#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/49/1504997.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_1504997
loop_
_publ_author_name
'Norris, Timothy'
'VanAlsten, John'
'Hubbs, Stephen'
'Ewing, Marcus'
'Cai, Weiling'
'Jorgensen, Matthew L.'
'Bordner, Jon'
'Jensen, Grace O.'
_publ_section_title
;
 Commercialization and Late-Stage Development of a Semisynthetic
 Antifungal API: Anidulafungin/d-Fructose (Eraxis)
;
_journal_issue                   3
_journal_name_full               'Organic Process Research & Development'
_journal_page_first              447
_journal_paper_doi               10.1021/op800055h
_journal_volume                  12
_journal_year                    2008
_chemical_formula_sum            'C30 H27 N3 O3'
_chemical_formula_weight         477.55
_chemical_name_systematic
; 
 ? 
;
_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-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.3790(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   52.7951(12)
_cell_length_b                   7.8456(2)
_cell_length_c                   12.2836(2)
_cell_measurement_reflns_used    4789
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      58.74
_cell_measurement_theta_min      5.70
_cell_volume                     5019.96(19)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.911
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Montel multilayer optics'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -56
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9738
_diffrn_reflns_theta_full        58.94
_diffrn_reflns_theta_max         58.94
_diffrn_reflns_theta_min         5.70
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            translucent
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             2016
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       0.00040(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0688
_refine_ls_shift/su_max          0.259
_refine_ls_shift/su_mean         0.014
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1342P)²+4.4201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1955
_refine_ls_wR_factor_ref         0.2172
_reflns_number_gt                2434
_reflns_number_total             3286
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            op800055h-file001.cif
_cod_data_source_block           i649
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               1504997
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.06266(5) 0.9008(3) 0.48285(18) 0.0670(7) Uani 1 1 d .
N2 N 0.06494(6) 0.8066(4) 0.5740(2) 0.0796(8) Uani 1 1 d .
N3 N 0.04950(6) 0.8711(4) 0.6357(2) 0.0830(9) Uani 1 1 d .
C4 C 0.03721(6) 1.0093(5) 0.5817(2) 0.0682(9) Uani 1 1 d .
C5 C 0.04564(6) 1.0303(4) 0.4812(2) 0.0588(8) Uani 1 1 d .
C6 C 0.03679(6) 1.1579(4) 0.4061(3) 0.0716(9) Uani 1 1 d .
H6A H 0.0426 1.1694 0.3390 0.080 Uiso 1 1 calc R
C7 C 0.01890(8) 1.2654(5) 0.4375(3) 0.0894(11) Uani 1 1 d .
H7A H 0.0123 1.3531 0.3903 0.080 Uiso 1 1 calc R
C8 C 0.01024(7) 1.2469(5) 0.5391(4) 0.0963(12) Uani 1 1 d .
H8A H -0.0019 1.3233 0.5575 0.080 Uiso 1 1 calc R
C9 C 0.01897(7) 1.1216(6) 0.6108(3) 0.0905(12) Uani 1 1 d .
H9A H 0.0130 1.1105 0.6776 0.080 Uiso 1 1 calc R
O10 O 0.07792(4) 0.8711(3) 0.40512(16) 0.0718(6) Uani 1 1 d .
C11 C 0.06767(6) 0.7462(4) 0.3268(2) 0.0612(8) Uani 1 1 d .
O12 O 0.04962(5) 0.6640(3) 0.33878(17) 0.0795(7) Uani 1 1 d .
C13 C 0.08268(5) 0.7437(3) 0.2360(2) 0.0543(7) Uani 1 1 d .
C14 C 0.07563(5) 0.6266(4) 0.1517(2) 0.0573(7) Uani 1 1 d .
H14A H 0.0627 0.5476 0.1569 0.080 Uiso 1 1 calc R
C15 C 0.08774(5) 0.6274(4) 0.0602(2) 0.0571(7) Uani 1 1 d .
