#------------------------------------------------------------------------------
#$Date: 2016-03-24 01:59:59 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179550 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/19/4501949.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_4501949
loop_
_publ_author_name
'Hoser, Anna A.'
'Dobrzycki, Łukasz'
'Gutmann, Matthias J.'
'Woźniak, Krzysztof'
_publ_section_title
;
 Charge Densities of Two Polymorphs of Hydrated
 1,8-Bis(dimethylamino)naphthalene Hydrochloride---Similarities and
 Differences
;
_journal_issue                   12
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              5092
_journal_paper_doi               10.1021/cg1007445
_journal_volume                  10
_journal_year                    2010
_chemical_formula_sum            'C14 H24 Cl2 N2 O2'
_chemical_formula_weight         323.26
_chemical_name_systematic
; 
 ? 
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.583(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0638(3)
_cell_length_b                   9.7890(3)
_cell_length_c                   17.8746(6)
_cell_measurement_temperature    100(2)
_cell_volume                     1725.05(9)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.182
_diffrn_measured_fraction_theta_max 0.182
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0613
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3189
_diffrn_reflns_theta_full        49.31
_diffrn_reflns_theta_max         49.31
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  0.8253
_exptl_absorpt_correction_T_min  0.4350
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             211
_exptl_crystal_size_max          5.00
_exptl_crystal_size_mid          3.00
_exptl_crystal_size_min          1.00
_refine_diff_density_max         1.514
_refine_diff_density_min         -1.420
_refine_diff_density_rms         0.348
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.388
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         3189
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.388
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0735
_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)+(0.0001P)²+146.7493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2414
_refine_ls_wR_factor_ref         0.2417
_reflns_number_gt                3173
_reflns_number_total             3189
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg1007445_si_003.cif
_cod_data_source_block           dmcl100
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4501949
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
Cl1 Cl 0.0123(4) 0.9003(5) 0.6678(2) 0.0189(7) Uani 1 1 d
Cl2 Cl 0.4772(3) 0.9089(5) 0.8461(2) 0.0175(7) Uani 1 1 d
O1 O 0.1390(7) 0.6495(8) 0.7428(3) 0.0211(13) Uani 1 1 d
O2 O 0.3823(7) 0.6592(9) 0.7533(4) 0.0263(15) Uani 1 1 d
