#------------------------------------------------------------------------------
#$Date: 2019-02-26 05:47:57 +0200 (Tue, 26 Feb 2019) $
#$Revision: 213850 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/15/2021526.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_2021526
loop_
_publ_author_name
'Moreno-Fuquen, Rodolfo'
'Arango-Daravi\~na, Kevin'
'Becerra, Diana'
'Castillo, Juan-Carlos'
'Kennedy, Alan R.'
'Mac\'ias, Mario A.'
_publ_section_title
;
Catalyst- and solvent-free synthesis of
2-fluoro-N-(3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide
through a microwave-assisted Fries rearrangement: X-ray structural and
theoretical studies
;
_journal_coeditor_code YO3062
_journal_issue 3
_journal_name_full 'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi 10.1107/S2053229619002572
_journal_volume 75
_journal_year 2019
_chemical_formula_iupac 'C10 H9 F N4 O S'
_chemical_formula_moiety 'C10 H9 F N4 O S'
_chemical_formula_sum 'C10 H9 F N4 O S'
_chemical_formula_weight 252.27
_chemical_name_systematic
;
2-Fluoro-N-(3-methylsulfanyl-1H-1,2,4-triazol-5-yl)benzamide
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_Hall '-P 2yn'
_space_group_name_H-M_alt 'P 1 21/n 1'
_symmetry_space_group_name_Hall '-P 2yn'
_symmetry_space_group_name_H-M 'P 1 21/n 1'
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary iterative
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-2016/6
_cell_angle_alpha 90
_cell_angle_beta 94.12(2)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 5.0509(11)
_cell_length_b 26.640(5)
_cell_length_c 8.0251(16)
_cell_measurement_reflns_used 3138
_cell_measurement_temperature 298(2)
_cell_measurement_theta_max 24.7370
_cell_measurement_theta_min 3.9540
_cell_volume 1077.0(4)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2014)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2014)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2008)
;
_computing_publication_material
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SUPERFLIP (Palatinus & Chapuis, 2007)
;
_diffrn_ambient_temperature 298(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.3072
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type
;
Agilent SuperNova Dual Source diffractometer with an Atlas detector
;
_diffrn_measurement_method '\w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.080
_diffrn_reflns_av_unetI/netI 0.0848
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_k_max 33
_diffrn_reflns_limit_k_min -33
_diffrn_reflns_limit_l_max 9
_diffrn_reflns_limit_l_min -9
_diffrn_reflns_number 5060
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.770
_diffrn_reflns_theta_min 3.059
_diffrn_source 'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu 0.303
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.73397
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Agilent, 2014)
;
_exptl_crystal_colour colorless
_exptl_crystal_density_diffrn 1.556
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description parallelepiped
_exptl_crystal_F_000 520
_exptl_crystal_size_max 0.228
_exptl_crystal_size_mid 0.078
_exptl_crystal_size_min 0.053
_refine_diff_density_max 0.290
_refine_diff_density_min -0.375
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.103
