#------------------------------------------------------------------------------
#$Date: 2022-09-23 05:09:46 +0300 (Fri, 23 Sep 2022) $
#$Revision: 278105 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244179.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_2244179
loop_
_publ_author_name
'Archana, Sreeramapura D.'
'Kiran Kumar, Haruvegowda'
'Shankara Prasad, Holehundi J.'
'Yathirajan, Hemmige S.'
'Parkin, Sean'
_publ_section_title
;
Synthesis and crystal structures of 1-benzoyl-4-(4-nitrophenyl)piperazine
and 1-(4-bromobenzoyl)-4-phenylpiperazine at 90K
;
_journal_coeditor_code TX2058
_journal_issue 10
_journal_name_full 'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi 10.1107/S2056989022009008
_journal_volume 78
_journal_year 2022
_chemical_absolute_configuration ad
_chemical_formula_iupac 'C17 H17 Br N2 O'
_chemical_formula_moiety 'C17 H17 Br N2 O'
_chemical_formula_sum 'C17 H17 Br N2 O'
_chemical_formula_weight 345.23
_chemical_name_systematic
;
1-(4-Bromobenzoyl)-4-phenylpiperazine
;
_space_group_crystal_system monoclinic
_space_group_IT_number 4
_space_group_name_Hall 'P 2yb'
_space_group_name_H-M_alt 'P 1 21 1'
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method 'SHELXL-2019/2 and CIFFIX'
_cell_angle_alpha 90
_cell_angle_beta 98.6250(10)
_cell_angle_gamma 90
_cell_formula_units_Z 2
_cell_length_a 7.5162(3)
_cell_length_b 6.1125(2)
_cell_length_c 15.7249(5)
_cell_measurement_reflns_used 9856
_cell_measurement_temperature 90.0(2)
_cell_measurement_theta_max 27.47
_cell_measurement_theta_min 2.62
_cell_volume 714.28(4)
_computing_cell_refinement
;
APEX3 (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
APEX3 (Bruker, 2016)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and publCIF (Westrip,
2010)
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature 90.0(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'Bruker D8 Venture dual source'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0650
_diffrn_reflns_av_unetI/netI 0.0367
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -9
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 20
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_number 6918
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.504
_diffrn_reflns_theta_min 2.620
_diffrn_source microsource
_exptl_absorpt_coefficient_mu 2.878
_exptl_absorpt_correction_T_max 0.806
_exptl_absorpt_correction_T_min 0.568
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(TWINABS; Sheldrick, 2012)
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 1.605
_exptl_crystal_description 'slab cut from lath'
_exptl_crystal_F_000 352
_exptl_crystal_size_max 0.350
_exptl_crystal_size_mid 0.200
_exptl_crystal_size_min 0.060
_refine_diff_density_max 0.293
_refine_diff_density_min -0.222
