# 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_0404__100
_database_code_depnum_ccdc_archive 'CCDC 816885'
_audit_update_record             
;
2011-03-10 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
#TrackingRef '4588_web_deposit_cif_file_0_BorisA.Zakharov_1299780018.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Paracetamol pyridine solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H9 N O2), C5 H5 N'
_chemical_formula_sum            'C21 H23 N3 O4'
_chemical_formula_weight         381.42

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/C
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5127(13)
_cell_length_b                   8.2524(5)
_cell_length_c                   17.957(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 122.004(6)
_cell_angle_gamma                90.00
_cell_volume                     1949.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10933
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      29.63

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18297
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         29.18
_reflns_number_total             5247
_reflns_number_gt                3690
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0489P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0120(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5247
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0863
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
O1A O 0.43909(7) 0.36648(12) 0.21443(6) 0.0208(2) Uani 1 1 d . . .
H11A H 0.4704 0.3609 0.2695 0.062(7) Uiso 1 1 calc R . .
C4B C 0.16998(9) 0.04506(15) 0.25128(8) 0.0166(2) Uani 1 1 d . . .
C1B C 0.37610(9) -0.03802(15) 0.33829(8) 0.0176(2) Uani 1 1 d . . .
O1B O 0.47749(7) -0.07556(12) 0.38436(6) 0.0221(2) Uani 1 1 d . . .
H11B H 0.4964 -0.0941 0.3491 0.046(5) Uiso 1 1 calc R . .
N1B N 0.06645(8) 0.09442(14) 0.20260(6) 0.0189(2) Uani 1 1 d . . .
H1B H 0.0408 0.1193 0.1471 0.036(5) Uiso 1 1 calc R . .
N1A N 0.05531(8) 0.63800(13) 0.08816(6) 0.0180(2) Uani 1 1 d . . .
H1A H 0.0281 0.6073 0.1182 0.033(4) Uiso 1 1 calc R . .
C3B C 0.21024(9) -0.02581(16) 0.20558(8) 0.0185(2) Uani 1 1 d . . .
H3B H 0.1672 -0.0455 0.1444 0.025(4) Uiso 1 1 calc R . .
C1A C 0.34435(9) 0.43295(15) 0.18268(8) 0.0179(2) Uani 1 1 d . . .
O2B O 0.02931(7) 0.06827(13) 0.30856(6) 0.0254(2) Uani 1 1 d . . .
C4A C 0.15162(9) 0.57083(15) 0.11561(8) 0.0171(2) Uani 1 1 d . . .
C3A C 0.19261(10) 0.46342(16) 0.18665(8) 0.0188(2) Uani 1 1 d . . .
H3A H 0.1546 0.4373 0.2126 0.022(4) Uiso 1 1 calc R . .
C2B C 0.31235(9) -0.06799(16) 0.24838(8) 0.0189(3) Uani 1 1 d . . .
H2B H 0.3387 -0.1170 0.2167 0.022(4) Uiso 1 1 calc R . .
C5B C 0.23379(9) 0.07092(16) 0.34158(8) 0.0183(2) Uani 1 1 d . . .
H5B H 0.2071 0.1167 0.3738 0.024(4) Uiso 1 1 calc R . .
C6B C 0.33610(9) 0.03009(16) 0.38453(8) 0.0187(3) Uani 1 1 d . . .
H6B H 0.3790 0.0488 0.4458 0.025(4) Uiso 1 1 calc R . .
O2A O 0.02676(7) 0.79548(12) -0.02700(6) 0.0244(2) Uani 1 1 d . . .
C6A C 0.30342(10) 0.53666(16) 0.11092(8) 0.0209(3) Uani 1 1 d . . .
H6A H 0.3413 0.5611 0.0847 0.022(4) Uiso 1 1 calc R . .
C7A C -0.00041(9) 0.74300(16) 0.02196(7) 0.0183(2) Uani 1 1 d . . .
N1S N 0.54714(8) 0.39656(14) 0.38776(7) 0.0225(2) Uani 1 1 d . . .
C2A C 0.28761(9) 0.39453(16) 0.21979(8) 0.0190(3) Uani 1 1 d . . .
H2A H 0.3140 0.3212 0.2678 0.022(4) Uiso 1 1 calc R . .
C7B C 0.00360(9) 0.10701(16) 0.23292(8) 0.0189(3) Uani 1 1 d . . .
C5A C 0.20756(9) 0.60546(16) 0.07679(8) 0.0202(3) Uani 1 1 d . . .
H5A H 0.1803 0.6755 0.0274 0.025(4) Uiso 1 1 calc R . .
C8A C -0.09933(10) 0.79586(17) 0.01141(8) 0.0219(3) Uani 1 1 d . . .
H8A1 H -0.0992 0.9138 0.0177 0.038(5) Uiso 1 1 calc R . .
H8A2 H -0.1072 0.7438 0.0565 0.038(5) Uiso 1 1 calc R . .
H8A3 H -0.1559 0.7643 -0.0469 0.037(5) Uiso 1 1 calc R . .
C8B C -0.10083(10) 0.17183(18) 0.16800(9) 0.0242(3) Uani 1 1 d . . .
H8B1 H -0.0953 0.2838 0.1528 0.054(6) Uiso 1 1 calc R . .
H8B3 H -0.1425 0.1691 0.1941 0.052(6) Uiso 1 1 calc R . .
H8B2 H -0.1326 0.1048 0.1149 0.061(6) Uiso 1 1 calc R . .
C1S C 0.59158(11) 0.54065(16) 0.39807(8) 0.0239(3) Uani 1 1 d . . .
H1S H 0.5828 0.5936 0.3475 0.035(5) Uiso 1 1 calc R . .
C2S C 0.64967(10) 0.61665(17) 0.47867(9) 0.0237(3) Uani 1 1 d . . .
H2S H 0.6800 0.7191 0.4833 0.030(4) Uiso 1 1 calc R . .
C3S C 0.66246(10) 0.53961(17) 0.55237(8) 0.0240(3) Uani 1 1 d . . .
H3S H 0.7019 0.5884 0.6087 0.029(4) Uiso 1 1 calc R . .
C5S C 0.56020(10) 0.32315(17) 0.45969(9) 0.0240(3) Uani 1 1 d . . .
H5S H 0.5292 0.2206 0.4534 0.028(4) Uiso 1 1 calc R . .
C4S C 0.61687(11) 0.39037(17) 0.54271(9) 0.0251(3) Uani 1 1 d . . .
H4S H 0.6244 0.3351 0.5922 0.034(4) Uiso 1 1 calc R . .


_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
O1A C1A 1.3775(15) . ?
O1A H11A 0.8400 . ?
C4B C3B 1.3960(17) . ?
C4B C5B 1.3975(16) . ?
C4B N1B 1.4218(15) . ?
C1B O1B 1.3693(15) . ?
C1B C6B 1.3915(18) . ?
C1B C2B 1.3976(17) . ?
O1B H11B 0.8400 . ?
N1B C7B 1.3492(16) . ?
N1B H1B 0.8800 . ?
N1A C7A 1.3498(16) . ?
N1A C4A 1.4147(16) . ?
N1A H1A 0.8800 . ?
C3B C2B 1.3894(17) . ?
C3B H3B 0.9500 . ?
C1A C6A 1.3889(18) . ?
C1A C2A 1.3931(17) . ?
O2B C7B 1.2377(15) . ?
C4A C3A 1.3990(17) . ?
C4A C5A 1.4007(17) . ?
C3A C2A 1.3855(18) . ?
C3A H3A 0.9500 . ?
C2B H2B 0.9500 . ?
C5B C6B 1.3892(17) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
O2A C7A 1.2372(15) . ?
C6A C5A 1.3940(18) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.5075(17) . ?
N1S C1S 1.3372(18) . ?
N1S C5S 1.3413(17) . ?
C2A H2A 0.9500 . ?
C7B C8B 1.5059(18) . ?
C5A H5A 0.9500 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C8B H8B1 0.9800 . ?
C8B H8B3 0.9800 . ?
C8B H8B2 0.9800 . ?
C1S C2S 1.3847(18) . ?
C1S H1S 0.9500 . ?
C2S C3S 1.3846(19) . ?
C2S H2S 0.9500 . ?
C3S C4S 1.385(2) . ?
C3S H3S 0.9500 . ?
C5S C4S 1.3834(19) . ?
C5S H5S 0.9500 . ?
C4S H4S 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
C1A O1A H11A 109.5 . . ?
C3B C4B C5B 118.92(11) . . ?
C3B C4B N1B 118.04(10) . . ?
C5B C4B N1B 122.98(11) . . ?
O1B C1B C6B 117.61(11) . . ?
O1B C1B C2B 122.74(11) . . ?
C6B C1B C2B 119.63(11) . . ?
C1B O1B H11B 109.5 . . ?
C7B N1B C4B 126.61(10) . . ?
C7B N1B H1B 116.7 . . ?
C4B N1B H1B 116.7 . . ?
C7A N1A C4A 128.58(11) . . ?
C7A N1A H1A 115.7 . . ?
C4A N1A H1A 115.7 . . ?
C2B C3B C4B 120.92(11) . . ?
C2B C3B H3B 119.5 . . ?
C4B C3B H3B 119.5 . . ?
O1A C1A C6A 119.48(11) . . ?
O1A C1A C2A 121.15(11) . . ?
C6A C1A C2A 119.34(12) . . ?
C3A C4A C5A 118.74(11) . . ?
C3A C4A N1A 116.85(11) . . ?
C5A C4A N1A 124.40(11) . . ?
C2A C3A C4A 121.17(11) . . ?
C2A C3A H3A 119.4 . . ?
C4A C3A H3A 119.4 . . ?
C3B C2B C1B 119.73(11) . . ?
C3B C2B H2B 120.1 . . ?
C1B C2B H2B 120.1 . . ?
C6B C5B C4B 120.36(11) . . ?
C6B C5B H5B 119.8 . . ?
C4B C5B H5B 119.8 . . ?
C5B C6B C1B 120.41(11) . . ?
C5B C6B H6B 119.8 . . ?
C1B C6B H6B 119.8 . . ?
C1A C6A C5A 121.03(12) . . ?
C1A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
O2A C7A N1A 123.37(12) . . ?
O2A C7A C8A 121.12(11) . . ?
N1A C7A C8A 115.51(11) . . ?
C1S N1S C5S 117.69(11) . . ?
C3A C2A C1A 119.94(11) . . ?
C3A C2A H2A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
O2B C7B N1B 122.79(11) . . ?
O2B C7B C8B 122.00(11) . . ?
N1B C7B C8B 115.21(10) . . ?
C6A C5A C4A 119.74(11) . . ?
C6A C5A H5A 120.1 . . ?
C4A C5A H5A 120.1 . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
H8B3 C8B H8B2 109.5 . . ?
N1S C1S C2S 123.35(12) . . ?
N1S C1S H1S 118.3 . . ?
C2S C1S H1S 118.3 . . ?
C3S C2S C1S 118.37(13) . . ?
C3S C2S H2S 120.8 . . ?
C1S C2S H2S 120.8 . . ?
C2S C3S C4S 118.94(12) . . ?
C2S C3S H3S 120.5 . . ?
C4S C3S H3S 120.5 . . ?
N1S C5S C4S 122.82(13) . . ?
N1S C5S H5S 118.6 . . ?
C4S C5S H5S 118.6 . . ?
C5S C4S C3S 118.84(12) . . ?
C5S C4S H4S 120.6 . . ?
C3S C4S H4S 120.6 . . ?

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
C3B C4B N1B C7B 153.35(13) . . . . ?
C5B C4B N1B C7B -29.6(2) . . . . ?
C5B C4B C3B C2B -1.00(19) . . . . ?
N1B C4B C3B C2B 176.18(12) . . . . ?
C7A N1A C4A C3A -179.77(12) . . . . ?
C7A N1A C4A C5A 0.5(2) . . . . ?
C5A C4A C3A C2A 1.38(18) . . . . ?
N1A C4A C3A C2A -178.35(11) . . . . ?
C4B C3B C2B C1B -0.55(19) . . . . ?
O1B C1B C2B C3B -179.57(12) . . . . ?
C6B C1B C2B C3B 1.61(19) . . . . ?
C3B C4B C5B C6B 1.49(19) . . . . ?
N1B C4B C5B C6B -175.54(12) . . . . ?
C4B C5B C6B C1B -0.43(19) . . . . ?
O1B C1B C6B C5B 179.99(12) . . . . ?
C2B C1B C6B C5B -1.13(19) . . . . ?
O1A C1A C6A C5A 179.67(11) . . . . ?
C2A C1A C6A C5A 1.41(19) . . . . ?
C4A N1A C7A O2A 1.1(2) . . . . ?
C4A N1A C7A C8A -178.12(11) . . . . ?
C4A C3A C2A C1A 0.50(19) . . . . ?
O1A C1A C2A C3A 179.87(11) . . . . ?
C6A C1A C2A C3A -1.89(18) . . . . ?
C4B N1B C7B O2B -3.5(2) . . . . ?
C4B N1B C7B C8B 176.55(12) . . . . ?
C1A C6A C5A C4A 0.5(2) . . . . ?
C3A C4A C5A C6A -1.86(18) . . . . ?
N1A C4A C5A C6A 177.85(12) . . . . ?
C5S N1S C1S C2S -0.1(2) . . . . ?
N1S C1S C2S C3S 0.0(2) . . . . ?
C1S C2S C3S C4S 0.0(2) . . . . ?
C1S N1S C5S C4S 0.2(2) . . . . ?
N1S C5S C4S C3S -0.2(2) . . . . ?
C2S C3S C4S C5S 0.1(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
N1A H1A O2B 0.88 1.97 2.8415(14) 172.4 2
N1B H1B O2A 0.88 1.96 2.8331(13) 170.7 3_565
O1B H11B O1A 0.84 1.90 2.7357(13) 170.7 2_645
O1A H11A N1S 0.84 1.83 2.6512(14) 166.7 .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        29.18
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_0304__125
_database_code_depnum_ccdc_archive 'CCDC 816886'
_audit_update_record             
;
2011-03-10 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
#TrackingRef '4589_web_deposit_cif_file_1_BorisA.Zakharov_1299780018.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Paracetamol pyridine solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H9 N O2), C5 H5 N'
_chemical_formula_sum            'C21 H23 N3 O4'
_chemical_formula_weight         381.42

