#------------------------------------------------------------------------------
#$Date: 2016-03-26 19:23:19 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180432 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/01/7210137.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7210137
loop_
_publ_author_name
'Sander, John R. G.'
'Bučar, Dejan-Krešimir'
'Henry, Rodger F.'
'Giangiorgi, Brittany N.'
'Zhang, Geoff G. Z.'
'MacGillivray, Leonard R.'
_publ_section_title
;
 ‘Masked synthons’ in crystal engineering: insulated
 components in acetaminophen cocrystal hydrates
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              4816
_journal_paper_doi               10.1039/c3ce40159f
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C8 H9 O2 N1, 1.5(C12 H10 N2), 2(O1 H2)'
_chemical_formula_sum            'C26 H28 N4 O4'
_chemical_formula_weight         460.52
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.3410(10)
_cell_angle_beta                 99.5260(10)
_cell_angle_gamma                102.8040(10)
_cell_formula_units_Z            2
_cell_length_a                   9.2028(9)
_cell_length_b                   11.5290(12)
_cell_length_c                   11.7206(12)
_cell_measurement_reflns_used    8109
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5645
_cell_measurement_theta_min      2.3085
_cell_volume                     1190.1(2)
_computing_cell_refinement       'Apex2 v2.1-4 (Bruker, 2007)'
_computing_data_collection       'Apex2 v2.1-4 (Bruker, 2007)'
_computing_data_reduction        'Apex2 v2.1-4 (Bruker, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows v2.01'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0162
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13902
_diffrn_reflns_theta_full        27.57
_diffrn_reflns_theta_max         27.57
_diffrn_reflns_theta_min         1.77
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9956
_exptl_absorpt_correction_T_min  0.9740
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5375
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0358
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1398
_reflns_number_gt                4708
_reflns_number_total             5375
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            c3ce40159f.txt
_cod_data_source_block           xray3817_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7210137
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
O1 O 0.98934(8) 0.70730(6) 1.75529(6) 0.02195(18) Uani 1 1 d .
H1O H 1.0244 0.7740 1.7902 0.033 Uiso 1 1 calc R
O2 O 0.88998(9) 0.90361(6) 1.24352(6) 0.02330(19) Uani 1 1 d .
N1 N 0.90685(9) 0.71371(7) 1.27329(7) 0.01798(19) Uani 1 1 d .
H1 H 0.9073 0.6460 1.2385 0.022 Uiso 1 1 calc R
C1 C 0.96772(11) 0.71621(9) 1.63820(8) 0.0183(2) Uani 1 1 d .
C2 C 1.00127(12) 0.82400(9) 1.58958(9) 0.0205(2) Uani 1 1 d .
H2 H 1.0375 0.8951 1.6378 0.025 Uiso 1 1 calc R
C3 C 0.98108(12) 0.82640(8) 1.46962(8) 0.0204(2) Uani 1 1 d .
H3 H 1.0048 0.8989 1.4380 0.024 Uiso 1 1 calc R
C4 C 0.92520(11) 0.72028(9) 1.39645(8) 0.0173(2) Uani 1 1 d .
C5 C 0.88909(11) 0.61257(9) 1.44554(9) 0.0192(2) Uani 1 1 d .
H5 H 0.8503 0.5415 1.3976 0.023 Uiso 1 1 calc R
C6 C 0.91058(11) 0.61072(9) 1.56532(9) 0.0202(2) Uani 1 1 d .
H6 H 0.8866 0.5384 1.5971 0.024 Uiso 1 1 calc R
C7 C 0.88887(11) 0.80107(9) 1.20474(8) 0.0184(2) Uani 1 1 d .
C8 C 0.86523(12) 0.76639(9) 1.07610(9) 0.0232(2) Uani 1 1 d .
H8A H 0.9462 0.8135 1.0446 0.035 Uiso 1 1 calc R
H8B H 0.7703 0.7803 1.0391 0.035 Uiso 1 1 calc R
H8C H 0.8641 0.6832 1.0626 0.035 Uiso 1 1 calc R
N2 N 0.68700(11) 0.40095(8) 0.94802(8) 0.0244(2) Uani 1 1 d .
N3 N 0.44661(10) 0.25978(8) 0.13008(8) 0.0242(2) Uani 1 1 d .