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 165
_refine_ls_number_reflns 5060
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.103
_refine_ls_R_factor_all 0.1032
_refine_ls_R_factor_gt 0.0711
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1329P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2253
_refine_ls_wR_factor_ref 0.2371
_reflns_number_gt 3267
_reflns_number_total 5060
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file yo3062sup1.cif
_cod_data_source_block Compound_4
_cod_database_code 2021526
_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 0.934
_shelx_estimated_absorpt_t_max 0.984
_shelx_hkl_file
;
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0 0 -8 387.835 47.5854 -2
0 0 8 387.835 47.5854 1
0 -1 2 29246.2 100.960 -2
0 -1 -2 29246.2 100.960 1
0 1 -3 4413.38 36.2120 -2
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0 1 -4 14.7377 13.1092 -2
0 1 4 14.7377 13.1092 1
0 1 5 167.359 16.6315 -2
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0 -1 -8 46.3252 29.0266 -2
0 -1 8 46.3252 29.0266 1
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0 1 -9 0.53173 43.1234 1
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0 2 4 163.682 15.1402 1
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0 2 6 2972.58 42.1795 -2
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0 2 -7 107.385 23.4807 -2
0 2 7 107.385 23.4807 1
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0 2 -9 29.8326 43.1040 -2
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0 -3 -1 9541.21 63.9523 -2
0 -3 1 9541.21 63.9523 1
0 3 -2 17767.2 58.8311 -2
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0 3 -3 411.056 15.1188 -2
0 3 3 411.056 15.1188 1
0 3 4 135.437 15.0703 -2
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0 3 -5 278.346 17.5812 -2
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0 -3 -6 343.219 21.2010 -2
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0 -3 8 331.344 33.0292 1
0 3 -9 320.000 48.1558 -2
0 3 9 320.000 48.1558 1
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0 4 2 4951.30 32.2339 -2
0 4 -2 4951.30 32.2339 1
0 -4 3 19630.0 69.8311 -2
0 -4 -3 19630.0 69.8311 1
0 4 -4 17558.2 74.7371 -2
0 4 4 17558.2 74.7371 1
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0 -4 5 199.554 16.4590 1
0 4 -6 13.4152 17.2610 -2
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0 -4 -7 1119.26 36.7151 1
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0 -5 1 5238.59 33.3480 1
0 -5 2 18122.1 478.803 1
0 5 -2 20550.2 62.4256 -2
0 5 2 20550.2 62.4256 1
0 5 -3 13486.5 64.3512 -2
0 5 3 13486.5 64.3512 1
0 -5 -4 699.968 18.8259 -2
0 -5 4 699.968 18.8259 1
0 5 -5 1233.53 26.7414 -2
0 5 5 1233.53 26.7414 1
0 -5 6 406.962 22.5018 -2
0 -5 -6 406.962 22.5018 1
0 -5 7 168.192 24.3145 -2
0 -5 -7 168.192 24.3145 1
0 5 -8 51.3720 28.9448 -2
0 5 8 51.3720 28.9448 1
0 -5 9 25.1404 47.6363 -2
0 -5 -9 25.1404 47.6363 1
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0 -6 -3 10245.4 53.7681 1
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0 6 -4 2428.99 36.5483 1
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0 -6 -5 3262.12 43.2072 1
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0 6 7 54.1433 27.4394 1
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0 -6 -8 20.3166 39.8414 1