H15A H 0.0828 0.5489 0.0040 0.080 Uiso 1 1 calc R
C16 C 0.10729(6) 0.7443(4) 0.0505(2) 0.0558(7) Uani 1 1 d .
C17 C 0.11423(6) 0.8579(4) 0.1375(2) 0.0684(9) Uani 1 1 d .
H17A H 0.1273 0.9359 0.1337 0.080 Uiso 1 1 calc R
C18 C 0.10225(6) 0.8575(4) 0.2285(2) 0.0668(8) Uani 1 1 d .
H18A H 0.1073 0.9343 0.2855 0.080 Uiso 1 1 calc R
C19 C 0.11999(5) 0.7483(3) -0.0483(2) 0.0548(7) Uani 1 1 d .
C20 C 0.10765(6) 0.6926(4) -0.1505(2) 0.0656(8) Uani 1 1 d .
H20A H 0.0909 0.6520 -0.1570 0.080 Uiso 1 1 calc R
C21 C 0.11937(6) 0.6957(4) -0.2424(2) 0.0655(8) Uani 1 1 d .
H21A H 0.1103 0.6578 -0.3093 0.080 Uiso 1 1 calc R
C22 C 0.14445(5) 0.7538(3) -0.2383(2) 0.0554(7) Uani 1 1 d .
C23 C 0.15663(6) 0.8108(5) -0.1360(2) 0.0753(9) Uani 1 1 d .
H23A H 0.1733 0.8517 -0.1293 0.080 Uiso 1 1 calc R
C24 C 0.14472(6) 0.8086(5) -0.0444(3) 0.0753(9) Uani 1 1 d .
H24A H 0.1536 0.8489 0.0223 0.080 Uiso 1 1 calc R
C25 C 0.15683(6) 0.7559(4) -0.3386(2) 0.0575(8) Uani 1 1 d .
C26 C 0.14615(7) 0.6715(5) -0.4342(3) 0.0839(11) Uani 1 1 d .
H26A H 0.1308 0.6127 -0.4347 0.080 Uiso 1 1 calc R
C27 C 0.15717(7) 0.6706(5) -0.5285(3) 0.0853(11) Uani 1 1 d .
H27A H 0.1493 0.6117 -0.5907 0.080 Uiso 1 1 calc R
C28 C 0.17959(6) 0.7562(4) -0.5307(3) 0.0674(8) Uani 1 1 d .
C29 C 0.19069(6) 0.8422(5) -0.4369(3) 0.0756(9) Uani 1 1 d .
H29A H 0.2060 0.9009 -0.4370 0.080 Uiso 1 1 calc R
C30 C 0.17952(6) 0.8425(4) -0.3437(3) 0.0714(9) Uani 1 1 d .
H30A H 0.1874 0.9025 -0.2820 0.080 Uiso 1 1 calc R
O31 O 0.19226(5) 0.7631(3) -0.61949(18) 0.0840(7) Uani 1 1 d .
C32 C 0.18236(8) 0.6631(6) -0.7150(3) 0.0973(12) Uani 1 1 d .
H32A H 0.1657 0.7062 -0.7483 0.080 Uiso 1 1 calc R
H32B H 0.1803 0.5455 -0.6935 0.080 Uiso 1 1 calc R
C33 C 0.20059(9) 0.6726(6) -0.7963(3) 0.1056(14) Uani 1 1 d .
H33A H 0.1924 0.6214 -0.8650 0.080 Uiso 1 1 calc R
H33B H 0.2036 0.7917 -0.8111 0.080 Uiso 1 1 calc R
C34 C 0.22540(10) 0.5897(7) -0.7626(5) 0.1349(18) Uani 1 1 d .
H34A H 0.2224 0.4699 -0.7499 0.080 Uiso 1 1 calc R
H34B H 0.2333 0.6385 -0.6927 0.080 Uiso 1 1 calc R
C35 C 0.24390(13) 0.6027(9) -0.8414(6) 0.203(3) Uani 1 1 d .
