#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:07:09 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180375 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/44/7204436.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_7204436
loop_
_publ_author_name
'Brown, David'
'Brown, Giles A.'
'Andrews, Mark'
'Large, Jonathan M.'
'Urban, Dominique'
'Butts, Craig P.'
'Hales, Neil J.'
'Gallagher, Timothy'
_publ_section_title
;
 The azomethine ylide strategy for β-lactam synthesis. Azapenams and
 1-azacephams
;
_journal_issue                   17
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2014
_journal_page_last               2021
_journal_paper_doi               10.1039/b203890k
_journal_year                    2002
_chemical_formula_sum            'C30 H25 N3 O7 S'
_chemical_formula_weight         571.59
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 113.782(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   43.767(8)
_cell_length_b                   5.8471(10)
_cell_length_c                   22.777(5)
_cell_measurement_reflns_used    150
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      1.75
_cell_volume                     5333.9(19)
_computing_cell_refinement       'SMART (Siemens, 1995b)'
_computing_data_collection       'SMART (Siemens, 1995b)'
_computing_data_reduction        'SMART (Siemens, 1995b)'
_computing_molecular_graphics    'SHELXTL (Siemens, 1995a)'
_computing_publication_material  'SHELXTL (Siemens, 1995a)'
_computing_structure_refinement  'SHELXTL (Siemens, 1995a)'
_computing_structure_solution    'SHELXTL (Siemens, 1995a)'
_diffrn_ambient_temperature      173(2)
_diffrn_measurement_device       'Siemens SMART Area Detector'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0672
_diffrn_reflns_av_sigmaI/netI    0.0534
_diffrn_reflns_limit_h_max       56
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            26690
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.177
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    None
_exptl_crystal_description       Rectangular
_exptl_crystal_F_000             2384
_exptl_crystal_size_max          .65
_exptl_crystal_size_mid          .26
_exptl_crystal_size_min          .1
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.009
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         6143
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.009
_refine_ls_restrained_S_obs      1.115
_refine_ls_R_factor_all          0.1021
_refine_ls_R_factor_gt           0.0491
_refine_ls_shift/esd_mean        0.000
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1185
_refine_ls_wR_factor_ref         0.0992
_reflns_number_gt                3655
_reflns_number_total             6143
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b203890k.txt
_cod_data_source_block           rushjob
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_cell_volume        5333.9(18)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7204436
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
N1 N 0.06086(4) 0.1705(3) 0.13100(8) 0.0365(4) Uani 1 d . .
C2 C 0.06974(5) 0.2643(4) 0.19679(10) 0.0346(5) Uani 1 d . .
H2A H 0.06796(5) 0.4348(4) 0.19384(10) 0.042 Uiso 1 calc R .
C3 C 0.04133(5) 0.1706(4) 0.21577(10) 0.0382(5) Uani 1 d . .
H3A H 0.03372(5) 0.2942(4) 0.23710(10) 0.046 Uiso 1 calc R .
N4 N 0.01480(4) 0.1147(3) 0.15448(9) 0.0412(5) Uani 1 d . .
C5 C 0.02681(5) 0.0714(4) 0.10399(11) 0.0409(6) Uani 1 d . .
H5A H 0.02598(5) -0.0930(4) 0.09134(11) 0.049 Uiso 1 calc R .
C6 C -0.00255(6) 0.2174(5) 0.05758(12) 0.0559(7) Uani 1 d . .
H6A H 0.00429(6) 0.3492(5) 0.03838(12) 0.067 Uiso 1 calc R .
H6B H -0.02060(6) 0.1280(5) 0.02473(12) 0.067 Uiso 1 calc R .
C7 C -0.00874(6) 0.2747(5) 0.11655(14) 0.0564(7) Uani 1 d . .
O8 O -0.02551(5) 0.4051(4) 0.13112(10) 0.0825(7) Uani 1 d . .
S9 S 0.074608(14) 0.29938(11) 0.08227(3) 0.0420(2) Uani 1 d . .
O10 O 0.07283(4) 0.5427(3) 0.08796(8) 0.0529(5) Uani 1 d . .
O11 O 0.05717(4) 0.1934(3) 0.02086(7) 0.0565(5) Uani 1 d . .
C12 C 0.11705(5) 0.2231(4) 0.11170(10) 0.0361(5) Uani 1 d . .
C13 C 0.12618(6) 0.0119(4) 0.09628(10) 0.0402(6) Uani 1 d . .
H13A H 0.10975(6) -0.0895(4) 0.06848(10) 0.048 Uiso 1 calc R .
C14 C 0.15962(6) -0.0492(4) 0.12198(11) 0.0423(6) Uani 1 d . .
H14A H 0.16601(6) -0.1929(4) 0.11103(11) 0.051 Uiso 1 calc R .
C15 C 0.18404(6) 0.0956(4) 0.16352(11) 0.0419(6) Uani 1 d . .
C16 C 0.17411(6) 0.3072(4) 0.17763(11) 0.0415(6) Uani 1 d . .
H16A H 0.19048(6) 0.4086(4) 0.20561(11) 0.050 Uiso 1 calc R .