0 -6 -9 31.9169 48.2853 -2
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0 -7 -1 934.163 16.0550 1
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0 7 -3 1982.53 28.5934 1
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0 -7 -4 329.955 19.2800 1
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0 7 5 6276.61 58.7738 1
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0 -7 -7 661.907 41.0810 -2
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0 7 -8 155.490 40.2322 1
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0 7 9 92.7443 58.8531 1
0 8 0 1902.61 30.3070 1
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0 -8 0 2997.52 45.4668 1
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0 12 2 4102.76 45.4617 1
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0 12 3 92.9870 18.7830 1
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0 -14 -4 598.596 25.8051 1
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0 -14 -6 2255.46 57.0573 1
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0 -18 -5 155.536 42.3287 1
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-2 10 5 92.5730 26.4318 2
-2 10 4 386.908 26.2622 2
-2 -10 3 102.927 18.1701 2
-2 10 2 374.386 31.0028 2
-2 10 1 5525.11 82.6553 2
-2 10 0 10.8627 13.7084 2
-2 10 -1 455.821 22.9561 2
2 -10 6 27.2047 17.0664 2
-2 -10 -7 65.3649 61.2673 2
-2 -11 6 4.66106 13.2031 2
-2 -11 5 206.285 34.6409 2
-2 11 3 167.166 53.4417 2
-2 11 2 8.90004 21.3712 2
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-2 11 0 45.2967 15.7195 2
-2 11 -1 1136.16 30.1315 2
2 -11 2 144.674 65.2809 2
-2 12 7 127.443 59.0768 2
-2 -12 6 0.14313 15.5222 2
-2 -12 5 74.3294 27.5723 2
2 -12 -4 12.8752 75.3142 2
2 -12 -3 617.563 92.7703 2
2 -12 -2 308.437 30.4621 2
-2 12 1 2101.14 43.7705 2
-2 12 0 1317.72 37.3690 2
-2 -12 -3 328.394 38.7170 2
2 -12 4 81.1167 27.5054 2
2 -12 5 360.006 36.9608 2
2 -12 6 143.901 38.1400 2
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2 -13 3 151.019 15.6334 2
2 -13 5 164.119 23.1339 2
2 -13 6 407.184 51.3189 2
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-2 -17 3 29.8040 26.5482 2
2 -17 -2 385.277 22.7690 2
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-2 17 0 524.072 24.4510 2
-2 -17 -1 70.8402 30.9541 2
-2 -17 -2 2934.25 84.1672 2
-2 -17 -3 264.323 32.8139 2
2 -17 4 197.286 96.9097 2
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-2 -18 5 63.7205 18.1890 2
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2 -18 -3 4.70193 21.7939 2
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2 -18 -1 762.174 29.5862 2
-2 18 0 582.638 24.9270 2
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-2 18 -2 165.780 27.0757 2
2 -18 3 271.447 40.6033 2
-2 -18 -4 82.1335 41.3944 2
-2 -18 -5 6.46108 77.1277 2
-2 -19 5-5.54723 22.9245 2
-2 -19 4 242.349 22.1428 2
-2 -19 3 13.9540 23.6743 2
2 -19 -2 194.095 27.4454 2
2 -19 -1 65.4597 23.0761 2
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2 -20 -2 111.554 28.3223 2
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2 -20 0 135.547 22.0158 2
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-2 -20 -2 325.129 31.4098 2
2 -20 3 30.3022 25.2277 2
-2 -20 -4 115.652 28.8278 2
-2 -20 -7-18.4173 108.995 2
