .
N1 N 0.1299(2) 0.37260(17) 0.34056(17) 0.0326(6) Uani 1 1 d . . . . .
N2 N 0.2761(2) 0.49235(18) 0.31662(13) 0.0255(5) Uani 1 1 d . . . . .
N3 N 0.3736(2) 0.46416(18) 0.56251(15) 0.0257(5) Uani 1 1 d . . . . .
N4 N 0.4002(3) 0.4712(2) 0.68803(15) 0.0381(7) Uani 1 1 d . . . . .
C1 C 0.2586(3) 0.40676(19) 0.36053(17) 0.0247(6) Uani 1 1 d . . . . .
C2 C 0.2706(3) 0.4268(2) 0.43813(17) 0.0267(7) Uani 1 1 d . . . . .
H2A H 0.206326 0.469355 0.454094 0.032 Uiso 1 1 calc R . . . .
H2B H 0.265631 0.371492 0.466852 0.032 Uiso 1 1 calc R . . . .
C3 C 0.4368(3) 0.4814(2) 0.50676(15) 0.0232(6) Uani 1 1 d . . . . .
C4 C 0.4390(3) 0.4829(2) 0.62319(17) 0.0270(7) 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
F1 C1 1.328(3) . ?
O1 N1 1.214(4) . ?
O2 N1 1.218(4) . ?
O3 N2 1.225(3) . ?
O4 N2 1.214(3) . ?
O5 C2 1.445(3) . ?
O5 C3 1.339(4) . ?
O6 N4 1.397(3) . ?
O6 N4 1.397(3) 2_665 ?
N1 C1 1.532(4) . ?
N2 C1 1.536(4) . ?
N3 C3 1.283(4) . ?
N3 C4 1.377(4) . ?
N4 C4 1.308(4) . ?
C1 C2 1.503(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C3 1.478(6) 2_665 ?
C4 C4 1.417(6) 2_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
C3 O5 C2 116.2(2) . . ?
N4 O6 N4 112.7(3) 2_665 . ?
O1 N1 O2 127.8(3) . . ?
O1 N1 C1 116.8(3) . . ?
O2 N1 C1 115.3(3) . . ?
O3 N2 C1 113.7(2) . . ?
O4 N2 O3 128.1(3) . . ?
O4 N2 C1 118.2(2) . . ?
C3 N3 C4 111.7(2) . . ?
C4 N4 O6 103.3(3) . . ?
F1 C1 N1 107.1(2) . . ?
F1 C1 N2 107.8(2) . . ?
F1 C1 C2 113.4(3) . . ?
N1 C1 N2 104.8(2) . . ?
C2 C1 N1 112.7(2) . . ?
C2 C1 N2 110.6(2) . . ?
O5 C2 C1 102.0(2) . . ?
O5 C2 H2A 111.4 . . ?
O5 C2 H2B 111.4 . . ?
C1 C2 H2A 111.4 . . ?
C1 C2 H2B 111.4 . . ?
H2A C2 H2B 109.2 . . ?
O5 C3 C3 113.42(16) . 2_665 ?
N3 C3 O5 121.8(3) . . ?
N3 C3 C3 124.75(18) . 2_665 ?
N3 C4 C4 123.59(16) . 2_665 ?
N4 C4 N3 126.1(3) . . ?
N4 C4 C4 110.35(19) . 2_665 ?

_shelx_SHELXL_version_number     2016/6
_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_cd17027
_database_code_depnum_ccdc_archive 'CCDC 1535227'
_audit_update_record             
;
2017-02-28 deposited with the CCDC.
2017-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H4 F2 N8 O11'
_chemical_formula_weight         426.19

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   11.0371(13)
_cell_length_b                   13.1237(16)
_cell_length_c                   10.6684(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1545.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1837
_cell_measurement_theta_min      4.822
_cell_measurement_theta_max      41.697

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.832
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.184
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6542
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7951
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.552
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_point_group_measured_fraction_full 0.846
_reflns_number_total             2370
_reflns_number_gt                2118
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.640
_reflns_Friedel_fraction_max     0.725
_reflns_Friedel_fraction_full    0.704

