#------------------------------------------------------------------------------
#$Date: 2016-02-16 03:10:39 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/32/7213298.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_7213298
loop_
_publ_author_name
'Kemperman, Gerardus J.'
'de Gelder, Rene'
'Dommerholt, Frederik J.'
'Raemakers-Franken, Petronella C.'
'Klunder, Antonius J. H.'
'Zwanenburg, Binne'
_publ_contact_author
;
        Dr. R. de Gelder
        Crystallography Department
        University of Nijmegen
        Toernooiveld 1
        6525 ED  Nijmegen
        The Netherlands
;
_publ_section_title
;
 Induced fit phenomena in clathrate structures of cephalosporins
;
_journal_issue                   7
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 2'
_journal_page_first              1425
_journal_paper_doi               10.1039/b001692f
_journal_year                    2000
_chemical_formula_sum            'C44 H57 N6 O13.5 S2'
_chemical_formula_weight         950.08
_chemical_name_systematic
; 
Cephradine/2-acetonaphthone complex
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             1999-05-04
_audit_creation_method           'SHELXL, adapted and expanded'
_cell_angle_alpha                90.00
_cell_angle_beta                 108.580(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   23.3855(5)
_cell_length_b                   7.1965(3)
_cell_length_c                   14.7588(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.191
_cell_measurement_theta_min      39.960
_cell_volume                     2354.36(13)
_computing_data_collection
;
CAD4 EXPRESS (Enraf-Nonius, 1994)
;
_computing_data_reduction
;
local programs (Smits et al., 1988),
profile analysis (Lehman & Larsen, 1974, Grant & Gabe, 1978),
EMPABS (North et al., 1968)
;
_computing_molecular_graphics
;
PLUTON (Spek, 1993),
PLATON (Spek, 1990, 1995)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution
;
DIRDIF (Beurskens et al., 1996),
;
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Nonius CAD4'
_diffrn_measurement_method       ω/2θ-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0120
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2507
_diffrn_reflns_theta_full        69.88
_diffrn_reflns_theta_max         69.88
_diffrn_reflns_theta_min         3.16
_diffrn_standards_decay_%        2.010
_diffrn_standards_interval_time  900
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.620
_exptl_absorpt_correction_T_max  1.030
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   experimental
_exptl_crystal_colour            'transparent colourless'
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'regular thick needle'
_exptl_crystal_F_000             1006
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.029
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     445
_refine_ls_number_reflns         2410
_refine_ls_number_restraints     71
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0329
_refine_ls_R_factor_obs          0.0329
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[σ²(Fo²)+(0.0697P)²+0.4696P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0914
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_obs         0.0899
_refine_ls_wR_factor_ref         0.0914
_reflns_number_gt                2329
_reflns_number_observed          2329
_reflns_number_total             2410
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b001692fsup1.cif
_cod_data_source_block           CF2ACN
_cod_depositor_comments
;
The following automatic conversions were performed:
'_publ_contact_autor' tag replaced with '_publ_contact_author'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26 (45
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.2 from 2011-04-26 (70 times).

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2354.36(11)
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C44 H57 N6 O13.50 S2'
_cod_database_code               7213298
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.17453(3) 0.10077(11) 0.67852(4) 0.0591(2) Uani 1 d . . .
C2 C 0.09633(14) 0.1698(5) 0.62657(18) 0.0554(6) Uani 1 d . . .
H2A H 0.0940(18) 0.287(7) 0.588(3) 0.084(12) Uiso 1 d . . .
H2B H 0.0799(13) 0.083(5) 0.584(2) 0.049(7) Uiso 1 d . . .
C3 C 0.05883(11) 0.1837(4) 0.69290(16) 0.0474(5) Uani 1 d . . .
C4 C 0.08196(9) 0.2030(4) 0.78779(15) 0.0425(5) Uani 1 d . . .
N5 N 0.14502(8) 0.2187(3) 0.83029(12) 0.0426(4) Uani 1 d . . .
C6 C 0.18889(11) 0.2501(4) 0.78036(18) 0.0467(5) Uani 1 d . . .