_refine_ls_abs_structure_details
;
Flack x determined using 1306 quotients
[(I^+^)-(I^-^)]/[(I^+^)+(I^-^)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack 0.012(4)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.044
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 191
_refine_ls_number_reflns 6918
_refine_ls_number_restraints 1
_refine_ls_restrained_S_all 1.044
_refine_ls_R_factor_all 0.0266
_refine_ls_R_factor_gt 0.0225
_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^)+(0.0158P)^2^+0.0999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0479
_refine_ls_wR_factor_ref 0.0491
_reflns_number_gt 6410
_reflns_number_total 6918
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file tx2058sup1.cif
_cod_data_source_block II
_cod_original_sg_symbol_H-M 'P 21'
_cod_database_code 2244179
_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 0.432
_shelx_estimated_absorpt_t_max 0.846
_shelx_hkl_file
;
1 0 0 201.065 4.87581 2
1 0 0 422.570 17.8935 -2
1 0 0 422.570 17.8935 1
1 0 0 224.094 5.78314 1
2 0 0 4992.35 200.349 -2
2 0 0 4992.35 200.349 1
2 0 0 2612.32 53.3638 1
2 0 0 2599.53 53.1178 2
3 0 0 4.96110 1.23779 2
3 0 0 5.04421 1.29799 1
4 0 0 190.307 4.98747 1
4 0 0 178.386 4.53211 2
5 0 0 933.898 17.7409 1
5 0 0 921.959 18.1734 2
6 0 0 430.196 9.79697 2
6 0 0 449.357 10.3396 1
7 0 0 409.487 12.2985 1
7 0 0 368.533 11.2976 2
8 0 0 103.086 7.76715 2
8 0 0 110.309 7.58909 1
9 0 0 254.907 11.8050 2
9 0 0 245.640 12.7137 1
0 -1 0 0.16635 0.41368 2
0 -1 0 0.13423 0.36899 1
0 1 0 0.63691 0.50509 2
0 1 0 0.86699 0.45681 1
0 1 0 1.32433 0.95269 -2
0 1 0 1.32433 0.95269 1
-1 -1 0 6130.51 350.543 1
-2 -1 0 2774.50 62.8419 1
-2 -1 0 5240.33 235.030 -2
-2 -1 0 5240.33 235.030 1
-2 -1 0 2652.79 52.8095 2
2 1 0 3105.95 85.7246 1
2 1 0 2980.21 90.9829 2
2 1 0 6041.06 165.689 -2
2 1 0 6041.06 165.689 1
-3 -1 0 609.653 12.1975 1
-3 -1 0 584.721 11.5372 2
-3 -1 0 1199.66 73.9763 -2
-3 -1 0 1199.66 73.9763 1
3 1 0 579.015 12.1497 1
3 1 0 548.695 11.4919 2
-4 -1 0 305.788 6.92792 1
-4 -1 0 297.476 7.22881 2
4 1 0 267.431 6.71772 1
4 1 0 248.916 6.47008 2
-5 -1 0 291.703 7.38231 2
-5 -1 0 298.282 7.45072 1
5 1 0 270.099 6.49747 2
5 1 0 282.470 7.38322 1
-6 -1 0 117.148 4.37647 2
-6 -1 0 116.466 4.77265 1
6 1 0 103.973 4.04713 2
6 1 0 114.802 4.55915 1
-7 -1 0 106.102 6.95029 1
-7 -1 0 90.1439 6.56481 2
7 1 0 87.6401 5.39001 2
7 1 0 101.992 5.46054 1
-8 -1 0 496.430 16.2674 2
-8 -1 0 520.814 17.9257 1
8 1 0 545.799 17.9499 1
8 1 0 518.563 14.9120 2
-9 -1 0 291.448 12.6911 2
-9 -1 0 300.499 13.6277 1
9 1 0 306.235 15.1359 1
9 1 0 269.936 12.7610 2
0 -2 0 1079.74 26.1663 1
0 -2 0 1032.27 24.8154 2
0 2 0 1213.35 26.1993 1
0 2 0 1147.02 24.8936 2
-1 -2 0 1414.15 24.0487 1
-1 -2 0 1345.44 22.3011 2
1 2 0 1514.67 24.2078 1
1 2 0 1459.50 23.1418 2
-2 -2 0 456.027 8.83563 1
