# Supplementary Material (ESI) for Chemical Communications
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               Chem.Commun.

_journal_coden_Cambridge         0182

_publ_contact_author_name        'Konstantin Lyssenko'
_publ_contact_author_email       KOSTYA@XRAY.INEOS.AC.RU

_publ_section_title              
;
"Higher density does not mean higher stability"
mystery of paracetamol finally unraveled
;
loop_
_publ_author_name
'Konstantin Lyssenko'
'Mikhail Yu. Antipin'
'Ivan V. Glukhov'
'Yulia V. Nelyubina'

# Attachment '1_xd.cif'

#\#CIF_1.1

# Archive CIF produced by XD routine XDCIF
# Created on 30-Mar-03 at 13:36:56
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:/xd2006/lib/xd/xdcif.dat
# CIF files read : geo lsm

data_1
_database_code_depnum_ccdc_archive 'CCDC 754966'
#TrackingRef '1_xd.cif'

_audit_creation_date             '30-Mar-03 T13:36:56-00:00'
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 1/2+X,1/2-Y,1/2+Z

_cell_length_a                   7.09070(10)
_cell_length_b                   9.2114(2)
_cell_length_c                   11.5972(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.8440(10)
_cell_angle_gamma                90
_cell_volume                     750.39(2)

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.974
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(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  'Bruker SMART APEX2 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            101813
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.83
_diffrn_reflns_theta_max         57.50
_reflns_number_total             10480
_reflns_number_gt                7259
_reflns_threshold_expression     I>2/s(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w1 = [Fo*sqrt(w2) + sqrt(Fo^2^w2^2^ + sqrt(w2^2^))]^2^
where
calc w2 = q/[s^2^(Fo^2^) + (0.02 P)^2^ + 0.10 P + 0.00 + 0.00 sin(th)]
where P = (0.3333 Fo^2^ + 0.6667 Fc^2^)
q = 1.0
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6223
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.028
_refine_ls_R_factor_gt           0.021
_refine_ls_wR_factor_ref         0.02
_refine_ls_goodness_of_fit_ref   1.23
_refine_ls_shift/su_max          0.00001

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O(1) 0.164108 0.423144 0.722518 0.016 1 4
O(2) 0.353304 -0.005776 0.30867 0.018 1 4
N(1) 0.051951 0.051419 0.339618 0.012 1 4
C(1) 0.133909 0.330882 0.629685 0.012 1 4
C(2) 0.280547 0.237026 0.609871 0.013 1 4
C(3) 0.258218 0.142794 0.51487 0.012 1 4
C(4) 0.088138 0.142651 0.438241 0.01 1 4
C(5) -0.059824 0.234803 0.45961 0.014 1 4
C(6) -0.037688 0.32841 0.554601 0.014 1 4
C(7) 0.178601 -0.014147 0.280446 0.012 1 4
C(8) 0.092659 -0.101168 0.176134 0.018 1 4
H(1O) 0.042152 0.459645 0.743809 0.038 1 4
H(1N) -0.088776 0.04089 0.309859 0.023 1 4
H(2) 0.410395 0.234969 0.670548 0.02 1 4
H(3) 0.369271 0.066676 0.501941 0.022 1 4
H(5) -0.191387 0.232059 0.40049 0.03 1 4
H(6) -0.155287 0.3976 0.568845 0.023 1 4
H(8B) 0.173773 -0.085357 0.104794 0.039 1 4
H(8C) 0.105698 -0.216229 0.193279 0.049 1 4
H(8A) -0.058113 -0.082279 0.153177 0.047 1 4

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
O(1) 0.010992 0.020589 0.017038 -0.006874 -0.000156 0.000913
O(2) 0.010507 0.026688 0.016981 -0.001342 0.004071 0.002486
N(1) 0.009069 0.013932 0.012245 -0.001315 0.001606 0.000683
C(1) 0.009563 0.013426 0.012413 -0.001175 0.000388 0.000696
C(2) 0.009283 0.015699 0.013008 -0.001049 -0.000417 0.001675
C(3) 0.009038 0.01435 0.012883 -0.000443 0.000325 0.002302
C(4) 0.008713 0.011778 0.010781 0.000399 0.001099 0.001042
C(5) 0.009807 0.016465 0.014044 -0.002951 -0.001212 0.003486
C(6) 0.010521 0.016613 0.015361 -0.003863 -0.00103 0.003753
C(7) 0.011352 0.013625 0.012557 -0.000088 0.003381 0.000959
C(8) 0.019458 0.018666 0.017163 -0.00514 0.00502 -0.001278