C9 C 0.78232(13) 0.38689(10) 0.87584(9) 0.0262(2) Uani 1 1 d .
H9 H 0.8824 0.3893 0.9083 0.031 Uiso 1 1 calc R
C10 C 0.74049(12) 0.36903(10) 0.75632(9) 0.0227(2) Uani 1 1 d .
H10 H 0.8106 0.3578 0.7105 0.027 Uiso 1 1 calc R
C11 C 0.59199(12) 0.36797(9) 0.70480(9) 0.0195(2) Uani 1 1 d .
C12 C 0.49333(12) 0.38350(9) 0.77980(9) 0.0224(2) Uani 1 1 d .
H12 H 0.3936 0.3847 0.7499 0.027 Uiso 1 1 calc R
C13 C 0.54409(12) 0.39716(9) 0.89875(9) 0.0237(2) Uani 1 1 d .
H13 H 0.4751 0.4041 0.9470 0.028 Uiso 1 1 calc R
C14 C 0.53652(11) 0.35166(9) 0.57891(9) 0.0208(2) Uani 1 1 d .
H14 H 0.4413 0.3655 0.5530 0.025 Uiso 1 1 calc R
C15 C 0.36968(12) 0.30530(10) 0.20211(9) 0.0249(2) Uani 1 1 d .
H15 H 0.2789 0.3232 0.1697 0.030 Uiso 1 1 calc R
C16 C 0.41635(12) 0.32728(9) 0.32119(9) 0.0231(2) Uani 1 1 d .
H16 H 0.3582 0.3594 0.3666 0.028 Uiso 1 1 calc R
C17 C 0.55191(11) 0.30075(8) 0.37272(8) 0.0184(2) Uani 1 1 d .
C18 C 0.63240(12) 0.25377(10) 0.29843(9) 0.0225(2) Uani 1 1 d .
H18 H 0.7234 0.2347 0.3282 0.027 Uiso 1 1 calc R
C19 C 0.57645(12) 0.23545(10) 0.17972(9) 0.0243(2) Uani 1 1 d .
H19 H 0.6327 0.2044 0.1319 0.029 Uiso 1 1 calc R
C20 C 0.60976(11) 0.31888(9) 0.49831(9) 0.0199(2) Uani 1 1 d .
H20 H 0.7058 0.3064 0.5238 0.024 Uiso 1 1 calc R
N4 N 0.67956(11) 1.06092(8) 0.90535(8) 0.0245(2) Uani 1 1 d .
C21 C 0.74675(12) 1.01959(10) 0.82339(9) 0.0243(2) Uani 1 1 d .
H21 H 0.8388 0.9995 0.8471 0.029 Uiso 1 1 calc R
C22 C 0.68703(12) 1.00525(10) 0.70587(9) 0.0230(2) Uani 1 1 d .
H22 H 0.7391 0.9774 0.6527 0.028 Uiso 1 1 calc R
C23 C 0.54777(12) 1.03285(9) 0.66758(9) 0.0197(2) Uani 1 1 d .
C24 C 0.47683(12) 1.07389(9) 0.75310(9) 0.0223(2) Uani 1 1 d .
H24 H 0.3832 1.0924 0.7323 0.027 Uiso 1 1 calc R
C25 C 0.54624(13) 1.08694(9) 0.86902(9) 0.0241(2) Uani 1 1 d .
H25 H 0.4974 1.1153 0.9243 0.029 Uiso 1 1 calc R
C26 C 0.47343(12) 1.01943(9) 0.54529(9) 0.0215(2) Uani 1 1 d .
H26 H 0.3805 1.0399 0.5293 0.026 Uiso 1 1 calc R
O3 O 0.88479(10) 1.09274(7) 1.11562(7) 0.0276(2) Uani 1 1 d D
H3A H 0.8122(15) 1.0862(13) 1.0558(10) 0.048(4) Uiso 1 1 d D
H3B H 0.8771(17) 1.0248(10) 1.1476(12) 0.046(4) Uiso 1 1 d D
O4 O 0.86629(9) 0.47978(6) 1.16804(7) 0.0263(2) Uani 1 1 d D
H4A H 0.8004(15) 0.4505(13) 1.1034(10) 0.052(5) Uiso 1 1 d D
H4B H 0.9083(16) 0.4211(11) 1.1906(12) 0.045(4) Uiso 1 1 d D
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'
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
C1 O1 H1O 109.5 .
