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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_iir-288-1
_database_code_depnum_ccdc_archive 'CCDC 1905323'
loop_
_audit_author_name
_audit_author_address
'Ekaterina Mescheryakova'
;Institute of Petrochemistry and Catalysis
Russia
;
_audit_update_record             
;
2019-03-25 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;
_audit_creation_date             2018-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelxl_version_number           2013-4
_chemical_name_systematic        
9-N,10-N-bis(2-fluorophenyl)-7,8,11,12-tetraoxaspiro[5.6]dodecane-9,10-diamine
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H22 F2 N2 O4'
_chemical_formula_sum            'C20 H22 F2 N2 O4'
_chemical_formula_weight         392.40
_exptl_crystal_recrystallization_method hexane/Et2O
_chemical_melting_point          ?
_exptl_crystal_description       prizm
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293(2)
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.9061(6)
_cell_length_b                   11.4711(4)
_cell_length_c                   8.7831(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.134(3)
_cell_angle_gamma                90
_cell_volume                     1880.66(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2196
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2200
_cell_measurement_theta_min      2.1230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             824.0
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0159
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9078
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.151
_diffrn_reflns_theta_min         2.084
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1709
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   86.00   1.0000    9.0250
omega____ theta____ kappa____ phi______ frames
    -       17.1042   38.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
  2 omega   45.00   82.00   1.0000    9.0250
omega____ theta____ kappa____ phi______ frames
    -       17.1042   19.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
  3 omega  -16.00   16.00   1.0000    9.0250
omega____ theta____ kappa____ phi______ frames
    -       17.1042   92.0000   53.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -21.00   54.00   1.0000    9.0250
omega____ theta____ kappa____ phi______ frames
    -       17.1042  -99.0000 -180.0000 75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0348733000
_diffrn_orient_matrix_UB_12      0.0042847000
_diffrn_orient_matrix_UB_13      0.0436012000
_diffrn_orient_matrix_UB_21      -0.0021914000
_diffrn_orient_matrix_UB_22      0.0616315000
_diffrn_orient_matrix_UB_23      -0.0042018000
_diffrn_orient_matrix_UB_31      -0.0149653000
_diffrn_orient_matrix_UB_32      0.0010212000
_diffrn_orient_matrix_UB_33      0.0691219000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'XCalibur E'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2719
_reflns_number_total             4395
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         4395
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0544
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0672P)²+0.4802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1617
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B), C5(H5A,H5B), C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C26(H26), C19(H19), C16(H16), C17(H17), C25(H25), C18(H18), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O12 O 0.30160(7) 0.60592(12) 0.13077(14) 0.0440(4) Uani 1 1 d . . . . .
O7 O 0.21925(7) 0.59431(11) -0.09484(14) 0.0412(3) Uani 1 1 d . . . . .
O11 O 0.33354(7) 0.69510(11) 0.04342(15) 0.0433(4) Uani 1 1 d . . . . .
O8 O 0.18094(7) 0.68243(11) -0.01813(15) 0.0427(4) Uani 1 1 d . . . . .
C1 C 0.26223(10) 0.52798(17) 0.0225(2) 0.0369(4) Uani 1 1 d . . . . .
N20 N 0.32905(9) 0.89167(16) -0.0026(2) 0.0455(4) Uani 1 1 d . . . . .
F1 F 0.12300(8) 1.08683(12) 0.09048(16) 0.0698(4) Uani 1 1 d . . . . .
C6 C 0.31080(11) 0.45363(19) -0.0589(2) 0.0486(5) Uani 1 1 d . . . . .
H6A H 0.3476 0.4191 0.0173 0.058 Uiso 1 1 calc R . . . .
H6B H 0.3343 0.5030 -0.1253 0.058 Uiso 1 1 calc R . . . .
C26 C 0.42837(11) 0.8989(2) 0.2146(2) 0.0478(5) Uani 1 1 d . . . . .
H26 H 0.4169 0.8254 0.2482 0.057 Uiso 1 1 calc R . . . .
F2 F 0.37087(8) 1.10095(12) -0.09316(17) 0.0742(4) Uani 1 1 d . . . . .
C21 C 0.38837(10) 0.94631(17) 0.0831(2) 0.0392(5) Uani 1 1 d . . . . .
C10 C 0.29208(10) 0.79987(16) 0.0555(2) 0.0378(4) Uani 1 1 d . . . . .
H10 H 0.2891 0.8148 0.1642 0.045 Uiso 1 1 calc R . . . .
N13 N 0.17254(10) 0.87810(16) 0.0150(2) 0.0463(4) Uani 1 1 d . . . . .
C2 C 0.21789(11) 0.45548(18) 0.1160(2) 0.0457(5) Uani 1 1 d . . . . .
H2A H 0.1845 0.5055 0.1586 0.055 Uiso 1 1 calc R . . . .
H2B H 0.2490 0.4190 0.2011 0.055 Uiso 1 1 calc R . . . .
C9 C 0.21593(10) 0.79235(16) -0.0374(2) 0.0379(4) Uani 1 1 d . . . . .
H9 H 0.2179 0.8050 -0.1470 0.045 Uiso 1 1 calc R . . . .
C19 C 0.07913(11) 0.8775(2) -0.2138(2) 0.0505(5) Uani 1 1 d . . . . .
H19 H 0.0932 0.8040 -0.2425 0.061 Uiso 1 1 calc R . . . .
C22 C 0.40887(11) 1.0549(2) 0.0374(3) 0.0501(5) Uani 1 1 d . . . . .
C14 C 0.11449(10) 0.92913(17) -0.0805(2) 0.0404(5) Uani 1 1 d . . . . .
C15 C 0.08986(11) 1.03715(19) -0.0425(3) 0.0482(5) Uani 1 1 d . . . . .
C5 C 0.27090(13) 0.3575(2) -0.1548(2) 0.0563(6) Uani 1 1 d . . . . .
H5A H 0.2401 0.3915 -0.2424 0.068 Uiso 1 1 calc R . . . .
H5B H 0.3050 0.3070 -0.1941 0.068 Uiso 1 1 calc R . . . .
C16 C 0.03443(13) 1.0942(2) -0.1310(3) 0.0621(6) Uani 1 1 d . . . . .
H16 H 0.0197 1.1670 -0.1018 0.075 Uiso 1 1 calc R . . . .
C17 C 0.00096(13) 1.0420(3) -0.2635(3) 0.0696(7) Uani 1 1 d . . . . .
H17 H -0.0367 1.0795 -0.3255 0.083 Uiso 1 1 calc R . . . .
C3 C 0.17675(12) 0.36236(19) 0.0161(3) 0.0545(6) Uani 1 1 d . . . . .
H3A H 0.1420 0.3993 -0.0623 0.065 Uiso 1 1 calc R . . . .
H3B H 0.1508 0.3142 0.0792 0.065 Uiso 1 1 calc R . . . .
C4 C 0.22614(13) 0.2860(2) -0.0613(3) 0.0606(6) Uani 1 1 d . . . . .
H4A H 0.2575 0.2425 0.0168 0.073 Uiso 1 1 calc R . . . .
H4B H 0.1978 0.2303 -0.1283 0.073 Uiso 1 1 calc R . . . .
C25 C 0.48501(12) 0.9597(2) 0.2960(3) 0.0610(6) Uani 1 1 d . . . . .
H25 H 0.5110 0.9272 0.3845 0.073 Uiso 1 1 calc R . . . .
C18 C 0.02327(12) 0.9342(2) -0.3042(3) 0.0621(6) Uani 1 1 d . . . . .
H18 H 0.0004 0.8988 -0.3940 0.075 Uiso 1 1 calc R . . . .
C23 C 0.46510(13) 1.1159(2) 0.1168(3) 0.0685(7) Uani 1 1 d . . . . .
H23 H 0.4773 1.1888 0.0827 0.082 Uiso 1 1 calc R . . . .
C24 C 0.50332(13) 1.0674(3) 0.2479(3) 0.0716(8) Uani 1 1 d . . . . .
H24 H 0.5415 1.1078 0.3037 0.086 Uiso 1 1 calc R . . . .
H20 H 0.3189(12) 0.909(2) -0.094(3) 0.056(7) Uiso 1 1 d . . . . .
H13 H 0.1844(13) 0.907(2) 0.103(3) 0.070(8) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O12 0.0526(8) 0.0401(8) 0.0358(7) 0.0052(6) -0.0036(6) -0.0047(6)
O7 0.0478(8) 0.0372(8) 0.0362(7) -0.0014(6) -0.0008(6) 0.0041(6)
O11 0.0372(7) 0.0405(8) 0.0510(8) 0.0046(7) 0.0037(6) -0.0006(6)
O8 0.0366(7) 0.0381(8) 0.0532(8) -0.0009(6) 0.0067(6) -0.0003(6)
C1 0.0401(10) 0.0365(10) 0.0317(9) 0.0021(8) -0.0014(8) -0.0008(8)
N20 0.0477(10) 0.0473(10) 0.0375(9) 0.0075(8) -0.0053(8) -0.0125(8)
F1 0.0733(9) 0.0524(8) 0.0791(10) -0.0160(7) -0.0019(8) 0.0037(7)
C6 0.0476(11) 0.0501(13) 0.0495(12) 0.0047(10) 0.0119(10) 0.0080(10)
C26 0.0438(11) 0.0540(13) 0.0438(11) -0.0024(10) 0.0007(9) -0.0023(10)
F2 0.0708(9) 0.0568(9) 0.0886(10) 0.0228(8) -0.0065(8) -0.0090(7)
C21 0.0359(10) 0.0404(11) 0.0412(10) -0.0051(9) 0.0057(8) -0.0026(8)
C10 0.0377(10) 0.0381(10) 0.0365(10) 0.0005(8) 0.0023(8) -0.0033(8)
N13 0.0467(10) 0.0452(10) 0.0440(10) -0.0079(9) -0.0019(8) 0.0092(8)
C2 0.0547(12) 0.0435(12) 0.0402(11) 0.0013(9) 0.0113(10) -0.0021(10)
C9 0.0350(9) 0.0362(10) 0.0403(10) 0.0012(8) -0.0002(8) -0.0019(8)
C19 0.0433(11) 0.0530(13) 0.0536(12) -0.0013(11) 0.0030(10) 0.0007(10)
C22 0.0427(11) 0.0454(12) 0.0605(14) 0.0003(11) 0.0029(10) -0.0013(10)
C14 0.0341(10) 0.0391(11) 0.0481(11) 0.0067(9) 0.0065(9) -0.0001(8)
C15 0.0424(11) 0.0433(12) 0.0586(13) 0.0009(11) 0.0074(10) -0.0013(10)
C5 0.0729(15) 0.0517(14) 0.0440(12) -0.0050(11) 0.0084(11) 0.0112(12)
C16 0.0551(14) 0.0498(14) 0.0811(18) 0.0090(13) 0.0094(13) 0.0125(11)
C17 0.0520(13) 0.0794(19) 0.0739(17) 0.0204(15) -0.0007(13) 0.0161(14)
C3 0.0562(13) 0.0476(13) 0.0593(13) 0.0013(11) 0.0077(11) -0.0096(11)
C4 0.0800(17) 0.0417(12) 0.0592(14) -0.0071(11) 0.0089(13) -0.0044(12)
C25 0.0459(12) 0.0787(18) 0.0541(13) -0.0096(13) -0.0052(10) -0.0042(12)
C18 0.0482(13) 0.0773(18) 0.0562(14) 0.0029(13) -0.0056(11) -0.0001(12)
C23 0.0594(15) 0.0538(15) 0.0914(19) -0.0048(14) 0.0092(14) -0.0210(12)
C24 0.0511(14) 0.081(2) 0.0780(17) -0.0235(16) -0.0032(13) -0.0211(13)