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/C
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5180(14)
_cell_length_b                   8.2664(5)
_cell_length_c                   17.978(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.982(7)
_cell_angle_gamma                90.00
_cell_volume                     1956.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    10046
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      29.63

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18352
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0474
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         29.18
_reflns_number_total             5267
_reflns_number_gt                3547
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0459P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0105(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5267
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0927
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_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
O1A O 0.43893(7) 0.36746(12) 0.21412(6) 0.0243(2) Uani 1 1 d . . .
H11A H 0.4702 0.3617 0.2691 0.069(7) Uiso 1 1 calc R . .
C4B C 0.17021(9) 0.04586(15) 0.25145(8) 0.0191(2) Uani 1 1 d . . .
C1B C 0.37591(9) -0.03771(16) 0.33826(8) 0.0203(3) Uani 1 1 d . . .
O1B O 0.47722(7) -0.07550(13) 0.38433(6) 0.0262(2) Uani 1 1 d . . .
H11B H 0.4962 -0.0938 0.3492 0.061(6) Uiso 1 1 calc R . .
N1B N 0.06660(8) 0.09515(14) 0.20285(7) 0.0217(2) Uani 1 1 d . . .
H1B H 0.0410 0.1200 0.1474 0.039(5) Uiso 1 1 calc R . .
N1A N 0.05539(8) 0.63835(13) 0.08818(6) 0.0206(2) Uani 1 1 d . . .
H1A H 0.0283 0.6076 0.1182 0.027(4) Uiso 1 1 calc R . .
C3B C 0.21018(10) -0.02496(16) 0.20577(8) 0.0212(3) Uani 1 1 d . . .
H3B H 0.1672 -0.0446 0.1446 0.027(4) Uiso 1 1 calc R . .
C1A C 0.34416(9) 0.43369(16) 0.18251(8) 0.0206(3) Uani 1 1 d . . .
O2B O 0.02936(7) 0.06924(13) 0.30841(6) 0.0299(2) Uani 1 1 d . . .
C4A C 0.15174(9) 0.57152(15) 0.11562(8) 0.0196(2) Uani 1 1 d . . .
C3A C 0.19283(10) 0.46470(16) 0.18667(8) 0.0219(3) Uani 1 1 d . . .
H3A H 0.1550 0.4391 0.2128 0.027(4) Uiso 1 1 calc R . .
C2B C 0.31231(9) -0.06714(16) 0.24864(8) 0.0212(3) Uani 1 1 d . . .
H2B H 0.3387 -0.1159 0.2169 0.024(4) Uiso 1 1 calc R . .
C5B C 0.23377(9) 0.07149(16) 0.34153(8) 0.0208(3) Uani 1 1 d . . .
H5B H 0.2070 0.1172 0.3737 0.023(4) Uiso 1 1 calc R . .
C6B C 0.33596(10) 0.03034(16) 0.38436(8) 0.0213(3) Uani 1 1 d . . .
H6B H 0.3789 0.0489 0.4456 0.031(4) Uiso 1 1 calc R . .
O2A O 0.02661(7) 0.79510(13) -0.02695(6) 0.0288(2) Uani 1 1 d . . .
C6A C 0.30325(10) 0.53726(17) 0.11083(9) 0.0241(3) Uani 1 1 d . . .
H6A H 0.3411 0.5618 0.0846 0.032(4) Uiso 1 1 calc R . .
C7A C -0.00040(9) 0.74296(16) 0.02202(8) 0.0210(3) Uani 1 1 d . . .
N1S N 0.54708(9) 0.39732(14) 0.38734(7) 0.0262(2) Uani 1 1 d . . .
C2A C 0.28738(10) 0.39560(16) 0.21955(8) 0.0221(3) Uani 1 1 d . . .
H2A H 0.3136 0.3222 0.2674 0.031(4) Uiso 1 1 calc R . .
C7B C 0.00369(10) 0.10772(16) 0.23289(8) 0.0216(3) Uani 1 1 d . . .
C5A C 0.20748(10) 0.60567(17) 0.07690(8) 0.0238(3) Uani 1 1 d . . .
H5A H 0.1801 0.6754 0.0275 0.033(4) Uiso 1 1 calc R . .
C8A C -0.09922(10) 0.79578(18) 0.01151(8) 0.0254(3) Uani 1 1 d . . .
H8A1 H -0.0994 0.9137 0.0171 0.045(5) Uiso 1 1 calc R . .
H8A2 H -0.1067 0.7449 0.0570 0.041(5) Uiso 1 1 calc R . .
H8A3 H -0.1558 0.7631 -0.0464 0.042(5) Uiso 1 1 calc R . .
C8B C -0.10064(10) 0.17229(19) 0.16819(9) 0.0281(3) Uani 1 1 d . . .
H8B1 H -0.0951 0.2836 0.1524 0.071(7) Uiso 1 1 calc R . .
H8B3 H -0.1420 0.1708 0.1946 0.059(6) Uiso 1 1 calc R . .
H8B2 H -0.1328 0.1046 0.1154 0.065(6) Uiso 1 1 calc R . .
C1S C 0.59170(11) 0.54135(17) 0.39814(9) 0.0278(3) Uani 1 1 d . . .
H1S H 0.5832 0.5948 0.3479 0.039(5) Uiso 1 1 calc R . .
C2S C 0.64952(11) 0.61607(17) 0.47882(9) 0.0281(3) Uani 1 1 d . . .
H2S H 0.6800 0.7184 0.4838 0.041(5) Uiso 1 1 calc R . .
C3S C 0.66200(11) 0.53907(18) 0.55186(9) 0.0282(3) Uani 1 1 d . . .
H3S H 0.7011 0.5876 0.6081 0.035(4) Uiso 1 1 calc R . .
C5S C 0.56011(11) 0.32358(17) 0.45902(9) 0.0279(3) Uani 1 1 d . . .
H5S H 0.5291 0.2211 0.4525 0.040(5) Uiso 1 1 calc R . .
C4S C 0.61668(11) 0.39000(18) 0.54200(9) 0.0299(3) Uani 1 1 d . . .
H4S H 0.6243 0.3343 0.5914 0.041(5) Uiso 1 1 calc R . .


_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
O1A C1A 1.3785(15) . ?
O1A H11A 0.8400 . ?
C4B C3B 1.3935(17) . ?
C4B C5B 1.3959(17) . ?
C4B N1B 1.4235(16) . ?
C1B O1B 1.3697(15) . ?
C1B C6B 1.3899(18) . ?
C1B C2B 1.3946(17) . ?
O1B H11B 0.8400 . ?
N1B C7B 1.3467(16) . ?
N1B H1B 0.8800 . ?
N1A C7A 1.3496(16) . ?
N1A C4A 1.4151(16) . ?
N1A H1A 0.8800 . ?
C3B C2B 1.3904(18) . ?
C3B H3B 0.9500 . ?
C1A C6A 1.3892(18) . ?
C1A C2A 1.3930(18) . ?
O2B C7B 1.2372(15) . ?
C4A C5A 1.3964(17) . ?
C4A C3A 1.3982(17) . ?
C3A C2A 1.3819(18) . ?
C3A H3A 0.9500 . ?
C2B H2B 0.9500 . ?
C5B C6B 1.3892(18) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
O2A C7A 1.2358(15) . ?
C6A C5A 1.3929(18) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.5069(18) . ?
N1S C1S 1.3387(18) . ?
N1S C5S 1.3405(18) . ?
C2A H2A 0.9500 . ?
C7B C8B 1.5048(18) . ?
C5A H5A 0.9500 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C8B H8B1 0.9800 . ?
C8B H8B3 0.9800 . ?
C8B H8B2 0.9800 . ?
C1S C2S 1.3826(19) . ?
C1S H1S 0.9500 . ?
C2S C3S 1.378(2) . ?
C2S H2S 0.9500 . ?
C3S C4S 1.383(2) . ?
C3S H3S 0.9500 . ?
C5S C4S 1.382(2) . ?
C5S H5S 0.9500 . ?
C4S H4S 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
C1A O1A H11A 109.5 . . ?
C3B C4B C5B 119.08(12) . . ?
C3B C4B N1B 117.99(11) . . ?
C5B C4B N1B 122.88(11) . . ?
O1B C1B C6B 117.61(11) . . ?
O1B C1B C2B 122.83(11) . . ?
C6B C1B C2B 119.56(12) . . ?
C1B O1B H11B 109.5 . . ?
C7B N1B C4B 126.80(10) . . ?
C7B N1B H1B 116.6 . . ?
C4B N1B H1B 116.6 . . ?
C7A N1A C4A 128.57(11) . . ?
C7A N1A H1A 115.7 . . ?
C4A N1A H1A 115.7 . . ?
C2B C3B C4B 120.74(11) . . ?
C2B C3B H3B 119.6 . . ?
C4B C3B H3B 119.6 . . ?
O1A C1A C6A 119.40(11) . . ?
O1A C1A C2A 121.33(12) . . ?
C6A C1A C2A 119.25(12) . . ?
C5A C4A C3A 118.67(12) . . ?
C5A C4A N1A 124.49(11) . . ?
C3A C4A N1A 116.84(11) . . ?
C2A C3A C4A 121.26(12) . . ?
C2A C3A H3A 119.4 . . ?
C4A C3A H3A 119.4 . . ?
C3B C2B C1B 119.87(11) . . ?
C3B C2B H2B 120.1 . . ?
C1B C2B H2B 120.1 . . ?
C6B C5B C4B 120.24(12) . . ?
C6B C5B H5B 119.9 . . ?
C4B C5B H5B 119.9 . . ?
C5B C6B C1B 120.49(11) . . ?
C5B C6B H6B 119.8 . . ?
C1B C6B H6B 119.8 . . ?
C1A C6A C5A 120.92(12) . . ?
C1A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
O2A C7A N1A 123.37(12) . . ?
O2A C7A C8A 121.07(12) . . ?
N1A C7A C8A 115.55(11) . . ?
C1S N1S C5S 117.51(12) . . ?
C3A C2A C1A 119.95(12) . . ?
C3A C2A H2A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
O2B C7B N1B 122.67(12) . . ?
O2B C7B C8B 121.92(12) . . ?
N1B C7B C8B 115.41(11) . . ?
C6A C5A C4A 119.90(12) . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
H8B3 C8B H8B2 109.5 . . ?
N1S C1S C2S 123.23(13) . . ?
N1S C1S H1S 118.4 . . ?
C2S C1S H1S 118.4 . . ?
C3S C2S C1S 118.62(13) . . ?
C3S C2S H2S 120.7 . . ?
C1S C2S H2S 120.7 . . ?
C2S C3S C4S 118.97(13) . . ?
C2S C3S H3S 120.5 . . ?
C4S C3S H3S 120.5 . . ?
N1S C5S C4S 122.90(13) . . ?
N1S C5S H5S 118.6 . . ?
C4S C5S H5S 118.6 . . ?
C5S C4S C3S 118.78(13) . . ?
C5S C4S H4S 120.6 . . ?
C3S C4S H4S 120.6 . . ?

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
C3B C4B N1B C7B 153.20(13) . . . . ?
C5B C4B N1B C7B -29.5(2) . . . . ?
C5B C4B C3B C2B -1.14(19) . . . . ?
N1B C4B C3B C2B 176.27(12) . . . . ?
C7A N1A C4A C5A 0.4(2) . . . . ?
C7A N1A C4A C3A -179.85(12) . . . . ?
C5A C4A C3A C2A 1.11(19) . . . . ?
N1A C4A C3A C2A -178.67(12) . . . . ?
C4B C3B C2B C1B -0.4(2) . . . . ?
O1B C1B C2B C3B -179.65(12) . . . . ?
C6B C1B C2B C3B 1.45(19) . . . . ?
C3B C4B C5B C6B 1.54(19) . . . . ?
N1B C4B C5B C6B -175.73(12) . . . . ?
C4B C5B C6B C1B -0.5(2) . . . . ?
O1B C1B C6B C5B 179.99(12) . . . . ?
C2B C1B C6B C5B -1.05(19) . . . . ?
O1A C1A C6A C5A 179.66(12) . . . . ?
C2A C1A C6A C5A 1.3(2) . . . . ?
C4A N1A C7A O2A 1.2(2) . . . . ?
C4A N1A C7A C8A -178.02(12) . . . . ?
C4A C3A C2A C1A 0.84(19) . . . . ?
O1A C1A C2A C3A 179.65(11) . . . . ?
C6A C1A C2A C3A -2.04(19) . . . . ?
C4B N1B C7B O2B -3.4(2) . . . . ?
C4B N1B C7B C8B 176.57(12) . . . . ?
C1A C6A C5A C4A 0.6(2) . . . . ?
C3A C4A C5A C6A -1.83(19) . . . . ?
N1A C4A C5A C6A 177.93(12) . . . . ?
C5S N1S C1S C2S -0.1(2) . . . . ?
N1S C1S C2S C3S 0.0(2) . . . . ?
C1S C2S C3S C4S 0.2(2) . . . . ?
C1S N1S C5S C4S 0.2(2) . . . . ?
N1S C5S C4S C3S 0.0(2) . . . . ?
C2S C3S C4S C5S -0.2(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
N1A H1A O2B 0.88 1.97 2.8464(14) 172.2 2
N1B H1B O2A 0.88 1.97 2.8408(14) 170.8 3_565
O1B H11B O1A 0.84 1.90 2.7362(13) 170.6 2_645
O1A H11A N1S 0.84 1.83 2.6532(15) 166.7 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.18
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.045
####################################################################### 
# 
# 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_0304__150
_database_code_depnum_ccdc_archive 'CCDC 816887'
_audit_update_record             
;
2011-03-10 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
#TrackingRef '4590_web_deposit_cif_file_2_BorisA.Zakharov_1299780018.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Paracetamol pyridine solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H9 N O2), C5 H5 N'
_chemical_formula_sum            'C21 H23 N3 O4'
_chemical_formula_weight         381.42

