#------------------------------------------------------------------------------
#$Date: 2017-07-11 15:10:40 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198633 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/11/15/4111531.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_4111531
loop_
_publ_author_name
'Arunkumar Natarajan'
'Joel T. Mague'
'V. Ramamurthy'
_publ_section_title
;
 Asymmetric Induction during Yang Cyclization of α-Oxoamides: The Power
 of a Covalently Linked Chiral Auxiliary Is Enhanced in the Crystalline
 State
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3568
_journal_page_last               3576
_journal_paper_doi               10.1021/ja043999p
_journal_volume                  127
_journal_year                    2005
_chemical_formula_sum            'C25 H30 N2 O6'
_chemical_formula_weight         454.51
_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                 93.2060(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.8848(8)
_cell_length_b                   7.8596(5)
_cell_length_c                   12.7623(8)
_cell_measurement_reflns_used    3270
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.06
_cell_measurement_theta_min      2.28
_cell_volume                     1190.26(13)
_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 0.972
_diffrn_measured_fraction_theta_max 0.972
_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  0.0400
_diffrn_reflns_av_sigmaI/netI    0.0831
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10757
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.60
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      0
_exptl_crystal_description       Plate
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.028
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.9(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     305
_refine_ls_number_reflns         5531
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0638
_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)+(0.0486P)²+0.1722P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                3687
_reflns_number_total             5531
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja043999psi20041001_024437.cif
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'constrained' was replaced with
the value 'constr' as specified in the replacement file
'src/cod-tools/trunk/data/replacement-values/replacement_values.lst'.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_cell_volume        1190.26(18)
_cod_database_code               4111531
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 0.04163(18) 1.2992(3) 0.80015(18) 0.0368(5) Uani 1 1 d .
O2 O -0.08907(18) 1.0287(3) 0.92251(16) 0.0380(6) Uani 1 1 d .
O3 O 0.36420(16) 0.5800(3) 0.67217(15) 0.0308(5) Uani 1 1 d .
O4 O 0.25008(18) 0.1681(3) 0.57809(15) 0.0371(6) Uani 1 1 d .
O5 O 0.43601(17) 0.1179(3) 0.59592(16) 0.0412(6) Uani 1 1 d .
O6 O 0.44312(19) 0.2466(3) 1.24859(15) 0.0405(6) Uani 1 1 d .
H6 H 0.5078 0.2125 1.2684 0.061 Uiso 1 1 calc R
N1 N -0.1230(2) 1.2261(3) 0.7072(2) 0.0332(6) Uani 1 1 d .
N2 N 0.2715(2) 0.3762(3) 0.75777(18) 0.0268(6) Uani 1 1 d .
H2N H 0.2052 0.3597 0.7818 0.014(7) Uiso 1 1 d R
C1 C -0.0326(3) 1.4069(5) 0.5759(3) 0.0401(9) Uani 1 1 d .
H1A H -0.0253 1.3055 0.5322 0.060 Uiso 1 1 calc R
H1B H 0.0363 1.4221 0.6208 0.060 Uiso 1 1 calc R
H1C H -0.0445 1.5070 0.5309 0.060 Uiso 1 1 calc R
C2 C -0.1503(3) 1.5402(5) 0.7122(3) 0.0509(10) Uani 1 1 d .
H2A H -0.0826 1.5600 0.7581 0.076 Uiso 1 1 calc R
H2B H -0.2149 1.5205 0.7552 0.076 Uiso 1 1 calc R
H2C H -0.1648 1.6400 0.6675 0.076 Uiso 1 1 calc R
C3 C -0.1324(3) 1.3856(4) 0.6441(3) 0.0360(8) Uani 1 1 d .
H3 H -0.2011 1.3741 0.5957 0.043 Uiso 1 1 calc R
C4 C -0.2380(3) 1.0362(5) 0.5862(3) 0.0554(10) Uani 1 1 d .
H4A H -0.1674 0.9936 0.5598 0.083 Uiso 1 1 calc R
H4B H -0.2666 1.1299 0.5417 0.083 Uiso 1 1 calc R
H4C H -0.2937 0.9442 0.5851 0.083 Uiso 1 1 calc R
C5 C -0.3224(3) 1.1709(5) 0.7440(3) 0.0559(11) Uani 1 1 d .
H5A H -0.3463 1.2738 0.7055 0.084 Uiso 1 1 calc R
H5B H -0.3063 1.1991 0.8181 0.084 Uiso 1 1 calc R
H5C H -0.3826 1.0858 0.7379 0.084 Uiso 1 1 calc R
C6 C -0.2165(3) 1.0996(5) 0.6981(3) 0.0453(9) Uani 1 1 d .
