#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:36:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180400 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/69/7206927.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_7206927
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                 110.116(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.0685(15)
_cell_length_b                   5.5501(5)
_cell_length_c                   25.148(2)
_cell_measurement_reflns_used    3266
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21
_cell_measurement_theta_min      2
_cell_volume                     2499.1(4)
_computing_cell_refinement       'SAINT (Bruker-Axs Inc)'
_computing_data_collection       'SMART (Bruker-Axs Inc)'
_computing_data_reduction        'SAINT (Bruker-Axs Inc)'
_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_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker-Axs Smart-Apex 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  0.0431
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            21045
_diffrn_reflns_theta_full        25.04
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_min         1.14
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'PLATY PRISM'
_exptl_crystal_F_000             1060
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4438
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0591
_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)+(0.0909P)²+0.8941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1552
_refine_ls_wR_factor_ref         0.1895
_reflns_number_gt                2716
_reflns_number_total             4438
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c1ce05571b.txt
_cod_data_source_block           bin4_2
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7206927
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 -0.05983(5) 0.29026(19) 0.15067(4) 0.0870(4) Uani 1 1 d .
C1 C 0.3026(2) 0.4228(6) 0.10941(15) 0.0689(9) Uani 1 1 d .
H1 H 0.3220 0.3123 0.0904 0.083 Uiso 1 1 calc R
C2 C 0.2344(2) 0.3797(6) 0.11397(14) 0.0644(9) Uani 1 1 d .
H2 H 0.2078 0.2420 0.0979 0.077 Uiso 1 1 calc R
C3 C 0.20483(17) 0.5439(5) 0.14296(13) 0.0553(8) Uani 1 1 d .
C4 C 0.13786(17) 0.5516(5) 0.15666(12) 0.0531(7) Uani 1 1 d .
C5 C 0.07559(18) 0.4024(5) 0.14540(13) 0.0593(8) Uani 1 1 d .
H5 H 0.0716 0.2618 0.1244 0.071 Uiso 1 1 calc R
C6 C 0.02037(19) 0.4680(6) 0.16600(14) 0.0640(9) Uani 1 1 d .
C7 C 0.0250(2) 0.6775(7) 0.19751(15) 0.0716(10) Uani 1 1 d .
H7 H -0.0135 0.7171 0.2107 0.086 Uiso 1 1 calc R
C8 C 0.0857(2) 0.8252(6) 0.20922(14) 0.0673(9) Uani 1 1 d .
H8 H 0.0894 0.9640 0.2307 0.081 Uiso 1 1 calc R
C9 C 0.14188(19) 0.7642(5) 0.18842(13) 0.0582(8) Uani 1 1 d .
C10 C 0.24643(19) 0.7495(5) 0.16616(13) 0.0585(8) Uani 1 1 d .
C11 C 0.31596(19) 0.7939(6) 0.16120(15) 0.0660(9) Uani 1 1 d .
H11 H 0.3429 0.9318 0.1768 0.079 Uiso 1 1 calc R
C12 C 0.34379(19) 0.6273(6) 0.13247(14) 0.0653(9) Uani 1 1 d .
C13 C 0.4206(2) 0.6603(7) 0.12783(16) 0.0750(10) Uani 1 1 d .
H13 H 0.4273 0.5280 0.1042 0.090 Uiso 1 1 calc R
C14 C 0.4824(2) 0.6366(9) 0.18443(18) 0.1010(13) Uani 1 1 d .
H14A H 0.5299 0.6489 0.1793 0.152 Uiso 1 1 calc R
H14B H 0.4787 0.4830 0.2008 0.152 Uiso 1 1 calc R
H14C H 0.4779 0.7628 0.2092 0.152 Uiso 1 1 calc R
C15 C 0.4257(2) 0.8913(6) 0.09744(17) 0.0656(9) Uani 1 1 d .
N1 N 0.20715(16) 0.8834(5) 0.19345(12) 0.0656(7) Uani 1 1 d D
H1N H 0.2262(17) 1.019(4) 0.2178(11) 0.079 Uiso 1 1 d D
O1 O 0.46281(17) 1.0621(5) 0.11941(15) 0.1153(11) Uani 1 1 d .
O2 O 0.3841(2) 0.8917(5) 0.04515(14) 0.1125(11) Uani 1 1 d D
H2O H 0.393(2) 1.034(5) 0.0265(18) 0.135 Uiso 1 1 d D
C16 C 0.3108(3) 1.3929(9) -0.03298(19) 0.0985(13) Uani 1 1 d .
