#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/26/2202669.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2202669
loop_
_publ_author_name
'Bolte, Michael'
'Panisch, Robin'
'Müller, Thomas'
_publ_section_title
;
 A cocrystal of diethylammonium chloride and diphenylamine
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o929
_journal_page_last               o930
_journal_paper_doi               10.1107/S1600536803010778
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C4 H12 N 1+, Cl 1-, C12 H11 N'
_chemical_formula_moiety         'C4 H12 N 1+, Cl 1-, C12 H11 N'
_chemical_formula_sum            'C16 H23 Cl N2'
_chemical_formula_weight         278.81
_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                 94.726(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0679(6)
_cell_length_b                   10.0077(6)
_cell_length_c                   17.8386(13)
_cell_measurement_reflns_used    19430
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.4
_cell_volume                     1613.33(19)
_computing_cell_refinement       X-AREA
_computing_data_collection       'X-AREA (Stoe & Cie, 2001)'
_computing_data_reduction        X-AREA
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 1991)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       ω
_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  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            27910
_diffrn_reflns_theta_full        27.90
_diffrn_reflns_theta_max         27.90
_diffrn_reflns_theta_min         2.44
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.9682
_exptl_absorpt_correction_T_min  0.9551
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(MULABS; Spek, 1990; Blessing, 1995)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         3833
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.965
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0270
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0466P)²] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0703
_reflns_number_gt                3087
_reflns_number_total             3833
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh6062.cif
_cod_data_source_block           I
_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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

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 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2202669
_cod_database_fobs_code          2202669
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 0.40033(12) 0.48481(12) 0.63545(6) 0.0338(2) Uani d . 1 . . C
H1A 0.4634 0.4436 0.5999 0.051 Uiso calc R 1 . . H
H1B 0.3841 0.5790 0.6223 0.051 Uiso calc R 1 . . H
H1C 0.3050 0.4382 0.6332 0.051 Uiso calc R 1 . . H
C2 0.47500(11) 0.47493(11) 0.71409(6) 0.0269(2) Uani d . 1 . . C
H2A 0.4922 0.3798 0.7272 0.032 Uiso calc R 1 . . H
H2B 0.5723 0.5202 0.7160 0.032 Uiso calc R 1 . . H
N3 0.38264(9) 0.53766(9) 0.76999(5) 0.02447(18) Uani d . 1 . . N
H3A 0.3703(14) 0.6254(15) 0.7583(7) 0.034(3) Uiso d . 1 . . H
H3B 0.2926(16) 0.4963(15) 0.7659(7) 0.037(3) Uiso d . 1 . . H
C4 0.44610(12) 0.52422(12) 0.84949(6) 0.0307(2) Uani d . 1 . . C
H4A 0.5479 0.5607 0.8545 0.037 Uiso calc R 1 . . H
H4B 0.4511 0.4286 0.8637 0.037 Uiso calc R 1 . . H
C5 0.35150(16) 0.59856(14) 0.90146(7) 0.0442(3) Uani d . 1 . . C
H5A 0.3949 0.5900 0.9534 0.066 Uiso calc R 1 . . H
H5B 0.2515 0.5607 0.8974 0.066 Uiso calc R 1 . . H
H5C 0.3467 0.6932 0.8873 0.066 Uiso calc R 1 . . H
Cl1 0.38089(2) 0.84251(2) 0.724177(15) 0.02832(8) Uani d . 1 . . Cl
N1 0.73130(9) 0.75457(9) 0.74821(5) 0.02451(18) Uani d . 1 . . N
H1 0.6484(15) 0.7948(14) 0.7426(7) 0.032(3) Uiso d . 1 . . H
C11 0.77637(10) 0.72692(10) 0.82350(5) 0.02177(19) Uani d . 1 . . C
C12 0.72848(11) 0.81509(10) 0.87765(6) 0.0250(2) Uani d . 1 . . C
H12 0.6731 0.8922 0.8621 0.030 Uiso calc R 1 . . H
C13 0.76118(11) 0.79075(11) 0.95344(6) 0.0291(2) Uani d . 1 . . C
H13 0.7273 0.8509 0.9895 0.035 Uiso calc R 1 . . H
C14 0.84321(12) 0.67899(12) 0.97758(6) 0.0328(2) Uani d . 1 . . C
H14 0.8660 0.6624 1.0297 0.039 Uiso calc R 1 . . H
C15 0.89117(13) 0.59205(12) 0.92385(6) 0.0344(2) Uani d . 1 . . C
H15 0.9474 0.5155 0.9397 0.041 Uiso calc R 1 . . H
C16 0.85866(11) 0.61467(10) 0.84744(6) 0.0274(2) Uani d . 1 . . C
H16 0.8923 0.5540 0.8116 0.033 Uiso calc R 1 . . H
C21 0.79040(10) 0.71156(9) 0.68263(5) 0.02151(18) Uani d . 1 . . C
C22 0.93418(10) 0.66203(10) 0.67961(6) 0.02491(19) Uani d . 1 . . C
H22 0.9968 0.6510 0.7246 0.030 Uiso calc R 1 . . H
C23 0.98511(11) 0.62898(10) 0.61048(6) 0.0285(2) Uani d . 1 . . C
H23 1.0830 0.5958 0.6089 0.034 Uiso calc R 1 . . H
C24 0.89636(12) 0.64337(11) 0.54398(6) 0.0303(2) Uani d . 1 . . C
H24 0.9325 0.6203 0.4972 0.036 Uiso calc R 1 . . H
C25 0.75338(12) 0.69221(11) 0.54701(6) 0.0295(2) Uani d . 1 . . C
H25 0.6913 0.7026 0.5018 0.035 Uiso calc R 1 . . H
C26 0.70081(10) 0.72573(10) 0.61511(6) 0.0252(2) Uani d . 1 . . C
H26 0.6028 0.7588 0.6162 0.030 Uiso calc R 1 . . H
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'
Cl Cl 0.1484 0.1585 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 C1 H1A 109.5 ?
