# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_ste1511
_database_code_depnum_ccdc_archive 'CCDC 1529243'
_audit_update_record             
;
2017-01-23 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-Bromo 3-nitrobenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          472-479
_chemical_formula_moiety         'C7 H4 Br N O4'
_chemical_formula_sum            'C7 H4 Br N O4'
_chemical_formula_weight         246.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.4417(7)
_cell_length_b                   5.7471(6)
_cell_length_c                   18.9993(19)
_cell_angle_alpha                90
_cell_angle_beta                 101.045(5)
_cell_angle_gamma                90
_cell_volume                     797.51(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    8789
_cell_measurement_theta_min      4.4
_cell_measurement_theta_max      53.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.049
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    5.132
_shelx_estimated_absorpt_T_min   0.442
_shelx_estimated_absorpt_T_max   0.534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6691
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Sheldrick,2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker Nonius Apex II'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13038
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.793
_diffrn_reflns_theta_max         26.493
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1641
_reflns_number_gt                1538
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;

 The compound forms a carboxylic acid H-bond dimer with a short 
 O...O distance (2.631(2). A difference fourier map showed 
 density near each carboxyl oxygen so the final refinment model
 included an H atom with partial occupancy bonded to each 
 carboxyl oxygen. The O-H distances were restarined to be 0.9A, 
 The isotropic displacement parameters were constrained to be 
 the same. The relative occupancy (H1O:H4O) refined to 
 0.64(3):0.36(3).






;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0125P)²+0.7232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1641
_refine_ls_number_parameters     126
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0183
_refine_ls_R_factor_gt           0.0163
_refine_ls_wR_factor_ref         0.0384
_refine_ls_wR_factor_gt          0.0378
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.070
_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
C1 C 0.3871(2) 0.3371(3) 0.35314(8) 0.0167(3) Uani 1 1 d . . . . .
Br1 Br 0.20171(2) 0.12049(3) 0.31880(2) 0.02372(6) Uani 1 1 d . . . . .
C2 C 0.5644(2) 0.3176(3) 0.33958(8) 0.0162(3) Uani 1 1 d . . . . .
C3 C 0.7040(2) 0.4620(3) 0.37205(8) 0.0171(3) Uani 1 1 d . . . . .
H3 H 0.8251 0.4408 0.3641 0.021 Uiso 1 1 calc R U . . .
C4 C 0.6646(2) 0.6390(3) 0.41653(8) 0.0175(3) Uani 1 1 d . . . . .
C5 C 0.4862(2) 0.6675(3) 0.42780(9) 0.0197(3) Uani 1 1 d . . . . .
H5 H 0.4583 0.7923 0.4567 0.024 Uiso 1 1 calc R U . . .
C6 C 0.3497(2) 0.5152(3) 0.39716(9) 0.0198(3) Uani 1 1 d . . . . .
H6 H 0.2294 0.5330 0.4064 0.024 Uiso 1 1 calc R U . . .
N7 N 0.60865(19) 0.1467(2) 0.28801(8) 0.0197(3) Uani 1 1 d . . . . .
O1 O 0.50693(17) 0.1365(2) 0.22928(7) 0.0285(3) Uani 1 1 d . . . . .
O2 O 0.74764(18) 0.0304(2) 0.30595(7) 0.0312(3) Uani 1 1 d . . . . .
C8 C 0.8115(2) 0.7978(3) 0.45253(9) 0.0187(3) Uani 1 1 d . . . . .
O3 O 0.97563(17) 0.7481(2) 0.44695(7) 0.0285(3) Uani 1 1 d D . . . .
H3O H 1.045(4) 0.853(5) 0.4671(17) 0.034(9) Uiso 0.64(3) 1 d D . P A 2
O4 O 0.76928(17) 0.9687(2) 0.48681(7) 0.0287(3) Uani 1 1 d D . . . .
H4O H 0.858(6) 1.056(9) 0.508(3) 0.034(9) Uiso 0.36(3) 1 d D . P A 1


