#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:22:13 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178896 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/25/4112551.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_4112551
loop_
_publ_author_name
'Stephen Hanessian'
'Martin Tremblay'
'Jens F. W. Petersen'
_publ_contact_author_address
;
      Université de Montréal
      Département de Chimie
      C.P. 6128, Succ. Centre-ville
      Montréal, Québec
      Canada, H3C 3J7
;
_publ_contact_author_email       stephen.hanessian@umontreal.ca
_publ_contact_author_fax         '+1 514 343 5728'
_publ_contact_author_name        'Dr Stephen Hanessian'
_publ_contact_author_phone       '+1 514 343 6738'
_publ_section_title
;
 The N-Acyloxyiminium Ion Aza-Prins Route to Octahydroindoles: Total
 Synthesis and Structural Confirmation of the Antithrombotic Marine
 Natural Product Oscillarin
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6064
_journal_page_last               6071
_journal_paper_doi               10.1021/ja030669g
_journal_volume                  126
_journal_year                    2004
_chemical_absolute_configuration rmad
_chemical_compound_source        'Synthesized by the authors. See text'
_chemical_formula_moiety         'C18 H30 Cl N O4'
_chemical_formula_sum            'C18 H30 Cl N O4'
_chemical_formula_weight         359.88
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.335(3)
_cell_length_b                   9.404(2)
_cell_length_c                   34.399(9)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      20.00
_cell_volume                     2049.3(12)
_computing_cell_refinement       'CAD4 Program (Nonius 1989)'
_computing_data_collection       'Local Program'
_computing_data_reduction        'Local Program'
_computing_molecular_graphics    'XP (Bruker, 1999)'
_computing_publication_material  'UdMX (local program)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 0.0
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Sealed Tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_av_sigmaI/netI    0.0630
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            3830
_diffrn_reflns_theta_full        69.98
_diffrn_reflns_theta_max         69.98
_diffrn_reflns_theta_min         2.57
_diffrn_standards_decay_%        0.04
_diffrn_standards_interval_time  60
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    1.809
_exptl_absorpt_correction_T_max  0.7700
_exptl_absorpt_correction_T_min  0.5700
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'gaussian from crystal shape'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.166
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.91
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), 1551 Friedel pairs'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       0.0023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.725
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.725
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0522P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1102
_reflns_number_gt                1780
_reflns_number_total             3830
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja030669g_3.cif
_cod_data_source_block           han338
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4112551
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, 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
Cl Cl 0.30597(17) 0.52219(13) 0.74775(3) 0.1253(4) Uani 1 1 d .
O10 O 0.2337(4) 0.1168(2) 0.91616(6) 0.0979(8) Uani 1 1 d .
O11 O 0.2763(4) 0.0630(2) 0.85212(6) 0.0831(6) Uani 1 1 d .
O15 O 0.1308(3) 0.4512(3) 0.90782(6) 0.0866(7) Uani 1 1 d .
O16 O 0.3162(3) 0.4382(2) 0.96375(5) 0.0755(6) Uani 1 1 d .
N N 0.4298(4) 0.2548(3) 0.87670(7) 0.0759(8) Uani 1 1 d .
C2 C 0.5312(5) 0.2897(3) 0.83992(9) 0.0713(9) Uani 1 1 d .
H2 H 0.5865 0.2034 0.8276 0.086 Uiso 1 1 calc R
C3 C 0.3751(5) 0.3654(3) 0.81234(8) 0.0740(9) Uani 1 1 d .
H3A H 0.2782 0.2962 0.8014 0.089 Uiso 1 1 calc R
H3B H 0.2932 0.4345 0.8269 0.089 Uiso 1 1 calc R
C4 C 0.4933(5) 0.4399(4) 0.77972(9) 0.0848(10) Uani 1 1 d .
H4 H 0.5729 0.3686 0.7650 0.102 Uiso 1 1 calc R
C5 C 0.6449(6) 0.5481(4) 0.79519(10) 0.0935(11) Uani 1 1 d .