H1 H 0.0998(13) 0.5679(14) 0.7119(7) 0.031(3) Uani 1 1 d
H2 H 0.0942(14) 0.7342(16) 0.7182(7) 0.034(3) Uani 1 1 d
H3 H 0.4194(14) 0.7400(16) 0.7834(8) 0.036(3) Uani 1 1 d
H4 H 0.4240(14) 0.5771(15) 0.7804(8) 0.033(3) Uani 1 1 d
H5 H 0.2588(16) 0.6545(16) 0.7485(7) 0.035(3) Uani 1 1 d
N1 N 0.8350(3) 0.8421(4) 0.88229(18) 0.0132(6) Uani 1 1 d
N2 N 0.7255(3) 0.7515(4) 0.99273(17) 0.0116(6) Uani 1 1 d
C1 C 0.9659(4) 0.7966(6) 0.9247(2) 0.0120(9) Uani 1 1 d
C2 C 1.0823(5) 0.8183(6) 0.8967(3) 0.0171(11) Uani 1 1 d
C3 C 1.2096(5) 0.7751(7) 0.9374(3) 0.0200(11) Uani 1 1 d
C4 C 1.2195(5) 0.7077(6) 1.0057(3) 0.0167(10) Uani 1 1 d
C5 C 1.1135(5) 0.6113(6) 1.1061(3) 0.0163(10) Uani 1 1 d
C6 C 1.0012(5) 0.5832(7) 1.1360(3) 0.0185(11) Uani 1 1 d
C7 C 0.8728(5) 0.6289(6) 1.0975(2) 0.0145(10) Uani 1 1 d
C8 C 0.8599(5) 0.6996(6) 1.0303(2) 0.0121(9) Uani 1 1 d
C9 C 0.9722(5) 0.7266(6) 0.9956(2) 0.0109(9) Uani 1 1 d
C10 C 1.1022(5) 0.6816(6) 1.0357(2) 0.0131(9) Uani 1 1 d
C11 C 0.7924(5) 0.7651(8) 0.8101(3) 0.0228(13) Uani 1 1 d
C12 C 0.8309(6) 0.9908(7) 0.8696(4) 0.0243(12) Uani 1 1 d
C13 C 0.6767(5) 0.8602(7) 1.0385(3) 0.0207(11) Uani 1 1 d
C14 C 0.6233(5) 0.6418(6) 0.9726(3) 0.0174(10) Uani 1 1 d
H6 H 0.7498(12) 0.8011(14) 0.9370(6) 0.027(2) Uani 1 1 d
H7 H 1.0745(13) 0.8695(16) 0.8425(7) 0.034(3) Uani 1 1 d
H8 H 1.2984(11) 0.7959(16) 0.9150(8) 0.035(3) Uani 1 1 d
H9 H 1.3182(11) 0.6763(16) 1.0390(7) 0.032(3) Uani 1 1 d
H10 H 1.2166(11) 0.5825(17) 1.1364(7) 0.035(3) Uani 1 1 d
H11 H 1.0104(13) 0.5287(18) 1.1894(6) 0.039(3) Uani 1 1 d
H12 H 0.7847(12) 0.6102(17) 1.1221(7) 0.035(3) Uani 1 1 d
H13 H 0.7938(19) 0.659(2) 0.8226(9) 0.051(4) Uani 1 1 d
H14 H 0.8585(15) 0.784(2) 0.7704(7) 0.052(5) Uani 1 1 d
H15 H 0.6903(13) 0.7957(19) 0.7849(7) 0.040(3) Uani 1 1 d
H16 H 0.862(2) 1.0453(19) 0.9237(12) 0.055(4) Uani 1 1 d
H17 H 0.8963(18) 1.019(2) 0.8306(14) 0.061(6) Uani 1 1 d
H18 H 0.7270(15) 1.0185(17) 0.8442(11) 0.047(4) Uani 1 1 d
H19 H 0.6512(17) 0.8150(18) 1.0890(7) 0.044(4) Uani 1 1 d
H20 H 0.7536(16) 0.9361(17) 1.0540(10) 0.044(4) Uani 1 1 d
H21 H 0.5860(15) 0.9033(18) 1.0033(8) 0.042(3) Uani 1 1 d
H22 H 0.6032(16) 0.5936(19) 1.0242(8) 0.043(3) Uani 1 1 d
H23 H 0.6591(16) 0.5641(19) 0.9368(9) 0.047(4) Uani 1 1 d
H24 H 0.5307(13) 0.6908(16) 0.9396(8) 0.038(3) 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 0.0000 0.0000 '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'
Cl Cl 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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
H1 O1 H2 109.0(12)
H1 O1 H5 111.0(12)
H2 O1 H5 111.2(13)
H3 O2 H4 107.9(13)
H3 O2 H5 109.5(13)
H4 O2 H5 109.2(13)
C1 N1 C12 112.2(4)
C1 N1 C11 111.8(4)
C12 N1 C11 112.0(5)
C1 N1 H6 99.1(5)
C12 N1 H6 111.6(6)
C11 N1 H6 109.5(6)
C8 N2 C14 112.9(4)
C8 N2 C13 111.7(3)
C14 N2 C13 111.3(4)
C8 N2 H6 101.5(6)
C14 N2 H6 110.2(7)
C13 N2 H6 108.6(8)
C2 C1 C9 120.3(4)
C2 C1 N1 120.7(4)
