# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

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

data_rr-250-9
_audit_block_doi                 10.5517/ccdc.csd.cc14mwn9
_database_code_depnum_ccdc_archive 'CCDC 1061801'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tet.2016.04.055 2016
_audit_update_record             
;
2015-04-27 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;
_audit_creation_date             2015-04-27
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_systematic        
11-(4-fluorophenyl)-8,9,13,14-tetraoxa-11-azaspiro[6.7]tetradecane
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H20 F N O4'
_chemical_formula_sum            'C15 H20 F N O4'
_chemical_formula_weight         297.32
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   'C c'
_symmetry_int_tables_number      9
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_exptl_crystal_description       plank
_exptl_crystal_colour            colorless
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 'x, -y, z+1/2'
3 'x+1/2, y+1/2, z'
4 'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   5.7993(5)
_cell_length_b                   25.037(3)
_cell_length_c                   10.1500(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.329(11)
_cell_angle_gamma                90.00
_cell_volume                     1449.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    421
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.6355
_cell_measurement_theta_min      1.6193
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5439
_diffrn_reflns_theta_full        30.93
_diffrn_reflns_theta_max         30.93
_diffrn_reflns_theta_min         2.61
_diffrn_detector_area_resol_mean 16.1709
_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    5.00   54.00   1.0000   23.2100
omega____ theta____ kappa____ phi______ frames
    -       24.2348   57.0000  150.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega  -46.00   54.00   1.0000   23.2100
omega____ theta____ kappa____ phi______ frames
    -       24.2348  -77.0000 -180.0000 100

#__ type_ start__ end____ width___ exp.time_
  3 omega  -38.00   -2.00   1.0000   23.2100
omega____ theta____ kappa____ phi______ frames
    -       24.2348  -77.0000  -90.0000 36

#__ type_ start__ end____ width___ exp.time_
  4 omega   -7.00   18.00   1.0000   23.2100
omega____ theta____ kappa____ phi______ frames
    -       24.2348   81.0000  146.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega   -3.00   86.00   1.0000   23.2100
omega____ theta____ kappa____ phi______ frames
    -       24.2348   77.0000  -60.0000 89

#__ type_ start__ end____ width___ exp.time_
  6 omega    1.00   94.00   1.0000   23.2100
omega____ theta____ kappa____ phi______ frames
    -       24.2348   77.0000   30.0000 93
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1263206000
_diffrn_orient_matrix_UB_12      -0.0188940000
_diffrn_orient_matrix_UB_13      -0.0048961000
_diffrn_orient_matrix_UB_21      0.0201063000
_diffrn_orient_matrix_UB_22      0.0377733000
_diffrn_orient_matrix_UB_23      -0.0476149000
_diffrn_orient_matrix_UB_31      0.0009092000
_diffrn_orient_matrix_UB_32      0.0570567000
_diffrn_orient_matrix_UB_33      0.0300526000
_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 Eos'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2247
_reflns_number_total             2662
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.7(8)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         2662
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0677P)²+0.0653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0971
_refine_ls_wR_factor_ref         0.1053
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O -0.3245(3) -0.31307(5) -0.26347(15) 0.0414(3) Uani 1 d . . .
O2 O 0.0061(3) -0.34868(6) -0.33376(17) 0.0491(4) Uani 1 d . . .
O3 O 0.0095(3) -0.30114(6) -0.41915(17) 0.0529(4) Uani 1 d . . .
O4 O -0.2096(4) -0.30124(7) -0.12765(15) 0.0556(4) Uani 1 d . . .
F5 F -0.5574(4) -0.06122(7) -0.3667(2) 0.0853(6) Uani 1 d . . .
N6 N 0.0128(3) -0.23772(6) -0.24025(18) 0.0426(4) Uani 1 d . . .
C7 C -0.2297(4) -0.35892(7) -0.3175(2) 0.0387(4) Uani 1 d . . .
C8 C -0.1385(3) -0.19407(7) -0.27696(19) 0.0357(4) Uani 1 d . . .
C9 C -0.4206(4) -0.10523(9) -0.3369(3) 0.0539(5) Uani 1 d . . .
C1 C -0.2028(4) -0.40631(9) -0.2227(2) 0.0496(5) Uani 1 d . . .
C2 C -0.0954(4) -0.15707(8) -0.3723(2) 0.0431(4) Uani 1 d . . .
C3 C -0.2376(5) -0.11284(9) -0.4032(2) 0.0507(5) Uani 1 d . . .
C4 C -0.4680(4) -0.14028(10) -0.2421(3) 0.0523(5) Uani 1 d . . .
C5 C -0.5293(6) -0.47394(10) -0.3041(3) 0.0620(7) Uani 1 d . . .
C6 C -0.3289(4) -0.18514(8) -0.2130(2) 0.0441(4) Uani 1 d . . .
C10 C -0.4288(5) -0.42256(9) -0.5056(2) 0.0529(5) Uani 1 d . . .
C11 C -0.3967(5) -0.36580(8) -0.4508(2) 0.0471(5) Uani 1 d . . .
C12 C 0.1367(4) -0.26168(9) -0.3357(3) 0.0547(6) Uani 1 d . . .
C13 C -0.4355(5) -0.43078(9) -0.2024(2) 0.0548(6) Uani 1 d . . .
C14 C -0.6079(6) -0.45454(10) -0.4470(3) 0.0612(6) Uani 1 d . . .
C15 C -0.0010(5) -0.26772(9) -0.1242(2) 0.0524(5) Uani 1 d . . .
H10A H -0.287(6) -0.4421(11) -0.497(3) 0.058(8) Uiso 1 d . . .
H1A H -0.130(7) -0.4300(14) -0.255(4) 0.073(10) Uiso 1 d . . .
H10B H -0.478(6) -0.4216(11) -0.601(3) 0.059(8) Uiso 1 d . . .
H5A H -0.403(5) -0.5009(11) -0.303(2) 0.050(7) Uiso 1 d . . .
H3 H -0.215(7) -0.0845(14) -0.465(3) 0.078(10) Uiso 1 d . . .
H4 H -0.580(6) -0.1318(13) -0.199(3) 0.066(9) Uiso 1 d . . .
H14A H -0.728(8) -0.4329(14) -0.445(4) 0.081(11) Uiso 1 d . . .
H1B H -0.112(7) -0.3918(13) -0.131(4) 0.079(10) Uiso 1 d . . .
H13A H -0.555(6) -0.4007(12) -0.212(3) 0.062(8) Uiso 1 d . . .
H14B H -0.654(9) -0.4853(17) -0.507(4) 0.109(14) Uiso 1 d . . .
H15A H 0.129(5) -0.2931(11) -0.114(3) 0.051(7) Uiso 1 d . . .
H2 H 0.034(5) -0.1639(10) -0.420(3) 0.048(6) Uiso 1 d . . .
H5B H -0.681(6) -0.4929(12) -0.285(3) 0.066(8) Uiso 1 d . . .
H13B H -0.410(6) -0.4480(14) -0.102(3) 0.073(9) Uiso 1 d . . .
H6 H -0.364(5) -0.2081(10) -0.142(3) 0.050(7) Uiso 1 d . . .
H12A H 0.159(7) -0.2345(12) -0.401(3) 0.070(9) Uiso 1 d . . .
H11A H -0.530(7) -0.3514(11) -0.442(3) 0.061(8) Uiso 1 d . . .
H11B H -0.331(6) -0.3415(11) -0.515(3) 0.063(8) Uiso 1 d . . .
H15B H -0.007(7) -0.2430(14) -0.053(4) 0.077(10) Uiso 1 d . . .
H12B H 0.275(10) -0.2778(17) -0.278(5) 0.116(15) Uiso 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 O4 1.450(2) . ?
O1 C7 1.424(2) . ?
O2 O3 1.474(2) . ?
O2 C7 1.430(3) . ?
O3 C12 1.419(3) . ?
O4 C15 1.467(3) . ?
F5 C9 1.360(3) . ?
N6 C8 1.409(3) . ?
N6 C12 1.437(3) . ?
N6 C15 1.411(3) . ?
C7 C1 1.518(3) . ?
C7 C11 1.526(3) . ?
C8 C2 1.394(3) . ?
C8 C6 1.396(3) . ?
C9 C3 1.368(4) . ?
C9 C4 1.366(4) . ?
C1 C13 1.529(4) . ?
C2 C3 1.383(3) . ?
C4 C6 1.384(3) . ?
C5 C13 1.525(4) . ?
C5 C14 1.520(4) . ?
C10 C11 1.525(3) . ?
C10 C14 1.515(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 O4 112.79(15) . . ?
C7 O2 O3 109.08(14) . . ?
C12 O3 O2 105.75(18) . . ?
O1 O4 C15 112.07(14) . . ?
C8 N6 C12 120.56(19) . . ?
C8 N6 C15 120.52(19) . . ?
C15 N6 C12 116.77(19) . . ?
O1 C7 O2 110.06(15) . . ?
O1 C7 C1 112.90(17) . . ?
O1 C7 C11 101.83(16) . . ?
O2 C7 C1 102.81(17) . . ?
O2 C7 C11 112.67(18) . . ?
C1 C7 C11 116.79(17) . . ?
C2 C8 N6 121.23(18) . . ?
C2 C8 C6 118.14(19) . . ?
C6 C8 N6 120.53(17) . . ?
F5 C9 C3 118.5(2) . . ?
F5 C9 C4 119.6(2) . . ?
C4 C9 C3 121.9(2) . . ?
C7 C1 C13 113.91(19) . . ?
C3 C2 C8 121.1(2) . . ?
C9 C3 C2 118.9(2) . . ?
C9 C4 C6 119.3(2) . . ?
C14 C5 C13 115.4(2) . . ?
C4 C6 C8 120.7(2) . . ?
C14 C10 C11 113.4(2) . . ?
C10 C11 C7 116.43(19) . . ?
O3 C12 N6 115.07(18) . . ?
C5 C13 C1 114.1(2) . . ?
C10 C14 C5 115.7(3) . . ?
N6 C15 O4 117.0(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_hgm-478-5
_audit_block_doi                 10.5517/ccdc.csd.cc1q78lt
_database_code_depnum_ccdc_archive 'CCDC 1585916'
_audit_update_record             
;
2017-11-16 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;
_audit_creation_date             2017-11-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_systematic        
10-(4-fluorophenyl)-7,8,12,13-tetraoxa-10-azaspiro[5.7]tridecane
_chemical_name_common            ?
_chemical_formula_moiety         'C14 H18 F N O4'
_chemical_formula_sum            'C14 H18 F N O4'
_chemical_formula_weight         283.29
_exptl_crystal_recrystallization_method CDCL3
_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      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 ad
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                   12.4485(6)
_cell_length_b                   10.2927(6)
_cell_length_c                   21.8055(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2793.9(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2264
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.8450
_cell_measurement_theta_min      2.4660
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86958
_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    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1200.0
_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  0.0522
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14961
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.029
_diffrn_reflns_theta_min         3.176
_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  -43.00   51.00   1.0000   17.8800
omega____ theta____ kappa____ phi______ frames
    -      -16.2449   77.0000  150.0000 94

#__ type_ start__ end____ width___ exp.time_
  2 omega  -43.00   51.00   1.0000   17.8800
omega____ theta____ kappa____ phi______ frames
    -      -16.2449   77.0000  -90.0000 94

#__ type_ start__ end____ width___ exp.time_
  3 omega   -6.00   85.00   1.0000   17.8800
omega____ theta____ kappa____ phi______ frames
    -       16.9480   77.0000    0.0000 91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0500329000
_diffrn_orient_matrix_UB_12      -0.0162976000
_diffrn_orient_matrix_UB_13      0.0135002000
_diffrn_orient_matrix_UB_21      0.0263321000
_diffrn_orient_matrix_UB_22      0.0136817000
_diffrn_orient_matrix_UB_23      -0.0281145000
_diffrn_orient_matrix_UB_31      0.0069902000
_diffrn_orient_matrix_UB_32      0.0655844000
_diffrn_orient_matrix_UB_33      0.0091990000
_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 Gemini Eos'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1339
_reflns_number_total             3246
_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         0.580
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2066
_refine_ls_R_factor_gt           0.0939
_refine_ls_restrained_S_all      1.175
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002
_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          0.2198
_refine_ls_wR_factor_ref         0.2702
_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 Secondary CH2 refined with riding coordinates:
 C009(H00A,H00B), C013(H01A,H01B), C014(H01C,H01D), C016(H01E,H01F), C017(H01G,
 H01H), C019(H01I,H01J), C020(H02A,H02B)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C010(H010), C015(H015), C018(H018)
;
_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
O4 O 0.4461(2) 0.1790(3) 0.20932(10) 0.0712(8) Uani 1 1 d . . . . .
N1 N 0.3164(2) 0.1704(3) 0.29116(13) 0.0658(8) Uani 1 1 d . . . . .
O3 O 0.3687(2) 0.1621(2) 0.15920(10) 0.0732(8) Uani 1 1 d . . . . .
C004 C 0.3352(3) 0.2771(3) 0.33008(14) 0.0557(8) Uani 1 1 d . . . . .
C005 C 0.3131(3) 0.2818(4) 0.14852(16) 0.0697(10) Uani 1 1 d . . . . .
O2 O 0.2568(4) 0.3232(4) 0.20339(13) 0.1135(12) Uani 1 1 d . . . . .
C007 C 0.4351(3) 0.3225(5) 0.34190(18) 0.0842(12) Uani 1 1 d . . . . .
H007 H 0.4937 0.2854 0.3221 0.101 Uiso 1 1 calc R . . . .
O1 O 0.1785(2) 0.2345(5) 0.22133(15) 0.1298(16) Uani 1 1 d . . . . .
C009 C 0.2126(4) 0.1488(5) 0.2663(2) 0.0885(13) Uani 1 1 d . . . . .
H00A H 0.1611 0.1514 0.2996 0.106 Uiso 1 1 calc R . . . .
H00B H 0.2109 0.0618 0.2493 0.106 Uiso 1 1 calc R . . . .
C010 C 0.2517(3) 0.3411(5) 0.35750(17) 0.0806(11) Uani 1 1 d . . . . .
H010 H 0.1817 0.3157 0.3487 0.097 Uiso 1 1 calc R . . . .
C011 C 0.3676(5) 0.4792(4) 0.41028(19) 0.0864(13) Uani 1 1 d . . . . .
F1 F 0.3865(3) 0.5775(3) 0.45139(13) 0.1346(12) Uani 1 1 d . . . . .
C013 C 0.4054(3) 0.1088(4) 0.25919(17) 0.0778(11) Uani 1 1 d . . . . .
H01A H 0.4632 0.0945 0.2883 0.093 Uiso 1 1 calc R . . . .
H01B H 0.3819 0.0243 0.2446 0.093 Uiso 1 1 calc R . . . .
C014 C 0.3848(6) 0.3944(5) 0.1405(2) 0.116(2) Uani 1 1 d . . . . .
H01C H 0.4303 0.4030 0.1764 0.139 Uiso 1 1 calc R . . . .
H01D H 0.3419 0.4728 0.1371 0.139 Uiso 1 1 calc R . . . .
C015 C 0.4516(4) 0.4237(5) 0.3831(2) 0.0923(13) Uani 1 1 d . . . . .
H015 H 0.5209 0.4524 0.3917 0.111 Uiso 1 1 calc R . . . .
C016 C 0.3089(6) 0.2442(6) 0.0402(3) 0.129(2) Uani 1 1 d . . . . .
H01E H 0.2613 0.2371 0.0052 0.155 Uiso 1 1 calc R . . . .
H01F H 0.3488 0.1635 0.0435 0.155 Uiso 1 1 calc R . . . .
C017 C 0.2467(5) 0.2612(5) 0.0937(2) 0.1036(15) Uani 1 1 d . . . . .
H01G H 0.2020 0.1851 0.0998 0.124 Uiso 1 1 calc R . . . .
H01H H 0.1996 0.3354 0.0882 0.124 Uiso 1 1 calc R . . . .
C018 C 0.2684(4) 0.4410(5) 0.39724(19) 0.0942(13) Uani 1 1 d . . . . .
H018 H 0.2102 0.4826 0.4153 0.113 Uiso 1 1 calc R . . . .
C019 C 0.3865(6) 0.3539(12) 0.0294(3) 0.175(4) Uani 1 1 d . . . . .
H01I H 0.3469 0.4315 0.0183 0.210 Uiso 1 1 calc R . . . .
H01J H 0.4335 0.3318 -0.0045 0.210 Uiso 1 1 calc R . . . .
C020 C 0.4531(5) 0.3813(8) 0.0853(3) 0.161(3) Uani 1 1 d . . . . .
H02A H 0.5041 0.3112 0.0913 0.193 Uiso 1 1 calc R . . . .
H02B H 0.4934 0.4610 0.0791 0.193 Uiso 1 1 calc R . . . .


