# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ORL_PABA0.46_PHBA0.54

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16.50 Cl N3.50 O5.50'
_chemical_formula_weight         357.26

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   7.0287(5)
_cell_length_b                   15.0835(11)
_cell_length_c                   14.7528(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.090(6)
_cell_angle_gamma                90.00
_cell_volume                     1564.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light red'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9206
_exptl_absorpt_correction_T_max  0.9460
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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  ?
_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            7417
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2957
_reflns_number_gt                2261
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0742P)²+1.1826P] 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       ?
_refine_ls_number_reflns         2957
_refine_ls_number_parameters     224
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1651
_refine_ls_wR_factor_gt          0.1524
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.052
_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
Cl1 Cl 0.05689(11) 0.75048(6) 0.55020(6) 0.0288(3) Uani 1 1 d . . .
O3 O 0.3347(3) 0.70105(14) 0.31908(15) 0.0245(5) Uani 1 1 d . . .
H3 H 0.3672 0.7340 0.2777 0.037 Uiso 1 1 calc R . .
N2 N 0.1789(3) 0.92011(17) 0.13655(18) 0.0202(6) Uani 1 1 d . . .
O4 O -0.2403(3) 0.52637(16) 0.47159(16) 0.0292(6) Uani 1 1 d . . .
H4 H -0.2681 0.5545 0.5172 0.044 Uiso 1 1 calc R . .
O1 O 0.1252(4) 0.94185(17) 0.43903(16) 0.0340(6) Uani 1 1 d . . .
O5 O -0.3403(3) 0.65089(15) 0.40420(16) 0.0279(6) Uani 1 1 d . . .
N3 N 0.1138(3) 0.85667(16) 0.26865(18) 0.0181(6) Uani 1 1 d . . .
C2 C 0.2044(4) 0.9821(2) 0.2031(2) 0.0220(7) Uani 1 1 d . . .
H2 H 0.2426 1.0405 0.1940 0.026 Uiso 1 1 calc R . .
O2 O 0.2317(4) 1.06179(16) 0.37428(18) 0.0379(7) Uani 1 1 d . . .
C1 C 0.1647(4) 0.9445(2) 0.2844(2) 0.0191(7) Uani 1 1 d . . .
N1 N 0.1739(4) 0.98448(18) 0.3713(2) 0.0244(6) Uani 1 1 d . . .
C8 C -0.2767(4) 0.5746(2) 0.3993(2) 0.0212(7) Uani 1 1 d . . .
C6 C 0.2292(4) 0.7498(2) 0.3839(2) 0.0213(7) Uani 1 1 d . . .
H6 H 0.3081 0.7980 0.4080 0.026 Uiso 1 1 calc R . .
C3 C 0.1256(4) 0.8457(2) 0.1780(2) 0.0188(7) Uani 1 1 d . . .
C10 C -0.1714(4) 0.4420(2) 0.3105(2) 0.0243(8) Uani 1 1 d . . .
H10 H -0.1528 0.4116 0.3646 0.029 Uiso 1 1 calc R . .
C7 C 0.1684(5) 0.6892(2) 0.4609(2) 0.0257(8) Uani 1 1 d . . .
H7A H 0.2789 0.6585 0.4847 0.031 Uiso 1 1 calc R . .
H7B H 0.0803 0.6451 0.4379 0.031 Uiso 1 1 calc R . .
C14 C -0.2545(4) 0.5748(2) 0.2300(2) 0.0233(7) Uani 1 1 d . . .
H14 H -0.2935 0.6337 0.2301 0.028 Uiso 1 1 calc R . .
C13 C -0.2199(4) 0.5332(2) 0.1483(2) 0.0278(8) Uani 1 1 d . A .
H13 H -0.2333 0.5643 0.0942 0.033 Uiso 1 1 calc R . .
C4 C 0.0782(5) 0.7617(2) 0.1301(2) 0.0247(7) Uani 1 1 d . . .
H4A H 0.0433 0.7174 0.1737 0.037 Uiso 1 1 calc R . .
H4B H 0.1870 0.7419 0.0965 0.037 Uiso 1 1 calc R . .
H4C H -0.0261 0.7718 0.0893 0.037 Uiso 1 1 calc R . .
C5 C 0.0569(4) 0.7887(2) 0.3352(2) 0.0216(7) Uani 1 1 d . . .
H5A H -0.0114 0.7416 0.3044 0.026 Uiso 1 1 calc R . .
H5B H -0.0282 0.8150 0.3793 0.026 Uiso 1 1 calc R . .
C9 C -0.2323(4) 0.5304(2) 0.3126(2) 0.0231(7) Uani 1 1 d . . .
C11 C -0.1388(4) 0.3996(2) 0.2294(2) 0.0270(8) Uani 1 1 d . A .
H11 H -0.0991 0.3408 0.2293 0.032 Uiso 1 1 calc R . .
C12 C -0.1647(4) 0.4440(2) 0.1471(2) 0.0268(8) Uani 1 1 d . . .