H5A H 0.5692 0.6187 0.8103 0.112 Uiso 1 1 calc R
H5B H 0.7146 0.5961 0.7738 0.112 Uiso 1 1 calc R
C6 C 0.8076(5) 0.4748(4) 0.82054(10) 0.0959(11) Uani 1 1 d .
H6A H 0.8988 0.5463 0.8319 0.115 Uiso 1 1 calc R
H6B H 0.8944 0.4140 0.8043 0.115 Uiso 1 1 calc R
C7 C 0.7127(5) 0.3854(3) 0.85307(9) 0.0801(9) Uani 1 1 d .
H7 H 0.8245 0.3243 0.8635 0.096 Uiso 1 1 calc R
C8 C 0.6144(5) 0.4663(4) 0.88687(9) 0.0843(10) Uani 1 1 d .
H8A H 0.5273 0.5441 0.8776 0.101 Uiso 1 1 calc R
H8B H 0.7224 0.5040 0.9040 0.101 Uiso 1 1 calc R
C9 C 0.4805(5) 0.3539(4) 0.90765(9) 0.0740(9) Uani 1 1 d .
H9 H 0.5655 0.3061 0.9275 0.089 Uiso 1 1 calc R
C10 C 0.3036(6) 0.1418(4) 0.88441(10) 0.0806(9) Uani 1 1 d .
C11 C 0.1607(6) -0.0691(4) 0.85343(9) 0.0811(9) Uani 1 1 d .
C12 C 0.2619(7) -0.1705(4) 0.88177(11) 0.1218(15) Uani 1 1 d .
H12A H 0.2465 -0.1343 0.9077 0.183 Uiso 1 1 calc R
H12B H 0.4092 -0.1801 0.8757 0.183 Uiso 1 1 calc R
H12C H 0.1946 -0.2617 0.8799 0.183 Uiso 1 1 calc R
C13 C -0.0692(5) -0.0406(5) 0.86346(11) 0.1206(14) Uani 1 1 d .
H13A H -0.1251 0.0297 0.8461 0.181 Uiso 1 1 calc R
H13B H -0.0788 -0.0066 0.8897 0.181 Uiso 1 1 calc R
H13C H -0.1487 -0.1270 0.8609 0.181 Uiso 1 1 calc R
C14 C 0.1826(7) -0.1242(4) 0.81223(9) 0.1060(13) Uani 1 1 d .
H14A H 0.3295 -0.1337 0.8059 0.159 Uiso 1 1 calc R
H14B H 0.1174 -0.0586 0.7946 0.159 Uiso 1 1 calc R
H14C H 0.1149 -0.2152 0.8102 0.159 Uiso 1 1 calc R
C15 C 0.2869(6) 0.4174(3) 0.92592(9) 0.0737(9) Uani 1 1 d .
C16 C 0.1445(6) 0.4927(4) 0.98924(8) 0.0783(9) Uani 1 1 d .
C17 C 0.0839(7) 0.6394(4) 0.97580(11) 0.1132(14) Uani 1 1 d .
H17A H -0.0054 0.6832 0.9949 0.170 Uiso 1 1 calc R
H17B H 0.0094 0.6328 0.9516 0.170 Uiso 1 1 calc R
H17C H 0.2089 0.6957 0.9724 0.170 Uiso 1 1 calc R
C18 C 0.2567(6) 0.4979(4) 1.02862(8) 0.0997(11) Uani 1 1 d .
H18A H 0.3006 0.4038 1.0358 0.150 Uiso 1 1 calc R
H18B H 0.1618 0.5344 1.0479 0.150 Uiso 1 1 calc R
H18C H 0.3780 0.5587 1.0268 0.150 Uiso 1 1 calc R
C19 C -0.0314(6) 0.3897(4) 0.98933(10) 0.1080(14) Uani 1 1 d .