_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 C6 1.384(2) . ?
C1 C2 1.397(2) . ?
C1 Br1 1.8796(16) . ?
C2 C3 1.380(2) . ?
C2 N7 1.469(2) . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(2) . ?
C4 C8 1.486(2) . ?
C5 C6 1.382(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N7 O1 1.2238(19) . ?
N7 O2 1.2240(19) . ?
C8 O4 1.251(2) . ?
C8 O3 1.279(2) . ?
O3 H3O 0.838(19) . ?
O4 H4O 0.87(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
C6 C1 C2 118.49(15) . . ?
C6 C1 Br1 118.75(12) . . ?
C2 C1 Br1 122.64(12) . . ?
C3 C2 C1 121.76(15) . . ?
C3 C2 N7 117.05(14) . . ?
C1 C2 N7 121.15(14) . . ?
C2 C3 C4 118.95(15) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 H3 120.5 . . ?
C3 C4 C5 119.84(15) . . ?
C3 C4 C8 120.48(15) . . ?
C5 C4 C8 119.68(15) . . ?
C6 C5 C4 120.36(15) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.47(15) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
O1 N7 O2 124.72(14) . . ?
O1 N7 C2 117.51(14) . . ?
O2 N7 C2 117.72(14) . . ?
O4 C8 O3 123.89(16) . . ?
O4 C8 C4 119.07(15) . . ?
O3 C8 C4 117.04(15) . . ?
C8 O3 H3O 109(2) . . ?
C8 O4 H4O 117(4) . . ?

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
C6 C1 C2 C3 3.8(2) . . . . ?
Br1 C1 C2 C3 -172.25(13) . . . . ?
C6 C1 C2 N7 -174.09(15) . . . . ?
Br1 C1 C2 N7 9.9(2) . . . . ?
C1 C2 C3 C4 -3.4(2) . . . . ?
N7 C2 C3 C4 174.61(14) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C2 C3 C4 C8 179.90(15) . . . . ?
C3 C4 C5 C6 2.5(3) . . . . ?
C8 C4 C5 C6 -177.25(15) . . . . ?
C4 C5 C6 C1 -2.0(3) . . . . ?
C2 C1 C6 C5 -1.1(2) . . . . ?
Br1 C1 C6 C5 175.15(13) . . . . ?
C3 C2 N7 O1 -130.01(16) . . . . ?
C1 C2 N7 O1 48.0(2) . . . . ?
C3 C2 N7 O2 47.7(2) . . . . ?
C1 C2 N7 O2 -134.37(17) . . . . ?
C3 C4 C8 O4 173.35(16) . . . . ?
C5 C4 C8 O4 -6.9(2) . . . . ?
C3 C4 C8 O3 -7.4(2) . . . . ?
C5 C4 C8 O3 172.28(16) . . . . ?

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
C3 H3 O1 0.95 2.61 3.306(2) 130.1 2_655
C6 H6 O3 0.95 2.50 3.383(2) 154.7 1_455
O3 H3O O4 0.838(19) 1.80(2) 2.6307(18) 168(4) 3_776
O4 H4O O3 0.87(2) 1.77(2) 2.6307(18) 175(6) 3_776

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 'Evaporation '
####################################################################### 
# 
# 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_Ste168
_database_code_depnum_ccdc_archive 'CCDC 1529244'
_audit_update_record             
;
2017-01-23 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '4-Methyl 3-nitrobenzoic acid'
_chemical_name_common            ?
_chemical_melting_point          460-463
_chemical_formula_moiety         'C8 H7 N O4'
_chemical_formula_sum            'C8 H7 N O4'
_chemical_formula_weight         181.15

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.4313(3)
_cell_length_b                   21.1153(6)
_cell_length_c                   10.3853(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.9210(10)
_cell_angle_gamma                90
_cell_volume                     1605.23(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    9954
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      27.9

_exptl_crystal_description       'iregular prism'
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.123
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9630
_exptl_absorpt_correction_T_max  0.9680
_exptl_absorpt_process_details   'Apex-II SAD-ABS (Sheldrick, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker-Nonius Kappa Apex-II'
_diffrn_measurement_method       'CCD phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29640
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.772
_diffrn_reflns_theta_max         27.936
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3834
_reflns_number_gt                3173
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.

 The two independent molecules form a strong carboxylic acid hydrogen 
 bond dimer. The acid hydrogen atoms are disordered over two locations.
 The relative occupancies refined to 0.52(3):0.48(3) for the H8, H18 
 pair vs. the H7, H17 pair. The partial H atoms were freely refined
 with the O-H bonds restrained to be 0.85A.

 Both nitro groups exhibit rotational disorder. The relative 
 occupancies are 0.856(7):0.144(7) for N3,O3,O4 vs N3,O3',O4' with 
 a rotation of 30 degrees about the C3-N3 bond and 0.992(6):0.078(6)
 for C13,O13,O14 vs. N13,O13',O14' with a rotation of 33 degrees
 about the C13-N13 bond. The N(3;13)-O(3',4';13',14') bonds were 
 restarined to be the same as the N(3;13)-O(3,4;13,14) bonds,
 respectively. In addition the O(3,3')...O(4,4') and 
 O(13,13')...O(14,14') distances were restrained to be the same.
 The nitro groups were restrained to be planar. The O*' atoms were
 assigned isotropic displacement parameters equal to the U(iso,eq)
 of the O* atoms (eg,U(iso;O3')=U(Iso,equivalent;O3). The C3, N3,
 O3, O4, C13, N13, O13 and O14 anisotropic displacement 
 parameters were restrained with the rigid bond restraint.
 