O6 O -0.1311(4) 0.4002(2) 0.06741(19) 0.0342(11) Uani 0.53(5) 1 d P A 1
H6B H -0.1515 0.4336 0.0246 0.051 Uiso 0.53(5) 1 calc PR A 1
N10 N -0.1311(4) 0.4002(2) 0.06741(19) 0.0342(11) Uani 0.47(5) 1 d PD A 2
H6C H -0.132(11) 0.3427(14) 0.069(5) 0.041 Uiso 0.47(5) 1 d PD A 2
H10B H -0.197(11) 0.425(4) 0.025(4) 0.041 Uiso 0.47(5) 1 d PD A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.791(3) . ?
O3 C6 1.417(4) . ?
N2 C3 1.332(4) . ?
N2 C2 1.367(4) . ?
O4 C8 1.316(4) . ?
O1 N1 1.237(4) . ?
O5 C8 1.237(4) . ?
N3 C3 1.351(4) . ?
N3 C1 1.392(4) . ?
N3 C5 1.475(4) . ?
C2 C1 1.356(4) . ?
O2 N1 1.236(4) . ?
C1 N1 1.418(4) . ?
C8 C9 1.476(4) . ?
C6 C7 1.521(4) . ?
C6 C5 1.525(4) . ?
C3 C4 1.487(4) . ?
C10 C11 1.377(5) . ?
C10 C9 1.400(5) . ?
C14 C13 1.381(5) . ?
C14 C9 1.400(5) . ?
C13 C12 1.399(5) . ?
C11 C12 1.399(5) . ?
C12 O6 1.369(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N2 C2 106.5(3) . . ?
C3 N3 C1 105.4(3) . . ?
C3 N3 C5 126.3(3) . . ?
C1 N3 C5 128.4(3) . . ?
C1 C2 N2 108.8(3) . . ?
C2 C1 N3 107.7(3) . . ?
C2 C1 N1 127.8(3) . . ?
N3 C1 N1 124.5(3) . . ?
O2 N1 O1 123.6(3) . . ?
O2 N1 C1 116.6(3) . . ?
O1 N1 C1 119.8(3) . . ?
O5 C8 O4 122.4(3) . . ?
O5 C8 C9 123.2(3) . . ?
O4 C8 C9 114.3(3) . . ?
O3 C6 C7 109.9(2) . . ?
O3 C6 C5 107.3(3) . . ?
C7 C6 C5 111.1(3) . . ?
N2 C3 N3 111.6(3) . . ?
N2 C3 C4 124.3(3) . . ?
N3 C3 C4 124.1(3) . . ?
C11 C10 C9 120.9(3) . . ?
C6 C7 Cl1 111.3(2) . . ?
C13 C14 C9 121.5(3) . . ?
C14 C13 C12 119.8(3) . . ?
N3 C5 C6 111.4(2) . . ?
C14 C9 C10 118.0(3) . . ?
C14 C9 C8 121.0(3) . . ?
C10 C9 C8 121.0(3) . . ?
C10 C11 C12 120.6(3) . . ?
O6 C12 C11 119.4(3) . . ?
O6 C12 C13 121.5(3) . . ?
C11 C12 C13 119.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.960
_refine_diff_density_max         0.625
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.074
_database_code_depnum_ccdc_archive 'CCDC 1014220'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ORL_PABA

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H17 Cl N4 O5'
_chemical_formula_weight         356.77

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'
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'
N N 0.0061 0.0033 '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/n

loop_
_symmetry_equiv_pos_as_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                   7.1364(4)
_cell_length_b                   14.8900(9)
_cell_length_c                   14.8390(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.636(5)
_cell_angle_gamma                90.00
_cell_volume                     1576.16(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9216
_exptl_absorpt_correction_T_max  0.9467
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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  ?
_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            13240
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3098
_reflns_number_gt                2386
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0281P)²+1.1822P] 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       ?
_refine_ls_number_reflns         3098
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
Cl1 Cl 0.54430(9) 0.74813(5) 0.54629(4) 0.02698(19) Uani 1 1 d . . .
O2 O 0.6277(3) 0.94575(12) 0.43629(11) 0.0262(4) Uani 1 1 d . . .
O4 O 0.2539(3) 0.53241(13) 0.47376(12) 0.0272(5) Uani 1 1 d . . .
O5 O 0.1507(2) 0.65710(12) 0.40428(11) 0.0260(4) Uani 1 1 d . . .
N2 N 0.6743(3) 0.91802(14) 0.13685(13) 0.0191(5) Uani 1 1 d . . .
N3 N 0.6057(3) 0.85720(13) 0.26831(12) 0.0155(4) Uani 1 1 d . . .
O1 O 0.7325(3) 1.06517(13) 0.37085(12) 0.0334(5) Uani 1 1 d . . .
O3 O 0.8197(3) 0.70093(12) 0.32050(11) 0.0262(4) Uani 1 1 d . . .