_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0841P)²+1.1807P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 703 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.1(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2370
_refine_ls_number_parameters     262
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1593
_refine_ls_wR_factor_gt          0.1542
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.000
_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
F1 F 0.8068(4) 0.0491(3) -0.0987(6) 0.0746(15) Uani 1 1 d . . . . .
F2 F 0.7305(5) 0.4111(4) 0.1539(5) 0.0783(15) Uani 1 1 d . . . . .
N1 N 1.3966(5) 0.2690(5) -0.0155(7) 0.0549(17) Uani 1 1 d . . . . .
N2 N 1.3667(5) 0.3737(5) 0.1529(7) 0.0585(17) Uani 1 1 d . . . . .
N3 N 1.1909(5) 0.2163(4) -0.0412(5) 0.0393(12) Uani 1 1 d . . . . .
N4 N 1.1520(5) 0.3521(4) 0.1694(5) 0.0395(12) Uani 1 1 d . . . . .
N5 N 0.9366(6) -0.0678(4) -0.1865(5) 0.0447(14) Uani 1 1 d . . . . .
N6 N 0.9405(8) -0.0265(5) 0.0355(6) 0.0618(19) Uani 1 1 d . . . . .
N7 N 0.7543(10) 0.2864(7) 0.3077(12) 0.095(3) Uani 1 1 d . . . . .
N8 N 0.7576(8) 0.4590(6) 0.3676(6) 0.0624(18) Uani 1 1 d . . . . .
O1 O 1.4491(5) 0.3326(4) 0.0688(6) 0.0648(16) Uani 1 1 d . . . . .
O2 O 0.9895(4) 0.1788(3) -0.0244(4) 0.0410(11) Uani 1 1 d . . . . .
O3 O 0.9535(4) 0.3120(3) 0.1512(4) 0.0392(10) Uani 1 1 d . . . . .
O4 O 1.0398(6) -0.0949(4) -0.2036(6) 0.0679(16) Uani 1 1 d . . . . .
O5 O 0.8465(6) -0.1007(4) -0.2346(6) 0.0709(17) Uani 1 1 d . . . . .
O6 O 1.0443(8) -0.0391(6) 0.0642(6) 0.092(2) Uani 1 1 d . . . . .
O7 O 0.8543(8) -0.0485(6) 0.0949(7) 0.102(3) Uani 1 1 d . . . . .
O8 O 0.6854(7) 0.2408(6) 0.2240(11) 0.113(3) Uani 1 1 d . . . . .
O9 O 0.7964(7) 0.2646(5) 0.4015(8) 0.0788(19) Uani 1 1 d . . . . .
O10 O 0.6519(6) 0.4600(7) 0.3885(7) 0.101(3) Uani 1 1 d . . . . .
O11 O 0.8342(7) 0.5107(5) 0.4121(6) 0.0818(19) Uani 1 1 d . . . . .
C1 C 1.2814(5) 0.2712(5) 0.0159(7) 0.0417(15) Uani 1 1 d . . . . .
C2 C 1.2634(6) 0.3345(4) 0.1166(7) 0.0412(15) Uani 1 1 d . . . . .
C3 C 1.0671(5) 0.3021(4) 0.1172(6) 0.0315(13) Uani 1 1 d . . . . .
C4 C 1.0884(5) 0.2299(4) 0.0119(6) 0.0319(12) Uani 1 1 d . . . . .
C5 C 1.0086(6) 0.1042(5) -0.1203(7) 0.0427(15) Uani 1 1 d . . . . .
H5A H 1.0909 0.0784 -0.1171 0.051 Uiso 1 1 calc R U . . .
H5B H 0.9944 0.1335 -0.2025 0.051 Uiso 1 1 calc R U . . .
C6 C 0.9194(6) 0.0205(4) -0.0943(6) 0.0392(14) Uani 1 1 d . . . . .
C7 C 0.9310(6) 0.3853(5) 0.2464(6) 0.0391(15) Uani 1 1 d . . . . .
H7A H 0.9552 0.4527 0.2186 0.047 Uiso 1 1 calc R U . . .
H7B H 0.9757 0.3685 0.3219 0.047 Uiso 1 1 calc R U . . .
C8 C 0.7993(8) 0.3819(7) 0.2701(10) 0.073(3) 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
F1 C6 1.299(8) . ?
F2 C8 1.503(12) . ?
N1 C1 1.316(9) . ?
N1 O1 1.358(8) . ?
N2 C2 1.310(8) . ?
N2 O1 1.387(8) . ?
N3 C4 1.277(8) . ?
N3 C1 1.374(8) . ?
N4 C3 1.273(8) . ?
N4 C2 1.372(8) . ?
N5 O5 1.199(8) . ?
N5 O4 1.207(8) . ?
N5 C6 1.532(8) . ?
N6 O7 1.178(9) . ?
N6 O6 1.198(9) . ?
N6 C6 1.533(10) . ?
N7 O9 1.140(13) . ?
N7 O8 1.316(15) . ?
N7 C8 1.407(14) . ?
N8 O11 1.183(10) . ?
N8 O10 1.188(10) . ?
N8 C8 1.522(10) . ?
O2 C4 1.339(7) . ?
O2 C5 1.431(7) . ?
O3 C3 1.311(7) . ?
O3 C7 1.421(7) . ?
C1 C2 1.372(10) . ?
C3 C4 1.488(8) . ?
C5 C6 1.501(9) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 C8 1.477(10) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