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2 21 -4-63.8376 105.591 2
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-2 -21 -2 334.245 26.1757 2
2 -21 3 10.7377 16.9935 2
2 -21 4 43.4229 39.0928 2
2 22 -6 25.4622 122.298 2
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-2 22 3 66.3085 26.7922 2
2 -22 -2 7.58138 24.2772 2
2 -22 -1 770.280 34.9012 2
-2 22 0 18.5315 19.2497 2
-2 22 -1 58.4660 13.5288 2
2 -22 2 231.433 42.4729 2
2 -22 3 23.4627 24.0516 2
2 -22 4 34.7311 50.3754 2
2 -22 5 137.180 105.198 2
2 23 -6 11.9442 134.706 2
2 23 -5 14.8610 117.869 2
2 23 -4 171.400 128.158 2
2 -23 -3 62.2809 31.8042 2
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-2 23 1 58.7140 25.2194 2
2 -23 0 142.151 22.1225 2
2 -23 1 155.160 16.3146 2
2 -23 2 181.079 32.1604 2
2 -23 3 27.0119 33.4159 2
2 -23 4 97.6953 53.9662 2
2 -23 5 369.268 136.391 2
-2 -23 -6-4.54006 105.778 2
2 24 -6 28.4115 140.884 2
2 24 -5 32.2347 128.128 2
2 24 -4-10.7083 128.352 2
-2 -24 3 313.464 56.6496 2
-2 -24 2 327.429 37.4196 2
2 -24 -1 54.4504 27.7419 2
-2 24 0 8.91427 20.8115 2
2 -24 1 34.3999 16.5790 2
2 -24 2 95.7493 38.5891 2
-2 -24 -3 75.4877 32.6520 2
-2 -24 -4 220.341 50.7611 2
2 -24 5 29.4699 121.327 2
2 25 -5 14.0842 135.594 2
2 -25 -4 144.602 84.7965 2
-2 -25 3 100.248 48.1208 2
-2 -25 2 9.01900 29.1232 2
-2 -25 1 2.33158 40.0512 2
-2 25 0 10.8659 30.1937 2
2 -25 1 23.0260 34.5632 2
2 -25 2 20.0936 37.9007 2
2 -25 3 36.8310 56.6456 2
2 -25 4 78.1748 70.4410 2
2 -25 5 236.718 125.754 2
2 26 -5 54.4025 147.570 2
2 26 -4 22.5884 132.363 2
2 26 -3 45.8069 78.0919 2
-2 -26 2 68.4028 49.5501 2
-2 26 1 46.8319 39.2714 2
-2 -26 0 72.9298 26.2484 2
2 -26 1 195.807 42.8420 2
2 -26 2 9.61760 46.2743 2
-2 -26 -3 259.879 47.3332 2
2 -26 4 29.2543 67.9816 2
2 -26 5 187.545 120.539 2
-2 -27 5 76.1022 212.674 2
2 27 -4 57.5596 134.580 2
2 -27 -3 12.5763 50.6433 2
2 -27 -2 85.6314 62.6100 2
-2 27 1 33.0128 46.7290 2
-2 -27 0-4.69851 31.4471 2
2 -27 1 13.2937 36.2252 2
2 -27 2-7.31583 57.2160 2
2 -27 3 86.6544 64.2487 2
2 -27 4 9.46530 55.5553 2
2 28 -4-16.5410 135.557 2
2 28 -3 57.7658 131.140 2
2 -28 -2-18.6870 49.3559 2
-2 28 1 58.2749 44.0944 2
-2 -28 0-9.43645 38.9152 2
2 -28 1 142.562 38.5619 2
2 -28 2 29.9904 50.2823 2
2 -28 3 183.079 57.6980 2
2 -28 4-17.5713 76.3726 2
-2 29 4 31.6706 87.2325 2
2 29 -3 43.4610 141.019 2
2 29 -2 78.2372 93.0220 2
-2 29 1-6.12698 39.7473 2
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2 -29 1 44.4966 49.6628 2
2 -29 2 131.418 62.2887 2
2 -29 3 72.2859 65.2499 2
2 -30 -3 74.8604 121.925 2
2 -30 -2 2.48970 47.7741 2
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2 -30 0 6.29665 45.6531 2
2 -30 1 169.561 48.7292 2
2 -30 2 19.4795 55.5431 2
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-3 1 4 268.472 41.9710 2
-3 1 2 331.342 68.5193 2
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3 -1 4 598.598 42.4753 2
3 -1 6 184.280 57.0701 2
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-3 -4 5 530.351 52.4773 2
-3 6 6 324.089 45.3622 2
-3 7 9 23.4043 105.114 2
-3 7 8-32.9435 87.1472 2
-3 7 6 106.505 39.0438 2
-3 8 8-6.70658 94.1227 2
-3 8 6 29.2406 35.8658 2
-3 -8 -8 162.164 164.850 2
-3 9 6 447.216 49.0793 2
-3 -9 -8-6.00045 87.6909 2
-3 10 6 54.9351 35.4630 2
3 -12 -6-37.4535 105.074 2