;

_computing_data_collection       'APEX-II (Bruler-AXS, 2014)'

_computing_cell_refinement       'APEX-II (Bruler-AXS, 2014)'
_computing_data_reduction        'APEX-II (Bruler-AXS, 2014)'
_computing_structure_solution    'APEX-II (Bruler-AXS, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0565P)²+0.4914P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3834
_refine_ls_number_parameters     268
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.068
_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
C1 C 0.96579(16) 0.46459(5) 0.78774(11) 0.0219(2) Uani 1 1 d . . . . .
C2 C 0.95226(16) 0.43511(5) 0.90520(11) 0.0226(2) Uani 1 1 d . . . . .
H2 H 0.8427 0.4378 0.9404 0.027 Uiso 1 1 calc R U . . .
C3 C 1.10089(17) 0.40164(5) 0.97023(11) 0.0243(2) Uani 1 1 d . U . . .
N3 N 1.07107(16) 0.36839(6) 1.08923(11) 0.0344(3) Uani 1 1 d D U . . .
O3 O 1.1506(3) 0.31748(12) 1.1152(3) 0.0615(9) Uani 0.856(7) 1 d D U P A 1
O3' O 1.2059(13) 0.3428(7) 1.1567(11) 0.062 Uiso 0.144(7) 1 d D U P A 2
O4 O 0.9620(3) 0.39059(10) 1.1513(2) 0.0435(5) Uani 0.856(7) 1 d D U P A 1
O4' O 0.9331(13) 0.3807(8) 1.1338(15) 0.044 Uiso 0.144(7) 1 d D U P A 2
C4 C 1.26882(17) 0.39855(6) 0.92730(12) 0.0281(3) Uani 1 1 d . . . . .
C5 C 1.27662(18) 0.42930(6) 0.80913(13) 0.0319(3) Uani 1 1 d . . . . .
H5 H 1.3879 0.4285 0.7759 0.038 Uiso 1 1 calc R U . . .
C6 C 1.12821(17) 0.46088(6) 0.73879(12) 0.0275(3) Uani 1 1 d . . . . .
H6 H 1.1373 0.4800 0.6573 0.033 Uiso 1 1 calc R U . . .
C7 C 0.80738(16) 0.50067(5) 0.71755(11) 0.0230(2) Uani 1 1 d . . . . .
O7 O 0.67299(13) 0.50950(5) 0.77566(9) 0.0342(2) Uani 1 1 d D . . . .
H7 H 0.584(3) 0.5285(14) 0.734(3) 0.032(10) Uiso 0.48(3) 1 d D . P B 1
O8 O 0.81416(13) 0.52104(4) 0.60345(9) 0.0307(2) Uani 1 1 d D . . . .
H8 H 0.721(3) 0.5413(14) 0.568(3) 0.038(10) Uiso 0.52(3) 1 d D . P B 2
C8 C 1.4378(2) 0.36699(8) 1.00026(15) 0.0432(4) Uani 1 1 d . . . . .
H8A H 1.4550 0.3792 1.0926 0.065 Uiso 1 1 calc R U . . .
H8B H 1.5442 0.3804 0.9630 0.065 Uiso 1 1 calc R U . . .
H8C H 1.4242 0.3209 0.9927 0.065 Uiso 1 1 calc R U . . .
C11 C 0.24499(15) 0.63514(5) 0.47917(11) 0.0216(2) Uani 1 1 d . . . . .
C12 C 0.25197(16) 0.66499(5) 0.36138(11) 0.0221(2) Uani 1 1 d . . . . .
H12 H 0.3568 0.6610 0.3210 0.026 Uiso 1 1 calc R U . . .
C13 C 0.10295(16) 0.70087(5) 0.30317(11) 0.0236(2) Uani 1 1 d . U . . .
N13 N 0.12368(15) 0.73219(5) 0.18014(11) 0.0319(3) Uani 1 1 d D U . . .
O13 O 0.0424(3) 0.78231(10) 0.15207(19) 0.0528(6) Uani 0.922(6) 1 d D U P C 1
O13' O -0.0091(18) 0.7578(12) 0.1154(18) 0.053 Uiso 0.078(6) 1 d D U P C 2
O14 O 0.2233(3) 0.70762(8) 0.11238(16) 0.0404(4) Uani 0.922(6) 1 d D U P C 1
O14' O 0.2683(16) 0.7225(10) 0.1422(19) 0.040 Uiso 0.078(6) 1 d D U P C 2
C14 C -0.05679(17) 0.70724(6) 0.35603(12) 0.0269(3) Uani 1 1 d . . . . .
