#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:36:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180400 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/69/7206925.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_7206925
loop_
_publ_author_name
'Bruni, Giovanna'
'Maietta, Mariarosa'
'Berbenni, Vittorio'
'Bini, Marcella'
'Ferrari, Stefania'
'Capsoni, Doretta'
'Boiocchi, Massimo'
'Milanese, Chiara'
'Marini, Amedeo'
_publ_section_title
;
 Preparation and characterization of carprofen co-crystals
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              435
_journal_paper_doi               10.1039/c1ce05571b
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         'C15 H12 Cl N O2, 1.5(C10 H8 N2)'
_chemical_formula_sum            'C30 H24 Cl N4 O2'
_chemical_formula_weight         507.98
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 110.33(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.030(8)
_cell_length_b                   5.5550(15)
_cell_length_c                   25.191(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      7
_cell_measurement_theta_min      4
_cell_volume                     2497.1(16)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'PROFIT (Streltsov & Zavodnik, 1989)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       'omega 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  0.0804
_diffrn_reflns_av_sigmaI/netI    0.1307
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2436
_diffrn_reflns_theta_full        20.05
_diffrn_reflns_theta_max         20.05
_diffrn_reflns_theta_min         1.14
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  300
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.9997
_exptl_absorpt_correction_T_min  0.9778
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
;
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'PLATY PRISM'
_exptl_crystal_F_000             1060
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     335
_refine_ls_number_reflns         2341
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.2039
_refine_ls_R_factor_gt           0.1322
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0928P)²+18.1751P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2950
_refine_ls_wR_factor_ref         0.3415
_reflns_number_gt                1254
_reflns_number_total             2341
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c1ce05571b.txt
_cod_data_source_block           1:1.5
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7206925
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'
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 -0.0598(2) 0.2896(8) 0.15011(19) 0.0970(16) Uani 1 1 d .
C1 C 0.3066(10) 0.424(3) 0.1142(7) 0.087(5) Uani 1 1 d .
H1 H 0.3291 0.3108 0.0981 0.104 Uiso 1 1 calc R
C2 C 0.2347(10) 0.378(3) 0.1159(6) 0.076(5) Uani 1 1 d .
H2 H 0.2072 0.2441 0.0981 0.091 Uiso 1 1 calc R
C3 C 0.2067(9) 0.541(3) 0.1449(6) 0.069(4) Uani 1 1 d .
C4 C 0.1368(9) 0.555(3) 0.1567(6) 0.067(4) Uani 1 1 d .
C5 C 0.0767(9) 0.405(3) 0.1470(6) 0.067(4) Uani 1 1 d .
H5 H 0.0738 0.2609 0.1274 0.081 Uiso 1 1 calc R
C6 C 0.0212(8) 0.471(3) 0.1666(6) 0.076(5) Uani 1 1 d .
C7 C 0.0239(8) 0.672(3) 0.1976(7) 0.079(5) Uani 1 1 d .
H7 H -0.0151 0.7061 0.2106 0.095 Uiso 1 1 calc R
C8 C 0.0850(10) 0.826(3) 0.2103(6) 0.088(5) Uani 1 1 d .
H8 H 0.0881 0.9635 0.2322 0.105 Uiso 1 1 calc R
C9 C 0.1422(9) 0.767(3) 0.1886(6) 0.064(4) Uani 1 1 d .
C10 C 0.2464(9) 0.745(3) 0.1677(7) 0.078(5) Uani 1 1 d .
C11 C 0.3162(9) 0.793(3) 0.1632(6) 0.070(4) Uani 1 1 d .
H11 H 0.3430 0.9316 0.1786 0.084 Uiso 1 1 calc R
C12 C 0.3434(9) 0.627(3) 0.1351(7) 0.072(4) Uani 1 1 d .
C13 C 0.4236(9) 0.673(3) 0.1328(7) 0.093(6) Uani 1 1 d .
H13 H 0.4291 0.5389 0.1093 0.112 Uiso 1 1 calc R
C14 C 0.4823(9) 0.631(3) 0.1839(7) 0.110(6) Uani 1 1 d .
H14A H 0.5286 0.6180 0.1768 0.165 Uiso 1 1 calc R
H14B H 0.4731 0.4844 0.2005 0.165 Uiso 1 1 calc R
H14C H 0.4855 0.7626 0.2094 0.165 Uiso 1 1 calc R
C15 C 0.4260(10) 0.883(4) 0.0979(9) 0.091(6) Uani 1 1 d .
N1 N 0.2082(6) 0.885(2) 0.1950(5) 0.069(3) Uani 1 1 d .