H16 H 0.2784 1.3400 -0.0150 0.118 Uiso 1 1 calc R
C17 C 0.2874(2) 1.5814(8) -0.07135(18) 0.0942(13) Uani 1 1 d .
H17 H 0.2410 1.6526 -0.0779 0.113 Uiso 1 1 calc R
C18 C 0.33247(19) 1.6614(6) -0.09934(14) 0.0610(8) Uani 1 1 d .
C19 C 0.4006(3) 1.5547(8) -0.08515(19) 0.1013(14) Uani 1 1 d .
H19 H 0.4347 1.6075 -0.1016 0.122 Uiso 1 1 calc R
C20 C 0.4195(3) 1.3693(9) -0.0466(2) 0.1131(16) Uani 1 1 d .
H20 H 0.4663 1.2990 -0.0385 0.136 Uiso 1 1 calc R
C21 C 0.2247(3) 2.1716(8) -0.1892(2) 0.0998(14) Uani 1 1 d .
H21 H 0.1825 2.2622 -0.1919 0.120 Uiso 1 1 calc R
C22 C 0.2459(2) 1.9943(8) -0.14839(19) 0.0937(13) Uani 1 1 d .
H22 H 0.2182 1.9682 -0.1249 0.112 Uiso 1 1 calc R
C23 C 0.30792(18) 1.8561(6) -0.14233(13) 0.0597(8) Uani 1 1 d .
C24 C 0.3452(2) 1.9086(7) -0.17867(16) 0.0776(10) Uani 1 1 d .
H24 H 0.3879 1.8229 -0.1766 0.093 Uiso 1 1 calc R
C25 C 0.3192(2) 2.0894(7) -0.21853(16) 0.0795(10) Uani 1 1 d .
H25 H 0.3454 2.1197 -0.2429 0.095 Uiso 1 1 calc R
N2 N 0.3756(2) 1.2848(5) -0.02045(14) 0.0834(9) Uani 1 1 d .
N3 N 0.25987(19) 2.2206(5) -0.22413(13) 0.0761(8) Uani 1 1 d .
C26 C 0.1167(3) 0.1861(8) -0.0480(2) 0.0998(14) Uani 1 1 d .
H26 H 0.1237 0.3065 -0.0714 0.120 Uiso 1 1 calc R
C27 C 0.0498(2) 0.1833(7) -0.03885(19) 0.0918(13) Uani 1 1 d .
H27 H 0.0140 0.3004 -0.0553 0.110 Uiso 1 1 calc R
C28 C 0.03571(18) 0.0067(5) -0.00525(13) 0.0600(8) Uani 1 1 d .
C29 C 0.0938(2) -0.1534(6) 0.01761(16) 0.0773(10) Uani 1 1 d .
H29 H 0.0885 -0.2772 0.0409 0.093 Uiso 1 1 calc R
C30 C 0.1591(2) -0.1327(7) 0.00656(17) 0.0825(11) Uani 1 1 d .
H30 H 0.1969 -0.2431 0.0235 0.099 Uiso 1 1 calc R
N4 N 0.17190(18) 0.0320(6) -0.02627(14) 0.0826(9) 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
C2 C1 C12 121.8(3) .
C2 C1 H1 119.1 .
C12 C1 H1 119.1 .
C1 C2 C3 119.7(3) .
C1 C2 H2 120.2 .
C3 C2 H2 120.2 .
C10 C3 C2 118.4(3) .
C10 C3 C4 107.5(3) .
C2 C3 C4 134.1(3) .
C5 C4 C9 119.2(3) .
C5 C4 C3 134.5(3) .
C9 C4 C3 106.4(3) .
C6 C5 C4 118.4(3) .
C6 C5 H5 120.8 .
C4 C5 H5 120.8 .
C5 C6 C7 121.9(3) .
C5 C6 Cl1 119.6(3) .
C7 C6 Cl1 118.4(3) .
C8 C7 C6 120.5(3) .
C8 C7 H7 119.8 .
C6 C7 H7 119.8 .
C7 C8 C9 118.7(3) .
C7 C8 H8 120.7 .
C9 C8 H8 120.7 .
N1 C9 C8 129.8(3) .
N1 C9 C4 109.0(3) .