#----------------------------------------------------------------------------#
# MULTIPOLE PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
O(1) 6.1315 0 0.007(4) -0.089(4) -0.036(5) -0.015(5) 0.018(5) 0.059(5) 0.041(5)
0.011(5) 0.078(6) 0.016(6) -0.015(6) 0.057(6) 0.006(6) 0.000(6) -0.009(6) 0 0 0
0 0 0 0 0 0 1.001331 0.913997 0.913997 0.913997 0.913997 0.913997 2 4.466 2
4.466 2 4.466 3 4.466 4 4.466
O(2) 6.1669 0 -0.032(5) -0.007(4) -0.074(4) -0.007(5) -0.009(5) -0.008(5)
-0.088(5) 0.012(5) 0.005(7) -0.022(7) -0.004(6) 0.009(6) -0.018(6) -0.003(6)
0.005(6) 0 0 0 0 0 0 0 0 0 0.998756 0.93599 0.93599 0.93599 0.93599 0.93599 2
4.466 2 4.466 2 4.466 3 4.466 4 4.466
N(1) 5.1143 0 -0.013(5) 0.034(5) 0.030(5) 0.035(5) 0.021(5) -0.004(5) -0.001(5)
0.005(5) 0.159(6) 0.017(6) 0.046(7) 0.101(6) 0.011(6) -0.006(6) 0.022(6) 0 0 0
0 0 0 0 0 0 1.003199 0.977205 0.977205 0.977205 0.977205 0.977205 2 3.83936 2
3.83936 2 3.83936 3 3.83936 4 3.83936
C(1) 4.1113 0 0.044(7) 0.067(7) 0 -0.203(7) 0 0 0.028(7) -0.061(7) 0 0.034(8)
0.050(8) 0 0 0.352(8) -0.013(10) 0 0 0 0 0 0 0 0 0 1.007983 0.960473 0.960473
0.960473 0.960473 0.960473 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(2) 4.0918 0 -0.022(7) 0.005(7) 0 -0.176(6) 0 0 -0.010(6) -0.014(7) 0 0.019(8)
-0.006(8) 0 0 0.240(8) -0.010(9) 0 0 0 0 0 0 0 0 0 1.009642 0.986859 0.986859
0.986859 0.986859 0.986859 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(3) 4.0812 0 -0.007(7) -0.009(7) 0 -0.190(6) 0 0 0.004(6) -0.011(7) 0 0.007(8)
0.018(8) 0 0 0.222(8) -0.025(9) 0 0 0 0 0 0 0 0 0 1.009642 0.986859 0.986859
0.986859 0.986859 0.986859 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(4) 4.0981 0 0.040(7) 0.068(7) 0 -0.161(6) 0 0 0.048(7) -0.048(7) 0 0.024(8)
0.028(8) 0 0 0.303(8) -0.017(10) 0 0 0 0 0 0 0 0 0 1.008945 0.967246 0.967246
0.967246 0.967246 0.967246 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(5) 4.0699 0 -0.006(7) 0.016(7) 0 -0.188(7) 0 0 -0.006(6) -0.014(7) 0
-0.004(8) 0.003(8) 0 0 0.255(8) -0.011(9) 0 0 0 0 0 0 0 0 0 1.009642 0.986859
0.986859 0.986859 0.986859 0.986859 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4
3.1762
C(6) 4.065 0 -0.006(7) 0.011(7) 0 -0.177(7) 0 0 -0.004(7) -0.021(7) 0 -0.014(8)
-0.005(8) 0 0 0.222(8) 0.015(9) 0 0 0 0 0 0 0 0 0 1.009642 0.986859 0.986859
0.986859 0.986859 0.986859 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(7) 4.1209 0 0.024(6) -0.023(7) 0.073(7) 0.222(7) -0.009(6) 0.021(7) -0.199(6)
-0.004(6) 0.335(9) -0.018(9) 0.016(10) 0.246(9) -0.018(9) -0.001(8) 0.014(8) 0
0 0 0 0 0 0 0 0 1.008945 0.967246 0.967246 0.967246 0.967246 0.967246 2 3.1762
2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(8) 4.0909 0 -0.023(9) -0.021(8) 0.047(8) 0.020(8) -0.028(7) 0.020(7)
-0.021(8) -0.033(8) 0.116(10) 0.046(10) 0.034(9) -0.075(10) -0.152(10) 0.060(9)
-0.122(9) 0 0 0 0 0 0 0 0 0 1.008142 0.888543 0.888543 0.888543 0.888543
0.888543 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
H(1O) 0.8734 0 0 0 0.257(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(1N) 0.8132 0 0 0 0.157(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(2) 0.8894 0 0 0 0.119(7) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3) 0.8572 0 0 0 0.149(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(5) 0.8699 0 0 0 0.130(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(6) 0.8776 0 0 0 0.148(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(8B) 0.8553 0 0 0 0.156(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(8C) 0.9149 0 0 0 0.159(10) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(8A) 0.9073 0 0 0 0.211(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) H(1O) Z O(1) C(1) Y
O(2) C(7) Z O(2) N(1) Y
N(1) H(1N) Z N(1) C(7) Y
C(1) C(6) X C(1) C(2) Y
C(2) C(1) X C(2) C(3) Y
C(3) C(4) X C(3) C(2) Y
C(4) C(3) X C(4) C(5) Y
C(5) C(4) X C(5) C(6) Y
C(6) C(1) X C(6) C(5) Y
C(7) O(2) Z C(7) N(1) Y
C(8) H(8B) Z C(8) H(8A) Y
H(1O) O(1) Z H(1O) C(1) Y
H(1N) N(1) Z H(1N) C(7) Y
H(2) C(2) Z H(2) C(1) Y
H(3) C(3) Z H(3) C(4) Y
H(5) C(5) Z H(5) C(4) Y
H(6) C(6) Z H(6) C(5) Y
H(8B) C(8) Z H(8B) H(8C) Y
H(8C) C(8) Z H(8C) H(8B) Y
H(8A) C(8) Z H(8A) H(8C) Y

