# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_r20220718a_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2253951'
loop_
_audit_author_name
_audit_author_address
'Lijie Gao'
;Tianjin University
China
;
_audit_update_record             
;
2023-04-04 deposited with the CCDC.	2023-06-13 downloaded from the CCDC.
;
_audit_creation_date             2022-07-18
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Dimethyl 5-aminoisophthalate'
_chemical_formula_moiety         'C10 H11 N O4'
_chemical_formula_sum            'C10 H11 N O4'
_chemical_formula_weight         209.20
_chemical_absolute_configuration unk
_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           7
_space_group_name_H-M_alt        'P 1 n 1'
_space_group_name_Hall           'P -2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y, z+1/2'

_cell_length_a                   9.5646(11)
_cell_length_b                   3.7993(5)
_cell_length_c                   13.5636(17)
_cell_angle_alpha                90
_cell_angle_beta                 106.084(13)
_cell_angle_gamma                90
_cell_volume                     473.59(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2710
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.6000
_cell_measurement_theta_min      2.2910
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53702
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2785
_diffrn_reflns_point_group_measured_fraction_full 0.559
_diffrn_reflns_point_group_measured_fraction_max 0.506
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.835
_diffrn_reflns_theta_min         2.331
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00  65.00   2.00    2.00    --  -25.00  45.00   0.00   90
  2  ω   -115.00  45.00   2.00    2.00    --  -25.00  45.00  90.00   80
  3  ω   -115.00  25.00   2.00    2.00    --  -25.00  45.00 180.00   70
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.084
_reflns_Friedel_fraction_full    0.119
_reflns_Friedel_fraction_max     0.078
_reflns_number_gt                2361
_reflns_number_total             2785
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.184
_refine_ls_abs_structure_details 
;
 Flack x determined using 348 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.9(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0637
_refine_ls_restrained_S_all      1.048
_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)+(0.1404P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1799
_refine_ls_wR_factor_ref         0.1842
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.588(3)
 0.412(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Rotating group:
 N1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.2011(3) 0.1036(9) 0.4058(2) 0.0263(7) Uani 1 1 d . . . . .
O2 O 0.2561(3) -0.0489(8) 0.5711(2) 0.0210(6) Uani 1 1 d . . . . .
O3 O 0.6067(3) 0.6481(9) 0.2815(2) 0.0239(7) Uani 1 1 d . . . . .
O4 O 0.8304(3) 0.5073(8) 0.3755(2) 0.0188(6) Uani 1 1 d . . . . .
N1 N 0.7895(4) 0.0996(11) 0.7128(3) 0.0262(8) Uani 1 1 d . . . . .
H1A H 0.743906 0.019589 0.754605 0.031 Uiso 1 1 d R U . . .
H1B H 0.850331 -0.056158 0.704136 0.031 Uiso 1 1 d R U . . .
C1 C 0.6911(3) 0.1729(9) 0.6203(3) 0.0148(7) Uani 1 1 d . . . . .
C2 C 0.5438(4) 0.0898(10) 0.6029(3) 0.0145(6) Uani 1 1 d . . . . .
H2 H 0.510709 -0.015670 0.655823 0.017 Uiso 1 1 calc R U . . .
C3 C 0.4460(3) 0.1608(9) 0.5086(3) 0.0125(6) Uani 1 1 d . . . . .
C4 C 0.4917(3) 0.3126(9) 0.4297(3) 0.0131(6) Uani 1 1 d . . . . .
H4 H 0.423971 0.364783 0.365639 0.016 Uiso 1 1 calc R U . . .
C5 C 0.6384(3) 0.3865(9) 0.4465(3) 0.0127(6) Uani 1 1 d . . . . .
C6 C 0.7367(4) 0.3208(10) 0.5399(3) 0.0151(7) Uani 1 1 d . . . . .
H6 H 0.836559 0.376413 0.549989 0.018 Uiso 1 1 calc R U . . .
