#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/49/4114962.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_4114962
loop_
_publ_author_name
'John M. Humphrey'
'Yusheng Liao'
'Amjad Ali'
'Tobias Rein'
'Yue-Ling Wong'
'Hui-Ju Chen'
'Anne K. Courtney'
'Stephen F. Martin'
_publ_section_title
;
 Enantioselective Total Syntheses of Manzamine A and Related Alkaloids
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8584
_journal_page_last               8592
_journal_paper_doi               10.1021/ja0202964
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C21 H31.6 I N2 O1.3'
_chemical_formula_weight         459.8
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   9.908(4)
_cell_length_b                   10.763(4)
_cell_length_c                   38.02(2)
_cell_measurement_reflns_used    32
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      9.3
_cell_measurement_theta_min      7
_cell_volume                     4054(3)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      183(2)
_diffrn_measurement_device_type  'Siemens P3'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            8840
_diffrn_reflns_theta_max         26.25
_diffrn_reflns_theta_min         2
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 96
_diffrn_standards_number         4
_exptl_absorpt_coefficient_mu    1.59
_exptl_absorpt_correction_T_max  .85
_exptl_absorpt_correction_T_min  .80
_exptl_absorpt_correction_type   gaussian
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.51
_exptl_crystal_description       needle
_exptl_crystal_F_000             1880
_exptl_crystal_size_max          .52
_exptl_crystal_size_mid          .13
_exptl_crystal_size_min          .13
_refine_diff_density_max         0.63
_refine_diff_density_min         -0.53
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.428
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         3575
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0486
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'calc w=1/[σ²(Fo)+(0.0004(Fo²))]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0513
_reflns_number_gt                2598
_reflns_number_total             4119
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0202964_3.cif
_cod_data_source_block           Compound36
_cod_original_formula_sum        'C21 H31.6 N2 O1.3 I'
_cod_database_code               4114962
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
1/2-X,-Y,1/2+Z
1/2+X,1/2-Y,-Z
-X,1/2+Y,1/2-Z
'-x, -y, -z'
'1/2+X, Y,1/2-Z'
'1/2-X,1/2+Y, 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_occupancy
I I 0.96336(4) 0.31415(5) 0.441030(10) 0.0502(2) 1
C1 C 0.7830(6) 0.2591(6) 0.6386(2) 0.027(2) 1
N2 N 0.7628(5) 0.3655(5) 0.66161(12) 0.029(2) 1
C3 C 0.8952(7) 0.4056(7) 0.6756(2) 0.033(2) 1
C4 C 0.9841(6) 0.4458(6) 0.6454(2) 0.029(2) 1
C4A C 1.0118(6) 0.3414(5) 0.6188(2) 0.025(2) 1
C5 C 1.1117(6) 0.2422(6) 0.63160(14) 0.026(2) 1
C6 C 1.0970(7) 0.1233(6) 0.6234(2) 0.031(2) 1
C7 C 0.9786(7) 0.0679(6) 0.6048(2) 0.034(2) 1
C7A C 0.8876(6) 0.1623(5) 0.58738(14) 0.025(2) 1
N8 N 0.9254(5) 0.1967(5) 0.54905(11) 0.0277(15) 1
C9 C 0.8727(8) 0.3289(7) 0.5446(2) 0.043(2) 1
C10 C 0.8093(7) 0.3683(7) 0.5790(2) 0.029(2) 1
C10A C 0.8745(5) 0.2853(5) 0.60686(14) 0.023(2) 1
C11 C 0.6702(7) 0.3261(7) 0.6905(2) 0.034(2) 1
C12 C 0.6390(6) 0.4270(6) 0.7162(2) 0.031(2) 1
C13 C 0.5414(7) 0.5156(7) 0.7084(2) 0.039(2) 1
C14 C 0.5124(8) 0.6102(7) 0.7318(2) 0.049(3) 1
C15 C 0.5792(7) 0.6179(7) 0.7631(2) 0.044(2) 1
C16 C 0.6762(7) 0.5309(7) 0.7719(2) 0.043(2) 1
C17 C 0.7035(7) 0.4357(6) 0.7485(2) 0.040(2) 1
C18 C 1.2359(6) 0.2895(7) 0.6492(2) 0.046(3) 1
C20 C 1.0738(6) 0.1961(9) 0.5415(2) 0.042(3) 1
C21 C 0.8579(8) 0.1093(8) 0.5244(2) 0.041(2) 1
O19 O 1.3427(6) 0.2135(7) 0.6505(2) 0.047(2) .69
O19A O 1.321(2) 0.3422(13) 0.6291(4) 0.043(4) .31
O1A O 0.743(3) 0.038(3) 0.4492(7) 0.138(10) .3
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'
I I -0.4742 1.8119 '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 C1 C10A 114.1(5)
C3 N2 C11 111.3(4)
C3 N2 C1 108.9(5)
C11 N2 C1 107.6(5)
C4 C3 N2 109.2(5)
C4A C4 C3 113.2(5)
C5 C4A C10A 112.7(5)
C5 C4A C4 114.6(5)
C10A C4A C4 108.7(5)
C6 C5 C18 121.7(6)
C6 C5 C4A 121.8(5)
C18 C5 C4A 115.9(6)
C7 C6 C5 125.6(6)
C7A C7 C6 114.1(5)
N8 C7A C10A 105.7(4)
N8 C7A C7 115.4(5)
C10A C7A C7 114.9(5)
C9 N8 C20 108.6(6)
C9 N8 C21 111.5(5)
C9 N8 C7A 104.1(4)
C20 N8 C21 108.5(5)
C20 N8 C7A 114.7(5)
C21 N8 C7A 109.5(5)
C10 C9 N8 108.0(5)
C10A C10 C9 105.1(5)
C1 C10A C4A 111.0(4)
C1 C10A C7A 105.8(5)
C1 C10A C10 113.8(5)
C4A C10A C7A 113.9(5)
C4A C10A C10 110.2(5)
C7A C10A C10 101.9(4)
C12 C11 N2 113.7(5)
C13 C12 C17 117.6(6)
C13 C12 C11 120.2(5)
C17 C12 C11 122.2(6)
C14 C13 C12 120.8(6)
C15 C14 C13 120.4(7)
C16 C15 C14 120.5(7)
C17 C16 C15 118.8(6)
C12 C17 C16 121.9(6)
O19 C18 O19A 76.9(8)
O19 C18 C5 117.5(7)
O19A C18 C5 115.5(8)
O19A O19 C18 49.6(7)
C18 O19A O19 53.5(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N2 C1 1.455(8)
C10A C1 1.536(8)
C3 N2 1.479(8)
C11 N2 1.494(8)
C4 C3 1.509(9)
C4A C4 1.537(8)
C5 C4A 1.535(8)
C10A C4A 1.556(8)
C6 C5 1.325(9)
C18 C5 1.490(9)
C7 C6 1.493(9)
C7A C7 1.512(9)
N8 C7A 1.549(7)
C10A C7A 1.522(8)
C9 N8 1.525(9)
C20 N8 1.499(8)
C21 N8 1.486(9)
C10 C9 1.510(10)
C10A C10 1.530(9)
C12 C11 1.493(9)
C13 C12 1.390(9)
C17 C12 1.387(9)
C14 C13 1.382(10)
C15 C14 1.365(11)
C16 C15 1.382(10)
C17 C16 1.384(10)
O19 C18 1.339(10)
O19A C18 1.27(2)
O19A O19 1.62(2)