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(1) 1.3653809082882 1_555 1_555 yes
O(1) H(1O) 0.9899976069716 1_555 1_555 yes
O(2) C(7) 1.2397381975772 1_555 1_555 yes
N(1) C(4) 1.4142583441474 1_555 1_555 yes
N(1) C(7) 1.3454938492372 1_555 1_555 yes
N(1) H(1N) 1.0150001683951 1_555 1_555 yes
C(1) C(2) 1.3951954095898 1_555 1_555 yes
C(1) C(6) 1.3964304362334 1_555 1_555 yes
C(2) C(3) 1.3945376775457 1_555 1_555 yes
C(2) H(2) 1.0799989180296 1_555 1_555 yes
C(3) C(4) 1.3970055908884 1_555 1_555 yes
C(3) H(3) 1.0799969843229 1_555 1_555 yes
C(4) C(5) 1.3977315547448 1_555 1_555 yes
C(5) C(6) 1.3908643111187 1_555 1_555 yes
C(5) H(5) 1.0799970599873 1_555 1_555 yes
C(6) H(6) 1.0800028150651 1_555 1_555 yes
C(7) C(8) 1.5086786652035 1_555 1_555 yes
C(8) H(8B) 1.0799994782116 1_555 1_555 yes
C(8) H(8C) 1.0799982214182 1_555 1_555 yes
C(8) H(8A) 1.0799980711171 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(1) O(1) H(1O) 111.08327034576 1_555 1_555 1_555 yes
C(4) N(1) C(7) 128.25324389162 1_555 1_555 1_555 yes
C(4) N(1) H(1N) 113.15389213699 1_555 1_555 1_555 yes
C(7) N(1) H(1N) 118.51012675951 1_555 1_555 1_555 yes
O(1) C(1) C(2) 118.38269501487 1_555 1_555 1_555 yes
O(1) C(1) C(6) 122.09787550247 1_555 1_555 1_555 yes
C(2) C(1) C(6) 119.51892040874 1_555 1_555 1_555 yes
C(1) C(2) C(3) 120.59774921864 1_555 1_555 1_555 yes
C(1) C(2) H(2) 119.45812799059 1_555 1_555 1_555 yes
C(3) C(2) H(2) 119.90827654345 1_555 1_555 1_555 yes
C(2) C(3) C(4) 119.88318610313 1_555 1_555 1_555 yes
C(2) C(3) H(3) 120.49510348101 1_555 1_555 1_555 yes
C(4) C(3) H(3) 119.57412265949 1_555 1_555 1_555 yes
N(1) C(4) C(3) 124.09797891734 1_555 1_555 1_555 yes
N(1) C(4) C(5) 116.5213433252 1_555 1_555 1_555 yes
C(3) C(4) C(5) 119.36294253995 1_555 1_555 1_555 yes
C(4) C(5) C(6) 120.70541011164 1_555 1_555 1_555 yes
C(4) C(5) H(5) 118.51935238402 1_555 1_555 1_555 yes
C(6) C(5) H(5) 120.77455039605 1_555 1_555 1_555 yes
C(1) C(6) C(5) 119.90339359783 1_555 1_555 1_555 yes
C(1) C(6) H(6) 121.34724588508 1_555 1_555 1_555 yes
C(5) C(6) H(6) 118.74823803555 1_555 1_555 1_555 yes
O(2) C(7) N(1) 123.3562828268 1_555 1_555 1_555 yes
O(2) C(7) C(8) 121.63156708401 1_555 1_555 1_555 yes
N(1) C(7) C(8) 115.01029777536 1_555 1_555 1_555 yes
C(7) C(8) H(8B) 110.09341048931 1_555 1_555 1_555 yes
C(7) C(8) H(8C) 111.02214793513 1_555 1_555 1_555 yes
C(7) C(8) H(8A) 112.95395624986 1_555 1_555 1_555 yes
H(8B) C(8) H(8C) 103.4276426239 1_555 1_555 1_555 yes
H(8B) C(8) H(8A) 113.71394765063 1_555 1_555 1_555 yes
H(8C) C(8) H(8A) 105.0984911709 1_555 1_555 1_555 yes