-3 12 5 236.023 18.0060 2
-3 12 4 85.3471 19.6870 2
3 -13 -6 231.516 128.374 2
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3 -14 -6 39.6561 110.092 2
3 -14 -5 87.3630 61.4018 2
3 14 -4 254.956 44.5233 2
-3 15 8-164.964 124.973 2
-3 15 7 57.3538 84.8809 2
3 -15 -6 27.1069 105.335 2
3 -15 -5 19.3704 96.4754 2
-3 -15 4 514.988 52.5305 2
-3 15 3 57.6133 23.4773 2
-3 15 2 220.266 73.6055 2
-3 15 1 5.76661 51.7732 2
3 15 0 856.201 168.812 2
-3 -15 -5 71.1514 52.4487 2
-3 16 7 68.7261 87.1777 2
3 -16 -6 51.4936 108.793 2
3 16 -5 430.084 91.0090 2
3 16 -4 86.0859 42.1679 2
3 -16 -3-25.9787 69.2560 2
-3 16 2 1241.25 114.792 2
-3 16 1 508.617 72.0505 2
3 -16 4 106.205 20.6691 2
-3 -16 -7 106.354 89.3697 2
-3 17 7 4.29589 85.2136 2
3 -17 -6-17.0713 108.785 2
3 -17 -5 53.8130 96.3942 2
3 17 -4 24.2772 44.7992 2
-3 17 3 182.207 56.5656 2
-3 17 2 1096.32 112.048 2
-3 -17 1 378.670 48.2347 2
-3 -17 -3 25.1410 61.1853 2
-3 18 7 35.7756 68.4796 2
3 18 -6-3.66959 82.2822 2
3 -18 -5 87.8185 100.631 2
3 18 -4 18.2739 46.9916 2
-3 18 3 357.309 65.6248 2
-3 18 2 269.271 51.5110 2
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3 19 -6 32.6059 88.3618 2
3 19 -5 45.5367 76.7683 2
3 19 -4 82.3328 64.5199 2
-3 19 3 155.795 47.0803 2
-3 19 2-18.1146 39.4857 2
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-3 -19 -3 13.6404 61.5559 2
3 -20 -6 21.7064 115.443 2
3 20 -5 66.0547 78.7539 2
3 20 -4 59.6336 123.200 2
-3 20 3 385.635 53.6025 2
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-3 -20 1 1410.78 75.3217 2
-3 -20 0 77.4146 159.297 2
3 -20 1 119.326 78.6511 2
3 -20 3 117.476 52.6424 2
-3 -20 -6-8.18559 140.810 2
3 21 -6 72.4389 71.8208 2
3 21 -5-38.0188 130.592 2
-3 -21 4 20.0767 55.4109 2
-3 -21 3 149.099 78.9569 2
-3 21 2 471.803 51.1367 2
-3 21 1 443.552 58.4014 2
-3 -21 0 197.197 173.511 2
3 22 -5 27.2955 134.992 2
-3 -22 4 95.3070 59.1740 2
-3 -22 3 600.496 58.7978 2
-3 -22 2 22.2361 50.6371 2
-3 -22 1 30.6643 40.1565 2
-3 -22 0 34.6629 42.7252 2
-3 -22 -1 275.122 63.1468 2
3 -22 2 271.016 97.0662 2
3 23 -5-26.7686 86.8322 2
3 23 -4 78.7031 86.0700 2
-3 -23 3 2.70985 45.2369 2
-3 -23 2 55.9856 42.6820 2
-3 -23 1 153.501 45.9800 2
-3 -23 0 515.441 70.0423 2
-3 -23 -1 232.603 56.5868 2
3 -23 2 51.0305 59.4299 2
3 -23 3 144.912 97.8431 2
3 -23 4 164.365 101.546 2
3 24 -5 90.7269 149.910 2
3 24 -4-1.50006 85.1999 2
-3 -24 3 9.41544 45.8591 2
-3 -24 2 55.9394 60.5500 2
-3 -24 1 56.4430 47.3569 2
-3 -24 0 10.4740 56.9773 2
-3 -24 -1 263.447 50.0358 2
3 -24 2 59.1888 46.4598 2
3 -24 3 344.850 111.575 2
3 25 -4 36.2162 88.8058 2
-3 -25 3 13.4895 46.9026 2
-3 -25 2 156.045 47.6208 2
-3 -25 1 319.309 60.4034 2
-3 -25 0 16.9785 52.7674 2
-3 -25 -1 10.9192 56.1137 2
3 -25 2 135.871 44.9517 2
3 -25 3 61.4386 98.9954 2
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3 26 -4 78.4740 146.104 2
-3 -26 3 10.1772 50.0634 2
3 26 -2 36.9310 58.1392 2
-3 -26 1 170.851 53.1903 2
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3 26 1 134.553 50.2341 2
3 -26 2 48.3947 70.5020 2
3 -26 3 60.6383 82.5433 2
3 27 -3 25.8315 70.0853 2
-3 -27 2-20.7593 48.3964 2
3 27 -1 11.9487 63.4521 2
3 27 0 415.003 73.3388 2
3 -27 1-4.96487 51.8827 2
3 -27 2 24.6725 54.6693 2
3 -27 3 85.5167 89.3966 2
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3 -28 1-0.40284 45.9885 2
