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#$Date: 2016-03-24 02:14:06 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179563 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/32/4503272.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_4503272
loop_
_publ_author_name
'Friščić, Tomislav'
'Trask, Andrew V.'
'Motherwell, W. D. S.'
'Jones, W.'
_publ_section_title
;
 Guest-Directed Assembly of Caffeine and Succinic Acid into Topologically
 Different Heteromolecular Host Networks upon Grinding
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1605
_journal_paper_doi               10.1021/cg700929e
_journal_volume                  8
_journal_year                    2008
_chemical_formula_moiety         '4(C8 H10 N4 O2), (C4 H6 O4), 2(C1 H1 Cl3)'
_chemical_formula_sum            'C38 H48 Cl6 N16 O12'
_chemical_formula_weight         1133.1
_chemical_name_common            2.(CHCl3)2
_chemical_name_systematic
;
 caffeine-succinic acid-chloroform 4/1/2
;
_space_group_IT_number           64
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2ac 2'
_symmetry_space_group_name_H-M   'C m c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.64390(10)
_cell_length_b                   23.2514(4)
_cell_length_c                   33.5615(7)
_cell_measurement_reflns_used    14947
_cell_measurement_temperature    240(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      1.00
_cell_volume                     5184.58(16)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_data_reduction
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_diffrn_ambient_temperature      240(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_sigmaI/netI    0.0462
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            14049
_diffrn_reflns_theta_full        27.45
_diffrn_reflns_theta_max         27.45
_diffrn_reflns_theta_min         3.56
_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2344
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.710
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.198
_refine_ls_extinction_coef       0.0107(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3152
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1340
_refine_ls_R_factor_gt           0.0890
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1545P)²+10.5169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2459
_refine_ls_wR_factor_ref         0.2849
_reflns_number_gt                2077
_reflns_number_total             3152
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg700929e-file003.cif
_cod_data_source_block           2.(CHCl3)2
_cod_original_sg_symbol_H-M      Cmca
_cod_database_code               4503272
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, -z'
'x, -y+1/2, z+1/2'
'x, y+1/2, -z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, -z'
'x+1/2, -y+1, z+1/2'
'x+1/2, y+1, -z+1/2'
'-x, -y, -z'
'-x, y, z'
'-x, y-1/2, -z-1/2'
'-x, -y-1/2, z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, z'
'-x+1/2, y, -z-1/2'
'-x+1/2, -y, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0000 0.92948(13) 0.48820(11) 0.0565(10) Uani 1 2 d S . .
O2 O 1.0000 0.85818(15) 0.61493(11) 0.0580(10) Uani 1 2 d S . .
O3 O 1.0000 0.54955(16) 0.29754(12) 0.0609(10) Uani 1 2 d S . .
O4 O 1.0000 0.71755(19) 0.36809(12) 0.0707(12) Uani 1 2 d S . .
O5 O 0.5000 0.90309(14) 0.53351(11) 0.0582(10) Uani 1 2 d S . .
O6 O 0.5000 0.87895(14) 0.46945(11) 0.0591(10) Uani 1 2 d S . .
H6 H 0.5000 0.8458 0.4787 0.089 Uiso 1 2 calc SR . .
N1 N 1.0000 0.73288(14) 0.50514(12) 0.0402(9) Uani 1 2 d S . .
N2 N 1.0000 0.80422(15) 0.46061(11) 0.0399(9) Uani 1 2 d S . .
N3 N 1.0000 0.89336(14) 0.55181(11) 0.0385(9) Uani 1 2 d S . .
N4 N 1.0000 0.79333(14) 0.56486(11) 0.0398(9) Uani 1 2 d S . .
N5 N 1.0000 0.7210(2) 0.22845(14) 0.0590(12) Uani 1 2 d S . .
N6 N 1.0000 0.62521(19) 0.22271(12) 0.0489(10) Uani 1 2 d S . .
N7 N 1.0000 0.63435(18) 0.33270(12) 0.0465(10) Uani 1 2 d S . .
N8 N 1.0000 0.72474(19) 0.30044(13) 0.0540(11) Uani 1 2 d S . .
C1 C 1.0000 0.74753(19) 0.46667(14) 0.0426(10) Uani 1 2 d S . .
H1 H 1.0000 0.7205 0.4459 0.051 Uiso 1 2 calc SR . .
C2 C 1.0000 0.82883(18) 0.49822(13) 0.0374(9) Uani 1 2 d S . .
C3 C 1.0000 0.88783(18) 0.51014(14) 0.0379(10) Uani 1 2 d S . .
C4 C 1.0000 0.84872(19) 0.57925(14) 0.0412(10) Uani 1 2 d S . .
