#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:03:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180463 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/32/7213295.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_7213295
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            'C42 H58 N6 O15 S2'
_chemical_formula_weight         951.06
_chemical_name_systematic
; 
Cephradine/alpha-naphthol 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                 108.268(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   23.471(2)
_cell_length_b                   7.1215(10)
_cell_length_c                   14.9304(19)
_cell_measurement_reflns_used    21
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.888
_cell_measurement_theta_min      13.125
_cell_volume                     2369.8(5)
_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-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  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0861
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4988
_diffrn_reflns_theta_full        69.90
_diffrn_reflns_theta_max         69.90
_diffrn_reflns_theta_min         3.97
_diffrn_standards_decay_%        6.414
_diffrn_standards_interval_time  7200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.633
_exptl_absorpt_correction_T_max  1.024
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   experimental
_exptl_crystal_colour            'transparent light yellow-brown'
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'regular platelet'
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_Flack   0.03(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.034
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         4411
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.1431
_refine_ls_R_factor_gt           0.0756
_refine_ls_R_factor_obs          0.0756
_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)+(0.0947P)²+2.0329P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.2188
_refine_ls_wR_factor_gt          0.1792
_refine_ls_wR_factor_obs         0.1792
_refine_ls_wR_factor_ref         0.2188
_reflns_number_gt                2413
_reflns_number_observed          2413
_reflns_number_total             4411
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b001692fsup1.cif
_cod_data_source_block           CEFRAA
_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 (34
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 (47 times).

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               7213295
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 0.17131(8) 0.0682(3) 0.67666(12) 0.0642(5) Uani 1 d . . .
C2 C 0.0937(3) 0.1329(11) 0.6288(4) 0.0589(19) Uani 1 d . . .
H2A H 0.0919 0.2516 0.5961 0.071 Uiso 1 calc R . .
H2B H 0.0742 0.0400 0.5816 0.071 Uiso 1 calc R . .
C3 C 0.0568(3) 0.1531(11) 0.6937(4) 0.0523(16) Uani 1 d . . .
C4 C 0.0802(2) 0.1808(11) 0.7860(4) 0.0486(16) Uani 1 d . . .
N5 N 0.1433(2) 0.1943(8) 0.8268(3) 0.0476(14) Uani 1 d . . .
C6 C 0.1859(3) 0.2244(11) 0.7739(5) 0.0511(17) Uani 1 d . . .
H6 H 0.1891 0.3560 0.7569 0.061 Uiso 1 calc R . .
C7 C 0.2365(3) 0.1618(12) 0.8656(5) 0.0539(17) Uani 1 d . . .
H7 H 0.2614 0.2679 0.8971 0.065 Uiso 1 calc R . .
C8 C 0.1840(2) 0.1260(11) 0.9047(4) 0.0503(19) Uani 1 d . . .
C9 C 0.0453(3) 0.2105(12) 0.8548(5) 0.0555(19) Uani 1 d . . .
C10 C -0.0095(3) 0.1509(14) 0.6437(5) 0.076(2) Uani 1 d . . .
H10A H -0.0166 0.1282 0.5777 0.113 Uiso 1 calc R . .
H10B H -0.0264 0.2700 0.6518 0.113 Uiso 1 calc R . .
H10C H -0.0278 0.0533 0.6694 0.113 Uiso 1 calc R . .
O11 O -0.0008(2) 0.1191(8) 0.8466(4) 0.0797(19) Uani 1 d . . .
O12 O 0.0649(2) 0.3380(8) 0.9150(3) 0.0672(15) Uani 1 d . . .
O13 O 0.17966(18) 0.0537(8) 0.9768(3) 0.0602(13) Uani 1 d . . .
N14 N 0.2716(2) 0.0009(9) 0.8624(4) 0.0530(15) Uani 1 d . . .
H14 H 0.2553 -0.1085 0.8557 0.064 Uiso 1 calc R . .
C15 C 0.3296(3) 0.0171(11) 0.8696(5) 0.0514(18) Uani 1 d . . .
O16 O 0.3558(2) 0.1670(9) 0.8792(5) 0.0849(18) Uani 1 d . . .
C17 C 0.3608(3) -0.1648(11) 0.8616(5) 0.0506(17) Uani 1 d . . .
H17 H 0.3511 -0.2566 0.9036 0.061 Uiso 1 calc R . .
N18 N 0.4263(2) -0.1281(10) 0.8978(4) 0.0600(16) Uani 1 d . . .
H18A H 0.4459 -0.2198 0.8793 0.090 Uiso 1 calc R . .
H18B H 0.4381 -0.1235 0.9605 0.090 Uiso 1 calc R . .
H18C H 0.4343 -0.0189 0.8752 0.090 Uiso 1 calc R . .
C19 C 0.3427(3) -0.2471(11) 0.7645(5) 0.0489(17) Uani 1 d . . .
C20 C 0.3419(4) -0.1259(13) 0.6850(5) 0.071(2) Uani 1 d . . .
H20A H 0.3815 -0.0720 0.6964 0.085 Uiso 1 calc R . .
H20B H 0.3140 -0.0235 0.6816 0.085 Uiso 1 calc R . .
C21 C 0.3237(4) -0.2290(18) 0.5897(6) 0.087(3) Uani 1 d . . .
H21 H 0.3234 -0.1627 0.5359 0.105 Uiso 1 calc R . .
C22 C 0.3090(4) -0.404(2) 0.5817(6) 0.096(4) Uani 1 d . . .
H22 H 0.2984 -0.4564 0.5217 0.115 Uiso 1 calc R . .
