# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_rac-2
_database_code_depnum_ccdc_archive 'CCDC 1907688'
loop_
_audit_author_name
_audit_author_address
'Aidar Gubaidullin'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS
Russia
;
_audit_update_record             
;
2019-06-11 deposited with the CCDC.	2020-02-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT915_rac-2               
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         42 %
RESPONSE: The Flac? parameter was not determined because the crystal is racemic and contains molecules of both enantiomers
;
# Added during the CSD deposition process: Tuesday 11 June 2019 10:29 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
rac-5-(2-methoxyphenoxymethyl)-2-oxazolidinones
_chemical_name_common            rac-mephenoxalone
_chemical_melting_point          414-415
_chemical_formula_moiety         'C11 H13 N O4'
_chemical_formula_sum            'C11 H13 N O4'
_chemical_formula_weight         223.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   19.5781(11)
_cell_length_b                   9.8640(6)
_cell_length_c                   5.5937(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1080.25(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9651
_cell_measurement_theta_min      4.48
_cell_measurement_theta_max      45.65

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.884
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.771
_exptl_absorpt_correction_T_max  0.886
_exptl_absorpt_process_details   
;
G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
Siemens Area Detector Absorption Correction Program.
Bruker AXS. Madison. Wisconsin. USA
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18683
_diffrn_reflns_av_unetI/netI     0.0117
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.482
_diffrn_reflns_theta_max         70.027
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.993

_reflns_number_total             1513
_reflns_number_gt                1482
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'APEX2 v2008.6-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_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)+(0.0393P)²+0.0887P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0031(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1513
_refine_ls_number_parameters     182
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0648
_refine_ls_wR_factor_gt          0.0643
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.39676(9) 0.4271(2) 0.9551(3) 0.0437(4) Uani 1 1 d . . . . .
C2 C 0.45125(7) 0.40681(17) 0.7623(3) 0.0410(4) Uani 1 1 d . . . . .
C3 C 0.48679(8) 0.2730(2) 0.7878(3) 0.0476(4) Uani 1 1 d . . . . .
C4 C 0.34621(8) 0.39630(18) 0.5849(3) 0.0431(4) Uani 1 1 d . . . . .
C5 C 0.57419(8) 0.14585(17) 0.5935(4) 0.0456(4) Uani 1 1 d . . . . .
C6 C 0.62436(8) 0.14218(18) 0.4147(4) 0.0474(4) Uani 1 1 d . . . . .
C7 C 0.66976(9) 0.0339(2) 0.4078(4) 0.0576(5) Uani 1 1 d . . . . .
H7 H 0.7034 0.0310 0.2906 0.069 Uiso 1 1 calc R U . . .
C8 C 0.66521(11) -0.0695(2) 0.5743(5) 0.0661(6) Uani 1 1 d . . . . .
H8 H 0.6961 -0.1410 0.5699 0.079 Uiso 1 1 calc R U . . .
C9 C 0.61521(12) -0.0667(2) 0.7454(5) 0.0661(6) Uani 1 1 d . . . . .
H9 H 0.6119 -0.1371 0.8552 0.079 Uiso 1 1 calc R U . . .
C10 C 0.56933(10) 0.0409(2) 0.7560(5) 0.0590(5) Uani 1 1 d . . . . .
H10 H 0.5354 0.0422 0.8724 0.071 Uiso 1 1 calc R U . . .
C11 C 0.67825(11) 0.2553(3) 0.0887(5) 0.0646(6) Uani 1 1 d . . . . .
N1 N 0.33545(7) 0.39966(16) 0.8197(3) 0.0457(4) Uani 1 1 d . . . . .
O1 O 0.30538(6) 0.38416(17) 0.4235(3) 0.0626(4) Uani 1 1 d . . . . .
O2 O 0.41396(5) 0.41010(14) 0.5391(2) 0.0476(3) Uani 1 1 d . . . . .
O3 O 0.53319(6) 0.25875(13) 0.5924(3) 0.0540(3) Uani 1 1 d . . . . .