C5 C 1.0000 0.78390(17) 0.52442(13) 0.0343(9) Uani 1 2 d S . .
C6 C 1.0000 0.8354(2) 0.42324(16) 0.0616(15) Uani 1 2 d S . .
H6A H 1.0000 0.8764 0.4285 0.092 Uiso 1 2 calc SR . .
H6B H 0.8808 0.8253 0.4081 0.092 Uiso 0.50 1 calc PR . .
H6C H 1.1192 0.8253 0.4081 0.092 Uiso 0.50 1 calc PR . .
C7 C 1.0000 0.95179(18) 0.56833(16) 0.0507(12) Uani 1 2 d S . .
H7A H 1.0000 0.9795 0.5467 0.076 Uiso 1 2 calc SR . .
H7B H 1.1192 0.9572 0.5846 0.076 Uiso 0.50 1 calc PR . .
H7C H 0.8808 0.9572 0.5846 0.076 Uiso 0.50 1 calc PR . .
C8 C 1.0000 0.7453(2) 0.59347(14) 0.0515(12) Uani 1 2 d S . .
H8A H 1.0000 0.7604 0.6204 0.077 Uiso 1 2 calc SR . .
H8B H 1.1192 0.7220 0.5894 0.077 Uiso 0.50 1 calc PR . .
H8C H 0.8808 0.7220 0.5894 0.077 Uiso 0.50 1 calc PR . .
C9 C 1.0000 0.6764(3) 0.20371(16) 0.0548(13) Uani 1 2 d S . .
H9 H 1.0000 0.6801 0.1758 0.066 Uiso 1 2 calc SR . .
C10 C 1.0000 0.6382(2) 0.26288(14) 0.0419(10) Uani 1 2 d S . .
C11 C 1.0000 0.6024(2) 0.29721(14) 0.0447(11) Uani 1 2 d S . .
C12 C 1.0000 0.6941(2) 0.33544(15) 0.0492(12) Uani 1 2 d S . .
C13 C 1.0000 0.6967(2) 0.26480(14) 0.0455(11) Uani 1 2 d S . .
C14 C 1.0000 0.5693(3) 0.20360(18) 0.0586(14) Uani 1 2 d S . .
H14A H 1.0000 0.5394 0.2238 0.088 Uiso 1 2 calc SR . .
H14B H 1.1192 0.5655 0.1871 0.088 Uiso 0.50 1 calc PR . .
H14C H 0.8808 0.5655 0.1871 0.088 Uiso 0.50 1 calc PR . .
C15 C 1.0000 0.6022(3) 0.37033(17) 0.0638(15) Uani 1 2 d S . .
H15A H 1.0000 0.5613 0.3647 0.096 Uiso 1 2 calc SR . .
H15B H 0.8808 0.6120 0.3856 0.096 Uiso 0.50 1 calc PR . .
H15C H 1.1192 0.6120 0.3856 0.096 Uiso 0.50 1 calc PR . .
C16 C 1.0000 0.7872(3) 0.3017(2) 0.092(2) Uani 1 2 d S . .
H16A H 1.0000 0.7999 0.3293 0.138 Uiso 1 2 calc SR . .
H16B H 0.8808 0.8017 0.2884 0.138 Uiso 0.50 1 calc PR . .
H16C H 1.1192 0.8017 0.2884 0.138 Uiso 0.50 1 calc PR . .
C17 C 0.5000 0.91699(17) 0.49938(14) 0.0402(10) Uani 1 2 d S . .
C18 C 0.5000 0.97792(18) 0.48407(15) 0.0506(12) Uani 1 2 d S . .
H18A H 0.6191 0.9836 0.4673 0.061 Uiso 0.50 1 calc PR . .
H18B H 0.3809 0.9836 0.4673 0.061 Uiso 0.50 1 calc PR . .
C19 C 1.0000 0.4308(5) 0.3337(3) 0.123(13) Uani 0.50 2 d SPD . 1
H19 H 1.0000 0.4692 0.3209 0.148 Uiso 0.50 2 calc SPR . 1
Cl2 Cl 0.7728(16) 0.4357(3) 0.3571(4) 0.397(11) Uani 0.50 1 d PD A 1
Cl1 Cl 1.0000 0.3903(7) 0.2917(5) 0.377(13) Uani 0.50 2 d SPD B 1
Cl4 Cl 1.0000 0.4203(3) 0.3784(2) 0.145(3) Uani 0.50 2 d SP . 2
Cl5 Cl 1.3400(19) 0.4311(3) 0.3329(4) 0.150(4) Uani 0.25 1 d P . 2
Cl6 Cl 1.0000 0.3611(2) 0.3081(2) 0.1054(15) Uani 0.50 2 d SP . 2
C20 C 1.061(5) 0.408(2) 0.3330(14) 0.23(3) Uani 0.25 1 d P C 2
H20 H 0.9965 0.4407 0.3193 0.281 Uiso 0.50 2 calc SPR C 2
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C5 103.8(4) . .