C7 N1 C4 127.55(8) .
C7 N1 H1 116.2 .
C4 N1 H1 116.2 .
O1 C1 C2 123.52(9) .
O1 C1 C6 117.27(9) .
C2 C1 C6 119.21(9) .
C1 C2 C3 120.60(9) .
C1 C2 H2 119.7 .
C3 C2 H2 119.7 .
C2 C3 C4 120.17(9) .
C2 C3 H3 119.9 .
C4 C3 H3 119.9 .
C5 C4 C3 119.04(9) .
C5 C4 N1 116.92(8) .
C3 C4 N1 124.01(9) .
C6 C5 C4 120.49(9) .
C6 C5 H5 119.8 .
C4 C5 H5 119.8 .
C5 C6 C1 120.48(9) .
C5 C6 H6 119.8 .
C1 C6 H6 119.8 .
O2 C7 N1 122.97(9) .
O2 C7 C8 121.32(9) .
N1 C7 C8 115.70(9) .
C7 C8 H8A 109.5 .
C7 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
C7 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
C13 N2 C9 116.64(9) .
C19 N3 C15 116.09(9) .
N2 C9 C10 123.86(10) .
N2 C9 H9 118.1 .
C10 C9 H9 118.1 .
C9 C10 C11 119.43(10) .
C9 C10 H10 120.3 .
C11 C10 H10 120.3 .
C10 C11 C12 116.66(9) .
C10 C11 C14 123.84(9) .
C12 C11 C14 119.50(9) .
C13 C12 C11 119.89(10) .
C13 C12 H12 120.1 .
C11 C12 H12 120.1 .
N2 C13 C12 123.46(10) .
N2 C13 H13 118.3 .
C12 C13 H13 118.3 .
C20 C14 C11 126.05(9) .
C20 C14 H14 117.0 .
C11 C14 H14 117.0 .
N3 C15 C16 124.33(10) .
N3 C15 H15 117.8 .
C16 C15 H15 117.8 .
C15 C16 C17 119.28(9) .
C15 C16 H16 120.4 .
C17 C16 H16 120.4 .
C16 C17 C18 116.66(9) .
C16 C17 C20 123.42(9) .
C18 C17 C20 119.92(9) .
C19 C18 C17 119.77(9) .
C19 C18 H18 120.1 .
C17 C18 H18 120.1 .
N3 C19 C18 123.86(10) .
N3 C19 H19 118.1 .
C18 C19 H19 118.1 .
C14 C20 C17 125.55(9) .
C14 C20 H20 117.2 .
C17 C20 H20 117.2 .
C25 N4 C21 116.83(9) .
N4 C21 C22 123.79(10) .
N4 C21 H21 118.1 .
C22 C21 H21 118.1 .
C21 C22 C23 119.48(10) .
C21 C22 H22 120.3 .
C23 C22 H22 120.3 .
C22 C23 C24 116.64(9) .
C22 C23 C26 123.91(9) .
C24 C23 C26 119.44(9) .
C25 C24 C23 119.88(10) .
C25 C24 H24 120.1 .
C23 C24 H24 120.1 .
N4 C25 C24 123.36(10) .
N4 C25 H25 118.3 .
C24 C25 H25 118.3 .
C26 C26 C23 126.16(12) 2_676
C26 C26 H26 116.9 2_676
C23 C26 H26 116.9 .
H3A O3 H3B 110.6(11) .
H4A O4 H4B 106.2(11) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3670(11) .
O1 H1O 0.8200 .
O2 C7 1.2388(12) .
N1 C7 1.3459(13) .
N1 C4 1.4208(12) .
N1 H1 0.8600 .
C1 C2 1.3911(14) .
C1 C6 1.3899(14) .
C2 C3 1.3902(13) .
C2 H2 0.9300 .
C3 C4 1.3963(13) .
C3 H3 0.9300 .
C4 C5 1.3955(14) .
C5 C6 1.3871(13) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C7 C8 1.5044(13) .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
N2 C13 1.3361(15) .
N2 C9 1.3432(15) .
N3 C19 1.3351(14) .
N3 C15 1.3417(14) .