C17 C 0.14104(6) 0.3732(4) 0.15192(10) 0.0383(5) Uani 1 d . .
H17A H 0.13472(6) 0.5192(4) 0.16156(10) 0.046 Uiso 1 calc R .
C18 C 0.22021(6) 0.0237(5) 0.19304(13) 0.0607(8) Uani 1 d . .
H18A H 0.22245(6) -0.1293(5) 0.17766(13) 0.091 Uiso 1 calc R .
H18B H 0.22806(6) 0.0212(5) 0.23986(13) 0.091 Uiso 1 calc R .
H18C H 0.23362(6) 0.1326(5) 0.18075(13) 0.091 Uiso 1 calc R .
C19 C 0.10484(5) 0.2017(4) 0.24260(9) 0.0328(5) Uani 1 d . .
C20 C 0.12336(5) 0.3560(4) 0.28807(10) 0.0333(5) Uani 1 d . .
H20A H 0.11360(5) 0.4975(4) 0.29171(10) 0.040 Uiso 1 calc R .
C21 C 0.15721(5) 0.3082(4) 0.33032(9) 0.0321(5) Uani 1 d . .
C22 C 0.17683(6) 0.4663(4) 0.37694(10) 0.0387(5) Uani 1 d . .
H22A H 0.16728(6) 0.6067(4) 0.38213(10) 0.046 Uiso 1 calc R .
C23 C 0.20932(6) 0.4197(4) 0.41456(11) 0.0439(6) Uani 1 d . .
H23A H 0.22226(6) 0.5277(4) 0.44585(11) 0.053 Uiso 1 calc R .
C24 C 0.22401(6) 0.2124(4) 0.40760(11) 0.0440(6) Uani 1 d . .
H24A H 0.24681(6) 0.1829(4) 0.43390(11) 0.053 Uiso 1 calc R .
C25 C 0.20580(6) 0.0545(4) 0.36357(10) 0.0410(6) Uani 1 d . .
H25A H 0.21592(6) -0.0851(4) 0.35966(10) 0.049 Uiso 1 calc R .
C26 C 0.17144(5) 0.0971(4) 0.32296(10) 0.0334(5) Uani 1 d . .
C27 C 0.15151(5) -0.0617(4) 0.27631(10) 0.0364(5) Uani 1 d . .
H27A H 0.16075(5) -0.2044(4) 0.27193(10) 0.044 Uiso 1 calc R .
C28 C 0.11923(5) -0.0119(4) 0.23772(10) 0.0348(5) Uani 1 d . .
H28A H 0.10612(5) -0.1213(4) 0.20708(10) 0.042 Uiso 1 calc R .
C29 C 0.05088(6) -0.0401(5) 0.25828(12) 0.0423(6) Uani 1 d . .
O30 O 0.05160(5) -0.2304(3) 0.23943(9) 0.0627(5) Uani 1 d . .
O31 O 0.05765(4) 0.0171(3) 0.31877(8) 0.0535(5) Uani 1 d . .
C32 C 0.06239(6) -0.1704(5) 0.36370(13) 0.0626(8) Uani 1 d . .
H32A H 0.05410(6) -0.3138(5) 0.33933(13) 0.075 Uiso 1 calc R .
H32B H 0.04898(6) -0.1407(5) 0.38903(13) 0.075 Uiso 1 calc R .
C33 C 0.09818(6) -0.2010(4) 0.40848(11) 0.0409(6) Uani 1 d . .
C34 C 0.12280(6) -0.0388(4) 0.41758(11) 0.0428(6) Uani 1 d . .
H34A H 0.11732(6) 0.0983(4) 0.39315(11) 0.051 Uiso 1 calc R .
C35 C 0.15520(6) -0.0735(4) 0.46163(11) 0.0434(6) Uani 1 d . .
H35A H 0.17202(6) 0.0378(4) 0.46774(11) 0.052 Uiso 1 calc R .
C36 C 0.16246(6) -0.2742(4) 0.49651(10) 0.0394(5) Uani 1 d . .
C37 C 0.13859(6) -0.4400(4) 0.48846(11) 0.0412(6) Uani 1 d . .
H37A H 0.14422(6) -0.5771(4) 0.51292(11) 0.049 Uiso 1 calc R .
C38 C 0.10651(6) -0.4025(4) 0.44429(11) 0.0419(6) Uani 1 d . .
H38A H 0.08984(6) -0.5151(4) 0.43810(11) 0.050 Uiso 1 calc R .
N39 N 0.19673(5) -0.3167(4) 0.54286(10) 0.0525(6) Uani 1 d . .
O40 O 0.21800(5) -0.1724(4) 0.54843(10) 0.0742(6) Uani 1 d . .
O41 O 0.20265(4) -0.4940(4) 0.57417(9) 0.0664(6) 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 0.0033 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'
S S 0.1246 0.1234 '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
C5 N1 C2 111.8(2) . . ?
C5 N1 S9 118.67(14) . . ?
C2 N1 S9 119.42(14) . . ?
N1 C2 C19 112.6(2) . . ?
