#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/86/1508630.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_1508630
loop_
_publ_author_name
'Villa, Reymundo A.'
'Xu, Qihai'
'Kwon, Ohyun'
_publ_section_title
;
 Total synthesis of (+-)-hirsutine: application of phosphine-catalyzed
 imine-allene [4 + 2] annulation.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4634
_journal_page_last               4637
_journal_paper_doi               10.1021/ol302077n
_journal_volume                  14
_journal_year                    2012
_chemical_formula_moiety         '2(C21 H24 N2 O5), C H2 Cl2'
_chemical_formula_sum            'C43 H50 Cl2 N4 O10'
_chemical_formula_weight         853.77
_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                 100.2810(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   28.956(3)
_cell_length_b                   12.8042(11)
_cell_length_c                   11.6536(10)
_cell_measurement_reflns_used    9596
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.95
_cell_measurement_theta_min      3.91
_cell_volume                     4251.3(7)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0167
_diffrn_reflns_av_sigmaI/netI    0.0170
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20317
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.97
_diffrn_reflns_theta_min         3.84
_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Bruker)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.607
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         6073
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0437
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0603P)²+3.7405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1226
_reflns_number_gt                5096
_reflns_number_total             6073
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol302077n_si_003.cif
_cod_data_source_block           kw1208s
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1508630
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
O1 O 0.17556(3) 0.09370(7) -0.03995(8) 0.0272(2) Uani 1 1 d .
O2 O 0.07680(4) 0.13529(8) 0.39184(8) 0.0351(2) Uani 1 1 d .
O3 O 0.06493(4) 0.02554(9) 0.24001(9) 0.0424(3) Uani 1 1 d .
O4 O 0.04341(4) 0.19800(9) 0.03765(10) 0.0437(3) Uani 1 1 d .
O5 O 0.04398(4) 0.32853(9) 0.16410(10) 0.0436(3) Uani 1 1 d .
N1 N 0.25010(3) 0.05672(7) 0.45896(8) 0.01764(18) Uani 1 1 d .
H1 H 0.2242 0.0231 0.4657 0.021 Uiso 1 1 calc R
N2 N 0.23014(3) 0.25098(7) 0.21845(8) 0.01709(18) Uani 1 1 d .
C1 C 0.32599(4) 0.10758(9) 0.48354(9) 0.0193(2) Uani 1 1 d .
C2 C 0.37360(4) 0.10294(10) 0.53474(11) 0.0255(2) Uani 1 1 d .
H2 H 0.3957 0.1488 0.5101 0.031 Uiso 1 1 calc R
C3 C 0.38786(5) 0.03005(11) 0.62208(12) 0.0295(3) Uani 1 1 d .
H3 H 0.4201 0.0259 0.6567 0.035 Uiso 1 1 calc R
C4 C 0.35561(4) -0.03755(10) 0.66019(11) 0.0264(2) Uani 1 1 d .
H4 H 0.3664 -0.0856 0.7212 0.032 Uiso 1 1 calc R
C5 C 0.30837(4) -0.03581(9) 0.61072(10) 0.0211(2) Uani 1 1 d .
H5 H 0.2865 -0.0818 0.6362 0.025 Uiso 1 1 calc R
C6 C 0.29434(4) 0.03665(8) 0.52177(9) 0.0180(2) Uani 1 1 d .
C7 C 0.25342(4) 0.13875(8) 0.38363(9) 0.0170(2) Uani 1 1 d .
C8 C 0.29874(4) 0.17265(9) 0.39625(9) 0.0187(2) Uani 1 1 d .
C9 C 0.31177(4) 0.26416(9) 0.32853(10) 0.0215(2) Uani 1 1 d .
H9A H 0.3283 0.2397 0.2662 0.026 Uiso 1 1 calc R
H9B H 0.3331 0.3112 0.3808 0.026 Uiso 1 1 calc R
C10 C 0.26719(4) 0.32287(9) 0.27495(10) 0.0200(2) Uani 1 1 d .
H10A H 0.2555 0.3628 0.3367 0.024 Uiso 1 1 calc R
H10B H 0.2746 0.3733 0.2165 0.024 Uiso 1 1 calc R
C11 C 0.21221(4) 0.18541(8) 0.30523(9) 0.01634(19) Uani 1 1 d .
