# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

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

data_QF2_046_a
_database_code_depnum_ccdc_archive 'CCDC 1921458'
loop_
_audit_author_name
_audit_author_address
'Jerome Marrot'
;Institut Lavoisier de Versailles
France
;
_audit_update_record             
;
2019-06-06 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H19 Cl N O4'
_chemical_formula_weight         252.71

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'

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

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

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

_cell_length_a                   7.9383(2)
_cell_length_b                   8.9382(2)
_cell_length_c                   16.3920(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1163.08(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9816
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      29.98

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             540
_exptl_transmission_factor_min   0.7164
_exptl_transmission_factor_max   0.7460
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.328
_shelx_estimated_absorpt_T_min   0.908
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Sheldrick, V2014/5)'
_exptl_absorpt_special_details   'Blessing, Acta Cryst. (1995) A51, 33-38'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microsource
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48658
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.485
_diffrn_reflns_theta_max         30.043
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3408
_reflns_number_gt                3289
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²+0.1650P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1374 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.004(11)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3408
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0230
_refine_ls_wR_factor_ref         0.0637
_refine_ls_wR_factor_gt          0.0625
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.70776(4) 0.57152(4) 0.59820(2) 0.01926(8) Uani 1 1 d . . . . .
N1 N 0.35720(14) 0.61732(12) 0.48111(7) 0.0128(2) Uani 1 1 d . . . . .
H1A H 0.319079 0.692557 0.448576 0.015 Uiso 0.5 1 calc R U P . .
H1B H 0.438186 0.656036 0.514242 0.015 Uiso 0.5 1 calc R U P . .
C2 C 0.21304(17) 0.56170(14) 0.53323(8) 0.0144(2) Uani 1 1 d . . . . .
H2 H 0.160564 0.652185 0.558550 0.017 Uiso 1 1 calc R U . . .
C3 C 0.07855(17) 0.49237(15) 0.47741(8) 0.0157(2) Uani 1 1 d . . . . .
H3 H -0.007991 0.444077 0.513070 0.019 Uiso 1 1 calc R U . . .
O3 O -0.00278(14) 0.60884(12) 0.43289(7) 0.0203(2) Uani 1 1 d . . . . .
H3A H 0.049210 0.623991 0.389027 0.030 Uiso 1 1 calc R U . . .
C4 C 0.15102(17) 0.37108(15) 0.42125(8) 0.0146(2) Uani 1 1 d . . . . .
H4 H 0.061120 0.335806 0.383095 0.018 Uiso 1 1 calc R U . . .
O4 O 0.19880(15) 0.25121(11) 0.47375(6) 0.0201(2) Uani 1 1 d . . . . .
H4A H 0.203343 0.171331 0.446847 0.030 Uiso 1 1 calc R U . . .
C5 C 0.30219(16) 0.43022(15) 0.37129(7) 0.0120(2) Uani 1 1 d . . . . .
O5 O 0.24003(13) 0.54963(11) 0.32061(6) 0.0160(2) Uani 1 1 d . . . . .
H5 H 0.212412 0.515209 0.274838 0.024 Uiso 1 1 calc R U . . .
C6 C 0.38559(18) 0.30780(16) 0.32039(8) 0.0164(3) Uani 1 1 d . . . . .
H6A H 0.302268 0.266573 0.281479 0.020 Uiso 1 1 calc R U . . .
H6B H 0.422052 0.225591 0.356806 0.020 Uiso 1 1 calc R U . . .
C7 C 0.53784(19) 0.36646(18) 0.27310(9) 0.0196(3) Uani 1 1 d . . . . .
H7A H 0.499438 0.439883 0.231880 0.024 Uiso 1 1 calc R U . . .
H7B H 0.592312 0.282401 0.243929 0.024 Uiso 1 1 calc R U . . .
C8 C 0.66643(17) 0.44078(18) 0.32946(9) 0.0190(3) Uani 1 1 d . . . . .