N1 N 0.6749(3) 0.98733(14) 0.36874(14) 0.0207(5) Uani 1 1 d . . .
N4 N 0.3712(3) 0.40035(17) 0.07398(14) 0.0306(6) Uani 1 1 d . . .
H4D H 0.3467 0.3440 0.0797 0.037 Uiso 1 1 d R . .
H4E H 0.3019 0.4224 0.0310 0.037 Uiso 1 1 d R . .
C9 C 0.2627(3) 0.53484(17) 0.31609(15) 0.0191(5) Uani 1 1 d . . .
C2 C 0.7043(3) 0.98119(17) 0.20200(16) 0.0192(5) Uani 1 1 d . . .
H2 H 0.7461 1.0395 0.1926 0.023 Uiso 1 1 calc R . .
C1 C 0.6627(3) 0.94490(16) 0.28313(15) 0.0164(5) Uani 1 1 d . . .
C4 C 0.5632(4) 0.75935(17) 0.13121(16) 0.0241(6) Uani 1 1 d . . .
H4A H 0.4309 0.7492 0.1356 0.036 Uiso 1 1 calc R . .
H4B H 0.6306 0.7102 0.1587 0.036 Uiso 1 1 calc R . .
H4C H 0.5947 0.7638 0.0689 0.036 Uiso 1 1 calc R . .
C6 C 0.7175(3) 0.74949(17) 0.38409(16) 0.0204(6) Uani 1 1 d . . .
H6 H 0.7959 0.7978 0.4095 0.025 Uiso 1 1 calc R . .
C11 C 0.3629(3) 0.40213(19) 0.23700(16) 0.0235(6) Uani 1 1 d . . .
H11 H 0.4053 0.3431 0.2387 0.028 Uiso 1 1 calc R . .
C7 C 0.6586(4) 0.68672(18) 0.45930(16) 0.0230(6) Uani 1 1 d . . .
H7A H 0.7683 0.6565 0.4848 0.028 Uiso 1 1 calc R . .
H7B H 0.5740 0.6413 0.4348 0.028 Uiso 1 1 calc R . .
C8 C 0.2168(3) 0.58083(18) 0.40109(16) 0.0204(6) Uani 1 1 d . . .
C3 C 0.6148(3) 0.84421(16) 0.17833(15) 0.0176(5) Uani 1 1 d . . .
C14 C 0.2372(3) 0.57837(18) 0.23274(16) 0.0221(6) Uani 1 1 d . . .
H14 H 0.1958 0.6376 0.2312 0.027 Uiso 1 1 calc R . .
C5 C 0.5489(3) 0.78977(17) 0.33433(15) 0.0190(5) Uani 1 1 d . . .
H5A H 0.4791 0.7424 0.3036 0.023 Uiso 1 1 calc R . .
H5B H 0.4671 0.8175 0.3774 0.023 Uiso 1 1 calc R . .
C12 C 0.3342(3) 0.44547(19) 0.15369(16) 0.0231(6) Uani 1 1 d . . .
C10 C 0.3285(3) 0.44675(17) 0.31632(16) 0.0208(6) Uani 1 1 d . . .
H10 H 0.3497 0.4174 0.3710 0.025 Uiso 1 1 calc R . .
C13 C 0.2725(4) 0.53464(19) 0.15322(16) 0.0238(6) Uani 1 1 d . . .
H13 H 0.2551 0.5647 0.0987 0.029 Uiso 1 1 calc R . .
H3 H 0.948(6) 0.692(3) 0.351(3) 0.099(15) Uiso 1 1 d . . .
H4 H 0.223(5) 0.560(2) 0.526(2) 0.073(13) 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
Cl1 C7 1.797(3) . ?
O2 N1 1.233(3) . ?
O4 C8 1.318(3) . ?
O5 C8 1.231(3) . ?
N2 C3 1.335(3) . ?
N2 C2 1.361(3) . ?
N3 C3 1.353(3) . ?
N3 C1 1.384(3) . ?
N3 C5 1.468(3) . ?
O1 N1 1.230(3) . ?
O3 C6 1.409(3) . ?
N1 C1 1.419(3) . ?
N4 C12 1.392(3) . ?
C9 C10 1.393(4) . ?
C9 C14 1.404(3) . ?
C9 C8 1.480(3) . ?
C2 C1 1.360(3) . ?
C4 C3 1.485(3) . ?
C6 C5 1.517(3) . ?
C6 C7 1.524(3) . ?
C11 C10 1.380(3) . ?
C11 C12 1.404(3) . ?
C14 C13 1.377(3) . ?
C12 C13 1.399(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N2 C2 106.68(19) . . ?
C3 N3 C1 105.65(19) . . ?
C3 N3 C5 125.7(2) . . ?
C1 N3 C5 128.68(19) . . ?
O1 N1 O2 123.5(2) . . ?
O1 N1 C1 117.0(2) . . ?