H11 H 0.1946 0.2306 0.3525 0.020 Uiso 1 1 calc R
C12 C 0.17881(4) 0.10271(8) 0.24164(9) 0.0175(2) Uani 1 1 d .
H12A H 0.1662 0.0602 0.2999 0.021 Uiso 1 1 calc R
H12B H 0.1967 0.0556 0.1982 0.021 Uiso 1 1 calc R
C13 C 0.13765(4) 0.15059(8) 0.15608(9) 0.0176(2) Uani 1 1 d .
H13 H 0.1231 0.0938 0.1027 0.021 Uiso 1 1 calc R
C14 C 0.15642(4) 0.23405(8) 0.08131(9) 0.0186(2) Uani 1 1 d .
H14 H 0.1291 0.2751 0.0398 0.022 Uiso 1 1 calc R
C15 C 0.19065(4) 0.31013(8) 0.15267(9) 0.0197(2) Uani 1 1 d .
H15A H 0.2023 0.3607 0.1002 0.024 Uiso 1 1 calc R
H15B H 0.1746 0.3495 0.2071 0.024 Uiso 1 1 calc R
C16 C 0.18042(4) 0.18370(10) -0.00933(9) 0.0221(2) Uani 1 1 d .
H16 H 0.2009 0.2259 -0.0449 0.027 Uiso 1 1 calc R
C17 C 0.09934(4) 0.19501(9) 0.21850(10) 0.0197(2) Uani 1 1 d .
H17 H 0.1127 0.2510 0.2745 0.024 Uiso 1 1 calc R
C18 C 0.07845(4) 0.10795(10) 0.28291(10) 0.0234(2) Uani 1 1 d .
C19 C 0.05648(7) 0.05733(14) 0.45909(13) 0.0443(4) Uani 1 1 d .
H19A H 0.0228 0.0513 0.4289 0.067 Uiso 1 1 calc R
H19B H 0.0613 0.0786 0.5412 0.067 Uiso 1 1 calc R
H19C H 0.0716 -0.0103 0.4525 0.067 Uiso 1 1 calc R
C20 C 0.05926(4) 0.23857(10) 0.12879(10) 0.0235(2) Uani 1 1 d .
C21 C 0.00606(8) 0.37628(18) 0.08326(19) 0.0675(7) Uani 1 1 d .
H21A H 0.0157 0.3854 0.0074 0.070 Uiso 1 1 calc R
H21B H -0.0014 0.4445 0.1134 0.070 Uiso 1 1 calc R
H21C H -0.0217 0.3312 0.0743 0.070 Uiso 1 1 calc R
C22 C 0.5000 0.30086(19) 0.2500 0.0429(5) Uani 1 2 d S
H22A H 0.5075 0.3464 0.3195 0.051 Uiso 0.50 1 calc PR
H22B H 0.4925 0.3464 0.1805 0.051 Uiso 0.50 1 calc PR
Cl1 Cl 0.45095(3) 0.22557(6) 0.26145(7) 0.0947(3) Uani 1 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'
Cl Cl 0.1484 0.1585 '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
C18 O2 C19 114.92(12) . .
C20 O5 C21 114.91(13) . .
C6 N1 C7 108.35(9) . .
C6 N1 H1 125.8 . .
C7 N1 H1 125.8 . .
C15 N2 C10 110.33(8) . .
C15 N2 C11 108.31(8) . .
C10 N2 C11 111.41(8) . .
C2 C1 C6 118.74(10) . .
C2 C1 C8 134.40(11) . .
C6 C1 C8 106.85(10) . .
C3 C2 C1 118.79(12) . .
C3 C2 H2 120.6 . .
C1 C2 H2 120.6 . .
C2 C3 C4 121.29(11) . .
C2 C3 H3 119.4 . .
C4 C3 H3 119.4 . .
C5 C4 C3 121.44(11) . .
C5 C4 H4 119.3 . .
C3 C4 H4 119.3 . .
C4 C5 C6 117.01(11) . .
C4 C5 H5 121.5 . .
