#------------------------------------------------------------------------------
#$Date: 2019-11-14 14:42:34 +0200 (Thu, 14 Nov 2019) $
#$Revision: 227796 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/51/7235105.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_7235105
loop_
_publ_author_name
'Ayoub, Ghada'
'Štrukil, Vjekoslav'
'Fábián, László'
'Mottillo, Cristina'
'Bao, Huizhi'
'Murata, Yasujiro'
'Moores, Audrey'
'Margetić, Davor'
'Eckert-Maksić, Mirjana'
'Friščić, Tomislav'
_publ_section_title
;
 Mechanochemistryvs.solution growth: striking differences in bench
 stability of a cimetidine salt based on a synthetic method
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              7242
_journal_paper_doi               10.1039/C8CE01727A
_journal_volume                  20
_journal_year                    2018
_chemical_formula_sum            'C15 H21.5 N6.5 O4 S'
_chemical_formula_weight         388.95
_chemical_name_systematic
; 
 cimetidinium fumarate acetonitrile solvate
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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
_audit_update_record
;
2018-08-19 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 107.4620(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.7835(12)
_cell_length_b                   8.0156(7)
_cell_length_c                   18.7113(16)
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      1.62
_cell_volume                     1972.0(3)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_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  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0286
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9856
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_correction_T_min  0.9467
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0463P)²+0.8359P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0942
_reflns_number_gt                2972
_reflns_number_total             3476
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8ce01727a2.cif
_cod_data_source_block           compound-1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/current/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 5376 2017-05-30 11:51:03Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_original_formula_sum        'C15 H21.50 N6.50 O4 S'
_cod_database_code               7235105
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.36550(12) 0.8391(2) 1.09869(9) 0.0212(4) Uani 1 1 d . A 1
C2 C 0.29590(12) 0.7462(2) 1.11931(9) 0.0203(4) Uani 1 1 d . A 1
C3 C 0.26209(13) 1.0122(2) 1.13139(9) 0.0220(4) Uani 1 1 d . A 1
H3 H 0.2314 1.1116 1.1420 0.026 Uiso 1 1 calc R A 1
C4 C 0.45597(14) 0.7906(3) 1.07534(11) 0.0308(4) Uani 1 1 d . A 1
H4A H 0.5179 0.8067 1.1174 0.046 Uiso 1 1 calc R A 1
H4B H 0.4592 0.8601 1.0330 0.046 Uiso 1 1 calc R A 1
H4C H 0.4503 0.6730 1.0603 0.046 Uiso 1 1 calc R A 1
C5 C 0.28291(13) 0.5620(2) 1.12093(10) 0.0238(4) Uani 1 1 d . A 1
H5A H 0.2862 0.5278 1.1725 0.029 Uiso 1 1 calc R A 1
H5B H 0.3401 0.5075 1.1082 0.029 Uiso 1 1 calc R A 1
C6 C 0.18335(14) 0.5264(2) 0.96636(10) 0.0267(4) Uani 1 1 d . A 1
H6A H 0.1168 0.5445 0.9282 0.032 Uiso 1 1 calc R A 1
H6B H 0.2240 0.6295 0.9696 0.032 Uiso 1 1 calc R A 1
C7 C 0.23801(13) 0.3828(2) 0.94171(9) 0.0239(4) Uani 1 1 d . A 1
H7A H 0.3065 0.3698 0.9781 0.029 Uiso 1 1 calc R A 1