O2 N1 C1 119.5(2) . . ?
C10 C9 C14 118.2(2) . . ?
C10 C9 C8 121.1(2) . . ?
C14 C9 C8 120.7(2) . . ?
C1 C2 N2 108.7(2) . . ?
C2 C1 N3 107.7(2) . . ?
C2 C1 N1 127.3(2) . . ?
N3 C1 N1 124.9(2) . . ?
O3 C6 C5 107.19(19) . . ?
O3 C6 C7 109.5(2) . . ?
C5 C6 C7 111.6(2) . . ?
C10 C11 C12 120.3(2) . . ?
C6 C7 Cl1 110.75(18) . . ?
O5 C8 O4 122.8(2) . . ?
O5 C8 C9 123.6(2) . . ?
O4 C8 C9 113.6(2) . . ?
N2 C3 N3 111.2(2) . . ?
N2 C3 C4 124.1(2) . . ?
N3 C3 C4 124.6(2) . . ?
C13 C14 C9 120.9(2) . . ?
N3 C5 C6 111.4(2) . . ?
N4 C12 C13 121.4(2) . . ?
N4 C12 C11 120.0(2) . . ?
C13 C12 C11 118.6(2) . . ?
C11 C10 C9 121.3(2) . . ?
C14 C13 C12 120.7(2) . . ?

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
C3 N2 C2 C1 0.1(3) . . . . ?
N2 C2 C1 N3 0.0(3) . . . . ?
N2 C2 C1 N1 179.8(2) . . . . ?
C3 N3 C1 C2 -0.2(3) . . . . ?
C5 N3 C1 C2 179.0(2) . . . . ?
C3 N3 C1 N1 -179.9(2) . . . . ?
C5 N3 C1 N1 -0.7(4) . . . . ?
O1 N1 C1 C2 -1.4(4) . . . . ?
O2 N1 C1 C2 178.3(2) . . . . ?
O1 N1 C1 N3 178.3(2) . . . . ?
O2 N1 C1 N3 -2.0(3) . . . . ?
O3 C6 C7 Cl1 175.34(17) . . . . ?
C5 C6 C7 Cl1 -66.1(2) . . . . ?
C10 C9 C8 O5 -176.7(2) . . . . ?
C14 C9 C8 O5 1.9(4) . . . . ?
C10 C9 C8 O4 3.4(3) . . . . ?
C14 C9 C8 O4 -177.9(2) . . . . ?
C2 N2 C3 N3 -0.2(3) . . . . ?
C2 N2 C3 C4 179.1(2) . . . . ?
C1 N3 C3 N2 0.2(3) . . . . ?
C5 N3 C3 N2 -179.0(2) . . . . ?
C1 N3 C3 C4 -179.0(2) . . . . ?
C5 N3 C3 C4 1.7(4) . . . . ?
C10 C9 C14 C13 1.3(4) . . . . ?
C8 C9 C14 C13 -177.3(2) . . . . ?
C3 N3 C5 C6 101.6(3) . . . . ?
C1 N3 C5 C6 -77.5(3) . . . . ?
O3 C6 C5 N3 -66.0(3) . . . . ?
C7 C6 C5 N3 174.1(2) . . . . ?
C10 C11 C12 N4 179.3(2) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C12 C11 C10 C9 0.8(4) . . . . ?
C14 C9 C10 C11 -1.8(4) . . . . ?
C8 C9 C10 C11 176.8(2) . . . . ?
C9 C14 C13 C12 0.2(4) . . . . ?
N4 C12 C13 C14 -179.8(2) . . . . ?
C11 C12 C13 C14 -1.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.062
_database_code_depnum_ccdc_archive 'CCDC 1020267'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ORL_PHBA

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Cl N3 O6'
_chemical_formula_weight         357.75

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   6.9766(3)
_cell_length_b                   15.2461(8)
_cell_length_c                   14.6100(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.602(4)
_cell_angle_gamma                90.00
_cell_volume                     1553.40(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9196
_exptl_absorpt_correction_T_max  0.9454
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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  ?
_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            12961
_diffrn_reflns_av_R_equivalents  0.0958
_diffrn_reflns_av_sigmaI/netI    0.0843
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3056
_reflns_number_gt                2029
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0759P)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_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3056
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0966
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_ref         0.1765
_refine_ls_wR_factor_gt          0.1481
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
Cl1 Cl 0.56516(12) 0.25125(6) -0.05388(6) 0.0376(3) Uani 1 1 d . . .
O4 O 0.2366(4) 0.52191(15) 0.46892(15) 0.0369(6) Uani 1 1 d . . .
H4 H 0.2674 0.5489 0.5156 0.055 Uiso 1 1 calc R . .
O5 O 0.3411(3) 0.64530(15) 0.40357(15) 0.0363(6) Uani 1 1 d . . .
O3 O 0.8389(3) 0.20054(16) 0.18494(16) 0.0341(6) Uani 1 1 d . . .