_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
O4 O3 1.467(3) . ?
O4 C013 1.401(5) . ?
N1 C004 1.408(5) . ?
N1 C009 1.419(5) . ?
N1 C013 1.455(5) . ?
O3 C005 1.432(4) . ?
C004 C007 1.352(5) . ?
C004 C010 1.368(5) . ?
C005 O2 1.451(5) . ?
C005 C014 1.474(7) . ?
C005 C017 1.469(6) . ?
O2 O1 1.392(5) . ?
C007 C015 1.392(6) . ?
O1 C009 1.385(6) . ?
C010 C018 1.360(6) . ?
C011 F1 1.372(5) . ?
C011 C015 1.331(6) . ?
C011 C018 1.326(7) . ?
C014 C020 1.481(9) . ?
C016 C017 1.412(8) . ?
C016 C019 1.504(10) . ?
C019 C020 1.500(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C013 O4 O3 106.2(3) . . ?
C004 N1 C013 120.1(3) . . ?
C009 N1 C004 120.3(3) . . ?
C009 N1 C013 116.2(3) . . ?
C005 O3 O4 109.7(2) . . ?
C007 C004 N1 122.5(3) . . ?
C007 C004 C010 116.6(4) . . ?
C010 C004 N1 120.8(3) . . ?
O3 C005 O2 110.6(3) . . ?
O3 C005 C014 113.8(4) . . ?
O3 C005 C017 106.3(3) . . ?
O2 C005 C014 99.2(4) . . ?
O2 C005 C017 116.2(4) . . ?
C014 C005 C017 111.0(3) . . ?
O1 O2 C005 112.2(4) . . ?
C004 C007 C015 121.2(4) . . ?
O2 O1 C009 113.7(3) . . ?
N1 C009 O1 116.8(4) . . ?
C004 C010 C018 121.7(4) . . ?
C015 C011 F1 118.1(5) . . ?
C018 C011 F1 121.2(5) . . ?
C018 C011 C015 120.6(4) . . ?
O4 C013 N1 115.0(3) . . ?
C005 C014 C020 111.9(4) . . ?
C011 C015 C007 119.4(4) . . ?
C017 C016 C019 112.9(5) . . ?
C016 C017 C005 112.4(5) . . ?
C011 C018 C010 120.2(4) . . ?
C016 C019 C020 111.7(5) . . ?
C014 C020 C019 111.1(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_zdf-56-1
_audit_block_doi                 10.5517/ccdc.csd.cc1ndsg9
_database_code_depnum_ccdc_archive 'CCDC 1531631'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tet.2018.01.045 2018
_audit_update_record             
;
2017-02-08 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;
_audit_creation_date             2017-01-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H25 N O4'
_chemical_formula_sum            'C19 H25 N O4'
_chemical_formula_weight         331.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_cell_length_a                   20.1905(16)
_cell_length_b                   6.6712(4)
_cell_length_c                   12.9057(9)
_cell_angle_alpha                90.0
_cell_angle_beta                 106.432(8)
_cell_angle_gamma                90.0
_cell_volume                     1667.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1977
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9610
_cell_measurement_theta_min      3.1570
_cell_oxdiff_angle_alpha         89.993(5)
_cell_oxdiff_angle_beta          106.466(8)
_cell_oxdiff_angle_gamma         90.003(7)
_cell_oxdiff_length_a            20.193(2)
_cell_oxdiff_length_b            6.6711(4)
_cell_oxdiff_length_c            12.9064(9)
_cell_oxdiff_measurement_reflns_used 1977
_cell_oxdiff_volume              1667.3(2)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61761
_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            ?
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             712.0
_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  0.0312
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7390
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.111
_diffrn_reflns_theta_min         3.156
_diffrn_ambient_temperature      293(2)
_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    2.00   38.00   1.0000    3.8950
omega____ theta____ kappa____ phi______ frames
    -       17.1042   38.0000  -60.0000 36

#__ type_ start__ end____ width___ exp.time_
  2 omega   10.00   82.00   1.0000    3.8950
omega____ theta____ kappa____ phi______ frames
    -       17.1042   77.0000    0.0000 72

#__ type_ start__ end____ width___ exp.time_
  3 omega    2.00   84.00   1.0000    3.8950
omega____ theta____ kappa____ phi______ frames
    -       17.1042   38.0000  150.0000 82

#__ type_ start__ end____ width___ exp.time_
  4 omega  -17.00   10.00   1.0000    3.8950
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000 -150.0000 27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0348325000
_diffrn_orient_matrix_UB_12      -0.0304471000
_diffrn_orient_matrix_UB_13      0.0218633000
_diffrn_orient_matrix_UB_21      0.0060207000
_diffrn_orient_matrix_UB_22      0.0157833000
_diffrn_orient_matrix_UB_23      -0.0509232000
_diffrn_orient_matrix_UB_31      0.0095950000
_diffrn_orient_matrix_UB_32      0.1006418000
_diffrn_orient_matrix_UB_33      0.0145941000
_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'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2646
_reflns_number_total             3809
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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         0.397
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3809
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1267
_refine_ls_R_factor_gt           0.0971
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1019P)²+3.3400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2420
_refine_ls_wR_factor_ref         0.2640
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C8(H8), C14(H14), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C12(H12A,H12B), C15(H15A,H15B), C17(H17A,H17B),
 C19(H19A,H19B), C23(H23A,H23B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C18(H18), C20(H20), C22(H22)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_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
O1 O 0.18581(14) 0.6960(4) 0.85164(19) 0.0394(6) Uani 1 1 d . . . . .
O2 O 0.26755(13) 0.4974(4) 0.8041(2) 0.0399(6) Uani 1 1 d . . . . .
O3 O 0.21384(14) 0.6597(4) 0.96864(19) 0.0419(6) Uani 1 1 d . . . . .
N4 N 0.33376(17) 0.6942(5) 0.9766(2) 0.0389(7) Uani 1 1 d . . . . .
C5 C 0.17114(19) 0.3295(5) 0.8256(3) 0.0371(8) Uani 1 1 d . . . . .
H5 H 0.1971 0.2986 0.9003 0.045 Uiso 1 1 calc R . . . .
O6 O 0.29699(16) 0.6856(5) 0.7804(2) 0.0572(9) Uani 1 1 d . . . . .
C8 C 0.1556(2) 0.5780(6) 0.6749(3) 0.0388(8) Uani 1 1 d . . . . .
H8 H 0.1718 0.7056 0.6534 0.047 Uiso 1 1 calc R . . . .
C9 C 0.1677(2) 0.4090(6) 0.6015(3) 0.0440(9) Uani 1 1 d . . . . .
H9A H 0.1436 0.4394 0.5269 0.053 Uiso 1 1 calc R . . . .
H9B H 0.2166 0.3989 0.6077 0.053 Uiso 1 1 calc R . . . .
C10 C 0.36165(17) 0.5077(5) 1.0234(3) 0.0337(7) Uani 1 1 d . . . . .
C11 C 0.1817(2) 0.1630(6) 0.7509(3) 0.0483(10) Uani 1 1 d . . . . .
H11A H 0.1656 0.0368 0.7721 0.058 Uiso 1 1 calc R . . . .
H11B H 0.2305 0.1496 0.7571 0.058 Uiso 1 1 calc R . . . .
C12 C 0.0944(2) 0.3488(8) 0.8173(4) 0.0546(11) Uani 1 1 d . . . . .
H12A H 0.0779 0.2253 0.8409 0.065 Uiso 1 1 calc R . . . .
H12B H 0.0876 0.4564 0.8637 0.065 Uiso 1 1 calc R . . . .
C13 C 0.4215(2) 0.1509(6) 1.1272(3) 0.0440(9) Uani 1 1 d . . . . .
C14 C 0.1420(2) 0.2108(6) 0.6333(3) 0.0468(9) Uani 1 1 d . . . . .
H14 H 0.1494 0.1039 0.5857 0.056 Uiso 1 1 calc R . . . .
C15 C 0.2757(2) 0.7754(6) 1.0029(3) 0.0451(9) Uani 1 1 d . . . . .
H15A H 0.2665 0.9077 0.9707 0.054 Uiso 1 1 calc R . . . .
H15B H 0.2873 0.7919 1.0806 0.054 Uiso 1 1 calc R . . . .
C16 C 0.3710(2) 0.2511(7) 1.1576(3) 0.0511(10) Uani 1 1 d . . . . .
H16 H 0.3560 0.1991 1.2139 0.061 Uiso 1 1 calc R . . . .
C17 C 0.3444(2) 0.7578(6) 0.8776(3) 0.0445(9) Uani 1 1 d . . . . .
H17A H 0.3906 0.7175 0.8774 0.053 Uiso 1 1 calc R . . . .
H17B H 0.3432 0.9032 0.8759 0.053 Uiso 1 1 calc R . . . .
C18 C 0.4405(2) 0.2328(7) 1.0409(4) 0.0544(11) Uani 1 1 d . . . . .
H18 H 0.4740 0.1682 1.0164 0.065 Uiso 1 1 calc R . . . .
C19 C 0.0790(2) 0.5922(7) 0.6660(4) 0.0558(11) Uani 1 1 d . . . . .
H19A H 0.0532 0.6226 0.5920 0.067 Uiso 1 1 calc R . . . .
H19B H 0.0711 0.6995 0.7119 0.067 Uiso 1 1 calc R . . . .
C20 C 0.4114(2) 0.4064(7) 0.9906(3) 0.0501(10) Uani 1 1 d . . . . .
H20 H 0.4257 0.4561 0.9331 0.060 Uiso 1 1 calc R . . . .
C21 C 0.0538(2) 0.3927(8) 0.7005(4) 0.0612(13) Uani 1 1 d . . . . .
H21 H 0.0046 0.4027 0.6952 0.073 Uiso 1 1 calc R . . . .
C22 C 0.3411(2) 0.4262(7) 1.1086(3) 0.0486(10) Uani 1 1 d . . . . .
H22 H 0.3072 0.4895 1.1326 0.058 Uiso 1 1 calc R . . . .
C23 C 0.0650(2) 0.2247(8) 0.6261(4) 0.0602(12) Uani 1 1 d . . . . .
H23A H 0.0493 0.0982 0.6475 0.072 Uiso 1 1 calc R . . . .
H23B H 0.0386 0.2525 0.5522 0.072 Uiso 1 1 calc R . . . .
C24 C 0.4549(3) -0.0351(7) 1.1842(4) 0.0643(13) Uani 1 1 d . . . . .
H24A H 0.4881 0.0012 1.2509 0.096 Uiso 1 1 calc GR . . . .
H24B H 0.4776 -0.1055 1.1392 0.096 Uiso 1 1 calc GR . . . .
H24C H 0.4202 -0.1199 1.1991 0.096 Uiso 1 1 calc GR . . . .
C1AA C 0.19610(17) 0.5281(5) 0.7917(3) 0.0310(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 O3 1.475(3) . ?
O1 C1AA 1.410(4) . ?
O2 O6 1.458(4) . ?
O2 C1AA 1.421(4) . ?
O3 C15 1.427(5) . ?
N4 C10 1.427(5) . ?
N4 C15 1.417(5) . ?
N4 C17 1.419(5) . ?
C5 C11 1.525(5) . ?
C5 C12 1.528(6) . ?
C5 C1AA 1.525(5) . ?
O6 C17 1.430(5) . ?
C8 C9 1.536(5) . ?
C8 C19 1.522(6) . ?
C8 C1AA 1.534(5) . ?
C9 C14 1.520(6) . ?
C10 C20 1.373(5) . ?
C10 C22 1.390(5) . ?
C11 C14 1.536(6) . ?
C12 C21 1.526(6) . ?
C13 C16 1.365(6) . ?
C13 C18 1.388(6) . ?
C13 C24 1.502(6) . ?
C14 C23 1.532(6) . ?
C16 C22 1.383(6) . ?
C18 C20 1.376(6) . ?
C19 C21 1.535(7) . ?
C21 C23 1.534(7) . ?

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
C1AA O1 O3 111.0(2) . . ?
C1AA O2 O6 108.3(3) . . ?
C15 O3 O1 106.1(3) . . ?
C15 N4 C10 119.1(3) . . ?
C15 N4 C17 116.6(3) . . ?
C17 N4 C10 120.0(3) . . ?
C11 C5 C12 109.7(3) . . ?
C1AA C5 C11 109.5(3) . . ?
C1AA C5 C12 108.5(3) . . ?
C17 O6 O2 108.5(3) . . ?
C19 C8 C9 109.6(3) . . ?
C19 C8 C1AA 109.6(3) . . ?
C1AA C8 C9 108.2(3) . . ?
C14 C9 C8 110.2(3) . . ?
C20 C10 N4 122.2(3) . . ?
C20 C10 C22 117.3(4) . . ?
C22 C10 N4 120.4(3) . . ?
C5 C11 C14 110.2(3) . . ?
C21 C12 C5 109.7(3) . . ?
C16 C13 C18 115.8(4) . . ?
C16 C13 C24 122.1(4) . . ?
C18 C13 C24 122.0(4) . . ?
C9 C14 C11 108.9(3) . . ?
C9 C14 C23 110.4(4) . . ?
C23 C14 C11 108.1(4) . . ?
N4 C15 O3 115.4(3) . . ?
C13 C16 C22 123.2(4) . . ?
N4 C17 O6 117.0(3) . . ?
C20 C18 C13 122.2(4) . . ?
C8 C19 C21 109.6(3) . . ?
C10 C20 C18 121.3(4) . . ?
C12 C21 C19 108.9(4) . . ?
C12 C21 C23 110.2(4) . . ?
C23 C21 C19 109.4(4) . . ?
C16 C22 C10 120.2(4) . . ?
C14 C23 C21 109.4(4) . . ?
O1 C1AA O2 110.8(3) . . ?
O1 C1AA C5 114.9(3) . . ?
O1 C1AA C8 104.3(3) . . ?
O2 C1AA C5 104.5(3) . . ?
O2 C1AA C8 112.6(3) . . ?
C5 C1AA C8 110.1(3) . . ?

