#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:04:14 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178932 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/61/4116101.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_4116101
loop_
_publ_author_name
'Jari T. Kovalainen'
'Johannes A. M. Christiaans'
'Risto Ropponen'
'Antti Poso'
'Mikael Peräkylä'
'Jouko Vepsäläinen'
'Reino Laatikainen'
'Jukka Gynther'
_publ_contact_author             'Kovalainen, Jari'
_publ_contact_author_email       kovalain@mail.uku.fi
_publ_section_title
;
 A Proton Relay Process as the Mechanism of Activation of the Histamine
 H3-Receptor Determined by 1H NMR and ab Initio Quantum Mechanical
 Calculations
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6989
_journal_page_last               6996
_journal_paper_doi               10.1021/ja993322f
_journal_volume                  122
_journal_year                    2000
_chemical_formula_sum            'C13 H25 Cl2 N3 O'
_chemical_formula_weight         310.26
_chemical_name_systematic
;
2(S)-amino-3-(1H-imidazol-4(5)-yl)propyl cyclohexylmethyl ether dihydrochloride
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.827(1)
_cell_length_b                   12.774(1)
_cell_length_c                   17.353(1)
_cell_measurement_temperature    173(2)
_cell_volume                     1735.0(3)
_computing_cell_refinement       Denzo
_computing_data_collection       Collect
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_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  0.070
_diffrn_reflns_av_sigmaI/netI    0.0883
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            27791
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.372
_exptl_absorpt_correction_T_max  0.9638
_exptl_absorpt_correction_T_min  0.9128
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.13(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         4088
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0492
_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)+(0.0286P)²+0.0978P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                2914
_reflns_number_total             4088
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja993322f_1.cif
_cod_data_source_block           8
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' 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               4116101
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
Cl1 Cl -0.31735(7) -0.68426(5) -0.08463(4) 0.03625(17) Uani 1 1 d .
Cl2 Cl -0.87066(8) -0.85419(5) -0.21228(4) 0.04372(19) Uani 1 1 d .
N1 N 0.2369(3) -0.42555(17) -0.25248(12) 0.0360(5) Uani 1 1 d .
H1 H 0.1323 -0.4109 -0.2678 0.043 Uiso 1 1 calc R
C2 C 0.3767(4) -0.3788(2) -0.27776(15) 0.0409(6) Uani 1 1 d .
H2 H 0.3816 -0.3243 -0.3150 0.049 Uiso 1 1 calc R
N3 N 0.5087(3) -0.42158(18) -0.24176(13) 0.0395(6) Uani 1 1 d .
H3 H 0.6164 -0.4044 -0.2488 0.047 Uiso 1 1 calc R
C4 C 0.4510(3) -0.4970(2) -0.19169(15) 0.0372(7) Uani 1 1 d .
H4 H 0.5192 -0.5387 -0.1584 0.045 Uiso 1 1 calc R
C5 C 0.2788(3) -0.5008(2) -0.19864(14) 0.0303(6) Uani 1 1 d .
C6 C 0.1458(3) -0.5690(2) -0.16400(13) 0.0342(6) Uani 1 1 d .
H6A H 0.1124 -0.6234 -0.2018 0.041 Uiso 1 1 calc R
H6B H 0.0433 -0.5265 -0.1522 0.041 Uiso 1 1 calc R
C7 C 0.2087(3) -0.62226(19) -0.08972(14) 0.0302(6) Uani 1 1 d .
H7 H 0.3226 -0.6548 -0.1000 0.036 Uiso 1 1 calc R
C8 C 0.2260(3) -0.5483(2) -0.02241(14) 0.0348(6) Uani 1 1 d .
H8A H 0.2781 -0.5847 0.0221 0.042 Uiso 1 1 calc R
H8B H 0.2995 -0.4882 -0.0365 0.042 Uiso 1 1 calc R
O9 O 0.0609(2) -0.51349(15) -0.00365(11) 0.0429(5) Uani 1 1 d .
C10 C 0.0573(3) -0.4354(2) 0.05531(15) 0.0410(7) Uani 1 1 d .
H10A H 0.1027 -0.3684 0.0351 0.049 Uiso 1 1 calc R
H10B H 0.1292 -0.4575 0.0993 0.049 Uiso 1 1 calc R
C11 C -0.1247(3) -0.4215(2) 0.08111(14) 0.0379(6) Uani 1 1 d .
H11 H -0.1675 -0.4910 0.0991 0.046 Uiso 1 1 calc R
C12 C -0.2409(4) -0.3846(2) 0.01673(17) 0.0457(7) Uani 1 1 d .
H12A H -0.2372 -0.4357 -0.0261 0.055 Uiso 1 1 calc R
H12B H -0.1994 -0.3165 -0.0031 0.055 Uiso 1 1 calc R
C13 C -0.4250(4) -0.3727(3) 0.04480(19) 0.0548(8) Uani 1 1 d .