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/C
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5225(14)
_cell_length_b                   8.2788(5)
_cell_length_c                   17.997(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.964(7)
_cell_angle_gamma                90.00
_cell_volume                     1962.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9208
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      29.62

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18407
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         29.17
_reflns_number_total             5289
_reflns_number_gt                3404
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0461P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0106(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5289
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_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
O1A O 0.43872(7) 0.36859(12) 0.21381(6) 0.0286(2) Uani 1 1 d . . .
H11A H 0.4703 0.3641 0.2687 0.066(6) Uiso 1 1 calc R . .
C4B C 0.17022(9) 0.04639(16) 0.25155(8) 0.0219(3) Uani 1 1 d . . .
C1B C 0.37570(9) -0.03730(16) 0.33826(8) 0.0232(3) Uani 1 1 d . . .
O1B O 0.47688(7) -0.07520(13) 0.38429(6) 0.0305(2) Uani 1 1 d . . .
H11B H 0.4958 -0.0944 0.3492 0.058(6) Uiso 1 1 calc R . .
N1B N 0.06679(8) 0.09589(14) 0.20304(7) 0.0251(2) Uani 1 1 d . . .
H1B H 0.0413 0.1207 0.1477 0.043(5) Uiso 1 1 calc R . .
N1A N 0.05538(8) 0.63882(14) 0.08806(7) 0.0239(2) Uani 1 1 d . . .
H1A H 0.0283 0.6081 0.1181 0.032(4) Uiso 1 1 calc R . .
C3B C 0.21033(10) -0.02422(16) 0.20608(8) 0.0240(3) Uani 1 1 d . . .
H3B H 0.1674 -0.0436 0.1450 0.026(4) Uiso 1 1 calc R . .
C1A C 0.34395(10) 0.43486(16) 0.18222(8) 0.0236(3) Uani 1 1 d . . .
O2B O 0.02932(7) 0.07031(14) 0.30831(6) 0.0353(3) Uani 1 1 d . . .
C4A C 0.15171(9) 0.57224(16) 0.11551(8) 0.0225(3) Uani 1 1 d . . .
C3A C 0.19284(10) 0.46565(17) 0.18645(8) 0.0252(3) Uani 1 1 d . . .
H3A H 0.1550 0.4400 0.2126 0.028(4) Uiso 1 1 calc R . .
C2B C 0.31217(10) -0.06667(16) 0.24880(8) 0.0249(3) Uani 1 1 d . . .
H2B H 0.3385 -0.1156 0.2171 0.030(4) Uiso 1 1 calc R . .
C5B C 0.23373(10) 0.07184(17) 0.34142(8) 0.0239(3) Uani 1 1 d . . .
H5B H 0.2070 0.1176 0.3735 0.025(4) Uiso 1 1 calc R . .
C6B C 0.33572(10) 0.03065(17) 0.38416(8) 0.0249(3) Uani 1 1 d . . .
H6B H 0.3785 0.0491 0.4453 0.032(4) Uiso 1 1 calc R . .
O2A O 0.02637(7) 0.79484(13) -0.02707(6) 0.0336(2) Uani 1 1 d . . .
C6A C 0.30317(10) 0.53783(18) 0.11084(9) 0.0277(3) Uani 1 1 d . . .
H6A H 0.3410 0.5622 0.0846 0.035(4) Uiso 1 1 calc R . .
C7A C -0.00050(10) 0.74301(17) 0.02199(8) 0.0247(3) Uani 1 1 d . . .
N1S N 0.54700(9) 0.39836(15) 0.38687(8) 0.0307(3) Uani 1 1 d . . .
C2A C 0.28748(10) 0.39684(17) 0.21939(8) 0.0255(3) Uani 1 1 d . . .
H2A H 0.3139 0.3238 0.2673 0.034(4) Uiso 1 1 calc R . .
C7B C 0.00383(10) 0.10875(17) 0.23295(8) 0.0250(3) Uani 1 1 d . . .
C5A C 0.20757(10) 0.60608(17) 0.07700(8) 0.0275(3) Uani 1 1 d . . .
H5A H 0.1803 0.6757 0.0276 0.037(4) Uiso 1 1 calc R . .
C8A C -0.09909(10) 0.79561(19) 0.01175(9) 0.0297(3) Uani 1 1 d . . .
H8A1 H -0.0988 0.9131 0.0183 0.053(5) Uiso 1 1 calc R . .
H8A2 H -0.1069 0.7433 0.0567 0.048(5) Uiso 1 1 calc R . .
H8A3 H -0.1557 0.7646 -0.0464 0.049(5) Uiso 1 1 calc R . .
C8B C -0.10045(10) 0.1729(2) 0.16822(9) 0.0333(3) Uani 1 1 d . . .
H8B1 H -0.0950 0.2842 0.1526 0.082(7) Uiso 1 1 calc R . .
H8B3 H -0.1420 0.1707 0.1944 0.068(6) Uiso 1 1 calc R . .
H8B2 H -0.1323 0.1055 0.1155 0.080(7) Uiso 1 1 calc R . .
C1S C 0.59158(11) 0.54159(18) 0.39810(9) 0.0323(3) Uani 1 1 d . . .
H1S H 0.5832 0.5955 0.3481 0.045(5) Uiso 1 1 calc R . .
C2S C 0.64939(11) 0.61577(18) 0.47880(9) 0.0331(3) Uani 1 1 d . . .
H2S H 0.6799 0.7180 0.4840 0.048(5) Uiso 1 1 calc R . .
C3S C 0.66178(11) 0.53817(19) 0.55139(9) 0.0331(3) Uani 1 1 d . . .
H3S H 0.7010 0.5860 0.6077 0.041(5) Uiso 1 1 calc R . .
C5S C 0.55983(11) 0.32416(18) 0.45831(10) 0.0329(3) Uani 1 1 d . . .
H5S H 0.5286 0.2220 0.4515 0.040(4) Uiso 1 1 calc R . .
C4S C 0.61633(12) 0.38964(19) 0.54112(10) 0.0356(3) Uani 1 1 d . . .
H4S H 0.6239 0.3335 0.5903 0.050(5) Uiso 1 1 calc R . .


_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
O1A C1A 1.3794(16) . ?
O1A H11A 0.8400 . ?
C4B C3B 1.3923(18) . ?
C4B C5B 1.3944(17) . ?
C4B N1B 1.4226(16) . ?
C1B O1B 1.3689(15) . ?
C1B C6B 1.3881(18) . ?
C1B C2B 1.3938(17) . ?
O1B H11B 0.8400 . ?
N1B C7B 1.3466(16) . ?
N1B H1B 0.8800 . ?
N1A C7A 1.3484(17) . ?
N1A C4A 1.4147(16) . ?
N1A H1A 0.8800 . ?
C3B C2B 1.3881(18) . ?
C3B H3B 0.9500 . ?
C1A C6A 1.3844(19) . ?
C1A C2A 1.3914(18) . ?
O2B C7B 1.2365(15) . ?
C4A C5A 1.3955(18) . ?
C4A C3A 1.3975(18) . ?
C3A C2A 1.3828(19) . ?
C3A H3A 0.9500 . ?
C2B H2B 0.9500 . ?
C5B C6B 1.3875(18) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
O2A C7A 1.2358(16) . ?
C6A C5A 1.3912(19) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.5057(18) . ?
N1S C1S 1.3333(19) . ?
N1S C5S 1.3413(19) . ?
C2A H2A 0.9500 . ?
C7B C8B 1.5042(19) . ?
C5A H5A 0.9500 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C8B H8B1 0.9800 . ?
C8B H8B3 0.9800 . ?
C8B H8B2 0.9800 . ?
C1S C2S 1.383(2) . ?
C1S H1S 0.9500 . ?
C2S C3S 1.375(2) . ?
C2S H2S 0.9500 . ?
C3S C4S 1.380(2) . ?
C3S H3S 0.9500 . ?
C5S C4S 1.378(2) . ?
C5S H5S 0.9500 . ?
C4S H4S 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
C1A O1A H11A 109.5 . . ?
C3B C4B C5B 118.93(12) . . ?
C3B C4B N1B 118.09(11) . . ?
C5B C4B N1B 122.92(11) . . ?
O1B C1B C6B 117.63(11) . . ?
O1B C1B C2B 122.86(12) . . ?
C6B C1B C2B 119.50(12) . . ?
C1B O1B H11B 109.5 . . ?
C7B N1B C4B 126.84(11) . . ?
C7B N1B H1B 116.6 . . ?
C4B N1B H1B 116.6 . . ?
C7A N1A C4A 128.66(11) . . ?
C7A N1A H1A 115.7 . . ?
C4A N1A H1A 115.7 . . ?
C2B C3B C4B 120.88(11) . . ?
C2B C3B H3B 119.6 . . ?
C4B C3B H3B 119.6 . . ?
O1A C1A C6A 119.43(12) . . ?
O1A C1A C2A 121.18(12) . . ?
C6A C1A C2A 119.37(12) . . ?
C5A C4A C3A 118.49(12) . . ?
C5A C4A N1A 124.62(12) . . ?
C3A C4A N1A 116.90(11) . . ?
C2A C3A C4A 121.31(12) . . ?
C2A C3A H3A 119.3 . . ?
C4A C3A H3A 119.3 . . ?
C3B C2B C1B 119.84(12) . . ?
C3B C2B H2B 120.1 . . ?
C1B C2B H2B 120.1 . . ?
C6B C5B C4B 120.30(12) . . ?
C6B C5B H5B 119.9 . . ?
C4B C5B H5B 119.9 . . ?
C5B C6B C1B 120.53(12) . . ?
C5B C6B H6B 119.7 . . ?
C1B C6B H6B 119.7 . . ?
C1A C6A C5A 120.95(12) . . ?
C1A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
O2A C7A N1A 123.32(12) . . ?
O2A C7A C8A 121.18(12) . . ?
N1A C7A C8A 115.50(11) . . ?
C1S N1S C5S 117.40(12) . . ?
C3A C2A C1A 119.83(12) . . ?
C3A C2A H2A 120.1 . . ?
C1A C2A H2A 120.1 . . ?
O2B C7B N1B 122.66(12) . . ?
O2B C7B C8B 121.91(12) . . ?
N1B C7B C8B 115.43(11) . . ?
C6A C5A C4A 120.02(12) . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
H8B3 C8B H8B2 109.5 . . ?
N1S C1S C2S 123.40(13) . . ?
N1S C1S H1S 118.3 . . ?
C2S C1S H1S 118.3 . . ?
C3S C2S C1S 118.49(14) . . ?
C3S C2S H2S 120.8 . . ?
C1S C2S H2S 120.8 . . ?
C2S C3S C4S 118.97(13) . . ?
C2S C3S H3S 120.5 . . ?
C4S C3S H3S 120.5 . . ?
N1S C5S C4S 122.88(14) . . ?
N1S C5S H5S 118.6 . . ?
C4S C5S H5S 118.6 . . ?
C5S C4S C3S 118.86(13) . . ?
C5S C4S H4S 120.6 . . ?
C3S C4S H4S 120.6 . . ?

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
C3B C4B N1B C7B 153.32(13) . . . . ?
C5B C4B N1B C7B -29.5(2) . . . . ?
C5B C4B C3B C2B -1.0(2) . . . . ?
N1B C4B C3B C2B 176.29(12) . . . . ?
C7A N1A C4A C5A 0.4(2) . . . . ?
C7A N1A C4A C3A -179.78(13) . . . . ?
C5A C4A C3A C2A 1.2(2) . . . . ?
N1A C4A C3A C2A -178.62(12) . . . . ?
C4B C3B C2B C1B -0.5(2) . . . . ?
O1B C1B C2B C3B -179.60(13) . . . . ?
C6B C1B C2B C3B 1.6(2) . . . . ?
C3B C4B C5B C6B 1.5(2) . . . . ?
N1B C4B C5B C6B -175.67(13) . . . . ?
C4B C5B C6B C1B -0.4(2) . . . . ?
O1B C1B C6B C5B -179.98(12) . . . . ?
C2B C1B C6B C5B -1.1(2) . . . . ?
O1A C1A C6A C5A 179.64(12) . . . . ?
C2A C1A C6A C5A 1.3(2) . . . . ?
C4A N1A C7A O2A 1.3(2) . . . . ?
C4A N1A C7A C8A -177.90(12) . . . . ?
C4A C3A C2A C1A 0.6(2) . . . . ?
O1A C1A C2A C3A 179.79(12) . . . . ?
C6A C1A C2A C3A -1.9(2) . . . . ?
C4B N1B C7B O2B -3.4(2) . . . . ?
C4B N1B C7B C8B 176.80(13) . . . . ?
C1A C6A C5A C4A 0.6(2) . . . . ?
C3A C4A C5A C6A -1.8(2) . . . . ?
N1A C4A C5A C6A 178.01(13) . . . . ?
C5S N1S C1S C2S -0.1(2) . . . . ?
N1S C1S C2S C3S 0.0(2) . . . . ?
C1S C2S C3S C4S 0.1(2) . . . . ?
C1S N1S C5S C4S 0.0(2) . . . . ?
N1S C5S C4S C3S 0.1(2) . . . . ?
C2S C3S C4S C5S -0.1(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
N1A H1A O2B 0.88 1.98 2.8504(14) 172.1 2
N1B H1B O2A 0.88 1.97 2.8444(14) 170.9 3_565
O1B H11B O1A 0.84 1.91 2.7384(14) 170.3 2_645
O1A H11A N1S 0.84 1.83 2.6540(15) 167.8 .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.17
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_0204__175
_database_code_depnum_ccdc_archive 'CCDC 816888'
_audit_update_record             
;
2011-03-10 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
#TrackingRef '4591_web_deposit_cif_file_3_BorisA.Zakharov_1299780018.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Paracetamol pyridine solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H9 N O2), C5 H5 N'
_chemical_formula_sum            'C21 H23 N3 O4'
_chemical_formula_weight         381.42

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/C
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5304(15)
_cell_length_b                   8.2953(6)
_cell_length_c                   18.026(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.942(8)
_cell_angle_gamma                90.00
_cell_volume                     1970.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    175(2)
_cell_measurement_reflns_used    8433
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      29.63