# Attachment '2_xd.cif'

#\#CIF_1.1

# Archive CIF produced by XD routine XDCIF
# Created on 30-Mar-03 at 14:26:56
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.3
# Request file : c:/xd2006/lib/xd/xdcif.dat
# CIF files read : geo lsm

data_A
_database_code_depnum_ccdc_archive 'CCDC 754967'
#TrackingRef '2_xd.cif'

_audit_creation_date             '30-Mar-03 T14:26:56-00:00'
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 -X,1/2+Y,1/2-Z
4 1/2+X,1/2-Y,-Z
5 -X,-Y,-Z
6 1/2+X,+Y,1/2-Z
7 +X,1/2-Y,1/2+Z
8 1/2-X,1/2+Y,+Z

_cell_length_a                   11.7652(2)
_cell_length_b                   7.1877(2)
_cell_length_c                   17.1679(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1451.80(5)

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_process_details   'APEX2 (Bruker, 2005)'

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(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  'Bruker SMART APEX2 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            200874
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0105
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         57.49
_reflns_number_total             10140
_reflns_number_gt                8034
_reflns_threshold_expression     I>2/s(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
?
;
_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w1 = [Fo*sqrt(w2) + sqrt(Fo^2^w2^2^ + sqrt(w2^2^))]^2^
where
calc w2 = q/[s^2^(Fo^2^) + (0.02 P)^2^ + 0.10 P + 0.00 + 0.00 sin(th)]
where P = (0.3333 Fo^2^ + 0.6667 Fc^2^)
q = 1.0
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6708
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.022
_refine_ls_R_factor_gt           0.018
_refine_ls_wR_factor_ref         0.021
_refine_ls_goodness_of_fit_ref   2.222
_refine_ls_shift/su_max          0.00001

