#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/33/4023305.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_4023305
loop_
_publ_author_name
'Rishi G. Vaswani'
'A. Richard Chamberlin'
_publ_section_title
;
 Stereocontrolled Total Synthesis of (-)-Kaitocephalin
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1661
_journal_page_last               1681
_journal_paper_doi               10.1021/jo702329z
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C14 H16 N2 O2'
_chemical_formula_weight         244.29
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5277(8)
_cell_length_b                   10.5566(9)
_cell_length_c                   12.3874(10)
_cell_measurement_temperature    163(2)
_cell_volume                     1245.93(18)
_computing_cell_refinement       'Bruker SMART/SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      163(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0172
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14989
_diffrn_reflns_theta_full        27.10
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        '< 1.0'
_diffrn_standards_interval_count 'initial 50 frames recollected'
_diffrn_standards_number         '50 frames'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9825
_exptl_absorpt_correction_T_min  0.9723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(11)
_refine_ls_extinction_coef       0.002(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2748
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0318
_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)+(0.0525P)²+0.1726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0821
_refine_ls_wR_factor_ref         0.0861
_reflns_number_gt                2569
_reflns_number_total             2748
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702329z-File005.cif
_cod_data_source_block           arc7
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'n/a' 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               4023305
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.18197(10) 0.49645(10) 0.03476(7) 0.0298(2) Uani 1 1 d . . .
O2 O 0.09144(12) 0.21102(11) 0.28479(9) 0.0394(3) Uani 1 1 d . . .
N1 N 0.15491(12) 0.34745(11) -0.09805(9) 0.0258(2) Uani 1 1 d . . .
N2 N -0.00726(13) 0.33432(11) 0.15723(8) 0.0255(2) Uani 1 1 d . . .
C1 C 0.08573(15) 0.22513(13) -0.11719(11) 0.0281(3) Uani 1 1 d . . .
C2 C 0.01171(19) 0.24771(15) -0.22505(12) 0.0358(3) Uani 1 1 d . . .
C3 C 0.10675(18) 0.34184(16) -0.28468(12) 0.0370(4) Uani 1 1 d . . .
C4 C 0.18539(18) 0.41745(15) -0.19721(11) 0.0342(3) Uani 1 1 d . . .
C5 C 0.14445(13) 0.39111(12) 0.00240(11) 0.0236(3) Uani 1 1 d . . .
C6 C 0.07813(14) 0.28508(13) 0.07040(11) 0.0254(3) Uani 1 1 d . . .
C7 C -0.00222(18) 0.20762(14) -0.01492(11) 0.0313(3) Uani 1 1 d . . .
C8 C 0.00564(15) 0.29198(13) 0.25970(10) 0.0259(3) Uani 1 1 d . . .
C9 C -0.09277(14) 0.34856(13) 0.34150(10) 0.0246(3) Uani 1 1 d . . .
C10 C -0.18648(16) 0.44642(13) 0.31863(11) 0.0258(3) Uani 1 1 d . . .
C11 C -0.27631(15) 0.49167(15) 0.39777(11) 0.0290(3) Uani 1 1 d . . .
C12 C -0.27623(15) 0.43794(15) 0.50053(13) 0.0313(3) Uani 1 1 d . . .
C13 C -0.18351(17) 0.34094(16) 0.52363(11) 0.0348(3) Uani 1 1 d . . .
C14 C -0.09116(16) 0.29733(15) 0.44558(12) 0.0319(3) Uani 1 1 d . . .
H1 H 0.1570(16) 0.1566(16) -0.1223(12) 0.026(4) Uiso 1 1 d . . .
H2 H -0.0672(19) 0.3956(18) 0.1440(14) 0.031(4) Uiso 1 1 d . . .
H2A H 0.002(2) 0.171(2) -0.2642(17) 0.056(6) Uiso 1 1 d . . .
H2B H -0.080(2) 0.2817(17) -0.2122(15) 0.036(4) Uiso 1 1 d . . .
H3A H 0.175(2) 0.2958(16) -0.3311(14) 0.034(4) Uiso 1 1 d . . .
H3B H 0.052(2) 0.3930(18) -0.3285(16) 0.043(5) Uiso 1 1 d . . .
H4A H 0.1523(17) 0.5053(17) -0.1897(13) 0.028(4) Uiso 1 1 d . . .
H4B H 0.290(2) 0.4216(19) -0.2119(17) 0.050(6) Uiso 1 1 d . . .
H6 H 0.1515(19) 0.2334(16) 0.1013(14) 0.033(4) Uiso 1 1 d . . .
H7A H -0.0961(19) 0.2475(16) -0.0277(13) 0.030(4) Uiso 1 1 d . . .
H7B H -0.010(2) 0.120(2) 0.0083(17) 0.055(6) Uiso 1 1 d . . .
H10 H -0.1894(19) 0.4843(17) 0.2475(14) 0.032(4) Uiso 1 1 d . . .
