#------------------------------------------------------------------------------
#$Date: 2016-08-07 11:20:07 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185217 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/50/7225043.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_7225043
loop_
_publ_author_name
'Skořepová, Eliška'
'Hušák, Michal'
'Ridvan, Luděk'
'Tkadlecová, Marcela'
'Havlíček, Jaroslav'
'Dušek, Michal'
_publ_section_title
;
 Iodine salts of the pharmaceutical compound agomelatine: the effect of
 the symmetric H-bond on amide protonation
;
_journal_issue                   24
_journal_name_full               CrystEngComm
_journal_page_first              4518
_journal_paper_doi               10.1039/C6CE00304D
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C15 H17.50 I1.50 N1 O2'
_chemical_formula_sum            'C15 H17.5 I1.5 N O2'
_chemical_formula_weight         434.17
_chemical_name_systematic        'agomelatine hemitriiodide '
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_update_record
;
2016-02-04 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.551(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4953(4)
_cell_length_b                   7.4545(4)
_cell_length_c                   23.2683(10)
_cell_measurement_reflns_used    5535
_cell_measurement_temperature    190
_cell_measurement_theta_max      77
_cell_measurement_theta_min      5
_cell_volume                     1645.36(13)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_pressure         100
_diffrn_ambient_temperature      190
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.041
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7712
_diffrn_reflns_theta_full        67.669
_diffrn_reflns_theta_max         76.896
_diffrn_reflns_theta_min         4.661
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    22.655
_exptl_absorpt_correction_T_max  0.02
_exptl_absorpt_correction_T_min  0.00
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_crystal_colour            red-brown
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.785
_exptl_crystal_size_mid          0.185
_exptl_crystal_size_min          0.168
_refine_diff_density_max         1.41
_refine_diff_density_min         -1.37
_refine_ls_extinction_coef       12(2)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   0.9861
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         3355
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0450
_refine_ls_shift/su_max          0.0013640
_refine_ls_shift/su_mean         0.0000213
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.08P)² + 5.09P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1345
_refine_ls_wR_factor_gt          0.1296
_refine_ls_wR_factor_ref         0.1345
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              29
_reflns_limit_l_min              0
_reflns_number_gt                3076
_reflns_number_total             3358
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   4.04
_oxford_diffrn_Wilson_scale      0.06
_oxford_refine_ls_r_factor_ref   0.0480
_oxford_refine_ls_scale          4.31(12)
_oxford_reflns_number_all        3355
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            c6ce00304d2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 7225043--7225045.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_original_formula_sum        'C15 H17.50 I1.50 N1 O2'
_cod_database_code               7225043
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT EXTPARAM 
RIDE C   (   4,X'S) H   (  41,X'S) H   (  43,X'S) H   (  42,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE N   (  17,X'S) H   ( 171,X'S) 
RIDE O   (  19,X'S) H   ( 192,X'S) 
RIDE C   (  20,X'S) H   ( 203,X'S) H   ( 202,X'S) H   ( 201,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
I1 I 0.5000 0.5000 0.5000 0.0482 1.0000 Uani S
I2 I 0.55858(4) 0.31881(7) 0.392277(18) 0.0613 1.0000 Uani .
O3 O 0.3754(4) 0.8647(6) 0.2627(2) 0.0562 1.0000 Uani .
C4 C 0.4686(7) 0.7280(12) 0.2820(4) 0.0706 1.0000 Uani .
C5 C 0.2456(5) 0.8724(7) 0.2851(2) 0.0387 1.0000 Uani .
C6 C 0.1549(6) 1.0043(7) 0.2598(2) 0.0436 1.0000 Uani .
C7 C 0.0230(6) 1.0218(7) 0.2781(2) 0.0412 1.0000 Uani .
C8 C -0.0291(5) 0.9127(7) 0.3224(2) 0.0351 1.0000 Uani .
C9 C -0.1674(6) 0.9310(8) 0.3407(2) 0.0462 1.0000 Uani .
C10 C -0.2160(6) 0.8209(9) 0.3824(3) 0.0492 1.0000 Uani .
C11 C -0.1286(6) 0.6882(8) 0.4068(2) 0.0446 1.0000 Uani .
C12 C 0.0083(5) 0.6653(7) 0.3912(2) 0.0356 1.0000 Uani .
C13 C 0.0615(5) 0.7793(6) 0.34745(19) 0.0321 1.0000 Uani .
C14 C 0.2010(5) 0.7628(6) 0.32803(19) 0.0328 1.0000 Uani .
C15 C 0.0971(6) 0.5176(7) 0.4180(2) 0.0386 1.0000 Uani .
C16 C 0.0954(6) 0.3500(7) 0.3803(2) 0.0391 1.0000 Uani .
N17 N 0.1880(5) 0.2111(6) 0.40524(19) 0.0417 1.0000 Uani .
C18 C 0.1528(6) 0.1024(7) 0.4461(2) 0.0391 1.0000 Uani .
O19 O 0.028033(10) 0.108279(10) 0.463417(10) 0.0483 1.0000 Uani .
C20 C 0.2601(7) -0.0260(8) 0.4711(3) 0.0519 1.0000 Uani .