O6 O 0.1293(4) 0.39940(18) 0.05974(17) 0.0404(7) Uani 1 1 d . . .
N2 N 0.6837(4) 0.42014(17) 0.36438(18) 0.0275(6) Uani 1 1 d . . .
O2 O 0.7346(4) 0.55512(17) 0.12093(17) 0.0448(7) Uani 1 1 d . . .
N1 N 0.6716(4) 0.4790(2) 0.12668(19) 0.0343(7) Uani 1 1 d . . .
O1 O 0.6160(4) 0.43646(17) 0.05871(16) 0.0461(7) Uani 1 1 d . . .
C1 C 0.6629(4) 0.4409(2) 0.2144(2) 0.0275(7) Uani 1 1 d . . .
C2 C 0.7045(4) 0.4798(2) 0.2960(2) 0.0307(8) Uani 1 1 d . . .
H2 H 0.7413 0.5380 0.3040 0.037 Uiso 1 1 calc R . .
N3 N 0.6144(3) 0.35449(17) 0.23093(18) 0.0276(6) Uani 1 1 d . . .
C3 C 0.6285(4) 0.3451(2) 0.3230(2) 0.0280(7) Uani 1 1 d . . .
C9 C 0.2303(4) 0.5263(2) 0.3081(2) 0.0270(7) Uani 1 1 d . . .
C11 C 0.1383(4) 0.3975(2) 0.2206(2) 0.0323(8) Uani 1 1 d . . .
H11 H 0.1002 0.3391 0.2185 0.039 Uiso 1 1 calc R . .
C8 C 0.2748(4) 0.5698(2) 0.3967(2) 0.0299(8) Uani 1 1 d . . .
C5 C 0.5593(4) 0.2857(2) 0.1653(2) 0.0308(8) Uani 1 1 d . . .
H5A H 0.4688 0.3094 0.1202 0.037 Uiso 1 1 calc R . .
H5B H 0.4962 0.2385 0.1973 0.037 Uiso 1 1 calc R . .
C10 C 0.1716(4) 0.4387(2) 0.3043(2) 0.0289(8) Uani 1 1 d . . .
H10 H 0.1547 0.4077 0.3583 0.035 Uiso 1 1 calc R . .
C12 C 0.1624(4) 0.4443(2) 0.1397(2) 0.0318(8) Uani 1 1 d . . .
C6 C 0.7339(5) 0.2490(2) 0.1165(2) 0.0350(9) Uani 1 1 d . . .
H6 H 0.8127 0.2973 0.0943 0.042 Uiso 1 1 calc R . .
C4 C 0.5874(5) 0.2623(2) 0.3730(2) 0.0332(8) Uani 1 1 d . . .
H4A H 0.6153 0.2704 0.4372 0.050 Uiso 1 1 calc R . .
H4B H 0.6658 0.2159 0.3501 0.050 Uiso 1 1 calc R . .
H4C H 0.4546 0.2473 0.3640 0.050 Uiso 1 1 calc R . .
C14 C 0.2530(4) 0.5729(2) 0.2270(2) 0.0307(8) Uani 1 1 d . . .
H14 H 0.2918 0.6312 0.2290 0.037 Uiso 1 1 calc R . .
C13 C 0.2173(4) 0.5316(2) 0.1423(2) 0.0326(8) Uani 1 1 d . . .
H13 H 0.2304 0.5628 0.0882 0.039 Uiso 1 1 calc R . .
C7 C 0.6746(5) 0.1903(2) 0.0379(2) 0.0397(9) Uani 1 1 d . . .
H7A H 0.5850 0.1466 0.0591 0.048 Uiso 1 1 calc R . .
H7B H 0.7864 0.1599 0.0159 0.048 Uiso 1 1 calc R . .
H6A H 0.190(7) 0.425(4) 0.020(3) 0.090(19) Uiso 1 1 d . . .
H3 H 0.938(5) 0.185(2) 0.161(2) 0.024(9) 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
Cl1 C7 1.786(4) . ?
O4 C8 1.317(4) . ?
O5 C8 1.243(4) . ?
O3 C6 1.429(4) . ?
O6 C12 1.368(4) . ?
N2 C3 1.345(4) . ?
N2 C2 1.363(4) . ?
O2 N1 1.244(4) . ?
N1 O1 1.239(4) . ?
N1 C1 1.410(4) . ?
C1 C2 1.355(4) . ?
C1 N3 1.383(4) . ?
N3 C3 1.353(4) . ?
N3 C5 1.465(4) . ?
C3 C4 1.491(4) . ?
C9 C14 1.394(4) . ?
C9 C10 1.398(4) . ?
C9 C8 1.480(4) . ?
C11 C10 1.388(5) . ?
C11 C12 1.395(5) . ?
C5 C6 1.535(4) . ?
C12 C13 1.386(5) . ?
C6 C7 1.504(5) . ?
C14 C13 1.404(5) . ?

