# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_3-asa
_database_code_depnum_ccdc_archive 'CCDC 1056289'
_audit_update_record             
;
2015-04-17 deposited with the CCDC.
2015-06-02 downloaded from the CCDC.
;
_audit_creation_date             2015-04-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C7 H7 N O3'
_chemical_formula_sum            'C7 H7 N O3'
_chemical_formula_weight         153.14
_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 0.0181 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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.2375(9)
_cell_length_b                   4.5168(5)
_cell_length_c                   14.7924(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.394(8)
_cell_angle_gamma                90
_cell_volume                     652.73(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.949
_exptl_absorpt_coefficient_mu    1.053
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku/MSC Inc., 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3676
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         67.731
_diffrn_reflns_theta_min         6.548
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku R-Axis Rapid'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                646
_reflns_number_total             1174
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0699
_refine_ls_restrained_S_all      1.016
_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)+(0.1279P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.2300
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All N(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.0949(2) 0.2721(5) 0.23869(17) 0.0386(8) Uani 1 1 d . . . . .
H1 H 0.075(4) 0.164(9) 0.292(3) 0.058 Uiso 1 1 d R . . . .
O2 O 0.1034(2) 0.1566(5) 0.40895(16) 0.0409(8) Uani 1 1 d . . . . .
O3 O 0.2481(3) 0.3976(5) 0.53059(16) 0.0421(8) Uani 1 1 d . . . . .
N1 N 0.1792(3) 0.5963(7) 0.1135(2) 0.0363(8) Uani 1 1 d . . . . .
H1A H 0.205(4) 0.777(9) 0.082(2) 0.054 Uiso 1 1 d R . . . .
H1B H 0.201(4) 0.406(8) 0.091(2) 0.054 Uiso 1 1 d R . . . .
H1C H 0.089(4) 0.605(8) 0.104(3) 0.054 Uiso 1 1 d R . . . .
C2 C 0.1978(3) 0.4627(7) 0.2769(2) 0.0317(9) Uani 1 1 d . . . . .
C3 C 0.2567(4) 0.5009(7) 0.3747(2) 0.0325(9) Uani 1 1 d . . . . .
C7 C 0.1997(4) 0.3442(7) 0.4430(3) 0.0349(9) Uani 1 1 d . . . . .
C1 C 0.2478(4) 0.6276(7) 0.2144(2) 0.0331(9) Uani 1 1 d . . . . .
C4 C 0.3669(3) 0.6969(8) 0.4066(2) 0.0364(9) Uani 1 1 d . . . . .
H4 H 0.4071 0.7247 0.4727 0.044 Uiso 1 1 calc R . . . .
C6 C 0.3567(3) 0.8198(8) 0.2473(3) 0.0369(9) Uani 1 1 d . . . . .
H6 H 0.3893 0.9308 0.2040 0.044 Uiso 1 1 calc R . . . .
C5 C 0.4183(4) 0.8502(8) 0.3443(3) 0.0396(10) Uani 1 1 d . . . . .
H5 H 0.4955 0.9760 0.3675 0.048 Uiso 1 1 calc 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
O1 0.0401(15) 0.0376(15) 0.0367(15) 0.0002(12) 0.0092(12) -0.0077(12)
O2 0.0354(15) 0.0429(16) 0.0435(16) 0.0028(11) 0.0105(12) -0.0028(12)
O3 0.0499(17) 0.0419(15) 0.0314(14) -0.0014(11) 0.0074(12) 0.0010(13)
N1 0.0360(18) 0.0337(17) 0.0363(18) -0.0005(14) 0.0062(15) 0.0004(15)
C2 0.0328(19) 0.0254(17) 0.0349(19) -0.0009(14) 0.0070(15) 0.0028(15)
C3 0.038(2) 0.0274(18) 0.0322(19) 0.0024(15) 0.0102(15) 0.0034(16)
C7 0.037(2) 0.0282(18) 0.041(2) 0.0049(16) 0.0141(17) 0.0072(16)
C1 0.036(2) 0.0318(17) 0.0304(19) 0.0018(15) 0.0083(15) 0.0041(17)
C4 0.038(2) 0.0333(19) 0.035(2) -0.0013(15) 0.0067(17) 0.0027(16)
C6 0.035(2) 0.035(2) 0.041(2) 0.0028(16) 0.0120(17) 0.0034(17)
C5 0.034(2) 0.0346(19) 0.047(2) -0.0004(17) 0.0081(18) -0.0006(17)

_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 H1 1.00(4) . ?
O1 C2 1.347(4) . ?
O2 C7 1.283(4) . ?
O3 C7 1.264(4) . ?
N1 H1A 1.02(4) . ?
N1 H1B 0.98(4) . ?
N1 H1C 0.89(4) . ?
N1 C1 1.454(4) . ?
C2 C3 1.402(4) . ?
C2 C1 1.399(5) . ?
C3 C7 1.487(4) . ?
C3 C4 1.400(5) . ?
C1 C6 1.381(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.390(4) . ?
C5 H5 0.9500 . ?

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 H1 108(2) . . ?
H1A N1 H1B 115(3) . . ?
H1A N1 H1C 107(3) . . ?
H1B N1 H1C 109(3) . . ?
C1 N1 H1A 107(2) . . ?
C1 N1 H1B 110(2) . . ?
C1 N1 H1C 109(2) . . ?
O1 C2 C3 123.5(3) . . ?
O1 C2 C1 117.3(3) . . ?
C1 C2 C3 119.2(3) . . ?
C2 C3 C7 120.5(3) . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 C7 120.8(3) . . ?
O2 C7 C3 117.3(3) . . ?
O3 C7 O2 123.2(3) . . ?
O3 C7 C3 119.5(3) . . ?
C2 C1 N1 117.8(3) . . ?
C6 C1 N1 121.0(3) . . ?
C6 C1 C2 121.2(3) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.6(3) . . ?
C5 C4 H4 119.2 . . ?
C1 C6 H6 120.1 . . ?
C1 C6 C5 119.7(3) . . ?
C5 C6 H6 120.1 . . ?
C4 C5 C6 119.6(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?

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
O1 H1 O2 1.00(4) 1.67(4) 2.548(3) 144(3) .
N1 H1A O3 1.02(4) 1.77(4) 2.783(4) 177(3) 4_575
N1 H1B O3 0.98(4) 1.78(4) 2.738(4) 168(3) 4_565
N1 H1C O2 0.89(4) 1.94(4) 2.825(4) 174(4) 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
O1 C2 C3 C7 -4.7(5) . . . . ?
O1 C2 C3 C4 177.5(3) . . . . ?
O1 C2 C1 N1 4.2(4) . . . . ?
O1 C2 C1 C6 -177.5(3) . . . . ?
N1 C1 C6 C5 178.5(3) . . . . ?
C2 C3 C7 O2 5.7(5) . . . . ?
C2 C3 C7 O3 -175.0(3) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C2 C1 C6 C5 0.2(5) . . . . ?
C3 C2 C1 N1 -176.3(3) . . . . ?
C3 C2 C1 C6 2.0(5) . . . . ?
C3 C4 C5 C6 2.5(5) . . . . ?
C7 C3 C4 C5 -178.1(3) . . . . ?
C1 C2 C3 C7 175.9(3) . . . . ?
C1 C2 C3 C4 -2.0(5) . . . . ?
C1 C6 C5 C4 -2.5(5) . . . . ?
C4 C3 C7 O2 -176.5(3) . . . . ?
C4 C3 C7 O3 2.7(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
