#------------------------------------------------------------------------------
#$Date: 2018-09-10 03:17:53 +0300 (Mon, 10 Sep 2018) $
#$Revision: 210710 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/37/7113716.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_7113716
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            'C17 H22 Cl N'
_chemical_formula_weight         275.81
_chemical_melting_point          492.0(10)
_chemical_name_common
'N(1'-phenethyl)-1-phenylpropylamine hydrocholride'
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                90.00
_cell_angle_beta                 101.97(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.098(4)
_cell_length_b                   8.006(2)
_cell_length_c                   18.969(9)
_cell_measurement_reflns_used    28
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.812
_cell_measurement_theta_min      10.425
_cell_volume                     1648.8(11)
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '2θ/θ 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  0.0402
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2373
_diffrn_reflns_theta_full        23.01
_diffrn_reflns_theta_max         23.01
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        None
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.220
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_preparation       'ethanol:acetonitrile, 1:1'
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.360
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.009(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2251
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0629
_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)+(0.1046P)²+0.5252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1598
_refine_ls_wR_factor_ref         0.1845
_reflns_number_gt                1510
_reflns_number_total             2251
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7103690
_cod_data_source_file            b300478c.txt
_cod_data_source_block           nan1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '491-493' was changed to '492.0(10)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Monoclinic' changed to
'monoclinic' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7113716
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
N1 N 0.0871(2) 0.8360(4) 0.93368(17) 0.0633(9) Uani 1 1 d .
H1A H 0.0080 0.8316 0.9382 0.076 Uiso 1 1 calc R
H1B H 0.1242 0.9163 0.9637 0.076 Uiso 1 1 calc R
C1 C 0.0889(3) 0.8885(5) 0.8584(2) 0.0727(11) Uani 1 1 d .
H1C H 0.1751 0.9019 0.8546 0.087 Uiso 1 1 calc R
C2 C 0.0263(5) 1.0607(6) 0.8464(3) 0.0973(15) Uani 1 1 d .
H2A H -0.0602 1.0476 0.8473 0.117 Uiso 1 1 calc R
H2B H 0.0624 1.1331 0.8862 0.117 Uiso 1 1 calc R
C3 C 0.0354(8) 1.1379(9) 0.7830(5) 0.173(3) Uani 1 1 d .
H3A H 0.1207 1.1532 0.7816 0.260 Uiso 1 1 calc R
H3B H -0.0047 1.2447 0.7801 0.260 Uiso 1 1 calc R
H3C H -0.0034 1.0699 0.7430 0.260 Uiso 1 1 calc R
C4 C 0.1463(3) 0.6730(4) 0.9587(2) 0.0655(11) Uani 1 1 d .
H4A H 0.0982 0.5846 0.9301 0.079 Uiso 1 1 calc R
C5 C 0.1411(4) 0.6430(6) 1.0374(3) 0.0988(15) Uani 1 1 d .
H5A H 0.1873 0.7282 1.0668 0.148 Uiso 1 1 calc R
H5B H 0.1757 0.5356 1.0522 0.148 Uiso 1 1 calc R
H5C H 0.0570 0.6463 1.0427 0.148 Uiso 1 1 calc R
C6 C 0.2762(3) 0.6636(4) 0.9458(2) 0.0594(9) Uani 1 1 d .
C7 C 0.3637(3) 0.7836(5) 0.9747(2) 0.0726(11) Uani 1 1 d .
H7A H 0.3424 0.8708 1.0022 0.087 Uiso 1 1 calc R
C8 C 0.4823(3) 0.7729(6) 0.9626(3) 0.0815(13) Uani 1 1 d .
H8A H 0.5396 0.8550 0.9808 0.098 Uiso 1 1 calc R
C9 C 0.5156(3) 0.6448(6) 0.9245(2) 0.0763(12) Uani 1 1 d .
H9A H 0.5955 0.6387 0.9168 0.092 Uiso 1 1 calc R
C10 C 0.4325(4) 0.5254(6) 0.8977(2) 0.0796(12) Uani 1 1 d .
H10A H 0.4561 0.4361 0.8722 0.095 Uiso 1 1 calc R
C11 C 0.3121(3) 0.5346(5) 0.9077(2) 0.0715(11) Uani 1 1 d .
H11A H 0.2556 0.4525 0.8883 0.086 Uiso 1 1 calc R
C12 C 0.0301(3) 0.7619(5) 0.8028(2) 0.0739(11) Uani 1 1 d .
C13 C 0.0967(5) 0.6958(6) 0.7558(3) 0.0939(14) Uani 1 1 d .
H13A H 0.1793 0.7240 0.7606 0.113 Uiso 1 1 calc R
C14 C 0.0428(7) 0.5892(8) 0.7021(3) 0.1184(19) Uani 1 1 d .
H14A H 0.0885 0.5479 0.6700 0.142 Uiso 1 1 calc R
C15 C -0.0767(8) 0.5432(8) 0.6953(3) 0.127(2) Uani 1 1 d .
H15A H -0.1129 0.4707 0.6587 0.152 Uiso 1 1 calc R
C16 C -0.1424(6) 0.6031(8) 0.7417(4) 0.128(2) Uani 1 1 d .
H16A H -0.2243 0.5714 0.7370 0.154 Uiso 1 1 calc R
C17 C -0.0897(4) 0.7117(7) 0.7966(3) 0.1010(15) Uani 1 1 d .