_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
O12 O11 1.4652(17) . ?
O12 C1 1.426(2) . ?
O7 O8 1.4680(17) . ?
O7 C1 1.427(2) . ?
O11 C10 1.448(2) . ?
O8 C9 1.446(2) . ?
C1 C6 1.514(3) . ?
C1 C2 1.512(3) . ?
N20 C21 1.396(2) . ?
N20 C10 1.404(2) . ?
F1 C15 1.360(2) . ?
C6 C5 1.515(3) . ?
C26 C21 1.387(3) . ?
C26 C25 1.379(3) . ?
F2 C22 1.360(2) . ?
C21 C22 1.383(3) . ?
C10 C9 1.541(3) . ?
N13 C9 1.405(2) . ?
N13 C14 1.400(3) . ?
C2 C3 1.517(3) . ?
C19 C14 1.385(3) . ?
C19 C18 1.379(3) . ?
C22 C23 1.367(3) . ?
C14 C15 1.383(3) . ?
C15 C16 1.368(3) . ?
C5 C4 1.512(3) . ?
C16 C17 1.371(3) . ?
C17 C18 1.373(4) . ?
C3 C4 1.518(3) . ?
C25 C24 1.367(4) . ?
C23 C24 1.376(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O12 O11 107.68(12) . . ?
C1 O7 O8 107.55(12) . . ?
C10 O11 O12 105.55(12) . . ?
C9 O8 O7 106.16(12) . . ?
O12 C1 O7 108.93(15) . . ?
O12 C1 C6 112.14(15) . . ?
O12 C1 C2 104.98(14) . . ?
O7 C1 C6 106.11(14) . . ?
O7 C1 C2 112.60(15) . . ?
C2 C1 C6 112.15(18) . . ?
C21 N20 C10 122.94(17) . . ?
C1 C6 C5 112.79(17) . . ?
C25 C26 C21 120.6(2) . . ?
C26 C21 N20 123.93(19) . . ?
C22 C21 N20 119.06(18) . . ?
C22 C21 C26 117.00(19) . . ?
O11 C10 C9 112.70(15) . . ?
N20 C10 O11 106.80(15) . . ?
N20 C10 C9 109.05(16) . . ?
C14 N13 C9 122.63(18) . . ?
C1 C2 C3 110.52(16) . . ?
O8 C9 C10 113.15(15) . . ?
N13 C9 O8 105.69(15) . . ?
N13 C9 C10 109.41(16) . . ?
C18 C19 C14 120.5(2) . . ?
F2 C22 C21 117.39(18) . . ?
F2 C22 C23 119.7(2) . . ?
C23 C22 C21 122.9(2) . . ?
C19 C14 N13 123.7(2) . . ?
C15 C14 N13 119.44(19) . . ?
C15 C14 C19 116.83(19) . . ?
F1 C15 C14 117.14(19) . . ?
F1 C15 C16 119.6(2) . . ?
C16 C15 C14 123.2(2) . . ?
C4 C5 C6 111.42(17) . . ?
C15 C16 C17 118.9(2) . . ?
C16 C17 C18 119.7(2) . . ?
C2 C3 C4 111.74(19) . . ?
C5 C4 C3 111.55(19) . . ?
C24 C25 C26 120.7(2) . . ?
C17 C18 C19 120.9(2) . . ?
C22 C23 C24 118.8(2) . . ?
C25 C24 C23 119.9(2) . . ?


####################################################################### 
# 
# 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_skr-135-3
_database_code_depnum_ccdc_archive 'CCDC 1905334'
loop_
_audit_author_name
_audit_author_address
'Ekaterina Mescheryakova'
;Institute of Petrochemistry and Catalysis
Russia
;
_audit_update_record             
;
2019-03-25 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;
_audit_creation_date             2019-02-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_systematic        
11-(2-fluorophenyl)-2,3,5,6-tetraoxa-11-azaspiro[bicyclo[5.3.1]undecane-4,1'-cyclohexane]
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H22 F N O4'
_chemical_formula_sum            'C17 H22 F N O4'
_chemical_formula_weight         323.36
_chemical_melting_point          ?
_exptl_crystal_description       prizm
_exptl_crystal_colour            orange
_diffrn_ambient_temperature      293(2)
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'

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

_cell_length_a                   6.4738(3)
_cell_length_b                   10.2056(9)
_cell_length_c                   12.4931(10)
_cell_angle_alpha                75.029(7)
_cell_angle_beta                 80.670(6)
_cell_angle_gamma                88.090(6)
_cell_volume                     786.81(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1778
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.1290
_cell_measurement_theta_min      3.0190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             344.0
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.38
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6506
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.279
_diffrn_reflns_theta_min         2.319
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1709
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -39.00   29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1042  -57.0000   30.0000 68

#__ type_ start__ end____ width___ exp.time_
  2 omega   -3.00   23.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.4011  -99.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -16.4011  -99.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega   35.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1042 -156.0000 -114.0000 54

