#------------------------------------------------------------------------------
#$Date: 2018-09-10 03:17:53 +0300 (Mon, 10 Sep 2018) $
#$Revision: 210710 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/36/7103691.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_7103691
loop_
_publ_author_name
Nancy
'Ghosh, Soma'
'Singh, Nishan'
'Kaur Nanda, Gurmeet'
'Venugopalan, P.'
'Bharatam, Prasad V.'
'Trehan, Sanjay'
_publ_section_title
;
 Origin of 1,3-induction in the addition of alkyl lithium to imines
 bearing an N-stereogenic center
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   12
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              1420
_journal_page_last               1421
_journal_paper_doi               10.1039/b300478c
_journal_year                    2003
_chemical_formula_sum            'C25 H28 N2 O4'
_chemical_formula_weight         420.49
_chemical_melting_point          488
_chemical_name_common
;
N-(1'-phenethyl)2-methyl-1-phenylpropylamine-p-nitro benzoate salt
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'Manual edit of SHELXL-97 CIF'
_cell_angle_alpha                117.720(10)
_cell_angle_beta                 101.030(10)
_cell_angle_gamma                96.190(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6310(10)
_cell_length_b                   12.435(2)
_cell_length_c                   12.704(2)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.539
_cell_measurement_theta_min      9.882
_cell_volume                     1153.9(3)
_computing_cell_refinement       'XSCANS (Siemens)'
_computing_data_collection       'XSCANS (Siemens)'
_computing_data_reduction        'XSCANS (Siemens)'
_computing_molecular_graphics    'XP (Siemens)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       2θ/θ
_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    0.0253
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3692
_diffrn_reflns_theta_full        24.00
_diffrn_reflns_theta_max         24.00
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'elongated plate'
_exptl_crystal_F_000             448
_exptl_crystal_preparation       Ethanol
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0428
_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)+(0.0598P)²+0.2281P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1230
_reflns_number_gt                2730
_reflns_number_total             3418
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b300478c.txt
_cod_data_source_block           nancy6
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' 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-1
_cod_database_code               7103691
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.50337(18) 1.86846(13) 1.25596(13) 0.0676(4) Uani 1 1 d . . .
O2 O 0.64624(19) 1.83319(14) 1.39651(12) 0.0722(4) Uani 1 1 d . . .
O3 O 0.7683(3) 1.41235(17) 0.81121(18) 0.1077(7) Uani 1 1 d . . .
O4 O 0.8754(2) 1.36071(16) 0.94354(19) 0.0972(6) Uani 1 1 d . . .
N1 N 0.58380(17) 0.91356(13) 0.62180(12) 0.0431(4) Uani 1 1 d . . .
H1A H 0.6196 0.9022 0.5561 0.052 Uiso 1 1 calc R . .
H1C H 0.5482 0.9846 0.6485 0.052 Uiso 1 1 calc R . .
N2 N 0.8010(2) 1.42539(17) 0.91416(19) 0.0733(5) Uani 1 1 d . . .
C1 C 0.7259(2) 0.93186(15) 0.72251(15) 0.0425(4) Uani 1 1 d . . .
H1B H 0.6875 0.9567 0.7965 0.051 Uiso 1 1 calc R . .
C2 C 0.7815(2) 0.81269(16) 0.69607(16) 0.0457(4) Uani 1 1 d . . .
C3 C 0.8065(3) 0.73357(19) 0.58388(18) 0.0650(6) Uani 1 1 d . . .
H3A H 0.7885 0.7525 0.5205 0.078 Uiso 1 1 calc R . .
C4 C 0.8584(3) 0.6258(2) 0.5653(2) 0.0862(8) Uani 1 1 d . . .
H4A H 0.8745 0.5726 0.4894 0.103 Uiso 1 1 calc R . .
C5 C 0.8858(3) 0.5975(2) 0.6581(3) 0.0866(8) Uani 1 1 d . . .
H5A H 0.9200 0.5250 0.6449 0.104 Uiso 1 1 calc R . .
C6 C 0.8632(3) 0.6750(2) 0.7700(2) 0.0762(7) Uani 1 1 d . . .
H6A H 0.8835 0.6563 0.8335 0.091 Uiso 1 1 calc R . .
C7 C 0.8100(2) 0.78135(19) 0.78816(19) 0.0576(5) Uani 1 1 d . . .
H7A H 0.7928 0.8332 0.8641 0.069 Uiso 1 1 calc R . .
C8 C 0.8590(2) 1.04318(17) 0.75292(17) 0.0540(5) Uani 1 1 d . . .
H8A H 0.8062 1.1115 0.7608 0.065 Uiso 1 1 calc R . .
C9 C 0.9498(3) 1.0191(2) 0.6553(2) 0.0786(7) Uani 1 1 d . . .
H9A H 1.0195 1.0957 0.6761 0.118 Uiso 1 1 calc R . .
H9B H 0.8734 0.9867 0.5761 0.118 Uiso 1 1 calc R . .