H6A H -0.1924 0.9991 0.7418 0.054 Uiso 1 1 calc R
C7 C -0.0374(3) 1.2022(4) 0.7792(2) 0.0299(7) Uani 1 1 d .
C8 C -0.0375(3) 1.0386(4) 0.8412(2) 0.0352(8) Uani 1 1 d .
C9 C 0.0434(3) 0.9055(4) 0.8098(3) 0.0321(8) Uani 1 1 d .
C10 C 0.0872(3) 0.9095(4) 0.7114(2) 0.0286(7) Uani 1 1 d .
H10 H 0.0642 0.9961 0.6629 0.034 Uiso 1 1 calc R
C11 C 0.1640(2) 0.7885(4) 0.6837(2) 0.0268(7) Uani 1 1 d .
H11 H 0.1949 0.7932 0.6167 0.032 Uiso 1 1 calc R
C12 C 0.1961(2) 0.6602(4) 0.7531(2) 0.0269(7) Uani 1 1 d .
C13 C 0.1524(3) 0.6545(4) 0.8527(2) 0.0363(8) Uani 1 1 d .
H13 H 0.1741 0.5661 0.9004 0.044 Uiso 1 1 calc R
C14 C 0.0776(3) 0.7784(4) 0.8810(2) 0.0374(8) Uani 1 1 d .
H14 H 0.0493 0.7771 0.9492 0.045 Uiso 1 1 calc R
C15 C 0.2834(2) 0.5357(4) 0.7232(2) 0.0253(7) Uani 1 1 d .
C16 C 0.3546(2) 0.2464(4) 0.7395(2) 0.0266(7) Uani 1 1 d .
H16 H 0.4316 0.2971 0.7491 0.032 Uiso 1 1 calc R
C17 C 0.3445(2) 0.0986(4) 0.8168(2) 0.0311(7) Uani 1 1 d .
H17A H 0.2664 0.0544 0.8102 0.037 Uiso 1 1 calc R
H17B H 0.3952 0.0058 0.7964 0.037 Uiso 1 1 calc R
C18 C 0.2927(3) 0.2131(4) 0.9936(2) 0.0318(7) Uani 1 1 d .
H18 H 0.2192 0.2365 0.9639 0.038 Uiso 1 1 calc R
C19 C 0.3177(3) 0.2490(4) 1.0978(2) 0.0325(8) Uani 1 1 d .
H19 H 0.2623 0.2997 1.1386 0.039 Uiso 1 1 calc R
C20 C 0.4234(3) 0.2115(4) 1.1435(2) 0.0304(7) Uani 1 1 d .
C21 C 0.5038(3) 0.1431(4) 1.0819(2) 0.0334(8) Uani 1 1 d .
H21 H 0.5770 0.1187 1.1118 0.040 Uiso 1 1 calc R
C22 C 0.4783(3) 0.1100(4) 0.9772(2) 0.0325(7) Uani 1 1 d .
H22 H 0.5346 0.0632 0.9358 0.039 Uiso 1 1 calc R
C23 C 0.3726(2) 0.1433(4) 0.9309(2) 0.0267(7) Uani 1 1 d .
C24 C 0.3378(3) 0.1768(4) 0.6277(2) 0.0285(7) Uani 1 1 d .
C25 C 0.4306(3) 0.0291(6) 0.4963(2) 0.0491(10) Uani 1 1 d .
H25A H 0.3907 0.0997 0.4429 0.074 Uiso 1 1 calc R
H25B H 0.3902 -0.0787 0.5034 0.074 Uiso 1 1 calc R
H25C H 0.5071 0.0062 0.4752 0.074 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
C24 O5 C25 115.8(2)
C7 N1 C3 121.2(3)
C7 N1 C6 119.5(3)
C3 N1 C6 119.0(3)
C15 N2 C16 121.4(2)
N1 C3 C2 111.9(3)
N1 C3 C1 111.4(3)
C2 C3 C1 112.3(3)
N1 C6 C4 112.2(3)
N1 C6 C5 110.6(3)
C4 C6 C5 112.5(3)
O1 C7 N1 127.0(3)
O1 C7 C8 115.9(3)
N1 C7 C8 117.0(3)
O2 C8 C9 122.5(3)
O2 C8 C7 120.6(3)
C9 C8 C7 116.0(2)
C10 C9 C14 119.7(3)
C10 C9 C8 120.5(3)
C14 C9 C8 119.8(3)
C11 C10 C9 120.3(3)
C10 C11 C12 120.1(3)
C11 C12 C13 120.1(3)
C11 C12 C15 119.0(2)
C13 C12 C15 120.7(3)
C14 C13 C12 119.5(3)
C13 C14 C9 120.2(3)
O3 C15 N2 122.4(3)
O3 C15 C12 121.4(3)