H11 H -0.338(2) 0.5603(19) 0.3831(17) 0.048(5) Uiso 1 1 d . . .
H12 H -0.3364(19) 0.4659(15) 0.5533(15) 0.032(4) Uiso 1 1 d . . .
H13 H -0.179(2) 0.3088(19) 0.5935(17) 0.052(5) Uiso 1 1 d . . .
H14 H -0.024(2) 0.2255(17) 0.4611(14) 0.037(5) Uiso 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'
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
_geom_angle_publ_flag
C5 N1 C4 128.70(12) . . ?
C5 N1 C1 114.95(11) . . ?
C4 N1 C1 113.43(11) . . ?
C8 N2 C6 121.93(12) . . ?
N1 C1 C2 102.17(12) . . ?
N1 C1 C7 102.61(11) . . ?
C2 C1 C7 119.31(13) . . ?
C1 C2 C3 104.44(13) . . ?
C2 C3 C4 106.51(12) . . ?
N1 C4 C3 103.44(13) . . ?
O1 C5 N1 126.43(13) . . ?
O1 C5 C6 126.65(12) . . ?
N1 C5 C6 106.92(11) . . ?
N2 C6 C5 112.17(11) . . ?
N2 C6 C7 114.95(11) . . ?
C5 C6 C7 102.41(11) . . ?
C1 C7 C6 103.41(12) . . ?
O2 C8 N2 122.06(13) . . ?
O2 C8 C9 121.54(12) . . ?
N2 C8 C9 116.40(12) . . ?
C10 C9 C14 118.74(13) . . ?
C10 C9 C8 123.81(12) . . ?
C14 C9 C8 117.43(12) . . ?
C11 C10 C9 120.46(12) . . ?
C10 C11 C12 120.35(14) . . ?
C13 C12 C11 119.40(14) . . ?
C12 C13 C14 120.49(13) . . ?
C13 C14 C9 120.51(14) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.2350(17) . ?
O2 C8 1.2228(18) . ?
N1 C5 1.3307(17) . ?
N1 C4 1.4626(18) . ?
N1 C1 1.4690(18) . ?
N2 C8 1.3514(16) . ?
N2 C6 1.4453(17) . ?
C1 C2 1.529(2) . ?
C1 C7 1.530(2) . ?
C2 C3 1.534(3) . ?
C3 C4 1.540(2) . ?
C5 C6 1.5368(19) . ?
C6 C7 1.5400(19) . ?
C8 C9 1.5043(19) . ?
C9 C10 1.394(2) . ?
C9 C14 1.3982(19) . ?
C10 C11 1.386(2) . ?
C11 C12 1.394(2) . ?
C12 C13 1.382(2) . ?
C13 C14 1.386(2) . ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 136.18(12) . . . . ?
C4 N1 C1 C2 -26.21(15) . . . . ?
C5 N1 C1 C7 12.02(15) . . . . ?
C4 N1 C1 C7 -150.37(12) . . . . ?
N1 C1 C2 C3 31.26(13) . . . . ?
C7 C1 C2 C3 143.43(13) . . . . ?
C1 C2 C3 C4 -26.78(15) . . . . ?
C5 N1 C4 C3 -149.73(13) . . . . ?
C1 N1 C4 C3 9.69(15) . . . . ?
C2 C3 C4 N1 11.15(15) . . . . ?
C4 N1 C5 O1 -13.3(2) . . . . ?
C1 N1 C5 O1 -172.51(12) . . . . ?
C4 N1 C5 C6 167.16(13) . . . . ?
C1 N1 C5 C6 8.00(14) . . . . ?
C8 N2 C6 C5 -131.31(13) . . . . ?
C8 N2 C6 C7 112.23(15) . . . . ?
O1 C5 C6 N2 32.33(18) . . . . ?
N1 C5 C6 N2 -148.18(11) . . . . ?
O1 C5 C6 C7 156.12(14) . . . . ?
N1 C5 C6 C7 -24.38(13) . . . . ?
N1 C1 C7 C6 -26.29(14) . . . . ?
C2 C1 C7 C6 -138.22(13) . . . . ?
N2 C6 C7 C1 152.62(11) . . . . ?
C5 C6 C7 C1 30.71(13) . . . . ?
C6 N2 C8 O2 1.0(2) . . . . ?
C6 N2 C8 C9 -178.21(11) . . . . ?
O2 C8 C9 C10 175.93(14) . . . . ?
N2 C8 C9 C10 -4.86(19) . . . . ?
O2 C8 C9 C14 -5.48(19) . . . . ?
N2 C8 C9 C14 173.73(13) . . . . ?
C14 C9 C10 C11 -0.1(2) . . . . ?
C8 C9 C10 C11 178.49(13) . . . . ?
C9 C10 C11 C12 -1.5(2) . . . . ?
C10 C11 C12 C13 1.5(2) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C9 -1.6(2) . . . . ?
C10 C9 C14 C13 1.6(2) . . . . ?
C8 C9 C14 C13 -177.05(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658647