H1N H 0.2232 1.0182 0.2125 0.083 Uiso 1 1 calc R
O1 O 0.4654(8) 1.060(3) 0.1182(8) 0.158(7) Uani 1 1 d .
O2 O 0.3848(8) 0.892(2) 0.0478(6) 0.131(5) Uani 1 1 d .
H2O H 0.3836 1.0309 0.0363 0.158 Uiso 1 1 calc R
C16 C 0.3128(13) 1.394(4) -0.0316(9) 0.124(8) Uani 1 1 d .
H16 H 0.2802 1.3447 -0.0134 0.149 Uiso 1 1 calc R
C17 C 0.2902(9) 1.576(4) -0.0692(8) 0.104(6) Uani 1 1 d .
H17 H 0.2440 1.6480 -0.0753 0.125 Uiso 1 1 calc R
C18 C 0.3331(8) 1.653(2) -0.0976(6) 0.064(4) Uani 1 1 d .
C19 C 0.4005(9) 1.542(4) -0.0840(8) 0.114(7) Uani 1 1 d .
H19 H 0.4338 1.5868 -0.1019 0.137 Uiso 1 1 calc R
C20 C 0.4187(13) 1.372(4) -0.0459(10) 0.139(9) Uani 1 1 d .
H20 H 0.4667 1.3081 -0.0370 0.166 Uiso 1 1 calc R
C21 C 0.2277(10) 2.167(4) -0.1865(8) 0.105(6) Uani 1 1 d U
H21 H 0.1868 2.2604 -0.1874 0.126 Uiso 1 1 calc R
C22 C 0.2470(11) 1.988(3) -0.1461(8) 0.115(7) Uani 1 1 d .
H22 H 0.2201 1.9635 -0.1220 0.138 Uiso 1 1 calc R
C23 C 0.3075(9) 1.850(3) -0.1431(7) 0.073(4) Uani 1 1 d .
C24 C 0.3470(8) 1.913(3) -0.1779(8) 0.090(5) Uani 1 1 d .
H24 H 0.3920 1.8383 -0.1744 0.108 Uiso 1 1 calc R
C25 C 0.3183(10) 2.086(3) -0.2169(7) 0.086(5) Uani 1 1 d .
H25 H 0.3434 2.1127 -0.2422 0.104 Uiso 1 1 calc R
N2 N 0.3775(11) 1.279(3) -0.0185(6) 0.099(5) Uani 1 1 d .
N3 N 0.2583(8) 2.224(3) -0.2238(5) 0.087(4) Uani 1 1 d .
C26 C 0.1181(12) 0.187(4) -0.0484(8) 0.118(7) Uani 1 1 d .
H26 H 0.1254 0.3059 -0.0719 0.141 Uiso 1 1 calc R
C27 C 0.0498(10) 0.178(3) -0.0379(8) 0.098(6) Uani 1 1 d .
H27 H 0.0141 0.2963 -0.0534 0.118 Uiso 1 1 calc R
C28 C 0.0351(7) 0.009(3) -0.0071(6) 0.061(4) Uani 1 1 d .
C29 C 0.0938(9) -0.150(3) 0.0192(7) 0.080(5) Uani 1 1 d .
H29 H 0.0890 -0.2641 0.0447 0.096 Uiso 1 1 calc R
C30 C 0.1588(8) -0.136(3) 0.0071(7) 0.075(5) Uani 1 1 d .
H30 H 0.1959 -0.2501 0.0228 0.090 Uiso 1 1 calc R
N4 N 0.1708(8) 0.030(3) -0.0256(6) 0.091(4) Uani 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'
Cl Cl 0.1484 0.1585 '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_3
C12 C1 C2 121.6(14) .
C12 C1 H1 119.2 .
C2 C1 H1 119.2 .
C3 C2 C1 117.0(15) .
C3 C2 H2 121.5 .
C1 C2 H2 121.5 .
C10 C3 C2 120.3(15) .
C10 C3 C4 106.2(14) .
C2 C3 C4 133.5(16) .
C5 C4 C9 120.1(15) .
C5 C4 C3 134.0(16) .
C9 C4 C3 105.6(14) .
C6 C5 C4 118.5(14) .
C6 C5 H5 120.7 .
C4 C5 H5 120.8 .
C7 C6 C5 123.5(14) .
C7 C6 Cl1 117.5(13) .
C5 C6 Cl1 119.0(14) .
C6 C7 C8 120.3(14) .
C6 C7 H7 119.9 .