N2 C15 C12 116.2(3)
N2 C16 C24 110.4(2)
N2 C16 C17 110.6(2)
C24 C16 C17 108.5(2)
C23 C17 C16 114.9(3)
C19 C18 C23 121.3(3)
C18 C19 C20 120.4(3)
O6 C20 C21 123.2(3)
O6 C20 C19 118.0(3)
C21 C20 C19 118.9(3)
C22 C21 C20 120.2(3)
C21 C22 C23 121.6(3)
C22 C23 C18 117.6(3)
C22 C23 C17 120.8(3)
C18 C23 C17 121.6(3)
O4 C24 O5 124.8(3)
O4 C24 C16 125.5(3)
O5 C24 C16 109.6(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.228(4)
O2 C8 1.237(3)
O3 C15 1.239(3)
O4 C24 1.192(3)
O5 C24 1.339(3)
O5 C25 1.449(4)
O6 C20 1.376(3)
N1 C7 1.345(4)
N1 C3 1.491(4)
N1 C6 1.491(4)
N2 C15 1.339(4)
N2 C16 1.448(4)
C1 C3 1.519(4)
C2 C3 1.516(5)
C4 C6 1.519(5)
C5 C6 1.524(5)
C7 C8 1.510(4)
C8 C9 1.491(4)
C9 C10 1.386(4)
C9 C14 1.395(5)
C10 C11 1.378(4)
C11 C12 1.382(4)
C12 C13 1.400(4)
C12 C15 1.492(4)
C13 C14 1.380(4)
C16 C24 1.530(4)
C16 C17 1.533(4)
C17 C23 1.518(4)
C18 C19 1.375(4)
C18 C23 1.389(4)
C19 C20 1.386(4)
C20 C21 1.380(4)
C21 C22 1.379(4)
C22 C23 1.382(4)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H6 O3 0.84 1.96 2.779(3) 164.4 2_647
N2 H2N O1 0.87 2.03 2.879(3) 165.4 1_545
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
C7 N1 C3 C2 -64.0(4)
C6 N1 C3 C2 109.5(3)
C7 N1 C3 C1 62.6(4)
C6 N1 C3 C1 -123.9(3)
C7 N1 C6 C4 -127.5(3)
C3 N1 C6 C4 58.9(4)
C7 N1 C6 C5 106.0(3)
C3 N1 C6 C5 -67.6(4)
C3 N1 C7 O1 -2.0(5)
C6 N1 C7 O1 -175.4(3)
C3 N1 C7 C8 178.2(3)
C6 N1 C7 C8 4.7(4)
O1 C7 C8 O2 93.1(4)
N1 C7 C8 O2 -87.0(4)
O1 C7 C8 C9 -76.1(3)
N1 C7 C8 C9 103.7(3)
O2 C8 C9 C10 170.9(3)
C7 C8 C9 C10 -20.1(4)
O2 C8 C9 C14 -10.8(5)
C7 C8 C9 C14 158.2(3)
C14 C9 C10 C11 0.2(5)
C8 C9 C10 C11 178.5(3)
C9 C10 C11 C12 1.3(4)
C10 C11 C12 C13 -1.2(4)
C10 C11 C12 C15 -177.1(3)
C11 C12 C13 C14 -0.4(5)
C15 C12 C13 C14 175.5(3)
C12 C13 C14 C9 1.8(5)
C10 C9 C14 C13 -1.7(5)
C8 C9 C14 C13 180.0(3)
C16 N2 C15 O3 1.5(4)
C16 N2 C15 C12 -176.1(2)
C11 C12 C15 O3 36.5(4)
C13 C12 C15 O3 -139.4(3)
C11 C12 C15 N2 -145.9(3)
C13 C12 C15 N2 38.2(4)
C15 N2 C16 C24 -79.7(3)
C15 N2 C16 C17 160.2(2)
N2 C16 C17 C23 -65.6(3)
C24 C16 C17 C23 173.2(2)
C23 C18 C19 C20 -1.8(5)
C18 C19 C20 O6 -178.6(3)
C18 C19 C20 C21 2.2(5)
O6 C20 C21 C22 179.6(3)
C19 C20 C21 C22 -1.2(5)
C20 C21 C22 C23 -0.2(5)
C21 C22 C23 C18 0.6(5)
C21 C22 C23 C17 -177.2(3)
C19 C18 C23 C22 0.4(5)
C19 C18 C23 C17 178.1(3)
C16 C17 C23 C22 -97.4(3)
C16 C17 C23 C18 85.0(3)
C25 O5 C24 O4 -3.8(5)
C25 O5 C24 C16 172.8(3)
N2 C16 C24 O4 -30.1(4)
C17 C16 C24 O4 91.2(4)
N2 C16 C24 O5 153.3(2)
C17 C16 C24 O5 -85.3(3)