H17A H -0.1357 0.7502 0.8290 0.121 Uiso 1 1 calc R
Cl1 Cl -0.18033(8) 0.85873(14) 0.96453(7) 0.0893(5) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0337(14) 0.069(2) 0.085(2) -0.0181(17) 0.0077(13) -0.0044(13)
C1 0.047(2) 0.075(3) 0.093(3) -0.006(2) 0.0069(19) 0.0061(18)
C2 0.089(3) 0.075(3) 0.124(4) 0.005(3) 0.015(3) 0.014(3)
C3 0.220(9) 0.139(6) 0.183(7) 0.057(5) 0.093(6) 0.058(6)
C4 0.0400(19) 0.061(2) 0.094(3) -0.008(2) 0.0090(18) -0.0058(16)
C5 0.066(3) 0.122(4) 0.119(4) 0.002(3) 0.042(3) -0.015(3)
C6 0.0402(18) 0.059(2) 0.079(2) 0.0006(19) 0.0108(16) 0.0009(16)
C7 0.0392(19) 0.066(2) 0.112(3) -0.014(2) 0.0135(19) -0.0017(18)
C8 0.0381(19) 0.076(3) 0.130(4) 0.003(3) 0.017(2) -0.0044(19)
C9 0.044(2) 0.087(3) 0.101(3) 0.011(3) 0.020(2) 0.012(2)
C10 0.067(3) 0.085(3) 0.089(3) -0.005(2) 0.020(2) 0.021(2)
C11 0.054(2) 0.069(3) 0.087(3) -0.009(2) 0.0041(19) 0.0030(19)
C12 0.059(2) 0.074(3) 0.083(3) -0.002(2) 0.001(2) 0.017(2)
C13 0.090(3) 0.100(3) 0.088(3) -0.005(3) 0.010(3) 0.021(3)
C14 0.139(5) 0.125(5) 0.087(4) -0.009(3) 0.015(4) 0.036(4)
C15 0.147(6) 0.114(5) 0.102(4) -0.029(3) -0.016(4) 0.022(4)
C16 0.090(4) 0.133(5) 0.141(5) -0.042(4) -0.024(4) -0.001(3)
C17 0.061(3) 0.124(4) 0.109(4) -0.039(3) -0.002(2) 0.000(3)
Cl1 0.0355(5) 0.0983(9) 0.1338(10) -0.0454(7) 0.0166(5) -0.0104(5)
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'
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
C1 N1 C4 117.2(3)
N1 C1 C12 113.0(3)
N1 C1 C2 107.4(3)
C12 C1 C2 112.4(3)
C3 C2 C1 114.9(5)
N1 C4 C6 111.3(3)
N1 C4 C5 110.2(3)
C6 C4 C5 112.4(3)
C11 C6 C7 118.2(3)
C11 C6 C4 121.0(3)
C7 C6 C4 120.7(3)
C8 C7 C6 120.0(4)
C9 C8 C7 120.8(4)
C8 C9 C10 119.9(4)
C9 C10 C11 120.7(4)
C6 C11 C10 120.5(4)
C17 C12 C13 118.3(4)
C17 C12 C1 121.9(4)
C13 C12 C1 119.9(4)
C14 C13 C12 120.8(5)
C15 C14 C13 120.5(6)
C16 C15 C14 119.6(6)
C15 C16 C17 120.9(6)
C12 C17 C16 119.9(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.492(5)
N1 C4 1.494(4)
C1 C12 1.511(6)
C1 C2 1.539(6)
C2 C3 1.374(8)
C4 C6 1.513(5)
C4 C5 1.524(6)
C6 C11 1.366(5)
C6 C7 1.395(5)
C7 C8 1.385(5)
C8 C9 1.349(6)
C9 C10 1.353(6)
C10 C11 1.390(5)
C12 C17 1.370(6)
C12 C13 1.376(6)
C13 C14 1.368(8)
C14 C15 1.356(8)
C15 C16 1.343(8)
C16 C17 1.389(7)
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
C4 N1 C1 C12 57.1(4)
C4 N1 C1 C2 -178.4(3)
N1 C1 C2 C3 171.3(5)
C12 C1 C2 C3 -63.8(7)
C1 N1 C4 C6 52.1(4)
C1 N1 C4 C5 177.5(3)
N1 C4 C6 C11 -125.4(4)
C5 C4 C6 C11 110.4(4)
N1 C4 C6 C7 56.9(5)
C5 C4 C6 C7 -67.3(5)
C11 C6 C7 C8 2.0(6)
C4 C6 C7 C8 179.8(4)
C6 C7 C8 C9 -1.8(6)
C7 C8 C9 C10 0.2(7)
C8 C9 C10 C11 1.2(6)
C7 C6 C11 C10 -0.7(6)
C4 C6 C11 C10 -178.5(3)
C9 C10 C11 C6 -0.9(6)
N1 C1 C12 C17 58.2(5)
C2 C1 C12 C17 -63.5(6)
N1 C1 C12 C13 -122.8(4)
C2 C1 C12 C13 115.5(4)
C17 C12 C13 C14 3.2(7)
C1 C12 C13 C14 -175.8(4)
C12 C13 C14 C15 -1.7(8)
C13 C14 C15 C16 0.0(10)
C14 C15 C16 C17 0.1(10)
C13 C12 C17 C16 -3.1(7)
C1 C12 C17 C16 175.9(5)
C15 C16 C17 C12 1.5(9)