O4 O 0.62429(7) 0.24912(14) 0.2587(3) 0.0608(4) Uani 1 1 d . . . . .
H1 H 0.2941(12) 0.398(2) 0.880(5) 0.071(7) Uiso 1 1 d . . . . .
H2 H 0.4833(8) 0.4786(18) 0.746(4) 0.043(4) Uiso 1 1 d . . . . .
H11 H 0.3962(11) 0.520(3) 1.016(5) 0.064(6) Uiso 1 1 d . . . . .
H21 H 0.4021(10) 0.3628(19) 1.079(4) 0.047(5) Uiso 1 1 d . . . . .
H31 H 0.5116(10) 0.268(2) 0.936(5) 0.055(6) Uiso 1 1 d . . . . .
H32 H 0.4517(11) 0.198(2) 0.783(4) 0.057(6) Uiso 1 1 d . . . . .
H111 H 0.6669(11) 0.331(3) -0.008(5) 0.071(7) Uiso 1 1 d . . . . .
H112 H 0.7238(14) 0.264(3) 0.160(5) 0.089(9) Uiso 1 1 d . . . . .
H113 H 0.6789(12) 0.170(3) -0.003(6) 0.085(8) 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
C1 N1 1.445(2) . ?
C1 C2 1.530(2) . ?
C1 H11 0.98(2) . ?
C1 H21 0.95(2) . ?
C2 O2 1.4469(19) . ?
C2 C3 1.499(2) . ?
C2 H2 0.951(17) . ?
C3 O3 1.428(2) . ?
C3 H31 0.96(3) . ?
C3 H32 1.01(2) . ?
C4 O1 1.212(2) . ?
C4 N1 1.330(2) . ?
C4 O2 1.3577(19) . ?
C5 O3 1.373(2) . ?
C5 C10 1.381(3) . ?
C5 C6 1.402(2) . ?
C6 O4 1.369(3) . ?
C6 C7 1.390(2) . ?
C7 C8 1.384(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.369(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O4 1.423(2) . ?
C11 H111 0.95(3) . ?
C11 H112 0.98(3) . ?
C11 H113 0.98(3) . ?
N1 H1 0.88(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 100.68(14) . . ?
N1 C1 H11 110.4(13) . . ?
C2 C1 H11 112.0(14) . . ?
N1 C1 H21 110.5(12) . . ?
C2 C1 H21 110.7(12) . . ?
H11 C1 H21 112.1(19) . . ?
O2 C2 C3 109.64(15) . . ?
O2 C2 C1 104.68(12) . . ?
C3 C2 C1 111.82(15) . . ?
O2 C2 H2 103.5(13) . . ?
C3 C2 H2 111.0(10) . . ?
C1 C2 H2 115.5(12) . . ?
O3 C3 C2 108.01(14) . . ?
O3 C3 H31 109.5(13) . . ?
C2 C3 H31 111.1(13) . . ?
O3 C3 H32 109.8(13) . . ?
C2 C3 H32 109.0(11) . . ?
H31 C3 H32 109.4(18) . . ?
O1 C4 N1 129.30(16) . . ?
O1 C4 O2 120.89(16) . . ?
N1 C4 O2 109.81(15) . . ?
O3 C5 C10 124.81(17) . . ?
O3 C5 C6 115.29(15) . . ?
C10 C5 C6 119.89(17) . . ?
O4 C6 C7 125.09(18) . . ?
O4 C6 C5 115.73(15) . . ?
C7 C6 C5 119.18(18) . . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 120.07(19) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.5(2) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C5 C10 C9 119.9(2) . . ?
C5 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
O4 C11 H111 104.0(15) . . ?
O4 C11 H112 114.1(18) . . ?
H111 C11 H112 112(2) . . ?
O4 C11 H113 108.7(15) . . ?
H111 C11 H113 112(2) . . ?
H112 C11 H113 106(2) . . ?
C4 N1 C1 112.98(15) . . ?
C4 N1 H1 121.8(18) . . ?
C1 N1 H1 124.5(17) . . ?
