#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/29/4022909.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_4022909
loop_
_publ_author_name
'Jianguang Zhou'
'Nabi A. Magomedov'
_publ_section_title
;
 Explorations on the Asymmetric Total Synthesis of Isoschizogamine
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3808
_journal_page_last               3815
_journal_paper_doi               10.1021/jo070144x
_journal_volume                  72
_journal_year                    2007
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C21 H26 N2 O3'
_chemical_formula_sum            'C21 H26 N2 O3'
_chemical_formula_weight         354.44
_chemical_name_common            MAGJZ01
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 95.483(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.6107(11)
_cell_length_b                   5.6461(5)
_cell_length_c                   14.4520(13)
_cell_measurement_reflns_used    3442
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      2.8
_cell_volume                     943.07(15)
_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      193(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_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  0.0694
_diffrn_reflns_av_sigmaI/netI    0.1161
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11475
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.76
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         4392
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.1521
_refine_ls_R_factor_gt           0.0884
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0445P)²+0.4635P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1493
_reflns_number_gt                2643
_reflns_number_total             4392
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo070144xsi20070123_102145.cif
_cod_data_source_block           asd
_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_sg_symbol_H-M      'P 21'
_cod_database_code               4022909
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 0.4547(2) 0.4962(5) 0.38300(19) 0.0411(8) Uani 1 1 d .
O2 O 0.5761(2) 0.6631(5) 0.24487(19) 0.0391(7) Uani 1 1 d .
N1 N 0.1359(2) 1.0211(5) 0.2859(2) 0.0301(8) Uani 1 1 d .
H1A H 0.0890 0.9480 0.3209 0.036 Uiso 1 1 calc R
C2 C 0.2936(3) 0.7596(7) 0.3341(2) 0.0297(9) Uani 1 1 d .
H2A H 0.2506 0.7069 0.3829 0.036 Uiso 1 1 calc R
C6 C 0.3084(3) 1.0099(7) 0.1999(2) 0.0273(9) Uani 1 1 d .
C1 C 0.2458(3) 0.9327(6) 0.2719(3) 0.0259(9) Uani 1 1 d .
C5 C 0.4162(3) 0.9090(7) 0.1925(3) 0.0327(9) Uani 1 1 d .
H5A H 0.4586 0.9577 0.1428 0.039 Uiso 1 1 calc R
C3 C 0.4020(3) 0.6643(7) 0.3258(3) 0.0315(10) Uani 1 1 d .
C4 C 0.4645(3) 0.7426(7) 0.2535(3) 0.0302(9) Uani 1 1 d .
O3 O 0.0579(2) 1.2528(6) 0.45664(18) 0.0513(8) Uani 1 1 d .
C11 C -0.0221(3) 1.3241(6) 0.2344(3) 0.0263(9) Uani 1 1 d .
C19 C -0.0335(4) 1.2629(8) 0.4051(3) 0.0374(10) Uani 1 1 d .
C8 C 0.1304(3) 1.2235(7) 0.1377(2) 0.0279(9) Uani 1 1 d .
H8A H 0.0934 1.0762 0.1104 0.033 Uiso 1 1 calc R
C22 C -0.1066(3) 1.1303(7) 0.2035(3) 0.0282(9) Uani 1 1 d .
H22A H -0.0993 1.0685 0.1432 0.034 Uiso 1 1 calc R
C7 C 0.2615(3) 1.2065(7) 0.1332(2) 0.0273(9) Uani 1 1 d .
H7A H 0.2965 1.3595 0.1566 0.033 Uiso 1 1 calc R
C12 C 0.1052(3) 1.2422(7) 0.2384(2) 0.0241(8) Uani 1 1 d .
H12A H 0.1550 1.3705 0.2685 0.029 Uiso 1 1 calc R
C21 C -0.1891(3) 1.0339(7) 0.2477(3) 0.0303(9) Uani 1 1 d .
H21A H -0.2371 0.9227 0.2131 0.036 Uiso 1 1 calc R
C9 C 0.0679(3) 1.4403(8) 0.0915(3) 0.0425(11) Uani 1 1 d .
H9A H 0.1235 1.5702 0.0839 0.051 Uiso 1 1 calc R
H9B H 0.0296 1.3977 0.0296 0.051 Uiso 1 1 calc R
N2 N -0.1167(3) 1.1057(7) 0.4128(2) 0.0428(9) Uani 1 1 d .
H2B H -0.1110 1.0128 0.4619 0.051 Uiso 1 1 calc R
C15 C 0.2930(3) 1.1717(8) 0.0361(3) 0.0377(11) Uani 1 1 d .