H6 H 0.1899(11) 0.369(4) 0.7600(18) 0.038(6) Uiso 1 d . . .
C7 C 0.23840(10) 0.1856(4) 0.87248(19) 0.0473(5) Uani 1 d . . .
H7 H 0.2665(13) 0.288(5) 0.904(2) 0.055(8) Uiso 1 d . . .
C8 C 0.18539(9) 0.1482(4) 0.91064(15) 0.0457(6) Uani 1 d . . .
C9 C 0.04544(9) 0.2310(4) 0.85483(16) 0.0461(5) Uani 1 d . . .
C10 C -0.00775(13) 0.1850(6) 0.6399(2) 0.0665(8) Uani 1 d . . .
H10A H -0.0207(18) 0.068(7) 0.615(3) 0.080(12) Uiso 1 d . . .
H10B H -0.0157(18) 0.274(7) 0.578(3) 0.085(12) Uiso 1 d . . .
H10C H -0.0309(18) 0.224(8) 0.681(3) 0.093(13) Uiso 1 d . . .
O11 O -0.00119(8) 0.1377(4) 0.84215(16) 0.0702(6) Uani 1 d . . .
O12 O 0.06451(8) 0.3534(4) 0.91760(12) 0.0603(5) Uani 1 d . . .
O13 O 0.18048(7) 0.0791(4) 0.98253(11) 0.0584(5) Uani 1 d . . .
N14 N 0.27311(8) 0.0229(3) 0.86825(17) 0.0492(5) Uani 1 d . . .
H14 H 0.2560(17) -0.083(6) 0.860(3) 0.074(11) Uiso 1 d . . .
C15 C 0.33012(9) 0.0366(4) 0.86912(15) 0.0412(5) Uani 1 d . . .
O16 O 0.35632(9) 0.1845(3) 0.87609(19) 0.0721(6) Uani 1 d . . .
C17 C 0.36088(9) -0.1465(4) 0.86153(15) 0.0400(5) Uani 1 d . . .
H17 H 0.3531(11) -0.239(4) 0.9022(19) 0.042(7) Uiso 1 d . . .
N18 N 0.42723(8) -0.1111(4) 0.89655(14) 0.0496(5) Uani 1 d . . .
H18A H 0.4548(18) -0.214(7) 0.880(3) 0.087(12) Uiso 1 d . . .
H18B H 0.4397(12) -0.104(4) 0.964(2) 0.047(7) Uiso 1 d . . .
H18C H 0.4395(15) 0.005(6) 0.875(2) 0.060(9) Uiso 1 d . . .
C19 C 0.34049(9) -0.2264(3) 0.76145(15) 0.0412(5) Uani 1 d . . .
C20 C 0.34217(14) -0.1036(5) 0.68151(18) 0.0580(6) Uani 1 d . . .
H20A H 0.3878(18) -0.061(7) 0.697(3) 0.087(12) Uiso 1 d . . .
H20B H 0.3128(19) 0.006(8) 0.683(3) 0.087(12) Uiso 1 d . . .
C21 C 0.32349(15) -0.2024(7) 0.5868(2) 0.0733(9) Uani 1 d . . .
H21 H 0.327(2) -0.110(9) 0.527(4) 0.121(17) Uiso 1 d . . .
C22 C 0.30606(17) -0.3754(7) 0.5750(2) 0.0803(11) Uani 1 d . . .
H22 H 0.2975(18) -0.413(8) 0.513(3) 0.090(12) Uiso 1 d . . .
C23 C 0.3020(3) -0.4953(7) 0.6533(3) 0.0893(11) Uani 1 d . . .
H23A H 0.338(2) -0.574(8) 0.660(3) 0.103(15) Uiso 1 d . . .
H23B H 0.255(3) -0.555(12) 0.634(4) 0.17(3) Uiso 1 d . . .
C24 C 0.32282(14) -0.4026(5) 0.7490(2) 0.0604(6) Uani 1 d . . .
H24 H 0.3210(15) -0.469(6) 0.800(3) 0.072(10) Uiso 1 d . . .