H9C H 1.0137 0.9596 0.6522 0.118 Uiso 1 1 calc R . .
C10 C 0.9785(3) 1.0876(2) 0.8781(2) 0.0726(6) Uani 1 1 d . . .
H10A H 1.0317 1.0224 0.8739 0.109 Uiso 1 1 calc R . .
H10B H 0.9212 1.1087 0.9402 0.109 Uiso 1 1 calc R . .
H10C H 1.0578 1.1598 0.8988 0.109 Uiso 1 1 calc R . .
C11 C 0.4408(2) 0.80726(17) 0.57805(16) 0.0511(5) Uani 1 1 d . . .
H11A H 0.4705 0.7296 0.5260 0.061 Uiso 1 1 calc R . .
C12 C 0.3975(2) 0.79770(19) 0.68332(18) 0.0549(5) Uani 1 1 d . . .
C13 C 0.3564(3) 0.8945(2) 0.7772(2) 0.0692(6) Uani 1 1 d . . .
H13A H 0.3567 0.9693 0.7771 0.083 Uiso 1 1 calc R . .
C14 C 0.3149(3) 0.8812(3) 0.8711(3) 0.0894(8) Uani 1 1 d . . .
H14A H 0.2895 0.9475 0.9345 0.107 Uiso 1 1 calc R . .
C15 C 0.3111(3) 0.7709(4) 0.8709(3) 0.1025(10) Uani 1 1 d . . .
H15A H 0.2819 0.7618 0.9335 0.123 Uiso 1 1 calc R . .
C16 C 0.3502(3) 0.6744(3) 0.7789(3) 0.1000(10) Uani 1 1 d . . .
H16A H 0.3475 0.5995 0.7791 0.120 Uiso 1 1 calc R . .
C17 C 0.3941(3) 0.6868(2) 0.6850(3) 0.0770(7) Uani 1 1 d . . .
H17A H 0.4213 0.6204 0.6229 0.092 Uiso 1 1 calc R . .
C18 C 0.3011(3) 0.8233(2) 0.49688(19) 0.0666(6) Uani 1 1 d . . .
H18A H 0.2100 0.7545 0.4642 0.100 Uiso 1 1 calc R . .
H18B H 0.3343 0.8257 0.4299 0.100 Uiso 1 1 calc R . .
H18C H 0.2709 0.8997 0.5453 0.100 Uiso 1 1 calc R . .
C19 C 0.6515(2) 1.71238(15) 1.19006(15) 0.0421(4) Uani 1 1 d . . .
C20 C 0.7512(2) 1.64433(18) 1.21924(17) 0.0541(5) Uani 1 1 d . . .
H20A H 0.7847 1.6619 1.3007 0.065 Uiso 1 1 calc R . .
C21 C 0.8014(3) 1.55129(19) 1.12967(19) 0.0592(5) Uani 1 1 d . . .
H21A H 0.8683 1.5059 1.1498 0.071 Uiso 1 1 calc R . .
C22 C 0.7506(2) 1.52708(16) 1.01062(17) 0.0526(5) Uani 1 1 d . . .
C23 C 0.6543(2) 1.59304(18) 0.97796(17) 0.0568(5) Uani 1 1 d . . .
H23A H 0.6227 1.5756 0.8964 0.068 Uiso 1 1 calc R . .
C24 C 0.6045(2) 1.68676(17) 1.06929(16) 0.0507(5) Uani 1 1 d . . .
H24A H 0.5390 1.7326 1.0488 0.061 Uiso 1 1 calc R . .
C25 C 0.5955(2) 1.81321(16) 1.28968(16) 0.0469(4) 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'
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
C1 N1 C11 117.31(13) . . ?
O3 N2 O4 124.2(2) . . ?
O3 N2 C22 117.9(2) . . ?
O4 N2 C22 117.9(2) . . ?
N1 C1 C2 112.87(13) . . ?
N1 C1 C8 109.41(14) . . ?
C2 C1 C8 115.29(14) . . ?
C3 C2 C7 118.10(17) . . ?
C3 C2 C1 122.89(16) . . ?
C7 C2 C1 119.01(16) . . ?
C2 C3 C4 120.2(2) . . ?
C5 C4 C3 120.3(2) . . ?
C6 C5 C4 120.4(2) . . ?
C5 C6 C7 119.4(2) . . ?
C6 C7 C2 121.5(2) . . ?
C9 C8 C10 110.03(18) . . ?
C9 C8 C1 115.05(16) . . ?
C10 C8 C1 109.71(16) . . ?
C12 C11 N1 112.56(14) . . ?
C12 C11 C18 113.22(16) . . ?
N1 C11 C18 107.66(15) . . ?
C13 C12 C17 118.4(2) . . ?
C13 C12 C11 122.51(18) . . ?
C17 C12 C11 119.07(19) . . ?
C14 C13 C12 120.7(2) . . ?
C15 C14 C13 120.1(3) . . ?
C16 C15 C14 120.0(3) . . ?
C15 C16 C17 120.6(3) . . ?
