#------------------------------------------------------------------------------
#$Date: 2025-08-19 11:35:14 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301801 $
#$URL: svn://www.crystallography.net/cod/cif/2/02/14/2021435.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_2021435
loop_
_publ_author_name
'Borodi, Gheorghe'
'Turza, Alexandru'
'Onija, Oana'
'Bende, Attila'
_publ_section_title
;
 Succinic, fumaric, adipic and oxalic acid cocrystals of promethazine
 hydrochloride
;
_journal_coeditor_code           QP3016
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              107
_journal_page_last               119
_journal_paper_doi               10.1107/S2053229618017904
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          '2C17 H21 N2 S +, 2Cl -, C4 H6 O4'
_chemical_formula_moiety         '2(C17 H21 N2 S +), 2(Cl -), C4 H6 O4'
_chemical_formula_sum            'C38 H48 Cl2 N4 O4 S2'
_chemical_formula_weight         759.82
_chemical_name_common
;
Promethazine hydrochloride succinic acid
;
_chemical_name_systematic
;
N,N-Dimethyl-1-(10H-phenothiazin-10-yl)propan-2-aminium
chloride succinic acid monosolvate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 103.070(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8247(3)
_cell_length_b                   26.4201(7)
_cell_length_c                   8.7393(4)
_cell_measurement_reflns_used    8891
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.057
_cell_measurement_theta_min      5.460
_cell_volume                     1984.78(13)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2012)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2012)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2016 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293.15
_diffrn_measured_fraction_theta_full 0.922
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type
'Agilent SuperNova Dual Source diffractometer with an Eos detector'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1226
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11754
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.057
_diffrn_reflns_theta_min         5.460
_exptl_absorpt_coefficient_mu    2.799
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2012)
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_description       needle
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.628
_refine_diff_density_min         -0.371
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3503
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0721
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1170P)²+0.9442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2084
_refine_ls_wR_factor_ref         0.2140
_reflns_number_gt                3008
_reflns_number_total             3503
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            qp3016sup1.cif
_cod_data_source_block           Promethazine_Hydrochloride_succinic_acid
_cod_depositor_comments
;
Adding full bibliography for 2021435--2021439.cif.

2019-10-23
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        1984.78(12)
_cod_original_formula_moiety     'C17 H21 N2 S +, Cl -, 0.5(C4 H6 O4)'
_cod_original_formula_iupac      'C17 H21 N2 S +, Cl -, 0.5C4 H6 O4'
_cod_original_formula_sum        'C19 H24 Cl N2 O2 S'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     379.91
_cod_database_code               2021435
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.541
_shelx_estimated_absorpt_t_max   0.787
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_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_occupancy
Cl Cl1 0.60991(10) 0.28893(3) 0.57926(9) 0.0550(3) Uani d 1
S S1 1.11147(12) 0.06827(3) 0.75956(12) 0.0641(3) Uani d 1
N N2 0.4877(3) 0.18028(8) 0.5415(2) 0.0343(5) Uani d 1
H H2 0.527041 0.215010 0.543037 0.041 Uiso calc 1