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      175(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18493
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.55
_diffrn_reflns_theta_max         29.20
_reflns_number_total             5314
_reflns_number_gt                3219
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0464P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0101(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5314
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0956
_refine_ls_wR_factor_gt          0.0820
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_restrained_S_all      0.921
_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
O1A O 0.43843(7) 0.36974(13) 0.21342(6) 0.0332(2) Uani 1 1 d . . .
H11A H 0.4700 0.3654 0.2682 0.077(7) Uiso 1 1 calc R . .
C4B C 0.17029(10) 0.04750(17) 0.25180(8) 0.0244(3) Uani 1 1 d . . .
C1B C 0.37542(10) -0.03702(17) 0.33818(9) 0.0265(3) Uani 1 1 d . . .
O1B O 0.47647(7) -0.07498(14) 0.38420(6) 0.0354(3) Uani 1 1 d . . .
H11B H 0.4952 -0.0956 0.3492 0.065(6) Uiso 1 1 calc R . .
N1B N 0.06701(8) 0.09697(15) 0.20327(7) 0.0285(3) Uani 1 1 d . . .
H1B H 0.0417 0.1218 0.1480 0.042(5) Uiso 1 1 calc R . .
N1A N 0.05543(8) 0.63946(15) 0.08798(7) 0.0274(3) Uani 1 1 d . . .
H1A H 0.0284 0.6091 0.1181 0.037(4) Uiso 1 1 calc R . .
C3B C 0.21051(10) -0.02339(18) 0.20645(9) 0.0276(3) Uani 1 1 d . . .
H3B H 0.1677 -0.0428 0.1455 0.035(4) Uiso 1 1 calc R . .
C1A C 0.34382(10) 0.43609(17) 0.18195(9) 0.0274(3) Uani 1 1 d . . .
O2B O 0.02930(8) 0.07176(15) 0.30813(6) 0.0406(3) Uani 1 1 d . . .
C4A C 0.15171(10) 0.57305(17) 0.11549(8) 0.0254(3) Uani 1 1 d . . .
C3A C 0.19269(11) 0.46681(18) 0.18625(9) 0.0288(3) Uani 1 1 d . . .
H3A H 0.1548 0.4411 0.2122 0.033(4) Uiso 1 1 calc R . .
C2B C 0.31199(10) -0.06586(18) 0.24903(9) 0.0283(3) Uani 1 1 d . . .
H2B H 0.3383 -0.1147 0.2174 0.031(4) Uiso 1 1 calc R . .
C5B C 0.23372(10) 0.07232(18) 0.34145(8) 0.0275(3) Uani 1 1 d . . .
H5B H 0.2071 0.1179 0.3736 0.030(4) Uiso 1 1 calc R . .
C6B C 0.33547(10) 0.03080(18) 0.38405(9) 0.0281(3) Uani 1 1 d . . .
H6B H 0.3782 0.0489 0.4451 0.033(4) Uiso 1 1 calc R . .
O2A O 0.02607(8) 0.79442(15) -0.02714(7) 0.0388(3) Uani 1 1 d . . .
C6A C 0.30305(11) 0.53862(19) 0.11076(9) 0.0324(3) Uani 1 1 d . . .
H6A H 0.3409 0.5632 0.0846 0.037(4) Uiso 1 1 calc R . .
C7A C -0.00061(10) 0.74306(18) 0.02187(8) 0.0282(3) Uani 1 1 d . . .
N1S N 0.54693(10) 0.39942(16) 0.38642(8) 0.0356(3) Uani 1 1 d . . .
C2A C 0.28738(11) 0.39832(18) 0.21921(9) 0.0295(3) Uani 1 1 d . . .
H2A H 0.3138 0.3257 0.2671 0.041(5) Uiso 1 1 calc R . .
C7B C 0.00376(11) 0.10982(18) 0.23289(9) 0.0285(3) Uani 1 1 d . . .
C5A C 0.20735(11) 0.60642(19) 0.07685(9) 0.0318(3) Uani 1 1 d . . .
H5A H 0.1799 0.6754 0.0274 0.042(5) Uiso 1 1 calc R . .
C8A C -0.09902(11) 0.7953(2) 0.01189(9) 0.0336(3) Uani 1 1 d . . .
H8A1 H -0.0988 0.9126 0.0185 0.066(6) Uiso 1 1 calc R . .
H8A2 H -0.1067 0.7430 0.0568 0.060(6) Uiso 1 1 calc R . .
H8A3 H -0.1557 0.7643 -0.0461 0.055(5) Uiso 1 1 calc R . .
C8B C -0.10026(11) 0.1733(2) 0.16840(10) 0.0387(4) Uani 1 1 d . . .
H8B1 H -0.0950 0.2847 0.1531 0.093(8) Uiso 1 1 calc R . .
H8B3 H -0.1419 0.1703 0.1944 0.073(6) Uiso 1 1 calc R . .
H8B2 H -0.1318 0.1064 0.1156 0.093(8) Uiso 1 1 calc R . .
C1S C 0.59174(12) 0.5422(2) 0.39829(10) 0.0379(4) Uani 1 1 d . . .
H1S H 0.5835 0.5967 0.3486 0.052(5) Uiso 1 1 calc R . .
C2S C 0.64943(12) 0.6150(2) 0.47883(10) 0.0386(4) Uani 1 1 d . . .
H2S H 0.6803 0.7168 0.4844 0.060(6) Uiso 1 1 calc R . .
C3S C 0.66124(12) 0.5371(2) 0.55074(10) 0.0388(4) Uani 1 1 d . . .
H3S H 0.7001 0.5847 0.6071 0.044(5) Uiso 1 1 calc R . .
C5S C 0.55961(12) 0.3247(2) 0.45742(11) 0.0385(4) Uani 1 1 d . . .
H5S H 0.5283 0.2227 0.4504 0.051(5) Uiso 1 1 calc R . .
C4S C 0.61613(13) 0.3894(2) 0.54028(10) 0.0413(4) Uani 1 1 d . . .
H4S H 0.6237 0.3329 0.5892 0.059(6) Uiso 1 1 calc R . .


_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
O1A C1A 1.3791(17) . ?
O1A H11A 0.8400 . ?
C4B C5B 1.3927(18) . ?
C4B C3B 1.3946(19) . ?
C4B N1B 1.4219(17) . ?
C1B O1B 1.3684(16) . ?
C1B C6B 1.3884(19) . ?
C1B C2B 1.3912(19) . ?
O1B H11B 0.8400 . ?
N1B C7B 1.3478(17) . ?
N1B H1B 0.8800 . ?
N1A C7A 1.3485(18) . ?
N1A C4A 1.4145(17) . ?
N1A H1A 0.8800 . ?
C3B C2B 1.3846(19) . ?
C3B H3B 0.9500 . ?
C1A C6A 1.383(2) . ?
C1A C2A 1.3930(19) . ?
O2B C7B 1.2357(16) . ?
C4A C5A 1.3948(19) . ?
C4A C3A 1.3962(19) . ?
C3A C2A 1.383(2) . ?
C3A H3A 0.9500 . ?
C2B H2B 0.9500 . ?
C5B C6B 1.3862(19) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
O2A C7A 1.2333(17) . ?
C6A C5A 1.392(2) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.505(2) . ?
N1S C1S 1.332(2) . ?
N1S C5S 1.340(2) . ?
C2A H2A 0.9500 . ?
C7B C8B 1.500(2) . ?
C5A H5A 0.9500 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C8B H8B1 0.9800 . ?
C8B H8B3 0.9800 . ?
C8B H8B2 0.9800 . ?
C1S C2S 1.378(2) . ?
C1S H1S 0.9500 . ?
C2S C3S 1.371(2) . ?
C2S H2S 0.9500 . ?
C3S C4S 1.374(2) . ?
C3S H3S 0.9500 . ?
C5S C4S 1.379(2) . ?
C5S H5S 0.9500 . ?
C4S H4S 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
C1A O1A H11A 109.5 . . ?
C5B C4B C3B 118.76(12) . . ?
C5B C4B N1B 123.12(12) . . ?
C3B C4B N1B 118.06(12) . . ?
O1B C1B C6B 117.56(12) . . ?
O1B C1B C2B 123.01(13) . . ?
C6B C1B C2B 119.42(12) . . ?
C1B O1B H11B 109.5 . . ?
C7B N1B C4B 126.90(11) . . ?
C7B N1B H1B 116.5 . . ?
C4B N1B H1B 116.5 . . ?
C7A N1A C4A 128.78(12) . . ?
C7A N1A H1A 115.6 . . ?
C4A N1A H1A 115.6 . . ?
C2B C3B C4B 120.92(12) . . ?
C2B C3B H3B 119.5 . . ?
C4B C3B H3B 119.5 . . ?
O1A C1A C6A 119.49(13) . . ?
O1A C1A C2A 121.15(13) . . ?
C6A C1A C2A 119.34(13) . . ?
C5A C4A C3A 118.56(13) . . ?
C5A C4A N1A 124.53(12) . . ?
C3A C4A N1A 116.91(12) . . ?
C2A C3A C4A 121.25(13) . . ?
C2A C3A H3A 119.4 . . ?
C4A C3A H3A 119.4 . . ?
C3B C2B C1B 119.95(13) . . ?
C3B C2B H2B 120.0 . . ?
C1B C2B H2B 120.0 . . ?
C6B C5B C4B 120.36(13) . . ?
C6B C5B H5B 119.8 . . ?
C4B C5B H5B 119.8 . . ?
C5B C6B C1B 120.56(12) . . ?
C5B C6B H6B 119.7 . . ?
C1B C6B H6B 119.7 . . ?
C1A C6A C5A 120.95(13) . . ?
C1A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
O2A C7A N1A 123.28(13) . . ?
O2A C7A C8A 121.31(13) . . ?
N1A C7A C8A 115.40(12) . . ?
C1S N1S C5S 117.24(13) . . ?
C3A C2A C1A 119.84(13) . . ?
C3A C2A H2A 120.1 . . ?
C1A C2A H2A 120.1 . . ?
O2B C7B N1B 122.45(13) . . ?
O2B C7B C8B 121.93(13) . . ?
N1B C7B C8B 115.62(12) . . ?
C6A C5A C4A 120.01(13) . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
H8B3 C8B H8B2 109.5 . . ?
N1S C1S C2S 123.49(15) . . ?
N1S C1S H1S 118.3 . . ?
C2S C1S H1S 118.3 . . ?
C3S C2S C1S 118.50(15) . . ?
C3S C2S H2S 120.7 . . ?
C1S C2S H2S 120.7 . . ?
C2S C3S C4S 119.13(15) . . ?
C2S C3S H3S 120.4 . . ?
C4S C3S H3S 120.4 . . ?
N1S C5S C4S 122.83(15) . . ?
N1S C5S H5S 118.6 . . ?
C4S C5S H5S 118.6 . . ?
C3S C4S C5S 118.81(15) . . ?
C3S C4S H4S 120.6 . . ?
C5S C4S H4S 120.6 . . ?

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
C5B C4B N1B C7B -29.5(2) . . . . ?
C3B C4B N1B C7B 153.15(14) . . . . ?
C5B C4B C3B C2B -1.2(2) . . . . ?
N1B C4B C3B C2B 176.31(13) . . . . ?
C7A N1A C4A C5A 0.3(2) . . . . ?
C7A N1A C4A C3A -179.58(14) . . . . ?
C5A C4A C3A C2A 1.5(2) . . . . ?
N1A C4A C3A C2A -178.58(13) . . . . ?
C4B C3B C2B C1B -0.4(2) . . . . ?
O1B C1B C2B C3B -179.58(14) . . . . ?
C6B C1B C2B C3B 1.6(2) . . . . ?
C3B C4B C5B C6B 1.6(2) . . . . ?
N1B C4B C5B C6B -175.77(13) . . . . ?
C4B C5B C6B C1B -0.4(2) . . . . ?
O1B C1B C6B C5B 179.92(13) . . . . ?
C2B C1B C6B C5B -1.2(2) . . . . ?
O1A C1A C6A C5A 179.38(13) . . . . ?
C2A C1A C6A C5A 1.1(2) . . . . ?
C4A N1A C7A O2A 1.3(2) . . . . ?
C4A N1A C7A C8A -177.88(13) . . . . ?
C4A C3A C2A C1A 0.4(2) . . . . ?
O1A C1A C2A C3A 179.98(13) . . . . ?
C6A C1A C2A C3A -1.7(2) . . . . ?
C4B N1B C7B O2B -3.1(2) . . . . ?
C4B N1B C7B C8B 176.97(14) . . . . ?
C1A C6A C5A C4A 0.9(2) . . . . ?
C3A C4A C5A C6A -2.2(2) . . . . ?
N1A C4A C5A C6A 177.93(14) . . . . ?
C5S N1S C1S C2S 0.0(2) . . . . ?
N1S C1S C2S C3S -0.3(3) . . . . ?
C1S C2S C3S C4S 0.5(2) . . . . ?
C1S N1S C5S C4S 0.0(2) . . . . ?
C2S C3S C4S C5S -0.5(2) . . . . ?
N1S C5S C4S C3S 0.2(3) . . . . ?

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
N1A H1A O2B 0.88 1.98 2.8569(15) 172.1 2
N1B H1B O2A 0.88 1.98 2.8506(15) 171.0 3_565
O1B H11B O1A 0.84 1.91 2.7412(15) 169.6 2_645
O1A H11A N1S 0.84 1.83 2.6580(16) 167.9 .