C8 C9 C4 121.3(3) .
N1 C10 C11 129.7(3) .
N1 C10 C3 108.5(3) .
C11 C10 C3 121.8(3) .
C12 C11 C10 118.3(3) .
C12 C11 H11 120.8 .
C10 C11 H11 120.8 .
C11 C12 C1 120.0(3) .
C11 C12 C13 120.8(3) .
C1 C12 C13 119.2(3) .
C14 C13 C15 112.7(3) .
C14 C13 C12 112.2(3) .
C15 C13 C12 111.8(3) .
C14 C13 H13 106.6 .
C15 C13 H13 106.6 .
C12 C13 H13 106.6 .
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 .
O1 C15 O2 122.1(3) .
O1 C15 C13 124.6(4) .
O2 C15 C13 113.3(3) .
C9 N1 C10 108.7(3) .
C9 N1 H1N 125(2) .
C10 N1 H1N 126(2) .
C15 O2 H2O 110(3) .
N2 C16 C17 124.3(4) .
N2 C16 H16 117.8 .
C17 C16 H16 117.8 .
C18 C17 C16 119.7(4) .
C18 C17 H17 120.1 .
C16 C17 H17 120.1 .
C17 C18 C19 116.1(3) .
C17 C18 C23 121.2(3) .
C19 C18 C23 122.8(3) .
C18 C19 C20 120.4(4) .
C18 C19 H19 119.8 .
C20 C19 H19 119.8 .
N2 C20 C19 124.2(4) .
N2 C20 H20 117.9 .
C19 C20 H20 117.9 .
N3 C21 C22 124.2(4) .
N3 C21 H21 117.9 .
C22 C21 H21 117.9 .
C23 C22 C21 120.2(4) .
C23 C22 H22 119.9 .
C21 C22 H22 119.9 .
C24 C23 C22 115.6(3) .
C24 C23 C18 122.4(3) .
C22 C23 C18 122.1(3) .
C23 C24 C25 120.0(4) .
C23 C24 H24 120.0 .
C25 C24 H24 120.0 .
N3 C25 C24 124.1(4) .
N3 C25 H25 117.9 .
C24 C25 H25 117.9 .
C16 N2 C20 115.2(4) .
C21 N3 C25 115.8(3) .
N4 C26 C27 125.4(4) .
N4 C26 H26 117.3 .
C27 C26 H26 117.3 .
C26 C27 C28 120.0(4) .
C26 C27 H27 120.0 .
C28 C27 H27 120.0 .
C27 C28 C29 114.5(3) .
C27 C28 C28 122.1(4) 3
C29 C28 C28 123.4(4) 3
C30 C29 C28 121.1(3) .
C30 C29 H29 119.5 .
C28 C29 H29 119.5 .
N4 C30 C29 124.4(4) .
N4 C30 H30 117.8 .
C29 C30 H30 117.8 .
C30 N4 C26 114.7(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C6 1.748(3) .
C1 C2 1.365(4) .
C1 C12 1.388(5) .
C1 H1 0.9300 .
C2 C3 1.401(4) .
C2 H2 0.9300 .
C3 C10 1.398(4) .
C3 C4 1.433(4) .
C4 C5 1.394(4) .
C4 C9 1.412(4) .
C5 C6 1.373(4) .
C5 H5 0.9300 .
C6 C7 1.393(5) .
C7 C8 1.366(5) .
C7 H7 0.9300 .
C8 C9 1.385(4) .
C8 H8 0.9300 .
C9 N1 1.376(4) .
C10 N1 1.392(4) .
C10 C11 1.396(5) .
C11 C12 1.386(5) .
C11 H11 0.9300 .
C12 C13 1.520(5) .
C13 C14 1.509(5) .
C13 C15 1.512(5) .
C13 H13 0.9800 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 O1 1.198(4) .
C15 O2 1.281(4) .
N1 H1N 0.958(10) .
O2 H2O 0.963(10) .
C16 N2 1.310(5) .
C16 C17 1.389(6) .
C16 H16 0.9300 .
C17 C18 1.359(5) .
C17 H17 0.9300 .
C18 C19 1.359(5) .
C18 C23 1.486(4) .
C19 C20 1.374(6) .
C19 H19 0.9300 .
C20 N2 1.317(5) .
C20 H20 0.9300 .
C21 N3 1.305(5) .
C21 C22 1.377(5) .
C21 H21 0.9300 .