H19A H 0.0217 0.2967 0.9954 0.162 Uiso 1 1 calc R
H19B H -0.0968 0.3883 0.9642 0.162 Uiso 1 1 calc R
H19C H -0.1335 0.4173 1.0085 0.162 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'
Cl Cl 0.3639 0.7018 '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_publ_flag
C10 O11 C11 120.9(3) y
C15 O16 C16 121.7(3) y
C10 N C9 119.4(3) y
C10 N C2 127.3(3) y
C9 N C2 113.2(3) y
N C2 C7 102.0(2) y
N C2 C3 110.8(3) y
C7 C2 C3 113.1(3) y
N C2 H2 110.2 ?
C7 C2 H2 110.2 ?
C3 C2 H2 110.2 ?
C4 C3 C2 110.5(2) y
C4 C3 H3A 109.5 ?
C2 C3 H3A 109.5 ?
C4 C3 H3B 109.5 ?
C2 C3 H3B 109.5 ?
H3A C3 H3B 108.1 ?
C5 C4 C3 111.5(3) y
C5 C4 CL 110.5(3) y
C3 C4 CL 109.0(2) y
C5 C4 H4 108.6 ?
C3 C4 H4 108.6 ?
CL C4 H4 108.6 ?
C4 C5 C6 109.4(3) y
C4 C5 H5A 109.8 ?
C6 C5 H5A 109.8 ?
C4 C5 H5B 109.8 ?
C6 C5 H5B 109.8 ?
H5A C5 H5B 108.2 ?
C5 C6 C7 113.9(3) y
C5 C6 H6A 108.8 ?
C7 C6 H6A 108.8 ?
C5 C6 H6B 108.8 ?
C7 C6 H6B 108.8 ?
H6A C6 H6B 107.7 ?
C8 C7 C6 116.5(3) y
C8 C7 C2 102.3(3) y
C6 C7 C2 113.8(3) y
C8 C7 H7 107.9 ?
C6 C7 H7 107.9 ?
C2 C7 H7 107.9 ?
C7 C8 C9 103.7(3) y
C7 C8 H8A 111 ?
C9 C8 H8A 111 ?
C7 C8 H8B 111 ?
C9 C8 H8B 111 ?
H8A C8 H8B 109 ?
N C9 C15 112.4(3) y
N C9 C8 102.9(3) y
C15 C9 C8 111.9(3) y
N C9 H9 109.8 ?
C15 C9 H9 109.8 ?
C8 C9 H9 109.8 ?
O10 C10 O11 126.5(3) y
O10 C10 N 123.2(3) y
O11 C10 N 110.2(3) y
O11 C11 C12 110.4(3) y
O11 C11 C14 102.6(3) y
C12 C11 C14 110.5(3) y
O11 C11 C13 110.0(3) y
C12 C11 C13 111.9(3) y
C14 C11 C13 111.1(3) y
C11 C12 H12A 109.5 ?
C11 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C11 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 109.5 ?
C11 C13 H13A 109.5 ?
C11 C13 H13B 109.5 ?
H13A C13 H13B 109.5 ?
C11 C13 H13C 109.5 ?
H13A C13 H13C 109.5 ?
H13B C13 H13C 109.5 ?
C11 C14 H14A 109.5 ?
C11 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C11 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
O15 C15 O16 125.4(3) y
O15 C15 C9 123.8(3) y
O16 C15 C9 110.7(3) y
C19 C16 O16 109.1(3) y
C19 C16 C17 114.2(3) y
O16 C16 C17 108.7(3) y
C19 C16 C18 111.7(3) y
O16 C16 C18 101.1(3) y
C17 C16 C18 111.2(3) y
C16 C17 H17A 109.5 ?
C16 C17 H17B 109.5 ?
H17A C17 H17B 109.5 ?
C16 C17 H17C 109.5 ?
H17A C17 H17C 109.5 ?
H17B C17 H17C 109.5 ?
C16 C18 H18A 109.5 ?
C16 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C16 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C16 C19 H19A 109.5 ?