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
C3 N2 C2 105.8(3) . . ?
O1 N1 O2 122.5(3) . . ?
O1 N1 C1 119.4(3) . . ?
O2 N1 C1 118.0(3) . . ?
C2 C1 N3 108.1(3) . . ?
C2 C1 N1 127.2(3) . . ?
N3 C1 N1 124.6(3) . . ?
C1 C2 N2 109.1(3) . . ?
C3 N3 C1 105.2(3) . . ?
C3 N3 C5 125.8(3) . . ?
C1 N3 C5 129.0(3) . . ?
N2 C3 N3 111.7(3) . . ?
N2 C3 C4 123.8(3) . . ?
N3 C3 C4 124.5(3) . . ?
C14 C9 C10 119.6(3) . . ?
C14 C9 C8 119.2(3) . . ?
C10 C9 C8 121.2(3) . . ?
C10 C11 C12 119.7(3) . . ?
O5 C8 O4 122.2(3) . . ?
O5 C8 C9 123.7(3) . . ?
O4 C8 C9 114.2(3) . . ?
N3 C5 C6 111.6(3) . . ?
C11 C10 C9 120.6(3) . . ?
O6 C12 C13 123.0(3) . . ?
O6 C12 C11 116.5(3) . . ?
C13 C12 C11 120.5(3) . . ?
O3 C6 C7 110.6(3) . . ?
O3 C6 C5 105.1(3) . . ?
C7 C6 C5 111.5(3) . . ?
C9 C14 C13 119.9(3) . . ?
C12 C13 C14 119.8(3) . . ?
C6 C7 Cl1 111.5(3) . . ?

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
O1 N1 C1 C2 -175.0(3) . . . . ?
O2 N1 C1 C2 4.6(5) . . . . ?
O1 N1 C1 N3 7.0(5) . . . . ?
O2 N1 C1 N3 -173.4(3) . . . . ?
N3 C1 C2 N2 0.0(4) . . . . ?
N1 C1 C2 N2 -178.2(3) . . . . ?
C3 N2 C2 C1 -0.3(3) . . . . ?
C2 C1 N3 C3 0.2(3) . . . . ?
N1 C1 N3 C3 178.5(3) . . . . ?
C2 C1 N3 C5 -179.7(3) . . . . ?
N1 C1 N3 C5 -1.4(5) . . . . ?
C2 N2 C3 N3 0.4(3) . . . . ?
C2 N2 C3 C4 -179.4(3) . . . . ?
C1 N3 C3 N2 -0.4(3) . . . . ?
C5 N3 C3 N2 179.5(3) . . . . ?
C1 N3 C3 C4 179.4(3) . . . . ?
C5 N3 C3 C4 -0.7(5) . . . . ?
C14 C9 C8 O5 -3.6(5) . . . . ?
C10 C9 C8 O5 174.4(3) . . . . ?
C14 C9 C8 O4 175.8(3) . . . . ?
C10 C9 C8 O4 -6.2(4) . . . . ?
C3 N3 C5 C6 -103.2(4) . . . . ?
C1 N3 C5 C6 76.7(4) . . . . ?
C12 C11 C10 C9 -0.4(5) . . . . ?
C14 C9 C10 C11 0.8(5) . . . . ?
C8 C9 C10 C11 -177.2(3) . . . . ?
C10 C11 C12 O6 179.3(3) . . . . ?
C10 C11 C12 C13 -0.7(5) . . . . ?
N3 C5 C6 O3 70.2(3) . . . . ?
N3 C5 C6 C7 -169.9(3) . . . . ?
C10 C9 C14 C13 -0.1(5) . . . . ?
C8 C9 C14 C13 178.0(3) . . . . ?
O6 C12 C13 C14 -178.5(3) . . . . ?
C11 C12 C13 C14 1.4(5) . . . . ?
C9 C14 C13 C12 -1.0(5) . . . . ?
O3 C6 C7 Cl1 -173.9(2) . . . . ?
C5 C6 C7 Cl1 69.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.077
_database_code_depnum_ccdc_archive 'CCDC 1020268'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ORL_PABA0.33_PHBA0.67

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16.25 Cl N3.25 O5.75'
_chemical_formula_weight         357.50

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'
Cl Cl 0.1484 0.1585 '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/n

loop_
_symmetry_equiv_pos_as_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                   7.0625(9)
_cell_length_b                   15.0679(19)
_cell_length_c                   14.7835(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.563(9)
_cell_angle_gamma                90.00
_cell_volume                     1573.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            'light red'
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9208
_exptl_absorpt_correction_T_max  0.9462
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      120(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  ?
_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            7606
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_sigmaI/netI    0.0551
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.70
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2931
_reflns_number_gt                2278
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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)+(0.0626P)²+1.4386P] 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       ?
_refine_ls_number_reflns         2931
_refine_ls_number_parameters     224
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1351
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
Cl1 Cl 0.55227(11) 0.25034(5) 0.54897(5) 0.0290(2) Uani 1 1 d . . .