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O(1) 0.738826 0.237239 0.630817 0.015 1 8
O(2) 0.60631 0.270128 1.002025 0.02 1 8
N(1) 0.48249 0.206363 0.903762 0.013 1 8
C(1) 0.678389 0.22342 0.698569 0.011 1 8
C(2) 0.724605 0.29518 0.767127 0.011 1 8
C(3) 0.663338 0.287764 0.836708 0.011 1 8
C(4) 0.55489 0.207988 0.837917 0.01 1 8
C(5) 0.510649 0.130697 0.769507 0.011 1 8
C(6) 0.571943 0.137739 0.700411 0.011 1 8
C(7) 0.508635 0.236588 0.979207 0.013 1 8
C(8) 0.408382 0.228393 1.033942 0.017 1 8
H(1O) 0.686781 0.229192 0.58563 0.033 1 8
H(1N) 0.399218 0.185639 0.890973 0.023 1 8
H(2) 0.807078 0.360981 0.765109 0.023 1 8
H(3) 0.698375 0.349909 0.888707 0.021 1 8
H(5) 0.428168 0.064784 0.77043 0.018 1 8
H(6) 0.538635 0.076342 0.647727 0.024 1 8
H(8C) 0.376489 0.367442 1.043464 0.04 1 8
H(8B) 0.431894 0.168396 1.089321 0.028 1 8
H(8A) 0.338349 0.148108 1.011046 0.034 1 8

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
O(1) 0.010724 0.025101 0.01011 0.000236 0.001351 -0.000805
O(2) 0.012315 0.038441 0.01039 -0.000384 -0.001297 -0.004701
N(1) 0.008701 0.019703 0.009334 0.000661 0.000229 -0.00113
C(1) 0.008836 0.013804 0.009518 0.000287 0.000296 -0.000053
C(2) 0.008357 0.014834 0.010468 0.000311 -0.000026 -0.001462
C(3) 0.008652 0.015373 0.00973 -0.000374 -0.000609 -0.001683
C(4) 0.008163 0.01342 0.00921 0.0006 -0.000259 -0.000824
C(5) 0.00912 0.013563 0.010523 -0.000079 -0.000506 -0.002111
C(6) 0.010151 0.013873 0.009949 -0.000923 -0.000537 -0.001262
C(7) 0.010401 0.019408 0.009448 0.000685 0.000233 -0.000735
C(8) 0.013914 0.025504 0.012242 0.000632 0.003181 -0.0005