H7B H 0.1998 0.2783 0.9419 0.029 Uiso 1 1 calc R A 1
C8 C 0.32209(12) 0.5021(2) 0.85519(9) 0.0191(4) Uani 1 1 d . A 1
C9 C 0.26122(14) 0.4382(3) 0.72025(10) 0.0291(4) Uani 1 1 d . A 1
H9A H 0.2671 0.3171 0.7273 0.044 Uiso 1 1 calc R A 1
H9B H 0.2812 0.4694 0.6760 0.044 Uiso 1 1 calc R A 1
H9C H 0.1907 0.4723 0.7132 0.044 Uiso 1 1 calc R A 1
C10 C 0.46584(13) 0.6551(2) 0.90803(9) 0.0227(4) Uani 1 1 d . A 1
C11 C 0.94528(13) 0.7568(2) 0.78813(9) 0.0195(4) Uani 1 1 d . B 1
C12 C 0.98910(12) 0.5907(2) 0.78140(9) 0.0194(4) Uani 1 1 d . B 1
H12 H 1.0512 0.5838 0.7693 0.023 Uiso 1 1 calc R B 1
C13 C 0.94348(12) 0.4525(2) 0.79193(9) 0.0187(4) Uani 1 1 d . B 1
H13 H 0.8808 0.4630 0.8029 0.022 Uiso 1 1 calc R B 1
C14 C 0.98310(12) 0.2803(2) 0.78789(9) 0.0175(4) Uani 1 1 d . B 1
N1 N 0.34172(11) 1.00386(19) 1.10612(8) 0.0211(3) Uani 1 1 d . A 1
N2 N 0.23248(11) 0.85828(19) 1.13944(8) 0.0216(3) Uani 1 1 d . A 1
N3 N 0.24833(11) 0.40843(19) 0.86715(9) 0.0225(3) Uani 1 1 d . A 1
N4 N 0.32733(11) 0.52084(18) 0.78573(8) 0.0203(3) Uani 1 1 d . A 1
N5 N 0.38759(10) 0.57228(19) 0.91549(8) 0.0243(3) Uani 1 1 d . A 1
N6 N 0.53833(11) 0.7296(2) 0.90923(9) 0.0287(4) Uani 1 1 d . A 1
O1 O 0.86480(9) 0.77470(15) 0.80058(7) 0.0277(3) Uani 1 1 d . B 1
O2 O 1.00239(10) 0.87993(16) 0.77824(9) 0.0365(4) Uani 1 1 d . B 1
H6 H 0.9765 0.9711 0.7851 0.055 Uiso 1 1 calc R B 1
O3 O 1.06658(8) 0.26137(14) 0.77619(7) 0.0208(3) Uani 1 1 d . B 1
O4 O 0.92631(9) 0.16245(14) 0.79692(7) 0.0268(3) Uani 1 1 d . B 1
S1 S 0.16312(3) 0.48772(6) 1.05624(3) 0.02904(15) Uani 1 1 d . A 1
C15 C 0.0071(8) 0.0482(13) 1.0061(6) 0.082(3) Uani 0.50 1 d P C -1
H15A H 0.0471 0.1159 1.0483 0.123 Uiso 0.50 1 calc PR C -1
H15B H -0.0308 -0.0368 1.0244 0.123 Uiso 0.50 1 calc PR C -1
H15C H -0.0407 0.1200 0.9697 0.123 Uiso 0.50 1 calc PR C -1
C16 C 0.0767(5) -0.0348(8) 0.9695(3) 0.0653(16) Uani 0.50 1 d P C -1
N7 N 0.1430(5) -0.0422(6) 0.9457(3) 0.0676(13) Uani 0.50 1 d P C -1
H1 H 0.3761(17) 1.086(3) 1.0996(12) 0.042(7) Uiso 1 1 d . . .
H2 H 0.1871(16) 0.838(3) 1.1581(12) 0.035(6) Uiso 1 1 d . . .
H5 H 0.3731(14) 0.580(2) 0.7789(10) 0.020(5) Uiso 1 1 d . . .
H4 H 0.2012(15) 0.372(2) 0.8301(12) 0.025(5) Uiso 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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 C1 N1 106.69(15)
C2 C1 C4 131.60(17)
N1 C1 C4 121.64(16)
C1 C2 N2 106.21(16)
C1 C2 C5 130.46(16)
N2 C2 C5 123.32(15)
N1 C3 N2 108.15(16)
C2 C5 S1 113.54(12)
C7 C6 S1 112.34(13)
N3 C7 C6 112.51(15)
N4 C8 N3 119.61(16)
N4 C8 N5 123.67(15)
N3 C8 N5 116.72(15)
N6 C10 N5 173.09(19)
O1 C11 O2 124.28(16)
O1 C11 C12 122.93(15)
O2 C11 C12 112.78(14)
C13 C12 C11 121.17(15)
C12 C13 C14 124.81(15)
O3 C14 O4 124.93(15)
O3 C14 C13 119.54(15)
O4 C14 C13 115.52(14)
C3 N1 C1 109.46(15)
C3 N2 C2 109.47(15)
C8 N3 C7 122.49(15)
C8 N4 C9 124.68(15)
C10 N5 C8 119.47(15)
C6 S1 C5 101.46(8)
N7 C16 C15 155.5(7)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.359(2)
C1 N1 1.378(2)
C1 C4 1.491(2)
C2 N2 1.382(2)
C2 C5 1.489(3)
C3 N1 1.321(2)
C3 N2 1.322(2)
C5 S1 1.8292(18)
C6 C7 1.521(3)
C6 S1 1.8122(18)
C7 N3 1.459(2)
C8 N4 1.332(2)
C8 N3 1.335(2)
C8 N5 1.339(2)
C9 N4 1.449(2)
C10 N6 1.158(2)
C10 N5 1.309(2)
C11 O1 1.208(2)
C11 O2 1.310(2)
C11 C12 1.483(2)
C12 C13 1.317(2)
C13 C14 1.495(2)
C14 O3 1.2433(19)
C14 O4 1.270(2)
C15 C16 1.491(15)
C16 N7 1.132(8)
