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#$Date: 2016-03-21 03:49:17 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178446 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/67/4026734.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_4026734
loop_
_publ_author_name
'Avital Steinberg'
'Mark Froimowitz'
'Damon A. Parrish'
'Jeffrey R. Deschamps'
'Robert Glaser'
_publ_contact_author_address
;
Laboratory for the Structure of Matter
Naval Research Laboratory
Washington, DC 20375
;
_publ_contact_author_email       dparrish@ccs.nrl.navy.mil
_publ_contact_author_fax         202-767-6874
_publ_contact_author_name        'Dr Damon A. Parrish'
_publ_contact_author_phone       202-404-2141
_publ_section_title
;
 Solution- and Solid-State Conformations of C(α)-Alkyl Analogues of
 Methylphenidate (Ritalin) Salts: Avoidance of gauche+gauche- Interactions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9239
_journal_page_last               9245
_journal_paper_doi               10.1021/jo201415h
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C17 H26 Cl3 N'
_chemical_formula_weight         350.74
_chemical_name_systematic
; 
 (RS,RS)-2-(1-(3,4-dichlorophenyl)-3-methylbutyl)-1-methylpiperidinium chloride 
;
_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_date             2005-03-30
_audit_creation_method
'from SHELXL97 CIF, local template and enCIFer'
_cell_angle_alpha                90.00
_cell_angle_beta                 112.514(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.720(5)
_cell_length_b                   11.077(4)
_cell_length_c                   13.974(6)
_cell_measurement_temperature    103(2)
_cell_volume                     1818.9(13)
_computing_cell_refinement       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_collection       'Bruker SMART v5.631 (Bruker, 2001)'
_computing_data_reduction
;
Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001)
;
_computing_molecular_graphics    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_publication_material  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_refinement  'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_computing_structure_solution    'Bruker SHELXTL v6.14 (Bruker, 2000b)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0528
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14733
_diffrn_reflns_theta_full        28.29
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    0.498
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Bruker, 2000c)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_refine_diff_density_max         1.962
_refine_diff_density_min         -0.690
_refine_diff_density_rms         0.096
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         4402
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0610
_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)+(0.0794P)²+4.1490P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1757
_reflns_number_gt                3117
_reflns_number_total             4402
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo201415h_si_004.cif
_cod_data_source_block           mark160
_cod_database_code               4026734
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 0.4149(2) 0.3460(2) 0.3447(2) 0.0167(5) Uani 1 1 d .
H1D H 0.4060 0.4242 0.3645 0.020 Uiso 1 1 calc R
C1 C 0.3293(3) 0.3310(3) 0.2370(3) 0.0227(7) Uiso 1 1 d .
H1A H 0.3463 0.3874 0.1908 0.034 Uiso 1 1 calc R
H1B H 0.2531 0.3477 0.2356 0.034 Uiso 1 1 calc R
H1C H 0.3321 0.2481 0.2137 0.034 Uiso 1 1 calc R
C2 C 0.3976(3) 0.2633(3) 0.4236(2) 0.0158(6) Uani 1 1 d .
H2A H 0.4538 0.2871 0.4935 0.019 Uiso 1 1 calc R
C3 C 0.4242(3) 0.1335(3) 0.4032(3) 0.0201(7) Uani 1 1 d .
H3A H 0.3687 0.1072 0.3349 0.024 Uiso 1 1 calc R
H3B H 0.4161 0.0798 0.4566 0.024 Uiso 1 1 calc R
C4 C 0.5453(3) 0.1216(3) 0.4049(3) 0.0255(7) Uani 1 1 d .
H4A H 0.6012 0.1375 0.4759 0.031 Uiso 1 1 calc R
H4B H 0.5572 0.0382 0.3859 0.031 Uiso 1 1 calc R
C5 C 0.5647(3) 0.2099(3) 0.3299(3) 0.0277(8) Uani 1 1 d .
H5A H 0.6454 0.2065 0.3376 0.033 Uiso 1 1 calc R
H5B H 0.5167 0.1869 0.2579 0.033 Uiso 1 1 calc R
C6 C 0.5354(3) 0.3375(3) 0.3510(3) 0.0263(8) Uani 1 1 d .
H6A H 0.5882 0.3627 0.4209 0.032 Uiso 1 1 calc R
H6B H 0.5456 0.3933 0.2999 0.032 Uiso 1 1 calc R
C7 C 0.2778(3) 0.2809(2) 0.4240(2) 0.0143(6) Uani 1 1 d .
H7A H 0.2205 0.2628 0.3531 0.017 Uiso 1 1 calc R
C8 C 0.2618(3) 0.4125(3) 0.4508(3) 0.0177(6) Uani 1 1 d .