#----------------------------------------------------------------------------#
# MULTIPOLE PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
O(1) 6.1333 0 0.017(4) -0.070(4) -0.050(4) -0.030(5) 0.015(4) 0.036(4) 0.083(4)
0.017(4) 0.087(6) 0.005(6) -0.007(5) 0.062(6) 0.000(5) -0.010(6) -0.013(6) 0 0
0 0 0 0 0 0 0 0.996807 0.92971 0.92971 0.92971 0.92971 0.92971 2 4.466 2 4.466
2 4.466 3 4.466 4 4.466
O(2) 6.1257 0 -0.017(5) -0.020(4) -0.066(4) -0.042(5) -0.014(5) 0.007(4)
-0.083(5) 0.021(4) -0.001(6) 0.010(6) 0.002(6) 0.050(6) -0.002(6) -0.014(6)
0.004(6) 0 0 0 0 0 0 0 0 0 0.996961 0.98395 0.98395 0.98395 0.98395 0.98395 2
4.466 2 4.466 2 4.466 3 4.466 4 4.466
N(1) 5.0923 0 0.018(5) 0.022(5) 0.017(5) -0.014(5) 0.001(5) -0.006(5) 0.015(5)
-0.005(5) 0.160(6) -0.004(6) 0.012(6) 0.104(6) -0.019(6) 0.003(6) 0.024(6) 0 0
0 0 0 0 0 0 0 1.001255 0.973398 0.973398 0.973398 0.973398 0.973398 2 3.83936 2
3.83936 2 3.83936 3 3.83936 4 3.83936
C(1) 4.0867 0 0.043(7) 0.085(7) 0 -0.161(6) 0 0 0.027(7) -0.069(6) 0 0.023(8)
0.040(8) 0 0 0.332(8) 0.019(9) 0 0 0 0 0 0 0 0 0 1.005588 0.966963 0.966963
0.966963 0.966963 0.966963 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(2) 4.0349 0 -0.006(7) -0.004(7) 0 -0.162(6) 0 0 0.017(6) -0.002(6) 0 0.008(8)
0.018(8) 0 0 0.224(8) 0.013(8) 0 0 0 0 0 0 0 0 0 1.007292 0.990711 0.990711
0.990711 0.990711 0.990711 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(3) 4.1091 0 -0.017(7) 0.027(7) 0 -0.160(6) 0 0 -0.013(6) 0.000(6) 0 0.015(7)
0.008(7) 0 0 0.238(7) -0.010(8) 0 0 0 0 0 0 0 0 0 1.007292 0.990711 0.990711
0.990711 0.990711 0.990711 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(4) 4.098 0 0.057(7) 0.074(7) 0 -0.142(6) 0 0 0.032(7) -0.067(7) 0 0.012(8)
0.046(8) 0 0 0.289(8) 0.003(9) 0 0 0 0 0 0 0 0 0 1.003108 0.959573 0.959573
0.959573 0.959573 0.959573 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(5) 4.1192 0 0.018(7) 0.009(7) 0 -0.144(6) 0 0 0.008(6) -0.024(6) 0 -0.013(8)
0.008(7) 0 0 0.227(7) 0.004(8) 0 0 0 0 0 0 0 0 0 1.007292 0.990711 0.990711
0.990711 0.990711 0.990711 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(6) 4.1253 0 -0.004(7) 0.014(7) 0 -0.157(6) 0 0 0.002(6) -0.017(6) 0 -0.014(8)
-0.004(8) 0 0 0.250(7) -0.006(8) 0 0 0 0 0 0 0 0 0 1.007292 0.990711 0.990711
0.990711 0.990711 0.990711 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(7) 4.0856 0 -0.001(7) -0.029(7) 0.054(7) 0.204(7) 0.010(6) -0.012(7)
-0.165(7) -0.003(6) 0.340(9) -0.009(9) -0.009(9) 0.235(9) -0.003(9) 0.006(8)
0.008(8) 0 0 0 0 0 0 0 0 0 1.003108 0.959573 0.959573 0.959573 0.959573
0.959573 2 3.1762 2 3.1762 2 3.1762 3 3.1762 4 3.1762
C(8) 4.0983 0 -0.057(7) 0.006(8) 0.014(8) 0.019(7) 0.033(6) -0.024(6) -0.009(6)
0.030(7) 0.147(9) -0.023(8) 0.019(8) -0.024(8) 0.081(8) -0.032(8) -0.139(8) 0 0
0 0 0 0 0 0 0 1.002264 0.982716 0.982716 0.982716 0.982716 0.982716 2 3.1762 2
3.1762 2 3.1762 3 3.1762 4 3.1762
H(1O) 0.8701 0 0 0 0.260(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(1N) 0.814 0 0 0 0.200(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(2) 0.8935 0 0 0 0.135(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(3) 0.8428 0 0 0 0.149(7) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(5) 0.8895 0 0 0 0.169(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(6) 0.9268 0 0 0 0.153(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(8C) 0.8956 0 0 0 0.162(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(8B) 0.8751 0 0 0 0.179(8) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2
H(8A) 0.8842 0 0 0 0.190(9) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.2 1.2
1.2 1.2 1.2 1.2 0 2 1 2 2 2 3 2 4 2

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) H(1O) Z O(1) C(1) Y
O(2) C(7) Z O(2) N(1) Y
N(1) H(1N) Z N(1) C(7) Y
C(1) C(6) X C(1) C(2) Y
C(2) C(3) X C(2) C(1) Y
C(3) C(4) X C(3) C(2) Y
C(4) C(5) X C(4) C(3) Y
C(5) C(4) X C(5) C(6) Y
C(6) C(1) X C(6) C(5) Y
C(7) O(2) Z C(7) N(1) Y
C(8) H(8A) Z C(8) H(8B) Y
H(1O) O(1) Z H(1O) C(1) Y
H(1N) N(1) Z H(1N) C(7) Y
H(2) C(2) Z H(2) C(1) Y
H(3) C(3) Z H(3) C(2) Y
H(5) C(5) Z H(5) C(6) Y
H(6) C(6) Z H(6) C(1) Y
H(8C) C(8) Z H(8C) H(8A) Y
H(8B) C(8) Z H(8B) H(8A) Y
H(8A) C(8) Z H(8A) H(8C) Y