C2 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C2 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
N3 C2 C1 111.09(8) ?
N3 C2 H2A 109.4 ?
C1 C2 H2A 109.4 ?
N3 C2 H2B 109.4 ?
C1 C2 H2B 109.4 ?
H2A C2 H2B 108.0 ?
C4 N3 C2 113.79(8) y
C4 N3 H3A 109.7(8) ?
C2 N3 H3A 108.6(8) ?
C4 N3 H3B 107.9(8) ?
C2 N3 H3B 107.7(9) ?
H3A N3 H3B 109.1(12) ?
N3 C4 C5 110.19(10) ?
N3 C4 H4A 109.6 ?
C5 C4 H4A 109.6 ?
N3 C4 H4B 109.6 ?
C5 C4 H4B 109.6 ?
H4A C4 H4B 108.1 ?
C4 C5 H5A 109.5 ?
C4 C5 H5B 109.5 ?
H5A C5 H5B 109.5 ?
C4 C5 H5C 109.5 ?
H5A C5 H5C 109.5 ?
H5B C5 H5C 109.5 ?
C21 N1 C11 129.96(8) y
C21 N1 H1 116.4(9) ?
C11 N1 H1 113.1(9) ?
C16 C11 N1 124.02(9) ?
C16 C11 C12 118.90(9) ?
N1 C11 C12 117.00(9) ?
C13 C12 C11 120.60(9) ?
C13 C12 H12 119.7 ?
C11 C12 H12 119.7 ?
C12 C13 C14 120.70(10) ?
C12 C13 H13 119.6 ?
C14 C13 H13 119.6 ?
C15 C14 C13 118.63(10) ?
C15 C14 H14 120.7 ?
C13 C14 H14 120.7 ?
C16 C15 C14 121.42(10) ?
C16 C15 H15 119.3 ?
C14 C15 H15 119.3 ?
C15 C16 C11 119.75(10) ?
C15 C16 H16 120.1 ?
C11 C16 H16 120.1 ?
N1 C21 C22 124.42(9) ?
N1 C21 C26 116.97(8) ?
C22 C21 C26 118.54(9) ?
C23 C22 C21 119.76(9) ?
C23 C22 H22 120.1 ?
C21 C22 H22 120.1 ?
C24 C23 C22 121.49(9) ?
C24 C23 H23 119.3 ?
C22 C23 H23 119.3 ?
C23 C24 C25 118.75(9) ?
C23 C24 H24 120.6 ?
C25 C24 H24 120.6 ?
C26 C25 C24 120.63(10) ?
C26 C25 H25 119.7 ?
C24 C25 H25 119.7 ?
C25 C26 C21 120.83(9) ?
C25 C26 H26 119.6 ?
C21 C26 H26 119.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.5098(15) ?
C1 H1A . 0.9800 ?
C1 H1B . 0.9800 ?
C1 H1C . 0.9800 ?
C2 N3 . 1.4924(13) y
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
N3 C4 . 1.4919(14) y
N3 H3A . 0.908(15) ?
N3 H3B . 0.913(15) ?
C4 C5 . 1.5100(16) ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
N1 C21 . 1.3944(12) y
N1 C11 . 1.3989(13) y
N1 H1 . 0.851(14) ?
C11 C16 . 1.3960(14) ?
C11 C12 . 1.4033(13) ?
C12 C13 . 1.3818(14) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.3917(16) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.3904(16) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.3892(15) ?
C15 H15 . 0.9500 ?
C16 H16 . 0.9500 ?
C21 C22 . 1.4000(13) ?
C21 C26 . 1.4035(13) ?
C22 C23 . 1.3917(14) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.3850(15) ?
C23 H23 . 0.9500 ?
C24 C25 . 1.3908(15) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.3824(14) ?
C25 H25 . 0.9500 ?
C26 H26 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N3 H3A Cl1 . 0.908(15) 2.260(15) 3.1581(9) 170.0(12)
N3 H3B Cl1 2_546 0.913(15) 2.218(15) 3.0946(9) 160.7(12)
N1 H1 Cl1 . 0.851(14) 2.467(14) 3.2909(9) 162.9(12)
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 C2 N3 C4 176.60(9)
C2 N3 C4 C5 176.01(9)
C21 N1 C11 C16 -23.23(16)
C21 N1 C11 C12 160.09(10)
C16 C11 C12 C13 -0.50(15)
N1 C11 C12 C13 176.35(9)
C11 C12 C13 C14 0.52(16)
C12 C13 C14 C15 -0.22(17)
C13 C14 C15 C16 -0.10(18)
C14 C15 C16 C11 0.11(17)
N1 C11 C16 C15 -176.43(10)
C12 C11 C16 C15 0.19(15)
C11 N1 C21 C22 -19.68(17)
C11 N1 C21 C26 163.61(10)
N1 C21 C22 C23 -176.28(10)
C26 C21 C22 C23 0.39(15)
C21 C22 C23 C24 -0.28(16)
C22 C23 C24 C25 0.10(16)
C23 C24 C25 C26 -0.02(16)
C24 C25 C26 C21 0.14(16)
N1 C21 C26 C25 176.59(10)
C22 C21 C26 C25 -0.32(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21131651
2 PubChem 139066156