H13A H -0.4958 -0.3439 0.0026 0.066 Uiso 1 1 calc R
H13B H -0.4710 -0.4425 0.0584 0.066 Uiso 1 1 calc R
C14 C -0.4378(4) -0.3010(3) 0.11466(18) 0.0569(9) Uani 1 1 d .
H14A H -0.4074 -0.2286 0.0995 0.068 Uiso 1 1 calc R
H14B H -0.5568 -0.3005 0.1340 0.068 Uiso 1 1 calc R
C15 C -0.3192(4) -0.3376(2) 0.17783(16) 0.0502(8) Uani 1 1 d .
H15A H -0.3570 -0.4071 0.1965 0.060 Uiso 1 1 calc R
H15B H -0.3247 -0.2880 0.2216 0.060 Uiso 1 1 calc R
C16 C -0.1357(4) -0.3451(2) 0.14913(15) 0.0440(7) Uani 1 1 d .
H16A H -0.0609 -0.3697 0.1914 0.053 Uiso 1 1 calc R
H16B H -0.0956 -0.2751 0.1328 0.053 Uiso 1 1 calc R
N17 N 0.0848(2) -0.70694(16) -0.06964(12) 0.0320(5) Uani 1 1 d .
H17A H -0.0223 -0.6795 -0.0665 0.048 Uiso 1 1 calc R
H17B H 0.1139 -0.7355 -0.0234 0.048 Uiso 1 1 calc R
H17C H 0.0873 -0.7573 -0.1067 0.048 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'
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
C2 N1 C5 110.0(2)
N1 C2 N3 107.6(2)
C2 N3 C4 109.4(2)
C5 C4 N3 107.2(2)
C4 C5 N1 105.8(2)
C4 C5 C6 133.1(2)
N1 C5 C6 121.0(2)
C5 C6 C7 111.98(19)
N17 C7 C8 109.36(19)
N17 C7 C6 107.94(18)
C8 C7 C6 113.6(2)
O9 C8 C7 107.14(19)
C8 O9 C10 113.85(19)
O9 C10 C11 108.3(2)
C10 C11 C12 112.7(2)
C10 C11 C16 111.0(2)
C12 C11 C16 109.7(2)
C11 C12 C13 111.2(2)
C14 C13 C12 112.0(2)
C15 C14 C13 110.6(2)
C14 C15 C16 111.2(2)
C15 C16 C11 110.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.322(3)
N1 C5 1.380(3)
C2 N3 1.326(3)
N3 C4 1.373(3)
C4 C5 1.354(3)
C5 C6 1.485(3)
C6 C7 1.538(3)
C7 N17 1.494(3)
C7 C8 1.509(3)
C8 O9 1.405(3)
O9 C10 1.429(3)
C10 C11 1.504(4)
C11 C12 1.515(4)
C11 C16 1.533(3)
C12 C13 1.529(4)
C13 C14 1.523(4)
C14 C15 1.510(4)
C15 C16 1.523(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
N1 H1 Cl2 0.88 2.20 3.069(2) 169.4 4_454
N3 H3 Cl2 0.88 2.20 3.067(2) 169.6 4_554
N17 H17A Cl1 0.91 2.33 3.1715(18) 153.5 .
N17 H17B Cl1 0.91 2.20 3.112(2) 176.0 3_535
N17 H17C Cl2 0.91 2.24 3.128(2) 166.9 1_655
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
C5 N1 C2 N3 0.0(3)
N1 C2 N3 C4 -0.6(3)
C2 N3 C4 C5 0.9(3)
N3 C4 C5 N1 -0.9(3)
N3 C4 C5 C6 175.9(3)
C2 N1 C5 C4 0.6(3)
C2 N1 C5 C6 -176.7(2)
C4 C5 C6 C7 20.9(4)
N1 C5 C6 C7 -162.7(2)
C5 C6 C7 N17 -166.9(2)
C5 C6 C7 C8 71.7(3)
N17 C7 C8 O9 -54.8(3)
C6 C7 C8 O9 65.9(3)
C7 C8 O9 C10 -175.0(2)
C8 O9 C10 C11 -168.5(2)
O9 C10 C11 C12 -61.3(3)
O9 C10 C11 C16 175.3(2)
C10 C11 C12 C13 179.3(2)
C16 C11 C12 C13 -56.6(3)
C11 C12 C13 C14 54.9(3)
C12 C13 C14 C15 -54.0(4)
C13 C14 C15 C16 56.1(3)
C14 C15 C16 C11 -58.9(3)
C10 C11 C16 C15 -176.3(2)
C12 C11 C16 C15 58.6(3)