C30 C 0.5958(3) 0.1918(9) 0.6835(6) 0.0668(15) Uani 0.50 d PD . .
C31 C 0.5339(3) 0.1902(9) 0.6606(5) 0.0593(14) Uani 0.50 d PD . .
H31 H 0.5168 0.1953 0.7095 0.071 Uiso 0.50 calc PR . .
C32 C 0.4954(3) 0.1811(19) 0.5643(6) 0.068(3) Uani 0.50 d PD . .
C33 C 0.4325(4) 0.1841(16) 0.5430(7) 0.084(3) Uani 0.50 d PD . .
H33 H 0.4153 0.1881 0.5918 0.101 Uiso 0.50 calc PR . .
C34 C 0.3965(6) 0.181(3) 0.4481(8) 0.113(6) Uani 0.50 d PD . .
H34 H 0.3548 0.1826 0.4335 0.136 Uiso 0.50 calc PR . .
C35 C 0.4214(6) 0.1753(14) 0.3745(7) 0.116(6) Uani 0.50 d PD . .
H35 H 0.3967 0.1722 0.3111 0.140 Uiso 0.50 calc PR . .
C36 C 0.4836(6) 0.174(2) 0.3970(9) 0.103(5) Uani 0.50 d PD . .
H36 H 0.5004 0.1723 0.3477 0.123 Uiso 0.50 calc PR . .
C37 C 0.5217(5) 0.1760(12) 0.4910(6) 0.084(3) Uani 0.50 d PD . .
C38 C 0.5847(5) 0.173(2) 0.5147(8) 0.100(6) Uani 0.50 d PD . .
H38 H 0.6021 0.1638 0.4664 0.120 Uiso 0.50 calc PR . .
C39 C 0.6213(4) 0.1839(13) 0.6092(8) 0.091(3) Uani 0.50 d PD . .
H39 H 0.6630 0.1860 0.6236 0.109 Uiso 0.50 calc PR . .
C40 C 0.6358(3) 0.2069(8) 0.7862(6) 0.0759(19) Uani 0.50 d P A 1
O41 O 0.6897(3) 0.2031(9) 0.8022(6) 0.107(2) Uani 0.50 d P A 1
C41 C 0.6073(11) 0.226(2) 0.8687(18) 0.079(5) Uani 0.50 d P A 1
H41A H 0.5993 0.1050 0.8888 0.118 Uiso 0.50 calc PR A 1
H41B H 0.5704 0.2952 0.8460 0.118 Uiso 0.50 calc PR A 1
H41C H 0.6350 0.2905 0.9217 0.118 Uiso 0.50 calc PR A 1
O40 O 0.7167(2) 0.1721(7) 0.8622(3) 0.0639(10) Uani 0.50 d P B 2
O50 O 0.6070(8) 0.216(2) 0.8872(14) 0.102(5) Uani 0.50 d P C 2
O60 O 0.4585(2) 0.2550(8) 0.8049(4) 0.163(2) Uani 1 d . . .