C9 C10 1.3804(14) .
C9 H9 0.9300 .
C10 C11 1.3969(14) .
C10 H10 0.9300 .
C11 C12 1.3954(14) .
C11 C14 1.4658(13) .
C12 C13 1.3832(14) .
C12 H12 0.9300 .
C13 H13 0.9300 .
C14 C20 1.3310(15) .
C14 H14 0.9300 .
C15 C16 1.3816(14) .
C15 H15 0.9300 .
C16 C17 1.3985(14) .
C16 H16 0.9300 .
C17 C18 1.3916(14) .
C17 C20 1.4661(13) .
C18 C19 1.3878(14) .
C18 H18 0.9300 .
C19 H19 0.9300 .
C20 H20 0.9300 .
N4 C25 1.3348(15) .
N4 C21 1.3439(14) .
C21 C22 1.3817(14) .
C21 H21 0.9300 .
C22 C23 1.3972(15) .
C22 H22 0.9300 .
C23 C24 1.3975(14) .
C23 C26 1.4660(14) .
C24 C25 1.3866(14) .
C24 H24 0.9300 .
C25 H25 0.9300 .
C26 C26 1.334(2) 2_676
C26 H26 0.9300 .
O3 H3A 0.872(8) .
O3 H3B 0.882(8) .
O4 H4A 0.884(8) .
O4 H4B 0.883(8) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O3 0.82 1.79 2.6030(11) 170.7 2_778
N1 H1 O4 0.86 1.97 2.8193(11) 168.0 .
O3 H3A N4 0.872(8) 1.937(9) 2.7969(12) 168.3(16) .
O3 H3B O2 0.882(8) 1.855(8) 2.7216(10) 167.0(14) .
O4 H4A N2 0.884(8) 1.929(9) 2.8022(12) 169.2(16) .
O4 H4B O1 0.883(8) 2.003(8) 2.8854(10) 177.8(14) 2_768
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_4
O1 C1 C2 C3 177.94(9) .
C6 C1 C2 C3 -1.33(15) .
C1 C2 C3 C4 0.66(16) .
C2 C3 C4 C5 0.50(15) .
C2 C3 C4 N1 -177.31(9) .
C7 N1 C4 C5 158.06(9) .
C7 N1 C4 C3 -24.09(15) .
C3 C4 C5 C6 -0.99(15) .
N1 C4 C5 C6 176.98(8) .
C4 C5 C6 C1 0.32(15) .
O1 C1 C6 C5 -178.47(9) .
C2 C1 C6 C5 0.84(15) .
C4 N1 C7 O2 1.89(16) .
C4 N1 C7 C8 -177.45(9) .
C13 N2 C9 C10 -0.08(16) .
N2 C9 C10 C11 1.62(17) .
C9 C10 C11 C12 -1.03(15) .
C9 C10 C11 C14 179.00(9) .
C10 C11 C12 C13 -0.94(15) .
C14 C11 C12 C13 179.03(9) .
C9 N2 C13 C12 -2.06(16) .
C11 C12 C13 N2 2.61(16) .
C10 C11 C14 C20 10.37(17) .
C12 C11 C14 C20 -169.60(10) .
C19 N3 C15 C16 -0.16(16) .
N3 C15 C16 C17 -0.31(17) .
C15 C16 C17 C18 0.43(15) .
C15 C16 C17 C20 -178.93(9) .
C16 C17 C18 C19 -0.12(15) .
C20 C17 C18 C19 179.27(9) .
C15 N3 C19 C18 0.50(16) .
C17 C18 C19 N3 -0.37(16) .
C11 C14 C20 C17 178.82(9) .
C16 C17 C20 C14 6.41(16) .
C18 C17 C20 C14 -172.93(10) .
C25 N4 C21 C22 1.24(16) .
N4 C21 C22 C23 -1.03(16) .
C21 C22 C23 C24 -0.10(15) .
C21 C22 C23 C26 -179.16(9) .
C22 C23 C24 C25 0.92(14) .
C26 C23 C24 C25 -179.97(9) .
C21 N4 C25 C24 -0.34(16) .
C23 C24 C25 N4 -0.73(16) .
C22 C23 C26 C26 -0.4(2) 2_676
C24 C23 C26 C26 -179.44(13) 2_676