H41 H 0.5541 0.7373 0.2614 0.1050 1.0000 Uiso R
H43 H 0.4889 0.7417 0.3227 0.1048 1.0000 Uiso R
H42 H 0.4242 0.6134 0.2745 0.1050 1.0000 Uiso R
H61 H 0.1856 1.0782 0.2312 0.0519 1.0000 Uiso R
H71 H -0.0352 1.1088 0.2612 0.0489 1.0000 Uiso R
H91 H -0.2256 1.0199 0.3246 0.0541 1.0000 Uiso R
H101 H -0.3076 0.8329 0.3949 0.0588 1.0000 Uiso R
H111 H -0.1634 0.6124 0.4346 0.0530 1.0000 Uiso R
H141 H 0.2617 0.6773 0.3446 0.0391 1.0000 Uiso R
H151 H 0.0600 0.4888 0.4548 0.0461 1.0000 Uiso R
H152 H 0.1936 0.5586 0.4232 0.0459 1.0000 Uiso R
H161 H 0.0003 0.3016 0.3760 0.0467 1.0000 Uiso R
H162 H 0.1304 0.3842 0.3430 0.0468 1.0000 Uiso R
H203 H 0.2360 -0.0600 0.5091 0.0774 1.0000 Uiso R
H202 H 0.3510 0.0302 0.4725 0.0774 1.0000 Uiso R
H201 H 0.2641 -0.1308 0.4477 0.0773 1.0000 Uiso R
H171 H 0.2755 0.2175 0.3986 0.0498 1.0000 Uiso R
H192 H 0.0000 0.0000 0.5000 0.0712 1.0000 Uiso RS
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
I -0.3257 6.8362 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776
4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
I2 2_666 I1 I2 179.996 yes
C4 . O3 C5 118.4(5) yes
O3 . C4 H41 108.7 no
O3 . C4 H43 109.3 no
H41 . C4 H43 110.2 no
O3 . C4 H42 108.7 no
H41 . C4 H42 110.2 no
H43 . C4 H42 109.7 no
O3 . C5 C6 114.5(5) yes
O3 . C5 C14 124.6(5) yes
C6 . C5 C14 120.9(5) yes
C5 . C6 C7 119.5(5) yes
C5 . C6 H61 120.6 no
C7 . C6 H61 119.9 no
C6 . C7 C8 122.2(5) yes
C6 . C7 H71 118.5 no
C8 . C7 H71 119.3 no
C7 . C8 C9 121.7(5) yes
C7 . C8 C13 118.3(4) yes
C9 . C8 C13 120.0(5) yes
C8 . C9 C10 120.5(5) yes
C8 . C9 H91 119.5 no
C10 . C9 H91 120.0 no
C9 . C10 C11 120.0(5) yes
C9 . C10 H101 120.9 no
C11 . C10 H101 119.1 no
C10 . C11 C12 122.1(5) yes
C10 . C11 H111 119.3 no
C12 . C11 H111 118.6 no
C11 . C12 C13 118.7(5) yes
C11 . C12 C15 120.0(5) yes
C13 . C12 C15 121.3(4) yes
C12 . C13 C8 118.7(4) yes
C12 . C13 C14 122.4(4) yes
C8 . C13 C14 119.0(4) yes
C13 . C14 C5 120.1(4) yes
C13 . C14 H141 119.7 no
C5 . C14 H141 120.3 no
C12 . C15 C16 111.7(4) yes
C12 . C15 H151 108.1 no
C16 . C15 H151 109.4 no
C12 . C15 H152 109.3 no
C16 . C15 H152 108.4 no
H151 . C15 H152 109.9 no
C15 . C16 N17 111.2(4) yes
C15 . C16 H161 110.5 no
N17 . C16 H161 108.5 no
C15 . C16 H162 107.5 no
N17 . C16 H162 108.3 no
H161 . C16 H162 110.8 no
C16 . N17 C18 124.0(5) yes
C16 . N17 H171 117.6 no
C18 . N17 H171 116.7 no
N17 . C18 O19 118.9(4) yes
N17 . C18 C20 119.3(5) yes
O19 . C18 C20 121.8(5) yes
C18 . O19 H192 116.0 no
C18 . C20 H203 110.0 no
C18 . C20 H202 109.2 no
H203 . C20 H202 109.6 no
C18 . C20 H201 110.2 no
H203 . C20 H201 109.2 no
H202 . C20 H201 108.6 no
O19 2_556 H192 O19 180.0 no
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
I1 I2 2_666 2.9224(4) yes
I1 I2 . 2.9224(4) yes
O3 C4 . 1.410(8) yes
O3 C5 . 1.360(7) yes
C4 H41 . 0.964 no
C4 H43 . 0.964 no
C4 H42 . 0.964 no
C5 C6 . 1.416(7) yes
C5 C14 . 1.373(7) yes
C6 C7 . 1.347(8) yes
C6 H61 . 0.922 no
C7 C8 . 1.419(7) yes
C7 H71 . 0.929 no
C8 C9 . 1.405(7) yes
C8 C13 . 1.422(6) yes
C9 C10 . 1.367(9) yes
C9 H91 . 0.931 no
C10 C11 . 1.396(9) yes
C10 H101 . 0.934 no
C11 C12 . 1.376(7) yes
C11 H111 . 0.930 no
C12 C13 . 1.435(7) yes
C12 C15 . 1.505(7) yes
C13 C14 . 1.425(7) yes
C14 H141 . 0.931 no
C15 C16 . 1.526(7) yes
C15 H151 . 0.965 no
C15 H152 . 0.968 no
C16 N17 . 1.461(6) yes
C16 H161 . 0.973 no
C16 H162 . 0.977 no
N17 C18 . 1.304(7) yes
N17 H171 . 0.853 no
C18 O19 . 1.270(6) yes
C18 C20 . 1.497(7) yes
O19 H192 . 1.211 no
C20 H203 . 0.957 no
C20 H202 . 0.959 no
C20 H201 . 0.954 no
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
0 1 7 x
-1 0 10 x
0 9 3 x