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 O1 103.3(6) . . ?
C2 N2 O1 103.1(6) . . ?
C4 N3 C1 112.0(5) . . ?
C3 N4 C2 113.1(5) . . ?
O5 N5 O4 127.8(6) . . ?
O5 N5 C6 116.4(6) . . ?
O4 N5 C6 115.9(5) . . ?
O7 N6 O6 126.9(9) . . ?
O7 N6 C6 117.5(8) . . ?
O6 N6 C6 115.6(7) . . ?
O9 N7 O8 135.8(11) . . ?
O9 N7 C8 109.2(11) . . ?
O8 N7 C8 114.6(12) . . ?
O11 N8 O10 128.3(7) . . ?
O11 N8 C8 116.0(7) . . ?
O10 N8 C8 115.6(8) . . ?
N1 O1 N2 112.8(5) . . ?
C4 O2 C5 115.4(4) . . ?
C3 O3 C7 115.6(5) . . ?
N1 C1 C2 110.7(6) . . ?
N1 C1 N3 125.3(6) . . ?
C2 C1 N3 123.9(6) . . ?
N2 C2 N4 126.3(6) . . ?
N2 C2 C1 110.1(6) . . ?
N4 C2 C1 123.6(6) . . ?
N4 C3 O3 122.1(5) . . ?
N4 C3 C4 122.8(5) . . ?
O3 C3 C4 115.0(5) . . ?
N3 C4 O2 121.6(5) . . ?
N3 C4 C3 124.3(5) . . ?
O2 C4 C3 114.1(5) . . ?
O2 C5 C6 105.8(5) . . ?
O2 C5 H5A 110.6 . . ?
C6 C5 H5A 110.6 . . ?
O2 C5 H5B 110.6 . . ?
C6 C5 H5B 110.6 . . ?
H5A C5 H5B 108.7 . . ?
F1 C6 C5 114.1(6) . . ?
F1 C6 N5 108.3(6) . . ?
C5 C6 N5 110.7(5) . . ?
F1 C6 N6 107.1(6) . . ?
C5 C6 N6 111.2(6) . . ?
N5 C6 N6 104.9(5) . . ?
O3 C7 C8 105.9(5) . . ?
O3 C7 H7A 110.6 . . ?
C8 C7 H7A 110.6 . . ?
O3 C7 H7B 110.6 . . ?
C8 C7 H7B 110.6 . . ?
H7A C7 H7B 108.7 . . ?
N7 C8 C7 115.0(8) . . ?
N7 C8 F2 106.5(8) . . ?
C7 C8 F2 110.4(8) . . ?
N7 C8 N8 107.0(8) . . ?
C7 C8 N8 113.3(7) . . ?
F2 C8 N8 104.0(6) . . ?