3 -28 2 79.5124 52.2739 2
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3 -29 1-27.6307 86.9463 2
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4 -1 -3 179.530 57.5631 2
4 -1 -1 179.865 42.3510 2
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4 -1 3 205.047 47.8739 2
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4 20 -5 10.7905 59.1058 2
4 -20 -4 51.7107 84.9374 2
4 -21 -5 22.1971 104.938 2
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-4 -24 -2 48.8501 64.5255 2
-4 -25 2 122.137 99.5706 2
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-4 -25 0 25.7957 52.0596 2
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5 -1 -6 10.6467 89.4215 2
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5 -1 -2 106.714 66.2508 2
5 -1 0 357.125 69.0753 2
5 -1 2 149.909 60.9416 2
-5 1 -4 20.8141 93.8927 2
-5 -7 -5 12.3071 190.027 2
-5 -8 6-109.163 205.726 2
-5 -8 -5 24.6038 108.811 2
-5 -13 5 10.1807 87.3640 2
5 13 4-20.5264 98.2603 2
-5 -16 4 20.4342 100.143 2
-5 -16 -3 57.5621 76.4297 2
-5 -18 3 137.950 101.976 2
-5 -18 -2 82.0665 78.9277 2
-5 -19 2 25.6825 100.682 2
5 19 1 202.034 73.6032 2
-5 -20 1 30.5280 132.806 2
-5 -20 0-143.786 157.655 2
-5 21 1 35.5746 138.844 2
-5 21 0 106.229 137.997 2
-6 1 3 63.1211 87.9233 2
6 -1 -1 7.74393 73.5508 2
6 -1 1 13.2999 74.5533 2
-6 -4 -2 308.256 209.961 2
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;
_shelx_hkl_checksum 67896
_shelx_res_file
;
TITL 2016Uniandes038_Mo_0911 in P2/m
shelxs_twin1_hklf5_2.res
created by SHELXL-2016/6 at 09:54:07 on 21-Nov-2016
REM TITL 2016Uniandes038_Mo_0911 in P2/m
CELL 0.71073 5.05093 26.63961 8.02514 90.00000 94.11950 90.00000
ZERR 4 0.0011 0.0048 0.0016 0.0000 0.0209 0.0000
LATT 1
SYMM X+0.500,-Y+0.500,Z+0.500
SFAC C H N O S F
UNIT 40 36 16 4 4 4
LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
L.S. 10
FMAP 2
PLAN 5
TEMP 25
SIZE 0.053 0.078 0.228
ACTA
CONF
HTAB
BOND $H
HTAB N4 F1
EQIV $1 x-1, y, z
HTAB N4 O1_$1
HTAB N2 O1
EQIV $2 x+1, y, z
HTAB N2 N3_$2
MERG 0
WGHT 0.132900
BASF 0.23244 0.24769
FVAR 2.44743
S1 5 0.147663 0.275857 0.000680 11.00000 0.02790 0.03744 =
0.06878 -0.00998 -0.00133 -0.00451
F1 6 0.166029 0.538948 0.103208 11.00000 0.04399 0.04980 =
0.05488 0.00327 -0.01631 0.00296
H1 2 0.222599 0.461067 0.206427 11.00000 0.06429
O1 4 0.826543 0.462212 0.280480 11.00000 0.02529 0.04215 =
0.05283 -0.00459 -0.00317 0.00325
N1 3 0.588250 0.326637 0.108285 11.00000 0.02704 0.03296 =
0.04741 -0.00064 0.00400 -0.00108
C1 1 0.419489 0.235049 -0.041744 11.00000 0.03971 0.04251 =
0.08156 -0.01947 0.00908 0.00080
AFIX 137
H1A 2 0.351155 0.204771 -0.093496 11.00000 -1.50000
H1B 2 0.519322 0.226953 0.061054 11.00000 -1.50000
H1C 2 0.532742 0.251692 -0.115383 11.00000 -1.50000
AFIX 0
C2 1 0.326990 0.327163 0.083825 11.00000 0.01896 0.03498 =
0.03682 0.00135 0.00113 0.00042
N2 3 0.640819 0.374618 0.162331 11.00000 0.02011 0.03378 =
0.04920 -0.00236 0.00239 0.00074
C3 1 0.415622 0.400492 0.163556 11.00000 0.02352 0.03254 =
0.03369 0.00049 -0.00088 0.00437
N3 3 0.210187 0.371965 0.116813 11.00000 0.02365 0.03338 =
0.05073 -0.00253 0.00474 -0.00163
C4 1 0.604140 0.480029 0.255854 11.00000 0.02646 0.03533 =
0.03083 -0.00162 0.00485 -0.00285
H4 2 0.807851 0.385678 0.187489 11.00000 0.10645