#__ type_ start__ end____ width___ exp.time_
  5 omega   33.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1042 -178.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
  6 omega  -45.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1042    0.0000   60.0000 131
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0122143000
_diffrn_orient_matrix_UB_12      0.0708934000
_diffrn_orient_matrix_UB_13      -0.0069965000
_diffrn_orient_matrix_UB_21      0.0047298000
_diffrn_orient_matrix_UB_22      0.0092013000
_diffrn_orient_matrix_UB_23      -0.0585988000
_diffrn_orient_matrix_UB_31      -0.1102624000
_diffrn_orient_matrix_UB_32      -0.0081079000
_diffrn_orient_matrix_UB_33      0.0077923000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'XCalibur E'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2526
_reflns_number_total             3611
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+0.0778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1303
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008), C010(H010)
2.b Secondary CH2 refined with riding coordinates:
 C013(H01A,H01B), C014(H01C,H01D), C016(H01E,H01F), C017(H01G,H01H), C018(H01I,
 H01J), C020(H02A,H02B), C021(H02C,H02D), C023(H02E,H02F)
2.c Aromatic/amide H refined with riding coordinates:
 C007(H007), C015(H015), C019(H019), C022(H022)
;
_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
O001 O 0.40085(16) 0.80981(12) 0.15411(9) 0.0403(3) Uani 1 1 d . . . . .
O002 O 0.64578(16) 0.75358(12) 0.34102(9) 0.0385(3) Uani 1 1 d . . . . .
O003 O 0.28393(16) 0.72091(12) 0.25624(10) 0.0417(3) Uani 1 1 d . . . . .
O004 O 0.70832(15) 0.83418(11) 0.22576(9) 0.0357(3) Uani 1 1 d . . . . .
F005 F -0.02891(14) 1.03572(11) 0.37152(10) 0.0607(3) Uani 1 1 d . . . . .
N006 N 0.33976(19) 0.89463(14) 0.34549(11) 0.0360(3) Uani 1 1 d . . . . .
C007 C 0.5083(3) 1.11452(18) 0.24465(14) 0.0411(4) Uani 1 1 d . . . . .
H007 H 0.6369 1.0727 0.2332 0.049 Uiso 1 1 calc R . . . .
C008 C 0.5088(2) 0.83418(17) 0.40149(14) 0.0371(4) Uani 1 1 d . . . . .
H008 H 0.5907 0.9052 0.4157 0.045 Uiso 1 1 calc R . . . .
C009 C 0.3326(2) 1.03560(17) 0.29989(13) 0.0339(4) Uani 1 1 d . . . . .
C010 C 0.1898(2) 0.80470(17) 0.32769(15) 0.0384(4) Uani 1 1 d . . . . .
H010 H 0.0759 0.8574 0.2948 0.046 Uiso 1 1 calc R . . . .
C011 C 0.1469(2) 1.10606(18) 0.31353(15) 0.0414(4) Uani 1 1 d . . . . .
C012 C 0.6169(2) 0.77682(16) 0.15118(13) 0.0337(4) Uani 1 1 d . . . . .
C013 C 0.1014(3) 0.7026(2) 0.43549(16) 0.0494(5) Uani 1 1 d . . . . .
H01A H 0.0182 0.6355 0.4184 0.059 Uiso 1 1 calc R . . . .
H01B H 0.0103 0.7485 0.4836 0.059 Uiso 1 1 calc R . . . .
C014 C 0.6549(2) 0.62605(17) 0.17085(15) 0.0404(4) Uani 1 1 d . . . . .
H01C H 0.5842 0.5910 0.1211 0.048 Uiso 1 1 calc R . . . .
H01D H 0.5965 0.5805 0.2475 0.048 Uiso 1 1 calc R . . . .
C015 C 0.4955(3) 1.25391(19) 0.20647(16) 0.0493(5) Uani 1 1 d . . . . .
H015 H 0.6156 1.3044 0.1706 0.059 Uiso 1 1 calc R . . . .
C016 C 0.7202(3) 0.85677(18) 0.03584(14) 0.0414(4) Uani 1 1 d . . . . .
H01E H 0.7029 0.9530 0.0299 0.050 Uiso 1 1 calc R . . . .
H01F H 0.6520 0.8347 -0.0210 0.050 Uiso 1 1 calc R . . . .
C017 C 0.9913(3) 0.6738(2) 0.03434(17) 0.0534(5) Uani 1 1 d . . . . .
H01G H 1.1407 0.6571 0.0264 0.064 Uiso 1 1 calc R . . . .
H01H H 0.9367 0.6413 -0.0221 0.064 Uiso 1 1 calc R . . . .
C018 C 0.8873(3) 0.59585(18) 0.15007(16) 0.0448(4) Uani 1 1 d . . . . .
H01I H 0.9546 0.6198 0.2064 0.054 Uiso 1 1 calc R . . . .
H01J H 0.9059 0.4994 0.1574 0.054 Uiso 1 1 calc R . . . .
C019 C 0.1312(3) 1.24337(19) 0.27449(16) 0.0513(5) Uani 1 1 d . . . . .
H019 H 0.0024 1.2855 0.2841 0.062 Uiso 1 1 calc R . . . .
C020 C 0.4287(3) 0.7331(2) 0.51168(15) 0.0483(5) Uani 1 1 d . . . . .
H02A H 0.3599 0.7815 0.5647 0.058 Uiso 1 1 calc R . . . .
H02B H 0.5463 0.6849 0.5424 0.058 Uiso 1 1 calc R . . . .
C021 C 0.9536(3) 0.82482(19) 0.01474(16) 0.0476(5) Uani 1 1 d . . . . .
H02C H 1.0120 0.8702 -0.0620 0.057 Uiso 1 1 calc R . . . .
H02D H 1.0252 0.8596 0.0643 0.057 Uiso 1 1 calc R . . . .
C022 C 0.3078(3) 1.3188(2) 0.22079(17) 0.0541(5) Uani 1 1 d . . . . .
H022 H 0.3001 1.4125 0.1945 0.065 Uiso 1 1 calc R . . . .
C023 C 0.2758(3) 0.6315(2) 0.49734(17) 0.0535(5) Uani 1 1 d . . . . .
H02E H 0.2147 0.5764 0.5706 0.064 Uiso 1 1 calc R . . . .
H02F H 0.3505 0.5718 0.4555 0.064 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O001 0.0321(6) 0.0467(7) 0.0430(7) -0.0093(6) -0.0126(5) 0.0023(5)
O002 0.0358(6) 0.0446(7) 0.0369(6) -0.0111(5) -0.0122(5) 0.0104(5)
O003 0.0343(6) 0.0409(7) 0.0519(7) -0.0149(6) -0.0069(5) -0.0058(5)
O004 0.0327(6) 0.0387(7) 0.0395(6) -0.0150(5) -0.0085(5) -0.0003(5)
F005 0.0350(6) 0.0556(7) 0.0807(8) -0.0080(6) 0.0054(5) 0.0077(5)
N006 0.0285(7) 0.0374(8) 0.0454(8) -0.0121(6) -0.0133(6) 0.0036(5)
C007 0.0354(9) 0.0473(11) 0.0439(10) -0.0179(8) -0.0056(7) 0.0001(7)
C008 0.0311(8) 0.0437(10) 0.0419(9) -0.0162(8) -0.0140(7) 0.0067(7)
C009 0.0332(8) 0.0375(9) 0.0337(8) -0.0114(7) -0.0100(6) 0.0035(6)
C010 0.0285(8) 0.0400(9) 0.0493(10) -0.0135(8) -0.0107(7) 0.0021(7)
C011 0.0338(9) 0.0446(10) 0.0440(10) -0.0089(8) -0.0058(7) 0.0043(7)
C012 0.0314(8) 0.0353(9) 0.0394(9) -0.0142(7) -0.0131(7) 0.0026(6)
C013 0.0366(10) 0.0529(12) 0.0559(12) -0.0091(10) -0.0068(8) -0.0039(8)
C014 0.0445(10) 0.0345(9) 0.0454(10) -0.0128(8) -0.0126(8) -0.0007(7)
C015 0.0521(11) 0.0472(12) 0.0483(11) -0.0113(9) -0.0063(8) -0.0121(9)
C016 0.0481(10) 0.0365(10) 0.0414(10) -0.0105(8) -0.0117(8) 0.0023(7)
C017 0.0536(11) 0.0533(12) 0.0563(12) -0.0234(10) -0.0041(9) 0.0117(9)
C018 0.0489(10) 0.0351(10) 0.0548(11) -0.0175(8) -0.0129(8) 0.0101(7)
C019 0.0498(11) 0.0463(11) 0.0570(12) -0.0105(9) -0.0135(9) 0.0147(8)
C020 0.0455(10) 0.0607(12) 0.0387(10) -0.0104(9) -0.0126(8) 0.0110(9)
C021 0.0462(10) 0.0489(11) 0.0444(10) -0.0103(9) 0.0002(8) -0.0007(8)
C022 0.0652(13) 0.0395(11) 0.0573(12) -0.0076(9) -0.0178(10) 0.0064(9)
C023 0.0531(11) 0.0505(12) 0.0502(11) -0.0006(9) -0.0087(9) 0.0006(9)

_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
O001 O003 1.4692(15) . ?
O001 C012 1.4249(18) . ?
O002 O004 1.4613(15) . ?
O002 C008 1.4453(18) . ?
O003 C010 1.443(2) . ?
O004 C012 1.4298(18) . ?
F005 C011 1.3619(18) . ?
N006 C008 1.431(2) . ?
N006 C009 1.406(2) . ?
N006 C010 1.438(2) . ?
C007 C009 1.392(2) . ?
C007 C015 1.383(2) . ?
C008 C020 1.516(2) . ?
C009 C011 1.389(2) . ?
C010 C013 1.514(2) . ?
C011 C019 1.366(2) . ?
C012 C014 1.512(2) . ?
C012 C016 1.518(2) . ?
C013 C023 1.529(3) . ?
C014 C018 1.520(2) . ?
C015 C022 1.372(3) . ?
C016 C021 1.530(2) . ?
C017 C018 1.517(3) . ?
C017 C021 1.515(3) . ?
C019 C022 1.376(3) . ?
C020 C023 1.520(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
C012 O001 O003 107.87(11) . . ?
C008 O002 O004 108.56(11) . . ?
C010 O003 O001 108.09(11) . . ?
C012 O004 O002 109.38(10) . . ?
C008 N006 C010 117.33(13) . . ?
C009 N006 C008 121.08(13) . . ?
C009 N006 C010 121.29(13) . . ?
C015 C007 C009 121.30(16) . . ?
O002 C008 C020 103.11(13) . . ?
N006 C008 O002 113.94(13) . . ?
N006 C008 C020 111.21(13) . . ?
C007 C009 N006 123.40(14) . . ?
C011 C009 N006 120.85(14) . . ?
C011 C009 C007 115.66(16) . . ?
O003 C010 C013 103.39(14) . . ?
N006 C010 O003 112.08(12) . . ?
N006 C010 C013 111.94(15) . . ?
F005 C011 C009 118.66(15) . . ?
F005 C011 C019 117.65(15) . . ?
C019 C011 C009 123.67(16) . . ?
O001 C012 O004 111.25(12) . . ?
O001 C012 C014 112.52(13) . . ?
O001 C012 C016 104.19(13) . . ?
O004 C012 C014 112.42(13) . . ?
O004 C012 C016 103.30(12) . . ?
C014 C012 C016 112.51(14) . . ?
C010 C013 C023 111.26(14) . . ?
C012 C014 C018 111.26(13) . . ?
C022 C015 C007 120.87(17) . . ?
C012 C016 C021 111.24(14) . . ?
C021 C017 C018 111.65(15) . . ?
C017 C018 C014 111.82(15) . . ?
C011 C019 C022 119.33(17) . . ?
C008 C020 C023 111.95(15) . . ?
C017 C021 C016 111.78(14) . . ?
C015 C022 C019 119.16(18) . . ?
C020 C023 C013 111.43(16) . . ?

####################################################################### 
# 
# 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_iir-303-7
_database_code_depnum_ccdc_archive 'CCDC 1905327'
loop_
_audit_author_name
_audit_author_address
'Ekaterina Mescheryakova'
;Institute of Petrochemistry and Catalysis
Russia
;
_audit_update_record             
;
2019-03-25 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;
_audit_creation_date             2018-04-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelxl_version_number           2013-4
_chemical_name_systematic        
9-N,10-N-bis(4-chlorophenyl)-7,8,11,12-tetraoxaspiro[5.6]dodecane-9,10-diamine
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H22 Cl2 N2 O4'
_chemical_formula_sum            'C20 H22 Cl2 N2 O4'
_chemical_formula_weight         425.30
_exptl_crystal_recrystallization_method hexane/Et2O
_chemical_melting_point          ?
_exptl_crystal_description       prizm
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293(2)
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration ?
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                   10.5362(9)
_cell_length_b                   9.4705(6)
_cell_length_c                   20.3165(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.462(8)
_cell_angle_gamma                90
_cell_volume                     1999.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3198
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.7810
_cell_measurement_theta_min      2.3840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             888.0
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.28
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13245
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.281
_diffrn_reflns_theta_min         2.032
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1709
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -1.00   76.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -       16.8699   38.0000  -30.0000 77

#__ type_ start__ end____ width___ exp.time_
  2 omega   24.00   86.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -       16.8699    0.0000 -150.0000 62

#__ type_ start__ end____ width___ exp.time_
  3 omega  -14.00   22.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -      -16.0886  -99.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00  -14.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -       16.8699    0.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -43.00   50.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -      -16.0886   77.0000 -180.0000 93