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        29.20
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_0204__200
_database_code_depnum_ccdc_archive 'CCDC 816889'
_audit_update_record             
;
2011-03-10 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
#TrackingRef '4592_web_deposit_cif_file_4_BorisA.Zakharov_1299780018.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Paracetamol pyridine solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H9 N O2), C5 H5 N'
_chemical_formula_sum            'C21 H23 N3 O4'
_chemical_formula_weight         381.42

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/C
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5367(16)
_cell_length_b                   8.3081(6)
_cell_length_c                   18.051(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.906(8)
_cell_angle_gamma                90.00
_cell_volume                     1978.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    7780
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      29.64

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18597
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_sigmaI/netI    0.0578
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         29.18
_reflns_number_total             5341
_reflns_number_gt                3081
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0449P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0114(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5341
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.0947
_refine_ls_wR_factor_gt          0.0815
_refine_ls_goodness_of_fit_ref   0.888
_refine_ls_restrained_S_all      0.888
_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
O1A O 0.43826(7) 0.37156(14) 0.21297(7) 0.0383(3) Uani 1 1 d . . .
H11A H 0.4697 0.3667 0.2677 0.079(7) Uiso 1 1 calc R . .
C4B C 0.17039(10) 0.04830(17) 0.25187(8) 0.0277(3) Uani 1 1 d . . .
C1B C 0.37513(10) -0.03649(18) 0.33828(9) 0.0300(3) Uani 1 1 d . . .
O1B O 0.47607(7) -0.07469(15) 0.38410(7) 0.0407(3) Uani 1 1 d . . .
H11B H 0.4950 -0.0935 0.3491 0.072(7) Uiso 1 1 calc R . .
N1B N 0.06714(8) 0.09786(16) 0.20350(7) 0.0326(3) Uani 1 1 d . . .
H1B H 0.0418 0.1227 0.1484 0.051(5) Uiso 1 1 calc R . .
N1A N 0.05550(9) 0.64040(15) 0.08794(7) 0.0310(3) Uani 1 1 d . . .
H1A H 0.0287 0.6105 0.1182 0.040(4) Uiso 1 1 calc R . .
C3B C 0.21056(10) -0.02231(18) 0.20676(9) 0.0310(3) Uani 1 1 d . . .
H3B H 0.1678 -0.0415 0.1459 0.033(4) Uiso 1 1 calc R . .
C1A C 0.34359(11) 0.43749(18) 0.18164(9) 0.0312(3) Uani 1 1 d . . .
O2B O 0.02931(8) 0.07324(16) 0.30807(7) 0.0472(3) Uani 1 1 d . . .
C4A C 0.15168(10) 0.57384(17) 0.11544(8) 0.0284(3) Uani 1 1 d . . .
C3A C 0.19294(11) 0.46845(19) 0.18611(9) 0.0328(3) Uani 1 1 d . . .
H3A H 0.1553 0.4430 0.2123 0.041(4) Uiso 1 1 calc R . .
C2B C 0.31186(11) -0.06501(18) 0.24923(9) 0.0323(3) Uani 1 1 d . . .
H2B H 0.3382 -0.1137 0.2176 0.032(4) Uiso 1 1 calc R . .
C5B C 0.23372(10) 0.07309(18) 0.34140(9) 0.0313(3) Uani 1 1 d . . .
H5B H 0.2072 0.1191 0.3734 0.039(4) Uiso 1 1 calc R . .
C6B C 0.33515(11) 0.03103(18) 0.38393(9) 0.0319(3) Uani 1 1 d . . .
H6B H 0.3777 0.0486 0.4450 0.040(4) Uiso 1 1 calc R . .
O2A O 0.02562(8) 0.79399(15) -0.02741(7) 0.0446(3) Uani 1 1 d . . .
C6A C 0.30264(11) 0.5396(2) 0.11044(10) 0.0372(4) Uani 1 1 d . . .
H6A H 0.3403 0.5638 0.0841 0.048(5) Uiso 1 1 calc R . .
C7A C -0.00068(10) 0.74319(19) 0.02181(9) 0.0319(3) Uani 1 1 d . . .
N1S N 0.54672(10) 0.40101(17) 0.38583(8) 0.0408(3) Uani 1 1 d . . .
C2A C 0.28742(11) 0.40022(19) 0.21894(9) 0.0339(3) Uani 1 1 d . . .
H2A H 0.3139 0.3280 0.2669 0.040(4) Uiso 1 1 calc R . .
C7B C 0.00407(11) 0.11088(19) 0.23302(9) 0.0331(3) Uani 1 1 d . . .
C5A C 0.20724(11) 0.6073(2) 0.07679(9) 0.0364(3) Uani 1 1 d . . .
H5A H 0.1799 0.6764 0.0275 0.045(5) Uiso 1 1 calc R . .
C8A C -0.09907(11) 0.7952(2) 0.01188(10) 0.0394(4) Uani 1 1 d . . .
H8A1 H -0.0990 0.9123 0.0183 0.071(6) Uiso 1 1 calc R . .
H8A2 H -0.1066 0.7432 0.0569 0.063(6) Uiso 1 1 calc R . .
H8A3 H -0.1557 0.7639 -0.0460 0.069(6) Uiso 1 1 calc R . .
C8B C -0.09992(11) 0.1741(2) 0.16861(11) 0.0439(4) Uani 1 1 d . . .
H8B1 H -0.0946 0.2838 0.1516 0.106(9) Uiso 1 1 calc R . .
H8B3 H -0.1408 0.1748 0.1953 0.083(7) Uiso 1 1 calc R . .
H8B2 H -0.1323 0.1048 0.1168 0.108(9) Uiso 1 1 calc R . .
C1S C 0.59197(13) 0.5428(2) 0.39854(10) 0.0434(4) Uani 1 1 d . . .
H1S H 0.5842 0.5978 0.3492 0.061(6) Uiso 1 1 calc R . .
C2S C 0.64921(13) 0.6142(2) 0.47878(11) 0.0449(4) Uani 1 1 d . . .
H2S H 0.6800 0.7160 0.4846 0.066(6) Uiso 1 1 calc R . .
C3S C 0.66109(13) 0.5364(2) 0.55009(11) 0.0454(4) Uani 1 1 d . . .
H3S H 0.7001 0.5835 0.6064 0.062(6) Uiso 1 1 calc R . .
C5S C 0.55925(13) 0.3254(2) 0.45649(12) 0.0453(4) Uani 1 1 d . . .
H5S H 0.5278 0.2237 0.4492 0.058(5) Uiso 1 1 calc R . .
C4S C 0.61607(14) 0.3895(2) 0.53954(11) 0.0482(4) Uani 1 1 d . . .
H4S H 0.6237 0.3327 0.5884 0.070(6) Uiso 1 1 calc R . .


_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
O1A C1A 1.3798(17) . ?
O1A H11A 0.8400 . ?
C4B C3B 1.3907(19) . ?
C4B C5B 1.3934(18) . ?
C4B N1B 1.4229(17) . ?
C1B O1B 1.3686(17) . ?
C1B C6B 1.386(2) . ?
C1B C2B 1.3914(19) . ?
O1B H11B 0.8400 . ?
N1B C7B 1.3445(18) . ?
N1B H1B 0.8800 . ?
N1A C7A 1.3471(18) . ?
N1A C4A 1.4146(18) . ?
N1A H1A 0.8800 . ?
C3B C2B 1.384(2) . ?
C3B H3B 0.9500 . ?
C1A C6A 1.383(2) . ?
C1A C2A 1.390(2) . ?
O2B C7B 1.2351(17) . ?
C4A C3A 1.393(2) . ?
C4A C5A 1.3951(19) . ?
C3A C2A 1.381(2) . ?
C3A H3A 0.9500 . ?
C2B H2B 0.9500 . ?
C5B C6B 1.384(2) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
O2A C7A 1.2320(17) . ?
C6A C5A 1.390(2) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.505(2) . ?
N1S C1S 1.328(2) . ?
N1S C5S 1.340(2) . ?
C2A H2A 0.9500 . ?
C7B C8B 1.501(2) . ?
C5A H5A 0.9500 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C8B H8B1 0.9800 . ?
C8B H8B3 0.9800 . ?
C8B H8B2 0.9800 . ?
C1S C2S 1.371(2) . ?
C1S H1S 0.9500 . ?
C2S C3S 1.363(2) . ?
C2S H2S 0.9500 . ?
C3S C4S 1.369(3) . ?
C3S H3S 0.9500 . ?
C5S C4S 1.382(2) . ?
C5S H5S 0.9500 . ?
C4S H4S 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
C1A O1A H11A 109.5 . . ?
C3B C4B C5B 118.76(13) . . ?
C3B C4B N1B 118.17(12) . . ?
C5B C4B N1B 123.02(12) . . ?
O1B C1B C6B 117.72(12) . . ?
O1B C1B C2B 122.89(13) . . ?
C6B C1B C2B 119.39(13) . . ?
C1B O1B H11B 109.5 . . ?
C7B N1B C4B 126.98(12) . . ?
C7B N1B H1B 116.5 . . ?
C4B N1B H1B 116.5 . . ?
C7A N1A C4A 128.93(12) . . ?
C7A N1A H1A 115.5 . . ?
C4A N1A H1A 115.5 . . ?
C2B C3B C4B 120.98(13) . . ?
C2B C3B H3B 119.5 . . ?
C4B C3B H3B 119.5 . . ?
O1A C1A C6A 119.44(13) . . ?
O1A C1A C2A 121.28(13) . . ?
C6A C1A C2A 119.26(14) . . ?
C3A C4A C5A 118.45(13) . . ?
C3A C4A N1A 117.17(12) . . ?
C5A C4A N1A 124.38(13) . . ?
C2A C3A C4A 121.42(13) . . ?
C2A C3A H3A 119.3 . . ?
C4A C3A H3A 119.3 . . ?
C3B C2B C1B 119.91(13) . . ?
C3B C2B H2B 120.0 . . ?
C1B C2B H2B 120.0 . . ?
C6B C5B C4B 120.33(13) . . ?
C6B C5B H5B 119.8 . . ?
C4B C5B H5B 119.8 . . ?
C5B C6B C1B 120.61(13) . . ?
C5B C6B H6B 119.7 . . ?
C1B C6B H6B 119.7 . . ?
C1A C6A C5A 121.01(14) . . ?
C1A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
O2A C7A N1A 123.34(13) . . ?
O2A C7A C8A 121.24(13) . . ?
N1A C7A C8A 115.41(12) . . ?
C1S N1S C5S 116.98(14) . . ?
C3A C2A C1A 119.85(14) . . ?
C3A C2A H2A 120.1 . . ?
C1A C2A H2A 120.1 . . ?
O2B C7B N1B 122.61(13) . . ?
O2B C7B C8B 121.74(13) . . ?
N1B C7B C8B 115.65(13) . . ?
C6A C5A C4A 119.98(14) . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
H8B3 C8B H8B2 109.5 . . ?
N1S C1S C2S 123.72(16) . . ?
N1S C1S H1S 118.1 . . ?
C2S C1S H1S 118.1 . . ?
C3S C2S C1S 118.73(17) . . ?
C3S C2S H2S 120.6 . . ?
C1S C2S H2S 120.6 . . ?
C2S C3S C4S 119.17(16) . . ?
C2S C3S H3S 120.4 . . ?
C4S C3S H3S 120.4 . . ?
N1S C5S C4S 122.67(16) . . ?
N1S C5S H5S 118.7 . . ?
C4S C5S H5S 118.7 . . ?
C3S C4S C5S 118.73(16) . . ?
C3S C4S H4S 120.6 . . ?
C5S C4S H4S 120.6 . . ?

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
C3B C4B N1B C7B 153.21(15) . . . . ?
C5B C4B N1B C7B -29.4(2) . . . . ?
C5B C4B C3B C2B -1.1(2) . . . . ?
N1B C4B C3B C2B 176.41(14) . . . . ?
C7A N1A C4A C3A -179.50(14) . . . . ?
C7A N1A C4A C5A 0.7(2) . . . . ?
C5A C4A C3A C2A 1.3(2) . . . . ?
N1A C4A C3A C2A -178.53(13) . . . . ?
C4B C3B C2B C1B -0.4(2) . . . . ?
O1B C1B C2B C3B -179.53(14) . . . . ?
C6B C1B C2B C3B 1.6(2) . . . . ?
C3B C4B C5B C6B 1.3(2) . . . . ?
N1B C4B C5B C6B -176.03(14) . . . . ?
C4B C5B C6B C1B -0.1(2) . . . . ?
O1B C1B C6B C5B 179.72(14) . . . . ?
C2B C1B C6B C5B -1.3(2) . . . . ?
O1A C1A C6A C5A 179.57(14) . . . . ?
C2A C1A C6A C5A 1.1(2) . . . . ?
C4A N1A C7A O2A 1.2(2) . . . . ?
C4A N1A C7A C8A -178.06(14) . . . . ?
C4A C3A C2A C1A 0.5(2) . . . . ?
O1A C1A C2A C3A 179.91(13) . . . . ?
C6A C1A C2A C3A -1.7(2) . . . . ?
C4B N1B C7B O2B -3.1(2) . . . . ?
C4B N1B C7B C8B 177.10(14) . . . . ?
C1A C6A C5A C4A 0.6(2) . . . . ?
C3A C4A C5A C6A -1.8(2) . . . . ?
N1A C4A C5A C6A 177.97(14) . . . . ?
C5S N1S C1S C2S -0.4(2) . . . . ?
N1S C1S C2S C3S 0.1(3) . . . . ?
C1S C2S C3S C4S 0.3(3) . . . . ?
C1S N1S C5S C4S 0.1(2) . . . . ?
C2S C3S C4S C5S -0.5(3) . . . . ?
N1S C5S C4S C3S 0.3(3) . . . . ?

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
N1A H1A O2B 0.88 1.99 2.8610(15) 172.4 2
N1B H1B O2A 0.88 1.98 2.8540(16) 171.2 3_565
O1B H11B O1A 0.84 1.91 2.7399(16) 169.7 2_645
O1A H11A N1S 0.84 1.83 2.6603(17) 167.5 .