C15 C -0.05815(17) 0.67581(6) 0.47446(13) 0.0298(3) Uani 1 1 d . . . . .
H15 H -0.1641 0.6785 0.5139 0.036 Uiso 1 1 calc R U . . .
C16 C 0.08937(17) 0.64091(6) 0.53611(12) 0.0265(3) Uani 1 1 d . . . . .
H16 H 0.0845 0.6209 0.6173 0.032 Uiso 1 1 calc R U . . .
C17 C 0.40252(16) 0.59668(5) 0.54335(11) 0.0227(2) Uani 1 1 d . . . . .
O17 O 0.53394(13) 0.58714(5) 0.48245(9) 0.0320(2) Uani 1 1 d D . . . .
H17 H 0.620(3) 0.5657(14) 0.520(3) 0.029(10) Uiso 0.48(3) 1 d D . P B 1
O18 O 0.39626(13) 0.57481(5) 0.65614(9) 0.0341(2) Uani 1 1 d D . . . .
H18 H 0.491(3) 0.5555(15) 0.692(3) 0.047(11) Uiso 0.52(3) 1 d D . P B 2
C18 C -0.22415(19) 0.74351(7) 0.29447(15) 0.0395(3) Uani 1 1 d . . . . .
H18A H -0.2003 0.7891 0.3044 0.059 Uiso 1 1 calc R U . . .
H18B H -0.3270 0.7321 0.3376 0.059 Uiso 1 1 calc R U . . .
H18C H -0.2540 0.7329 0.2013 0.059 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
C1 C2 1.3886(16) . ?
C1 C6 1.3903(17) . ?
C1 C7 1.4838(16) . ?
C2 C3 1.3851(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3972(18) . ?
C3 N3 1.4710(16) . ?
N3 O4 1.2135(19) . ?
N3 O4' 1.223(8) . ?
N3 O3 1.2338(19) . ?
N3 O3' 1.243(7) . ?
C4 C5 1.3983(19) . ?
C4 C8 1.5057(18) . ?
C5 C6 1.3846(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 O7 1.2665(15) . ?
C7 O8 1.2697(14) . ?
O7 H7 0.830(18) . ?
O8 H8 0.841(18) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C11 C12 1.3850(16) . ?
C11 C16 1.3919(17) . ?
C11 C17 1.4850(16) . ?
C12 C13 1.3911(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3976(18) . ?
C13 N13 1.4701(16) . ?
N13 O13' 1.220(8) . ?
N13 O14 1.2213(16) . ?
N13 O14' 1.224(8) . ?
N13 O13 1.2286(16) . ?
C14 C15 1.3991(19) . ?
C14 C18 1.5060(17) . ?
C15 C16 1.3831(18) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 O18 1.2673(14) . ?
C17 O17 1.2678(15) . ?
O17 H17 0.827(18) . ?
O18 H18 0.843(19) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C2 C1 C6 119.66(11) . . ?
C2 C1 C7 119.37(10) . . ?
C6 C1 C7 120.97(10) . . ?
C3 C2 C1 119.00(11) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 123.31(11) . . ?
C2 C3 N3 115.49(11) . . ?
C4 C3 N3 121.20(11) . . ?
O4 N3 O3 123.99(15) . . ?
O4' N3 O3' 121.7(8) . . ?
O4 N3 C3 118.24(15) . . ?
O4' N3 C3 118.3(8) . . ?
O3 N3 C3 117.62(13) . . ?
O3' N3 C3 117.2(6) . . ?
C3 C4 C5 115.64(11) . . ?
C3 C4 C8 124.98(12) . . ?
C5 C4 C8 119.34(12) . . ?
C6 C5 C4 122.48(12) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C5 C6 C1 119.80(11) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
O7 C7 O8 123.79(11) . . ?
O7 C7 C1 117.74(10) . . ?
O8 C7 C1 118.47(10) . . ?
C7 O7 H7 116(2) . . ?
C7 O8 H8 115(2) . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C12 C11 C16 119.71(11) . . ?
C12 C11 C17 119.91(10) . . ?
C16 C11 C17 120.37(10) . . ?