H8A H 0.717882 0.363868 0.365065 0.023 Uiso 1 1 calc R U . . .
H8B H 0.757196 0.485955 0.296159 0.023 Uiso 1 1 calc R U . . .
C9 C 0.58557(16) 0.56183(16) 0.38241(8) 0.0145(2) Uani 1 1 d . . . . .
H9A H 0.669327 0.600510 0.421870 0.017 Uiso 1 1 calc R U . . .
H9B H 0.548353 0.646064 0.347578 0.017 Uiso 1 1 calc R U . . .
C10 C 0.43525(16) 0.49780(14) 0.42814(7) 0.0114(2) Uani 1 1 d . . . . .
H10 H 0.477277 0.416373 0.464692 0.014 Uiso 1 1 calc R U . . .
C11 C 0.27482(19) 0.46377(15) 0.60355(8) 0.0188(3) Uani 1 1 d . . . . .
H11A H 0.178608 0.407400 0.626618 0.023 Uiso 1 1 calc R U . . .
H11B H 0.357884 0.390537 0.582704 0.023 Uiso 1 1 calc R U . . .
O11 O 0.35068(15) 0.55188(14) 0.66613(6) 0.0237(2) Uani 1 1 d . . . . .
H11 H 0.454241 0.560664 0.656759 0.036 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C10 1.5097(16) . ?
N1 C2 1.5122(16) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
C2 C11 1.5282(18) . ?
C2 C3 1.5366(19) . ?
C2 H2 1.0000 . ?
C3 O3 1.4258(17) . ?
C3 C4 1.5342(19) . ?
C3 H3 1.0000 . ?
O3 H3A 0.8400 . ?
C4 O4 1.4256(16) . ?
C4 C5 1.5459(18) . ?
C4 H4 1.0000 . ?
O4 H4A 0.8400 . ?
C5 O5 1.4398(15) . ?
C5 C6 1.5270(18) . ?
C5 C10 1.5326(17) . ?
O5 H5 0.8400 . ?
C6 C7 1.529(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.529(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.528(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5210(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10 1.0000 . ?
C11 O11 1.4265(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
O11 H11 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C2 113.76(10) . . ?
C10 N1 H1A 108.8 . . ?
C2 N1 H1A 108.8 . . ?
C10 N1 H1B 108.8 . . ?
C2 N1 H1B 108.8 . . ?
H1A N1 H1B 107.7 . . ?
N1 C2 C11 111.82(11) . . ?
N1 C2 C3 108.78(10) . . ?
C11 C2 C3 116.18(11) . . ?
N1 C2 H2 106.5 . . ?
C11 C2 H2 106.5 . . ?
C3 C2 H2 106.5 . . ?
O3 C3 C4 112.25(11) . . ?
O3 C3 C2 108.96(11) . . ?
C4 C3 C2 112.44(11) . . ?
O3 C3 H3 107.7 . . ?
C4 C3 H3 107.7 . . ?
C2 C3 H3 107.7 . . ?
C3 O3 H3A 109.5 . . ?
O4 C4 C3 105.59(10) . . ?
O4 C4 C5 111.73(11) . . ?
C3 C4 C5 111.55(11) . . ?
O4 C4 H4 109.3 . . ?
C3 C4 H4 109.3 . . ?
C5 C4 H4 109.3 . . ?
C4 O4 H4A 109.5 . . ?
O5 C5 C6 111.37(10) . . ?
O5 C5 C10 107.15(10) . . ?
C6 C5 C10 108.41(11) . . ?
O5 C5 C4 107.04(10) . . ?
C6 C5 C4 112.40(11) . . ?
C10 C5 C4 110.34(10) . . ?
C5 O5 H5 109.5 . . ?
C5 C6 C7 111.97(11) . . ?
C5 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C6 C7 C8 111.75(11) . . ?
C6 C7 H7A 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C8 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C9 C8 C7 111.74(11) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C10 C9 C8 110.06(11) . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
N1 C10 C9 109.83(10) . . ?
N1 C10 C5 110.23(10) . . ?
C9 C10 C5 112.91(10) . . ?
N1 C10 H10 107.9 . . ?
C9 C10 H10 107.9 . . ?
C5 C10 H10 107.9 . . ?
O11 C11 C2 111.20(11) . . ?
O11 C11 H11A 109.4 . . ?
C2 C11 H11A 109.4 . . ?
O11 C11 H11B 109.4 . . ?
C2 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 O11 H11 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O11 H11 Cl1 0.84 2.23 3.0505(12) 164.8 . yes
C10 H10 O4 1.00 2.52 3.4522(16) 154.8 4_556 yes
C9 H9A O3 0.99 2.61 3.3971(17) 136.5 1_655 yes
C9 H9A Cl1 0.99 2.92 3.6689(13) 133.4 . yes
O5 H5 O11 0.84 1.95 2.7846(14) 176.4 2_564 yes
O4 H4A Cl1 0.84 2.29 3.1173(10) 167.0 4_456 yes
O3 H3A O5 0.84 2.00 2.7171(15) 143.0 . yes
C3 H3 Cl1 1.00 2.89 3.6172(14) 130.5 1_455 yes
N1 H1B O3 0.91 2.32 3.0354(15) 135.2 4_566 yes
N1 H1B Cl1 0.91 2.65 3.4053(12) 140.4 . yes
N1 H1A Cl1 0.91 2.41 3.2912(12) 162.6 4_466 yes

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.042