C7 C 0.2892(3) 0.0729(10) 0.4881(3) 0.0149(7) Uani 1 1 d . . . . .
C8 C 0.1066(4) -0.1510(11) 0.5564(3) 0.0240(9) Uani 1 1 d . . . . .
H8A H 0.084472 -0.355836 0.510835 0.036 Uiso 1 1 calc R U . . .
H8B H 0.042598 0.044701 0.525643 0.036 Uiso 1 1 calc R U . . .
H8C H 0.091048 -0.211334 0.622858 0.036 Uiso 1 1 calc R U . . .
C9 C 0.6867(3) 0.5309(10) 0.3592(3) 0.0148(6) Uani 1 1 d . . . . .
C10 C 0.8870(4) 0.6390(11) 0.2943(3) 0.0218(8) Uani 1 1 d . . . . .
H10A H 0.842191 0.510648 0.230716 0.033 Uiso 1 1 calc R U . . .
H10B H 0.992714 0.605473 0.313167 0.033 Uiso 1 1 calc R U . . .
H10C H 0.864566 0.890271 0.283911 0.033 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
O1 C7 1.203(5) . ?
O2 C7 1.334(4) . ?
O2 C8 1.441(4) . ?
O3 C9 1.203(4) . ?
O4 C9 1.333(4) . ?
O4 C10 1.444(4) . ?
N1 H1A 0.8604 . ?
N1 H1B 0.8609 . ?
N1 C1 1.373(5) . ?
C1 C2 1.399(5) . ?
C1 C6 1.399(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.386(5) . ?
C3 C4 1.389(5) . ?
C3 C7 1.485(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.387(4) . ?
C5 C6 1.376(5) . ?
C5 C9 1.490(4) . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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 O2 C8 115.8(3) . . ?
C9 O4 C10 115.9(3) . . ?
H1A N1 H1B 109.4 . . ?
C1 N1 H1A 109.3 . . ?
C1 N1 H1B 109.4 . . ?
N1 C1 C2 120.8(3) . . ?
N1 C1 C6 120.8(3) . . ?
C6 C1 C2 118.4(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 C7 121.2(3) . . ?
C4 C3 C7 117.8(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 C9 117.8(3) . . ?
C6 C5 C4 121.1(3) . . ?
C6 C5 C9 121.0(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
O1 C7 O2 123.2(3) . . ?
O1 C7 C3 124.3(3) . . ?
O2 C7 C3 112.5(3) . . ?
O2 C8 H8A 109.5 . . ?
O2 C8 H8B 109.5 . . ?
O2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O3 C9 O4 123.2(3) . . ?
O3 C9 C5 124.7(3) . . ?
O4 C9 C5 112.1(3) . . ?
O4 C10 H10A 109.5 . . ?
O4 C10 H10B 109.5 . . ?
O4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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 C3 -179.1(4) . . . . ?
N1 C1 C6 C5 178.5(4) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C1 C2 C3 C7 179.6(3) . . . . ?
C2 C1 C6 C5 0.8(5) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C2 C3 C7 O1 -174.2(4) . . . . ?
C2 C3 C7 O2 5.0(5) . . . . ?
C3 C4 C5 C6 -1.8(5) . . . . ?
C3 C4 C5 C9 176.7(3) . . . . ?
C4 C3 C7 O1 5.0(6) . . . . ?
C4 C3 C7 O2 -175.7(3) . . . . ?
C4 C5 C6 C1 0.8(5) . . . . ?
C4 C5 C9 O3 14.2(6) . . . . ?
C4 C5 C9 O4 -164.1(3) . . . . ?
C6 C1 C2 C3 -1.4(5) . . . . ?
C6 C5 C9 O3 -167.3(4) . . . . ?
C6 C5 C9 O4 14.4(5) . . . . ?
C7 C3 C4 C5 -178.1(3) . . . . ?
C8 O2 C7 O1 1.2(6) . . . . ?
C8 O2 C7 C3 -178.0(3) . . . . ?