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(1) 1.3668957741305 1_555 1_555 yes
O(1) H(1O) 0.98999645153089 1_555 1_555 yes
O(2) C(7) 1.2378031232062 1_555 1_555 yes
N(1) C(4) 1.41546881914 1_555 1_555 yes
N(1) C(7) 1.3488664772318 1_555 1_555 yes
N(1) H(1N) 1.0150023310292 1_555 1_555 yes
C(1) C(2) 1.3953537301168 1_555 1_555 yes
C(1) C(6) 1.3959481521396 1_555 1_555 yes
C(2) C(3) 1.3962072055806 1_555 1_555 yes
C(2) H(2) 1.0799967345862 1_555 1_555 yes
C(3) C(4) 1.3989913383475 1_555 1_555 yes
C(3) H(3) 1.07999174501 1_555 1_555 yes
C(4) C(5) 1.3996068351955 1_555 1_555 yes
C(5) C(6) 1.3891543245175 1_555 1_555 yes
C(5) H(5) 1.0799946924826 1_555 1_555 yes
C(6) H(6) 1.0799935729091 1_555 1_555 yes
C(7) C(8) 1.5092021595754 1_555 1_555 yes
C(8) H(8C) 1.0800021746683 1_555 1_555 yes
C(8) H(8B) 1.0799990114916 1_555 1_555 yes
C(8) H(8A) 1.0800038526239 1_555 1_555 yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(1) O(1) H(1O) 109.92671938556 1_555 1_555 1_555 yes
C(4) N(1) C(7) 128.92502207149 1_555 1_555 1_555 yes
C(4) N(1) H(1N) 114.16178715023 1_555 1_555 1_555 yes
C(7) N(1) H(1N) 116.8377037901 1_555 1_555 1_555 yes
O(1) C(1) C(2) 119.22336365651 1_555 1_555 1_555 yes
O(1) C(1) C(6) 121.19974370517 1_555 1_555 1_555 yes
C(2) C(1) C(6) 119.57508925977 1_555 1_555 1_555 yes
C(1) C(2) C(3) 120.42403378831 1_555 1_555 1_555 yes
C(1) C(2) H(2) 119.00732913377 1_555 1_555 1_555 yes
C(3) C(2) H(2) 120.5308054436 1_555 1_555 1_555 yes
C(2) C(3) C(4) 119.94652091739 1_555 1_555 1_555 yes
C(2) C(3) H(3) 119.62818784633 1_555 1_555 1_555 yes
C(4) C(3) H(3) 120.35539520906 1_555 1_555 1_555 yes
N(1) C(4) C(3) 124.33762071904 1_555 1_555 1_555 yes
N(1) C(4) C(5) 116.30020946118 1_555 1_555 1_555 yes
C(3) C(4) C(5) 119.3020779447 1_555 1_555 1_555 yes
C(4) C(5) C(6) 120.59969919829 1_555 1_555 1_555 yes
C(4) C(5) H(5) 119.73339100505 1_555 1_555 1_555 yes
C(6) C(5) H(5) 119.66685089333 1_555 1_555 1_555 yes
C(1) C(6) C(5) 120.07552115065 1_555 1_555 1_555 yes
C(1) C(6) H(6) 119.13193368205 1_555 1_555 1_555 yes
C(5) C(6) H(6) 120.79012502755 1_555 1_555 1_555 yes
O(2) C(7) N(1) 123.15975448144 1_555 1_555 1_555 yes
O(2) C(7) C(8) 122.42008261148 1_555 1_555 1_555 yes
N(1) C(7) C(8) 114.41664041578 1_555 1_555 1_555 yes
C(7) C(8) H(8C) 109.24799499044 1_555 1_555 1_555 yes
C(7) C(8) H(8B) 111.31684002982 1_555 1_555 1_555 yes
C(7) C(8) H(8A) 112.9848082173 1_555 1_555 1_555 yes
H(8C) C(8) H(8B) 108.98098856905 1_555 1_555 1_555 yes
H(8C) C(8) H(8A) 106.52830396796 1_555 1_555 1_555 yes
H(8B) C(8) H(8A) 107.60509179531 1_555 1_555 1_555 yes