C9 C1 N1 118.9(4)
C1 C2 C3 121.2(5)
C1 C2 H7 118.9(8)
C3 C2 H7 119.9(8)
C4 C3 C2 120.0(5)
C4 C3 H8 120.4(9)
C2 C3 H8 119.5(9)
C3 C4 C10 120.4(5)
C3 C4 H9 120.9(8)
C10 C4 H9 118.7(8)
C6 C5 C10 121.2(5)
C6 C5 H10 121.5(8)
C10 C5 H10 117.3(8)
C5 C6 C7 119.5(5)
C5 C6 H11 120.8(8)
C7 C6 H11 119.7(8)
C8 C7 C6 120.3(4)
C8 C7 H12 120.1(8)
C6 C7 H12 119.6(8)
C7 C8 C9 122.3(4)
C7 C8 N2 119.4(4)
C9 C8 N2 118.3(4)
C8 C9 C10 116.9(4)
C8 C9 C1 125.4(4)
C10 C9 C1 117.7(4)
C4 C10 C5 119.9(4)
C4 C10 C9 120.3(4)
C5 C10 C9 119.8(4)
N1 C11 H13 109.0(9)
N1 C11 H14 112.0(11)
H13 C11 H14 108.9(16)
N1 C11 H15 107.8(9)
H13 C11 H15 109.3(15)
H14 C11 H15 109.8(12)
N1 C12 H16 110.6(12)
N1 C12 H17 110.6(12)
H16 C12 H17 109.8(18)
N1 C12 H18 107.8(11)
H16 C12 H18 109.2(15)
H17 C12 H18 108.9(16)
N2 C13 H19 109.1(10)
N2 C13 H20 109.8(9)
H19 C13 H20 110.5(15)
N2 C13 H21 106.9(9)
H19 C13 H21 109.3(13)
H20 C13 H21 111.2(15)
N2 C14 H22 110.2(9)
N2 C14 H23 110.5(9)
H22 C14 H23 109.3(15)
N2 C14 H24 106.5(9)
H22 C14 H24 111.0(13)
H23 C14 H24 109.2(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 H1 1.005(16)
O1 H2 1.002(18)
O1 H5 1.191(18)
O2 H3 0.987(17)
O2 H4 0.987(18)
O2 H5 1.229(18)
N1 C1 1.452(6)
N1 C12 1.473(8)
N1 C11 1.482(7)
N1 H6 1.479(13)
N2 C8 1.475(6)
N2 C14 1.481(7)
N2 C13 1.485(7)
N2 H6 1.177(13)
C1 C2 1.380(6)
C1 C9 1.430(6)
C2 C3 1.405(8)
C2 H7 1.079(13)
C3 C4 1.375(8)
C3 H8 1.070(11)
C4 C10 1.414(7)
C4 H9 1.094(12)
C5 C6 1.372(7)
C5 C10 1.419(7)
C5 H10 1.106(13)
C6 C7 1.409(7)
C6 H11 1.080(12)
C7 C8 1.370(6)
C7 H12 1.082(12)
C8 C9 1.419(6)
C9 C10 1.429(7)
C11 H13 1.06(3)
C11 H14 1.082(14)
C11 H15 1.078(14)
C12 H16 1.09(2)
C12 H17 1.087(18)
C12 H18 1.088(15)
C13 H19 1.081(14)
C13 H20 1.068(17)
C13 H21 1.084(14)
C14 H22 1.091(15)
C14 H23 1.100(17)
C14 H24 1.107(14)
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
O1 H1 Cl2 1.005(16) 1.943(14) 2.948(8) 178.9(12) 2_546
O1 H2 Cl1 1.002(18) 1.958(16) 2.959(9) 177.8(12) .
O2 H3 Cl2 0.987(17) 2.016(15) 3.000(9) 174.6(14) .
O2 H4 Cl1 0.987(18) 2.007(16) 2.989(10) 173.4(13) 2_546
O1 H5 O2 1.191(18) 1.229(18) 2.420(11) 179.1(13) .
N2 H6 N1 1.177(13) 1.479(13) 2.602(5) 156.6(10) .
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
C12 N1 C1 C2 -59.6(6)
C11 N1 C1 C2 67.2(7)
C12 N1 C1 C9 121.4(5)
C11 N1 C1 C9 -111.8(5)
C9 C1 C2 C3 -1.2(9)
N1 C1 C2 C3 179.8(6)
C1 C2 C3 C4 1.2(10)
C2 C3 C4 C10 -0.2(9)
C10 C5 C6 C7 -2.1(9)
C5 C6 C7 C8 0.6(9)
C6 C7 C8 C9 1.8(8)
C6 C7 C8 N2 -177.4(5)
C14 N2 C8 C7 -59.7(6)
C13 N2 C8 C7 66.8(6)
C14 N2 C8 C9 121.1(5)
C13 N2 C8 C9 -112.5(5)
C7 C8 C9 C10 -2.7(8)
N2 C8 C9 C10 176.5(5)
C7 C8 C9 C1 178.3(6)
N2 C8 C9 C1 -2.5(8)
C2 C1 C9 C8 179.3(5)
N1 C1 C9 C8 -1.7(8)
C2 C1 C9 C10 0.3(8)
N1 C1 C9 C10 179.3(5)
C3 C4 C10 C5 179.7(6)
C3 C4 C10 C9 -0.8(9)
C6 C5 C10 C4 -179.2(6)
C6 C5 C10 C9 1.2(9)
C8 C9 C10 C4 -178.4(5)
C1 C9 C10 C4 0.7(8)
C8 C9 C10 C5 1.1(8)
C1 C9 C10 C5 -179.8(5)