_olex2_date_sample_data_collection 2017-01-10
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kls-14-4
_audit_block_doi                 10.5517/ccdc.csd.cc1z62kt
_database_code_depnum_ccdc_archive 'CCDC 1823096'
_audit_update_record             
;
2018-02-09 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;
_audit_creation_date             2018-01-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H26 Cl N O4'
_chemical_formula_sum            'C18 H26 Cl N O4'
_chemical_formula_weight         355.85
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.5582(8)
_cell_length_b                   6.0006(3)
_cell_length_c                   27.226(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.111(7)
_cell_angle_gamma                90
_cell_volume                     1852.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2244
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.5280
_cell_measurement_theta_min      1.8730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77813
_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            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             760.0
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            9047
_diffrn_reflns_point_group_measured_fraction_full 0.834
_diffrn_reflns_point_group_measured_fraction_max 0.681
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.251
_diffrn_reflns_theta_min         1.796
_diffrn_ambient_temperature      293(2)
_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  -23.00    3.00   1.0000   25.3700
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -35.00   27.00   1.0000   25.3700
omega____ theta____ kappa____ phi______ frames
    -       16.9480  -57.0000  -90.0000 62

#__ type_ start__ end____ width___ exp.time_
  3 omega  -42.00   84.00   1.0000   25.3700
omega____ theta____ kappa____ phi______ frames
    -       16.9480    0.0000  120.0000 126
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0373112000
_diffrn_orient_matrix_UB_12      0.0742294000
_diffrn_orient_matrix_UB_13      0.0160465000
_diffrn_orient_matrix_UB_21      -0.0413821000
_diffrn_orient_matrix_UB_22      0.0038864000
_diffrn_orient_matrix_UB_23      0.0161533000
_diffrn_orient_matrix_UB_31      0.0284208000
_diffrn_orient_matrix_UB_32      -0.0919792000
_diffrn_orient_matrix_UB_33      0.0136072000
_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'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4464
_reflns_number_total             6850
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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         0.235
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details 
;
 Flack x determined using 1257 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.02(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         6850
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0914
_refine_ls_R_factor_gt           0.0583
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0746P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1581
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13'(H13'), C14'(H14'), C10'(H10')
2.b Secondary CH2 refined with riding coordinates:
 C9'(H9'A,H9'B), C11'(H11C,H11D), C5'(H5'A,H5'B), C3'(H3'A,H3'B), C12'(H12C,
 H12D)
2.c Aromatic/amide H refined with riding coordinates:
 C19'(H19'), C20'(H20'), C22'(H22'), C23'(H23')
2.d Idealised Me refined as rotating group:
 C17'(H17D,H17E,H17F), C16(H16A,H16B,H16C), C16'(H16D,H16E,H16F), C15'(H15D,
 H15E,H15F), C15(H15A,H15B,H15C)
;
_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
Cl1 Cl 0.37452(16) 0.2502(4) 0.29531(8) 0.1169(7) Uani 1 1 d . . . . .
Cl1' Cl 0.56262(14) -0.5869(4) 0.21111(8) 0.1265(8) Uani 1 1 d . . . . .
O1' O -0.0496(3) -0.2548(5) 0.04788(10) 0.0552(8) Uani 1 1 d . . . . .
O7' O -0.0421(2) 0.0175(4) 0.10891(12) 0.0550(8) Uani 1 1 d . . . . .
O2' O 0.0666(3) -0.3375(6) 0.04465(11) 0.0606(8) Uani 1 1 d . . . . .
O6' O 0.0767(3) 0.0608(5) 0.13449(13) 0.0635(9) Uani 1 1 d . . . . .
O7 O -0.1409(2) -0.4046(5) 0.38903(11) 0.0520(7) Uani 1 1 d . . . . .
C8' C -0.0645(3) -0.2118(6) 0.09794(14) 0.0415(9) Uani 1 1 d . . . . .
O1 O -0.1074(3) -0.1284(5) 0.44931(11) 0.0584(8) Uani 1 1 d . . . . .
O2 O 0.0101(3) -0.0345(6) 0.45337(12) 0.0676(9) Uani 1 1 d . . . . .
C9' C 0.0044(4) -0.3680(7) 0.13562(15) 0.0481(10) Uani 1 1 d . . . . .
H9'A H 0.0878 -0.3378 0.1384 0.058 Uiso 1 1 calc R . . . .
H9'B H -0.0100 -0.5198 0.1237 0.058 Uiso 1 1 calc R . . . .
C13 C -0.2941(4) -0.1676(8) 0.40034(18) 0.0531(11) Uani 1 1 d . . . . .
H13 H -0.300(4) -0.015(8) 0.4103(17) 0.064 Uiso 1 1 d R . . . .
N4' N 0.2021(3) -0.0519(7) 0.07922(17) 0.0649(11) Uani 1 1 d . . . . .
C9 C -0.1297(4) -0.0166(8) 0.36205(17) 0.0496(10) Uani 1 1 d . . . . .
H9A H -0.043(4) -0.032(8) 0.3663(17) 0.059 Uiso 1 1 d R . . . .
H9B H -0.143(4) 0.125(9) 0.3741(16) 0.059 Uiso 1 1 d R . . . .
O6 O -0.0419(3) -0.4360(5) 0.36364(14) 0.0657(9) Uani 1 1 d . . . . .
N4 N 0.1268(3) -0.3072(8) 0.42114(18) 0.0719(12) Uani 1 1 d . . . . .
C13' C -0.1977(4) -0.2377(8) 0.09398(16) 0.0523(11) Uani 1 1 d . . . . .
H13' H -0.2146 -0.3928 0.0837 0.063 Uiso 1 1 calc R . . . .
C14 C -0.3338(4) -0.3099(8) 0.4411(2) 0.0616(13) Uani 1 1 d . . . . .
H14 H -0.274(4) -0.317(9) 0.4635(19) 0.074 Uiso 1 1 d R . . . .
C18' C 0.2876(4) -0.1788(8) 0.11048(19) 0.0567(11) Uani 1 1 d . . . . .
C11' C -0.1578(5) -0.3800(11) 0.18258(18) 0.0753(15) Uani 1 1 d . . . . .
H11C H -0.1786 -0.5316 0.1720 0.090 Uiso 1 1 calc R . . . .
H11D H -0.1780 -0.3584 0.2152 0.090 Uiso 1 1 calc R . . . .
C5' C 0.1467(4) 0.1272(8) 0.0994(2) 0.0772(16) Uani 1 1 d . . . . .
H5'A H 0.0971 0.2065 0.0721 0.093 Uiso 1 1 calc R . . . .
H5'B H 0.2069 0.2299 0.1156 0.093 Uiso 1 1 calc R . . . .
C10 C -0.2022(5) -0.0516(9) 0.30996(17) 0.0627(13) Uani 1 1 d . . . . .
H10 H -0.188(4) -0.203(10) 0.2993(19) 0.075 Uiso 1 1 d R . . . .
C19' C 0.3346(4) -0.3686(10) 0.0941(2) 0.0697(14) Uani 1 1 d . . . . .
H19' H 0.3079 -0.4151 0.0613 0.084 Uiso 1 1 calc R . . . .
C14' C -0.2751(4) -0.0972(8) 0.0532(2) 0.0625(13) Uani 1 1 d . . . . .
H14' H -0.2298 -0.0763 0.0266 0.075 Uiso 1 1 calc R . . . .
C11 C -0.3304(6) -0.0371(13) 0.3116(2) 0.0827(18) Uani 1 1 d . . . . .
H11A H -0.361(5) 0.129(12) 0.323(2) 0.099 Uiso 1 1 d R . . . .
H11B H -0.375(5) -0.048(11) 0.283(2) 0.099 Uiso 1 1 d R . . . .
C10' C -0.0267(4) -0.3490(9) 0.18698(16) 0.0618(13) Uani 1 1 d . . . . .
H10' H -0.0063 -0.1984 0.1997 0.074 Uiso 1 1 calc R . . . .
C19 C 0.2475(5) 0.0113(10) 0.4091(2) 0.0734(15) Uani 1 1 d . . . . .
H19 H 0.253(5) 0.049(10) 0.442(2) 0.088 Uiso 1 1 d R . . . .
C3' C 0.1365(4) -0.1535(10) 0.03498(19) 0.0717(15) Uani 1 1 d . . . . .
H3'A H 0.0853 -0.0422 0.0161 0.086 Uiso 1 1 calc R . . . .
H3'B H 0.1910 -0.2035 0.0143 0.086 Uiso 1 1 calc R . . . .
C12' C -0.2285(4) -0.2204(10) 0.1458(2) 0.0696(14) Uani 1 1 d . . . . .
H12C H -0.2140 -0.0693 0.1581 0.083 Uiso 1 1 calc R . . . .
H12D H -0.3118 -0.2514 0.1433 0.083 Uiso 1 1 calc R . . . .
C20' C 0.4186(5) -0.4910(10) 0.1242(2) 0.0795(16) Uani 1 1 d . . . . .
H20' H 0.4493 -0.6176 0.1117 0.095 Uiso 1 1 calc R . . . .
C21 C 0.3029(4) 0.0841(11) 0.3324(2) 0.0777(16) Uani 1 1 d . . . . .
C17 C -0.1645(7) 0.1211(14) 0.2749(2) 0.092(2) Uani 1 1 d . . . . .
H17A H -0.172(6) 0.259(14) 0.291(3) 0.138 Uiso 1 1 d R . . . .
H17B H -0.211(6) 0.105(16) 0.247(3) 0.138 Uiso 1 1 d R . . . .
H17C H -0.074(6) 0.101(15) 0.276(3) 0.138 Uiso 1 1 d R . . . .
C5 C 0.0601(5) -0.4913(9) 0.4001(3) 0.0778(17) Uani 1 1 d . . . . .
H5A H 0.031(5) -0.593(10) 0.424(2) 0.093 Uiso 1 1 d R . . . .
H5B H 0.113(5) -0.587(11) 0.385(2) 0.093 Uiso 1 1 d R . . . .
C3 C 0.0940(5) -0.2109(14) 0.4642(2) 0.0799(18) Uani 1 1 d . . . . .
H3A H 0.157(5) -0.130(10) 0.481(2) 0.096 Uiso 1 1 d R . . . .
H3B H 0.061(5) -0.342(11) 0.479(2) 0.096 Uiso 1 1 d R . . . .
C20 C 0.3060(5) 0.1412(11) 0.3806(2) 0.0768(15) Uani 1 1 d . . . . .
H20 H 0.329(5) 0.294(11) 0.393(2) 0.092 Uiso 1 1 d R . . . .
C21' C 0.4579(4) -0.4284(12) 0.1726(3) 0.0811(18) Uani 1 1 d . . . . .
C18 C 0.1859(4) -0.1733(9) 0.3912(2) 0.0638(13) Uani 1 1 d . . . . .
C12 C -0.3658(5) -0.2041(11) 0.3478(2) 0.0736(15) Uani 1 1 d . . . . .
H12A H -0.355(5) -0.358(10) 0.336(2) 0.088 Uiso 1 1 d R . . . .
H12B H -0.457(4) -0.195(10) 0.3494(19) 0.088 Uiso 1 1 d R . . . .
C22' C 0.4140(5) -0.2424(15) 0.1900(3) 0.101(2) Uani 1 1 d . . . . .
H22' H 0.4414 -0.1972 0.2228 0.122 Uiso 1 1 calc R . . . .
C17' C 0.0454(5) -0.5137(11) 0.22250(19) 0.0868(18) Uani 1 1 d . . . . .
H17D H 0.0327 -0.6614 0.2090 0.130 Uiso 1 1 calc GR . . . .
H17E H 0.0216 -0.5074 0.2544 0.130 Uiso 1 1 calc GR . . . .
H17F H 0.1275 -0.4766 0.2266 0.130 Uiso 1 1 calc GR . . . .
C16 C -0.3561(6) -0.5490(9) 0.4290(3) 0.0875(18) Uani 1 1 d . . . . .
H16A H -0.4166 -0.5623 0.3995 0.131 Uiso 1 1 calc GR . . . .
H16B H -0.3812 -0.6220 0.4565 0.131 Uiso 1 1 calc GR . . . .
H16C H -0.2850 -0.6175 0.4231 0.131 Uiso 1 1 calc GR . . . .
C23' C 0.3286(5) -0.1190(11) 0.1593(2) 0.0894(18) Uani 1 1 d . . . . .
H23' H 0.2982 0.0074 0.1720 0.107 Uiso 1 1 calc R . . . .
C16' C -0.3049(5) 0.1303(10) 0.0692(3) 0.096(2) Uani 1 1 d . . . . .
H16D H -0.3523 0.1179 0.0944 0.144 Uiso 1 1 calc GR . . . .
H16E H -0.3479 0.2100 0.0409 0.144 Uiso 1 1 calc GR . . . .
H16F H -0.2335 0.2093 0.0826 0.144 Uiso 1 1 calc GR . . . .
C15' C -0.3854(5) -0.2207(13) 0.0301(3) 0.114(3) Uani 1 1 d . . . . .
H15D H -0.3647 -0.3621 0.0177 0.171 Uiso 1 1 calc GR . . . .
H15E H -0.4289 -0.1349 0.0029 0.171 Uiso 1 1 calc GR . . . .
H15F H -0.4331 -0.2439 0.0549 0.171 Uiso 1 1 calc GR . . . .
C8 C -0.1627(4) -0.1787(6) 0.39907(15) 0.0433(9) Uani 1 1 d . . . . .
C22 C 0.2432(8) -0.0959(18) 0.3139(3) 0.129(3) Uani 1 1 d . . . . .
H22 H 0.251(7) -0.124(16) 0.284(3) 0.155 Uiso 1 1 d R . . . .
C15 C -0.4378(7) -0.2073(13) 0.4581(3) 0.137(4) Uani 1 1 d . . . . .
H15A H -0.4188 -0.0576 0.4693 0.206 Uiso 1 1 calc GR . . . .
H15B H -0.4570 -0.2934 0.4852 0.206 Uiso 1 1 calc GR . . . .
H15C H -0.5041 -0.2052 0.4308 0.206 Uiso 1 1 calc GR . . . .
C23 C 0.1859(8) -0.2254(16) 0.3431(3) 0.125(3) Uani 1 1 d . . . . .
H23 H 0.154(7) -0.349(15) 0.330(3) 0.150 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C21 1.738(6) . ?
Cl1' C21' 1.727(6) . ?
O1' O2' 1.450(4) . ?
O1' C8' 1.430(5) . ?
O7' O6' 1.438(4) . ?
O7' C8' 1.421(5) . ?
O2' C3' 1.423(6) . ?
O6' C5' 1.424(6) . ?
O7 O6 1.458(4) . ?
O7 C8 1.415(5) . ?
C8' C9' 1.500(6) . ?
C8' C13' 1.531(5) . ?
O1 O2 1.455(4) . ?
O1 C8 1.426(5) . ?
O2 C3 1.427(8) . ?
C9' C10' 1.513(6) . ?
C13 C14 1.538(7) . ?
C13 C12 1.524(7) . ?
C13 C8 1.527(6) . ?
N4' C18' 1.399(6) . ?
N4' C5' 1.414(7) . ?
N4' C3' 1.430(7) . ?
C9 C10 1.517(7) . ?
C9 C8 1.502(6) . ?
O6 C5 1.426(7) . ?
N4 C5 1.405(7) . ?
N4 C3 1.422(8) . ?
N4 C18 1.411(6) . ?
C13' C14' 1.537(6) . ?
C13' C12' 1.523(7) . ?
C14 C16 1.484(8) . ?
C14 C15 1.502(7) . ?
C18' C19' 1.372(7) . ?
C18' C23' 1.371(7) . ?
C11' C10' 1.508(7) . ?
C11' C12' 1.508(7) . ?
C10 C11 1.494(8) . ?
C10 C17 1.529(8) . ?
C19' C20' 1.359(7) . ?
C14' C16' 1.494(8) . ?
C14' C15' 1.503(7) . ?
C11 C12 1.517(9) . ?
C10' C17' 1.515(7) . ?
C19 C20 1.368(8) . ?
C19 C18 1.356(8) . ?
C20' C21' 1.360(8) . ?
C21 C20 1.352(8) . ?
C21 C22 1.327(11) . ?
C21' C22' 1.349(10) . ?
C18 C23 1.346(9) . ?
C22' C23' 1.379(9) . ?
C22 C23 1.370(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8' O1' O2' 113.8(3) . . ?
C8' O7' O6' 113.3(3) . . ?
C3' O2' O1' 108.1(3) . . ?
C5' O6' O7' 109.8(4) . . ?
C8 O7 O6 113.6(3) . . ?
O1' C8' C9' 113.2(3) . . ?
O1' C8' C13' 102.7(3) . . ?
O7' C8' O1' 108.9(3) . . ?
O7' C8' C9' 114.2(3) . . ?
O7' C8' C13' 104.7(3) . . ?
C9' C8' C13' 112.2(3) . . ?
C8 O1 O2 113.2(3) . . ?
C3 O2 O1 108.4(4) . . ?
C8' C9' C10' 113.3(4) . . ?
C12 C13 C14 114.4(4) . . ?
C12 C13 C8 109.6(4) . . ?
C8 C13 C14 115.3(4) . . ?
C18' N4' C5' 119.8(5) . . ?
C18' N4' C3' 118.6(4) . . ?
C5' N4' C3' 116.4(4) . . ?
C8 C9 C10 111.8(4) . . ?
C5 O6 O7 108.6(4) . . ?
C5 N4 C3 116.4(5) . . ?
C5 N4 C18 120.0(5) . . ?
C18 N4 C3 118.7(5) . . ?
C8' C13' C14' 115.6(4) . . ?
C12' C13' C8' 109.8(3) . . ?
C12' C13' C14' 115.1(4) . . ?
C16 C14 C13 116.1(5) . . ?
C16 C14 C15 110.5(5) . . ?
C15 C14 C13 111.3(4) . . ?
C19' C18' N4' 122.1(5) . . ?
C23' C18' N4' 121.3(5) . . ?
C23' C18' C19' 116.6(5) . . ?
C12' C11' C10' 112.5(4) . . ?
N4' C5' O6' 114.0(4) . . ?
C9 C10 C17 108.5(5) . . ?
C11 C10 C9 109.7(4) . . ?
C11 C10 C17 112.5(5) . . ?
C20' C19' C18' 122.3(5) . . ?
C16' C14' C13' 115.1(5) . . ?
C16' C14' C15' 110.4(5) . . ?
C15' C14' C13' 111.1(5) . . ?
C10 C11 C12 111.9(5) . . ?
C9' C10' C17' 110.0(4) . . ?
C11' C10' C9' 109.3(4) . . ?
C11' C10' C17' 113.0(5) . . ?
C18 C19 C20 122.9(6) . . ?
O2' C3' N4' 113.8(4) . . ?
C11' C12' C13' 112.2(4) . . ?
C19' C20' C21' 120.0(6) . . ?
C20 C21 Cl1 119.5(5) . . ?
C22 C21 Cl1 121.2(5) . . ?
C22 C21 C20 119.3(6) . . ?
N4 C5 O6 114.6(4) . . ?
N4 C3 O2 114.2(4) . . ?
C21 C20 C19 119.0(6) . . ?
C20' C21' Cl1' 120.0(6) . . ?
C22' C21' Cl1' 120.6(6) . . ?
C22' C21' C20' 119.4(6) . . ?
C19 C18 N4 122.4(5) . . ?
C23 C18 N4 121.4(6) . . ?
C23 C18 C19 116.2(6) . . ?
C11 C12 C13 110.5(5) . . ?
C21' C22' C23' 120.3(6) . . ?
C18' C23' C22' 121.3(6) . . ?
O7 C8 O1 108.9(3) . . ?
O7 C8 C13 105.1(3) . . ?
O7 C8 C9 114.4(3) . . ?
O1 C8 C13 103.5(3) . . ?
O1 C8 C9 112.4(3) . . ?
C9 C8 C13 111.7(4) . . ?
C21 C22 C23 121.1(7) . . ?
C18 C23 C22 121.5(7) . . ?

