#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:38:21 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180442 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/11/7211136.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_7211136
loop_
_publ_author_name
'Perumalla, Sathyanarayana Reddy'
'Sun, Changquan Calvin'
_publ_section_title
;
 Synthon preference in O-protonated amide crystals -- dominance of short
 strong hydrogen bonds
;
_journal_issue                   44
_journal_name_full               CrystEngComm
_journal_page_first              8941
_journal_paper_doi               10.1039/c3ce41271g
_journal_volume                  15
_journal_year                    2013
_chemical_formula_sum            'C20 H33 Cl2 N2 O7'
_chemical_formula_weight         484.38
_chemical_name_common            'Phenacetin hydrochloride salt trihydrate'
_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                76.1270(10)
_cell_angle_beta                 77.3120(10)
_cell_angle_gamma                87.9620(10)
_cell_formula_units_Z            2
_cell_length_a                   6.7923(4)
_cell_length_b                   13.4759(8)
_cell_length_c                   14.1913(8)
_cell_measurement_reflns_used    6761
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.60
_cell_measurement_theta_min      3.03
_cell_volume                     1230.08(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker Apex2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker Apex II platform CCD'
_diffrn_measurement_method       'Omega and Phi scans'
_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  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14262
_diffrn_reflns_theta_full        27.63
_diffrn_reflns_theta_max         27.63
_diffrn_reflns_theta_min         1.51
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.9557
_exptl_absorpt_correction_T_min  0.9360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (G. Sheldrick, 2003)'
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             514
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.769
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.315
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5614
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.315
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0508
_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+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1715
_refine_ls_wR_factor_ref         0.1835
_reflns_number_gt                4454
_reflns_number_total             5614
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ce41271g.txt
_cod_data_source_block           11083_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-Scan'
changed to 'multi-scan' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7211136
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
Cl1 Cl 0.21234(8) 0.94548(4) 0.08278(4) 0.03099(18) Uani 1 1 d .
Cl2 Cl -0.67938(8) 1.05007(4) 0.39982(4) 0.03368(19) Uani 1 1 d .
O29 O -0.1520(3) 1.02750(12) 0.19296(14) 0.0377(4) Uani 1 1 d .
O28 O -0.4725(2) 1.33840(10) 0.06939(10) 0.0218(3) Uani 1 1 d .
O27 O -1.1440(2) 1.44949(10) -0.19818(11) 0.0296(4) Uani 1 1 d .
O26 O -1.0232(2) 0.65880(10) 0.42973(10) 0.0218(3) Uani 1 1 d .
O25 O -0.4934(3) 0.95297(14) 0.22010(16) 0.0423(4) Uani 1 1 d .
O24 O -0.1034(3) 1.01743(17) 0.36538(16) 0.0495(5) Uani 1 1 d .
O23 O -0.3377(2) 0.55242(10) 0.69097(11) 0.0298(4) Uani 1 1 d .
N22 N -0.4108(2) 0.71346(11) 0.61908(11) 0.0168(3) Uani 1 1 d .
H22A H -0.3788 0.7782 0.6103 0.020 Uiso 1 1 calc R
C21 C -0.8736(3) 0.67638(14) 0.47530(13) 0.0177(4) Uani 1 1 d .
N20 N -1.0896(2) 1.28843(11) -0.11883(11) 0.0167(3) Uani 1 1 d .
H20A H -1.1288 1.2242 -0.1070 0.020 Uiso 1 1 calc R
C19 C -0.6507(3) 0.78122(14) 0.52172(13) 0.0187(4) Uani 1 1 d .
H19A H -0.6025 0.8470 0.5202 0.022 Uiso 1 1 calc R
C18 C -0.9297(3) 1.30496(14) -0.07360(13) 0.0164(4) Uani 1 1 d .
C17 C -0.6225(3) 1.32159(14) 0.02359(13) 0.0177(4) Uani 1 1 d .
C16 C -0.6871(3) 1.22519(14) 0.02157(14) 0.0195(4) Uani 1 1 d .
H16A H -0.6272 1.1652 0.0532 0.023 Uiso 1 1 calc R
C15 C -0.6381(3) 0.59809(14) 0.57542(14) 0.0202(4) Uani 1 1 d .
H15A H -0.5827 0.5386 0.6106 0.024 Uiso 1 1 calc R
C14 C -0.5676(3) 0.69531(14) 0.57285(13) 0.0166(4) Uani 1 1 d .
C13 C -0.8031(3) 0.77313(14) 0.47261(14) 0.0196(4) Uani 1 1 d .
H13A H -0.8585 0.8327 0.4377 0.024 Uiso 1 1 calc R
C12 C -0.8400(3) 1.21814(14) -0.02733(13) 0.0189(4) Uani 1 1 d .
H12A H -0.8843 1.1527 -0.0292 0.023 Uiso 1 1 calc R
C11 C -0.8643(3) 1.40172(14) -0.07177(14) 0.0204(4) Uani 1 1 d .
H11A H -0.9237 1.4616 -0.1038 0.024 Uiso 1 1 calc R
C10 C -1.2696(3) 0.70622(16) 0.33237(15) 0.0243(4) Uani 1 1 d .
H10A H -1.3333 0.7638 0.2942 0.036 Uiso 1 1 calc R
H10B H -1.3722 0.6666 0.3868 0.036 Uiso 1 1 calc R
H10C H -1.2059 0.6624 0.2887 0.036 Uiso 1 1 calc R
C9 C -0.3066(3) 0.64830(14) 0.67283(14) 0.0188(4) Uani 1 1 d .