H15A H 0.2774 1.0216 0.0080 0.045 Uiso 1 1 calc R
C20 C -0.2173(3) 1.0762(8) 0.3450(3) 0.0389(10) Uani 1 1 d .
H20A H -0.2659 1.2201 0.3458 0.047 Uiso 1 1 calc R
H20B H -0.2637 0.9412 0.3645 0.047 Uiso 1 1 calc R
C14 C 0.3897(4) 0.3996(9) 0.4525(3) 0.0544(13) Uani 1 1 d .
H14A H 0.4365 0.2814 0.4887 0.082 Uiso 1 1 calc R
H14B H 0.3195 0.3243 0.4230 0.082 Uiso 1 1 calc R
H14C H 0.3682 0.5265 0.4938 0.082 Uiso 1 1 calc R
C10 C -0.0221(3) 1.5161(7) 0.1568(3) 0.0371(10) Uani 1 1 d .
H10A H -0.0997 1.5275 0.1221 0.045 Uiso 1 1 calc R
H10B H -0.0016 1.6727 0.1845 0.045 Uiso 1 1 calc R
C18 C -0.0511(3) 1.4376(7) 0.3261(3) 0.0343(10) Uani 1 1 d .
H18A H -0.0008 1.5773 0.3400 0.041 Uiso 1 1 calc R
H18B H -0.1325 1.4921 0.3197 0.041 Uiso 1 1 calc R
C16 C 0.3405(4) 1.3333(11) -0.0127(3) 0.0575(15) Uani 1 1 d .
H16A H 0.3573 1.4855 0.0132 0.08(2) Uiso 1 1 calc R
H16B H 0.3582 1.2986 -0.0741 0.071(16) Uiso 1 1 calc R
C13 C 0.5788(4) 0.4365(8) 0.2021(3) 0.0498(12) Uani 1 1 d .
H13A H 0.6593 0.3889 0.1980 0.075 Uiso 1 1 calc R
H13B H 0.5382 0.4440 0.1395 0.075 Uiso 1 1 calc R
H13C H 0.5407 0.3204 0.2393 0.075 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 0.0033 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C3 O1 C14 117.2(3)
C4 O2 C13 112.9(3)
C1 N1 C12 115.0(3)
C3 C2 C1 121.4(3)
C5 C6 C1 117.8(3)
C5 C6 C7 121.1(3)
C1 C6 C7 121.0(3)
C6 C1 N1 122.9(3)
C6 C1 C2 119.5(3)
N1 C1 C2 117.6(3)
C4 C5 C6 123.3(4)
O1 C3 C2 125.2(4)
O1 C3 C4 116.0(3)
C2 C3 C4 118.9(4)
C5 C4 O2 119.5(4)
C5 C4 C3 119.1(4)
O2 C4 C3 121.3(4)
C22 C11 C18 111.6(3)
C22 C11 C12 112.8(3)
C18 C11 C12 112.3(3)
C22 C11 C10 109.6(3)
C18 C11 C10 110.2(3)
C12 C11 C10 99.7(3)
O3 C19 N2 120.6(4)
O3 C19 C18 122.1(4)
N2 C19 C18 117.0(3)
C12 C8 C7 109.2(3)
C12 C8 C9 103.5(3)
C7 C8 C9 117.4(3)
C21 C22 C11 129.6(3)
C15 C7 C8 112.4(3)
C15 C7 C6 112.9(3)
C8 C7 C6 108.2(3)
N1 C12 C8 109.4(3)
N1 C12 C11 117.8(3)
C8 C12 C11 104.9(3)
C22 C21 C20 128.7(4)
C10 C9 C8 106.0(3)
C19 N2 C20 124.3(3)
C16 C15 C7 124.6(4)
N2 C20 C21 114.6(3)
C9 C10 C11 107.2(3)
C19 C18 C11 110.8(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C3 1.365(4)
O1 C14 1.422(5)
O2 C4 1.388(4)
O2 C13 1.423(5)
N1 C1 1.403(4)
N1 C12 1.453(5)
C2 C3 1.385(5)
C2 C1 1.405(5)
C6 C5 1.388(5)
C6 C1 1.395(5)
C6 C7 1.535(5)
C5 C4 1.370(5)
C3 C4 1.400(5)
O3 C19 1.238(4)
C11 C22 1.508(5)
C11 C18 1.538(5)
C11 C12 1.544(5)
C11 C10 1.560(5)
C19 N2 1.324(5)
C19 C18 1.508(5)
C8 C12 1.515(5)
C8 C7 1.533(5)
C8 C9 1.542(5)
C22 C21 1.320(5)
C7 C15 1.496(5)
C21 C20 1.492(5)
C9 C10 1.534(5)
N2 C20 1.460(4)
C15 C16 1.307(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 17596867