C8 C7 H7 119.9 .
C7 C8 C9 117.5(15) .
C7 C8 H8 121.3 .
C9 C8 H8 121.3 .
N1 C9 C4 110.2(13) .
N1 C9 C8 129.7(15) .
C4 C9 C8 120.0(15) .
C3 C10 N1 111.0(13) .
C3 C10 C11 121.6(15) .
N1 C10 C11 127.3(16) .
C12 C11 C10 117.0(15) .
C12 C11 H11 121.5 .
C10 C11 H11 121.5 .
C1 C12 C11 122.2(15) .
C1 C12 C13 120.4(15) .
C11 C12 C13 117.2(15) .
C14 C13 C15 120.1(17) .
C14 C13 C12 114.6(14) .
C15 C13 C12 112.6(13) .
C14 C13 H13 102.0 .
C15 C13 H13 102.1 .
C12 C13 H13 102.0 .
C13 C14 H14A 109.5 .
C13 C14 H14B 109.5 .
H14A C14 H14B 109.5 .
C13 C14 H14C 109.5 .
H14A C14 H14C 109.5 .
H14B C14 H14C 109.5 .
O2 C15 O1 117.7(19) .
O2 C15 C13 120(2) .
O1 C15 C13 121.7(19) .
C9 N1 C10 106.9(12) .
C9 N1 H1N 126.6 .
C10 N1 H1N 126.6 .
C15 O2 H2O 109.5 .
N2 C16 C17 125.1(17) .
N2 C16 H16 117.5 .
C17 C16 H16 117.4 .
C18 C17 C16 121.0(17) .
C18 C17 H17 119.5 .
C16 C17 H17 119.5 .
C17 C18 C19 114.9(16) .
C17 C18 C23 122.4(15) .
C19 C18 C23 122.7(15) .
C20 C19 C18 120.1(17) .
C20 C19 H19 119.9 .
C18 C19 H19 120.0 .
C19 C20 N2 127.8(19) .
C19 C20 H20 116.1 .
N2 C20 H20 116.1 .
N3 C21 C22 129.6(17) .
N3 C21 H21 115.2 .
C22 C21 H21 115.2 .
C23 C22 C21 116.7(15) .
C23 C22 H22 121.6 .
C21 C22 H22 121.7 .
C22 C23 C24 117.1(15) .
C22 C23 C18 119.1(14) .
C24 C23 C18 123.4(15) .
C25 C24 C23 118.2(15) .
C25 C24 H24 120.9 .
C23 C24 H24 120.9 .
N3 C25 C24 127.8(16) .
N3 C25 H25 116.1 .
C24 C25 H25 116.1 .
C20 N2 C16 110.9(15) .
C21 N3 C25 110.1(15) .
N4 C26 C27 120.7(16) .
N4 C26 H26 119.7 .
C27 C26 H26 119.6 .
C28 C27 C26 122.5(15) .
C28 C27 H27 118.7 .
C26 C27 H27 118.8 .
C27 C28 C29 115.6(13) .
C27 C28 C28 125.5(18) 3
C29 C28 C28 118.4(17) 3
C30 C29 C28 119.4(14) .
C30 C29 H29 120.3 .
C28 C29 H29 120.3 .
N4 C30 C29 123.2(14) .
N4 C30 H30 118.4 .
C29 C30 H30 118.4 .
C26 N4 C30 118.1(14) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C6 1.766(14) .
C1 C12 1.34(2) .
C1 C2 1.408(19) .
C1 H1 0.9300 .
C2 C3 1.380(18) .
C2 H2 0.9300 .
C3 C10 1.37(2) .
C3 C4 1.46(2) .
C4 C5 1.367(18) .
C4 C9 1.412(19) .
C5 C6 1.364(18) .
C5 H5 0.9300 .
C6 C7 1.35(2) .
C7 C8 1.39(2) .
C7 H7 0.9300 .
C8 C9 1.416(19) .
C8 H8 0.9300 .
C9 N1 1.374(16) .
C10 N1 1.397(17) .
C10 C11 1.397(18) .
C11 C12 1.367(18) .
C11 H11 0.9300 .
C12 C13 1.57(2) .
C13 C14 1.401(19) .
C13 C15 1.47(2) .
C13 H13 0.9800 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 O2 1.234(19) .
C15 O1 1.24(2) .
N1 H1N 0.8600 .
O2 H2O 0.8200 .
C16 N2 1.32(2) .
C16 C17 1.35(2) .
C16 H16 0.9300 .
C17 C18 1.330(18) .
C17 H17 0.9300 .