_olex2_date_sample_data_collection 2017-11-14
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hgm-515-8
_audit_block_doi                 10.5517/ccdc.csd.cc1ndsf8
_database_code_depnum_ccdc_archive 'CCDC 1531630'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tet.2018.01.045 2018
_audit_update_record             
;
2017-02-08 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;
_audit_creation_date             2016-05-12
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H22 F N O4'
_chemical_formula_sum            'C18 H22 F N O4'
_chemical_formula_weight         335.37
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   12.6170(10)
_cell_length_b                   6.6369(5)
_cell_length_c                   19.1450(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1603.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1580
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4630
_cell_measurement_theta_min      3.2330
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64030
_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            ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             712.0
_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  0.0248
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.867
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5095
_diffrn_reflns_point_group_measured_fraction_full 0.857
_diffrn_reflns_point_group_measured_fraction_max 0.711
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.117
_diffrn_reflns_theta_min         2.128
_diffrn_ambient_temperature      293(2)
_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  -25.00   23.00   1.0000    6.4550
omega____ theta____ kappa____ phi______ frames
    -      -16.4011  -99.0000 -150.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega   35.00   89.00   1.0000    6.4550
omega____ theta____ kappa____ phi______ frames
    -       17.1042  178.0000    0.0000 54

#__ type_ start__ end____ width___ exp.time_
  3 omega  -10.00   45.00   1.0000    6.4550
omega____ theta____ kappa____ phi______ frames
    -       17.1042   77.0000    0.0000 55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0230085000
_diffrn_orient_matrix_UB_12      0.0130123000
_diffrn_orient_matrix_UB_13      -0.0335187000
_diffrn_orient_matrix_UB_21      0.0488707000
_diffrn_orient_matrix_UB_22      -0.0374559000
_diffrn_orient_matrix_UB_23      0.0128419000
_diffrn_orient_matrix_UB_31      -0.0154306000
_diffrn_orient_matrix_UB_32      -0.0992912000
_diffrn_orient_matrix_UB_33      -0.0092288000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.595
_reflns_Friedel_fraction_full    0.707
_reflns_Friedel_fraction_max     0.546
_reflns_number_gt                2348
_reflns_number_total             3064
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 770 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   1.4(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.806
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      0.806
_refine_ls_shift/su_max          0.003
_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          0.1096
_refine_ls_wR_factor_ref         0.1275
_refine_special_details          
;
 ?
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.39748(18) 0.2817(4) 0.27517(14) 0.0368(6) Uani 1 1 d . . . . .
O2 O 0.49895(18) 0.3221(4) 0.24131(15) 0.0394(6) Uani 1 1 d . . . . .
O3 O 0.3071(2) 0.4911(4) 0.19777(12) 0.0364(6) Uani 1 1 d . . . . .
O4 O 0.2724(2) 0.3015(5) 0.16599(14) 0.0479(7) Uani 1 1 d . . . . .
C5 C 0.4918(2) 0.4971(6) 0.09511(18) 0.0349(7) Uani 1 1 d . . . . .
C6 C 0.3750(3) 0.6466(5) 0.29718(19) 0.0345(8) Uani 1 1 d . . . . .
C7 C 0.2219(4) 0.7275(7) 0.4091(2) 0.0517(11) Uani 1 1 d . . . . .
N8 N 0.4496(2) 0.3122(5) 0.11933(17) 0.0388(7) Uani 1 1 d . . . . .
C9 C 0.3296(2) 0.4508(5) 0.26904(18) 0.0281(7) Uani 1 1 d . . . . .
C10 C 0.4034(3) 0.6175(8) 0.3743(2) 0.0465(10) Uani 1 1 d . . . . .
C11 C 0.1924(3) 0.7556(6) 0.3322(2) 0.0418(9) Uani 1 1 d . . . . .
F12 F 0.6244(3) 1.0254(5) 0.02186(18) 0.0815(9) Uani 1 1 d . . . . .
C13 C 0.2307(3) 0.3901(6) 0.3107(2) 0.0352(8) Uani 1 1 d . . . . .
C14 C 0.5002(3) 0.2137(6) 0.1759(2) 0.0427(9) Uani 1 1 d . . . . .
C15 C 0.5826(3) 0.5766(7) 0.1243(2) 0.0465(10) Uani 1 1 d . . . . .
C16 C 0.6275(4) 0.7521(8) 0.0998(2) 0.0516(11) Uani 1 1 d . . . . .
C17 C 0.1486(3) 0.5589(6) 0.3027(2) 0.0409(9) Uani 1 1 d . . . . .
C18 C 0.2925(3) 0.8131(6) 0.2914(2) 0.0430(9) Uani 1 1 d . . . . .
C19 C 0.3410(3) 0.2635(7) 0.1077(2) 0.0449(10) Uani 1 1 d . . . . .
C20 C 0.3048(3) 0.5622(7) 0.4161(2) 0.0492(10) Uani 1 1 d . . . . .
C21 C 0.5812(4) 0.8498(7) 0.0455(2) 0.0513(10) Uani 1 1 d . . . . .
C22 C 0.2607(4) 0.3633(7) 0.3875(2) 0.0485(10) Uani 1 1 d . . . . .
C23 C 0.4486(4) 0.6002(8) 0.0389(3) 0.0659(14) Uani 1 1 d . . . . .
C24 C 0.4932(5) 0.7779(9) 0.0152(3) 0.0757(17) Uani 1 1 d . . . . .
H6 H 0.435(3) 0.676(5) 0.272(2) 0.029(9) Uiso 1 1 d . . . . .
H22A H 0.309(4) 0.249(7) 0.395(2) 0.044(11) Uiso 1 1 d . . . . .
H18A H 0.274(4) 0.842(8) 0.244(3) 0.054(12) Uiso 1 1 d . . . . .
H18B H 0.327(4) 0.937(7) 0.312(3) 0.050(12) Uiso 1 1 d . . . . .
H17A H 0.132(3) 0.581(6) 0.250(2) 0.030(9) Uiso 1 1 d . . . . .
H10A H 0.439(4) 0.736(7) 0.393(2) 0.045(11) Uiso 1 1 d . . . . .
H22B H 0.195(4) 0.331(6) 0.410(2) 0.038(10) Uiso 1 1 d . . . . .
H7A H 0.251(3) 0.855(7) 0.428(2) 0.037(10) Uiso 1 1 d . . . . .
H15 H 0.615(4) 0.515(8) 0.163(3) 0.053(12) Uiso 1 1 d . . . . .
H13 H 0.206(3) 0.263(7) 0.297(2) 0.039(11) Uiso 1 1 d . . . . .
H16 H 0.690(5) 0.800(8) 0.119(3) 0.082(17) Uiso 1 1 d . . . . .
H17B H 0.082(3) 0.528(7) 0.330(2) 0.045(11) Uiso 1 1 d . . . . .
H24 H 0.459(4) 0.837(9) -0.024(3) 0.078(17) Uiso 1 1 d . . . . .
H19A H 0.333(3) 0.111(7) 0.105(2) 0.050(12) Uiso 1 1 d . . . . .
H20 H 0.328(4) 0.554(8) 0.460(3) 0.071(15) Uiso 1 1 d . . . . .
H23 H 0.392(5) 0.542(11) 0.019(4) 0.10(2) Uiso 1 1 d . . . . .
H11 H 0.134(3) 0.859(6) 0.325(2) 0.036(10) Uiso 1 1 d . . . . .
H19B H 0.313(5) 0.335(10) 0.069(3) 0.086(19) Uiso 1 1 d . . . . .
H7B H 0.161(6) 0.698(10) 0.437(4) 0.09(2) Uiso 1 1 d . . . . .
H14A H 0.466(3) 0.080(5) 0.1835(18) 0.023(8) Uiso 1 1 d . . . . .
H14B H 0.579(4) 0.198(6) 0.168(2) 0.044(11) Uiso 1 1 d . . . . .
H10B H 0.453(4) 0.506(7) 0.379(2) 0.046(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 O2 1.460(3) . ?
O1 C9 1.417(4) . ?
O2 C14 1.443(5) . ?
O3 O4 1.465(4) . ?
O3 C9 1.419(4) . ?
O4 C19 1.434(4) . ?
C5 N8 1.416(5) . ?
C5 C15 1.379(5) . ?
C5 C23 1.386(6) . ?
C6 C9 1.519(5) . ?
C6 C10 1.532(5) . ?
C6 C18 1.522(6) . ?
C7 C11 1.530(6) . ?
C7 C20 1.521(7) . ?
N8 C14 1.417(5) . ?
N8 C19 1.425(5) . ?
C9 C13 1.535(4) . ?
C10 C20 1.523(6) . ?
C11 C17 1.526(6) . ?
C11 C18 1.533(6) . ?
F12 C21 1.364(5) . ?
C13 C17 1.533(6) . ?
C13 C22 1.528(6) . ?
C15 C16 1.378(6) . ?
C16 C21 1.357(7) . ?
C20 C22 1.534(7) . ?
C21 C24 1.341(7) . ?
C23 C24 1.383(7) . ?

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
C9 O1 O2 110.4(2) . . ?
C14 O2 O1 107.6(2) . . ?
C9 O3 O4 107.3(2) . . ?
C19 O4 O3 107.1(3) . . ?
C15 C5 N8 120.7(3) . . ?
C15 C5 C23 116.9(4) . . ?
C23 C5 N8 122.3(3) . . ?
C9 C6 C10 108.8(3) . . ?
C9 C6 C18 109.7(3) . . ?
C18 C6 C10 108.7(3) . . ?
C20 C7 C11 109.9(3) . . ?
C5 N8 C14 118.7(3) . . ?
C5 N8 C19 120.5(3) . . ?
C14 N8 C19 116.6(3) . . ?
O1 C9 O3 110.5(3) . . ?
O1 C9 C6 114.8(3) . . ?
O1 C9 C13 103.9(3) . . ?
O3 C9 C6 104.8(3) . . ?
O3 C9 C13 112.8(3) . . ?
C6 C9 C13 110.3(3) . . ?
C20 C10 C6 110.2(3) . . ?
C7 C11 C18 108.6(4) . . ?
C17 C11 C7 109.9(4) . . ?
C17 C11 C18 108.8(3) . . ?
C17 C13 C9 107.8(3) . . ?
C22 C13 C9 109.2(3) . . ?
C22 C13 C17 110.4(3) . . ?
N8 C14 O2 115.4(3) . . ?
C16 C15 C5 121.8(4) . . ?
C21 C16 C15 119.1(4) . . ?
C11 C17 C13 110.1(3) . . ?
C6 C18 C11 110.3(3) . . ?
N8 C19 O4 114.8(3) . . ?
C7 C20 C10 110.0(4) . . ?
C7 C20 C22 109.8(4) . . ?
C10 C20 C22 108.4(4) . . ?
C16 C21 F12 119.4(4) . . ?
C24 C21 F12 119.4(5) . . ?
C24 C21 C16 121.2(5) . . ?
C13 C22 C20 109.5(4) . . ?
C24 C23 C5 121.0(4) . . ?
C21 C24 C23 119.9(5) . . ?