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        29.18
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_0104__225
_database_code_depnum_ccdc_archive 'CCDC 816890'
_audit_update_record             
;
2011-03-10 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
#TrackingRef '4593_web_deposit_cif_file_5_BorisA.Zakharov_1299780018.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Paracetamol pyridine solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H9 N O2), C5 H5 N'
_chemical_formula_sum            'C21 H23 N3 O4'
_chemical_formula_weight         381.42

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/C
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5427(16)
_cell_length_b                   8.3248(6)
_cell_length_c                   18.084(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.851(8)
_cell_angle_gamma                90.00
_cell_volume                     1987.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    225(2)
_cell_measurement_reflns_used    7347
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      29.58

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      225(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18685
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         29.23
_reflns_number_total             5363
_reflns_number_gt                2915
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0458P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0111(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5363
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.0983
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   0.885
_refine_ls_restrained_S_all      0.885
_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
O1A O 0.43806(8) 0.37350(15) 0.21254(7) 0.0442(3) Uani 1 1 d . . .
H11A H 0.4692 0.3687 0.2665 0.092(8) Uiso 1 1 calc R . .
C4B C 0.17048(10) 0.04897(18) 0.25205(9) 0.0310(3) Uani 1 1 d . . .
C1B C 0.37483(11) -0.03588(19) 0.33826(9) 0.0341(3) Uani 1 1 d . . .
O1B O 0.47560(8) -0.07441(16) 0.38416(7) 0.0466(3) Uani 1 1 d . . .
H11B H 0.4949 -0.0905 0.3498 0.077(7) Uiso 1 1 calc R . .
N1B N 0.06741(9) 0.09889(16) 0.20389(8) 0.0367(3) Uani 1 1 d . . .
H1B H 0.0425 0.1234 0.1495 0.051(5) Uiso 1 1 calc R . .
N1A N 0.05556(9) 0.64125(16) 0.08781(7) 0.0352(3) Uani 1 1 d . . .
H1A H 0.0292 0.6120 0.1179 0.041(4) Uiso 1 1 calc R . .
C3B C 0.21061(11) -0.02108(19) 0.20709(9) 0.0354(3) Uani 1 1 d . . .
H3B H 0.1685 -0.0396 0.1470 0.043(4) Uiso 1 1 calc R . .
C1A C 0.34340(11) 0.43938(19) 0.18133(9) 0.0354(3) Uani 1 1 d . . .
O2B O 0.02927(8) 0.07491(17) 0.30798(7) 0.0534(3) Uani 1 1 d . . .
C4A C 0.15166(11) 0.57501(18) 0.11522(9) 0.0320(3) Uani 1 1 d . . .
C3A C 0.19291(11) 0.47044(19) 0.18589(9) 0.0374(4) Uani 1 1 d . . .
H3A H 0.1557 0.4457 0.2119 0.048(5) Uiso 1 1 calc R . .
C2B C 0.31182(11) -0.06403(19) 0.24952(9) 0.0364(3) Uani 1 1 d . . .
H2B H 0.3379 -0.1122 0.2183 0.044(4) Uiso 1 1 calc R . .
C5B C 0.23366(11) 0.07348(19) 0.34136(9) 0.0357(3) Uani 1 1 d . . .
H5B H 0.2073 0.1190 0.3730 0.040(4) Uiso 1 1 calc R . .
C6B C 0.33487(11) 0.0313(2) 0.38381(9) 0.0367(3) Uani 1 1 d . . .
H6B H 0.3769 0.0483 0.4441 0.045(5) Uiso 1 1 calc R . .
O2A O 0.02531(9) 0.79351(16) -0.02751(7) 0.0511(3) Uani 1 1 d . . .
C6A C 0.30254(12) 0.5405(2) 0.11032(10) 0.0427(4) Uani 1 1 d . . .
H6A H 0.3397 0.5641 0.0842 0.050(5) Uiso 1 1 calc R . .
C7A C -0.00094(11) 0.74328(19) 0.02166(9) 0.0363(3) Uani 1 1 d . . .
N1S N 0.54671(10) 0.40255(18) 0.38522(9) 0.0466(3) Uani 1 1 d . . .
C2A C 0.28729(11) 0.4022(2) 0.21867(9) 0.0387(4) Uani 1 1 d . . .
H2A H 0.3135 0.3309 0.2660 0.051(5) Uiso 1 1 calc R . .
C7B C 0.00431(11) 0.1123(2) 0.23327(10) 0.0369(3) Uani 1 1 d . . .
C5A C 0.20713(12) 0.6081(2) 0.07667(10) 0.0410(4) Uani 1 1 d . . .
H5A H 0.1801 0.6761 0.0279 0.051(5) Uiso 1 1 calc R . .
C8A C -0.09911(12) 0.7953(2) 0.01172(10) 0.0443(4) Uani 1 1 d . . .
H8A1 H -0.0989 0.9110 0.0182 0.089(8) Uiso 1 1 calc R . .
H8A2 H -0.1067 0.7438 0.0560 0.074(6) Uiso 1 1 calc R . .
H8A3 H -0.1550 0.7646 -0.0455 0.086(7) Uiso 1 1 calc R . .
C8B C -0.09955(12) 0.1751(2) 0.16865(11) 0.0501(5) Uani 1 1 d . . .
H8B1 H -0.0944 0.2848 0.1532 0.134(11) Uiso 1 1 calc R . .
H8B3 H -0.1410 0.1726 0.1941 0.086(7) Uiso 1 1 calc R . .
H8B2 H -0.1304 0.1086 0.1168 0.116(10) Uiso 1 1 calc R . .
C1S C 0.59246(14) 0.5434(2) 0.39889(11) 0.0501(4) Uani 1 1 d . . .
H1S H 0.5853 0.5984 0.3505 0.067(6) Uiso 1 1 calc R . .
C2S C 0.64938(14) 0.6139(2) 0.47887(12) 0.0529(4) Uani 1 1 d . . .
H2S H 0.6799 0.7145 0.4850 0.083(7) Uiso 1 1 calc R . .
C3S C 0.66087(14) 0.5354(2) 0.54929(11) 0.0523(4) Uani 1 1 d . . .
H3S H 0.6996 0.5812 0.6050 0.066(6) Uiso 1 1 calc R . .
C5S C 0.55900(14) 0.3261(2) 0.45571(13) 0.0530(5) Uani 1 1 d . . .
H5S H 0.5278 0.2257 0.4483 0.065(6) Uiso 1 1 calc R . .
C4S C 0.61581(15) 0.3896(2) 0.53867(12) 0.0557(5) Uani 1 1 d . . .
H4S H 0.6232 0.3334 0.5868 0.081(7) Uiso 1 1 calc R . .


_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
O1A C1A 1.3812(18) . ?
O1A H11A 0.8300 . ?
C4B C3B 1.388(2) . ?
C4B C5B 1.3930(19) . ?
C4B N1B 1.4230(18) . ?
C1B O1B 1.3686(17) . ?
C1B C6B 1.384(2) . ?
C1B C2B 1.389(2) . ?
O1B H11B 0.8300 . ?
N1B C7B 1.3441(18) . ?
N1B H1B 0.8700 . ?
N1A C7A 1.3472(19) . ?
N1A C4A 1.4141(18) . ?
N1A H1A 0.8700 . ?
C3B C2B 1.385(2) . ?
C3B H3B 0.9400 . ?
C1A C6A 1.378(2) . ?
C1A C2A 1.391(2) . ?
O2B C7B 1.2327(18) . ?
C4A C3A 1.392(2) . ?
C4A C5A 1.393(2) . ?
C3A C2A 1.381(2) . ?
C3A H3A 0.9400 . ?
C2B H2B 0.9400 . ?
C5B C6B 1.383(2) . ?
C5B H5B 0.9400 . ?
C6B H6B 0.9400 . ?
O2A C7A 1.2308(18) . ?
C6A C5A 1.390(2) . ?
C6A H6A 0.9400 . ?
C7A C8A 1.503(2) . ?
N1S C1S 1.326(2) . ?
N1S C5S 1.345(2) . ?
C2A H2A 0.9400 . ?
C7B C8B 1.501(2) . ?
C5A H5A 0.9400 . ?
C8A H8A1 0.9700 . ?
C8A H8A2 0.9700 . ?
C8A H8A3 0.9700 . ?
C8B H8B1 0.9700 . ?
C8B H8B3 0.9700 . ?
C8B H8B2 0.9700 . ?
C1S C2S 1.367(2) . ?
C1S H1S 0.9400 . ?
C2S C3S 1.357(3) . ?
C2S H2S 0.9400 . ?
C3S C4S 1.363(3) . ?
C3S H3S 0.9400 . ?
C5S C4S 1.383(3) . ?
C5S H5S 0.9400 . ?
C4S H4S 0.9400 . ?

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
C1A O1A H11A 109.5 . . ?
C3B C4B C5B 118.76(13) . . ?
C3B C4B N1B 118.23(12) . . ?
C5B C4B N1B 122.95(13) . . ?
O1B C1B C6B 117.58(13) . . ?
O1B C1B C2B 122.99(14) . . ?
C6B C1B C2B 119.42(13) . . ?
C1B O1B H11B 109.5 . . ?
C7B N1B C4B 127.08(12) . . ?
C7B N1B H1B 116.5 . . ?
C4B N1B H1B 116.5 . . ?
C7A N1A C4A 129.06(13) . . ?
C7A N1A H1A 115.5 . . ?
C4A N1A H1A 115.5 . . ?
C2B C3B C4B 120.95(13) . . ?
C2B C3B H3B 119.5 . . ?
C4B C3B H3B 119.5 . . ?
C6A C1A O1A 119.41(14) . . ?
C6A C1A C2A 119.31(14) . . ?
O1A C1A C2A 121.26(14) . . ?
C3A C4A C5A 118.46(14) . . ?
C3A C4A N1A 117.08(13) . . ?
C5A C4A N1A 124.46(13) . . ?
C2A C3A C4A 121.42(14) . . ?
C2A C3A H3A 119.3 . . ?
C4A C3A H3A 119.3 . . ?
C3B C2B C1B 119.91(13) . . ?
C3B C2B H2B 120.0 . . ?
C1B C2B H2B 120.0 . . ?
C6B C5B C4B 120.38(14) . . ?
C6B C5B H5B 119.8 . . ?
C4B C5B H5B 119.8 . . ?
C5B C6B C1B 120.55(13) . . ?
C5B C6B H6B 119.7 . . ?
C1B C6B H6B 119.7 . . ?
C1A C6A C5A 121.03(14) . . ?
C1A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
O2A C7A N1A 123.12(14) . . ?
O2A C7A C8A 121.23(14) . . ?
N1A C7A C8A 115.64(13) . . ?
C1S N1S C5S 116.61(15) . . ?
C3A C2A C1A 119.75(14) . . ?
C3A C2A H2A 120.1 . . ?
C1A C2A H2A 120.1 . . ?
O2B C7B N1B 122.61(14) . . ?
O2B C7B C8B 121.89(14) . . ?
N1B C7B C8B 115.50(13) . . ?
C6A C5A C4A 119.99(14) . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
H8B3 C8B H8B2 109.5 . . ?
N1S C1S C2S 124.12(17) . . ?
N1S C1S H1S 117.9 . . ?
C2S C1S H1S 117.9 . . ?
C3S C2S C1S 118.54(18) . . ?
C3S C2S H2S 120.7 . . ?
C1S C2S H2S 120.7 . . ?
C2S C3S C4S 119.56(17) . . ?
C2S C3S H3S 120.2 . . ?
C4S C3S H3S 120.2 . . ?
N1S C5S C4S 122.51(17) . . ?
N1S C5S H5S 118.7 . . ?
C4S C5S H5S 118.7 . . ?
C3S C4S C5S 118.65(17) . . ?
C3S C4S H4S 120.7 . . ?
C5S C4S H4S 120.7 . . ?

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
C3B C4B N1B C7B 153.45(16) . . . . ?
C5B C4B N1B C7B -29.4(2) . . . . ?
C5B C4B C3B C2B -0.9(2) . . . . ?
N1B C4B C3B C2B 176.40(14) . . . . ?
C7A N1A C4A C3A -179.44(15) . . . . ?
C7A N1A C4A C5A 0.9(2) . . . . ?
C5A C4A C3A C2A 1.1(2) . . . . ?
N1A C4A C3A C2A -178.63(14) . . . . ?
C4B C3B C2B C1B -0.5(2) . . . . ?
O1B C1B C2B C3B -179.62(15) . . . . ?
C6B C1B C2B C3B 1.7(2) . . . . ?
C3B C4B C5B C6B 1.2(2) . . . . ?
N1B C4B C5B C6B -176.01(14) . . . . ?
C4B C5B C6B C1B 0.0(2) . . . . ?
O1B C1B C6B C5B 179.81(15) . . . . ?
C2B C1B C6B C5B -1.4(2) . . . . ?
O1A C1A C6A C5A 179.51(15) . . . . ?
C2A C1A C6A C5A 1.3(2) . . . . ?
C4A N1A C7A O2A 1.1(3) . . . . ?
C4A N1A C7A C8A -178.06(14) . . . . ?
C4A C3A C2A C1A 0.7(2) . . . . ?
C6A C1A C2A C3A -1.9(2) . . . . ?
O1A C1A C2A C3A 179.91(14) . . . . ?
C4B N1B C7B O2B -3.0(3) . . . . ?
C4B N1B C7B C8B 177.39(15) . . . . ?
C1A C6A C5A C4A 0.5(3) . . . . ?
C3A C4A C5A C6A -1.7(2) . . . . ?
N1A C4A C5A C6A 177.99(15) . . . . ?
C5S N1S C1S C2S -0.5(3) . . . . ?
N1S C1S C2S C3S 0.4(3) . . . . ?
C1S C2S C3S C4S 0.0(3) . . . . ?
C1S N1S C5S C4S 0.3(3) . . . . ?
C2S C3S C4S C5S -0.3(3) . . . . ?
N1S C5S C4S C3S 0.1(3) . . . . ?

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
N1A H1A O2B 0.87 2.00 2.8667(16) 172.5 2
N1B H1B O2A 0.87 2.00 2.8639(16) 171.4 3_565
O1B H11B O1A 0.83 1.92 2.7430(17) 170.4 2_645
O1A H11A N1S 0.83 1.85 2.6639(18) 167.7 .