O O1 0.6141(4) 0.39576(9) 0.4668(3) 0.0748(8) Uani d 1
H H1 0.614312 0.368266 0.510377 0.112 Uiso calc 1
N N1 0.8953(3) 0.13927(10) 0.5586(3) 0.0454(6) Uani d 1
C C14 0.6285(3) 0.14657(10) 0.5855(3) 0.0354(6) Uani d 1
H H14 0.679744 0.154072 0.694728 0.042 Uiso calc 1
O O2 0.5101(5) 0.42148(10) 0.6600(3) 0.0834(10) Uani d 1
C C11 0.9526(4) 0.21099(12) 0.7423(3) 0.0459(7) Uani d 1
H H11 0.879999 0.231054 0.675289 0.055 Uiso calc 1
C C13 0.7426(3) 0.15987(12) 0.4836(3) 0.0414(6) Uani d 1
H H13A 0.707373 0.145505 0.379481 0.050 Uiso calc 1
H H13B 0.749195 0.196317 0.473412 0.050 Uiso calc 1
C C10 1.0351(4) 0.23054(14) 0.8834(4) 0.0530(8) Uani d 1
H H10 1.015404 0.263376 0.911985 0.064 Uiso calc 1
C C7 1.0893(3) 0.13247(12) 0.8040(3) 0.0434(6) Uani d 1
C C12 0.9778(3) 0.16124(11) 0.6999(3) 0.0392(6) Uani d 1
C C1 0.9752(4) 0.10842(12) 0.4720(4) 0.0463(7) Uani d 1
C C6 1.0838(4) 0.07314(12) 0.5538(4) 0.0528(8) Uani d 1
C C16 0.3900(4) 0.17199(15) 0.3818(4) 0.0545(8) Uani d 1
H H16A 0.345098 0.138745 0.375584 0.082 Uiso calc 1
H H16B 0.453034 0.175009 0.305956 0.082 Uiso calc 1
H H16C 0.308560 0.196833 0.360319 0.082 Uiso calc 1
C C17 0.3905(4) 0.17832(13) 0.6605(4) 0.0523(8) Uani d 1
H H17A 0.452784 0.187510 0.761596 0.078 Uiso calc 1
H H17B 0.351030 0.144629 0.665180 0.078 Uiso calc 1
H H17C 0.305188 0.201542 0.631448 0.078 Uiso calc 1
C C9 1.1459(5) 0.20193(15) 0.9816(4) 0.0602(9) Uani d 1
H H9 1.202038 0.215610 1.075506 0.072 Uiso calc 1
C C18 0.5536(5) 0.43033(12) 0.5443(4) 0.0522(8) Uani d 1
C C8 1.1740(4) 0.15321(14) 0.9416(4) 0.0543(8) Uani d 1
H H8 1.250391 0.134115 1.007428 0.065 Uiso calc 1
C C2 0.9512(5) 0.11077(15) 0.3100(4) 0.0584(9) Uani d 1
H H2A 0.882785 0.134550 0.254015 0.070 Uiso calc 1
C C5 1.1637(5) 0.04138(15) 0.4738(6) 0.0706(11) Uani d 1
H H5 1.237117 0.018917 0.529143 0.085 Uiso calc 1
C C19 0.5459(5) 0.48106(12) 0.4662(4) 0.0613(10) Uani d 1
H H19A 0.650780 0.493779 0.476113 0.074 Uiso calc 1
H H19B 0.499512 0.477101 0.355119 0.074 Uiso calc 1
C C3 1.0292(6) 0.07763(18) 0.2310(5) 0.0768(13) Uani d 1
H H3 1.010454 0.078724 0.122003 0.092 Uiso calc 1
C C4 1.1348(6) 0.04294(17) 0.3135(7) 0.0853(15) Uani d 1
H H4 1.186024 0.020747 0.259685 0.102 Uiso calc 1
C C15 0.5874(5) 0.09086(13) 0.5761(4) 0.0544(8) Uani d 1
H H15A 0.543413 0.081833 0.468821 0.082 Uiso calc 1
H H15B 0.513102 0.084207 0.638641 0.082 Uiso calc 1
H H15C 0.679569 0.071200 0.614840 0.082 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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_site_symmetry_1
_geom_angle
C7 S1 C6 . 99.07(14)
C16 N2 C14 . 115.1(2)
C16 N2 C17 . 110.4(3)
C17 N2 C14 . 111.9(2)
C12 N1 C13 . 118.7(2)
C1 N1 C13 . 119.8(2)
C1 N1 C12 . 119.2(2)
N2 C14 C13 . 109.3(2)
N2 C14 C15 . 112.8(2)
C15 C14 C13 . 111.9(2)
C10 C11 C12 . 120.3(3)
N1 C13 C14 . 108.3(2)
C9 C10 C11 . 120.6(3)
C12 C7 S1 . 118.4(2)
C8 C7 S1 . 120.7(2)
C8 C7 C12 . 120.9(3)
C11 C12 N1 . 122.6(3)
C11 C12 C7 . 117.9(3)
C7 C12 N1 . 119.5(3)
N1 C1 C6 . 118.5(3)
C2 C1 N1 . 123.0(3)
C2 C1 C6 . 118.5(3)
C1 C6 S1 . 119.1(2)
C5 C6 S1 . 120.2(3)
C5 C6 C1 . 120.7(4)
C8 C9 C10 . 120.1(3)
O1 C18 C19 . 111.6(3)
O2 C18 O1 . 123.3(3)
O2 C18 C19 . 125.1(3)
C9 C8 C7 . 120.2(3)
C1 C2 C3 . 120.1(4)
C4 C5 C6 . 120.1(4)
C19 C19 C18 3_666 113.1(3)
C4 C3 C2 . 120.6(4)
C5 C4 C3 . 120.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
S1 C7 . 1.761(3)
S1 C6 . 1.764(4)
N2 C14 . 1.506(3)
N2 C16 . 1.481(4)
N2 C17 . 1.491(3)
O1 C18 . 1.320(4)
N1 C13 . 1.463(4)
N1 C12 . 1.409(4)
N1 C1 . 1.406(4)
C14 C13 . 1.528(4)
C14 C15 . 1.514(4)
O2 C18 . 1.183(4)
C11 C10 . 1.382(5)
C11 C12 . 1.397(4)
C10 C9 . 1.373(5)
C7 C12 . 1.403(4)
C7 C8 . 1.378(5)
C1 C6 . 1.410(5)
C1 C2 . 1.384(5)
C6 C5 . 1.383(5)
C9 C8 . 1.371(5)
C18 C19 . 1.499(4)
C2 C3 . 1.390(5)
C5 C4 . 1.366(7)
C19 C19 3_666 1.491(7)
C3 C4 . 1.387(8)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139062864
