#------------------------------------------------------------------------------
#$Date: 2016-02-16 02:10:39 +0100 (mar 16 de feb de 2016) $
#$Revision: 176453 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/32/7213297.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_7213297
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 O14.5 S2'
_chemical_formula_weight         943.06
_chemical_name_systematic
; 
Cephradine/naphthalene 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                 108.571(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   23.4584(6)
_cell_length_b                   7.1179(2)
_cell_length_c                   14.8922(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.469
_cell_measurement_theta_min      40.492
_cell_volume                     2357.14(12)
_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  0.0149
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2522
_diffrn_reflns_theta_full        69.91
_diffrn_reflns_theta_max         69.91
_diffrn_reflns_theta_min         3.13
_diffrn_standards_decay_%        2.366
_diffrn_standards_interval_time  7200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.629
_exptl_absorpt_correction_T_max  1.072
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   experimental
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'regular platelet'
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.149
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         2425
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0435
_refine_ls_R_factor_obs          0.0435
_refine_ls_shift/esd_max         0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[σ²(Fo²)+(0.0814P)²+1.5154P] where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1389
_refine_ls_wR_factor_gt          0.1229
_refine_ls_wR_factor_obs         0.1229
_refine_ls_wR_factor_ref         0.1389
_reflns_number_gt                2236
_reflns_number_observed          2236
_reflns_number_total             2425
_reflns_observed_criterion       >2sigma(I)
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b001692fsup1.cif
_cod_data_source_block           CEFRNA
_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 (33
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 (45 times).

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_cell_volume        2357.12(12)
_cod_original_sg_symbol_H-M      'C 2'
_cod_original_formula_sum        'C42 H58 N6 O14.50 S2'
_cod_database_code               7213297
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
S1 S 0.17083(5) 1.06906(17) 0.67615(7) 0.0492(3) Uani 1 d .
C2 C 0.09196(19) 1.1328(7) 0.6269(3) 0.0466(10) Uani 1 d .
H2A H 0.0897 1.2524 0.5947 0.056 Uiso 1 calc R
H2B H 0.0725 1.0402 0.5792 0.056 Uiso 1 calc R
C3 C 0.05593(17) 1.1493(7) 0.6942(3) 0.0414(8) Uani 1 d .
C4 C 0.07985(14) 1.1743(6) 0.7870(2) 0.0353(8) Uani 1 d .
N5 N 0.14308(12) 1.1925(5) 0.8272(2) 0.0355(7) Uani 1 d .
C6 C 0.18560(16) 1.2261(6) 0.7752(3) 0.0387(8) Uani 1 d .
H6 H 0.1883 1.3583 0.7585 0.046 Uiso 1 calc R
C7 C 0.23652(15) 1.1634(6) 0.8663(3) 0.0368(8) Uani 1 d .
H7 H 0.2615 1.2693 0.8985 0.044 Uiso 1 calc R
C8 C 0.18433(15) 1.1237(6) 0.9059(2) 0.0366(9) Uani 1 d .
C9 C 0.04528(15) 1.2080(6) 0.8559(3) 0.0391(9) Uani 1 d .
C10 C -0.01114(19) 1.1478(9) 0.6433(3) 0.0583(12) Uani 1 d .
H10A H -0.0232 1.0253 0.6172 0.088 Uiso 1 calc R
H10B H -0.0207 1.2390 0.5932 0.088 Uiso 1 calc R
H10C H -0.0321 1.1782 0.6873 0.088 Uiso 1 calc R
O11 O -0.00069(12) 1.1134(5) 0.8472(2) 0.0597(10) Uani 1 d .
O12 O 0.06497(12) 1.3360(5) 0.91590(19) 0.0501(8) Uani 1 d .
O13 O 0.18061(11) 1.0543(6) 0.97836(18) 0.0482(7) Uani 1 d .
N14 N 0.27174(13) 1.0023(5) 0.8615(2) 0.0405(8) Uani 1 d .
H14 H 0.2552 0.8931 0.8543 0.049 Uiso 1 calc R
C15 C 0.32973(16) 1.0170(6) 0.8680(3) 0.0377(8) Uani 1 d .
O16 O 0.35640(14) 1.1665(5) 0.8795(3) 0.0659(10) Uani 1 d .
C17 C 0.36092(15) 0.8317(6) 0.8617(3) 0.0368(8) Uani 1 d .
H17 H 0.3516 0.7414 0.9047 0.044 Uiso 1 calc R
N18 N 0.42723(13) 0.8707(6) 0.8969(2) 0.0449(8) Uani 1 d .
H18A H 0.4468 0.7772 0.8798 0.067 Uiso 1 calc R
H18B H 0.4395 0.8801 0.9598 0.067 Uiso 1 calc R
H18C H 0.4347 0.9779 0.8720 0.067 Uiso 1 calc R
C19 C 0.34131(16) 0.7486(6) 0.7633(3) 0.0395(9) Uani 1 d .
C20 C 0.3408(2) 0.8717(8) 0.6828(3) 0.0548(11) Uani 1 d .
H20A H 0.3806 0.9246 0.6943 0.066 Uiso 1 calc R
H20B H 0.3131 0.9747 0.6789 0.066 Uiso 1 calc R
C21 C 0.3227(3) 0.7687(10) 0.5902(4) 0.0664(15) Uani 1 d .