H35A H 0.2434 0.7215 -0.8634 0.080 Uiso 1 1 calc R
H35B H 0.2606 0.5855 -0.7968 0.080 Uiso 1 1 calc R
C36 C 0.24463(17) 0.5274(10) -0.9216(6) 0.271(5) Uani 1 1 d .
H36A H 0.2599 0.5571 -0.9500 0.080 Uiso 1 1 calc R
H36B H 0.2299 0.5550 -0.9752 0.080 Uiso 1 1 calc R
H36C H 0.2447 0.4074 -0.9062 0.080 Uiso 1 1 calc R
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N2 N1 C5 113.5(2)
N2 N1 O10 120.7(3)
C5 N1 O10 125.7(2)
N3 N2 N1 107.1(3)
N2 N3 C4 108.4(3)
N3 C4 C5 109.1(3)
N3 C4 C9 131.7(3)
C5 C4 C9 119.1(3)
N1 C5 C4 101.8(3)
N1 C5 C6 134.5(3)
C4 C5 C6 123.7(3)
C7 C6 C5 115.4(3)
C6 C7 C8 121.8(4)
C9 C8 C7 121.9(4)
C8 C9 C4 118.1(3)
N1 O10 C11 112.9(2)
O12 C11 O10 121.4(3)
O12 C11 C13 129.3(3)
O10 C11 C13 109.3(3)
C18 C13 C14 119.4(3)
C18 C13 C11 123.0(3)
C14 C13 C11 117.5(3)
C15 C14 C13 120.0(3)
C14 C15 C16 121.2(3)
C17 C16 C15 117.3(3)
C17 C16 C19 121.2(3)
C15 C16 C19 121.5(2)
C18 C17 C16 121.7(3)
C17 C18 C13 120.4(3)
C24 C19 C20 116.2(3)
C24 C19 C16 122.0(3)
C20 C19 C16 121.8(3)
C21 C20 C19 122.0(3)
C20 C21 C22 121.9(3)
C23 C22 C21 115.8(3)
C23 C22 C25 123.0(3)
C21 C22 C25 121.1(3)
C24 C23 C22 122.0(3)
C23 C24 C19 122.0(3)
C26 C25 C30 115.5(3)
C26 C25 C22 121.6(3)
C30 C25 C22 122.8(3)
C27 C26 C25 123.0(3)
C28 C27 C26 120.0(3)
C27 C28 O31 124.9(3)
C27 C28 C29 118.4(3)
O31 C28 C29 116.7(3)
C30 C29 C28 121.1(3)
C29 C30 C25 121.9(3)
C28 O31 C32 117.9(3)
O31 C32 C33 109.3(3)
C34 C33 C32 115.6(4)
C33 C34 C35 116.0(5)
C36 C35 C34 129.6(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 N2 1.330(3)
N1 C5 1.354(4)
N1 O10 1.366(3)
N2 N3 1.303(4)
N3 C4 1.377(4)
C4 C5 1.389(4)
C4 C9 1.394(5)
C5 C6 1.390(4)
C6 C7 1.368(5)
C7 C8 1.405(6)
C8 C9 1.350(5)
O10 C11 1.417(3)
C11 O12 1.180(4)
C11 C13 1.470(4)
C13 C18 1.379(4)
C13 C14 1.389(4)
C14 C15 1.381(4)
C15 C16 1.400(4)
C16 C17 1.393(4)
C16 C19 1.480(4)
C17 C18 1.372(4)
C19 C24 1.382(4)
C19 C20 1.387(4)
C20 C21 1.373(4)
C21 C22 1.394(4)
C22 C23 1.388(4)
C22 C25 1.486(4)
C23 C24 1.376(4)
C25 C26 1.385(4)
C25 C30 1.388(4)
C26 C27 1.379(5)
C27 C28 1.365(5)
C28 O31 1.370(4)
C28 C29 1.381(4)
C29 C30 1.371(4)
O31 C32 1.437(4)
C32 C33 1.498(5)
C33 C34 1.461(6)
C34 C35 1.486(7)
C35 C36 1.155(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9342571