C11 C12 C13 118.92(11) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C12 C13 C14 123.24(11) . . ?
C12 C13 N13 115.34(11) . . ?
C14 C13 N13 121.42(11) . . ?
O13' N13 O14' 124.6(10) . . ?
O14 N13 O13 123.44(12) . . ?
O13' N13 C13 118.9(8) . . ?
O14 N13 C13 118.32(11) . . ?
O14' N13 C13 115.7(9) . . ?
O13 N13 C13 118.22(12) . . ?
C13 C14 C15 115.78(11) . . ?
C13 C14 C18 125.27(12) . . ?
C15 C14 C18 118.94(12) . . ?
C16 C15 C14 122.31(12) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C15 C16 C11 120.02(11) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
O18 C17 O17 123.87(11) . . ?
O18 C17 C11 117.54(11) . . ?
O17 C17 C11 118.58(10) . . ?
C17 O17 H17 117(2) . . ?
C17 O18 H18 115(2) . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C6 C1 C2 C3 -1.01(17) . . . . ?
C7 C1 C2 C3 -179.87(10) . . . . ?
C1 C2 C3 C4 3.47(18) . . . . ?
C1 C2 C3 N3 -176.12(10) . . . . ?
C2 C3 N3 O4 -29.7(2) . . . . ?
C4 C3 N3 O4 150.75(17) . . . . ?
C2 C3 N3 O4' -11.9(9) . . . . ?
C4 C3 N3 O4' 168.5(9) . . . . ?
C2 C3 N3 O3 146.0(2) . . . . ?
C4 C3 N3 O3 -33.6(2) . . . . ?
C2 C3 N3 O3' -173.5(9) . . . . ?
C4 C3 N3 O3' 6.9(9) . . . . ?
C2 C3 C4 C5 -2.94(18) . . . . ?
N3 C3 C4 C5 176.62(11) . . . . ?
C2 C3 C4 C8 175.05(12) . . . . ?
N3 C3 C4 C8 -5.39(19) . . . . ?
C3 C4 C5 C6 0.05(19) . . . . ?
C8 C4 C5 C6 -178.06(13) . . . . ?
C4 C5 C6 C1 2.2(2) . . . . ?
C2 C1 C6 C5 -1.72(18) . . . . ?
C7 C1 C6 C5 177.11(11) . . . . ?
C2 C1 C7 O7 8.31(16) . . . . ?
C6 C1 C7 O7 -170.53(11) . . . . ?
C2 C1 C7 O8 -171.91(10) . . . . ?
C6 C1 C7 O8 9.25(16) . . . . ?
C16 C11 C12 C13 0.74(16) . . . . ?
C17 C11 C12 C13 -179.88(10) . . . . ?
C11 C12 C13 C14 -1.63(17) . . . . ?
C11 C12 C13 N13 178.51(10) . . . . ?
C12 C13 N13 O13' 170.9(15) . . . . ?
C14 C13 N13 O13' -8.9(15) . . . . ?
C12 C13 N13 O14 28.4(2) . . . . ?
C14 C13 N13 O14 -151.47(17) . . . . ?
C12 C13 N13 O14' 0.9(13) . . . . ?
C14 C13 N13 O14' -179.0(12) . . . . ?
C12 C13 N13 O13 -150.35(18) . . . . ?
C14 C13 N13 O13 29.8(2) . . . . ?
C12 C13 C14 C15 1.05(17) . . . . ?
N13 C13 C14 C15 -179.10(10) . . . . ?
C12 C13 C14 C18 -177.66(11) . . . . ?
N13 C13 C14 C18 2.19(18) . . . . ?
C13 C14 C15 C16 0.39(18) . . . . ?
C18 C14 C15 C16 179.18(12) . . . . ?
C14 C15 C16 C11 -1.22(19) . . . . ?
C12 C11 C16 C15 0.63(17) . . . . ?
C17 C11 C16 C15 -178.75(11) . . . . ?
C12 C11 C17 O18 174.08(10) . . . . ?
C16 C11 C17 O18 -6.54(16) . . . . ?
C12 C11 C17 O17 -6.51(16) . . . . ?
C16 C11 C17 O17 172.87(11) . . . . ?

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
O7 H7 O18 0.830(18) 1.779(19) 2.6061(13) 175(3) .
O8 H8 O17 0.841(18) 1.800(19) 2.6385(13) 175(3) .
O17 H17 O8 0.827(18) 1.812(18) 2.6385(13) 178(3) .
O18 H18 O7 0.843(19) 1.767(19) 2.6061(13) 173(4) .

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.046