C9 C5 C6 C1 -177.6(3) . . . . ?
C10 O4 C9 O3 1.2(5) . . . . ?
C10 O4 C9 C5 179.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.588(3)
2 0.412(3)

_twin_special_details            
;
Component 2 rotated by 179.9695° 
around [0.71 0.00 -0.71] (reciprocal) or [0.94 -0.00 -0.35] (direct)
;
####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 2254007'
loop_
_audit_author_name
_audit_author_address
'Lijie Gao'
;Tianjin University
China
;
_audit_update_record             
;
2023-05-17 deposited with the CCDC.	2023-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
Dimethyl 5-aminoisophthalate  
;
_chemical_name_common            
3,5-Dicarbomethoxyaniline;3-benzenedicarboxylicacid,5-amino-dimethylester;5-Amino-1,3-isophthalic
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H11 N O4'
_chemical_formula_weight         209.20

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   7.1188(14)
_cell_length_b                   18.663(4)
_cell_length_c                   7.9590(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.09(3)
_cell_angle_gamma                90.00
_cell_volume                     1016.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9950
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      27.48

_exptl_crystal_description       Strip
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9738
_exptl_absorpt_correction_T_max  0.9841
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  Rigaku
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9950
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         27.48
_reflns_number_total             2326
_reflns_number_gt                1679
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1200P)²+0.0000P] 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     SHELXL
_refine_ls_extinction_coef       0.043(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2326
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1765
_refine_ls_wR_factor_gt          0.1588
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.5079(2) 0.41679(6) 0.36249(17) 0.0627(4) Uani 1 1 d . . .
O2 O 0.4541(2) 0.30321(7) 0.27687(18) 0.0736(5) Uani 1 1 d . . .
O3 O 0.0408(3) 0.59171(7) -0.29110(19) 0.0759(5) Uani 1 1 d . . .
O4 O 0.20484(19) 0.60954(6) -0.01243(18) 0.0615(4) Uani 1 1 d . . .
N1 N 0.1641(3) 0.32693(8) -0.3782(2) 0.0664(5) Uani 1 1 d . . .
H1A H 0.1049 0.3418 -0.4816 0.080 Uiso 1 1 calc R . .
H1B H 0.1977 0.2827 -0.3614 0.080 Uiso 1 1 calc R . .
C1 C 0.6144(4) 0.39375(13) 0.5354(3) 0.0774(7) Uani 1 1 d . . .
H1C H 0.6572 0.4349 0.6083 0.116 Uiso 1 1 calc R . .
H1D H 0.7259 0.3661 0.5290 0.116 Uiso 1 1 calc R . .
H1E H 0.5310 0.3649 0.5842 0.116 Uiso 1 1 calc R . .
C2 C 0.4371(3) 0.36642(9) 0.2452(2) 0.0485(4) Uani 1 1 d . . .
C3 C 0.3385(2) 0.39633(8) 0.0697(2) 0.0423(4) Uani 1 1 d . . .
C4 C 0.2978(2) 0.35005(8) -0.0714(2) 0.0454(4) Uani 1 1 d . . .
H4A H 0.3330 0.3021 -0.0537 0.055 Uiso 1 1 calc R . .
C5 C 0.2051(2) 0.37401(9) -0.2393(2) 0.0463(4) Uani 1 1 d . . .
C6 C 0.1528(2) 0.44609(9) -0.2617(2) 0.0460(4) Uani 1 1 d . . .
H6A H 0.0900 0.4633 -0.3727 0.055 Uiso 1 1 calc R . .
C7 C 0.1936(2) 0.49235(8) -0.1197(2) 0.0427(4) Uani 1 1 d . . .
C8 C 0.1362(3) 0.56877(9) -0.1537(2) 0.0481(4) Uani 1 1 d . . .
C9 C 0.1624(3) 0.68483(9) -0.0311(4) 0.0775(7) Uani 1 1 d . . .