H21 H 0.3223 0.8356 0.5363 0.080 Uiso 1 calc R
C22 C 0.3074(3) 0.5892(11) 0.5798(4) 0.0729(17) Uani 1 d .
H22 H 0.2966 0.5367 0.5195 0.088 Uiso 1 calc R
C23 C 0.3069(4) 0.4709(11) 0.6593(5) 0.0875(19) Uani 1 d .
H23A H 0.3336 0.3652 0.6630 0.105 Uiso 1 calc R
H23B H 0.2666 0.4215 0.6475 0.105 Uiso 1 calc R
C24 C 0.3255(2) 0.5706(8) 0.7522(3) 0.0572(11) Uani 1 d .
H24 H 0.3261 0.5026 0.8058 0.069 Uiso 1 calc R
C30 C 0.4930(3) 0.1450(8) 0.5427(4) 0.0717(15) Uani 1 d .
C31 C 0.4319(4) 0.1458(10) 0.5380(7) 0.102(3) Uani 1 d .
H31 H 0.4220 0.1449 0.5937 0.122 Uiso 1 calc R
C32 C 0.3872(4) 0.1478(12) 0.4529(11) 0.129(4) Uani 1 d .
H32 H 0.3472 0.1488 0.4508 0.154 Uiso 1 calc R
C33 C 0.4014(6) 0.1483(13) 0.3706(8) 0.131(4) Uani 1 d .
H33 H 0.3708 0.1518 0.3127 0.158 Uiso 1 calc R
C34 C 0.5406(5) 0.1438(11) 0.6277(5) 0.097(2) Uani 1 d .
H34 H 0.5322 0.1399 0.6847 0.117 Uiso 1 calc R
O40 O 0.21718(14) 0.6485(6) 0.8631(2) 0.0573(8) Uani 1 d .
O50 O 0.10781(18) 0.6832(8) 0.8930(3) 0.0818(12) Uani 1 d .
O60 O 0.4684(3) 0.2044(10) 0.8135(4) 0.1155(19) Uani 1 d .
O70 O 0.0000 0.835(11) 1.0000 0.48(5) 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_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S1 C2 94.67(18) . . y
C3 C2 S1 117.7(3) . . y
C4 C3 C2 124.2(3) . . y
C4 C3 C10 123.3(4) . . y
C2 C3 C10 112.3(3) . . y
C3 C4 N5 119.4(3) . . y
C3 C4 C9 125.8(3) . . y
N5 C4 C9 114.4(3) . . y
C8 N5 C4 134.2(3) . . y
C8 N5 C6 95.6(3) . . y
C4 N5 C6 126.1(3) . . y
N5 C6 C7 87.4(3) . . y
N5 C6 S1 110.3(3) . . y
C7 C6 S1 115.5(3) . . y
N14 C7 C8 114.4(3) . . y
N14 C7 C6 118.7(3) . . y
C8 C7 C6 84.5(2) . . y
O13 C8 N5 133.1(3) . . y
O13 C8 C7 134.7(3) . . y
N5 C8 C7 92.2(3) . . y
O11 C9 O12 125.2(3) . . y
O11 C9 C4 118.5(4) . . y
O12 C9 C4 116.2(3) . . y
C15 N14 C7 121.7(3) . . y
O16 C15 N14 122.9(4) . . y
O16 C15 C17 121.9(3) . . y
N14 C15 C17 115.2(3) . . y
N18 C17 C19 111.9(3) . . y
N18 C17 C15 106.4(3) . . y
C19 C17 C15 113.2(3) . . y
C24 C19 C20 122.6(4) . . y
C24 C19 C17 119.0(4) . . y
C20 C19 C17 118.4(4) . . y
C19 C20 C21 112.5(5) . . y
C22 C21 C20 124.5(5) . . y
C21 C22 C23 122.4(5) . . y
C22 C23 C24 113.8(6) . . y
C19 C24 C23 124.2(5) . . y
C34 C30 C30 118.0(9) . 2_656 y
C34 C30 C31 123.4(7) . . y
C30 C30 C31 118.6(8) 2_656 . y
C32 C31 C30 120.9(9) . . y
C31 C32 C33 119.8(10) . . y
C34 C33 C32 120.9(9) 2_656 . y
C33 C34 C30 121.7(9) 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 1.794(4) . y
S1 C2 1.817(4) . y
C2 C3 1.508(6) . y
C3 C4 1.328(5) . y
C3 C10 1.513(5) . y
C4 N5 1.418(4) . y
C4 C9 1.515(5) . y
N5 C8 1.352(5) . y
N5 C6 1.465(4) . y
C6 C7 1.561(5) . y
C7 N14 1.428(5) . y
C7 C8 1.545(5) . y
C8 O13 1.215(5) . y
C9 O11 1.243(5) . y
C9 O12 1.257(5) . y
N14 C15 1.337(4) . y
C15 O16 1.219(5) . y
C15 C17 1.525(6) . y
C17 N18 1.501(4) . y
C17 C19 1.511(6) . y
C19 C24 1.315(7) . y
C19 C20 1.482(6) . y
C20 C21 1.499(7) . y
C21 C22 1.323(10) . y
C22 C23 1.457(10) . y
C23 C24 1.491(8) . y
C30 C34 1.396(10) . y
C30 C30 1.410(12) 2_656 y
C30 C31 1.413(10) . y
C31 C32 1.363(14) . y
C32 C33 1.369(16) . y
C33 C34 1.352(15) 2_656 y
C34 C33 1.352(15) 2_656 y