C6 C5 H5 121.5 . .
N1 C6 C5 129.53(11) . .
N1 C6 C1 107.74(9) . .
C5 C6 C1 122.70(10) . .
C8 C7 N1 110.33(9) . .
C8 C7 C11 125.95(10) . .
N1 C7 C11 123.65(9) . .
C7 C8 C1 106.72(10) . .
C7 C8 C9 121.30(10) . .
C1 C8 C9 131.94(10) . .
C8 C9 C10 109.05(9) . .
C8 C9 H9A 109.9 . .
C10 C9 H9A 109.9 . .
C8 C9 H9B 109.9 . .
C10 C9 H9B 109.9 . .
H9A C9 H9B 108.3 . .
N2 C10 C9 111.67(9) . .
N2 C10 H10A 109.3 . .
C9 C10 H10A 109.3 . .
N2 C10 H10B 109.3 . .
C9 C10 H10B 109.3 . .
H10A C10 H10B 107.9 . .
N2 C11 C7 107.83(9) . .
N2 C11 C12 109.26(8) . .
C7 C11 C12 112.71(9) . .
N2 C11 H11 109.0 . .
C7 C11 H11 109.0 . .
C12 C11 H11 109.0 . .
C11 C12 C13 112.76(9) . .
C11 C12 H12A 109.0 . .
C13 C12 H12A 109.0 . .
C11 C12 H12B 109.0 . .
C13 C12 H12B 109.0 . .
H12A C12 H12B 107.8 . .
C14 C13 C12 109.45(9) . .
C14 C13 C17 111.60(9) . .
C12 C13 C17 112.41(9) . .
C14 C13 H13 107.7 . .
C12 C13 H13 107.7 . .
C17 C13 H13 107.7 . .
C16 C14 C15 108.59(9) . .
C16 C14 C13 110.68(9) . .
C15 C14 C13 113.30(9) . .
C16 C14 H14 108.0 . .
C15 C14 H14 108.0 . .
C13 C14 H14 108.0 . .
N2 C15 C14 108.95(9) . .
N2 C15 H15A 109.9 . .
C14 C15 H15A 109.9 . .
N2 C15 H15B 109.9 . .
C14 C15 H15B 109.9 . .
H15A C15 H15B 108.3 . .
O1 C16 C14 124.82(11) . .
O1 C16 H16 117.6 . .
C14 C16 H16 117.6 . .
C20 C17 C18 106.54(9) . .
C20 C17 C13 109.64(9) . .
C18 C17 C13 110.14(9) . .
C20 C17 H17 110.2 . .
C18 C17 H17 110.2 . .
C13 C17 H17 110.2 . .
O3 C18 O2 124.39(12) . .
O3 C18 C17 124.33(11) . .
O2 C18 C17 111.28(11) . .
O2 C19 H19A 109.5 . .
O2 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
O2 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
O4 C20 O5 123.78(12) . .
O4 C20 C17 125.06(11) . .
O5 C20 C17 111.17(10) . .
O5 C21 H21A 109.5 . .
O5 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
O5 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
Cl1 C22 Cl1 112.76(15) . 2_655
Cl1 C22 H22A 109.0 . .
Cl1 C22 H22A 109.0 2_655 .
Cl1 C22 H22B 109.0 . .
Cl1 C22 H22B 109.0 2_655 .
H22A C22 H22B 107.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C16 1.2071(15) .
O2 C18 1.3258(15) .
O2 C19 1.4566(17) .
O3 C18 1.2028(16) .
O4 C20 1.1977(16) .
O5 C20 1.3255(16) .
O5 C21 1.4482(19) .
N1 C6 1.3812(14) .
N1 C7 1.3832(14) .
N1 H1 0.8800 .
N2 C15 1.4683(14) .
N2 C10 1.4764(14) .
N2 C11 1.4781(13) .
C1 C2 1.4023(16) .
C1 C6 1.4174(16) .
C1 C8 1.4370(15) .
C2 C3 1.3884(18) .
C2 H2 0.9500 .
C3 C4 1.4022(19) .
C3 H3 0.9500 .
C4 C5 1.3865(17) .
C4 H4 0.9500 .
C5 C6 1.3964(15) .