_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_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.
;
_shelxl_version_number           2013-4
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_kls-15-4
_audit_block_doi                 10.5517/ccdc.csd.cc1z62lv
_database_code_depnum_ccdc_archive 'CCDC 1823097'
_audit_update_record             
;
2018-02-09 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;
_audit_creation_date             2017-11-29
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H26 Cl N O4'
_chemical_formula_sum            'C18 H26 Cl N O4'
_chemical_formula_weight         355.85
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.146(2)
_cell_length_b                   6.0004(7)
_cell_length_c                   14.022(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.03(2)
_cell_angle_gamma                90
_cell_volume                     947.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1064
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.3260
_cell_measurement_theta_min      2.9790
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55303
_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            colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             380.0
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_unetI/netI     0.0758
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4826
_diffrn_reflns_point_group_measured_fraction_full 0.871
_diffrn_reflns_point_group_measured_fraction_max 0.720
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.966
_diffrn_reflns_theta_min         1.809
_diffrn_ambient_temperature      293(2)
_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  -22.00   50.00   1.0000   23.1000
omega____ theta____ kappa____ phi______ frames
    -      -16.0886   38.0000  -60.0000 72

#__ type_ start__ end____ width___ exp.time_
  2 omega  -36.00    3.00   1.0000   23.1000
omega____ theta____ kappa____ phi______ frames
    -      -16.0886  -38.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega  -24.00   10.00   1.0000   23.1000
omega____ theta____ kappa____ phi______ frames
    -      -16.0886  -99.0000   60.0000 34

#__ type_ start__ end____ width___ exp.time_
  4 omega  -85.00    3.00   1.0000   23.1000
omega____ theta____ kappa____ phi______ frames
    -      -16.0886  -38.0000  150.0000 88
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0486184000
_diffrn_orient_matrix_UB_12      -0.0088401000
_diffrn_orient_matrix_UB_13      -0.0476925000
_diffrn_orient_matrix_UB_21      0.0391833000
_diffrn_orient_matrix_UB_22      0.0124561000
_diffrn_orient_matrix_UB_23      -0.0265432000
_diffrn_orient_matrix_UB_31      0.0078658000
_diffrn_orient_matrix_UB_32      -0.1172478000
_diffrn_orient_matrix_UB_33      0.0008784000
_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'
_reflns_Friedel_coverage         0.499
_reflns_Friedel_fraction_full    0.713
_reflns_Friedel_fraction_max     0.528
_reflns_number_gt                1780
_reflns_number_total             3613
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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         0.215
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Flack x determined using 497 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.05(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3613
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0675
_refine_ls_restrained_S_all      1.052
_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)+(0.0893P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1746
_refine_ls_wR_factor_ref         0.2241
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C14(H14), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C9(H9A,H9B), C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C22(H22), C23(H23), C21(H21)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C15(H15A,H15B,H15C)
;
_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
Cl1 Cl -0.6864(3) -0.6988(5) -0.2539(2) 0.1445(13) Uani 1 1 d . . . . .
N4 N -0.9329(5) -1.3041(10) -0.1709(5) 0.0763(16) Uani 1 1 d . . . . .
O2 O -1.0179(4) -1.0093(8) -0.1055(3) 0.0759(13) Uani 1 1 d . . . . .
O7 O -1.2019(4) -1.3983(6) -0.2139(4) 0.0672(11) Uani 1 1 d . . . . .
O6 O -1.1264(4) -1.4518(6) -0.2718(4) 0.0742(13) Uani 1 1 d . . . . .
O1 O -1.1280(4) -1.0981(7) -0.1024(3) 0.0696(13) Uani 1 1 d . . . . .
C18 C -0.8989(6) -1.1963(12) -0.2447(6) 0.0705(18) Uani 1 1 d . . . . .
C13 C -1.3335(6) -1.1407(11) -0.1870(5) 0.0683(17) Uani 1 1 d . . . . .
H13 H -1.3397 -0.9820 -0.1733 0.082 Uiso 1 1 calc R . . . .
C8 C -1.2139(5) -1.1641(9) -0.2004(4) 0.0552(14) Uani 1 1 d . . . . .
C19 C -0.8211(6) -1.0193(14) -0.2185(6) 0.081(2) Uani 1 1 d . . . . .
H19 H -0.7927 -0.9660 -0.1514 0.097 Uiso 1 1 calc R . . . .
C14 C -1.3425(6) -1.2622(12) -0.0935(6) 0.0764(19) Uani 1 1 d . . . . .
H14 H -1.2656 -1.2453 -0.0365 0.092 Uiso 1 1 calc R . . . .
C3 C -0.9311(6) -1.1852(15) -0.0832(5) 0.082(2) Uani 1 1 d . . . . .
H3A H -0.8527 -1.1213 -0.0490 0.099 Uiso 1 1 calc R . . . .
H3B H -0.9447 -1.2891 -0.0358 0.099 Uiso 1 1 calc R . . . .
C16 C -1.3689(7) -1.5090(14) -0.1069(7) 0.096(2) Uani 1 1 d . . . . .
H16A H -1.4467 -1.5314 -0.1585 0.144 Uiso 1 1 calc GR . . . .
H16B H -1.3657 -1.5714 -0.0429 0.144 Uiso 1 1 calc GR . . . .
H16C H -1.3110 -1.5810 -0.1279 0.144 Uiso 1 1 calc GR . . . .
C5 C -1.0073(6) -1.4954(13) -0.1999(7) 0.090(2) Uani 1 1 d . . . . .
H5A H -1.0119 -1.5618 -0.1384 0.108 Uiso 1 1 calc R . . . .
H5B H -0.9707 -1.6037 -0.2301 0.108 Uiso 1 1 calc R . . . .
C9 C -1.2081(6) -1.0236(11) -0.2877(5) 0.0630(15) Uani 1 1 d . . . . .
H9A H -1.1334 -1.0513 -0.2957 0.076 Uiso 1 1 calc R . . . .
H9B H -1.2104 -0.8673 -0.2709 0.076 Uiso 1 1 calc R . . . .
C12 C -1.4357(6) -1.1849(15) -0.2890(7) 0.089(2) Uani 1 1 d . . . . .
H12A H -1.4348 -1.3406 -0.3072 0.107 Uiso 1 1 calc R . . . .
H12B H -1.5104 -1.1558 -0.2810 0.107 Uiso 1 1 calc R . . . .
C22 C -0.9027(9) -1.162(2) -0.4168(8) 0.120(3) Uani 1 1 d . . . . .
H22 H -0.9303 -1.2148 -0.4841 0.144 Uiso 1 1 calc R . . . .
C10 C -1.3116(7) -1.0742(14) -0.3902(5) 0.082(2) Uani 1 1 d . . . . .
H10 H -1.3061 -1.2304 -0.4083 0.098 Uiso 1 1 calc R . . . .
C23 C -0.9419(8) -1.2642(16) -0.3472(7) 0.096(2) Uani 1 1 d . . . . .
H23 H -0.9973 -1.3788 -0.3688 0.115 Uiso 1 1 calc R . . . .
C11 C -1.4281(7) -1.0414(18) -0.3748(7) 0.102(3) Uani 1 1 d . . . . .
H11A H -1.4357 -0.8860 -0.3592 0.123 Uiso 1 1 calc R . . . .
H11B H -1.4937 -1.0775 -0.4383 0.123 Uiso 1 1 calc R . . . .
C20 C -0.7846(7) -0.9196(15) -0.2905(7) 0.090(2) Uani 1 1 d . . . . .
C21 C -0.8258(8) -0.989(2) -0.3912(7) 0.108(3) Uani 1 1 d . . . . .
H21 H -0.8019 -0.9201 -0.4396 0.130 Uiso 1 1 calc R . . . .
C17 C -1.3005(8) -0.9278(18) -0.4746(6) 0.116(3) Uani 1 1 d . . . . .
H17A H -1.3092 -0.7742 -0.4595 0.174 Uiso 1 1 calc GR . . . .
H17B H -1.3613 -0.9668 -0.5394 0.174 Uiso 1 1 calc GR . . . .
H17C H -1.2239 -0.9498 -0.4783 0.174 Uiso 1 1 calc GR . . . .
C15 C -1.4364(10) -1.1558(18) -0.0595(8) 0.136(4) Uani 1 1 d . . . . .
H15A H -1.4164 -1.0024 -0.0421 0.203 Uiso 1 1 calc GR . . . .
H15B H -1.4389 -1.2336 -0.0006 0.203 Uiso 1 1 calc GR . . . .
H15C H -1.5127 -1.1647 -0.1146 0.203 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C20 1.727(9) . ?
N4 C18 1.407(9) . ?
N4 C3 1.414(9) . ?
N4 C5 1.423(10) . ?
O2 O1 1.455(6) . ?
O2 C3 1.441(9) . ?
O7 O6 1.470(6) . ?
O7 C8 1.433(7) . ?
O6 C5 1.444(8) . ?
O1 C8 1.433(7) . ?
C18 C19 1.376(10) . ?
C18 C23 1.394(10) . ?
C13 C8 1.539(8) . ?
C13 C14 1.539(9) . ?
C13 C12 1.525(10) . ?
C8 C9 1.509(8) . ?
C19 C20 1.382(10) . ?
C14 C16 1.512(11) . ?
C14 C15 1.531(10) . ?
C9 C10 1.544(9) . ?
C12 C11 1.511(11) . ?
C22 C23 1.379(12) . ?
C22 C21 1.353(14) . ?
C10 C11 1.522(11) . ?
C10 C17 1.520(10) . ?
C20 C21 1.373(11) . ?

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
C18 N4 C3 119.6(6) . . ?
C18 N4 C5 119.4(7) . . ?
C3 N4 C5 117.2(6) . . ?
C3 O2 O1 109.3(5) . . ?
C8 O7 O6 113.7(4) . . ?
C5 O6 O7 108.8(5) . . ?
C8 O1 O2 114.8(4) . . ?
C19 C18 N4 121.4(7) . . ?
C19 C18 C23 117.0(7) . . ?
C23 C18 N4 121.6(7) . . ?
C14 C13 C8 115.6(5) . . ?
C12 C13 C8 110.1(5) . . ?
C12 C13 C14 115.0(6) . . ?
O7 C8 O1 108.9(5) . . ?
O7 C8 C13 104.7(5) . . ?
O7 C8 C9 113.7(5) . . ?
O1 C8 C13 103.8(5) . . ?
O1 C8 C9 112.6(5) . . ?
C9 C8 C13 112.4(5) . . ?
C18 C19 C20 121.1(8) . . ?
C16 C14 C13 116.0(7) . . ?
C16 C14 C15 107.4(7) . . ?
C15 C14 C13 111.5(6) . . ?
N4 C3 O2 114.2(6) . . ?
N4 C5 O6 114.6(6) . . ?
C8 C9 C10 112.1(5) . . ?
C11 C12 C13 112.1(7) . . ?
C21 C22 C23 122.7(9) . . ?
C11 C10 C9 108.5(6) . . ?
C17 C10 C9 109.4(7) . . ?
C17 C10 C11 113.3(7) . . ?
C22 C23 C18 120.4(8) . . ?
C12 C11 C10 112.2(7) . . ?
C19 C20 Cl1 119.4(7) . . ?
C21 C20 Cl1 118.9(7) . . ?
C21 C20 C19 121.7(8) . . ?
C22 C21 C20 117.1(9) . . ?

_olex2_date_sample_data_collection 2017-11-16
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hgm-727
_audit_block_doi                 10.5517/ccdc.csd.cc1pw7qj
_database_code_depnum_ccdc_archive 'CCDC 1575318'
_audit_update_record             
;
2017-09-20 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;
_audit_creation_date             2017-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H22 F N O4'
_chemical_formula_sum            'C16 H22 F N O4'
_chemical_formula_weight         311.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.6457(5)
_cell_length_b                   26.456(4)
_cell_length_c                   10.4560(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.112(8)
_cell_angle_gamma                90
_cell_volume                     1537.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1046
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.9290
_cell_measurement_theta_min      2.1720
_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  0.52894
_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            ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             664
_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  0.0218
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_Laue_measured_fraction_max 0.640
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4835
_diffrn_reflns_point_group_measured_fraction_max 0.640
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.204
_diffrn_reflns_theta_min         2.123
_diffrn_ambient_temperature      293(2)
_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  -23.00   23.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
  2 omega   11.00   46.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -       17.1042  -99.0000  120.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega  -49.00   14.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -       17.1042    0.0000 -180.0000 63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0058285000
_diffrn_orient_matrix_UB_12      0.0168381000
_diffrn_orient_matrix_UB_13      -0.0533378000
_diffrn_orient_matrix_UB_21      -0.0326604000
_diffrn_orient_matrix_UB_22      -0.0203285000
_diffrn_orient_matrix_UB_23      -0.0436254000
_diffrn_orient_matrix_UB_31      -0.1232357000
_diffrn_orient_matrix_UB_32      0.0046001000
_diffrn_orient_matrix_UB_33      0.0016705000
_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'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1592
_reflns_number_total             2664
_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         0.144
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.865
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         2664
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      0.865
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.004
_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          0.1251
_refine_ls_wR_factor_ref         0.1563
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.1581(3) 0.18310(8) 0.15164(15) 0.0478(5) Uani 1 1 d . . . . .
O2 O -0.1613(3) 0.14906(8) 0.23728(16) 0.0527(5) Uani 1 1 d . . . . .
O3 O 0.0198(3) 0.19491(9) 0.02428(15) 0.0582(6) Uani 1 1 d . . . . .
O4 O -0.1461(3) 0.19287(9) 0.32469(16) 0.0554(6) Uani 1 1 d . . . . .
N5 N -0.1822(3) 0.25441(10) 0.15114(17) 0.0457(6) Uani 1 1 d . . . . .
F6 F 0.4311(3) 0.41815(8) 0.24720(18) 0.0806(6) Uani 1 1 d . . . . .
C7 C 0.0711(4) 0.13918(12) 0.2074(2) 0.0429(7) Uani 1 1 d . . . . .
C8 C -0.0228(4) 0.29543(12) 0.17883(19) 0.0408(7) Uani 1 1 d . . . . .
C9 C -0.0599(4) 0.33302(13) 0.2666(2) 0.0470(7) Uani 1 1 d . . . . .
C10 C 0.3190(5) 0.34287(12) 0.1345(2) 0.0484(7) Uani 1 1 d . . . . .
C11 C 0.1692(4) 0.30175(13) 0.1129(2) 0.0458(7) Uani 1 1 d . . . . .
C12 C 0.2128(6) 0.08822(14) 0.4172(3) 0.0600(9) Uani 1 1 d . . . . .
C13 C 0.2786(4) 0.37819(13) 0.2230(2) 0.0531(8) Uani 1 1 d . . . . .
C14 C 0.2601(5) 0.13146(14) 0.3291(3) 0.0505(8) Uani 1 1 d . . . . .
C15 C 0.0916(5) 0.37385(14) 0.2893(3) 0.0537(8) Uani 1 1 d . . . . .
C16 C 0.2637(6) 0.07325(15) 0.0787(3) 0.0621(9) Uani 1 1 d . . . . .
C17 C 0.0310(5) 0.09548(14) 0.1133(3) 0.0535(8) Uani 1 1 d . . . . .
C18 C -0.1904(5) 0.22622(15) 0.0359(3) 0.0574(8) Uani 1 1 d . . . . .
C19 C -0.2884(5) 0.23139(14) 0.2518(3) 0.0571(8) Uani 1 1 d . . . . .
C20 C 0.2307(6) 0.03444(15) 0.3703(3) 0.0677(10) Uani 1 1 d . . . . .
C21 C 0.4296(6) 0.02374(18) 0.2920(3) 0.0702(10) Uani 1 1 d . . . . .
C22 C 0.3517(7) 0.02385(16) 0.1463(3) 0.0717(11) Uani 1 1 d . . . . .
H18A H -0.328(5) 0.2052(13) 0.024(2) 0.056(8) Uiso 1 1 d . . . . .
H14A H 0.415(4) 0.1275(11) 0.303(2) 0.046(7) Uiso 1 1 d . . . . .
H9 H -0.194(4) 0.3287(12) 0.313(2) 0.055(7) Uiso 1 1 d . . . . .
H11 H 0.195(4) 0.2771(12) 0.056(2) 0.046(7) Uiso 1 1 d . . . . .
H10 H 0.461(4) 0.3477(11) 0.090(2) 0.050(7) Uiso 1 1 d . . . . .
H15 H 0.062(4) 0.3989(13) 0.349(2) 0.054(8) Uiso 1 1 d . . . . .
H17A H -0.071(5) 0.1088(14) 0.037(3) 0.073(9) Uiso 1 1 d . . . . .
H19A H -0.437(6) 0.2193(14) 0.215(3) 0.075(9) Uiso 1 1 d . . . . .
H17B H -0.061(4) 0.0680(12) 0.151(2) 0.048(7) Uiso 1 1 d . . . . .
H18B H -0.198(4) 0.2506(13) -0.044(3) 0.067(8) Uiso 1 1 d . . . . .
H14B H 0.259(5) 0.1634(15) 0.377(3) 0.072(9) Uiso 1 1 d . . . . .
H16A H 0.392(5) 0.0992(14) 0.098(3) 0.070(9) Uiso 1 1 d . . . . .
H16B H 0.223(6) 0.0667(16) -0.014(3) 0.099(11) Uiso 1 1 d . . . . .
H19B H -0.302(5) 0.2554(16) 0.326(3) 0.088(10) Uiso 1 1 d . . . . .
H12A H 0.054(6) 0.0898(13) 0.439(3) 0.078(10) Uiso 1 1 d . . . . .
H20A H 0.066(6) 0.0216(16) 0.316(3) 0.093(11) Uiso 1 1 d . . . . .
H12B H 0.323(5) 0.0889(15) 0.499(3) 0.087(10) Uiso 1 1 d . . . . .
H20B H 0.246(5) 0.0118(15) 0.447(3) 0.084(9) Uiso 1 1 d . . . . .
H22A H 0.208(6) -0.0032(16) 0.125(3) 0.092(11) Uiso 1 1 d . . . . .
H22B H 0.483(6) 0.0137(15) 0.105(3) 0.095(11) Uiso 1 1 d . . . . .
H21A H 0.494(6) -0.0138(17) 0.320(3) 0.093(11) Uiso 1 1 d . . . . .
H21B H 0.560(6) 0.0496(18) 0.316(3) 0.086(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 O3 1.455(2) . ?
O1 C7 1.426(3) . ?
O2 O4 1.469(3) . ?
O2 C7 1.425(3) . ?
O3 C18 1.470(4) . ?
O4 C19 1.432(4) . ?
N5 C8 1.407(4) . ?
N5 C18 1.411(4) . ?
N5 C19 1.435(3) . ?
F6 C13 1.359(4) . ?
C7 C14 1.524(3) . ?
C7 C17 1.510(4) . ?
C8 C9 1.394(4) . ?
C8 C11 1.393(3) . ?
C9 C15 1.373(4) . ?
C10 C11 1.372(4) . ?
C10 C13 1.362(4) . ?
C12 C14 1.521(5) . ?
C12 C20 1.514(5) . ?
C13 C15 1.366(4) . ?
C16 C17 1.540(4) . ?
C16 C22 1.527(5) . ?
C20 C21 1.527(4) . ?
C21 C22 1.510(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 O3 112.44(17) . . ?
C7 O2 O4 108.99(16) . . ?
O1 O3 C18 110.90(16) . . ?
C19 O4 O2 105.3(2) . . ?
C8 N5 C18 120.5(2) . . ?
C8 N5 C19 120.7(2) . . ?
C18 N5 C19 116.5(3) . . ?
O1 C7 O2 109.7(2) . . ?
O1 C7 C14 102.1(2) . . ?
O1 C7 C17 112.4(2) . . ?
O2 C7 C14 112.24(19) . . ?
O2 C7 C17 104.15(18) . . ?
C17 C7 C14 116.4(3) . . ?
C9 C8 N5 121.4(2) . . ?
C9 C8 C11 117.4(3) . . ?
C11 C8 N5 121.1(2) . . ?
C15 C9 C8 121.0(2) . . ?
C13 C10 C11 118.9(2) . . ?
C10 C11 C8 121.6(3) . . ?
C20 C12 C14 118.8(2) . . ?
F6 C13 C10 118.9(2) . . ?
F6 C13 C15 119.4(3) . . ?
C15 C13 C10 121.6(3) . . ?
C7 C14 C12 115.8(2) . . ?
C13 C15 C9 119.5(3) . . ?
C22 C16 C17 116.1(3) . . ?
C7 C17 C16 114.2(2) . . ?
N5 C18 O3 117.6(2) . . ?
O4 C19 N5 115.2(2) . . ?
C12 C20 C21 116.4(3) . . ?
C22 C21 C20 115.4(3) . . ?
C21 C22 C16 118.8(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_kls-10-4
_audit_block_doi                 10.5517/ccdc.csd.cc1z62gq
_database_code_depnum_ccdc_archive 'CCDC 1823093'
_audit_update_record             
;
2018-02-09 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;
_audit_creation_date             2017-11-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H26 F N O4'
_chemical_formula_sum            'C18 H26 F N O4'
_chemical_formula_weight         339.40
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.8989(17)
_cell_length_b                   5.8609(5)
_cell_length_c                   13.5007(19)
_cell_angle_alpha                90
_cell_angle_beta                 116.417(17)
_cell_angle_gamma                90
_cell_volume                     914.1(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1175
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4750
_cell_measurement_theta_min      1.7670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79772
_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            colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             364.0
_exptl_crystal_size_max          0.71
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4719
_diffrn_reflns_point_group_measured_fraction_full 0.857
_diffrn_reflns_point_group_measured_fraction_max 0.702
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.124
_diffrn_reflns_theta_min         1.684
_diffrn_ambient_temperature      293(2)
_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   -8.00   88.00   1.0000    6.1350
omega____ theta____ kappa____ phi______ frames
    -       16.9480   19.0000  -30.0000 96