C4 O2 C2 109.12(13) . . ?
C5 O3 C3 116.64(14) . . ?
C6 O4 C11 117.30(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O2 15.86(17) . . . . ?
N1 C1 C2 C3 -102.77(17) . . . . ?
O2 C2 C3 O3 60.50(17) . . . . ?
C1 C2 C3 O3 176.14(14) . . . . ?
O3 C5 C6 O4 -2.1(2) . . . . ?
C10 C5 C6 O4 178.61(18) . . . . ?
O3 C5 C6 C7 177.69(17) . . . . ?
C10 C5 C6 C7 -1.6(3) . . . . ?
O4 C6 C7 C8 -179.80(19) . . . . ?
C5 C6 C7 C8 0.5(3) . . . . ?
C6 C7 C8 C9 0.9(3) . . . . ?
C7 C8 C9 C10 -1.0(3) . . . . ?
O3 C5 C10 C9 -177.8(2) . . . . ?
C6 C5 C10 C9 1.5(3) . . . . ?
C8 C9 C10 C5 -0.1(3) . . . . ?
O1 C4 N1 C1 -175.0(2) . . . . ?
O2 C4 N1 C1 4.5(2) . . . . ?
C2 C1 N1 C4 -12.9(2) . . . . ?
O1 C4 O2 C2 -173.45(17) . . . . ?
N1 C4 O2 C2 7.0(2) . . . . ?
C3 C2 O2 C4 105.45(16) . . . . ?
C1 C2 O2 C4 -14.65(18) . . . . ?
C10 C5 O3 C3 6.1(3) . . . . ?
C6 C5 O3 C3 -173.15(15) . . . . ?
C2 C3 O3 C5 175.64(14) . . . . ?
C7 C6 O4 C11 -5.4(3) . . . . ?
C5 C6 O4 C11 174.35(17) . . . . ?

_refine_diff_density_max         0.117
_refine_diff_density_min         -0.092
_refine_diff_density_rms         0.020


_exptl_crystal_recrystallization_method 
'slow evaporation of sample solutions from a mixture of CHCl3/CCl4'
####################################################################### 
# 
# 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_R-2
_database_code_depnum_ccdc_archive 'CCDC 1907689'
loop_
_audit_author_name
_audit_author_address
'Aidar Gubaidullin'
;Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center of RAS
Russia
;
_audit_update_record             
;
2019-06-11 deposited with the CCDC.	2020-02-12 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT915_R-2                 
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         77 %
RESPONSE: The absolute configuration of the molecule was not determined because the experiment was performed on Mo-radiation, the molecule contains only light atoms, and the evaluation of the Flack parameter would be incorrect. In addition, the absolute configuration of the molecule is known from the conditions of synthesis.
;
# Added during the CSD deposition process: Tuesday 11 June 2019 10:29 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
(R)-5-(2-methoxyphenoxymethyl)-2-oxazolidinones
_chemical_name_common            (R)-mephenoxalone
_chemical_melting_point          398-400
_chemical_formula_moiety         'C11 H13 N O4'
_chemical_formula_sum            'C11 H13 N O4'
_chemical_formula_weight         223.22

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   9.7048(7)
_cell_length_b                   5.5085(4)
_cell_length_c                   10.4326(7)
_cell_angle_alpha                90
_cell_angle_beta                 108.560(4)
_cell_angle_gamma                90
_cell_volume                     528.71(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3956
_cell_measurement_theta_min      4.01
_cell_measurement_theta_max      30.58

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.760
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.110
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             236
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9002
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_process_details   
;
G.M. Sheldrick (1998a). SADABS v.2.01, Bruker.
Siemens Area Detector Absorption Correction Program.
Bruker AXS. Madison. Wisconsin. USA
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9737
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.472
_diffrn_reflns_theta_max         30.608
_diffrn_reflns_theta_full        28.000
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_Laue_measured_fraction_full 0.995
_reflns_number_total             2692
_reflns_number_gt                2181
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'APEX2 v2008.6-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_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)+(0.0362P)²+0.0368P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_chemical_absolute_configuration rm

_refine_ls_number_reflns         2692
_refine_ls_number_parameters     150
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.0811
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4914(3) 0.9770(4) -0.2190(2) 0.0153(5) Uani 1 1 d . . . . .