#__ type_ start__ end____ width___ exp.time_
  6 omega  -84.00  -69.00   1.0000   25.1900
omega____ theta____ kappa____ phi______ frames
    -      -16.0886  -77.0000   60.0000 15
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0662341000
_diffrn_orient_matrix_UB_12      -0.0158695000
_diffrn_orient_matrix_UB_13      -0.0096882000
_diffrn_orient_matrix_UB_21      -0.0063124000
_diffrn_orient_matrix_UB_22      -0.0087330000
_diffrn_orient_matrix_UB_23      0.0339996000
_diffrn_orient_matrix_UB_31      -0.0152781000
_diffrn_orient_matrix_UB_32      0.0726195000
_diffrn_orient_matrix_UB_33      0.0019778000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'XCalibur E'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2780
_reflns_number_total             4644
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4644
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0608
_refine_ls_restrained_S_all      0.987
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1582
_refine_ls_wR_factor_ref         0.1916
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C3(H3A,H3B), C6(H6A,H6B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N20(H20), N13(H13), C22(H22), C15(H15), C19(H19), C16(H16), C23(H23),
 C18(H18), C26(H26), C25(H25)
;
_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
Cl2 Cl 0.68429(8) 0.30143(9) 0.09422(4) 0.0632(3) Uani 1 1 d . . . . .
Cl1 Cl 0.96882(9) -0.80129(9) 0.43986(5) 0.0733(3) Uani 1 1 d . . . . .
O12 O 1.32719(17) 0.09754(18) 0.33024(8) 0.0415(5) Uani 1 1 d . . . . .
O11 O 1.18892(17) 0.08545(17) 0.33155(9) 0.0434(5) Uani 1 1 d . . . . .
O7 O 1.34833(19) -0.04645(19) 0.42436(9) 0.0490(5) Uani 1 1 d . . . . .
O8 O 1.33368(18) -0.16133(18) 0.37589(10) 0.0481(5) Uani 1 1 d . . . . .
N20 N 1.0146(2) -0.0504(2) 0.29288(11) 0.0461(6) Uani 1 1 d . . . . .
H20 H 0.9757 -0.1045 0.3171 0.055 Uiso 1 1 calc R . . . .
C21 C 0.9396(3) 0.0337(3) 0.24478(13) 0.0406(6) Uani 1 1 d . . . . .
N13 N 1.1766(2) -0.3027(2) 0.31924(11) 0.0477(6) Uani 1 1 d . . . . .
H13 H 1.1911 -0.3100 0.2789 0.057 Uiso 1 1 calc R . . . .
C22 C 0.9895(3) 0.1036(3) 0.19462(13) 0.0433(6) Uani 1 1 d . . . . .
H22 H 1.0767 0.0960 0.1924 0.052 Uiso 1 1 calc R . . . .
C24 C 0.7832(3) 0.1965(3) 0.15221(14) 0.0459(7) Uani 1 1 d . . . . .
C14 C 1.1337(2) -0.4211(3) 0.34946(13) 0.0399(6) Uani 1 1 d . . . . .
C9 C 1.1974(3) -0.1717(3) 0.35161(13) 0.0407(6) Uani 1 1 d . . . . .
H9 H 1.1508 -0.1693 0.3895 0.049 Uiso 1 1 calc R . . . .
C1 C 1.3961(3) 0.0762(3) 0.39625(12) 0.0402(6) Uani 1 1 d . . . . .
C17 C 1.0347(3) -0.6551(3) 0.40554(15) 0.0479(7) Uani 1 1 d . . . . .
C15 C 1.1481(3) -0.4370(3) 0.41791(14) 0.0489(7) Uani 1 1 d . . . . .
H15 H 1.1918 -0.3683 0.4455 0.059 Uiso 1 1 calc R . . . .
C19 C 1.0732(3) -0.5295(3) 0.30983(14) 0.0469(7) Uani 1 1 d . . . . .
H19 H 1.0666 -0.5239 0.2637 0.056 Uiso 1 1 calc R . . . .
C16 C 1.0983(3) -0.5542(3) 0.44608(14) 0.0518(7) Uani 1 1 d . . . . .
H16 H 1.1083 -0.5636 0.4922 0.062 Uiso 1 1 calc R . . . .
C23 C 0.9111(3) 0.1841(3) 0.14826(14) 0.0460(7) Uani 1 1 d . . . . .
H23 H 0.9449 0.2297 0.1145 0.055 Uiso 1 1 calc R . . . .
C10 C 1.1497(2) -0.0516(3) 0.30377(13) 0.0403(6) Uani 1 1 d . . . . .
H10 H 1.1811 -0.0648 0.2614 0.048 Uiso 1 1 calc R . . . .
C2 C 1.3743(3) 0.1915(3) 0.44410(14) 0.0539(8) Uani 1 1 d . . . . .
H2A H 1.4107 0.1631 0.4891 0.065 Uiso 1 1 calc R . . . .
H2B H 1.2825 0.2049 0.4424 0.065 Uiso 1 1 calc R . . . .
C18 C 1.0232(3) -0.6441(3) 0.33764(15) 0.0530(8) Uani 1 1 d . . . . .
H18 H 0.9814 -0.7145 0.3104 0.064 Uiso 1 1 calc R . . . .
C26 C 0.8095(3) 0.0473(3) 0.24704(16) 0.0572(8) Uani 1 1 d . . . . .
H26 H 0.7743 0.0001 0.2799 0.069 Uiso 1 1 calc R . . . .
C4 C 1.5754(4) 0.3123(3) 0.42272(19) 0.0740(12) Uani 1 1 d . . . . .
H4A H 1.6223 0.2828 0.4657 0.089 Uiso 1 1 calc R . . . .
H4B H 1.6106 0.4020 0.4113 0.089 Uiso 1 1 calc R . . . .
C3 C 1.4350(4) 0.3306(3) 0.42766(18) 0.0658(10) Uani 1 1 d . . . . .
H3A H 1.3894 0.3666 0.3856 0.079 Uiso 1 1 calc R . . . .
H3B H 1.4267 0.3994 0.4621 0.079 Uiso 1 1 calc R . . . .
C25 C 0.7320(3) 0.1294(4) 0.20156(17) 0.0595(8) Uani 1 1 d . . . . .
H25 H 0.6451 0.1394 0.2041 0.071 Uiso 1 1 calc R . . . .
C6 C 1.5343(3) 0.0629(3) 0.38649(15) 0.0508(7) Uani 1 1 d . . . . .
H6A H 1.5392 -0.0029 0.3504 0.061 Uiso 1 1 calc R . . . .
H6B H 1.5846 0.0244 0.4268 0.061 Uiso 1 1 calc R . . . .
C5 C 1.5929(3) 0.2034(3) 0.37041(17) 0.0633(9) Uani 1 1 d . . . . .
H5A H 1.6838 0.1910 0.3691 0.076 Uiso 1 1 calc R . . . .
H5B H 1.5515 0.2360 0.3269 0.076 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl2 0.0545(5) 0.0752(6) 0.0568(5) 0.0067(4) 0.0000(4) 0.0137(4)
Cl1 0.0759(7) 0.0637(5) 0.0803(6) 0.0080(4) 0.0130(5) -0.0203(4)
O12 0.0339(10) 0.0489(10) 0.0398(10) 0.0031(8) 0.0008(8) -0.0018(8)
O11 0.0326(10) 0.0438(10) 0.0527(11) -0.0018(8) 0.0039(8) 0.0018(8)
O7 0.0569(13) 0.0462(10) 0.0413(10) 0.0044(8) 0.0006(9) -0.0057(9)
O8 0.0412(11) 0.0408(10) 0.0605(12) 0.0001(8) 0.0026(9) 0.0048(8)
N20 0.0344(12) 0.0517(13) 0.0524(13) 0.0095(11) 0.0075(10) -0.0027(10)
C21 0.0347(14) 0.0386(13) 0.0474(15) -0.0046(11) 0.0036(11) -0.0043(11)
N13 0.0586(16) 0.0409(12) 0.0457(13) -0.0032(10) 0.0144(11) -0.0047(10)
C22 0.0310(14) 0.0466(15) 0.0530(16) -0.0031(12) 0.0089(12) -0.0029(11)
C24 0.0378(15) 0.0460(15) 0.0513(16) -0.0046(12) -0.0009(12) -0.0009(12)
C14 0.0338(14) 0.0393(13) 0.0462(15) -0.0014(11) 0.0054(11) 0.0048(11)
C9 0.0391(15) 0.0409(14) 0.0428(14) -0.0005(11) 0.0092(11) 0.0013(11)
C1 0.0416(15) 0.0398(13) 0.0371(13) 0.0038(11) -0.0002(11) 0.0001(11)
C17 0.0461(17) 0.0432(14) 0.0539(17) 0.0025(12) 0.0068(13) 0.0010(12)
C15 0.0513(17) 0.0434(15) 0.0495(16) -0.0046(12) 0.0008(13) -0.0024(13)
C19 0.0509(17) 0.0447(15) 0.0447(15) -0.0084(12) 0.0064(12) 0.0005(12)
C16 0.0562(19) 0.0544(17) 0.0438(15) 0.0007(13) 0.0054(13) 0.0015(14)
C23 0.0404(16) 0.0500(15) 0.0477(16) -0.0011(12) 0.0079(12) -0.0033(12)
C10 0.0353(14) 0.0416(14) 0.0441(14) -0.0037(11) 0.0069(11) -0.0011(11)
C2 0.057(2) 0.0558(18) 0.0467(17) -0.0064(13) 0.0017(14) 0.0020(14)
C18 0.0540(19) 0.0407(15) 0.0621(19) -0.0090(13) 0.0029(15) -0.0022(13)
C26 0.0366(16) 0.0697(19) 0.0667(19) 0.0167(15) 0.0127(14) -0.0044(14)
C4 0.073(3) 0.056(2) 0.082(2) 0.0105(17) -0.017(2) -0.0171(17)
C3 0.075(3) 0.0457(16) 0.071(2) -0.0065(15) -0.0040(19) 0.0004(16)
C25 0.0291(15) 0.074(2) 0.075(2) 0.0120(17) 0.0087(14) 0.0009(14)
C6 0.0431(16) 0.0547(16) 0.0513(16) 0.0031(13) -0.0021(13) 0.0043(13)
C5 0.0498(19) 0.070(2) 0.068(2) 0.0124(17) 0.0035(16) -0.0105(15)