C1 N2 C2 105.6(4) . .
C1 N2 C6 128.8(4) . .
C2 N2 C6 125.6(4) . .
C4 N3 C3 126.3(4) . .
C4 N3 C7 116.2(4) . .
C3 N3 C7 117.5(4) . .
C5 N4 C4 119.7(3) . .
C5 N4 C8 121.5(4) . .
C4 N4 C8 118.7(4) . .
C9 N5 C13 103.9(5) . .
C9 N6 C10 105.6(4) . .
C9 N6 C14 125.6(5) . .
C10 N6 C14 128.8(5) . .
C12 N7 C11 125.8(4) . .
C12 N7 C15 116.9(4) . .
C11 N7 C15 117.4(4) . .
C13 N8 C12 120.1(4) . .
C13 N8 C16 120.3(5) . .
C12 N8 C16 119.6(5) . .
N2 C1 N1 113.5(4) . .
C5 C2 N2 105.7(4) . .
C5 C2 C3 123.7(4) . .
N2 C2 C3 130.6(4) . .
O1 C3 N3 122.0(4) . .
O1 C3 C2 126.5(4) . .
N3 C3 C2 111.5(4) . .
O2 C4 N4 121.0(4) . .
O2 C4 N3 121.2(4) . .
N4 C4 N3 117.9(4) . .
N1 C5 C2 111.3(4) . .
N1 C5 N4 127.8(4) . .
C2 C5 N4 120.9(4) . .
N5 C9 N6 113.1(5) . .
C13 C10 N6 105.3(4) . .
C13 C10 C11 123.1(4) . .
N6 C10 C11 131.6(4) . .
O3 C11 N7 121.5(5) . .
O3 C11 C10 126.4(5) . .
N7 C11 C10 112.2(4) . .
O4 C12 N8 122.2(5) . .
O4 C12 N7 120.3(5) . .
N8 C12 N7 117.5(4) . .
N5 C13 C10 112.1(4) . .
N5 C13 N8 126.5(5) . .
C10 C13 N8 121.3(4) . .
O5 C17 O6 122.9(4) . .
O5 C17 C18 125.7(4) . .
O6 C17 C18 111.4(4) . .
C18 C18 C17 113.9(5) 9_676 .
Cl1 C19 Cl2 114.9(7) . .
Cl1 C19 Cl2 114.9(7) . 10_755
Cl2 C19 Cl2 124.4(13) . 10_755
C20 Cl4 C20 29(2) 10_755 .
C20 Cl5 Cl5 163.7(15) . 10_855
C20 Cl6 C20 33(3) . 10_755
Cl6 C20 Cl4 129(3) . .
Cl6 C20 Cl5 118.9(19) . .
Cl4 C20 Cl5 101.1(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.217(5) .
O2 C4 1.218(6) .
O3 C11 1.228(6) .
O4 C12 1.225(6) .
O5 C17 1.190(5) .
O6 C17 1.339(5) .
N1 C1 1.335(6) .
N1 C5 1.351(5) .
N2 C1 1.334(6) .
N2 C2 1.386(5) .
N2 C6 1.448(6) .
N3 C4 1.388(6) .
N3 C3 1.404(6) .
N3 C7 1.467(5) .
N4 C5 1.375(6) .
N4 C4 1.375(6) .
N4 C8 1.472(5) .
N5 C9 1.327(7) .
N5 C13 1.345(6) .
N6 C9 1.351(7) .
N6 C10 1.381(6) .
N6 C14 1.451(6) .
N7 C12 1.391(7) .
N7 C11 1.404(6) .
N7 C15 1.468(6) .
N8 C13 1.363(6) .
N8 C12 1.374(7) .
N8 C16 1.453(8) .
C2 C5 1.365(6) .
C2 C3 1.429(6) .
C10 C13 1.362(7) .
C10 C11 1.421(7) .
C17 C18 1.507(6) .
C18 C18 1.483(10) 9_676
C19 Cl1 1.695(5) .
C19 Cl2 1.706(5) .
C19 Cl2 1.706(5) 10_755
Cl4 C20 1.60(4) 10_755
Cl4 C20 1.60(4) .
Cl5 C20 1.93(4) .
Cl5 Cl5 2.13(3) 10_855
Cl6 C20 1.43(3) .
Cl6 C20 1.43(3) 10_755