H8A H 0.3210 0.4315 0.5196 0.021 Uiso 1 1 calc R
H8B H 0.2747 0.4659 0.3996 0.021 Uiso 1 1 calc R
C9 C 0.1457(3) 0.4427(3) 0.4532(3) 0.0222(7) Uani 1 1 d .
H9A H 0.1336 0.3904 0.5064 0.027 Uiso 1 1 calc R
C9B C 0.1447(3) 0.5746(3) 0.4851(3) 0.0289(8) Uani 1 1 d .
H9BA H 0.2073 0.5885 0.5519 0.043 Uiso 1 1 calc R
H9BB H 0.0721 0.5926 0.4913 0.043 Uiso 1 1 calc R
H9BC H 0.1540 0.6273 0.4325 0.043 Uiso 1 1 calc R
C9A C 0.0500(3) 0.4198(4) 0.3500(3) 0.0404(10) Uani 1 1 d .
H9AA H 0.0516 0.3352 0.3302 0.061 Uiso 1 1 calc R
H9AB H 0.0592 0.4723 0.2973 0.061 Uiso 1 1 calc R
H9AC H -0.0230 0.4371 0.3556 0.061 Uiso 1 1 calc R
C1' C 0.2589(3) 0.1945(3) 0.5003(2) 0.0163(6) Uani 1 1 d .
C2' C 0.1898(3) 0.0937(3) 0.4632(3) 0.0193(6) Uani 1 1 d .
H2'A H 0.1555 0.0783 0.3909 0.023 Uiso 1 1 calc R
C3' C 0.1715(3) 0.0153(3) 0.5337(3) 0.0240(7) Uani 1 1 d .
C4' C 0.2166(3) 0.0400(3) 0.6381(3) 0.0249(7) Uani 1 1 d .
C5' C 0.2850(3) 0.1402(3) 0.6753(3) 0.0253(7) Uani 1 1 d .
H5'A H 0.3157 0.1575 0.7473 0.030 Uiso 1 1 calc R
C6' C 0.3083(3) 0.2148(3) 0.6070(3) 0.0216(7) Uani 1 1 d .
H6'A H 0.3588 0.2810 0.6329 0.026 Uiso 1 1 calc R
Cl3' Cl 0.09118(9) -0.11346(7) 0.48728(8) 0.0353(3) Uani 1 1 d .
Cl4' Cl 0.19035(10) -0.05336(8) 0.72641(8) 0.0394(3) Uani 1 1 d .
Cl Cl 0.40673(7) 0.61924(6) 0.33159(6) 0.0215(2) 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'
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 C6 112.8(3)
C1 N1 C2 114.5(2)
C6 N1 C2 110.4(2)
C1 N1 H1D 106.2
C6 N1 H1D 106.2
C2 N1 H1D 106.2
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 C3 109.2(2)
N1 C2 C7 110.3(2)
C3 C2 C7 114.2(2)
N1 C2 H2A 107.6
C3 C2 H2A 107.6
C7 C2 H2A 107.6
C2 C3 C4 111.7(3)
C2 C3 H3A 109.3
C4 C3 H3A 109.3
C2 C3 H3B 109.3
C4 C3 H3B 109.3
H3A C3 H3B 107.9
C5 C4 C3 111.1(3)
C5 C4 H4A 109.4
C3 C4 H4A 109.4
C5 C4 H4B 109.4
C3 C4 H4B 109.4
H4A C4 H4B 108.0
C6 C5 C4 110.3(3)
C6 C5 H5A 109.6
C4 C5 H5A 109.6
C6 C5 H5B 109.6
C4 C5 H5B 109.6
H5A C5 H5B 108.1
N1 C6 C5 111.6(3)
N1 C6 H6A 109.3
C5 C6 H6A 109.3
N1 C6 H6B 109.3
C5 C6 H6B 109.3
H6A C6 H6B 108.0
C1' C7 C8 110.8(3)
C1' C7 C2 110.2(2)
C8 C7 C2 110.1(2)
C1' C7 H7A 108.5
C8 C7 H7A 108.5
C2 C7 H7A 108.5
C9 C8 C7 115.6(2)
C9 C8 H8A 108.4
C7 C8 H8A 108.4
C9 C8 H8B 108.4
C7 C8 H8B 108.4
H8A C8 H8B 107.5
C9A C9 C8 112.1(3)
C9A C9 C9B 110.1(3)
C8 C9 C9B 109.4(3)
C9A C9 H9A 108.4