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        29.23
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.035
####################################################################### 
# 
# 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_0104__250
_database_code_depnum_ccdc_archive 'CCDC 816891'
_audit_update_record             
;
2011-03-10 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
#TrackingRef '4594_web_deposit_cif_file_6_BorisA.Zakharov_1299780018.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Paracetamol pyridine solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H9 N O2), C5 H5 N'
_chemical_formula_sum            'C21 H23 N3 O4'
_chemical_formula_weight         381.42

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/C
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5486(17)
_cell_length_b                   8.3370(7)
_cell_length_c                   18.116(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.807(8)
_cell_angle_gamma                90.00
_cell_volume                     1995.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    6744
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      29.63

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18770
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         29.18
_reflns_number_total             5386
_reflns_number_gt                2702
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0459P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0117(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5386
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1110
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1008
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   0.863
_refine_ls_restrained_S_all      0.863
_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
O1A O 0.43774(8) 0.37562(16) 0.21216(8) 0.0508(3) Uani 1 1 d . . .
H11A H 0.4692 0.3727 0.2660 0.095(9) Uiso 1 1 calc R . .
C4B C 0.17069(11) 0.05035(19) 0.25241(9) 0.0347(3) Uani 1 1 d . . .
C1B C 0.37447(11) -0.0354(2) 0.33831(10) 0.0387(4) Uani 1 1 d . . .
O1B O 0.47524(8) -0.07391(17) 0.38420(8) 0.0529(3) Uani 1 1 d . . .
H11B H 0.4941 -0.0931 0.3499 0.086(8) Uiso 1 1 calc R . .
N1B N 0.06773(9) 0.09996(17) 0.20426(8) 0.0411(3) Uani 1 1 d . . .
H1B H 0.0430 0.1241 0.1500 0.060(6) Uiso 1 1 calc R . .
N1A N 0.05542(9) 0.64239(17) 0.08769(8) 0.0400(3) Uani 1 1 d . . .
H1A H 0.0292 0.6136 0.1179 0.045(5) Uiso 1 1 calc R . .
C3B C 0.21085(12) -0.0200(2) 0.20758(10) 0.0396(4) Uani 1 1 d . . .
H3B H 0.1688 -0.0386 0.1476 0.051(5) Uiso 1 1 calc R . .
C1A C 0.34319(11) 0.4413(2) 0.18095(10) 0.0398(4) Uani 1 1 d . . .
O2B O 0.02934(9) 0.07698(18) 0.30798(7) 0.0606(4) Uani 1 1 d . . .
C4A C 0.15156(11) 0.57628(19) 0.11501(9) 0.0360(4) Uani 1 1 d . . .
C3A C 0.19292(12) 0.4726(2) 0.18556(10) 0.0422(4) Uani 1 1 d . . .
H3A H 0.1558 0.4479 0.2116 0.050(5) Uiso 1 1 calc R . .
C2B C 0.31163(11) -0.0631(2) 0.24988(10) 0.0406(4) Uani 1 1 d . . .
H2B H 0.3377 -0.1112 0.2188 0.047(5) Uiso 1 1 calc R . .
C5B C 0.23340(11) 0.0741(2) 0.34129(9) 0.0397(4) Uani 1 1 d . . .
H5B H 0.2071 0.1191 0.3729 0.051(5) Uiso 1 1 calc R . .
C6B C 0.33442(12) 0.0317(2) 0.38349(10) 0.0416(4) Uani 1 1 d . . .
H6B H 0.3764 0.0488 0.4436 0.051(5) Uiso 1 1 calc R . .
O2A O 0.02479(9) 0.79321(17) -0.02786(8) 0.0576(4) Uani 1 1 d . . .
C6A C 0.30197(13) 0.5416(2) 0.10980(11) 0.0479(4) Uani 1 1 d . . .
H6A H 0.3389 0.5651 0.0835 0.055(5) Uiso 1 1 calc R . .
C7A C -0.00110(12) 0.7436(2) 0.02146(10) 0.0411(4) Uani 1 1 d . . .
N1S N 0.54632(11) 0.4044(2) 0.38431(10) 0.0532(4) Uani 1 1 d . . .
C2A C 0.28739(12) 0.4049(2) 0.21834(10) 0.0439(4) Uani 1 1 d . . .
H2A H 0.3138 0.3344 0.2659 0.054(5) Uiso 1 1 calc R . .
C7B C 0.00452(12) 0.1137(2) 0.23342(10) 0.0414(4) Uani 1 1 d . . .
C5A C 0.20682(12) 0.6085(2) 0.07644(11) 0.0466(4) Uani 1 1 d . . .
H5A H 0.1796 0.6759 0.0276 0.054(5) Uiso 1 1 calc R . .
C8A C -0.09922(12) 0.7949(2) 0.01171(11) 0.0497(4) Uani 1 1 d . . .
H8A1 H -0.0992 0.9104 0.0183 0.094(8) Uiso 1 1 calc R . .
H8A2 H -0.1068 0.7430 0.0559 0.087(7) Uiso 1 1 calc R . .
H8A3 H -0.1550 0.7645 -0.0454 0.098(8) Uiso 1 1 calc R . .
C8B C -0.09918(13) 0.1761(3) 0.16875(12) 0.0564(5) Uani 1 1 d . . .
H8B1 H -0.0939 0.2848 0.1524 0.137(11) Uiso 1 1 calc R . .
H8B3 H -0.1403 0.1757 0.1945 0.093(7) Uiso 1 1 calc R . .
H8B2 H -0.1303 0.1082 0.1176 0.118(10) Uiso 1 1 calc R . .
C1S C 0.59266(15) 0.5441(2) 0.39895(12) 0.0565(5) Uani 1 1 d . . .
H1S H 0.5861 0.5996 0.3511 0.078(7) Uiso 1 1 calc R . .
C2S C 0.64930(15) 0.6130(3) 0.47877(13) 0.0606(5) Uani 1 1 d . . .
H2S H 0.6799 0.7135 0.4852 0.093(8) Uiso 1 1 calc R . .
C3S C 0.66070(15) 0.5345(3) 0.54848(13) 0.0611(5) Uani 1 1 d . . .
H3S H 0.6997 0.5798 0.6042 0.083(7) Uiso 1 1 calc R . .
C5S C 0.55836(15) 0.3270(2) 0.45449(15) 0.0614(5) Uani 1 1 d . . .
H5S H 0.5269 0.2269 0.4467 0.079(7) Uiso 1 1 calc R . .
C4S C 0.61559(16) 0.3898(3) 0.53787(13) 0.0637(6) Uani 1 1 d . . .
H4S H 0.6229 0.3334 0.5858 0.094(8) Uiso 1 1 calc R . .


_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
O1A C1A 1.3800(19) . ?
O1A H11A 0.8300 . ?
C4B C5B 1.388(2) . ?
C4B C3B 1.389(2) . ?
C4B N1B 1.4222(19) . ?
C1B O1B 1.3697(18) . ?
C1B C6B 1.381(2) . ?
C1B C2B 1.387(2) . ?
O1B H11B 0.8300 . ?
N1B C7B 1.3437(19) . ?
N1B H1B 0.8700 . ?
N1A C7A 1.346(2) . ?
N1A C4A 1.4154(19) . ?
N1A H1A 0.8700 . ?
C3B C2B 1.381(2) . ?
C3B H3B 0.9400 . ?
C1A C6A 1.379(2) . ?
C1A C2A 1.387(2) . ?
O2B C7B 1.2319(19) . ?
C4A C3A 1.389(2) . ?
C4A C5A 1.390(2) . ?
C3A C2A 1.381(2) . ?
C3A H3A 0.9400 . ?
C2B H2B 0.9400 . ?
C5B C6B 1.382(2) . ?
C5B H5B 0.9400 . ?
C6B H6B 0.9400 . ?
O2A C7A 1.2291(18) . ?
C6A C5A 1.386(2) . ?
C6A H6A 0.9400 . ?
C7A C8A 1.502(2) . ?
N1S C1S 1.321(2) . ?
N1S C5S 1.348(3) . ?
C2A H2A 0.9400 . ?
C7B C8B 1.501(2) . ?
C5A H5A 0.9400 . ?
C8A H8A1 0.9700 . ?
C8A H8A2 0.9700 . ?
C8A H8A3 0.9700 . ?
C8B H8B1 0.9700 . ?
C8B H8B3 0.9700 . ?
C8B H8B2 0.9700 . ?
C1S C2S 1.362(3) . ?
C1S H1S 0.9400 . ?
C2S C3S 1.349(3) . ?
C2S H2S 0.9400 . ?
C3S C4S 1.357(3) . ?
C3S H3S 0.9400 . ?
C5S C4S 1.390(3) . ?
C5S H5S 0.9400 . ?
C4S H4S 0.9400 . ?

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
C1A O1A H11A 109.5 . . ?
C5B C4B C3B 118.75(14) . . ?
C5B C4B N1B 123.05(14) . . ?
C3B C4B N1B 118.16(13) . . ?
O1B C1B C6B 117.65(14) . . ?
O1B C1B C2B 123.10(14) . . ?
C6B C1B C2B 119.25(14) . . ?
C1B O1B H11B 109.5 . . ?
C7B N1B C4B 127.14(13) . . ?
C7B N1B H1B 116.4 . . ?
C4B N1B H1B 116.4 . . ?
C7A N1A C4A 128.96(13) . . ?
C7A N1A H1A 115.5 . . ?
C4A N1A H1A 115.5 . . ?
C2B C3B C4B 120.93(14) . . ?
C2B C3B H3B 119.5 . . ?
C4B C3B H3B 119.5 . . ?
C6A C1A O1A 119.57(14) . . ?
C6A C1A C2A 119.15(15) . . ?
O1A C1A C2A 121.26(15) . . ?
C3A C4A C5A 118.29(15) . . ?
C3A C4A N1A 117.11(13) . . ?
C5A C4A N1A 124.60(14) . . ?
C2A C3A C4A 121.44(15) . . ?
C2A C3A H3A 119.3 . . ?
C4A C3A H3A 119.3 . . ?
C3B C2B C1B 120.02(14) . . ?
C3B C2B H2B 120.0 . . ?
C1B C2B H2B 120.0 . . ?
C6B C5B C4B 120.26(14) . . ?
C6B C5B H5B 119.9 . . ?
C4B C5B H5B 119.9 . . ?
C1B C6B C5B 120.76(14) . . ?
C1B C6B H6B 119.6 . . ?
C5B C6B H6B 119.6 . . ?
C1A C6A C5A 120.98(15) . . ?
C1A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
O2A C7A N1A 123.27(15) . . ?
O2A C7A C8A 121.34(15) . . ?
N1A C7A C8A 115.39(14) . . ?
C1S N1S C5S 116.28(17) . . ?
C3A C2A C1A 119.86(15) . . ?
C3A C2A H2A 120.1 . . ?
C1A C2A H2A 120.1 . . ?
O2B C7B N1B 122.59(15) . . ?
O2B C7B C8B 121.93(14) . . ?
N1B C7B C8B 115.48(14) . . ?
C6A C5A C4A 120.25(16) . . ?
C6A C5A H5A 119.9 . . ?
C4A C5A H5A 119.9 . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
H8B3 C8B H8B2 109.5 . . ?
N1S C1S C2S 124.36(19) . . ?
N1S C1S H1S 117.8 . . ?
C2S C1S H1S 117.8 . . ?
C3S C2S C1S 118.8(2) . . ?
C3S C2S H2S 120.6 . . ?
C1S C2S H2S 120.6 . . ?
C2S C3S C4S 119.72(19) . . ?
C2S C3S H3S 120.1 . . ?
C4S C3S H3S 120.1 . . ?
N1S C5S C4S 122.41(19) . . ?
N1S C5S H5S 118.8 . . ?
C4S C5S H5S 118.8 . . ?
C3S C4S C5S 118.42(19) . . ?
C3S C4S H4S 120.8 . . ?
C5S C4S H4S 120.8 . . ?

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
C5B C4B N1B C7B -28.9(3) . . . . ?
C3B C4B N1B C7B 153.42(16) . . . . ?
C5B C4B C3B C2B -1.2(2) . . . . ?
N1B C4B C3B C2B 176.60(15) . . . . ?
C7A N1A C4A C3A -179.36(16) . . . . ?
C7A N1A C4A C5A 0.9(3) . . . . ?
C5A C4A C3A C2A 1.3(2) . . . . ?
N1A C4A C3A C2A -178.46(15) . . . . ?
C4B C3B C2B C1B -0.4(3) . . . . ?
O1B C1B C2B C3B -179.46(16) . . . . ?
C6B C1B C2B C3B 1.6(2) . . . . ?
C3B C4B C5B C6B 1.6(2) . . . . ?
N1B C4B C5B C6B -176.12(15) . . . . ?
O1B C1B C6B C5B 179.77(15) . . . . ?
C2B C1B C6B C5B -1.2(3) . . . . ?
C4B C5B C6B C1B -0.4(3) . . . . ?
O1A C1A C6A C5A 179.47(16) . . . . ?
C2A C1A C6A C5A 1.2(3) . . . . ?
C4A N1A C7A O2A 1.1(3) . . . . ?
C4A N1A C7A C8A -178.25(15) . . . . ?
C4A C3A C2A C1A 0.5(3) . . . . ?
C6A C1A C2A C3A -1.7(2) . . . . ?
O1A C1A C2A C3A -179.96(14) . . . . ?
C4B N1B C7B O2B -3.0(3) . . . . ?
C4B N1B C7B C8B 177.38(16) . . . . ?
C1A C6A C5A C4A 0.6(3) . . . . ?
C3A C4A C5A C6A -1.8(3) . . . . ?
N1A C4A C5A C6A 177.92(16) . . . . ?
C5S N1S C1S C2S -0.8(3) . . . . ?
N1S C1S C2S C3S 0.8(3) . . . . ?
C1S C2S C3S C4S -0.3(3) . . . . ?
C1S N1S C5S C4S 0.4(3) . . . . ?
C2S C3S C4S C5S -0.1(3) . . . . ?
N1S C5S C4S C3S 0.1(3) . . . . ?