#__ type_ start__ end____ width___ exp.time_
  2 omega    2.00   83.00   1.0000    6.1350
omega____ theta____ kappa____ phi______ frames
    -       16.9480   57.0000   30.0000 81

#__ type_ start__ end____ width___ exp.time_
  3 omega  -20.00    7.00   1.0000    6.1350
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -89.00  -64.00   1.0000    6.1350
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      0.0566188000
_diffrn_orient_matrix_UB_12      -0.0172977000
_diffrn_orient_matrix_UB_13      0.0050638000
_diffrn_orient_matrix_UB_21      -0.0227092000
_diffrn_orient_matrix_UB_22      -0.0078031000
_diffrn_orient_matrix_UB_23      -0.0583004000
_diffrn_orient_matrix_UB_31      0.0066719000
_diffrn_orient_matrix_UB_32      0.1195454000
_diffrn_orient_matrix_UB_33      -0.0030563000
_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'
_reflns_Friedel_coverage         0.473
_reflns_Friedel_fraction_full    0.680
_reflns_Friedel_fraction_max     0.498
_reflns_number_gt                2353
_reflns_number_total             3445
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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         0.267
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.112
_refine_ls_abs_structure_details 
;
 Flack x determined using 669 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.0(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3445
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0653
_refine_ls_restrained_S_all      1.162
_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)+(0.0956P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.2054
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C13(H13), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C9(H9A,H9B), C3(H3A,H3B), C12(H12A,H12B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C23(H23), C22(H22)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C16(H16A,H16B,H16C)
;
_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
O1 O 0.6580(3) 0.0316(5) 0.2578(3) 0.0498(8) Uani 1 1 d . . . . .
O7 O 0.5507(2) 0.3381(6) 0.1512(3) 0.0543(9) Uani 1 1 d . . . . .
O2 O 0.7706(3) 0.0074(6) 0.2561(3) 0.0581(9) Uani 1 1 d . . . . .
C8 C 0.6265(4) 0.2624(7) 0.2611(4) 0.0437(10) Uani 1 1 d . . . . .
O6 O 0.6125(3) 0.4445(6) 0.0954(3) 0.0628(10) Uani 1 1 d . . . . .
N4 N 0.7423(4) 0.1667(8) 0.0802(3) 0.0622(12) Uani 1 1 d . . . . .
C5 C 0.6320(4) 0.2757(12) 0.0283(4) 0.0707(17) Uani 1 1 d . . . . .
H5A H 0.5722 0.1602 0.0079 0.085 Uiso 1 1 calc R . . . .
H5B H 0.6243 0.3479 -0.0393 0.085 Uiso 1 1 calc R . . . .
C14 C 0.4312(5) 0.1259(10) 0.2568(5) 0.0630(14) Uani 1 1 d . . . . .
H14 H 0.4046 0.1547 0.1777 0.076 Uiso 1 1 calc R . . . .
C18 C 0.8432(4) 0.3016(9) 0.1076(4) 0.0513(11) Uani 1 1 d . . . . .
C13 C 0.5463(4) 0.2564(9) 0.3187(4) 0.0544(12) Uani 1 1 d . . . . .
H13 H 0.5240 0.4155 0.3208 0.065 Uiso 1 1 calc R . . . .
C10 C 0.7981(5) 0.3593(12) 0.4405(5) 0.082(2) Uani 1 1 d . . . . .
H10 H 0.8315 0.2073 0.4449 0.099 Uiso 1 1 calc R . . . .
C9 C 0.7292(4) 0.4200(8) 0.3200(4) 0.0581(13) Uani 1 1 d . . . . .
H9A H 0.7793 0.4118 0.2837 0.070 Uiso 1 1 calc R . . . .
H9B H 0.7018 0.5758 0.3141 0.070 Uiso 1 1 calc R . . . .
C3 C 0.7508(5) -0.0336(9) 0.1441(5) 0.0687(15) Uani 1 1 d . . . . .
H3A H 0.8134 -0.1274 0.1456 0.082 Uiso 1 1 calc R . . . .
H3B H 0.6797 -0.1203 0.1070 0.082 Uiso 1 1 calc R . . . .
C19 C 0.8475(4) 0.4632(11) 0.0350(4) 0.0654(14) Uani 1 1 d . . . . .
H19 H 0.7832 0.4838 -0.0328 0.078 Uiso 1 1 calc R . . . .
C15 C 0.4394(6) -0.1308(10) 0.2723(6) 0.0767(17) Uani 1 1 d . . . . .
H15A H 0.4861 -0.1929 0.2400 0.115 Uiso 1 1 calc GR . . . .
H15B H 0.3632 -0.1960 0.2369 0.115 Uiso 1 1 calc GR . . . .
H15C H 0.4740 -0.1659 0.3498 0.115 Uiso 1 1 calc GR . . . .
F1 F 1.1322(3) 0.6987(8) 0.1834(4) 0.1162(17) Uani 1 1 d . . . . .
C21 C 1.0371(4) 0.5661(11) 0.1573(5) 0.0713(16) Uani 1 1 d . . . . .
C20 C 0.9440(5) 0.5937(10) 0.0604(5) 0.0700(16) Uani 1 1 d . . . . .
H20 H 0.9448 0.7014 0.0101 0.084 Uiso 1 1 calc R . . . .
C23 C 0.9419(4) 0.2810(12) 0.2074(5) 0.0814(19) Uani 1 1 d . . . . .
H23 H 0.9420 0.1783 0.2599 0.098 Uiso 1 1 calc R . . . .
C12 C 0.6175(6) 0.1879(12) 0.4398(5) 0.0823(19) Uani 1 1 d . . . . .
H12A H 0.5687 0.1912 0.4775 0.099 Uiso 1 1 calc R . . . .
H12B H 0.6460 0.0334 0.4436 0.099 Uiso 1 1 calc R . . . .
C22 C 1.0395(5) 0.4078(15) 0.2307(6) 0.092(2) Uani 1 1 d . . . . .
H22 H 1.1063 0.3849 0.2963 0.110 Uiso 1 1 calc R . . . .
C17 C 0.8978(7) 0.5300(18) 0.4936(7) 0.149(4) Uani 1 1 d . . . . .
H17A H 0.9437 0.5290 0.4539 0.224 Uiso 1 1 calc GR . . . .
H17B H 0.9451 0.4877 0.5692 0.224 Uiso 1 1 calc GR . . . .
H17C H 0.8669 0.6801 0.4909 0.224 Uiso 1 1 calc GR . . . .
C16 C 0.3391(6) 0.2242(13) 0.2872(8) 0.109(3) Uani 1 1 d . . . . .
H16A H 0.3662 0.2160 0.3658 0.163 Uiso 1 1 calc GR . . . .
H16B H 0.2689 0.1378 0.2510 0.163 Uiso 1 1 calc GR . . . .
H16C H 0.3245 0.3805 0.2638 0.163 Uiso 1 1 calc GR . . . .
C11 C 0.7191(7) 0.3498(17) 0.4970(5) 0.106(3) Uani 1 1 d . . . . .
H11A H 0.6898 0.5017 0.4981 0.127 Uiso 1 1 calc R . . . .
H11B H 0.7638 0.3012 0.5731 0.127 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 O2 1.470(4) . ?
O1 C8 1.419(5) . ?
O7 C8 1.437(5) . ?
O7 O6 1.458(4) . ?
O2 C3 1.437(6) . ?
C8 C13 1.547(6) . ?
C8 C9 1.518(6) . ?
O6 C5 1.437(7) . ?
N4 C5 1.427(7) . ?
N4 C18 1.425(6) . ?
N4 C3 1.432(7) . ?
C14 C13 1.544(8) . ?
C14 C15 1.516(8) . ?
C14 C16 1.531(8) . ?
C18 C19 1.382(7) . ?
C18 C23 1.387(7) . ?
C13 C12 1.530(8) . ?
C10 C9 1.509(8) . ?
C10 C17 1.532(10) . ?
C10 C11 1.521(10) . ?
C19 C20 1.369(7) . ?
F1 C21 1.360(6) . ?
C21 C20 1.335(8) . ?
C21 C22 1.348(9) . ?
C23 C22 1.372(8) . ?
C12 C11 1.522(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 O2 113.1(3) . . ?
C8 O7 O6 112.9(3) . . ?
C3 O2 O1 108.5(3) . . ?
O1 C8 O7 109.6(3) . . ?
O1 C8 C13 105.0(3) . . ?
O1 C8 C9 113.6(4) . . ?
O7 C8 C13 103.1(3) . . ?
O7 C8 C9 112.8(4) . . ?
C9 C8 C13 112.0(4) . . ?
C5 O6 O7 108.7(4) . . ?
C5 N4 C3 117.1(4) . . ?
C18 N4 C5 118.4(5) . . ?
C18 N4 C3 118.9(4) . . ?
N4 C5 O6 114.5(4) . . ?
C15 C14 C13 115.2(5) . . ?
C15 C14 C16 110.6(5) . . ?
C16 C14 C13 110.0(5) . . ?
C19 C18 N4 121.1(4) . . ?
C19 C18 C23 116.1(4) . . ?
C23 C18 N4 122.8(4) . . ?
C14 C13 C8 115.9(4) . . ?
C12 C13 C8 109.0(4) . . ?
C12 C13 C14 115.1(5) . . ?
C9 C10 C17 108.6(7) . . ?
C9 C10 C11 110.2(5) . . ?
C11 C10 C17 113.5(7) . . ?
C10 C9 C8 112.3(5) . . ?
N4 C3 O2 115.3(4) . . ?
C20 C19 C18 121.6(5) . . ?
C20 C21 F1 119.9(5) . . ?
C20 C21 C22 121.4(5) . . ?
C22 C21 F1 118.7(5) . . ?
C21 C20 C19 119.9(5) . . ?
C22 C23 C18 121.8(5) . . ?
C11 C12 C13 110.5(6) . . ?
C21 C22 C23 119.0(6) . . ?
C10 C11 C12 112.7(5) . . ?