C12 C17 C16 120.2(3) . . ?
C24 C19 C20 118.88(16) . . ?
C24 C19 C25 120.80(16) . . ?
C20 C19 C25 120.32(16) . . ?
C21 C20 C19 121.11(18) . . ?
C22 C21 C20 118.47(18) . . ?
C21 C22 C23 122.41(17) . . ?
C21 C22 N2 118.50(19) . . ?
C23 C22 N2 119.09(19) . . ?
C22 C23 C24 118.53(17) . . ?
C19 C24 C23 120.58(18) . . ?
O2 C25 O1 126.29(16) . . ?
O2 C25 C19 117.08(16) . . ?
O1 C25 C19 116.62(16) . . ?
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 C25 1.245(2) . ?
O2 C25 1.237(2) . ?
O3 N2 1.212(3) . ?
O4 N2 1.224(3) . ?
N1 C1 1.504(2) . ?
N1 C11 1.511(2) . ?
N2 C22 1.473(2) . ?
C1 C2 1.514(2) . ?
C1 C8 1.541(3) . ?
C2 C3 1.380(3) . ?
C2 C7 1.384(3) . ?
C3 C4 1.389(3) . ?
C4 C5 1.366(4) . ?
C5 C6 1.363(3) . ?
C6 C7 1.378(3) . ?
C8 C9 1.523(3) . ?
C8 C10 1.526(3) . ?
C11 C12 1.507(3) . ?
C11 C18 1.525(3) . ?
C12 C13 1.384(3) . ?
C12 C17 1.387(3) . ?
C13 C14 1.383(3) . ?
C14 C15 1.368(4) . ?
C15 C16 1.361(4) . ?
C16 C17 1.387(4) . ?
C19 C24 1.378(2) . ?
C19 C20 1.386(2) . ?
C19 C25 1.515(2) . ?
C20 C21 1.376(3) . ?
C21 C22 1.365(3) . ?
C22 C23 1.367(3) . ?
C23 C24 1.389(3) . ?
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
C11 N1 C1 C2 49.56(19) . . . . ?
C11 N1 C1 C8 179.37(14) . . . . ?
N1 C1 C2 C3 47.8(2) . . . . ?
C8 C1 C2 C3 -78.9(2) . . . . ?
N1 C1 C2 C7 -132.66(17) . . . . ?
C8 C1 C2 C7 100.6(2) . . . . ?
C7 C2 C3 C4 0.2(3) . . . . ?
C1 C2 C3 C4 179.7(2) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C4 C5 C6 C7 1.0(4) . . . . ?
C5 C6 C7 C2 -1.2(3) . . . . ?
C3 C2 C7 C6 0.6(3) . . . . ?
C1 C2 C7 C6 -178.96(19) . . . . ?
N1 C1 C8 C9 -72.5(2) . . . . ?
C2 C1 C8 C9 56.0(2) . . . . ?
N1 C1 C8 C10 162.79(15) . . . . ?
C2 C1 C8 C10 -68.7(2) . . . . ?
C1 N1 C11 C12 43.1(2) . . . . ?
C1 N1 C11 C18 168.61(14) . . . . ?
N1 C11 C12 C13 58.6(2) . . . . ?
C18 C11 C12 C13 -63.8(2) . . . . ?
N1 C11 C12 C17 -123.31(19) . . . . ?
C18 C11 C12 C17 114.3(2) . . . . ?
C17 C12 C13 C14 0.8(3) . . . . ?
C11 C12 C13 C14 178.9(2) . . . . ?
C12 C13 C14 C15 -1.2(4) . . . . ?
C13 C14 C15 C16 0.8(4) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
C13 C12 C17 C16 0.0(3) . . . . ?
C11 C12 C17 C16 -178.2(2) . . . . ?
C15 C16 C17 C12 -0.4(4) . . . . ?
C24 C19 C20 C21 -0.9(3) . . . . ?
C25 C19 C20 C21 179.12(17) . . . . ?
C19 C20 C21 C22 0.0(3) . . . . ?
C20 C21 C22 C23 1.0(3) . . . . ?
C20 C21 C22 N2 -178.50(17) . . . . ?
O3 N2 C22 C21 -173.2(2) . . . . ?
O4 N2 C22 C21 5.7(3) . . . . ?
O3 N2 C22 C23 7.3(3) . . . . ?
O4 N2 C22 C23 -173.83(19) . . . . ?
C21 C22 C23 C24 -1.0(3) . . . . ?
N2 C22 C23 C24 178.53(16) . . . . ?
C20 C19 C24 C23 1.0(3) . . . . ?
C25 C19 C24 C23 -179.09(16) . . . . ?
C22 C23 C24 C19 0.0(3) . . . . ?
C24 C19 C25 O2 -178.06(17) . . . . ?
C20 C19 C25 O2 1.9(3) . . . . ?
C24 C19 C25 O1 1.6(3) . . . . ?
C20 C19 C25 O1 -178.48(17) . . . . ?