C18 C19 1.355(18) .
C18 C23 1.537(19) .
C19 C20 1.31(2) .
C19 H19 0.9300 .
C20 N2 1.32(2) .
C20 H20 0.9300 .
C21 N3 1.304(19) .
C21 C22 1.38(2) .
C21 H21 0.9300 .
C22 C23 1.36(2) .
C22 H22 0.9300 .
C23 C24 1.383(19) .
C24 C25 1.35(2) .
C24 H24 0.9300 .
C25 N3 1.336(18) .
C25 H25 0.9300 .
C26 N4 1.30(2) .
C26 C27 1.41(2) .
C26 H26 0.9300 .
C27 C28 1.307(18) .
C27 H27 0.9300 .
C28 C29 1.398(18) .
C28 C28 1.50(3) 3
C29 C30 1.374(17) .
C29 H29 0.9300 .
C30 N4 1.308(17) .
C30 H30 0.9300 .
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_4
C12 C1 C2 C3 -6(2) . .
C1 C2 C3 C10 4(2) . .
C1 C2 C3 C4 -179.2(14) . .
C10 C3 C4 C5 -177.1(16) . .
C2 C3 C4 C5 6(3) . .
C10 C3 C4 C9 -2.6(15) . .
C2 C3 C4 C9 -179.7(15) . .
C9 C4 C5 C6 3(2) . .
C3 C4 C5 C6 176.7(15) . .
C4 C5 C6 C7 -3(2) . .
C4 C5 C6 Cl1 175.6(11) . .
C5 C6 C7 C8 1(2) . .
Cl1 C6 C7 C8 -177.7(12) . .
C6 C7 C8 C9 1(2) . .
C5 C4 C9 N1 177.5(12) . .
C3 C4 C9 N1 2.1(15) . .
C5 C4 C9 C8 0(2) . .
C3 C4 C9 C8 -175.8(13) . .
C7 C8 C9 N1 -179.0(14) . .
C7 C8 C9 C4 -2(2) . .
C2 C3 C10 N1 179.8(13) . .
C4 C3 C10 N1 2.3(17) . .
C2 C3 C10 C11 -1(2) . .
C4 C3 C10 C11 -178.8(13) . .
C3 C10 C11 C12 0(2) . .
N1 C10 C11 C12 178.8(14) . .
C2 C1 C12 C11 5(3) . .
C2 C1 C12 C13 179.8(13) . .
C10 C11 C12 C1 -2(2) . .
C10 C11 C12 C13 -176.7(13) . .
C1 C12 C13 C14 -101(2) . .
C11 C12 C13 C14 73.6(19) . .
C1 C12 C13 C15 116.8(19) . .
C11 C12 C13 C15 -68(2) . .
C14 C13 C15 O2 163.1(17) . .
C12 C13 C15 O2 -57(2) . .
C14 C13 C15 O1 -21(3) . .
C12 C13 C15 O1 118(2) . .
C4 C9 N1 C10 -0.7(15) . .
C8 C9 N1 C10 176.9(15) . .
C3 C10 N1 C9 -1.0(17) . .
C11 C10 N1 C9 -179.9(14) . .
N2 C16 C17 C18 1(3) . .
C16 C17 C18 C19 -2(3) . .
C16 C17 C18 C23 176.6(16) . .
C17 C18 C19 C20 0(3) . .
C23 C18 C19 C20 -178.5(18) . .
C18 C19 C20 N2 3(4) . .
N3 C21 C22 C23 1(3) . .
C21 C22 C23 C24 5(3) . .
C21 C22 C23 C18 178.2(15) . .
C17 C18 C23 C22 15(2) . .
C19 C18 C23 C22 -166.1(18) . .
C17 C18 C23 C24 -171.9(17) . .
C19 C18 C23 C24 7(2) . .
C22 C23 C24 C25 -8(2) . .
C18 C23 C24 C25 178.8(14) . .
C23 C24 C25 N3 6(3) . .
C19 C20 N2 C16 -4(3) . .
C17 C16 N2 C20 2(3) . .
C22 C21 N3 C25 -3(3) . .
C24 C25 N3 C21 -1(2) . .
N4 C26 C27 C28 -3(3) . .
C26 C27 C28 C29 6(3) . .
C26 C27 C28 C28 178.3(18) . 3
C27 C28 C29 C30 -7(2) . .
C28 C28 C29 C30 -179.6(16) 3 .
C28 C29 C30 N4 4(2) . .
C27 C26 N4 C30 0(3) . .
C29 C30 N4 C26 -1(3) . .