C23 C 0.3075(6) -0.5257(16) 0.6587(8) 0.110(4) Uani 1 d . . .
H23A H 0.3336 -0.6325 0.6614 0.131 Uiso 1 calc R . .
H23B H 0.2670 -0.5727 0.6471 0.131 Uiso 1 calc R . .
C24 C 0.3272(4) -0.4241(15) 0.7523(6) 0.076(2) Uani 1 d . . .
H24 H 0.3285 -0.4933 0.8057 0.091 Uiso 1 calc R . .
O30 O 0.4833(10) 0.153(3) 0.2960(13) 0.165(8) Uani 0.50 d P A 1
H30 H 0.4548 0.1576 0.2473 0.247 Uiso 0.50 calc PR A 1
C31 C 0.3865(6) 0.1451(16) 0.4386(12) 0.123(4) Uani 1 d . . .
H31 H 0.3459 0.1391 0.4322 0.147 Uiso 1 calc R . .
C32 C 0.4039(7) 0.1472(18) 0.3619(9) 0.120(4) Uani 1 d . . .
H32 H 0.3754 0.1498 0.3024 0.144 Uiso 1 calc R . .
C33 C 0.4632(7) 0.1456(16) 0.3700(8) 0.101(3) Uani 1 d . . .
H33 H 0.4743 0.1445 0.3155 0.121 Uiso 0.50 calc PR B 2
C34 C 0.5093(5) 0.1456(14) 0.4603(7) 0.092(3) Uani 1 d . . .
C35 C 0.5711(7) 0.1518(16) 0.4704(10) 0.126(4) Uani 1 d . . .
H35 H 0.5838 0.1602 0.4175 0.151 Uiso 1 calc R . .
O40 O 0.7190(2) 0.1475(8) 0.8660(4) 0.0735(15) Uani 1 d . . .
O50 O 0.6085(3) 0.1763(12) 0.8901(5) 0.112(2) Uani 1 d . . .
O60 O 0.4691(6) 0.2181(19) 0.8254(13) 0.267(8) Uani 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 0.0181 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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S1 C2 94.4(3) . . y
C3 C2 S1 119.2(5) . . y
C4 C3 C2 123.5(6) . . y
C4 C3 C10 123.0(6) . . y
C2 C3 C10 113.4(6) . . y
C3 C4 N5 119.5(5) . . y
C3 C4 C9 126.1(5) . . y
N5 C4 C9 114.4(5) . . y
C8 N5 C4 135.2(6) . . y
C8 N5 C6 95.8(4) . . y
C4 N5 C6 125.0(5) . . y
N5 C6 C7 86.9(5) . . y
N5 C6 S1 111.0(5) . . y
C7 C6 S1 115.8(5) . . y
N14 C7 C8 114.9(6) . . y
N14 C7 C6 119.2(6) . . y
C8 C7 C6 84.3(4) . . y
O13 C8 N5 133.0(5) . . y
O13 C8 C7 134.3(5) . . y
N5 C8 C7 92.7(5) . . y
O11 C9 O12 124.3(6) . . y
O11 C9 C4 120.1(7) . . y
O12 C9 C4 115.5(6) . . y
C15 N14 C7 121.0(6) . . y
O16 C15 N14 123.4(7) . . y
O16 C15 C17 121.4(5) . . y
N14 C15 C17 115.2(6) . . y
N18 C17 C19 111.6(5) . . y
N18 C17 C15 107.0(6) . . y
C19 C17 C15 114.5(6) . . y
C24 C19 C20 121.6(7) . . y
C24 C19 C17 119.5(7) . . y
C20 C19 C17 118.9(7) . . y
C19 C20 C21 113.5(8) . . y
C22 C21 C20 122.4(9) . . y
C21 C22 C23 125.3(10) . . y
C22 C23 C24 111.8(9) . . y
C19 C24 C23 125.5(8) . . y
C32 C31 C35 120.9(13) . 2_656 y
C31 C32 C33 120.3(12) . . y
O30 C33 C32 123.0(15) . . y
O30 C33 C34 114.7(15) . . y
C32 C33 C34 122.2(11) . . y
C34 C34 C35 119.8(13) 2_656 . y
C34 C34 C33 117.0(14) 2_656 . y
C35 C34 C33 123.1(11) . . y
C34 C35 C31 119.6(12) . 2_656 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 1.775(7) . y
S1 C2 1.797(7) . y
C2 C3 1.494(9) . y
C3 C4 1.329(8) . y
C3 C10 1.500(9) . y
C4 N5 1.417(7) . y
C4 C9 1.515(8) . y
N5 C8 1.343(8) . y
N5 C6 1.471(7) . y
C6 C7 1.570(9) . y
C7 N14 1.421(9) . y
C7 C8 1.542(8) . y
C8 O13 1.225(7) . y
C9 O11 1.235(8) . y
C9 O12 1.259(9) . y
N14 C15 1.336(7) . y
C15 O16 1.218(9) . y
C15 C17 1.511(10) . y
C17 N18 1.486(8) . y
C17 C19 1.498(9) . y
C19 C24 1.309(11) . y
C19 C20 1.462(10) . y
C20 C21 1.538(13) . y
C21 C22 1.289(15) . y
C22 C23 1.449(15) . y
C23 C24 1.511(13) . y
O30 C33 1.33(2) . y
C31 C32 1.332(17) . y
C31 C35 1.410(17) 2_656 y
C32 C33 1.357(17) . y
C33 C34 1.440(15) . y
C34 C34 1.387(19) 2_656 y
C34 C35 1.410(15) . y
C35 C31 1.410(17) 2_656 y