_olex2_date_sample_data_collection 2017-10-10
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_hgm-50-1
_audit_block_doi                 10.5517/ccdc.csd.cc1ndsd7
_database_code_depnum_ccdc_archive 'CCDC 1531629'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tet.2018.01.045 2018
_audit_update_record             
;
2017-02-08 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;
_audit_creation_date             2017-01-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H25 N O5'
_chemical_formula_sum            'C19 H25 N O5'
_chemical_formula_weight         347.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_cell_length_a                   12.4037(10)
_cell_length_b                   14.5530(17)
_cell_length_c                   9.9903(8)
_cell_angle_alpha                90.0
_cell_angle_beta                 103.023(8)
_cell_angle_gamma                90.0
_cell_volume                     1757.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2178
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.9850
_cell_measurement_theta_min      2.2040
_cell_oxdiff_angle_alpha         89.938(7)
_cell_oxdiff_angle_beta          102.972(5)
_cell_oxdiff_angle_gamma         89.921(7)
_cell_oxdiff_length_a            12.4078(9)
_cell_oxdiff_length_b            14.5506(17)
_cell_oxdiff_length_c            9.9866(6)
_cell_oxdiff_measurement_reflns_used 2178
_cell_oxdiff_volume              1757.0(3)
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36802
_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            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plank
_exptl_crystal_F_000             744.0
_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  0.0413
_diffrn_reflns_av_unetI/netI     0.0547
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.841
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8787
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.841
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.300
_diffrn_reflns_theta_min         1.685
_diffrn_ambient_temperature      293(2)
_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  -35.00   84.00   1.0000    2.7400
omega____ theta____ kappa____ phi______ frames
    -       17.1042    0.0000 -120.0000 119

#__ type_ start__ end____ width___ exp.time_
  2 omega   12.00   56.00   1.0000    2.7400
omega____ theta____ kappa____ phi______ frames
    -       17.1042  -99.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega  -12.00   18.00   1.0000    2.7400
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
  4 omega   -4.00   23.00   1.0000    2.7400
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -87.00  -62.00   1.0000    2.7400
omega____ theta____ kappa____ phi______ frames
    -      -16.2449 -178.0000  -30.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0182546000
_diffrn_orient_matrix_UB_12      0.0203480000
_diffrn_orient_matrix_UB_13      -0.0657807000
_diffrn_orient_matrix_UB_21      -0.0074627000
_diffrn_orient_matrix_UB_22      -0.0442923000
_diffrn_orient_matrix_UB_23      -0.0302305000
_diffrn_orient_matrix_UB_31      -0.0552485000
_diffrn_orient_matrix_UB_32      -0.0006546000
_diffrn_orient_matrix_UB_33      0.0084457000
_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'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2339
_reflns_number_total             4041
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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         0.435
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.144
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         4041
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1237
_refine_ls_R_factor_gt           0.0766
_refine_ls_restrained_S_all      1.144
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.007
_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          0.1906
_refine_ls_wR_factor_ref         0.2253
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.60808(13) 0.03472(14) 0.18661(18) 0.0485(5) Uani 1 1 d . . . . .
O2 O 0.60638(14) -0.05412(13) 0.25522(19) 0.0492(5) Uani 1 1 d . . . . .
O3 O 0.78220(14) 0.07054(15) 0.31931(19) 0.0524(6) Uani 1 1 d . . . . .
O4 O 0.71987(18) 0.12809(15) 0.3925(2) 0.0628(6) Uani 1 1 d . . . . .
O5 O 0.61213(17) -0.14683(14) 0.6470(2) 0.0642(6) Uani 1 1 d . . . . .
C6 C 0.7794(2) -0.0129(2) 0.1205(3) 0.0492(7) Uani 1 1 d . . . . .
C7 C 0.71731(18) 0.05934(18) 0.1831(2) 0.0385(6) Uani 1 1 d . . . . .
N8 N 0.67584(19) -0.01548(16) 0.4934(2) 0.0494(6) Uani 1 1 d . . . . .
C9 C 0.8848(2) 0.1106(2) 0.0343(3) 0.0542(8) Uani 1 1 d . . . . .
C10 C 0.8951(2) 0.0226(2) 0.1180(3) 0.0551(8) Uani 1 1 d . . . . .
C11 C 0.7069(2) 0.1470(2) 0.0993(3) 0.0497(7) Uani 1 1 d . . . . .
C12 C 0.7500(2) -0.0884(2) 0.5443(3) 0.0486(7) Uani 1 1 d . . . . .
C13 C 0.7160(2) -0.1565(2) 0.6246(3) 0.0528(7) Uani 1 1 d . . . . .
C14 C 0.5821(2) -0.0362(2) 0.3871(3) 0.0479(7) Uani 1 1 d . . . . .
C15 C 0.8233(3) 0.1818(2) 0.0991(4) 0.0553(8) Uani 1 1 d . . . . .
C16 C 0.8553(3) -0.0937(3) 0.5207(3) 0.0634(9) Uani 1 1 d . . . . .
C17 C 0.7116(3) 0.0771(2) 0.5143(3) 0.0602(9) Uani 1 1 d . . . . .
C18 C 0.7157(3) -0.0316(3) -0.0252(3) 0.0687(10) Uani 1 1 d . . . . .
C19 C 0.8220(3) 0.0903(4) -0.1118(3) 0.0719(11) Uani 1 1 d . . . . .
C20 C 0.5761(4) -0.2116(3) 0.7340(5) 0.0753(11) Uani 1 1 d . . . . .
C21 C 0.7081(3) 0.0547(3) -0.1097(3) 0.0739(11) Uani 1 1 d . . . . .
C22 C 0.6450(3) 0.1264(3) -0.0478(4) 0.0705(10) Uani 1 1 d . . . . .
C23 C 0.7870(3) -0.2273(3) 0.6782(4) 0.0706(10) Uani 1 1 d . . . . .
C24 C 0.9256(3) -0.1648(3) 0.5746(4) 0.0810(12) Uani 1 1 d . . . . .
C25 C 0.8905(3) -0.2301(3) 0.6523(5) 0.0826(12) Uani 1 1 d . . . . .
H6 H 0.7859(19) -0.0656(19) 0.173(3) 0.039(7) Uiso 1 1 d . . . . .
H11 H 0.671(2) 0.192(2) 0.141(3) 0.053(8) Uiso 1 1 d . . . . .
H14A H 0.552(2) -0.101(2) 0.408(3) 0.048(7) Uiso 1 1 d . . . . .
H14B H 0.535(2) 0.012(2) 0.382(3) 0.058(9) Uiso 1 1 d . . . . .
H19A H 0.814(2) 0.151(3) -0.166(4) 0.070(10) Uiso 1 1 d . . . . .
H18A H 0.640(2) -0.0559(17) -0.027(2) 0.035(6) Uiso 1 1 d . . . . .
H15A H 0.817(2) 0.236(2) 0.044(3) 0.067(9) Uiso 1 1 d . . . . .
H10A H 0.946(2) 0.0380(19) 0.215(3) 0.049(7) Uiso 1 1 d . . . . .
H16 H 0.876(3) -0.044(2) 0.475(4) 0.070(10) Uiso 1 1 d . . . . .
H17A H 0.787(2) 0.082(2) 0.580(3) 0.054(8) Uiso 1 1 d . . . . .
H22A H 0.568(3) 0.105(2) -0.051(3) 0.060(8) Uiso 1 1 d . . . . .
H15B H 0.863(3) 0.197(2) 0.190(4) 0.069(10) Uiso 1 1 d . . . . .
H22B H 0.643(2) 0.187(2) -0.088(3) 0.069(10) Uiso 1 1 d . . . . .
H18B H 0.754(3) -0.084(3) -0.062(4) 0.096(12) Uiso 1 1 d . . . . .
H19B H 0.860(3) 0.047(3) -0.163(4) 0.093(12) Uiso 1 1 d . . . . .
H17B H 0.662(3) 0.113(3) 0.545(4) 0.093(13) Uiso 1 1 d . . . . .
H23 H 0.760(2) -0.272(2) 0.737(3) 0.063(9) Uiso 1 1 d . . . . .
H9 H 0.958(2) 0.138(2) 0.044(3) 0.057(8) Uiso 1 1 d . . . . .
H10B H 0.938(2) -0.029(2) 0.083(3) 0.059(8) Uiso 1 1 d . . . . .
H20A H 0.570(3) -0.269(3) 0.694(4) 0.084(12) Uiso 1 1 d . . . . .
H25 H 0.937(3) -0.279(3) 0.688(4) 0.087(12) Uiso 1 1 d . . . . .
H21 H 0.656(3) 0.039(3) -0.203(4) 0.087(11) Uiso 1 1 d . . . . .
H24 H 0.994(3) -0.167(3) 0.551(4) 0.099(13) Uiso 1 1 d . . . . .
H20B H 0.637(4) -0.215(3) 0.819(5) 0.110(15) Uiso 1 1 d . . . . .
H20C H 0.505(3) -0.192(3) 0.742(4) 0.091(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 O2 1.466(3) . ?
O1 C7 1.409(3) . ?
O2 C14 1.440(3) . ?
O3 O4 1.445(3) . ?
O3 C7 1.425(3) . ?
O4 C17 1.448(4) . ?
O5 C13 1.364(3) . ?
O5 C20 1.421(4) . ?
C6 C7 1.519(4) . ?
C6 C10 1.530(4) . ?
C6 C18 1.517(4) . ?
C7 C11 1.516(4) . ?
N8 C12 1.421(4) . ?
N8 C14 1.419(4) . ?
N8 C17 1.420(4) . ?
C9 C10 1.519(4) . ?
C9 C15 1.515(4) . ?
C9 C19 1.521(4) . ?
C11 C15 1.530(4) . ?
C11 C22 1.526(5) . ?
C12 C13 1.398(4) . ?
C12 C16 1.381(4) . ?
C13 C23 1.383(5) . ?
C16 C24 1.381(5) . ?
C18 C21 1.504(6) . ?
C19 C21 1.510(5) . ?
C21 C22 1.518(6) . ?
C23 C25 1.367(5) . ?
C24 C25 1.358(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
C7 O1 O2 110.55(17) . . ?
C14 O2 O1 107.2(2) . . ?
C7 O3 O4 107.32(17) . . ?
O3 O4 C17 106.0(2) . . ?
C13 O5 C20 118.1(3) . . ?
C7 C6 C10 109.7(3) . . ?
C7 C6 C18 108.5(3) . . ?
C18 C6 C10 109.4(3) . . ?
O1 C7 O3 110.16(19) . . ?
O1 C7 C6 114.4(2) . . ?
O1 C7 C11 105.4(2) . . ?
O3 C7 C6 104.0(2) . . ?
O3 C7 C11 113.0(2) . . ?
C6 C7 C11 110.0(2) . . ?
C14 N8 C12 117.6(2) . . ?
C17 N8 C12 120.0(3) . . ?
C17 N8 C14 119.2(3) . . ?
C10 C9 C19 109.0(3) . . ?
C15 C9 C10 109.2(2) . . ?
C15 C9 C19 110.1(3) . . ?
C9 C10 C6 109.3(2) . . ?
C7 C11 C22 109.1(3) . . ?
C15 C11 C7 108.4(2) . . ?
C15 C11 C22 109.5(3) . . ?
C13 C12 N8 118.7(2) . . ?
C16 C12 N8 122.8(3) . . ?
C16 C12 C13 118.5(3) . . ?
O5 C13 C12 116.1(3) . . ?
O5 C13 C23 123.8(3) . . ?
C23 C13 C12 120.2(3) . . ?
N8 C14 O2 114.7(2) . . ?
C9 C15 C11 109.9(3) . . ?
C12 C16 C24 120.9(4) . . ?
N8 C17 O4 116.2(3) . . ?
C21 C18 C6 110.0(3) . . ?
C21 C19 C9 109.4(3) . . ?
C18 C21 C19 110.7(3) . . ?
C18 C21 C22 108.6(3) . . ?
C19 C21 C22 109.8(4) . . ?
C21 C22 C11 109.5(3) . . ?
C25 C23 C13 119.5(4) . . ?
C25 C24 C16 119.5(4) . . ?
C24 C25 C23 121.5(4) . . ?

_olex2_date_sample_data_collection 2017-01-10
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zdf-38-298
_audit_block_doi                 10.5517/ccdc.csd.cc1pt52r
_database_code_depnum_ccdc_archive 'CCDC 1573314'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.tet.2018.01.045 2018
_audit_update_record             
;
2017-09-08 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;
_audit_creation_date             2017-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H22 Cl N O4'
_chemical_formula_sum            'C18 H22 Cl N O4'
_chemical_formula_weight         351.82
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   20.184(4)
_cell_length_b                   6.6789(7)
_cell_length_c                   12.7848(16)
_cell_angle_alpha                90
_cell_angle_beta                 104.567(16)
_cell_angle_gamma                90
_cell_volume                     1668.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1091
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.2350
_cell_measurement_theta_min      3.1220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13705
_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            ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             744.0
_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  0.0543
_diffrn_reflns_av_unetI/netI     0.1296
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7580
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.144
_diffrn_reflns_theta_min         3.128
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0854
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -19.00   23.00   1.0000   16.6950
omega____ theta____ kappa____ phi______ frames
    -      -16.4011  -99.0000 -180.0000 42

#__ type_ start__ end____ width___ exp.time_
  2 omega    4.00   84.00   1.0000   16.6950
omega____ theta____ kappa____ phi______ frames
    -       17.0261   57.0000  -60.0000 80

#__ type_ start__ end____ width___ exp.time_
  3 omega   -2.00   87.00   1.0000   16.6950
omega____ theta____ kappa____ phi______ frames
    -       17.0261   19.0000 -120.0000 89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0159655000
_diffrn_orient_matrix_UB_12      -0.0104056000
_diffrn_orient_matrix_UB_13      0.0432361000
_diffrn_orient_matrix_UB_21      0.0314486000
_diffrn_orient_matrix_UB_22      0.0219077000
_diffrn_orient_matrix_UB_23      0.0375682000
_diffrn_orient_matrix_UB_31      -0.0083257000
_diffrn_orient_matrix_UB_32      0.1034476000
_diffrn_orient_matrix_UB_33      -0.0036385000
_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'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1678
_reflns_number_total             3891
_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         0.249
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3891
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2158
_refine_ls_R_factor_gt           0.0916
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.006
_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          0.1804
_refine_ls_wR_factor_ref         0.2488
_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:
 C007(H007), C010(H010), C016(H016), C024(H024)
2.b Secondary CH2 refined with riding coordinates:
 C014(H01A,H01B), C017(H01C,H01D), C018(H01E,H01F), C020(H02A,H02B), C021(H02C,
 H02D), C022(H02E,H02F), C023(H02G,H02H)
2.c Aromatic/amide H refined with riding coordinates:
 C012(H012), C013(H013), C015(H015), C019(H019)
;
_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
Cl00 Cl 0.46185(9) 0.9549(2) 0.18287(11) 0.0774(6) Uani 1 1 d . . . . .
O002 O 0.18958(17) 1.7065(4) -0.1552(2) 0.0502(9) Uani 1 1 d . . . . .
O003 O 0.26880(18) 1.5009(4) -0.2083(2) 0.0513(9) Uani 1 1 d . . . . .
O004 O 0.21927(19) 1.6718(5) -0.0394(2) 0.0523(9) Uani 1 1 d . . . . .
N005 N 0.3382(2) 1.6950(5) -0.0414(3) 0.0439(10) Uani 1 1 d . . . . .
C006 C 0.1978(2) 1.5365(6) -0.2167(3) 0.0362(11) Uani 1 1 d . . . . .
C007 C 0.1578(3) 1.5865(6) -0.3321(3) 0.0476(13) Uani 1 1 d . . . . .
H007 H 0.1749 1.7117 -0.3555 0.057 Uiso 1 1 calc R . . . .
C008 C 0.3649(2) 1.5141(6) 0.0077(3) 0.0384(11) Uani 1 1 d . . . . .
O009 O 0.2989(2) 1.6850(6) -0.2358(2) 0.0717(12) Uani 1 1 d . . . . .
C010 C 0.1720(3) 1.3419(6) -0.1800(3) 0.0470(13) Uani 1 1 d . . . . .
H010 H 0.1977 1.3106 -0.1060 0.056 Uiso 1 1 calc R . . . .
C011 C 0.4231(3) 1.1666(6) 0.1137(4) 0.0458(12) Uani 1 1 d . . . . .
C012 C 0.3727(3) 1.2633(7) 0.1471(4) 0.0569(14) Uani 1 1 d . . . . .
H012 H 0.3581 1.2137 0.2054 0.068 Uiso 1 1 calc R . . . .
C013 C 0.4143(3) 1.4067(7) -0.0255(4) 0.0576(14) Uani 1 1 d . . . . .
H013 H 0.4285 1.4507 -0.0855 0.069 Uiso 1 1 calc R . . . .
C014 C 0.1805(3) 1.1737(6) -0.2561(4) 0.0603(15) Uani 1 1 d . . . . .
H01A H 0.2287 1.1567 -0.2531 0.072 Uiso 1 1 calc R . . . .
H01B H 0.1638 1.0493 -0.2331 0.072 Uiso 1 1 calc R . . . .
C015 C 0.3433(3) 1.4346(7) 0.0951(4) 0.0556(14) Uani 1 1 d . . . . .
H015 H 0.3086 1.4983 0.1184 0.067 Uiso 1 1 calc R . . . .
C016 C 0.1413(3) 1.2205(7) -0.3713(4) 0.0563(14) Uani 1 1 d . . . . .
H016 H 0.1474 1.1115 -0.4194 0.068 Uiso 1 1 calc R . . . .
C017 C 0.1679(3) 1.4134(7) -0.4066(3) 0.0527(13) Uani 1 1 d . . . . .
H01C H 0.1436 1.4431 -0.4806 0.063 Uiso 1 1 calc R . . . .
H01D H 0.2161 1.3995 -0.4039 0.063 Uiso 1 1 calc R . . . .
C018 C 0.3487(3) 1.7558(7) -0.1429(4) 0.0535(13) Uani 1 1 d . . . . .
H01E H 0.3935 1.7094 -0.1473 0.064 Uiso 1 1 calc R . . . .
H01F H 0.3493 1.9009 -0.1451 0.064 Uiso 1 1 calc R . . . .
C019 C 0.4434(3) 1.2363(7) 0.0273(4) 0.0616(15) Uani 1 1 d . . . . .
H019 H 0.4771 1.1687 0.0035 0.074 Uiso 1 1 calc R . . . .
C020 C 0.0828(3) 1.6072(8) -0.3360(4) 0.0675(16) Uani 1 1 d . . . . .
H02A H 0.0574 1.6403 -0.4089 0.081 Uiso 1 1 calc R . . . .
H02B H 0.0765 1.7151 -0.2885 0.081 Uiso 1 1 calc R . . . .
C021 C 0.0961(3) 1.3674(9) -0.1846(4) 0.0691(16) Uani 1 1 d . . . . .
H02C H 0.0903 1.4771 -0.1379 0.083 Uiso 1 1 calc R . . . .
H02D H 0.0789 1.2464 -0.1587 0.083 Uiso 1 1 calc R . . . .
C022 C 0.2823(3) 1.7858(7) -0.0108(4) 0.0575(15) Uani 1 1 d . . . . .
H02E H 0.2740 1.9164 -0.0447 0.069 Uiso 1 1 calc R . . . .
H02F H 0.2949 1.8061 0.0668 0.069 Uiso 1 1 calc R . . . .
C023 C 0.0658(3) 1.2428(8) -0.3745(5) 0.0741(18) Uani 1 1 d . . . . .
H02G H 0.0400 1.2715 -0.4479 0.089 Uiso 1 1 calc R . . . .
H02H H 0.0488 1.1182 -0.3522 0.089 Uiso 1 1 calc R . . . .
C024 C 0.0553(3) 1.4104(9) -0.3004(5) 0.0742(17) Uani 1 1 d . . . . .
H024 H 0.0065 1.4240 -0.3031 0.089 Uiso 1 1 calc R . . . .


