#------------------------------------------------------------------------------
#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/63/7226342.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_7226342
loop_
_publ_author_name
'Hutchins, Kristin M.'
'Kummer, Katherine A.'
'Groeneman, Ryan H.'
'Reinheimer, Eric W.'
'Sinnwell, Michael A.'
'Swenson, Dale C.'
'MacGillivray, Leonard R.'
_publ_section_title
;
 Thermal expansion properties of three isostructural co-crystals composed
 of isosteric components: interplay between halogen and hydrogen bonds
;
_journal_issue                   43
_journal_name_full               CrystEngComm
_journal_page_first              8354
_journal_paper_doi               10.1039/C6CE01674J
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C10 H8 N4'
_chemical_formula_sum            'C10 H8 N4'
_chemical_formula_weight         184.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_date             2015-04-13
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-04-14 deposited with the CCDC.
2016-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                90.165(5)
_cell_angle_beta                 95.411(5)
_cell_angle_gamma                99.256(5)
_cell_formula_units_Z            1
_cell_length_a                   3.7762(4)
_cell_length_b                   5.8688(7)
_cell_length_c                   10.3157(12)
_cell_measurement_reflns_used    3245
_cell_measurement_temperature    190(2)
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      1.00
_cell_volume                     224.59(4)
_computing_cell_refinement       'HKL Scalepack (Otwinowski and Minor, 1997)'
_computing_data_collection       'Collect (Hooft, 1998)'
_computing_data_reduction        'Denzo (Otwinowski and Minor, 1997)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      190(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.933
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'CCD rotation images, phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.933
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3229
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.392
_diffrn_reflns_theta_min         1.983
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_correction_T_min  0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       plate-like
_exptl_crystal_F_000             96
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.030(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     81
_refine_ls_number_reflns         827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0366
_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)+(0.0517P)²+0.0345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.1012
_reflns_Friedel_coverage         0.000
_reflns_number_gt                668
_reflns_number_total             827
_reflns_threshold_expression     'I > 2σ(I)'
_iucr_refine_instructions_details
;
TITL mcg1522lt_a.res in P-1
REM Old TITL mcg1522lt in P-1 #2
REM SHELXT solution in P-1
REM R1 0.111, Rweak 0.005, Alpha 0.031, Orientation as input
REM Formula found by SHELXT: C5 N2
rem EXTI 0.029788
CELL 0.71073 3.7762 5.8688 10.3157 90.165 95.411 99.256
ZERR 1 0.0004 0.0007 0.0012 0.005 0.005 0.005
LATT 1
SFAC C H N
UNIT 10 8 4
 
L.S. 4 0 0
PLAN  -20
SIZE 0.04 0.1 0.28
TEMP -83
BOND $H
MORE -1
CONF
fmap 2 53
acta 52
REM <olex2.extras>
REM <HklSrc "%.\\mcg1522lt.hkl">
REM </olex2.extras>
 
WGHT    0.051700    0.034500
EXTI    0.029774
FVAR       1.80212
N2    3    0.504119    0.603203    0.515949    11.00000    0.03333    0.02710 =
         0.02181   -0.00248    0.00572    0.00438
N1    3    0.309745    0.724898    0.904001    11.00000    0.03879    0.03519 =
         0.02209   -0.00230    0.00469    0.00828
C5    1    0.430088    0.634049    0.648326    11.00000    0.02486    0.02644 =
         0.01810   -0.00130    0.00257    0.00623
C4    1    0.265884    0.460014    0.723505    11.00000    0.02945    0.02412 =
         0.02476   -0.00149    0.00393    0.00299
H4    2    0.188761    0.308752    0.690919    11.00000    0.03220
C2    1    0.525832    0.854703    0.701174    11.00000    0.03537    0.02666 =
         0.02619   -0.00001    0.00594    0.00322
H2    2    0.644377    0.983870    0.646726    11.00000    0.03255
C3    1    0.210884    0.514372    0.849443    11.00000    0.03300    0.03253 =
         0.02547    0.00241    0.00784    0.00478
H3    2    0.100484    0.397926    0.903674    11.00000    0.03728
C1    1    0.465118    0.890272    0.829593    11.00000    0.04218    0.02810 =
         0.02720   -0.00662    0.00321    0.00567
H1    2    0.537332    1.043688    0.871234    11.00000    0.04094
HKLF 4
 
REM  mcg1522lt_a.res in P-1
REM R1 =  0.0366 for     668 Fo > 4sig(Fo)  and  0.0477 for all     827 data
REM     81 parameters refined using      0 restraints
 
END  
     
WGHT      0.0513      0.0349 

REM Highest difference peak  0.171,  deepest hole -0.214,  1-sigma level  0.037
Q1    1   0.3640  0.7593  0.6644  11.00000  0.05    0.17
Q2    1   0.2371  0.7007  0.9930  11.00000  0.05    0.15
Q3    1   0.7236  1.0154  0.6035  11.00000  0.05    0.14
Q4    1   0.2500  0.5596  0.6632  11.00000  0.05    0.14
Q5    1   0.4158  0.7355  0.9972  11.00000  0.05    0.13
Q6    1   0.4652  0.6231  0.5986  11.00000  0.05    0.12
Q7    1  -0.0733  0.4218  0.9004  11.00000  0.05    0.12
Q8    1   0.4670  0.5341  0.7001  11.00000  0.05    0.12
Q9    1   0.5903  0.8238  0.7772  11.00000  0.05    0.12
Q10   1   0.6264  0.7276  0.6990  11.00000  0.05    0.11
Q11   1   0.1362  0.5059  0.9804  11.00000  0.05    0.11
Q12   1   0.8862  0.9349  0.6808  11.00000  0.05    0.11
Q13   1  -0.0174  0.1831  0.9553  11.00000  0.05    0.11
Q14   1   0.5833  0.9003  0.6841  11.00000  0.05    0.11
Q15   1   0.3758  0.8737  0.7377  11.00000  0.05    0.10
Q16   1   0.3632  0.4525  0.8105  11.00000  0.05    0.10
Q17   1   0.6941  1.0065  0.9235  11.00000  0.05    0.10
Q18   1   0.3460  0.3371  0.7227  11.00000  0.05    0.09
Q19   1   0.2293  0.7959  1.0602  11.00000  0.05    0.09
Q20   1   0.6909  0.7401  0.5127  11.00000  0.05    0.09