_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
Cl2 C24 1.749(3) . ?
Cl1 C17 1.745(3) . ?
O12 O11 1.466(2) . ?
O12 C1 1.431(3) . ?
O11 C10 1.448(3) . ?
O7 O8 1.458(3) . ?
O7 C1 1.422(3) . ?
O8 C9 1.443(3) . ?
N20 C21 1.400(3) . ?
N20 C10 1.405(3) . ?
C21 C22 1.389(4) . ?
C21 C26 1.384(4) . ?
N13 C14 1.389(3) . ?
N13 C9 1.405(3) . ?
C22 C23 1.376(4) . ?
C24 C23 1.368(4) . ?
C24 C25 1.371(4) . ?
C14 C15 1.382(4) . ?
C14 C19 1.393(3) . ?
C9 C10 1.526(3) . ?
C1 C2 1.505(4) . ?
C1 C6 1.507(4) . ?
C17 C16 1.364(4) . ?
C17 C18 1.369(4) . ?
C15 C16 1.390(4) . ?
C19 C18 1.368(4) . ?
C2 C3 1.526(5) . ?
C26 C25 1.370(4) . ?
C4 C3 1.509(5) . ?
C4 C5 1.513(5) . ?
C6 C5 1.524(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O12 O11 108.95(18) . . ?
C10 O11 O12 106.46(16) . . ?
C1 O7 O8 110.07(18) . . ?
C9 O8 O7 105.68(18) . . ?
C21 N20 C10 123.8(2) . . ?
C22 C21 N20 123.0(2) . . ?
C26 C21 N20 118.6(3) . . ?
C26 C21 C22 118.5(2) . . ?
C14 N13 C9 122.9(2) . . ?
C23 C22 C21 120.6(3) . . ?
C23 C24 Cl2 119.6(2) . . ?
C23 C24 C25 120.9(3) . . ?
C25 C24 Cl2 119.6(2) . . ?
N13 C14 C19 119.4(2) . . ?
C15 C14 N13 122.8(2) . . ?
C15 C14 C19 117.8(3) . . ?
O8 C9 C10 111.8(2) . . ?
N13 C9 O8 106.8(2) . . ?
N13 C9 C10 110.5(2) . . ?
O12 C1 C2 113.3(2) . . ?
O12 C1 C6 103.9(2) . . ?
O7 C1 O12 109.47(18) . . ?
O7 C1 C2 103.4(2) . . ?
O7 C1 C6 113.5(2) . . ?
C2 C1 C6 113.5(2) . . ?
C16 C17 Cl1 120.2(2) . . ?
C16 C17 C18 120.6(3) . . ?
C18 C17 Cl1 119.2(2) . . ?
C14 C15 C16 121.0(2) . . ?
C18 C19 C14 121.1(3) . . ?
C17 C16 C15 119.5(3) . . ?
C24 C23 C22 119.6(3) . . ?
O11 C10 C9 112.13(19) . . ?
N20 C10 O11 105.73(19) . . ?
N20 C10 C9 109.0(2) . . ?
C1 C2 C3 111.8(3) . . ?
C19 C18 C17 120.0(3) . . ?
C25 C26 C21 120.9(3) . . ?
C3 C4 C5 111.0(3) . . ?
C4 C3 C2 111.5(3) . . ?
C26 C25 C24 119.6(3) . . ?
C1 C6 C5 112.9(2) . . ?
C4 C5 C6 110.1(3) . . ?


####################################################################### 
# 
# 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_iir-297-13_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 1905337'
loop_
_audit_author_name
_audit_author_address
'Ekaterina Mescheryakova'
;Institute of Petrochemistry and Catalysis
Russia
;
_audit_update_record             
;
2019-03-25 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;
_audit_creation_date             2019-02-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_systematic        7,8,11-trioxaspiro[5.6]dodecane-9,10-diol
_chemical_name_common            ?
_chemical_formula_moiety         'C8 H14 O6'
_chemical_formula_sum            'C8 H14 O6'
_chemical_formula_weight         206.19
_chemical_melting_point          ?
_exptl_crystal_description       prizm
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_chemical_absolute_configuration ?
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.5986(6)
_cell_length_b                   9.8591(8)
_cell_length_c                   29.604(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1925.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1039
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.1750
_cell_measurement_theta_min      2.7480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             880.0
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0626
_diffrn_reflns_Laue_measured_fraction_max 0.739
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            4693
_diffrn_reflns_point_group_measured_fraction_max 0.739
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.051
_diffrn_reflns_theta_min         2.752
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1709
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -24.00   23.00   0.5000   25.1550
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega   46.00   82.00   0.5000   25.1550
omega____ theta____ kappa____ phi______ frames
    -       16.9480   57.0000   60.0000 72

#__ type_ start__ end____ width___ exp.time_
  3 omega    8.00   78.00   0.5000   25.1550
omega____ theta____ kappa____ phi______ frames
    -       16.9480   57.0000  -30.0000 140
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0943885000
_diffrn_orient_matrix_UB_12      -0.0227918000
_diffrn_orient_matrix_UB_13      -0.0085252000
_diffrn_orient_matrix_UB_21      -0.0433968000
_diffrn_orient_matrix_UB_22      -0.0073917000
_diffrn_orient_matrix_UB_23      -0.0217850000
_diffrn_orient_matrix_UB_31      0.0272571000
_diffrn_orient_matrix_UB_32      0.0678509000
_diffrn_orient_matrix_UB_33      -0.0052483000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.9782 5493 538
2 0.0218 5421 538

_diffrn_oxdiff_twin_integration_method simultaneous
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'XCalibur E'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                750
_reflns_number_total             1905
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1905
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1975
_refine_ls_R_factor_gt           0.0921
_refine_ls_restrained_S_all      0.975
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1401P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2133
_refine_ls_wR_factor_ref         0.2743
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005), C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C010(H01A,H01B), C011(H01C,H01D), C012(H01E,H01F), C013(H01G,H01H), C014(H01I,
 H01J)
2.c Idealised tetrahedral OH refined as rotating group:
 O002(H002), O003(H003)
;
_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
O001 O 0.4000(5) 0.8902(3) 0.10685(14) 0.0730(11) Uani 1 1 d . . . . .
O002 O 0.6016(4) 0.8605(3) 0.04689(12) 0.0593(9) Uani 1 1 d . . . . .
H002 H 0.6930 0.9023 0.0595 0.089 Uiso 1 1 calc GR . . . .
O003 O 0.2479(5) 0.8809(3) -0.01046(12) 0.0632(10) Uani 1 1 d . . . . .
H003 H 0.2293 0.8177 -0.0280 0.095 Uiso 1 1 calc GR . . . .
O004 O 0.0728(5) 0.8093(3) 0.05889(13) 0.0834(13) Uani 1 1 d . . . . .
C005 C 0.4201(6) 0.9160(4) 0.05829(12) 0.0388(9) Uani 1 1 d . . . . .
H005 H 0.4120 1.0127 0.0509 0.047 Uiso 1 1 calc R . . . .
O006 O 0.2693(5) 0.9945(3) 0.12257(12) 0.0711(11) Uani 1 1 d . . . . .
O007 O 0.0154(5) 0.9431(4) 0.07279(14) 0.0812(12) Uani 1 1 d . . . . .
C008 C 0.2635(5) 0.8316(4) 0.03292(14) 0.0466(10) Uani 1 1 d . . . . .
H008 H 0.3246 0.7415 0.0298 0.056 Uiso 1 1 calc R . . . .
C009 C 0.0646(5) 0.9447(6) 0.12006(14) 0.0564(13) Uani 1 1 d . . . . .
C010 C 0.0104(8) 0.8241(5) 0.14762(19) 0.0722(16) Uani 1 1 d . . . . .
H01A H 0.0962 0.7487 0.1388 0.087 Uiso 1 1 calc R . . . .
H01B H -0.1288 0.7990 0.1412 0.087 Uiso 1 1 calc R . . . .
C011 C -0.0471(8) 1.0665(6) 0.1359(2) 0.0790(16) Uani 1 1 d . . . . .
H01C H -0.0018 1.1451 0.1189 0.095 Uiso 1 1 calc R . . . .
H01D H -0.1907 1.0544 0.1301 0.095 Uiso 1 1 calc R . . . .
C012 C 0.0329(10) 0.8474(5) 0.19737(18) 0.0783(16) Uani 1 1 d . . . . .
H01E H 0.1755 0.8561 0.2048 0.094 Uiso 1 1 calc R . . . .
H01F H -0.0205 0.7700 0.2137 0.094 Uiso 1 1 calc R . . . .
C013 C -0.0806(9) 0.9771(6) 0.21230(18) 0.0841(18) Uani 1 1 d . . . . .
H01G H -0.2255 0.9639 0.2090 0.101 Uiso 1 1 calc R . . . .
H01H H -0.0522 0.9957 0.2438 0.101 Uiso 1 1 calc R . . . .
C014 C -0.0155(11) 1.0912(5) 0.1847(2) 0.0854(18) Uani 1 1 d . . . . .
H01I H 0.1272 1.1083 0.1901 0.102 Uiso 1 1 calc R . . . .
H01J H -0.0904 1.1715 0.1936 0.102 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O001 0.0541(19) 0.070(2) 0.095(3) -0.0160(17) -0.0240(19) 0.0084(16)
O002 0.0243(13) 0.0632(17) 0.090(2) -0.0279(15) -0.0020(15) -0.0020(12)
O003 0.085(2) 0.0473(17) 0.057(2) 0.0059(12) -0.0098(16) -0.0157(15)
O004 0.071(2) 0.063(2) 0.117(4) 0.012(2) -0.047(2) -0.0240(19)
C005 0.040(2) 0.0452(19) 0.031(2) -0.0133(16) 0.0037(15) -0.0020(16)
O006 0.054(2) 0.0457(17) 0.114(3) -0.0119(16) -0.0253(18) -0.0072(13)
O007 0.0399(19) 0.083(3) 0.121(3) 0.014(2) -0.030(2) 0.0043(18)
C008 0.0250(18) 0.050(2) 0.065(3) 0.010(2) -0.0062(16) 0.0019(15)
C009 0.0254(19) 0.109(4) 0.035(2) -0.012(2) -0.0054(17) -0.014(2)
C010 0.062(3) 0.057(3) 0.098(4) -0.027(3) -0.028(3) 0.018(2)
C011 0.065(3) 0.066(3) 0.106(5) 0.015(3) -0.008(3) -0.016(3)
C012 0.091(4) 0.059(3) 0.085(4) 0.006(2) 0.008(3) -0.005(3)
C013 0.083(4) 0.106(5) 0.063(4) -0.008(3) 0.012(3) 0.014(3)
C014 0.127(5) 0.047(3) 0.082(4) 0.001(2) -0.018(4) -0.006(3)

_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
O001 C005 1.466(6) . ?
O001 O006 1.420(5) . ?
O002 C005 1.359(5) . ?
O003 C008 1.377(6) . ?
O004 O007 1.432(6) . ?
O004 C008 1.491(5) . ?
C005 C008 1.524(5) . ?
O006 C009 1.439(5) . ?
O007 C009 1.437(5) . ?
C009 C010 1.486(8) . ?
C009 C011 1.484(8) . ?
C010 C012 1.498(7) . ?
C011 C014 1.480(8) . ?
C012 C013 1.546(8) . ?
C013 C014 1.456(8) . ?

