Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Scott Childs'
_publ_contact_author_address     
;
SSCI, Inc.
3065 Kent Ave.
West Lafayette
IN
47906
UNITED STATES OF AMERICA
;

_publ_contact_author_email       SCOTT.CHILDS@APTUIT.COM

_publ_section_title              
;
Cocrystals of chlorzoxazone with carboxylic acids
;
_publ_author_name                'Scott Childs'

data_a13g120
_database_code_depnum_ccdc_archive 'CCDC 638925'

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;

5-Chloro-2(3H)-benzoxazolone 2,4-dihydroxybenzoic acid

;

_chemical_name_common            
'5-Chloro-2(3H)-benzoxazolone 2,4-dihydroxybenzoic acid'

_chemical_melting_point          452.3

_chemical_formula_moiety         'C7 H4 Cl N O2, C7 H6 O4'

_chemical_formula_sum            'C14 H10 Cl N O6'

_chemical_formula_weight         323.68

loop_

_atom_type_symbol

_atom_type_description

_atom_type_scat_dispersion_real

_atom_type_scat_dispersion_imag

_atom_type_scat_source

C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic

_symmetry_space_group_name_H-M   P-1

loop_

_symmetry_equiv_pos_as_xyz

'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7431(5)

_cell_length_b                   8.0503(6)

_cell_length_c                   13.8001(10)

_cell_angle_alpha                77.722(3)

_cell_angle_beta                 88.476(2)

_cell_angle_gamma                66.354(2)

_cell_volume                     669.09(9)

_cell_formula_units_Z            2

_cell_measurement_temperature    173(2)

_cell_measurement_reflns_used    1206

_cell_measurement_theta_min      3.26

_cell_measurement_theta_max      66.81

_exptl_crystal_description       rhomboid

_exptl_crystal_colour            colorless

_exptl_crystal_size_max          0.18

_exptl_crystal_size_mid          0.15

_exptl_crystal_size_min          0.10

_exptl_crystal_density_meas      0

_exptl_crystal_density_diffrn    1.607

_exptl_crystal_density_method    'not measured'

_exptl_crystal_F_000             332

_exptl_absorpt_coefficient_mu    2.840

_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.6289

_exptl_absorpt_correction_T_max  0.7643

_exptl_absorpt_process_details   'SADABS V2.10, Sheldrick 2003'

_exptl_special_details           
;

?

;

_diffrn_ambient_temperature      173(2)

_diffrn_radiation_wavelength     1.54178

_diffrn_radiation_type           CuK\a

_diffrn_radiation_source         'fine-focus sealed tube'

_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean ?

_diffrn_standards_number         ?

_diffrn_standards_interval_count ?

_diffrn_standards_interval_time  ?

_diffrn_standards_decay_%        ?

_diffrn_reflns_number            3349

_diffrn_reflns_av_R_equivalents  0.0211

_diffrn_reflns_av_sigmaI/netI    0.0315

_diffrn_reflns_limit_h_min       -8

_diffrn_reflns_limit_h_max       7

_diffrn_reflns_limit_k_min       -8

_diffrn_reflns_limit_k_max       9

_diffrn_reflns_limit_l_min       -14

_diffrn_reflns_limit_l_max       16

_diffrn_reflns_theta_min         3.28

_diffrn_reflns_theta_max         67.05

_reflns_number_total             2014

_reflns_number_gt                1801

_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'

_computing_cell_refinement       'Bruker SMART'

_computing_data_reduction        'Bruker SAINT'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'Bruker SHELXTL'

_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;

Refinement of F^2^ against ALL reflections. The weighted R-factor wR and

goodness of fit S are based on F^2^, conventional R-factors R are based

on F, with F set to zero for negative F^2^. The threshold expression of

F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F^2^ 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/[\s^2^(Fo^2^)+(0.0523P)^2^+0.3796P] where P=(Fo^2^+2Fc^2^)/3'

_atom_sites_solution_primary     direct

_atom_sites_solution_secondary   difmap

_atom_sites_solution_hydrogens   geom

_refine_ls_hydrogen_treatment    constr

_refine_ls_extinction_method     none

_refine_ls_extinction_coef       ?