C8 C -1.1871(3) 1.35414(14) -0.17526(14) 0.0184(4) Uani 1 1 d .
C7 C -0.7118(3) 1.40912(14) -0.02270(14) 0.0196(4) Uani 1 1 d .
H7A H -0.6678 1.4745 -0.0206 0.024 Uiso 1 1 calc R
C6 C -1.1111(3) 0.74632(15) 0.37469(14) 0.0205(4) Uani 1 1 d .
H6A H -1.0063 0.7866 0.3204 0.025 Uiso 1 1 calc R
H6B H -1.1734 0.7909 0.4190 0.025 Uiso 1 1 calc R
C5 C -1.3490(3) 1.31543(15) -0.21444(14) 0.0208(4) Uani 1 1 d .
H5A H -1.4073 1.3730 -0.2554 0.031 Uiso 1 1 calc R
H5B H -1.4547 1.2804 -0.1587 0.031 Uiso 1 1 calc R
H5C H -1.2910 1.2676 -0.2549 0.031 Uiso 1 1 calc R
C4 C -0.7897(3) 0.58937(14) 0.52614(14) 0.0199(4) Uani 1 1 d .
H4A H -0.8368 0.5235 0.5270 0.024 Uiso 1 1 calc R
C3 C -0.3862(3) 1.25030(15) 0.12512(14) 0.0201(4) Uani 1 1 d .
H3A H -0.3214 1.2062 0.0809 0.024 Uiso 1 1 calc R
H3B H -0.4922 1.2097 0.1784 0.024 Uiso 1 1 calc R
C2 C -0.2313(3) 1.29066(16) 0.16930(15) 0.0243(4) Uani 1 1 d .
H2A H -0.1682 1.2332 0.2080 0.036 Uiso 1 1 calc R
H2B H -0.2976 1.3341 0.2128 0.036 Uiso 1 1 calc R
H2C H -0.1277 1.3308 0.1157 0.036 Uiso 1 1 calc R
C1 C -0.1503(3) 0.68923(15) 0.71408(14) 0.0209(4) Uani 1 1 d .
H1A H -0.0858 0.6322 0.7526 0.031 Uiso 1 1 calc R
H1B H -0.2147 0.7334 0.7573 0.031 Uiso 1 1 calc R
H1C H -0.0483 0.7289 0.6593 0.031 Uiso 1 1 calc R
H29C H -0.050(5) 0.994(2) 0.162(2) 0.064(9) Uiso 1 1 d .
H25B H -0.571(6) 0.991(3) 0.271(3) 0.099(12) Uiso 1 1 d .
H24B H -0.179(5) 1.005(3) 0.415(3) 0.079(13) Uiso 1 1 d .
H24A H 0.010(5) 1.027(2) 0.370(2) 0.049(9) Uiso 1 1 d .
H29B H -0.296(5) 1.003(2) 0.199(2) 0.058(8) Uiso 1 1 d .
H25A H -0.542(5) 0.962(2) 0.171(3) 0.063(10) Uiso 1 1 d .
H29A H -0.152(5) 1.015(2) 0.263(2) 0.069(10) Uiso 1 1 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'
Cl Cl 0.1484 0.1585 '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
C17 O28 C3 117.72(14)
C21 O26 C6 117.58(14)
C9 N22 C14 129.90(16)
O26 C21 C13 124.41(17)
O26 C21 C4 115.70(16)
C13 C21 C4 119.89(16)
C8 N20 C18 129.91(16)
C14 C19 C13 121.33(17)
C12 C18 C11 119.69(17)
C12 C18 N20 116.37(15)
C11 C18 N20 123.92(16)
O28 C17 C7 115.52(15)
O28 C17 C16 124.41(17)
C7 C17 C16 120.07(16)
C12 C16 C17 119.02(17)
C4 C15 C14 119.44(18)
C19 C14 C15 119.57(17)
C19 C14 N22 116.08(16)
C15 C14 N22 124.34(16)
C19 C13 C21 119.13(17)
C16 C12 C18 121.23(17)
C7 C11 C18 119.27(18)
O23 C9 N22 121.36(16)
O23 C9 C1 120.08(16)
N22 C9 C1 118.56(16)
O27 C8 N20 121.11(16)
O27 C8 C5 120.02(16)
N20 C8 C5 118.86(16)
C11 C7 C17 120.71(17)
O26 C6 C10 106.95(15)
C15 C4 C21 120.64(17)
O28 C3 C2 106.56(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O28 C17 1.374(2)
O28 C3 1.443(2)
O27 C8 1.276(2)
O26 C21 1.373(2)
O26 C6 1.439(2)
O23 C9 1.271(2)
N22 C9 1.314(2)
N22 C14 1.424(2)
C21 C13 1.394(3)
C21 C4 1.396(3)
N20 C8 1.310(2)
N20 C18 1.426(2)
C19 C14 1.384(3)
C19 C13 1.389(2)
C18 C12 1.388(3)
C18 C11 1.400(2)
C17 C7 1.394(3)
C17 C16 1.394(3)
C16 C12 1.388(2)
C15 C4 1.388(3)
C15 C14 1.400(2)
C11 C7 1.388(3)
C10 C6 1.514(2)
C9 C1 1.497(2)
C8 C5 1.496(2)
C3 C2 1.514(2)