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
O006 O001 C005 104.5(3) . . ?
O007 O004 C008 103.6(3) . . ?
O001 C005 C008 109.1(3) . . ?
O002 C005 O001 104.7(3) . . ?
O002 C005 C008 104.8(3) . . ?
O001 O006 C009 107.8(3) . . ?
O004 O007 C009 103.3(3) . . ?
O003 C008 O004 118.0(3) . . ?
O003 C008 C005 108.5(3) . . ?
O004 C008 C005 113.5(3) . . ?
O006 C009 C010 118.1(4) . . ?
O006 C009 C011 100.0(4) . . ?
O007 C009 O006 105.4(3) . . ?
O007 C009 C010 118.1(4) . . ?
O007 C009 C011 101.8(4) . . ?
C011 C009 C010 110.8(4) . . ?
C009 C010 C012 113.1(4) . . ?
C014 C011 C009 111.8(5) . . ?
C010 C012 C013 111.1(4) . . ?
C014 C013 C012 109.6(5) . . ?
C013 C014 C011 112.3(5) . . ?


####################################################################### 
# 
# 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_skr-57-2
_database_code_depnum_ccdc_archive 'CCDC 1905341'
loop_
_audit_author_name
_audit_author_address
'Ekaterina Mescheryakova'
;Institute of Petrochemistry and Catalysis
Russia
;
_audit_update_record             
;
2019-03-25 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;
_audit_creation_date             2019-02-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_systematic        
9-N,10-N-bis(4-bromophenyl)-7,8,11,12-tetraoxaspiro[5.6]dodecane-9,10-diamine
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H22 Br2 N2 O4'
_chemical_formula_sum            'C20 H22 Br2 N2 O4'
_chemical_formula_weight         514.20
_exptl_crystal_recrystallization_method hexane/Et2O
_chemical_melting_point          ?
_exptl_crystal_description       prizm
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293(2)
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration ?
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                   10.6640(6)
_cell_length_b                   9.4362(6)
_cell_length_c                   20.7558(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.997(5)
_cell_angle_gamma                90
_cell_volume                     2068.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1818
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.6770
_cell_measurement_theta_min      2.4000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.948
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.651
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1032.0
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0523
_diffrn_reflns_av_unetI/netI     0.1541
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.858
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            9852
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.177
_diffrn_reflns_theta_min         1.982
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1709
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -7.00   85.00   1.0000   28.1800
omega____ theta____ kappa____ phi______ frames
    -       16.9480   77.0000  -60.0000 92

#__ type_ start__ end____ width___ exp.time_
  2 omega    6.00   84.00   1.0000   28.1800
omega____ theta____ kappa____ phi______ frames
    -       16.9480   57.0000 -150.0000 78

#__ type_ start__ end____ width___ exp.time_
  3 omega   26.00   55.00   1.0000   28.1800
omega____ theta____ kappa____ phi______ frames
    -       16.9480  -99.0000  120.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega  -63.00  -38.00   1.0000   28.1800
omega____ theta____ kappa____ phi______ frames
    -      -16.2449 -178.0000  150.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0408304000
_diffrn_orient_matrix_UB_12      0.0166419000
_diffrn_orient_matrix_UB_13      0.0231484000
_diffrn_orient_matrix_UB_21      0.0533447000
_diffrn_orient_matrix_UB_22      0.0117099000
_diffrn_orient_matrix_UB_23      0.0238806000
_diffrn_orient_matrix_UB_31      0.0007398000
_diffrn_orient_matrix_UB_32      0.0723387000
_diffrn_orient_matrix_UB_33      -0.0092104000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'XCalibur E'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2039
_reflns_number_total             4798
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4798
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1914
_refine_ls_R_factor_gt           0.0749
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0474P)²+0.9755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1777
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B), C6(H6A,H6B), C4(H4A,H4B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N13(H13), C19(H19), N20(H20), C23(H23), C22(H22), C16(H16), C15(H15),
 C26(H26), C25(H25), C18(H18)
;
_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
Br01 Br 0.03863(9) 0.68256(9) 0.05817(5) 0.0739(3) Uani 1 1 d . . . . .
Br02 Br 0.31629(8) 1.79206(9) 0.40764(4) 0.0629(3) Uani 1 1 d . . . . .
O11 O -0.1899(4) 1.5834(5) 0.1694(2) 0.0482(13) Uani 1 1 d . . . . .
C3 C 0.4129(8) 1.6981(8) 0.1333(4) 0.070(2) Uani 1 1 d . . . . .
H3A H 0.4531 1.7327 0.1751 0.084 Uiso 1 1 calc R . . . .
H3B H 0.3234 1.6851 0.1358 0.084 Uiso 1 1 calc R . . . .
O12 O -0.3272(4) 1.5954(5) 0.1713(2) 0.0492(13) Uani 1 1 d . . . . .
O7 O -0.3450(5) 1.4480(5) 0.0798(2) 0.0589(14) Uani 1 1 d . . . . .
C17 C -0.0321(7) 0.8412(7) 0.0974(4) 0.0498(19) Uani 1 1 d . . . . .
O8 O -0.3314(5) 1.3348(5) 0.1278(2) 0.0567(13) Uani 1 1 d . . . . .
C24 C 0.2069(7) 1.6856(7) 0.3443(3) 0.0475(19) Uani 1 1 d . . . . .
N13 N -0.1764(6) 1.1951(6) 0.1819(3) 0.0562(17) Uani 1 1 d . . . . .
H13 H -0.1917 1.1882 0.2214 0.067 Uiso 1 1 calc R . . . .
C21 C 0.0542(7) 1.5295(7) 0.2538(3) 0.0443(18) Uani 1 1 d . . . . .
C19 C -0.1452(7) 1.0606(7) 0.0864(4) 0.054(2) Uani 1 1 d . . . . .
H19 H -0.1878 1.1302 0.0602 0.065 Uiso 1 1 calc R . . . .
N20 N -0.0194(6) 1.4490(6) 0.2067(3) 0.0542(16) Uani 1 1 d . . . . .
H20 H 0.0191 1.3973 0.1816 0.065 Uiso 1 1 calc R . . . .
C23 C 0.0815(7) 1.6762(8) 0.3478(4) 0.051(2) Uani 1 1 d . . . . .
H23 H 0.0479 1.7226 0.3811 0.062 Uiso 1 1 calc R . . . .
C10 C -0.1542(7) 1.4464(7) 0.1974(3) 0.0479(19) Uani 1 1 d . . . . .
H10 H -0.1868 1.4336 0.2389 0.057 Uiso 1 1 calc R . . . .
C9 C -0.1965(7) 1.3254(7) 0.1507(4) 0.0466(18) Uani 1 1 d . . . . .
H9 H -0.1491 1.3291 0.1135 0.056 Uiso 1 1 calc R . . . .
C14 C -0.1326(6) 1.0751(7) 0.1527(4) 0.0459(18) Uani 1 1 d . . . . .
C22 C 0.0027(7) 1.5981(8) 0.3022(3) 0.0484(19) Uani 1 1 d . . . . .
H22 H -0.0836 1.5923 0.3044 0.058 Uiso 1 1 calc R . . . .
C16 C -0.0221(7) 0.8532(8) 0.1636(4) 0.057(2) Uani 1 1 d . . . . .
H16 H 0.0196 0.7837 0.1902 0.069 Uiso 1 1 calc R . . . .
C15 C -0.0733(7) 0.9674(8) 0.1904(4) 0.054(2) Uani 1 1 d . . . . .
H15 H -0.0683 0.9731 0.2354 0.065 Uiso 1 1 calc R . . . .
C1 C -0.3930(7) 1.5729(7) 0.1077(4) 0.0484(19) Uani 1 1 d . . . . .
C26 C 0.1825(7) 1.5399(8) 0.2515(4) 0.056(2) Uani 1 1 d . . . . .
H26 H 0.2173 1.4918 0.2191 0.067 Uiso 1 1 calc R . . . .
C2 C -0.5295(7) 1.5595(8) 0.1185(3) 0.055(2) Uani 1 1 d . . . . .
H2A H -0.5780 1.5192 0.0798 0.066 Uiso 1 1 calc R . . . .
H2B H -0.5347 1.4946 0.1542 0.066 Uiso 1 1 calc R . . . .
C6 C -0.3731(7) 1.6879(8) 0.0597(4) 0.059(2) Uani 1 1 d . . . . .
H6A H -0.2830 1.7013 0.0594 0.071 Uiso 1 1 calc R . . . .
H6B H -0.4100 1.6583 0.0164 0.071 Uiso 1 1 calc R . . . .
C25 C 0.2597(7) 1.6191(9) 0.2957(4) 0.058(2) Uani 1 1 d . . . . .
H25 H 0.3456 1.6277 0.2929 0.069 Uiso 1 1 calc R . . . .
C4 C 0.4293(8) 1.8062(9) 0.0808(5) 0.079(3) Uani 1 1 d . . . . .
H4A H 0.3853 1.7740 0.0393 0.095 Uiso 1 1 calc R . . . .
H4B H 0.3927 1.8960 0.0912 0.095 Uiso 1 1 calc R . . . .
C18 C -0.0948(7) 0.9422(8) 0.0571(4) 0.060(2) Uani 1 1 d . . . . .
H18 H -0.1037 0.9328 0.0121 0.072 Uiso 1 1 calc R . . . .
C5 C -0.4313(8) 1.8261(8) 0.0758(4) 0.075(3) Uani 1 1 d . . . . .
H5A H -0.4216 1.8952 0.0423 0.090 Uiso 1 1 calc R . . . .
H5B H -0.3879 1.8618 0.1168 0.090 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br01 0.0796(7) 0.0628(6) 0.0786(7) -0.0063(5) 0.0086(5) 0.0227(5)
Br02 0.0568(6) 0.0755(6) 0.0544(5) -0.0002(4) 0.0002(4) -0.0137(5)
O11 0.041(3) 0.040(3) 0.064(3) -0.007(2) 0.009(2) -0.014(2)
C3 0.055(6) 0.065(6) 0.091(7) -0.006(5) 0.012(5) 0.005(5)
O12 0.043(3) 0.052(3) 0.053(3) -0.008(2) 0.008(2) -0.007(2)
O7 0.063(4) 0.050(3) 0.062(4) -0.005(3) 0.004(3) 0.000(3)
C17 0.051(5) 0.034(4) 0.065(6) 0.001(4) 0.010(4) 0.003(4)
O8 0.053(3) 0.049(3) 0.066(4) 0.000(3) -0.002(3) -0.009(3)
C24 0.059(5) 0.048(4) 0.037(4) 0.008(3) 0.009(4) 0.004(4)
N13 0.075(5) 0.042(4) 0.055(4) 0.000(3) 0.022(3) -0.005(3)
C21 0.051(5) 0.040(4) 0.040(4) 0.005(3) 0.001(4) 0.006(4)
C19 0.044(5) 0.043(4) 0.072(6) 0.005(4) -0.002(4) 0.003(4)
N20 0.052(4) 0.057(4) 0.055(4) -0.016(3) 0.013(3) -0.004(3)
C23 0.051(5) 0.060(5) 0.046(5) -0.002(4) 0.014(4) 0.008(4)
C10 0.053(5) 0.038(4) 0.053(5) -0.007(4) 0.012(4) -0.008(4)
C9 0.050(5) 0.036(4) 0.055(5) 0.010(4) 0.010(4) -0.001(4)
C14 0.040(4) 0.044(4) 0.054(5) -0.009(4) 0.008(4) -0.017(4)
C22 0.043(5) 0.055(5) 0.048(5) 0.000(4) 0.008(4) 0.008(4)
C16 0.067(6) 0.055(5) 0.048(5) 0.011(4) 0.002(4) -0.005(4)
C15 0.061(5) 0.045(4) 0.059(5) 0.011(4) 0.011(4) 0.005(4)
C1 0.054(5) 0.038(4) 0.052(5) -0.005(4) 0.003(4) 0.008(4)
C26 0.036(5) 0.073(5) 0.058(5) -0.012(4) 0.007(4) 0.010(4)
C2 0.052(5) 0.055(5) 0.055(5) 0.000(4) -0.003(4) 0.000(4)
C6 0.055(5) 0.063(5) 0.056(5) 0.000(4) 0.001(4) -0.016(4)
C25 0.030(4) 0.083(6) 0.057(5) -0.008(5) -0.006(4) 0.005(4)
C4 0.048(5) 0.061(6) 0.118(8) -0.010(5) -0.024(5) 0.024(5)
C18 0.065(6) 0.055(5) 0.058(5) -0.013(4) 0.005(4) -0.008(5)
C5 0.072(7) 0.056(5) 0.094(7) 0.013(5) 0.001(5) 0.004(5)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br01 C17 1.909(7) . ?
Br02 C24 1.916(7) . ?
O11 O12 1.474(6) . ?
O11 C10 1.447(8) . ?
C3 C2 1.495(9) 1_655 ?
C3 C4 1.520(11) . ?
O12 C1 1.422(8) . ?
O7 O8 1.454(6) . ?
O7 C1 1.439(8) . ?
C17 C16 1.368(9) . ?
C17 C18 1.379(10) . ?
O8 C9 1.454(8) . ?
C24 C23 1.352(9) . ?
C24 C25 1.374(9) . ?
N13 C9 1.393(8) . ?
N13 C14 1.395(8) . ?
C21 N20 1.391(8) . ?
C21 C22 1.372(9) . ?
C21 C26 1.379(9) . ?
C19 C14 1.371(9) . ?
C19 C18 1.414(9) . ?
N20 C10 1.424(8) . ?
C23 C22 1.387(9) . ?
C10 C9 1.525(9) . ?
C14 C15 1.380(9) . ?
C16 C15 1.361(9) . ?
C1 C2 1.508(9) . ?
C1 C6 1.509(9) . ?
C26 C25 1.367(10) . ?
C2 C3 1.495(9) 1_455 ?
C6 C5 1.502(10) . ?
C4 C5 1.517(10) 1_655 ?
C5 C4 1.517(10) 1_455 ?