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
N1A H1A O2B 0.87 2.00 2.8693(17) 172.6 2
N1B H1B O2A 0.87 2.01 2.8685(17) 171.4 3_565
O1B H11B O1A 0.83 1.93 2.7466(18) 169.3 2_645
O1A H11A N1S 0.83 1.84 2.6616(19) 169.3 .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.18
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.033
####################################################################### 
# 
# 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_3103__275
_database_code_depnum_ccdc_archive 'CCDC 816892'
_audit_update_record             
;
2011-03-10 deposited with the CCDC.
2015-08-26 downloaded from the CCDC.
;
#TrackingRef '4595_web_deposit_cif_file_7_BorisA.Zakharov_1299780018.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
Paracetamol pyridine solvate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C8 H9 N O2), C5 H5 N'
_chemical_formula_sum            'C21 H23 N3 O4'
_chemical_formula_weight         381.42

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/C
_symmetry_space_group_name_Hall  '-P 2ybc'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.5533(18)
_cell_length_b                   8.3475(7)
_cell_length_c                   18.151(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 121.742(9)
_cell_angle_gamma                90.00
_cell_volume                     2004.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    275(2)
_cell_measurement_reflns_used    6367
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      29.55

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      275(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            STOE
_diffrn_source_voltage           50
_diffrn_source_current           30
_diffrn_source_power             1.50
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18870
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0631
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.54
_diffrn_reflns_theta_max         29.20
_reflns_number_total             5416
_reflns_number_gt                2570
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'STOE X-AREA'
_computing_cell_refinement       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0488P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0118(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5416
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.0877
_refine_ls_goodness_of_fit_ref   0.868
_refine_ls_restrained_S_all      0.868
_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
O1A O 0.43747(9) 0.37813(18) 0.21168(9) 0.0581(4) Uani 1 1 d . . .
H11A H 0.4688 0.3767 0.2648 0.114(10) Uiso 1 1 calc R . .
C4B C 0.17084(11) 0.0515(2) 0.25272(10) 0.0388(4) Uani 1 1 d . . .
C1B C 0.37419(12) -0.0345(2) 0.33849(10) 0.0435(4) Uani 1 1 d . . .
O1B O 0.47476(8) -0.07353(19) 0.38418(8) 0.0598(4) Uani 1 1 d . . .
H11B H 0.4935 -0.0918 0.3504 0.086(8) Uiso 1 1 calc R . .
N1B N 0.06796(10) 0.10126(18) 0.20457(9) 0.0457(4) Uani 1 1 d . . .
H1B H 0.0437 0.1251 0.1511 0.067(6) Uiso 1 1 calc R . .
N1A N 0.05542(10) 0.64357(18) 0.08745(8) 0.0448(4) Uani 1 1 d . . .
H1A H 0.0297 0.6156 0.1174 0.049(5) Uiso 1 1 calc R . .
C3B C 0.21108(12) -0.0186(2) 0.20805(10) 0.0447(4) Uani 1 1 d . . .
H3B H 0.1697 -0.0367 0.1488 0.050(5) Uiso 1 1 calc R . .
C1A C 0.34281(12) 0.4434(2) 0.18048(11) 0.0455(4) Uani 1 1 d . . .
O2B O 0.02931(9) 0.0788(2) 0.30783(8) 0.0689(4) Uani 1 1 d . . .
C4A C 0.15140(12) 0.5777(2) 0.11475(10) 0.0407(4) Uani 1 1 d . . .
C3A C 0.19310(13) 0.4747(2) 0.18545(11) 0.0480(4) Uani 1 1 d . . .
H3A H 0.1566 0.4505 0.2114 0.057(5) Uiso 1 1 calc R . .
C2B C 0.31176(12) -0.0618(2) 0.25041(11) 0.0456(4) Uani 1 1 d . . .
H2B H 0.3377 -0.1093 0.2198 0.048(5) Uiso 1 1 calc R . .
C5B C 0.23327(12) 0.0747(2) 0.34132(10) 0.0447(4) Uani 1 1 d . . .
H5B H 0.2071 0.1191 0.3725 0.055(5) Uiso 1 1 calc R . .
C6B C 0.33401(12) 0.0322(2) 0.38345(10) 0.0472(4) Uani 1 1 d . . .
H6B H 0.3753 0.0487 0.4428 0.063(6) Uiso 1 1 calc R . .
O2A O 0.02430(10) 0.79299(18) -0.02817(8) 0.0647(4) Uani 1 1 d . . .
C6A C 0.30144(13) 0.5429(2) 0.10946(12) 0.0541(5) Uani 1 1 d . . .
H6A H 0.3379 0.5659 0.0834 0.063(5) Uiso 1 1 calc R . .
C7A C -0.00151(12) 0.7440(2) 0.02114(10) 0.0460(4) Uani 1 1 d . . .
N1S N 0.54621(12) 0.4062(2) 0.38371(10) 0.0598(4) Uani 1 1 d . . .
C2A C 0.28730(13) 0.4075(2) 0.21798(11) 0.0498(4) Uani 1 1 d . . .
H2A H 0.3136 0.3382 0.2651 0.054(5) Uiso 1 1 calc R . .
C7B C 0.00464(13) 0.1151(2) 0.23355(11) 0.0467(4) Uani 1 1 d . . .
C5A C 0.20639(13) 0.6093(2) 0.07618(12) 0.0527(5) Uani 1 1 d . . .
H5A H 0.1794 0.6755 0.0278 0.055(5) Uiso 1 1 calc R . .
C8A C -0.09938(13) 0.7951(3) 0.01156(12) 0.0561(5) Uani 1 1 d . . .
H8A1 H -0.0993 0.9092 0.0182 0.101(9) Uiso 1 1 calc R . .
H8A2 H -0.1069 0.7437 0.0552 0.100(8) Uiso 1 1 calc R . .
H8A3 H -0.1546 0.7651 -0.0448 0.100(8) Uiso 1 1 calc R . .
C8B C -0.09888(14) 0.1767(3) 0.16892(13) 0.0637(6) Uani 1 1 d . . .
H8B1 H -0.0938 0.2838 0.1523 0.144(12) Uiso 1 1 calc R . .
H8B3 H -0.1396 0.1769 0.1943 0.107(8) Uiso 1 1 calc R . .
H8B2 H -0.1296 0.1089 0.1187 0.149(13) Uiso 1 1 calc R . .
C1S C 0.59303(17) 0.5451(3) 0.39935(14) 0.0643(6) Uani 1 1 d . . .
H1S H 0.5868 0.6009 0.3524 0.088(7) Uiso 1 1 calc R . .
C2S C 0.64949(17) 0.6123(3) 0.47879(15) 0.0700(6) Uani 1 1 d . . .
H2S H 0.6801 0.7114 0.4855 0.116(10) Uiso 1 1 calc R . .
C3S C 0.66043(17) 0.5337(3) 0.54740(14) 0.0698(6) Uani 1 1 d . . .
H3S H 0.6989 0.5782 0.6024 0.100(8) Uiso 1 1 calc R . .
C5S C 0.55789(17) 0.3276(3) 0.45368(17) 0.0701(6) Uani 1 1 d . . .
H5S H 0.5263 0.2291 0.4458 0.093(8) Uiso 1 1 calc R . .
C4S C 0.61580(18) 0.3901(3) 0.53696(15) 0.0717(6) Uani 1 1 d . . .
H4S H 0.6235 0.3340 0.5844 0.102(8) Uiso 1 1 calc R . .


_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
O1A C1A 1.381(2) . ?
O1A H11A 0.8200 . ?
C4B C5B 1.387(2) . ?
C4B C3B 1.388(2) . ?
C4B N1B 1.423(2) . ?
C1B O1B 1.3696(19) . ?
C1B C6B 1.379(2) . ?
C1B C2B 1.385(2) . ?
O1B H11B 0.8200 . ?
N1B C7B 1.343(2) . ?
N1B H1B 0.8600 . ?
N1A C7A 1.347(2) . ?
N1A C4A 1.414(2) . ?
N1A H1A 0.8600 . ?
C3B C2B 1.381(2) . ?
C3B H3B 0.9300 . ?
C1A C6A 1.376(3) . ?
C1A C2A 1.384(2) . ?
O2B C7B 1.230(2) . ?
C4A C5A 1.386(2) . ?
C4A C3A 1.390(2) . ?
C3A C2A 1.378(2) . ?
C3A H3A 0.9300 . ?
C2B H2B 0.9300 . ?
C5B C6B 1.380(2) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
O2A C7A 1.228(2) . ?
C6A C5A 1.385(2) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.500(2) . ?
N1S C1S 1.318(3) . ?
N1S C5S 1.354(3) . ?
C2A H2A 0.9300 . ?
C7B C8B 1.499(2) . ?
C5A H5A 0.9300 . ?
C8A H8A1 0.9600 . ?
C8A H8A2 0.9600 . ?
C8A H8A3 0.9600 . ?
C8B H8B1 0.9600 . ?
C8B H8B3 0.9600 . ?
C8B H8B2 0.9600 . ?
C1S C2S 1.354(3) . ?
C1S H1S 0.9300 . ?
C2S C3S 1.337(3) . ?
C2S H2S 0.9300 . ?
C3S C4S 1.348(3) . ?
C3S H3S 0.9300 . ?
C5S C4S 1.391(3) . ?
C5S H5S 0.9300 . ?
C4S H4S 0.9300 . ?

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
C1A O1A H11A 109.5 . . ?
C5B C4B C3B 118.72(15) . . ?
C5B C4B N1B 123.13(14) . . ?
C3B C4B N1B 118.12(14) . . ?
O1B C1B C6B 117.79(15) . . ?
O1B C1B C2B 122.94(15) . . ?
C6B C1B C2B 119.26(15) . . ?
C1B O1B H11B 109.5 . . ?
C7B N1B C4B 127.13(14) . . ?
C7B N1B H1B 116.4 . . ?
C4B N1B H1B 116.4 . . ?
C7A N1A C4A 129.20(14) . . ?
C7A N1A H1A 115.4 . . ?
C4A N1A H1A 115.4 . . ?
C2B C3B C4B 120.85(15) . . ?
C2B C3B H3B 119.6 . . ?
C4B C3B H3B 119.6 . . ?
C6A C1A O1A 119.64(16) . . ?
C6A C1A C2A 119.07(16) . . ?
O1A C1A C2A 121.27(17) . . ?
C5A C4A C3A 118.18(16) . . ?
C5A C4A N1A 124.55(15) . . ?
C3A C4A N1A 117.28(14) . . ?
C2A C3A C4A 121.45(16) . . ?
C2A C3A H3A 119.3 . . ?
C4A C3A H3A 119.3 . . ?
C3B C2B C1B 120.06(15) . . ?
C3B C2B H2B 120.0 . . ?
C1B C2B H2B 120.0 . . ?
C6B C5B C4B 120.31(15) . . ?
C6B C5B H5B 119.8 . . ?
C4B C5B H5B 119.8 . . ?
C1B C6B C5B 120.77(15) . . ?
C1B C6B H6B 119.6 . . ?
C5B C6B H6B 119.6 . . ?
C1A C6A C5A 121.08(16) . . ?
C1A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
O2A C7A N1A 123.05(16) . . ?
O2A C7A C8A 121.45(16) . . ?
N1A C7A C8A 115.49(15) . . ?
C1S N1S C5S 115.96(18) . . ?
C3A C2A C1A 119.92(17) . . ?
C3A C2A H2A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
O2B C7B N1B 122.54(16) . . ?
O2B C7B C8B 121.99(15) . . ?
N1B C7B C8B 115.46(15) . . ?
C6A C5A C4A 120.26(17) . . ?
C6A C5A H5A 119.9 . . ?
C4A C5A H5A 119.9 . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
H8B3 C8B H8B2 109.5 . . ?
N1S C1S C2S 124.7(2) . . ?
N1S C1S H1S 117.7 . . ?
C2S C1S H1S 117.7 . . ?
C3S C2S C1S 118.8(2) . . ?
C3S C2S H2S 120.6 . . ?
C1S C2S H2S 120.6 . . ?
C2S C3S C4S 120.1(2) . . ?
C2S C3S H3S 119.9 . . ?
C4S C3S H3S 119.9 . . ?
N1S C5S C4S 121.9(2) . . ?
N1S C5S H5S 119.1 . . ?
C4S C5S H5S 119.1 . . ?
C3S C4S C5S 118.5(2) . . ?
C3S C4S H4S 120.7 . . ?
C5S C4S H4S 120.7 . . ?

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
C5B C4B N1B C7B -28.7(3) . . . . ?
C3B C4B N1B C7B 153.51(18) . . . . ?
C5B C4B C3B C2B -1.2(3) . . . . ?
N1B C4B C3B C2B 176.61(16) . . . . ?
C7A N1A C4A C5A 1.0(3) . . . . ?
C7A N1A C4A C3A -179.28(17) . . . . ?
C5A C4A C3A C2A 1.2(3) . . . . ?
N1A C4A C3A C2A -178.49(16) . . . . ?
C4B C3B C2B C1B -0.4(3) . . . . ?
O1B C1B C2B C3B -179.56(17) . . . . ?
C6B C1B C2B C3B 1.7(3) . . . . ?
C3B C4B C5B C6B 1.6(3) . . . . ?
N1B C4B C5B C6B -176.17(16) . . . . ?
O1B C1B C6B C5B 179.83(17) . . . . ?
C2B C1B C6B C5B -1.4(3) . . . . ?
C4B C5B C6B C1B -0.3(3) . . . . ?
O1A C1A C6A C5A 179.52(17) . . . . ?
C2A C1A C6A C5A 1.1(3) . . . . ?
C4A N1A C7A O2A 0.9(3) . . . . ?
C4A N1A C7A C8A -178.28(16) . . . . ?
C4A C3A C2A C1A 0.5(3) . . . . ?
C6A C1A C2A C3A -1.7(3) . . . . ?
O1A C1A C2A C3A 179.93(16) . . . . ?
C4B N1B C7B O2B -2.8(3) . . . . ?
C4B N1B C7B C8B 177.67(17) . . . . ?
C1A C6A C5A C4A 0.7(3) . . . . ?
C3A C4A C5A C6A -1.8(3) . . . . ?
N1A C4A C5A C6A 177.89(17) . . . . ?
C5S N1S C1S C2S -0.7(3) . . . . ?
N1S C1S C2S C3S 0.7(3) . . . . ?
C1S C2S C3S C4S 0.1(3) . . . . ?
C1S N1S C5S C4S 0.0(3) . . . . ?
C2S C3S C4S C5S -0.7(3) . . . . ?
N1S C5S C4S C3S 0.6(3) . . . . ?

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
N1A H1A O2B 0.86 2.02 2.8770(18) 172.9 2
N1B H1B O2A 0.86 2.02 2.8733(19) 171.6 3_565
O1B H11B O1A 0.82 1.94 2.7483(19) 169.2 2_645
O1A H11A N1S 0.82 1.85 2.666(2) 170.8 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.20
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.031