O4 O 0.2576(3) 0.47164(15) 0.47202(14) 0.0298(6) Uani 1 1 d . . .
H4 H 0.2304 0.4438 0.5177 0.045 Uiso 1 1 calc R . .
O5 O 0.1553(3) 0.34686(15) 0.40485(14) 0.0292(5) Uani 1 1 d . . .
O3 O 0.8279(3) 0.29854(15) 0.31899(14) 0.0273(5) Uani 1 1 d . . .
H3 H 0.9219 0.3206 0.3430 0.041 Uiso 1 1 calc R . .
O1 O 0.6259(3) 0.05673(15) 0.43787(14) 0.0306(6) Uani 1 1 d . . .
O2 O 0.7318(3) -0.06285(16) 0.37338(16) 0.0371(6) Uani 1 1 d . . .
N2 N 0.6774(3) 0.08076(17) 0.13672(16) 0.0204(6) Uani 1 1 d . . .
N1 N 0.6743(3) 0.01453(17) 0.37050(17) 0.0233(6) Uani 1 1 d . . .
N3 N 0.6107(3) 0.14293(16) 0.26890(15) 0.0174(5) Uani 1 1 d . . .
C1 C 0.6641(4) 0.05531(19) 0.28399(19) 0.0180(6) Uani 1 1 d . . .
C2 C 0.7050(4) 0.0186(2) 0.2032(2) 0.0210(7) Uani 1 1 d . . .
H2 H 0.7453 -0.0394 0.1942 0.025 Uiso 1 1 calc R . .
C8 C 0.2204(4) 0.4231(2) 0.40034(19) 0.0232(7) Uani 1 1 d . . .
C12 C 0.3342(4) 0.5552(2) 0.1493(2) 0.0273(8) Uani 1 1 d . . .
C3 C 0.6215(4) 0.1551(2) 0.17822(19) 0.0191(6) Uani 1 1 d . . .
C6 C 0.7256(4) 0.2499(2) 0.3839(2) 0.0240(7) Uani 1 1 d . . .
H6 H 0.8046 0.2020 0.4084 0.029 Uiso 1 1 calc R . .
C4 C 0.5746(5) 0.2394(2) 0.1306(2) 0.0256(7) Uani 1 1 d . . .
H4A H 0.5377 0.2833 0.1741 0.038 Uiso 1 1 calc R . .
H4B H 0.4722 0.2293 0.0887 0.038 Uiso 1 1 calc R . .
H4C H 0.6836 0.2599 0.0984 0.038 Uiso 1 1 calc R . .
C10 C 0.3287(4) 0.5563(2) 0.3123(2) 0.0231(7) Uani 1 1 d . . .
H10 H 0.3489 0.5862 0.3666 0.028 Uiso 1 1 calc R . .
C5 C 0.5535(4) 0.2110(2) 0.33468(19) 0.0219(7) Uani 1 1 d . . .
H5A H 0.4686 0.1848 0.3784 0.026 Uiso 1 1 calc R . .
H5B H 0.4857 0.2580 0.3035 0.026 Uiso 1 1 calc R . .
C11 C 0.3618(4) 0.5996(2) 0.2315(2) 0.0264(7) Uani 1 1 d . . .
H11 H 0.4025 0.6583 0.2318 0.032 Uiso 1 1 calc R . .
C7 C 0.6654(5) 0.3119(2) 0.4600(2) 0.0276(7) Uani 1 1 d . . .
H7A H 0.5784 0.3561 0.4362 0.033 Uiso 1 1 calc R . .
H7B H 0.7756 0.3424 0.4842 0.033 Uiso 1 1 calc R . .
C13 C 0.2765(4) 0.4661(2) 0.1500(2) 0.0267(7) Uani 1 1 d . . .
H13 H 0.2617 0.4354 0.0959 0.032 Uiso 1 1 calc R . .
C9 C 0.2651(4) 0.4679(2) 0.31382(19) 0.0215(7) Uani 1 1 d . . .
C14 C 0.2417(4) 0.4239(2) 0.2313(2) 0.0246(7) Uani 1 1 d . . .
H14 H 0.2019 0.3651 0.2309 0.030 Uiso 1 1 calc R . .
O6 O 0.3692(4) 0.5994(2) 0.06938(17) 0.0359(11) Uani 0.37(4) 1 d P . .
H6A H 0.3478 0.5662 0.0265 0.054 Uiso 0.37(4) 1 calc PR . .
N14 N 0.3692(4) 0.5994(2) 0.06938(17) 0.0359(11) Uani 0.63(4) 1 d PD . .
H6B H 0.375(8) 0.6574(14) 0.074(4) 0.043 Uiso 0.63(4) 1 d PD . .
H6C H 0.299(7) 0.582(4) 0.024(3) 0.043 Uiso 0.63(4) 1 d PD . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.803(3) . ?
O4 C8 1.312(4) . ?