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
C1 N1 O1 N2 0.4(8) . . . . ?
C2 N2 O1 N1 -0.7(8) . . . . ?
O1 N1 C1 C2 0.1(8) . . . . ?
O1 N1 C1 N3 -178.4(6) . . . . ?
C4 N3 C1 N1 177.2(7) . . . . ?
C4 N3 C1 C2 -1.1(9) . . . . ?
O1 N2 C2 N4 -179.5(6) . . . . ?
O1 N2 C2 C1 0.8(8) . . . . ?
C3 N4 C2 N2 -178.4(7) . . . . ?
C3 N4 C2 C1 1.4(9) . . . . ?
N1 C1 C2 N2 -0.6(8) . . . . ?
N3 C1 C2 N2 178.0(6) . . . . ?
N1 C1 C2 N4 179.7(6) . . . . ?
N3 C1 C2 N4 -1.8(10) . . . . ?
C2 N4 C3 O3 -177.2(5) . . . . ?
C2 N4 C3 C4 1.6(8) . . . . ?
C7 O3 C3 N4 2.6(8) . . . . ?
C7 O3 C3 C4 -176.3(5) . . . . ?
C1 N3 C4 O2 -176.0(5) . . . . ?
C1 N3 C4 C3 4.2(9) . . . . ?
C5 O2 C4 N3 3.9(8) . . . . ?
C5 O2 C4 C3 -176.3(5) . . . . ?
N4 C3 C4 N3 -4.9(9) . . . . ?
O3 C3 C4 N3 174.0(6) . . . . ?
N4 C3 C4 O2 175.3(6) . . . . ?
O3 C3 C4 O2 -5.8(7) . . . . ?
C4 O2 C5 C6 147.3(5) . . . . ?
O2 C5 C6 F1 61.1(8) . . . . ?
O2 C5 C6 N5 -176.4(5) . . . . ?
O2 C5 C6 N6 -60.2(7) . . . . ?
O5 N5 C6 F1 -7.1(8) . . . . ?
O4 N5 C6 F1 171.7(6) . . . . ?
O5 N5 C6 C5 -133.0(6) . . . . ?
O4 N5 C6 C5 45.9(8) . . . . ?
O5 N5 C6 N6 107.0(7) . . . . ?
O4 N5 C6 N6 -74.2(7) . . . . ?
O7 N6 C6 F1 15.4(8) . . . . ?
O6 N6 C6 F1 -166.2(7) . . . . ?
O7 N6 C6 C5 140.8(7) . . . . ?
O6 N6 C6 C5 -40.9(8) . . . . ?
O7 N6 C6 N5 -99.5(7) . . . . ?
O6 N6 C6 N5 78.8(8) . . . . ?
C3 O3 C7 C8 -179.2(6) . . . . ?
O9 N7 C8 C7 63.4(11) . . . . ?
O8 N7 C8 C7 -110.6(10) . . . . ?
O9 N7 C8 F2 -174.0(7) . . . . ?
O8 N7 C8 F2 12.0(10) . . . . ?
O9 N7 C8 N8 -63.3(10) . . . . ?
O8 N7 C8 N8 122.6(9) . . . . ?
O3 C7 C8 N7 58.5(11) . . . . ?
O3 C7 C8 F2 -61.9(7) . . . . ?
O3 C7 C8 N8 -178.0(7) . . . . ?
O11 N8 C8 N7 127.3(9) . . . . ?
O10 N8 C8 N7 -53.2(11) . . . . ?
O11 N8 C8 C7 -0.5(12) . . . . ?
O10 N8 C8 C7 179.0(8) . . . . ?
O11 N8 C8 F2 -120.3(7) . . . . ?
O10 N8 C8 F2 59.2(10) . . . . ?

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
C5 H5B O8 0.97 2.56 3.249(11) 128.3 4_654
C7 H7A N2 0.97 2.58 3.391(9) 141.7 3_465
C7 H7B N1 0.97 2.59 3.521(10) 161.4 4_755
C5 H5B O8 0.97 2.56 3.249(11) 128.3 4_654
C7 H7A N2 0.97 2.58 3.391(9) 141.7 3_465
C7 H7B N1 0.97 2.59 3.521(10) 161.4 4_755

_refine_diff_density_max         0.916
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.062

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_cd17106
_database_code_depnum_ccdc_archive 'CCDC 1535921'
_audit_update_record             
;
2017-03-03 deposited with the CCDC.
2017-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 Cl2 N4 O'
_chemical_formula_weight         190.98

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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'
'-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                   10.8387(17)
_cell_length_b                   7.0582(11)
_cell_length_c                   16.911(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1293.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2410
_cell_measurement_theta_min      6.111
_cell_measurement_theta_max      55.690