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
C10 O11 O12 105.4(4) . . ?
C2 C3 C4 110.4(7) 1_655 . ?
C1 O12 O11 109.1(4) . . ?
C1 O7 O8 109.5(5) . . ?
C16 C17 Br01 120.9(6) . . ?
C16 C17 C18 121.1(7) . . ?
C18 C17 Br01 118.0(6) . . ?
C9 O8 O7 105.6(4) . . ?
C23 C24 Br02 120.6(6) . . ?
C23 C24 C25 121.3(7) . . ?
C25 C24 Br02 118.1(6) . . ?
C9 N13 C14 123.6(6) . . ?
C22 C21 N20 121.8(7) . . ?
C22 C21 C26 119.5(7) . . ?
C26 C21 N20 118.7(6) . . ?
C14 C19 C18 121.4(7) . . ?
C21 N20 C10 124.5(6) . . ?
C24 C23 C22 120.5(7) . . ?
O11 C10 C9 112.1(6) . . ?
N20 C10 O11 104.1(5) . . ?
N20 C10 C9 107.6(6) . . ?
O8 C9 C10 110.7(6) . . ?
N13 C9 O8 106.7(5) . . ?
N13 C9 C10 110.6(6) . . ?
C19 C14 N13 121.7(7) . . ?
C19 C14 C15 117.9(7) . . ?
C15 C14 N13 120.4(7) . . ?
C21 C22 C23 119.0(7) . . ?
C15 C16 C17 119.7(7) . . ?
C16 C15 C14 122.1(7) . . ?
O12 C1 O7 109.8(6) . . ?
O12 C1 C2 103.8(6) . . ?
O12 C1 C6 114.2(6) . . ?
O7 C1 C2 113.3(6) . . ?
O7 C1 C6 103.4(6) . . ?
C2 C1 C6 112.7(6) . . ?
C25 C26 C21 121.5(7) . . ?
C3 C2 C1 112.9(6) 1_455 . ?
C5 C6 C1 112.1(6) . . ?
C26 C25 C24 118.2(7) . . ?
C5 C4 C3 110.1(6) 1_655 . ?
C17 C18 C19 117.7(7) . . ?
C6 C5 C4 110.3(7) . 1_455 ?


####################################################################### 
# 
# 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_kls-94-9
_database_code_depnum_ccdc_archive 'CCDC 1905330'
loop_
_audit_author_name
_audit_author_address
'Ekaterina Mescheryakova'
;Institute of Petrochemistry and Catalysis
Russia
;
_audit_update_record             
;
2019-03-25 deposited with the CCDC.	2019-09-23 downloaded from the CCDC.
;
_audit_creation_date             2018-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2013-4
_chemical_name_systematic        
9-N,10-N-bis(4-fluorophenyl)-7,8,11,12-tetraoxaspiro[5.6]dodecane-9,10-diamine
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H22 F2 N2 O4'
_chemical_formula_sum            'C20 H22 F2 N2 O4'
_chemical_formula_weight         392.40
_exptl_crystal_recrystallization_method hexane/Et2O
_chemical_melting_point          ?
_exptl_crystal_description       prizm
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      293(2)
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_chemical_absolute_configuration ?
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                   12.9687(13)
_cell_length_b                   10.0294(8)
_cell_length_c                   14.5182(15)
_cell_angle_alpha                90
_cell_angle_beta                 100.068(10)
_cell_angle_gamma                90
_cell_volume                     1859.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2159
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6790
_cell_measurement_theta_min      1.9950
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33232
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             824.0
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0927
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9607
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.116
_diffrn_reflns_theta_min         2.317
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1709
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   51.00   1.0000   47.8550
omega____ theta____ kappa____ phi______ frames
    -      -16.2449   77.0000  120.0000 67

#__ type_ start__ end____ width___ exp.time_
  2 omega  -58.00   42.00   1.0000   47.8550
omega____ theta____ kappa____ phi______ frames
    -      -16.2449    0.0000  -60.0000 100

#__ type_ start__ end____ width___ exp.time_
  3 omega   23.00   56.00   1.0000   47.8550
omega____ theta____ kappa____ phi______ frames
    -       16.9480  -99.0000  -90.0000 33