O5 C8 1.239(4) . ?
O3 C6 1.412(3) . ?
O1 N1 1.233(3) . ?
O2 N1 1.235(3) . ?
N2 C3 1.339(4) . ?
N2 C2 1.370(4) . ?
N1 C1 1.420(4) . ?
N3 C3 1.356(4) . ?
N3 C1 1.390(4) . ?
N3 C5 1.472(3) . ?
C1 C2 1.350(4) . ?
C8 C9 1.483(4) . ?
C12 O6 1.381(4) . ?
C12 C11 1.399(4) . ?
C12 C13 1.404(5) . ?
C3 C4 1.488(4) . ?
C6 C5 1.528(4) . ?
C6 C7 1.525(4) . ?
C10 C11 1.382(4) . ?
C10 C9 1.407(4) . ?
C13 C14 1.383(4) . ?
C9 C14 1.397(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N2 C2 106.5(2) . . ?
O1 N1 O2 123.5(3) . . ?
O1 N1 C1 119.5(3) . . ?
O2 N1 C1 117.0(2) . . ?
C3 N3 C1 105.6(2) . . ?
C3 N3 C5 125.3(2) . . ?
C1 N3 C5 129.1(2) . . ?
C2 C1 N3 107.9(2) . . ?
C2 C1 N1 127.6(3) . . ?
N3 C1 N1 124.5(2) . . ?
C1 C2 N2 108.9(3) . . ?
O5 C8 O4 123.0(3) . . ?
O5 C8 C9 123.4(3) . . ?
O4 C8 C9 113.6(3) . . ?
O6 C12 C11 119.2(3) . . ?
O6 C12 C13 121.5(3) . . ?
C11 C12 C13 119.2(3) . . ?
N2 C3 N3 111.1(3) . . ?
N2 C3 C4 124.3(3) . . ?
N3 C3 C4 124.6(3) . . ?
O3 C6 C5 106.6(2) . . ?
O3 C6 C7 109.4(2) . . ?
C5 C6 C7 111.1(2) . . ?
C11 C10 C9 121.2(3) . . ?
N3 C5 C6 111.1(2) . . ?
C10 C11 C12 120.1(3) . . ?
C6 C7 Cl1 110.6(2) . . ?
C14 C13 C12 120.1(3) . . ?
C14 C9 C10 118.1(3) . . ?
C14 C9 C8 120.8(3) . . ?
C10 C9 C8 121.1(3) . . ?
C13 C14 C9 121.3(3) . . ?

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
C3 N3 C1 C2 0.2(3) . . . . ?
C5 N3 C1 C2 -179.8(3) . . . . ?
C3 N3 C1 N1 179.4(3) . . . . ?
C5 N3 C1 N1 -0.5(5) . . . . ?
O1 N1 C1 C2 -177.7(3) . . . . ?
O2 N1 C1 C2 2.0(5) . . . . ?
O1 N1 C1 N3 3.3(4) . . . . ?
O2 N1 C1 N3 -177.0(3) . . . . ?
N3 C1 C2 N2 -0.5(3) . . . . ?
N1 C1 C2 N2 -179.7(3) . . . . ?
C3 N2 C2 C1 0.6(3) . . . . ?
C2 N2 C3 N3 -0.5(3) . . . . ?
C2 N2 C3 C4 -179.5(3) . . . . ?
C1 N3 C3 N2 0.2(3) . . . . ?
C5 N3 C3 N2 -179.9(2) . . . . ?
C1 N3 C3 C4 179.2(3) . . . . ?
C5 N3 C3 C4 -0.8(4) . . . . ?
C3 N3 C5 C6 -102.0(3) . . . . ?
C1 N3 C5 C6 77.9(4) . . . . ?
O3 C6 C5 N3 67.9(3) . . . . ?
C7 C6 C5 N3 -173.0(2) . . . . ?
C9 C10 C11 C12 -0.7(5) . . . . ?
O6 C12 C11 C10 -179.6(3) . . . . ?
C13 C12 C11 C10 -1.3(5) . . . . ?
O3 C6 C7 Cl1 -175.0(2) . . . . ?
C5 C6 C7 Cl1 67.6(3) . . . . ?
O6 C12 C13 C14 -179.7(3) . . . . ?
C11 C12 C13 C14 2.1(4) . . . . ?
C11 C10 C9 C14 1.9(4) . . . . ?
C11 C10 C9 C8 -176.9(3) . . . . ?
O5 C8 C9 C14 -2.4(5) . . . . ?
O4 C8 C9 C14 177.2(3) . . . . ?
O5 C8 C9 C10 176.4(3) . . . . ?
O4 C8 C9 C10 -4.0(4) . . . . ?
C12 C13 C14 C9 -0.8(4) . . . . ?
C10 C9 C14 C13 -1.1(4) . . . . ?
C8 C9 C14 C13 177.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.945
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.945
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.066
_database_code_depnum_ccdc_archive 'CCDC 1020269'