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.961
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.936
_shelx_estimated_absorpt_T_min   0.835
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6198
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7025
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.409
_diffrn_reflns_theta_max         25.995
_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             1267
_reflns_number_gt                1115
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0454P)²+0.2872P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   .
_refine_ls_hydrogen_treatment    undef
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0074(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1267
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0836
_refine_ls_wR_factor_gt          0.0783
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_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 -0.01618(5) 0.26288(8) 0.43872(3) 0.0580(2) Uani 1 1 d . . . . .
Cl2 Cl 0.22204(5) 0.02481(7) 0.44416(3) 0.0562(2) Uani 1 1 d . . . . .
N1 N 0.04680(18) 0.2716(3) 0.14897(11) 0.0555(4) Uani 1 1 d . . . . .
N2 N 0.22580(17) 0.0979(3) 0.15336(10) 0.0558(5) Uani 1 1 d . . . . .
N3 N 0.00756(14) 0.2751(2) 0.28770(10) 0.0419(4) Uani 1 1 d . . . . .
N4 N 0.23254(14) 0.0544(2) 0.29321(9) 0.0423(4) Uani 1 1 d . . . . .
O1 O 0.14194(15) 0.1916(2) 0.10677(8) 0.0622(4) Uani 1 1 d . . . . .
C1 C 0.07335(17) 0.2275(2) 0.22226(11) 0.0403(4) Uani 1 1 d . . . . .
C2 C 0.18251(16) 0.1221(2) 0.22459(10) 0.0393(4) Uani 1 1 d . . . . .
C3 C 0.05533(16) 0.2126(2) 0.35187(10) 0.0374(4) Uani 1 1 d . . . . .
C4 C 0.16967(16) 0.0999(2) 0.35443(10) 0.0374(4) 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
Cl1 C3 1.6984(18) . ?
Cl2 C4 1.7046(17) . ?
N1 C1 1.310(3) . ?
N1 O1 1.375(2) . ?
N2 C2 1.304(2) . ?
N2 O1 1.373(2) . ?
N3 C3 1.281(2) . ?
N3 C1 1.359(2) . ?
N4 C4 1.280(2) . ?
N4 C2 1.367(2) . ?
C1 C2 1.398(3) . ?
C3 C4 1.473(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
C1 N1 O1 103.23(16) . . ?
C2 N2 O1 103.22(15) . . ?
C3 N3 C1 113.11(15) . . ?
C4 N4 C2 112.81(15) . . ?
N2 O1 N1 113.36(14) . . ?
N1 C1 N3 126.64(18) . . ?
N1 C1 C2 109.80(17) . . ?
N3 C1 C2 123.56(16) . . ?
N2 C2 N4 126.55(17) . . ?
N2 C2 C1 110.38(16) . . ?
N4 C2 C1 123.06(15) . . ?
N3 C3 C4 123.45(15) . . ?
N3 C3 Cl1 118.43(13) . . ?
C4 C3 Cl1 118.13(13) . . ?
N4 C4 C3 124.01(15) . . ?
N4 C4 Cl2 117.69(13) . . ?
C3 C4 Cl2 118.31(13) . . ?

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
C2 N2 O1 N1 -0.6(2) . . . . ?
C1 N1 O1 N2 0.5(2) . . . . ?
O1 N1 C1 N3 179.50(16) . . . . ?
O1 N1 C1 C2 -0.2(2) . . . . ?
C3 N3 C1 N1 179.95(18) . . . . ?
C3 N3 C1 C2 -0.4(2) . . . . ?
O1 N2 C2 N4 179.58(16) . . . . ?
O1 N2 C2 C1 0.5(2) . . . . ?
C4 N4 C2 N2 -179.78(17) . . . . ?
C4 N4 C2 C1 -0.8(2) . . . . ?
N1 C1 C2 N2 -0.2(2) . . . . ?
N3 C1 C2 N2 -179.89(17) . . . . ?
N1 C1 C2 N4 -179.33(17) . . . . ?
N3 C1 C2 N4 1.0(3) . . . . ?
C1 N3 C3 C4 -0.2(2) . . . . ?
C1 N3 C3 Cl1 179.42(12) . . . . ?
C2 N4 C4 C3 0.2(2) . . . . ?
C2 N4 C4 Cl2 -179.89(12) . . . . ?
N3 C3 C4 N4 0.3(3) . . . . ?
Cl1 C3 C4 N4 -179.30(14) . . . . ?
N3 C3 C4 Cl2 -179.60(14) . . . . ?
Cl1 C3 C4 Cl2 0.77(19) . . . . ?