N1 C2 C3 103.5(2) . . ?
C19 C2 C3 115.0(2) . . ?
N4 C3 C29 109.8(2) . . ?
N4 C3 C2 103.3(2) . . ?
C29 C3 C2 114.5(2) . . ?
C7 N4 C3 123.2(2) . . ?
C7 N4 C5 92.2(2) . . ?
C3 N4 C5 113.2(2) . . ?
N4 C5 N1 103.0(2) . . ?
N4 C5 C6 88.8(2) . . ?
N1 C5 C6 119.1(2) . . ?
C7 C6 C5 85.0(2) . . ?
O8 C7 N4 129.5(3) . . ?
O8 C7 C6 137.6(3) . . ?
N4 C7 C6 92.8(2) . . ?
O10 S9 O11 119.30(11) . . ?
O10 S9 N1 110.25(10) . . ?
O11 S9 N1 105.34(10) . . ?
O10 S9 C12 107.73(10) . . ?
O11 S9 C12 109.06(11) . . ?
N1 S9 C12 104.14(10) . . ?
C13 C12 C17 120.7(2) . . ?
C13 C12 S9 119.8(2) . . ?
C17 C12 S9 119.4(2) . . ?
C14 C13 C12 119.1(2) . . ?
C13 C14 C15 121.4(2) . . ?
C16 C15 C14 118.2(2) . . ?
C16 C15 C18 120.9(2) . . ?
C14 C15 C18 120.9(2) . . ?
C17 C16 C15 121.5(2) . . ?
C16 C17 C12 119.2(2) . . ?
C20 C19 C28 119.5(2) . . ?
C20 C19 C2 119.3(2) . . ?
C28 C19 C2 121.1(2) . . ?
C19 C20 C21 121.2(2) . . ?
C22 C21 C26 119.7(2) . . ?
C22 C21 C20 122.0(2) . . ?
C26 C21 C20 118.3(2) . . ?
C23 C22 C21 120.5(2) . . ?
C22 C23 C24 120.7(2) . . ?
C25 C24 C23 120.5(2) . . ?
C24 C25 C26 120.5(2) . . ?
C27 C26 C21 119.4(2) . . ?
C27 C26 C25 122.6(2) . . ?
C21 C26 C25 118.0(2) . . ?
C28 C27 C26 120.6(2) . . ?
C27 C28 C19 121.0(2) . . ?
O30 C29 O31 125.3(2) . . ?
O30 C29 C3 124.5(2) . . ?
O31 C29 C3 110.2(2) . . ?
C29 O31 C32 116.6(2) . . ?
O31 C32 C33 112.5(2) . . ?
C34 C33 C38 119.1(2) . . ?
C34 C33 C32 123.9(2) . . ?
C38 C33 C32 117.0(2) . . ?
C35 C34 C33 121.1(2) . . ?
C36 C35 C34 118.2(2) . . ?
C35 C36 C37 122.3(2) . . ?
C35 C36 N39 119.3(2) . . ?
C37 C36 N39 118.4(2) . . ?
C38 C37 C36 118.6(2) . . ?
C37 C38 C33 120.8(2) . . ?
O40 N39 O41 123.3(2) . . ?
O40 N39 C36 118.2(2) . . ?
O41 N39 C36 118.5(2) . . ?
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
N1 C5 1.481(3) . ?
N1 C2 1.493(3) . ?
N1 S9 1.643(2) . ?
C2 C19 1.513(3) . ?
C2 C3 1.571(3) . ?
C3 N4 1.448(3) . ?
C3 C29 1.518(3) . ?
N4 C7 1.402(3) . ?
N4 C5 1.466(3) . ?
C5 C6 1.550(3) . ?
C6 C7 1.511(4) . ?
C7 O8 1.195(3) . ?
S9 O10 1.434(2) . ?
S9 O11 1.436(2) . ?
S9 C12 1.759(2) . ?
C12 C13 1.386(3) . ?
C12 C17 1.391(3) . ?
C13 C14 1.386(3) . ?
C14 C15 1.393(3) . ?
C15 C16 1.391(3) . ?
C15 C18 1.509(3) . ?
C16 C17 1.380(3) . ?
C19 C20 1.366(3) . ?
C19 C28 1.423(3) . ?
C20 C21 1.431(3) . ?
C21 C22 1.409(3) . ?
C21 C26 1.422(3) . ?
C22 C23 1.359(3) . ?
C23 C24 1.410(3) . ?
C24 C25 1.360(3) . ?
C25 C26 1.434(3) . ?
C26 C27 1.416(3) . ?
C27 C28 1.361(3) . ?
C29 O30 1.197(3) . ?
C29 O31 1.330(3) . ?
O31 C32 1.456(3) . ?
C32 C33 1.496(3) . ?
C33 C34 1.387(3) . ?
C33 C38 1.395(3) . ?
C34 C35 1.382(3) . ?
C35 C36 1.380(3) . ?
C36 C37 1.382(3) . ?
C36 N39 1.466(3) . ?
C37 C38 1.376(3) . ?
N39 O40 1.224(3) . ?
N39 O41 1.226(3) . ?