N4 3 0.396520 0.450706 0.199165 11.00000 0.01753 0.03596 =
0.04963 -0.00103 0.00504 0.00299
C6 1 0.344515 0.561834 0.212666 11.00000 0.03672 0.03691 =
0.03578 0.00262 0.00975 -0.00276
C5 1 0.551357 0.533875 0.286397 11.00000 0.02840 0.03529 =
0.02825 0.00199 0.00599 -0.00151
C7 1 0.314236 0.612257 0.236560 11.00000 0.04384 0.04409 =
0.04817 0.00959 0.01456 0.00695
AFIX 43
H7 2 0.173297 0.629657 0.182589 11.00000 -1.20000
AFIX 0
C9 1 0.703465 0.609968 0.422264 11.00000 0.05577 0.04485 =
0.04895 -0.00648 0.00711 -0.01193
AFIX 43
H9 2 0.824367 0.626244 0.496651 11.00000 -1.20000
AFIX 0
C8 1 0.498866 0.636644 0.343127 11.00000 0.06527 0.03560 =
0.05766 -0.00206 0.02096 -0.00156
AFIX 43
H8 2 0.484520 0.670992 0.361139 11.00000 -1.20000
AFIX 0
C10 1 0.731753 0.559952 0.393261 11.00000 0.03342 0.04539 =
0.03782 -0.00689 0.00434 -0.00429
AFIX 43
H10 2 0.874783 0.542851 0.446041 11.00000 -1.20000
REM #####
REM #####
AFIX 0
HKLF 5
REM 2016Uniandes038_Mo_0911 in P2/m
REM R1 = 0.0711 for 3267 Fo > 4sig(Fo) and 0.1032 for all 5060 data
REM 165 parameters refined using 0 restraints
END
WGHT 0.1329 0.0000
REM Instructions for potential hydrogen bonds
HTAB N4 F1
HTAB N4 O1_$1
HTAB N2 O1
HTAB N2 N3_$2
REM Highest difference peak 0.290, deepest hole -0.375, 1-sigma level 0.078
Q1 1 0.5753 0.5109 0.2638 11.00000 0.05 0.29
Q2 1 0.9637 0.6283 0.6349 11.00000 0.05 0.28
Q3 1 0.2307 0.2697 0.1234 11.00000 0.05 0.28
Q4 1 0.0918 0.3781 -0.0072 11.00000 0.05 0.28
Q5 1 0.0000 0.5000 0.0000 10.50000 0.05 0.28
;
_shelx_res_checksum 25207
loop_
_space_group_symop_operation_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_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
S S1 0.1477(4) 0.27586(4) 0.0007(2) 0.0449(5) Uani d 1
F F1 0.1660(7) 0.53895(10) 0.1032(4) 0.0505(9) Uani d 1
H H1 0.223(15) 0.461(2) 0.206(8) 0.06(2) Uiso d 1
O O1 0.8265(8) 0.46221(12) 0.2805(5) 0.0404(10) Uani d 1
N N1 0.5883(9) 0.32664(13) 0.1083(6) 0.0357(11) Uani d 1
C C1 0.4195(13) 0.23505(19) -0.0417(9) 0.0544(18) Uani d 1
H H1A 0.351155 0.204771 -0.093496 0.082 Uiso calc 1
H H1B 0.519322 0.226953 0.061054 0.082 Uiso calc 1
H H1C 0.532742 0.251692 -0.115383 0.082 Uiso calc 1
C C2 0.3270(11) 0.32716(16) 0.0838(6) 0.0303(11) Uani d 1
N N2 0.6408(10) 0.37462(14) 0.1623(6) 0.0344(11) Uani d 1
C C3 0.4156(10) 0.40049(16) 0.1636(6) 0.0301(12) Uani d 1
N N3 0.2102(9) 0.37196(14) 0.1168(6) 0.0358(11) Uani d 1
C C4 0.6041(11) 0.48003(17) 0.2559(6) 0.0307(12) Uani d 1
H H4 0.81(2) 0.386(3) 0.187(12) 0.11(3) Uiso d 1
N N4 0.3965(9) 0.45071(14) 0.1992(6) 0.0342(10) Uani d 1
C C6 0.3445(12) 0.56183(17) 0.2127(7) 0.0361(13) Uani d 1
C C5 0.5514(10) 0.53388(16) 0.2864(6) 0.0305(12) Uani d 1
C C7 0.3142(13) 0.61226(18) 0.2366(7) 0.0448(15) Uani d 1
H H7 0.173297 0.629657 0.182589 0.054 Uiso calc 1
C C9 0.7035(14) 0.60997(19) 0.4223(8) 0.0497(16) Uani d 1
H H9 0.824367 0.626244 0.496651 0.060 Uiso calc 1
C C8 0.4989(14) 0.63664(19) 0.3431(8) 0.0520(17) Uani d 1
H H8 0.484520 0.670992 0.361139 0.062 Uiso calc 1
C C10 0.7318(12) 0.55995(18) 0.3933(7) 0.0388(13) Uani d 1
H H10 0.874783 0.542851 0.446041 0.047 Uiso calc 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S1 0.0279(8) 0.0374(7) 0.0688(11) -0.0045(6) -0.0013(7) -0.0100(6)