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.094

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_dm17022
_database_code_depnum_ccdc_archive 'CCDC 1535228'
_audit_update_record             
;
2017-02-28 deposited with the CCDC.
2017-08-09 downloaded from the CCDC.
;
_audit_creation_date             2017-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H4 F2 N8 O11'
_chemical_formula_sum            'C8 H4 F2 N8 O11'
_chemical_formula_weight         426.19
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   10.9222(18)
_cell_length_b                   13.057(2)
_cell_length_c                   10.5202(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1500.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6238
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.190
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0790 before and 0.0431 after correction.
The Ratio of minimum to maximum transmission is 0.7299.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14547
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.584
_diffrn_reflns_theta_min         1.560
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.869
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.962
_reflns_number_gt                4081
_reflns_number_total             4524
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1702 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.3(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4524
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0454P)²+0.1276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0828
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.69522(11) 0.54790(10) 0.30132(15) 0.0274(3) Uani 1 1 d . . . . .
F2 F 0.76537(13) 0.91641(10) 0.57120(13) 0.0256(3) Uani 1 1 d . . . . .
O1 O 0.03822(15) 0.82536(13) 0.48704(18) 0.0268(3) Uani 1 1 d . . . . .
O2 O 0.50864(13) 0.68094(11) 0.37944(14) 0.0178(3) Uani 1 1 d . . . . .
O3 O 0.54569(13) 0.81627(10) 0.55714(13) 0.0172(3) Uani 1 1 d . . . . .
O4 O 0.45328(16) 0.40331(12) 0.20204(16) 0.0271(3) Uani 1 1 d . . . . .
O5 O 0.65012(17) 0.39397(13) 0.16758(15) 0.0281(4) Uani 1 1 d . . . . .
O6 O 0.45377(18) 0.46249(14) 0.47438(17) 0.0332(4) Uani 1 1 d . . . . .
O7 O 0.65052(19) 0.45414(15) 0.50341(17) 0.0379(5) Uani 1 1 d . . . . .
O8 O 0.81111(19) 0.73820(15) 0.6460(2) 0.0399(5) Uani 1 1 d . . . . .
O9 O 0.71067(17) 0.76266(13) 0.82484(18) 0.0307(4) Uani 1 1 d . . . . .
O10 O 0.65929(19) 1.01478(13) 0.83056(16) 0.0309(4) Uani 1 1 d . . . . .
O11 O 0.84945(16) 0.96835(15) 0.80352(18) 0.0339(4) Uani 1 1 d . . . . .
N1 N 0.09330(18) 0.76395(14) 0.39573(19) 0.0242(4) Uani 1 1 d . . . . .
N2 N 0.12269(18) 0.86684(14) 0.57190(19) 0.0247(4) Uani 1 1 d . . . . .
N3 N 0.30340(16) 0.71608(13) 0.36515(17) 0.0181(3) Uani 1 1 d . . . . .
N4 N 0.34171(16) 0.85124(12) 0.58323(16) 0.0174(3) Uani 1 1 d . . . . .
N5 N 0.55904(18) 0.43004(13) 0.21666(16) 0.0195(3) Uani 1 1 d . . . . .
N6 N 0.55919(19) 0.47462(14) 0.44221(17) 0.0230(4) Uani 1 1 d . . . . .
N7 N 0.74706(19) 0.78640(14) 0.71993(18) 0.0242(4) Uani 1 1 d . . . . .
N8 N 0.74027(19) 0.96503(14) 0.78098(17) 0.0235(4) Uani 1 1 d . . . . .
C1 C 0.21016(19) 0.76779(15) 0.42478(19) 0.0181(4) Uani 1 1 d . . . . .
C2 C 0.22786(19) 0.83111(14) 0.53249(19) 0.0179(4) Uani 1 1 d . . . . .
C3 C 0.40785(18) 0.73107(14) 0.41802(18) 0.0148(3) Uani 1 1 d . . . . .
C4 C 0.42843(18) 0.80324(13) 0.52573(18) 0.0151(3) Uani 1 1 d . . . . .
C5 C 0.48838(19) 0.60488(15) 0.28189(19) 0.0185(4) Uani 1 1 d . . . . .
H5A H 0.502465 0.634433 0.196476 0.022 Uiso 1 1 calc R . . . .
H5B H 0.403580 0.578306 0.286033 0.022 Uiso 1 1 calc R . . . .
C6 C 0.57961(18) 0.52054(14) 0.30906(19) 0.0169(3) Uani 1 1 d . . . . .
C7 C 0.56509(18) 0.89044(15) 0.65721(19) 0.0176(4) Uani 1 1 d . . . . .
H7A H 0.523121 0.869326 0.736393 0.021 Uiso 1 1 calc R . . . .
H7B H 0.534849 0.958896 0.631669 0.021 Uiso 1 1 calc R . . . .
C8 C 0.7020(2) 0.89123(16) 0.6748(2) 0.0199(4) 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
F1 C6 1.315(2) . ?
F2 C8 1.332(3) . ?
O1 N1 1.388(2) . ?
O1 N2 1.393(2) . ?
O2 C3 1.344(2) . ?
O2 C5 1.445(2) . ?
O3 C4 1.334(2) . ?
O3 C7 1.446(2) . ?
O4 N5 1.217(2) . ?
O5 N5 1.216(2) . ?
O6 N6 1.211(3) . ?
O7 N6 1.217(3) . ?
O8 N7 1.221(3) . ?
O9 N7 1.213(3) . ?
O10 N8 1.215(3) . ?
O11 N8 1.217(3) . ?
N1 C1 1.313(3) . ?
N2 C2 1.307(3) . ?
N3 C1 1.373(3) . ?
N3 C3 1.284(3) . ?
N4 C2 1.379(3) . ?
N4 C4 1.287(3) . ?
N5 C6 1.547(3) . ?
N6 C6 1.540(3) . ?
N7 C8 1.530(3) . ?
N8 C8 1.533(3) . ?
C1 C2 1.416(3) . ?
C3 C4 1.491(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.512(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.507(3) . ?