_refine_ls_number_reflns         2014

_refine_ls_number_parameters     199

_refine_ls_number_restraints     0

_refine_ls_R_factor_all          0.0465

_refine_ls_R_factor_gt           0.0413

_refine_ls_wR_factor_ref         0.1023

_refine_ls_wR_factor_gt          0.0991

_refine_ls_goodness_of_fit_ref   1.067

_refine_ls_restrained_S_all      1.067

_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_symmetry_multiplicity

_atom_site_calc_flag

_atom_site_refinement_flags

_atom_site_disorder_assembly

_atom_site_disorder_group

C1 C 1.0240(4) 0.3811(3) 0.92023(17) 0.0275(5) Uani 1 1 d . . .
C2 C 0.7486(4) 0.5270(3) 0.80295(16) 0.0243(5) Uani 1 1 d . . .
C3 C 0.5632(4) 0.5881(3) 0.74138(17) 0.0271(5) Uani 1 1 d . . .
H3 H 0.4515 0.5453 0.7573 0.033 Uiso 1 1 calc R . .
C4 C 0.5525(4) 0.7173(3) 0.65423(17) 0.0270(5) Uani 1 1 d . . .
C5 C 0.7103(4) 0.7852(3) 0.63074(17) 0.0302(5) Uani 1 1 d . . .
H5 H 0.6926 0.8753 0.5710 0.036 Uiso 1 1 calc R . .
C6 C 0.8949(4) 0.7225(3) 0.69394(18) 0.0305(5) Uani 1 1 d . . .
H6 H 1.0045 0.7684 0.6796 0.037 Uiso 1 1 calc R . .
C7 C 0.9100(4) 0.5909(3) 0.77795(17) 0.0261(5) Uani 1 1 d . . .
C8 C 0.5983(4) 0.8753(3) 0.24492(16) 0.0241(5) Uani 1 1 d . . .
C9 C 0.5200(4) 1.0048(3) 0.15586(17) 0.0261(5) Uani 1 1 d . . .
H9 H 0.3814 1.0310 0.1269 0.031 Uiso 1 1 calc R . .
C10 C 0.6436(4) 1.0954(3) 0.10945(17) 0.0259(5) Uani 1 1 d . . .
C11 C 0.8486(4) 1.0585(3) 0.14986(18) 0.0285(5) Uani 1 1 d . . .
H11 H 0.9322 1.1221 0.1172 0.034 Uiso 1 1 calc R . .
C12 C 0.9276(4) 0.9284(3) 0.23785(17) 0.0267(5) Uani 1 1 d . . .
H12 H 1.0676 0.9015 0.2654 0.032 Uiso 1 1 calc R . .
C13 C 0.8051(4) 0.8351(3) 0.28737(16) 0.0239(5) Uani 1 1 d . . .
C14 C 0.8876(4) 0.6962(3) 0.38054(16) 0.0252(5) Uani 1 1 d . . .
Cl1 Cl 0.33357(10) 0.79217(9) 0.56769(4) 0.0382(2) Uani 1 1 d . . .
N1 N 0.8239(3) 0.3978(3) 0.89305(14) 0.0266(4) Uani 1 1 d . . .
H1 H 0.7526 0.3365 0.9270 0.032 Uiso 1 1 calc R . .
O1 O 1.0802(2) 0.5000(2) 0.84980(11) 0.0297(4) Uani 1 1 d . . .
O2 O 1.1432(3) 0.2829(2) 0.99297(12) 0.0334(4) Uani 1 1 d . . .
O3 O 0.4691(3) 0.7921(2) 0.28728(13) 0.0359(4) Uani 1 1 d . . .
O4 O 0.5709(3) 1.2255(2) 0.02234(12) 0.0336(4) Uani 1 1 d . . .
O5 O 0.7832(3) 0.6090(2) 0.42390(12) 0.0305(4) Uani 1 1 d . . .
O6 O 1.0802(3) 0.6694(2) 0.41549(12) 0.0325(4) Uani 1 1 d . . .
H4O H 0.4465 1.2436 0.0085 0.039 Uiso 1 1 d R . .
H3O H 0.5444 0.7107 0.3431 0.039 Uiso 1 1 d R . .
H6O H 1.1195 0.5786 0.4665 0.039 Uiso 1 1 d R . .

loop_

_atom_site_aniso_label

_atom_site_aniso_U_11

_atom_site_aniso_U_22

_atom_site_aniso_U_33

_atom_site_aniso_U_23

_atom_site_aniso_U_13

_atom_site_aniso_U_12

C1 0.0279(13) 0.0279(12) 0.0255(13) -0.0068(10) 0.0037(10) -0.0098(11)
C2 0.0255(12) 0.0235(11) 0.0229(12) -0.0040(9) 0.0033(9) -0.0094(10)
C3 0.0275(12) 0.0295(12) 0.0268(13) -0.0056(10) 0.0042(9) -0.0145(10)
C4 0.0276(13) 0.0279(12) 0.0235(12) -0.0054(10) 0.0005(9) -0.0092(10)
C5 0.0368(14) 0.0283(12) 0.0238(13) 0.0015(10) 0.0040(10) -0.0151(11)
C6 0.0314(13) 0.0330(13) 0.0310(14) -0.0050(11) 0.0056(10) -0.0184(11)
C7 0.0233(12) 0.0265(12) 0.0281(13) -0.0076(10) 0.0008(9) -0.0087(10)
C8 0.0245(12) 0.0228(11) 0.0264(12) -0.0050(9) 0.0030(9) -0.0110(10)
C9 0.0226(12) 0.0253(11) 0.0280(13) -0.0032(10) -0.0048(9) -0.0081(10)
C10 0.0278(13) 0.0242(11) 0.0222(12) -0.0017(9) 0.0002(9) -0.0085(10)
C11 0.0257(12) 0.0283(12) 0.0312(13) -0.0006(10) 0.0022(9) -0.0134(11)
C12 0.0236(12) 0.0284(12) 0.0278(13) -0.0046(10) -0.0007(9) -0.0107(10)
C13 0.0237(12) 0.0215(11) 0.0248(12) -0.0046(9) 0.0009(9) -0.0076(10)
C14 0.0251(12) 0.0247(11) 0.0235(12) -0.0058(9) 0.0005(9) -0.0075(10)
Cl1 0.0361(4) 0.0490(4) 0.0275(4) 0.0041(3) -0.0051(2) -0.0211(3)
N1 0.0267(10) 0.0269(10) 0.0249(10) 0.0002(8) 0.0023(8) -0.0123(9)
O1 0.0259(9) 0.0348(9) 0.0288(9) -0.0055(7) 0.0014(7) -0.0133(8)
O2 0.0296(9) 0.0363(9) 0.0279(10) -0.0012(8) -0.0044(7) -0.0094(8)
O3 0.0303(9) 0.0393(10) 0.0362(10) 0.0078(8) -0.0060(7) -0.0197(8)
O4 0.0281(9) 0.0372(10) 0.0288(9) 0.0084(7) -0.0054(7) -0.0139(8)
O5 0.0279(9) 0.0322(9) 0.0281(9) 0.0028(7) -0.0004(7) -0.0134(8)
O6 0.0291(9) 0.0349(9) 0.0274(9) 0.0081(7) -0.0090(7) -0.0137(8)