O70 O 0.5000 0.264(7) 1.0000 0.330(19) Uani 0.50 d SP . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_publ_flag
C6 S1 C2 94.86(12) . y
C3 C2 S1 117.36(17) . y
C4 C3 C10 123.4(2) . y
C4 C3 C2 124.1(2) . y
C10 C3 C2 112.5(2) . y
C3 C4 N5 119.34(19) . y
C3 C4 C9 125.06(19) . y
N5 C4 C9 115.25(18) . y
C8 N5 C4 134.1(2) . y
C8 N5 C6 95.40(17) . y
C4 N5 C6 126.26(18) . y
N5 C6 C7 87.67(17) . y
N5 C6 S1 110.90(17) . y
C7 C6 S1 116.38(18) . y
N14 C7 C8 113.9(2) . y
N14 C7 C6 118.7(2) . y
C8 C7 C6 84.82(16) . y
O13 C8 N5 133.32(19) . y
O13 C8 C7 134.8(2) . y
N5 C8 C7 91.83(18) . y
O11 C9 O12 125.4(2) . y
O11 C9 C4 118.7(2) . y
O12 C9 C4 115.8(2) . y
C15 N14 C7 121.1(2) . y
O16 C15 N14 122.8(2) . y
O16 C15 C17 121.78(17) . y
N14 C15 C17 115.5(2) . y
N18 C17 C19 111.86(16) . y
N18 C17 C15 106.9(2) . y
C19 C17 C15 113.02(18) . y
C24 C19 C20 122.9(2) . y
C24 C19 C17 119.0(2) . y
C20 C19 C17 118.0(2) . y
C19 C20 C21 112.6(3) . y
C22 C21 C20 124.2(3) . y
C21 C22 C23 123.4(3) . y
C22 C23 C24 113.4(4) . y
C19 C24 C23 123.4(3) . y
C31 C30 C39 118.8(8) . y
C31 C30 C40 120.9(6) . y
C39 C30 C40 120.3(7) . y
C31 C30 C34 100.0(7) 2_656 y
C39 C30 C34 18.9(5) 2_656 y
C40 C30 C34 139.1(6) 2_656 y
C30 C31 C32 121.8(7) . y
C33 C32 C37 120.9(9) . y
C33 C32 C31 120.5(7) . y
C37 C32 C31 118.6(8) . y
C33 C32 C32 102.3(7) 2_656 y
C37 C32 C32 18.7(5) 2_656 y
C31 C32 C32 137.1(8) 2_656 y
C34 C33 C32 118.8(11) . y
C33 C34 C35 121.4(12) . y
C33 C34 C30 139.9(11) 2_656 y
C35 C34 C30 19.0(6) 2_656 y
C36 C35 C34 118.9(10) . y
C36 C35 C37 56.6(6) 2_656 y
C34 C35 C37 62.4(7) 2_656 y
C35 C36 C37 122.0(11) . y
C36 C37 C38 122.6(9) . y
C36 C37 C32 118.0(10) . y
C38 C37 C32 119.4(9) . y
C36 C37 C35 178.4(9) 2_656 y
C38 C37 C35 56.0(6) 2_656 y
C32 C37 C35 63.5(6) 2_656 y
C39 C38 C37 120.9(8) . y
C38 C39 C30 120.4(8) . y
O41 C40 C30 118.0(8) . y
O41 C40 C41 121.7(11) . y
C30 C40 C41 120.3(10) . y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.790(3) . y
S1 C2 1.813(3) . y
C2 C3 1.511(4) . y
C3 C4 1.338(3) . y
C3 C10 1.503(3) . y
C4 N5 1.411(3) . y
C4 C9 1.512(3) . y
N5 C8 1.357(3) . y
N5 C6 1.459(3) . y
C6 C7 1.550(4) . y
C7 N14 1.437(3) . y
C7 C8 1.540(3) . y
C8 O13 1.210(3) . y
C9 O11 1.243(3) . y
C9 O12 1.253(3) . y
N14 C15 1.333(3) . y
C15 O16 1.216(3) . y
C15 C17 1.523(3) . y
C17 N18 1.493(3) . y
C17 C19 1.513(3) . y
C19 C24 1.328(4) . y
C19 C20 1.485(4) . y
C20 C21 1.504(4) . y
C21 C22 1.304(6) . y
C22 C23 1.470(6) . y
C23 C24 1.496(5) . y
C30 C31 1.379(8) . y
C30 C39 1.406(10) . y
C30 C40 1.510(11) . y
C30 C34 2.009(15) 2_656 y
C31 C32 1.421(9) . y
C32 C33 1.403(10) . y
C32 C37 1.406(11) . y
C32 C32 1.977(18) 2_656 y
C33 C34 1.385(11) . y
C34 C35 1.387(12) . y
C34 C30 2.009(15) 2_656 y
C35 C36 1.386(13) . y
C35 C37 2.007(13) 2_656 y
C36 C37 1.390(10) . y
C37 C38 1.400(11) . y
C37 C35 2.007(13) 2_656 y
C38 C39 1.387(13) . y
C40 O41 1.206(8) . y
C40 C41 1.57(3) . y