C16 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C16 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cl C4 1.793(3) y
O10 C10 1.201(4) y
O11 C10 1.346(4) y
O11 C11 1.443(4) y
O15 C15 1.211(3) y
O16 C15 1.329(3) y
O16 C16 1.488(4) y
N C10 1.356(4) y
N C9 1.451(4) y
N C2 1.457(4) y
C2 C7 1.528(4) y
C2 C3 1.544(4) y
C2 H2 0.98 ?
C3 C4 1.521(4) y
C3 H3a 0.97 ?
C3 H3b 0.97 ?
C4 C5 1.496(4) y
C4 H4 0.98 ?
C5 C6 1.516(4) y
C5 H5a 0.97 ?
C5 H5b 0.97 ?
C6 C7 1.523(4) y
C6 H6a 0.97 ?
C6 H6b 0.97 ?
C7 C8 1.523(4) y
C7 H7 0.98 ?
C8 C9 1.532(4) y
C8 H8a 0.97 ?
C8 H8b 0.97 ?
C9 C15 1.502(4) y
C9 H9 0.98 ?
C11 C12 1.507(4) y
C11 C14 1.515(4) y
C11 C13 1.520(5) y
C12 H12a 0.96 ?
C12 H12b 0.96 ?
C12 H12c 0.96 ?
C13 H13a 0.96 ?
C13 H13b 0.96 ?
C13 H13c 0.96 ?
C14 H14a 0.96 ?
C14 H14b 0.96 ?
C14 H14c 0.96 ?
C16 C19 1.476(4) y
C16 C17 1.504(5) y
C16 C18 1.531(4) y
C17 H17a 0.96 ?
C17 H17b 0.96 ?
C17 H17c 0.96 ?
C18 H18a 0.96 ?
C18 H18b 0.96 ?
C18 H18c 0.96 ?
C19 H19a 0.96 ?
C19 H19b 0.96 ?
C19 H19c 0.96 ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C10 N C2 C7 -158.0(3) y
C9 N C2 C7 20.2(3) y
C10 N C2 C3 81.3(4) y
C9 N C2 C3 -100.5(3) y
N C2 C3 C4 163.2(3) y
C7 C2 C3 C4 49.3(4) y
C2 C3 C4 C5 -59.3(4) y
C2 C3 C4 CL 178.5(2) y
C3 C4 C5 C6 61.3(4) y
CL C4 C5 C6 -177.3(2) y
C4 C5 C6 C7 -54.4(4) y
C5 C6 C7 C8 -72.4(4) y
C5 C6 C7 C2 46.2(4) y
N C2 C7 C8 -35.9(3) y
C3 C2 C7 C8 83.2(3) y
N C2 C7 C6 -162.4(3) y
C3 C2 C7 C6 -43.3(4) y
C6 C7 C8 C9 164.1(3) y
C2 C7 C8 C9 39.3(3) y
C10 N C9 C15 -57.0(4) y
C2 N C9 C15 124.7(3) y
C10 N C9 C8 -177.6(3) y
C2 N C9 C8 4.1(3) y
C7 C8 C9 N -27.0(3) y
C7 C8 C9 C15 -147.9(3) y
C11 O11 C10 O10 -2.6(5) y
C11 O11 C10 N 175.4(3) y
C9 N C10 O10 -1.7(5) y
C2 N C10 O10 176.4(3) y
C9 N C10 O11 -179.8(3) y
C2 N C10 O11 -1.7(5) y
C10 O11 C11 C12 -58.6(4) y
C10 O11 C11 C14 -176.4(3) y
C10 O11 C11 C13 65.3(4) y
C16 O16 C15 O15 7.0(5) y
C16 O16 C15 C9 -176.6(3) y
N C9 C15 O15 -38.5(5) y
C8 C9 C15 O15 76.8(4) y
N C9 C15 O16 145.1(3) y
C8 C9 C15 O16 -99.7(3) y
C15 O16 C16 C19 62.4(4) y
C15 O16 C16 C17 -62.7(4) y
C15 O16 C16 C18 -179.7(3) y