#__ type_ start__ end____ width___ exp.time_
  4 omega  -23.00   22.00   1.0000   47.8550
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000  120.0000 45
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0424594000
_diffrn_orient_matrix_UB_12      0.0077488000
_diffrn_orient_matrix_UB_13      0.0244424000
_diffrn_orient_matrix_UB_21      0.0356652000
_diffrn_orient_matrix_UB_22      0.0009987000
_diffrn_orient_matrix_UB_23      0.0430777000
_diffrn_orient_matrix_UB_31      0.0042243000
_diffrn_orient_matrix_UB_32      0.0701980000
_diffrn_orient_matrix_UB_33      -0.0032412000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_type              'XCalibur E'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2237
_reflns_number_total             4313
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4313
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1517
_refine_ls_R_factor_gt           0.0825
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0957P)²+0.6670P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2015
_refine_ls_wR_factor_ref         0.2375
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 N20(H20), N13(H13), C26(H26), C22(H22), C15(H15), C25(H25), C18(H18),
 C23(H23), C16(H16), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O12 O 0.81275(16) 0.6200(2) 0.15769(14) 0.0385(6) Uani 1 1 d . . . . .
O11 O 0.70417(15) 0.5993(2) 0.11174(15) 0.0396(6) Uani 1 1 d . . . . .
O7 O 0.85300(19) 0.4720(2) 0.04484(17) 0.0483(6) Uani 1 1 d . . . . .
O8 O 0.83423(17) 0.3693(2) 0.11168(18) 0.0491(6) Uani 1 1 d . . . . .
N20 N 0.5637(2) 0.4682(3) 0.1213(2) 0.0471(8) Uani 1 1 d . . . . .
H20 H 0.5369 0.4185 0.0750 0.057 Uiso 1 1 calc R . . . .
C1 C 0.8811(2) 0.5937(3) 0.0931(2) 0.0364(7) Uani 1 1 d . . . . .
N13 N 0.7002(3) 0.2334(3) 0.1355(2) 0.0531(8) Uani 1 1 d . . . . .
H13 H 0.7015 0.2266 0.1948 0.064 Uiso 1 1 calc R . . . .
C6 C 0.9893(3) 0.5924(4) 0.1519(3) 0.0468(9) Uani 1 1 d . . . . .
H6A H 1.0384 0.5569 0.1149 0.056 Uiso 1 1 calc R . . . .
H6B H 0.9894 0.5334 0.2049 0.056 Uiso 1 1 calc R . . . .
C26 C 0.3884(3) 0.5173(3) 0.1438(2) 0.0446(8) Uani 1 1 d . . . . .
H26 H 0.3639 0.4534 0.0988 0.054 Uiso 1 1 calc R . . . .
C21 C 0.4950(2) 0.5407(3) 0.1672(2) 0.0360(7) Uani 1 1 d . . . . .
C10 C 0.6734(2) 0.4718(3) 0.1461(2) 0.0374(7) Uani 1 1 d . . . . .
H10 H 0.6943 0.4670 0.2142 0.045 Uiso 1 1 calc R . . . .
F2 F 0.28809(18) 0.7515(3) 0.2940(2) 0.0913(10) Uani 1 1 d . . . . .
F1 F 0.5928(2) -0.2148(2) -0.0776(2) 0.0911(9) Uani 1 1 d . . . . .
C14 C 0.6769(3) 0.1183(3) 0.0796(3) 0.0475(9) Uani 1 1 d . . . . .
C24 C 0.3568(3) 0.6789(4) 0.2529(3) 0.0534(10) Uani 1 1 d . . . . .
C17 C 0.6232(3) -0.1030(4) -0.0255(3) 0.0546(10) Uani 1 1 d . . . . .
C22 C 0.5307(3) 0.6334(3) 0.2358(2) 0.0450(8) Uani 1 1 d . . . . .
H22 H 0.6023 0.6487 0.2528 0.054 Uiso 1 1 calc R . . . .
C9 C 0.7211(3) 0.3561(3) 0.0997(3) 0.0438(8) Uani 1 1 d . . . . .
H9 H 0.6924 0.3571 0.0326 0.053 Uiso 1 1 calc R . . . .
C15 C 0.6325(3) 0.0113(4) 0.1155(3) 0.0527(9) Uani 1 1 d . . . . .
H15 H 0.6203 0.0142 0.1767 0.063 Uiso 1 1 calc R . . . .
C25 C 0.3187(3) 0.5865(4) 0.1859(3) 0.0524(10) Uani 1 1 d . . . . .
H25 H 0.2471 0.5714 0.1695 0.063 Uiso 1 1 calc R . . . .
C2 C 0.8721(3) 0.6961(4) 0.0144(3) 0.0532(10) Uani 1 1 d . . . . .
H2A H 0.9135 0.6669 -0.0314 0.064 Uiso 1 1 calc R . . . .
H2B H 0.7996 0.7021 -0.0167 0.064 Uiso 1 1 calc R . . . .
C18 C 0.6686(4) -0.0038(4) -0.0652(3) 0.0628(11) Uani 1 1 d . . . . .
H18 H 0.6806 -0.0109 -0.1263 0.075 Uiso 1 1 calc R . . . .
C23 C 0.4616(3) 0.7033(4) 0.2791(3) 0.0502(9) Uani 1 1 d . . . . .
H23 H 0.4855 0.7658 0.3252 0.060 Uiso 1 1 calc R . . . .
C3 C 0.9093(3) 0.8323(4) 0.0510(3) 0.0608(11) Uani 1 1 d . . . . .
H3A H 0.9080 0.8931 -0.0012 0.073 Uiso 1 1 calc R . . . .
H3B H 0.8623 0.8667 0.0904 0.073 Uiso 1 1 calc R . . . .
C5 C 1.0259(3) 0.7301(4) 0.1877(3) 0.0572(10) Uani 1 1 d . . . . .
H5A H 0.9825 0.7619 0.2311 0.069 Uiso 1 1 calc R . . . .
H5B H 1.0977 0.7252 0.2206 0.069 Uiso 1 1 calc R . . . .
C16 C 0.6058(3) -0.0989(4) 0.0629(3) 0.0562(10) Uani 1 1 d . . . . .
H16 H 0.5756 -0.1715 0.0880 0.067 Uiso 1 1 calc R . . . .
C4 C 1.0191(3) 0.8253(4) 0.1066(3) 0.0662(12) Uani 1 1 d . . . . .
H4A H 1.0668 0.7967 0.0660 0.079 Uiso 1 1 calc R . . . .
H4B H 1.0405 0.9135 0.1299 0.079 Uiso 1 1 calc R . . . .
C19 C 0.6979(3) 0.1119(4) -0.0119(3) 0.0586(10) Uani 1 1 d . . . . .
H19 H 0.7305 0.1825 -0.0368 0.070 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O12 0.0322(12) 0.0410(13) 0.0424(13) -0.0080(10) 0.0069(9) -0.0064(10)
O11 0.0280(12) 0.0364(13) 0.0530(14) 0.0010(10) 0.0028(9) 0.0017(9)
O7 0.0509(15) 0.0432(14) 0.0543(15) -0.0134(11) 0.0190(11) -0.0073(11)
O8 0.0369(13) 0.0352(13) 0.0755(18) -0.0013(12) 0.0106(11) 0.0023(10)
N20 0.0285(14) 0.0514(18) 0.0603(19) -0.0208(14) 0.0046(12) -0.0035(13)
C1 0.0308(16) 0.0370(18) 0.0427(18) -0.0066(14) 0.0098(13) -0.0005(14)
N13 0.069(2) 0.0430(18) 0.0476(18) -0.0021(14) 0.0108(15) -0.0053(15)
C6 0.0337(18) 0.051(2) 0.056(2) -0.0008(16) 0.0074(15) 0.0022(16)
C26 0.0351(18) 0.043(2) 0.052(2) -0.0111(15) -0.0009(14) -0.0004(15)
C21 0.0306(16) 0.0337(17) 0.0438(18) -0.0027(13) 0.0069(13) -0.0018(13)
C10 0.0319(17) 0.0353(18) 0.0452(18) -0.0012(14) 0.0072(13) -0.0015(13)
F2 0.0452(14) 0.127(2) 0.101(2) -0.0590(18) 0.0107(13) 0.0181(14)
F1 0.106(2) 0.0471(14) 0.110(2) -0.0342(14) -0.0099(17) -0.0032(14)
C14 0.0378(19) 0.042(2) 0.061(2) -0.0163(17) 0.0064(16) 0.0049(16)
C24 0.037(2) 0.068(3) 0.056(2) -0.0169(18) 0.0099(16) 0.0055(18)
C17 0.055(2) 0.032(2) 0.071(3) -0.0169(18) -0.0035(18) 0.0031(17)
C22 0.0328(17) 0.049(2) 0.054(2) -0.0115(16) 0.0074(14) -0.0101(15)
C9 0.0383(19) 0.0309(19) 0.062(2) -0.0003(15) 0.0097(15) 0.0012(14)
C15 0.051(2) 0.054(2) 0.051(2) 0.0006(17) 0.0034(17) 0.0024(18)
C25 0.0287(17) 0.063(2) 0.062(2) -0.0143(19) -0.0001(15) 0.0015(17)
C2 0.056(2) 0.058(2) 0.048(2) 0.0030(17) 0.0146(17) -0.0033(19)
C18 0.081(3) 0.054(3) 0.056(2) -0.0079(19) 0.018(2) 0.013(2)
C23 0.041(2) 0.057(2) 0.053(2) -0.0217(17) 0.0088(15) -0.0078(17)
C3 0.060(3) 0.048(2) 0.076(3) 0.015(2) 0.017(2) -0.0052(19)
C5 0.0322(19) 0.064(3) 0.074(3) -0.015(2) 0.0045(17) -0.0088(17)
C16 0.053(2) 0.038(2) 0.072(3) 0.0022(18) -0.0043(18) 0.0022(17)
C4 0.056(3) 0.053(2) 0.094(3) -0.013(2) 0.027(2) -0.021(2)
C19 0.067(3) 0.041(2) 0.073(3) -0.0037(19) 0.027(2) 0.0004(19)

_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
O12 O11 1.464(3) . ?
O12 C1 1.423(3) . ?
O11 C10 1.453(4) . ?
O7 O8 1.464(3) . ?
O7 C1 1.424(4) . ?
O8 C9 1.453(4) . ?
N20 C21 1.405(4) . ?
N20 C10 1.405(4) . ?
C1 C6 1.509(4) . ?
C1 C2 1.526(5) . ?
N13 C14 1.413(4) . ?
N13 C9 1.381(4) . ?
C6 C5 1.522(5) . ?
C26 C21 1.386(4) . ?
C26 C25 1.366(5) . ?
C21 C22 1.382(4) . ?
C10 C9 1.527(4) . ?
F2 C24 1.367(4) . ?
F1 C17 1.371(4) . ?
C14 C15 1.364(5) . ?
C14 C19 1.402(5) . ?
C24 C25 1.371(5) . ?
C24 C23 1.367(5) . ?
C17 C18 1.337(6) . ?
C17 C16 1.342(5) . ?
C22 C23 1.374(5) . ?
C15 C16 1.354(5) . ?
C2 C3 1.514(5) . ?
C18 C19 1.409(5) . ?
C3 C4 1.510(6) . ?
C5 C4 1.507(6) . ?

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 O12 O11 109.5(2) . . ?
C10 O11 O12 105.6(2) . . ?
C1 O7 O8 109.6(2) . . ?
C9 O8 O7 105.4(2) . . ?
C10 N20 C21 124.2(3) . . ?
O12 C1 O7 110.4(2) . . ?
O12 C1 C6 104.7(3) . . ?
O12 C1 C2 113.2(3) . . ?
O7 C1 C6 113.8(3) . . ?
O7 C1 C2 103.2(3) . . ?
C6 C1 C2 111.8(3) . . ?
C9 N13 C14 123.2(3) . . ?
C1 C6 C5 112.9(3) . . ?
C25 C26 C21 120.9(3) . . ?
C26 C21 N20 119.0(3) . . ?
C22 C21 N20 122.0(3) . . ?
C22 C21 C26 119.0(3) . . ?
O11 C10 C9 111.2(3) . . ?
N20 C10 O11 105.1(3) . . ?
N20 C10 C9 109.7(3) . . ?
C15 C14 N13 119.0(3) . . ?
C15 C14 C19 119.4(3) . . ?
C19 C14 N13 121.6(3) . . ?
F2 C24 C25 119.2(3) . . ?
C23 C24 F2 118.3(3) . . ?
C23 C24 C25 122.4(3) . . ?
C18 C17 F1 118.4(4) . . ?
C18 C17 C16 123.3(3) . . ?
C16 C17 F1 118.2(4) . . ?
C23 C22 C21 120.7(3) . . ?
O8 C9 C10 110.9(3) . . ?
N13 C9 O8 107.2(3) . . ?
N13 C9 C10 113.0(3) . . ?
C16 C15 C14 120.7(4) . . ?
C26 C25 C24 118.4(3) . . ?
C3 C2 C1 111.5(3) . . ?
C17 C18 C19 118.2(4) . . ?
C24 C23 C22 118.5(3) . . ?
C4 C3 C2 111.1(3) . . ?
C4 C5 C6 109.7(3) . . ?
C17 C16 C15 119.7(4) . . ?
C5 C4 C3 111.6(3) . . ?
C14 C19 C18 118.7(4) . . ?