C8 C9 H9A 108.4
C9B C9 H9A 108.4
C9 C9B H9BA 109.5
C9 C9B H9BB 109.5
H9BA C9B H9BB 109.5
C9 C9B H9BC 109.5
H9BA C9B H9BC 109.5
H9BB C9B H9BC 109.5
C9 C9A H9AA 109.5
C9 C9A H9AB 109.5
H9AA C9A H9AB 109.5
C9 C9A H9AC 109.5
H9AA C9A H9AC 109.5
H9AB C9A H9AC 109.5
C2' C1' C6' 119.2(3)
C2' C1' C7 119.4(3)
C6' C1' C7 121.4(3)
C1' C2' C3' 119.2(3)
C1' C2' H2'A 120.4
C3' C2' H2'A 120.4
C4' C3' C2' 120.6(3)
C4' C3' Cl3' 120.6(3)
C2' C3' Cl3' 118.8(3)
C3' C4' C5' 120.3(3)
C3' C4' Cl4' 121.3(3)
C5' C4' Cl4' 118.4(3)
C6' C5' C4' 119.5(3)
C6' C5' H5'A 120.2
C4' C5' H5'A 120.2
C5' C6' C1' 121.0(3)
C5' C6' H6'A 119.5
C1' C6' H6'A 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.492(4)
N1 C6 1.504(4)
N1 C2 1.513(4)
N1 H1D 0.9300
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C3 1.529(4)
C2 C7 1.539(4)
C2 H2A 1.0000
C3 C4 1.537(5)
C3 H3A 0.9900
C3 H3B 0.9900
C4 C5 1.522(5)
C4 H4A 0.9900
C4 H4B 0.9900
C5 C6 1.519(5)
C5 H5A 0.9900
C5 H5B 0.9900
C6 H6A 0.9900
C6 H6B 0.9900
C7 C1' 1.519(4)
C7 C8 1.538(4)
C7 H7A 1.0000
C8 C9 1.526(4)
C8 H8A 0.9900
C8 H8B 0.9900
C9 C9A 1.511(5)
C9 C9B 1.529(4)
C9 H9A 1.0000
C9B H9BA 0.9800
C9B H9BB 0.9800
C9B H9BC 0.9800
C9A H9AA 0.9800
C9A H9AB 0.9800
C9A H9AC 0.9800
C1' C2' 1.392(4)
C1' C6' 1.398(5)
C2' C3' 1.398(5)
C2' H2'A 0.9500
C3' C4' 1.376(5)
C3' Cl3' 1.729(3)
C4' C5' 1.383(5)
C4' Cl4' 1.737(3)
C5' C6' 1.377(5)
C5' H5'A 0.9500
C6' H6'A 0.9500
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
N1 H1D Cl 0.93 2.21 3.032(3) 147.0 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
C1 N1 C2 C3 69.6(3)
C6 N1 C2 C3 -59.0(3)
C1 N1 C2 C7 -56.7(3)
C6 N1 C2 C7 174.7(2)
N1 C2 C3 C4 56.6(3)
C7 C2 C3 C4 -179.4(3)
C2 C3 C4 C5 -54.5(4)
C3 C4 C5 C6 53.4(4)
C1 N1 C6 C5 -69.3(4)
C2 N1 C6 C5 60.1(4)
C4 C5 C6 N1 -56.8(4)
N1 C2 C7 C1' 177.8(2)
C3 C2 C7 C1' 54.4(3)
N1 C2 C7 C8 -59.6(3)
C3 C2 C7 C8 177.0(3)
C1' C7 C8 C9 -58.1(4)
C2 C7 C8 C9 179.6(3)
C7 C8 C9 C9A -59.8(4)
C7 C8 C9 C9B 177.7(3)
C8 C7 C1' C2' 132.8(3)
C2 C7 C1' C2' -105.1(3)
C8 C7 C1' C6' -46.4(4)
C2 C7 C1' C6' 75.7(3)
C6' C1' C2' C3' 0.1(4)
C7 C1' C2' C3' -179.1(3)
C1' C2' C3' C4' 3.0(5)
C1' C2' C3' Cl3' -176.9(2)
C2' C3' C4' C5' -2.9(5)
Cl3' C3' C4' C5' 177.0(3)
C2' C3' C4' Cl4' 177.6(3)
Cl3' C3' C4' Cl4' -2.5(4)
C3' C4' C5' C6' -0.4(5)
Cl4' C4' C5' C6' 179.1(3)
C4' C5' C6' C1' 3.5(5)
C2' C1' C6' C5' -3.4(5)
C7 C1' C6' C5' 175.8(3)