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
N1 O1 N2 112.39(16) . . ?
C3 O2 C5 115.08(15) . . ?
C4 O3 C7 113.99(15) . . ?
C1 N1 O1 103.77(17) . . ?
C2 N2 O1 103.88(17) . . ?
C3 N3 C1 112.70(17) . . ?
C4 N4 C2 112.89(16) . . ?
O4 N5 C6 115.89(16) . . ?
O5 N5 O4 127.74(19) . . ?
O5 N5 C6 116.37(18) . . ?
O6 N6 O7 127.1(2) . . ?
O6 N6 C6 116.29(18) . . ?
O7 N6 C6 116.62(19) . . ?
O8 N7 C8 116.58(19) . . ?
O9 N7 O8 129.5(2) . . ?
O9 N7 C8 113.94(19) . . ?
O10 N8 O11 127.7(2) . . ?
O10 N8 C8 116.77(19) . . ?
O11 N8 C8 115.56(19) . . ?
N1 C1 N3 126.55(18) . . ?
N1 C1 C2 109.95(18) . . ?
N3 C1 C2 123.46(18) . . ?
N2 C2 N4 126.99(18) . . ?
N2 C2 C1 110.01(18) . . ?
N4 C2 C1 122.98(18) . . ?
O2 C3 C4 114.46(17) . . ?
N3 C3 O2 121.52(17) . . ?
N3 C3 C4 124.02(18) . . ?
O3 C4 C3 114.44(17) . . ?
N4 C4 O3 121.89(17) . . ?
N4 C4 C3 123.66(17) . . ?
O2 C5 H5A 110.7 . . ?
O2 C5 H5B 110.7 . . ?
O2 C5 C6 105.38(15) . . ?
H5A C5 H5B 108.8 . . ?
C6 C5 H5A 110.7 . . ?
C6 C5 H5B 110.7 . . ?
F1 C6 N5 107.95(16) . . ?
F1 C6 N6 107.53(17) . . ?
F1 C6 C5 115.04(16) . . ?
N6 C6 N5 104.66(14) . . ?
C5 C6 N5 110.00(16) . . ?
C5 C6 N6 111.10(16) . . ?
O3 C7 H7A 111.0 . . ?
O3 C7 H7B 111.0 . . ?
O3 C7 C8 103.84(16) . . ?
H7A C7 H7B 109.0 . . ?
C8 C7 H7A 111.0 . . ?
C8 C7 H7B 111.0 . . ?
F2 C8 N7 107.93(18) . . ?
F2 C8 N8 107.42(16) . . ?
F2 C8 C7 114.64(17) . . ?
N7 C8 N8 104.38(16) . . ?
C7 C8 N7 110.55(17) . . ?
C7 C8 N8 111.35(17) . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