_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 O2 1.214(3) . ?
C1 N1 1.356(3) . ?
C1 O1 1.371(3) . ?
C2 C3 1.383(3) . ?
C2 C7 1.386(3) . ?
C2 N1 1.395(3) . ?
C3 C4 1.395(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 Cl1 1.744(2) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.369(3) . ?
C6 H6 0.9500 . ?
C7 O1 1.383(3) . ?
C8 O3 1.350(3) . ?
C8 C9 1.387(3) . ?
C8 C13 1.412(3) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9500 . ?
C10 O4 1.366(3) . ?
C10 C11 1.397(3) . ?
C11 C12 1.379(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.401(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.463(3) . ?
C14 O5 1.241(3) . ?
C14 O6 1.316(3) . ?
N1 H1 0.8800 . ?
O3 H3O 0.9053 . ?
O4 H4O 0.8123 . ?
O6 H6O 0.8580 . ?

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

O2 C1 N1 129.5(2) . . ?
O2 C1 O1 122.0(2) . . ?
N1 C1 O1 108.45(19) . . ?
C3 C2 C7 121.4(2) . . ?
C3 C2 N1 133.0(2) . . ?
C7 C2 N1 105.5(2) . . ?
C2 C3 C4 115.0(2) . . ?
C2 C3 H3 122.5 . . ?
C4 C3 H3 122.5 . . ?
C5 C4 C3 123.5(2) . . ?
C5 C4 Cl1 117.75(18) . . ?
C3 C4 Cl1 118.70(18) . . ?
C4 C5 C6 120.5(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 116.3(2) . . ?
C7 C6 H6 121.8 . . ?
C5 C6 H6 121.8 . . ?
C6 C7 O1 127.7(2) . . ?
C6 C7 C2 123.2(2) . . ?
O1 C7 C2 109.1(2) . . ?
O3 C8 C9 117.1(2) . . ?
O3 C8 C13 122.8(2) . . ?
C9 C8 C13 120.1(2) . . ?
C10 C9 C8 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
O4 C10 C9 121.5(2) . . ?
O4 C10 C11 117.2(2) . . ?
C9 C10 C11 121.3(2) . . ?
C12 C11 C10 119.0(2) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 121.1(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C12 C13 C8 118.7(2) . . ?
C12 C13 C14 121.7(2) . . ?
C8 C13 C14 119.6(2) . . ?
O5 C14 O6 122.1(2) . . ?
O5 C14 C13 122.4(2) . . ?
O6 C14 C13 115.6(2) . . ?
C1 N1 C2 109.52(19) . . ?
C1 N1 H1 125.2 . . ?
C2 N1 H1 125.2 . . ?
C1 O1 C7 107.41(17) . . ?
C8 O3 H3O 106.0 . . ?
C10 O4 H4O 109.1 . . ?
C14 O6 H6O 108.5 . . ?

loop_

_geom_hbond_atom_site_label_D

_geom_hbond_atom_site_label_H

_geom_hbond_atom_site_label_A

_geom_hbond_distance_DH

_geom_hbond_distance_HA

_geom_hbond_distance_DA

_geom_hbond_angle_DHA

_geom_hbond_site_symmetry_A

O6 H6O O5 0.86 1.81 2.669(2) 176.3 2_766
O3 H3O O5 0.91 1.78 2.596(2) 149.2 .
O4 H4O O2 0.81 1.95 2.759(2) 172.8 1_464
N1 H1 O4 0.88 2.08 2.950(2) 170.1 1_546

_diffrn_measured_fraction_theta_max 0.843

_diffrn_reflns_theta_full        67.05

_diffrn_measured_fraction_theta_full 0.843

_refine_diff_density_max         0.241

_refine_diff_density_min         -0.362

_refine_diff_density_rms         0.092