REM The information below was added by Olex2.
REM
REM R1 = 0.0366 for 668 Fo > 4sig(Fo) and 0.0477 for all 3229 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.17, deepest hole -0.21
REM Mean Shift 0, Max Shift 0.000.

REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0477
REM R1_gt = 0.0366
REM wR_ref = 0.1012
REM GOOF = 1.059
REM Shift_max = 0.000
REM Shift_mean = 0
REM Reflections_all = 3229
REM Reflections_gt = 668
REM Parameters = n/a
REM Hole = -0.21
REM Peak = 0.17
REM Flack = n/a

;
_cod_data_source_file            c6ce01674j2.cif
_cod_data_source_block           mcg1522lt
_cod_depositor_comments
;
The following automatic conversions were performed:

'_space_group_crystal_system' value 'Triclinic' changed to
'triclinic' 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.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' 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 7226336--7226343.cif.
;
_cod_database_code               7226342
_shelxl_version_number           2013-3
_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.
;
_olex2_refinement_description
;
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
N2 N 0.5041(3) 0.60320(19) 0.51595(11) 0.0273(4) Uani 1 1 d
N1 N 0.3097(3) 0.7249(2) 0.90400(12) 0.0317(4) Uani 1 1 d
C5 C 0.4301(4) 0.6340(2) 0.64833(13) 0.0229(4) Uani 1 1 d
C4 C 0.2659(4) 0.4600(3) 0.72351(14) 0.0262(4) Uani 1 1 d
H4 H 0.189(4) 0.309(3) 0.6909(15) 0.032(4) Uiso 1 1 d
C2 C 0.5258(4) 0.8547(3) 0.70117(15) 0.0294(4) Uani 1 1 d
H2 H 0.644(4) 0.984(3) 0.6467(14) 0.033(4) Uiso 1 1 d
C3 C 0.2109(4) 0.5144(3) 0.84944(15) 0.0301(4) Uani 1 1 d
H3 H 0.100(5) 0.398(3) 0.9037(15) 0.037(4) Uiso 1 1 d
C1 C 0.4651(4) 0.8903(3) 0.82959(15) 0.0325(4) Uani 1 1 d
H1 H 0.537(4) 1.044(3) 0.8712(16) 0.041(5) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N2 0.0333(7) 0.0271(7) 0.0218(7) -0.0025(5) 0.0057(5) 0.0044(6)
N1 0.0388(8) 0.0352(8) 0.0221(7) -0.0023(5) 0.0047(5) 0.0083(6)
C5 0.0249(7) 0.0264(8) 0.0181(8) -0.0013(6) 0.0026(6) 0.0062(6)
C4 0.0295(8) 0.0241(8) 0.0248(8) -0.0015(6) 0.0039(6) 0.0030(7)
C2 0.0354(8) 0.0267(9) 0.0262(9) 0.0000(6) 0.0059(7) 0.0032(7)
C3 0.0330(8) 0.0325(9) 0.0255(9) 0.0024(7) 0.0078(7) 0.0048(7)
C1 0.0422(9) 0.0281(9) 0.0272(9) -0.0066(7) 0.0032(7) 0.0057(7)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
N2 N2 C5 113.43(15) 2_666
C1 N1 C3 116.91(13) .
C4 C5 N2 124.37(13) .
C2 C5 N2 116.55(13) .
C2 C5 C4 119.07(13) .
C5 C4 H4 122.2(10) .
C3 C4 C5 118.17(14) .
C3 C4 H4 119.7(10) .
C5 C2 H2 119.8(9) .
C5 C2 C1 118.22(14) .
C1 C2 H2 122.0(9) .
N1 C3 C4 123.92(15) .
N1 C3 H3 116.0(9) .
C4 C3 H3 120.0(9) .
N1 C1 C2 123.67(14) .
N1 C1 H1 115.9(9) .
C2 C1 H1 120.4(9) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N2 N2 1.249(2) 2_666
N2 C5 1.4361(18) .
N1 C3 1.338(2) .
N1 C1 1.335(2) .
C5 C4 1.386(2) .
C5 C2 1.383(2) .
C4 H4 0.939(16) .
C4 C3 1.379(2) .
C2 H2 1.015(15) .
C2 C1 1.386(2) .
C3 H3 0.953(17) .
C1 H1 0.983(18) .
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
_geom_torsion_site_symmetry_1
N2 N2 C5 C4 -17.8(2) 2_666
N2 N2 C5 C2 163.46(15) 2_666
N2 C5 C4 C3 -179.91(12) .
N2 C5 C2 C1 -178.74(12) .
C5 C4 C3 N1 -0.7(2) .
C5 C2 C1 N1 -2.0(2) .
C4 C5 C2 C1 2.4(2) .
C2 C5 C4 C3 -1.2(2) .
C3 N1 C1 C2 0.3(2) .
C1 N1 C3 C4 1.1(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 238589