H9A H 0.2188 0.7085 0.0783 0.116 Uiso 1 1 calc R . .
H9B H 0.0234 0.6918 -0.0653 0.116 Uiso 1 1 calc R . .
H9C H 0.2168 0.7045 -0.1189 0.116 Uiso 1 1 calc R . .
C10 C 0.2873(2) 0.46810(8) 0.0464(2) 0.0433(4) Uani 1 1 d . . .
H10A H 0.3155 0.4994 0.1411 0.052 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 C2 1.322(2) . ?
O1 C1 1.441(2) . ?
O2 C2 1.205(2) . ?
O3 C8 1.196(2) . ?
O4 C8 1.333(2) . ?
O4 C9 1.436(2) . ?
N1 C5 1.378(2) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C2 C3 1.487(2) . ?
C3 C4 1.382(2) . ?
C3 C10 1.387(2) . ?
C4 C5 1.390(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.394(2) . ?
C6 C7 1.387(2) . ?
C6 H6A 0.9300 . ?
C7 C10 1.382(2) . ?
C7 C8 1.488(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9300 . ?

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
C2 O1 C1 117.33(15) . . ?
C8 O4 C9 116.97(16) . . ?
C5 N1 H1A 120.0 . . ?
C5 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
O1 C1 H1C 109.5 . . ?
O1 C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
O1 C1 H1E 109.5 . . ?
H1C C1 H1E 109.5 . . ?
H1D C1 H1E 109.5 . . ?
O2 C2 O1 123.46(16) . . ?
O2 C2 C3 123.90(16) . . ?
O1 C2 C3 112.62(14) . . ?
C4 C3 C10 120.45(15) . . ?
C4 C3 C2 117.82(14) . . ?
C10 C3 C2 121.73(15) . . ?
C3 C4 C5 121.12(15) . . ?
C3 C4 H4A 119.4 . . ?
C5 C4 H4A 119.4 . . ?
C6 C5 N1 121.54(16) . . ?
C6 C5 C4 118.16(15) . . ?
N1 C5 C4 120.29(16) . . ?
C7 C6 C5 120.56(15) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C6 C7 C10 120.82(14) . . ?
C6 C7 C8 117.64(15) . . ?
C10 C7 C8 121.54(15) . . ?
O3 C8 O4 123.35(16) . . ?
O3 C8 C7 124.56(17) . . ?
O4 C8 C7 112.09(15) . . ?
O4 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O4 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 C3 118.89(15) . . ?
C7 C10 H10A 120.6 . . ?
C3 C10 H10A 120.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 C2 O2 1.5(3) . . . . ?
C1 O1 C2 C3 -177.23(16) . . . . ?
O2 C2 C3 C4 -12.9(3) . . . . ?
O1 C2 C3 C4 165.82(14) . . . . ?
O2 C2 C3 C10 166.72(18) . . . . ?
O1 C2 C3 C10 -14.5(2) . . . . ?
C10 C3 C4 C5 0.1(2) . . . . ?
C2 C3 C4 C5 179.70(14) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C3 C4 C5 N1 -179.40(15) . . . . ?
N1 C5 C6 C7 179.26(16) . . . . ?
C4 C5 C6 C7 0.4(2) . . . . ?
C5 C6 C7 C10 0.2(2) . . . . ?
C5 C6 C7 C8 179.12(14) . . . . ?
C9 O4 C8 O3 -1.1(3) . . . . ?
C9 O4 C8 C7 178.50(15) . . . . ?
C6 C7 C8 O3 7.7(3) . . . . ?
C10 C7 C8 O3 -173.41(17) . . . . ?
C6 C7 C8 O4 -171.92(13) . . . . ?
C10 C7 C8 O4 7.0(2) . . . . ?
C6 C7 C10 C3 -0.6(2) . . . . ?
C8 C7 C10 C3 -179.50(14) . . . . ?
C4 C3 C10 C7 0.5(2) . . . . ?
C2 C3 C10 C7 -179.14(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.047