H11 H 0.3944 1.0406 -0.2238 0.018 Uiso 1 1 calc R U . . .
H12 H 0.5616 1.1130 -0.2029 0.018 Uiso 1 1 calc R U . . .
C2 C 0.5426(2) 0.7787(4) -0.1108(2) 0.0148(4) Uani 1 1 d . . . . .
H2 H 0.4856 0.7844 -0.0461 0.018 Uiso 1 1 calc R U . . .
C3 C 0.7025(2) 0.8044(4) -0.0370(2) 0.0158(5) Uani 1 1 d . . . . .
H31 H 0.7572 0.8079 -0.1026 0.019 Uiso 1 1 calc R U . . .
H32 H 0.7214 0.9582 0.0147 0.019 Uiso 1 1 calc R U . . .
C4 C 0.4988(2) 0.6018(4) -0.3190(2) 0.0144(5) Uani 1 1 d . . . . .
C5 C 0.8925(2) 0.6066(4) 0.1326(2) 0.0157(5) Uani 1 1 d . . . . .
C6 C 0.9345(2) 0.4218(4) 0.2305(2) 0.0167(5) Uani 1 1 d . . . . .
C7 C 1.0748(2) 0.4175(5) 0.3189(2) 0.0194(5) Uani 1 1 d . . . . .
H7 H 1.1035 0.2936 0.3854 0.023 Uiso 1 1 calc R U . . .
C8 C 1.1749(2) 0.5942(5) 0.3109(2) 0.0211(5) Uani 1 1 d . . . . .
H8 H 1.2706 0.5928 0.3734 0.025 Uiso 1 1 calc R U . . .
C9 C 1.1349(2) 0.7701(5) 0.2127(2) 0.0217(5) Uani 1 1 d . . . . .
H9 H 1.2038 0.8877 0.2058 0.026 Uiso 1 1 calc R U . . .
C10 C 0.9930(2) 0.7763(4) 0.1229(2) 0.0187(5) Uani 1 1 d . . . . .
H10 H 0.9657 0.8980 0.0549 0.022 Uiso 1 1 calc R U . . .
C11 C 0.8604(3) 0.0940(5) 0.3429(2) 0.0223(5) Uani 1 1 d . . . . .
H111 H 0.7775 -0.0142 0.3327 0.034 Uiso 1 1 calc R U . . .
H112 H 0.8792 0.1885 0.4263 0.034 Uiso 1 1 calc R U . . .
H113 H 0.9465 -0.0027 0.3471 0.034 Uiso 1 1 calc R U . . .
N1 N 0.4863(2) 0.8408(3) -0.33971(19) 0.0160(4) Uani 1 1 d . . . . .
O1 O 0.49415(17) 0.4389(3) -0.39893(14) 0.0193(4) Uani 1 1 d . . . . .
O2 O 0.51685(16) 0.5520(3) -0.18610(14) 0.0151(4) Uani 1 1 d . . . . .
O3 O 0.74920(15) 0.6030(3) 0.05291(14) 0.0174(4) Uani 1 1 d . . . . .
O4 O 0.82836(15) 0.2554(3) 0.22958(14) 0.0190(4) Uani 1 1 d . . . . .
H1 H 0.481(3) 0.903(5) -0.419(3) 0.031(7) 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
C1 N1 1.453(3) . ?
C1 C2 1.536(3) . ?
C1 H11 0.9900 . ?
C1 H12 0.9900 . ?
C2 O2 1.454(3) . ?
C2 C3 1.503(3) . ?
C2 H2 1.0000 . ?
C3 O3 1.430(2) . ?
C3 H31 0.9900 . ?
C3 H32 0.9900 . ?
C4 O1 1.216(3) . ?
C4 N1 1.333(3) . ?
C4 O2 1.369(2) . ?