C22 C23 1.373(5) .
C22 H22 0.9300 .
C23 C24 1.368(5) .
C24 C25 1.384(5) .
C24 H24 0.9300 .
C25 N3 1.312(5) .
C25 H25 0.9300 .
C26 N4 1.320(5) .
C26 C27 1.371(6) .
C26 H26 0.9300 .
C27 C28 1.380(5) .
C27 H27 0.9300 .
C28 C29 1.382(4) .
C28 C28 1.476(6) 3
C29 C30 1.371(5) .
C29 H29 0.9300 .
C30 N4 1.310(5) .
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 -0.5(5) . .
C1 C2 C3 C10 0.4(4) . .
C1 C2 C3 C4 -178.1(3) . .
C10 C3 C4 C5 179.5(3) . .
C2 C3 C4 C5 -1.8(6) . .
C10 C3 C4 C9 -0.4(3) . .
C2 C3 C4 C9 178.3(3) . .
C9 C4 C5 C6 -0.3(4) . .
C3 C4 C5 C6 179.8(3) . .
C4 C5 C6 C7 0.0(5) . .
C4 C5 C6 Cl1 177.9(2) . .
C5 C6 C7 C8 -0.3(5) . .
Cl1 C6 C7 C8 -178.3(3) . .
C6 C7 C8 C9 1.0(5) . .
C7 C8 C9 N1 178.8(3) . .
C7 C8 C9 C4 -1.3(5) . .
C5 C4 C9 N1 -179.1(3) . .
C3 C4 C9 N1 0.8(3) . .
C5 C4 C9 C8 0.9(4) . .
C3 C4 C9 C8 -179.1(3) . .
C2 C3 C10 N1 -179.1(3) . .
C4 C3 C10 N1 -0.2(3) . .
C2 C3 C10 C11 -0.1(4) . .
C4 C3 C10 C11 178.8(3) . .
N1 C10 C11 C12 178.6(3) . .
C3 C10 C11 C12 -0.2(5) . .
C10 C11 C12 C1 0.1(5) . .
C10 C11 C12 C13 -177.4(3) . .
C2 C1 C12 C11 0.2(5) . .
C2 C1 C12 C13 177.8(3) . .
C11 C12 C13 C14 66.9(4) . .
C1 C12 C13 C14 -110.6(4) . .
C11 C12 C13 C15 -60.8(4) . .
C1 C12 C13 C15 121.7(4) . .
C14 C13 C15 O1 -15.9(5) . .
C12 C13 C15 O1 111.6(4) . .
C14 C13 C15 O2 166.2(4) . .
C12 C13 C15 O2 -66.4(4) . .
C8 C9 N1 C10 179.0(3) . .
C4 C9 N1 C10 -0.9(3) . .
C11 C10 N1 C9 -178.2(3) . .
C3 C10 N1 C9 0.7(3) . .
N2 C16 C17 C18 1.2(7) . .
C16 C17 C18 C19 -3.1(6) . .
C16 C17 C18 C23 177.5(4) . .
C17 C18 C19 C20 3.0(7) . .
C23 C18 C19 C20 -177.6(4) . .
C18 C19 C20 N2 -1.1(8) . .
N3 C21 C22 C23 0.3(7) . .
C21 C22 C23 C24 0.2(6) . .
C21 C22 C23 C18 -179.4(4) . .
C17 C18 C23 C24 -167.2(4) . .
C19 C18 C23 C24 13.5(5) . .
C17 C18 C23 C22 12.4(5) . .
C19 C18 C23 C22 -166.9(4) . .
C22 C23 C24 C25 -0.7(5) . .
C18 C23 C24 C25 179.0(3) . .
C23 C24 C25 N3 0.7(6) . .
C17 C16 N2 C20 0.8(7) . .
C19 C20 N2 C16 -0.9(7) . .
C22 C21 N3 C25 -0.3(7) . .
C24 C25 N3 C21 -0.1(6) . .
N4 C26 C27 C28 -1.0(8) . .
C26 C27 C28 C29 1.3(6) . .
C26 C27 C28 C28 -179.1(4) . 3
C27 C28 C29 C30 -0.3(5) . .
C28 C28 C29 C30 -179.9(4) 3 .
C28 C29 C30 N4 -1.2(7) . .
C29 C30 N4 C26 1.4(6) . .
C27 C26 N4 C30 -0.3(7) . .