F1 0.044(2) 0.0498(17) 0.055(2) 0.0030(15) -0.0163(17) 0.0033(15)
O1 0.025(2) 0.0422(19) 0.053(2) 0.0033(16) -0.0032(18) -0.0046(16)
N1 0.027(3) 0.033(2) 0.047(3) -0.0011(18) 0.004(2) -0.0006(18)
C1 0.040(4) 0.043(3) 0.082(5) 0.001(3) 0.009(4) -0.019(3)
C2 0.019(3) 0.035(2) 0.037(3) 0.000(2) 0.001(2) 0.001(2)
N2 0.020(3) 0.034(2) 0.049(3) 0.0007(19) 0.002(2) -0.0024(18)
C3 0.024(3) 0.033(2) 0.034(3) 0.004(2) -0.001(2) 0.000(2)
N3 0.024(3) 0.033(2) 0.051(3) -0.0016(18) 0.005(2) -0.0025(19)
C4 0.026(3) 0.035(2) 0.031(3) -0.003(2) 0.005(2) -0.002(2)
N4 0.018(3) 0.036(2) 0.050(3) 0.0030(19) 0.005(2) -0.0010(18)
C6 0.037(4) 0.037(3) 0.036(3) -0.003(2) 0.010(3) 0.003(2)
C5 0.028(3) 0.035(2) 0.028(3) -0.002(2) 0.006(2) 0.002(2)
C7 0.044(4) 0.044(3) 0.048(4) 0.007(3) 0.015(3) 0.010(2)
C9 0.056(5) 0.045(3) 0.049(4) -0.012(3) 0.007(3) -0.006(3)
C8 0.065(5) 0.036(3) 0.058(4) -0.002(3) 0.021(3) -0.002(3)
C10 0.033(4) 0.045(3) 0.038(3) -0.004(2) 0.004(3) -0.007(2)
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'
F F 0.0171 0.0103 '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 S1 C1 99.4(3)
C2 N1 N2 101.9(4)
S1 C1 H1A 109.5
S1 C1 H1B 109.5
H1A C1 H1B 109.5
S1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
N1 C2 N3 114.9(4)
N1 C2 S1 122.3(3)
N3 C2 S1 122.6(4)
C3 N2 N1 109.8(4)
C3 N2 H4 128(5)
N1 N2 H4 122(5)
N3 C3 N2 110.8(4)
N3 C3 N4 123.7(5)
N2 C3 N4 125.4(5)
C3 N3 C2 102.5(4)
O1 C4 N4 120.6(4)
O1 C4 C5 121.5(5)
N4 C4 C5 117.9(5)
C4 N4 C3 124.4(5)
C4 N4 H1 121(4)
C3 N4 H1 113(4)
F1 C6 C7 117.2(5)
F1 C6 C5 118.8(4)
C7 C6 C5 124.0(5)
C6 C5 C10 115.9(4)
C6 C5 C4 126.2(5)
C10 C5 C4 117.9(5)
C6 C7 C8 118.1(6)
C6 C7 H7 120.9
C8 C7 H7 120.9
C10 C9 C8 120.8(6)
C10 C9 H9 119.6
C8 C9 H9 119.6
C9 C8 C7 119.7(5)
C9 C8 H8 120.1
C7 C8 H8 120.1
C9 C10 C5 121.4(5)
C9 C10 H10 119.3
C5 C10 H10 119.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 C2 1.746(5)
S1 C1 1.803(6)
F1 C6 1.357(6)
O1 C4 1.222(6)
N1 C2 1.320(7)
N1 N2 1.370(6)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 N3 1.366(6)
N2 C3 1.331(7)
N2 H4 0.90(10)
C3 N3 1.319(7)
C3 N4 1.373(6)
C4 N4 1.360(7)
C4 C5 1.483(7)
N4 H1 0.93(7)
C6 C7 1.367(7)
C6 C5 1.381(7)
C5 C10 1.391(7)
C7 C8 1.381(9)
C7 H7 0.9300
C9 C10 1.362(7)
C9 C8 1.372(9)
C9 H9 0.9300
C8 H8 0.9300
C10 H10 0.9300
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
N4 H1 F1 . 0.92(7) 2.25(6) 2.710(5) 111(5)
N2 H4 O1 . 0.92(10) 2.16(8) 2.664(5) 114(7)
N4 H1 O1 1_455 0.92(7) 2.13(8) 3.013(6) 159(5)
N2 H4 N3 1_655 0.92(10) 2.17(10) 2.926(7) 140(8)
C10 H10 O1 3_766 0.93 2.58 3.367(7) 143
C1 H1A N1 2_454 0.96 2.78 3.566(8) 140
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
N2 N1 C2 N3 0.6(6)
N2 N1 C2 S1 176.0(4)
C1 S1 C2 N1 -3.9(5)
C1 S1 C2 N3 171.2(4)
C2 N1 N2 C3 -1.3(5)
N1 N2 C3 N3 1.6(6)
N1 N2 C3 N4 -175.0(4)
N2 C3 N3 C2 -1.2(5)
N4 C3 N3 C2 175.5(5)
N1 C2 N3 C3 0.3(6)
S1 C2 N3 C3 -175.0(4)
O1 C4 N4 C3 -0.8(8)
C5 C4 N4 C3 179.2(4)
N3 C3 N4 C4 176.4(5)
N2 C3 N4 C4 -7.4(8)
F1 C6 C5 C10 178.1(5)
C7 C6 C5 C10 1.4(8)
F1 C6 C5 C4 1.2(8)
C7 C6 C5 C4 -175.5(5)
O1 C4 C5 C6 155.9(5)
N4 C4 C5 C6 -24.1(7)
O1 C4 C5 C10 -21.0(7)
N4 C4 C5 C10 159.0(5)
F1 C6 C7 C8 -177.9(5)
C5 C6 C7 C8 -1.2(8)
C10 C9 C8 C7 2.0(9)
C6 C7 C8 C9 -0.6(9)
C8 C9 C10 C5 -1.7(9)
C6 C5 C10 C9 0.0(8)
C4 C5 C10 C9 177.2(5)
_cod_database_fobs_code 2021526