_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
Cl00 C011 1.746(5) . ?
O002 O004 1.469(4) . ?
O002 C006 1.414(5) . ?
O003 C006 1.429(5) . ?
O003 O009 1.453(4) . ?
O004 C022 1.448(6) . ?
N005 C008 1.405(5) . ?
N005 C018 1.425(5) . ?
N005 C022 1.421(6) . ?
C006 C007 1.530(6) . ?
C006 C010 1.517(6) . ?
C007 C017 1.544(6) . ?
C007 C020 1.508(7) . ?
C008 C013 1.380(6) . ?
C008 C015 1.402(6) . ?
O009 C018 1.430(5) . ?
C010 C014 1.524(6) . ?
C010 C021 1.529(7) . ?
C011 C012 1.360(6) . ?
C011 C019 1.354(6) . ?
C012 C015 1.380(6) . ?
C013 C019 1.377(7) . ?
C014 C016 1.519(6) . ?
C016 C017 1.507(6) . ?
C016 C023 1.523(7) . ?
C020 C024 1.540(7) . ?
C021 C024 1.530(7) . ?
C023 C024 1.515(7) . ?

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
C006 O002 O004 111.0(3) . . ?
C006 O003 O009 108.3(3) . . ?
C022 O004 O002 106.3(3) . . ?
C008 N005 C018 121.6(4) . . ?
C008 N005 C022 119.1(4) . . ?
C018 N005 C022 116.1(4) . . ?
O002 C006 O003 110.4(3) . . ?
O002 C006 C007 104.7(3) . . ?
O002 C006 C010 114.8(4) . . ?
O003 C006 C007 112.6(4) . . ?
O003 C006 C010 104.5(3) . . ?
C010 C006 C007 110.2(4) . . ?
C006 C007 C017 108.2(4) . . ?
C020 C007 C006 109.5(4) . . ?
C020 C007 C017 109.6(4) . . ?
C013 C008 N005 122.4(4) . . ?
C013 C008 C015 116.2(4) . . ?
C015 C008 N005 121.4(4) . . ?
C018 O009 O003 109.2(3) . . ?
C006 C010 C014 109.4(4) . . ?
C006 C010 C021 108.1(4) . . ?
C014 C010 C021 109.3(4) . . ?
C012 C011 Cl00 120.0(4) . . ?
C019 C011 Cl00 120.2(4) . . ?
C019 C011 C012 119.8(4) . . ?
C011 C012 C015 120.5(4) . . ?
C008 C013 C019 122.0(4) . . ?
C016 C014 C010 110.6(4) . . ?
C012 C015 C008 121.1(5) . . ?
C014 C016 C023 108.7(4) . . ?
C017 C016 C014 109.2(4) . . ?
C017 C016 C023 109.7(4) . . ?
C016 C017 C007 110.1(4) . . ?
N005 C018 O009 115.3(4) . . ?
C011 C019 C013 120.4(5) . . ?
C007 C020 C024 110.2(4) . . ?
C010 C021 C024 110.4(4) . . ?
N005 C022 O004 114.5(4) . . ?
C024 C023 C016 110.6(4) . . ?
C021 C024 C020 107.4(4) . . ?
C023 C024 C020 109.2(5) . . ?
C023 C024 C021 110.0(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_iir-248-5
_audit_block_doi                 10.5517/ccdc.csd.cc1zggkg
_database_code_depnum_ccdc_archive 'CCDC 1831156'
_audit_update_record             
;
2018-03-20 deposited with the CCDC.
2018-05-30 downloaded from the CCDC.
;
_audit_creation_date             2017-09-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-4
_chemical_name_systematic        
6'-phenylspiro[adamantane-2,2'-[1,3,4,8,6]tetraoxazocane]
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H23 N O4'
_chemical_formula_sum            'C18 H23 N O4'
_chemical_formula_weight         317.37
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_chemical_absolute_configuration ?
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'
_chemical_melting_point          ?
_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.
;

_cell_length_a                   12.735(3)
_cell_length_b                   6.5866(9)
_cell_length_c                   18.883(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1583.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1550
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.6380
_cell_measurement_theta_min      3.1800
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79315
_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    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             680.0
_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  0.0358
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4570
_diffrn_reflns_point_group_measured_fraction_max 0.552
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.164
_diffrn_reflns_theta_min         2.157
_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   -9.00   19.00   1.0000    5.0700
omega____ theta____ kappa____ phi______ frames
    -      -16.2449  -99.0000 -150.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00   66.00   1.0000    5.0700
omega____ theta____ kappa____ phi______ frames
    -       16.9480    0.0000  -30.0000 111
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0147949000
_diffrn_orient_matrix_UB_12      -0.0345680000
_diffrn_orient_matrix_UB_13      0.0341843000
_diffrn_orient_matrix_UB_21      0.0536039000
_diffrn_orient_matrix_UB_22      -0.0110380000
_diffrn_orient_matrix_UB_23      0.0093176000
_diffrn_orient_matrix_UB_31      0.0007421000
_diffrn_orient_matrix_UB_32      0.1013166000
_diffrn_orient_matrix_UB_33      0.0127211000
_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 Gemini Eos'
_reflns_Friedel_coverage         0.246
_reflns_Friedel_fraction_full    0.312
_reflns_Friedel_fraction_max     0.224
_reflns_number_gt                1856
_reflns_number_total             2359
_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         0.157
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 377 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         2359
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      0.945
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.001
_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          0.1276
_refine_ls_wR_factor_ref         0.1483
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O1 O 0.5878(2) 0.2970(4) 0.13387(16) 0.0403(7) Uani 1 1 d . . . . .
O2 O 0.6768(2) 0.5016(4) 0.21408(15) 0.0392(7) Uani 1 1 d . . . . .
C3 C 0.6964(4) 0.8300(5) 0.1206(3) 0.0466(10) Uani 1 1 d . . . . .
O4 O 0.4863(2) 0.3397(4) 0.16647(18) 0.0455(7) Uani 1 1 d . . . . .
N5 N 0.5332(3) 0.3221(5) 0.2905(2) 0.0453(8) Uani 1 1 d . . . . .
C6 C 0.6124(3) 0.6635(5) 0.1131(2) 0.0377(9) Uani 1 1 d . . . . .
C7 C 0.6562(3) 0.4640(5) 0.1411(2) 0.0318(8) Uani 1 1 d . . . . .
C8 C 0.8370(3) 0.5707(6) 0.1087(3) 0.0429(9) Uani 1 1 d . . . . .
C9 C 0.7541(3) 0.4028(6) 0.0997(2) 0.0378(9) Uani 1 1 d . . . . .
O10 O 0.7118(2) 0.3114(5) 0.24619(17) 0.0524(8) Uani 1 1 d . . . . .
C11 C 0.4958(3) 0.5089(6) 0.3163(2) 0.0404(9) Uani 1 1 d . . . . .
C12 C 0.5853(4) 0.6365(8) 0.0341(3) 0.0517(11) Uani 1 1 d . . . . .
C13 C 0.7936(4) 0.7708(6) 0.0795(3) 0.0452(10) Uani 1 1 d . . . . .
C14 C 0.4026(4) 0.5901(8) 0.2905(3) 0.0545(12) Uani 1 1 d . . . . .
C15 C 0.7669(5) 0.7456(8) 0.0011(3) 0.0539(12) Uani 1 1 d . . . . .
C16 C 0.7269(4) 0.3794(7) 0.0211(3) 0.0497(11) Uani 1 1 d . . . . .
C17 C 0.6832(4) 0.5812(8) -0.0075(2) 0.0543(11) Uani 1 1 d . . . . .
C18 C 0.4820(4) 0.2278(6) 0.2319(3) 0.0515(12) Uani 1 1 d . . . . .
C19 C 0.6389(4) 0.2627(8) 0.3017(3) 0.0538(12) Uani 1 1 d . . . . .
C20 C 0.3643(6) 0.7706(9) 0.3175(3) 0.0661(15) Uani 1 1 d . . . . .
C21 C 0.4144(5) 0.8742(9) 0.3690(3) 0.0661(15) Uani 1 1 d . . . . .
C22 C 0.5054(6) 0.7959(10) 0.3946(4) 0.0797(19) Uani 1 1 d . . . . .
C23 C 0.5465(5) 0.6155(9) 0.3689(4) 0.0683(15) Uani 1 1 d . . . . .
H8A H 0.856(3) 0.586(5) 0.158(2) 0.025(9) Uiso 1 1 d . . . . .
H18A H 0.514(4) 0.089(6) 0.225(3) 0.043(11) Uiso 1 1 d . . . . .
H21 H 0.389(4) 1.008(8) 0.389(3) 0.059(14) Uiso 1 1 d . . . . .
H12A H 0.551(5) 0.773(9) 0.018(3) 0.071(17) Uiso 1 1 d . . . . .
H16A H 0.674(4) 0.271(6) 0.011(2) 0.028(10) Uiso 1 1 d . . . . .
H17 H 0.658(4) 0.562(8) -0.059(3) 0.066(15) Uiso 1 1 d . . . . .
H8B H 0.898(4) 0.531(8) 0.083(3) 0.056(14) Uiso 1 1 d . . . . .
H9 H 0.782(3) 0.279(5) 0.1177(19) 0.020(8) Uiso 1 1 d . . . . .
H19A H 0.646(4) 0.113(9) 0.301(3) 0.071(16) Uiso 1 1 d . . . . .
H14 H 0.364(4) 0.510(8) 0.254(4) 0.062(14) Uiso 1 1 d . . . . .
H3A H 0.713(4) 0.862(6) 0.172(3) 0.046(12) Uiso 1 1 d . . . . .
H13 H 0.846(4) 0.877(7) 0.084(3) 0.042(12) Uiso 1 1 d . . . . .
H16B H 0.792(5) 0.342(7) -0.007(3) 0.063(16) Uiso 1 1 d . . . . .
H19B H 0.659(5) 0.317(9) 0.344(4) 0.069(19) Uiso 1 1 d . . . . .
H6 H 0.545(4) 0.694(7) 0.140(3) 0.042(11) Uiso 1 1 d . . . . .
H23 H 0.613(5) 0.569(10) 0.389(4) 0.09(2) Uiso 1 1 d . . . . .
H3B H 0.667(4) 0.949(9) 0.094(3) 0.068(16) Uiso 1 1 d . . . . .
H12B H 0.531(5) 0.522(9) 0.028(3) 0.066(16) Uiso 1 1 d . . . . .
H18B H 0.404(4) 0.218(7) 0.242(3) 0.059(14) Uiso 1 1 d . . . . .
H22 H 0.549(7) 0.858(11) 0.438(5) 0.12(3) Uiso 1 1 d . . . . .
H15A H 0.829(6) 0.710(10) -0.027(4) 0.09(2) Uiso 1 1 d . . . . .
H20 H 0.301(7) 0.813(11) 0.302(5) 0.12(3) Uiso 1 1 d . . . . .
H15B H 0.742(4) 0.880(8) -0.014(3) 0.062(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 O4 1.459(4) . ?
O1 C7 1.410(4) . ?
O2 C7 1.424(5) . ?
O2 O10 1.461(4) . ?
C3 C6 1.539(6) . ?
C3 C13 1.511(7) . ?
O4 C18 1.440(6) . ?
N5 C11 1.407(6) . ?
N5 C18 1.426(7) . ?
N5 C19 1.417(6) . ?
C6 C7 1.523(5) . ?
C6 C12 1.541(6) . ?
C7 C9 1.526(5) . ?
C8 C9 1.538(6) . ?
C8 C13 1.532(6) . ?
C9 C16 1.531(7) . ?
O10 C19 1.437(6) . ?
C11 C14 1.390(6) . ?
C11 C23 1.377(8) . ?
C12 C17 1.518(7) . ?
C13 C15 1.529(7) . ?
C14 C20 1.382(7) . ?
C15 C17 1.528(8) . ?
C16 C17 1.539(7) . ?
C20 C21 1.349(9) . ?
C21 C22 1.358(10) . ?
C22 C23 1.385(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O1 O4 110.9(2) . . ?
C7 O2 O10 108.0(3) . . ?
C13 C3 C6 109.8(3) . . ?
C18 O4 O1 107.3(3) . . ?
C11 N5 C18 119.7(4) . . ?
C11 N5 C19 120.7(4) . . ?
C19 N5 C18 115.5(4) . . ?
C3 C6 C12 109.0(4) . . ?
C7 C6 C3 109.1(3) . . ?
C7 C6 C12 108.6(3) . . ?
O1 C7 O2 110.1(3) . . ?
O1 C7 C6 114.4(3) . . ?
O1 C7 C9 104.4(3) . . ?
O2 C7 C6 104.7(3) . . ?
O2 C7 C9 113.1(3) . . ?
C6 C7 C9 110.5(3) . . ?
C13 C8 C9 109.3(4) . . ?
C7 C9 C8 108.3(3) . . ?
C7 C9 C16 109.8(4) . . ?
C16 C9 C8 109.6(4) . . ?
C19 O10 O2 107.3(3) . . ?
C14 C11 N5 120.2(4) . . ?
C23 C11 N5 122.5(4) . . ?
C23 C11 C14 117.2(5) . . ?
C17 C12 C6 110.2(4) . . ?
C3 C13 C8 109.4(4) . . ?
C3 C13 C15 110.1(4) . . ?
C15 C13 C8 109.6(4) . . ?
C20 C14 C11 120.2(5) . . ?
C17 C15 C13 109.5(4) . . ?
C9 C16 C17 109.6(3) . . ?
C12 C17 C15 110.4(4) . . ?
C12 C17 C16 108.8(4) . . ?
C15 C17 C16 108.8(4) . . ?
N5 C18 O4 115.2(3) . . ?
N5 C19 O10 116.3(4) . . ?
C21 C20 C14 122.3(6) . . ?
C20 C21 C22 117.9(6) . . ?
C21 C22 C23 121.5(6) . . ?
C11 C23 C22 120.9(6) . . ?