C5 H5 0.9500 .
C7 C8 1.3649(15) .
C7 C11 1.4921(15) .
C8 C9 1.4981(16) .
C9 C10 1.5274(16) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.5329(15) .
C11 H11 1.0000 .
C12 C13 1.5383(15) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 C14 1.5380(15) .
C13 C17 1.5399(15) .
C13 H13 1.0000 .
C14 C16 1.5087(15) .
C14 C15 1.5260(16) .
C14 H14 1.0000 .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 H16 0.9500 .
C17 C20 1.5225(16) .
C17 C18 1.5276(16) .
C17 H17 1.0000 .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
C21 H21A 0.9800 .
C21 H21B 0.9800 .
C21 H21C 0.9800 .
C22 Cl1 1.7412(15) .
C22 Cl1 1.7412(15) 2_655
C22 H22A 0.9900 .
C22 H22B 0.9900 .
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
C6 C1 C2 C3 -0.88(17)
C8 C1 C2 C3 177.70(12)
C1 C2 C3 C4 -0.64(19)
C2 C3 C4 C5 1.3(2)
C3 C4 C5 C6 -0.35(18)
C7 N1 C6 C5 177.37(11)
C7 N1 C6 C1 -0.53(12)
C4 C5 C6 N1 -178.85(11)
C4 C5 C6 C1 -1.23(16)
C2 C1 C6 N1 179.94(10)
C8 C1 C6 N1 1.00(12)
C2 C1 C6 C5 1.86(16)
C8 C1 C6 C5 -177.07(10)
C6 N1 C7 C8 -0.18(12)
C6 N1 C7 C11 -177.24(9)
N1 C7 C8 C1 0.80(12)
C11 C7 C8 C1 177.78(10)
N1 C7 C8 C9 -177.27(10)
C11 C7 C8 C9 -0.29(17)
C2 C1 C8 C7 -179.80(12)
C6 C1 C8 C7 -1.10(12)
C2 C1 C8 C9 -2.0(2)
C6 C1 C8 C9 176.69(11)
C7 C8 C9 C10 14.15(14)
C1 C8 C9 C10 -163.37(11)
C15 N2 C10 C9 -171.34(9)
C11 N2 C10 C9 68.32(11)
C8 C9 C10 N2 -46.51(12)
C15 N2 C11 C7 -171.22(8)
C10 N2 C11 C7 -49.70(11)
C15 N2 C11 C12 65.96(10)
C10 N2 C11 C12 -172.51(9)
C8 C7 C11 N2 17.50(14)
N1 C7 C11 N2 -165.90(9)
C8 C7 C11 C12 138.18(11)
N1 C7 C11 C12 -45.22(14)
N2 C11 C12 C13 -57.21(11)
C7 C11 C12 C13 -177.07(9)
C11 C12 C13 C14 47.17(12)
C11 C12 C13 C17 -77.43(11)
C12 C13 C14 C16 74.58(11)
C17 C13 C14 C16 -160.34(9)
C12 C13 C14 C15 -47.67(12)
C17 C13 C14 C15 77.41(11)
C10 N2 C15 C14 171.80(8)
C11 N2 C15 C14 -66.00(10)
C16 C14 C15 N2 -65.51(11)
C13 C14 C15 N2 57.89(12)
C15 C14 C16 O1 142.65(12)
C13 C14 C16 O1 17.68(16)
C14 C13 C17 C20 57.98(12)
C12 C13 C17 C20 -178.61(9)
C14 C13 C17 C18 174.91(9)
C12 C13 C17 C18 -61.68(12)
C19 O2 C18 O3 -0.6(2)
C19 O2 C18 C17 178.88(11)
C20 C17 C18 O3 69.58(16)
C13 C17 C18 O3 -49.27(16)
C20 C17 C18 O2 -109.90(11)
C13 C17 C18 O2 131.26(10)
C21 O5 C20 O4 -0.3(2)
C21 O5 C20 C17 179.37(15)
C18 C17 C20 O4 -77.72(16)
C13 C17 C20 O4 41.45(17)
C18 C17 C20 O5 102.63(12)
C13 C17 C20 O5 -138.20(11)