C5 O3 1.374(2) . ?
C5 C10 1.378(3) . ?
C5 C6 1.407(3) . ?
C6 O4 1.376(3) . ?
C6 C7 1.381(3) . ?
C7 C8 1.396(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.373(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.399(3) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 O4 1.432(2) . ?
C11 H111 0.9800 . ?
C11 H112 0.9800 . ?
C11 H113 0.9800 . ?
N1 H1 0.88(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 100.57(17) . . ?
N1 C1 H11 111.7 . . ?
C2 C1 H11 111.7 . . ?
N1 C1 H12 111.7 . . ?
C2 C1 H12 111.7 . . ?
H11 C1 H12 109.4 . . ?
O2 C2 C3 109.25(17) . . ?
O2 C2 C1 104.70(15) . . ?
C3 C2 C1 110.43(19) . . ?
O2 C2 H2 110.8 . . ?
C3 C2 H2 110.8 . . ?
C1 C2 H2 110.8 . . ?
O3 C3 C2 108.79(18) . . ?
O3 C3 H31 109.9 . . ?
C2 C3 H31 109.9 . . ?
O3 C3 H32 109.9 . . ?
C2 C3 H32 109.9 . . ?
H31 C3 H32 108.3 . . ?
O1 C4 N1 129.5(2) . . ?
O1 C4 O2 120.8(2) . . ?
N1 C4 O2 109.7(2) . . ?
O3 C5 C10 124.6(2) . . ?
O3 C5 C6 115.61(19) . . ?
C10 C5 C6 119.74(19) . . ?
O4 C6 C7 124.7(2) . . ?
O4 C6 C5 115.70(18) . . ?
C7 C6 C5 119.6(2) . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 120.2(2) . . ?
C5 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
O4 C11 H111 109.5 . . ?
O4 C11 H112 109.5 . . ?
H111 C11 H112 109.5 . . ?
O4 C11 H113 109.5 . . ?
H111 C11 H113 109.5 . . ?
H112 C11 H113 109.5 . . ?
C4 N1 C1 113.16(19) . . ?
C4 N1 H1 120.5(19) . . ?
C1 N1 H1 126.2(19) . . ?
C4 O2 C2 108.67(16) . . ?
C5 O3 C3 115.71(17) . . ?
C6 O4 C11 116.26(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 O2 -16.68(19) . . . . ?
N1 C1 C2 C3 100.8(2) . . . . ?
O2 C2 C3 O3 -59.5(2) . . . . ?
C1 C2 C3 O3 -174.15(15) . . . . ?
O3 C5 C6 O4 2.8(3) . . . . ?
C10 C5 C6 O4 -177.74(19) . . . . ?
O3 C5 C6 C7 -177.23(19) . . . . ?
C10 C5 C6 C7 2.2(3) . . . . ?
O4 C6 C7 C8 179.6(2) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C6 C7 C8 C9 -1.6(3) . . . . ?
C7 C8 C9 C10 1.7(3) . . . . ?
O3 C5 C10 C9 177.3(2) . . . . ?
C6 C5 C10 C9 -2.1(3) . . . . ?
C8 C9 C10 C5 0.2(3) . . . . ?
O1 C4 N1 C1 177.4(2) . . . . ?
O2 C4 N1 C1 -1.5(3) . . . . ?
C2 C1 N1 C4 11.7(2) . . . . ?
O1 C4 O2 C2 170.59(18) . . . . ?
N1 C4 O2 C2 -10.4(2) . . . . ?
C3 C2 O2 C4 -101.10(19) . . . . ?
C1 C2 O2 C4 17.2(2) . . . . ?
C10 C5 O3 C3 -5.6(3) . . . . ?
C6 C5 O3 C3 173.80(18) . . . . ?
C2 C3 O3 C5 -177.10(17) . . . . ?
C7 C6 O4 C11 11.2(3) . . . . ?
C5 C6 O4 C11 -168.92(18) . . . . ?

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'slow evaporation of sample solutions from a mixture of CHCl3/CCl4'