-2 -2 0 431.492 8.37447 2
2 2 0 492.718 8.57564 1
2 2 0 472.052 8.19741 2
-3 -2 0 336.269 7.29169 1
-3 -2 0 303.063 6.45977 2
3 2 0 350.282 7.77405 1
3 2 0 325.196 7.22617 2
-4 -2 0 178.990 5.14015 1
-4 -2 0 168.101 4.72693 2
4 2 0 209.547 9.56244 2
4 2 0 254.951 5.77646 1
-5 -2 0 375.618 8.86497 1
-5 -2 0 354.609 7.85706 2
5 2 0 323.944 7.68540 2
5 2 0 363.654 8.42568 1
-6 -2 0 654.252 14.8269 2
-6 -2 0 687.288 16.2333 1
6 2 0 667.966 14.5786 1
6 2 0 646.447 14.2896 2
-7 -2 0 505.992 14.2633 1
-7 -2 0 471.727 13.6799 2
7 2 0 477.701 13.8968 1
7 2 0 445.967 11.8614 2
-8 -2 0 8.73274 5.51398 1
-8 -2 0 12.9486 5.73088 2
8 2 0 7.03564 3.52691 2
8 2 0 3.41959 4.21795 1
-9 -2 0 57.6335 8.98724 2
-9 -2 0 76.4539 12.8192 1
9 2 0 58.9472 6.45727 2
9 2 0 73.1516 8.61582 1
0 -3 0 1.45329 1.12325 2
0 -3 0 1.73832 0.92114 1
0 3 0 1.94359 0.93406 1
0 3 0 0.21280 1.00526 2
-1 -3 0 180.003 4.32647 1
-1 -3 0 170.584 4.40707 2
1 3 0 212.019 5.22922 2
1 3 0 216.583 5.39913 1
-2 -3 0 986.095 18.2979 1
-2 -3 0 956.019 15.9849 2
2 3 0 876.866 14.9340 2
2 3 0 947.813 16.6242 1
-3 -3 0 568.174 12.1252 2
-3 -3 0 596.760 11.5753 1
3 3 0 603.270 11.2283 2
3 3 0 638.775 11.3427 1
-4 -3 0 245.280 5.65790 2
-4 -3 0 257.743 6.66886 1
4 3 0 263.479 6.15007 1
4 3 0 252.531 5.91041 2
-5 -3 0 286.090 7.30705 2
-5 -3 0 305.382 7.83517 1
5 3 0 295.318 7.81163 2
5 3 0 316.940 7.50675 1
-6 -3 0 6.37645 3.47403 2
-6 -3 0 5.65279 3.52100 1
6 3 0 11.4207 2.84205 2
6 3 0 26.8696 3.94760 1
-7 -3 0 311.355 10.6748 2
-7 -3 0 321.154 11.1728 1
7 3 0 331.366 10.3628 2
7 3 0 375.153 11.6624 1
-8 -3 0 334.063 12.1015 1
-8 -3 0 343.369 14.5379 2
8 3 0 331.177 11.5736 1
8 3 0 319.398 15.3804 2
0 -4 0 1724.93 39.0681 2
0 -4 0 1744.48 43.7533 1
0 4 0 1651.94 50.1469 2
0 4 0 1741.39 76.2868 1
-1 -4 0 488.228 9.49937 1
-1 -4 0 459.110 8.78942 2
1 4 0 390.128 11.6880 2
1 4 0 411.303 10.6890 1
-2 -4 0 2.46760 1.76768 2
-2 -4 0 3.70678 1.89658 1
2 4 0 10.1363 2.27392 1
2 4 0 9.37187 2.15293 2
-3 -4 0 473.253 9.05913 2
-3 -4 0 507.966 10.3530 1
3 4 0 478.395 9.72362 1
3 4 0 440.021 10.7615 2
-4 -4 0 142.110 4.44859 2
-4 -4 0 138.443 5.14584 1
4 4 0 197.068 5.22893 1
4 4 0 185.911 4.34418 2
-5 -4 0 381.670 11.0929 2
-5 -4 0 390.110 11.9813 1
5 4 0 491.143 11.3647 2
5 4 0 532.623 11.8073 1
-6 -4 0 473.667 12.7259 1
-6 -4 0 457.996 15.3705 2
6 4 0 431.241 12.7260 1
6 4 0 395.898 10.4691 2
-7 -4 0 141.187 8.74084 2
-7 -4 0 152.691 7.56718 1
7 4 0 149.068 7.90698 1
7 4 0 132.995 8.44717 2
-8 -4 0 1.22545 7.48382 2
-8 -4 0 8.02596 6.29016 1
8 4 0 8.14900 7.75203 2
8 4 0 5.20250 7.57347 1
0 -5 0 0.06625 1.38246 2
0 -5 0 5.35011 7.06049 1
0 5 0 -2.9526 4.76780 2
0 5 0 -1.2947 5.45107 1
-1 -5 0 827.354 17.1121 2
-1 -5 0 878.587 20.3285 1
1 5 0 845.287 24.1899 1
1 5 0 766.411 19.0360 2
-2 -5 0 980.735 22.5679 1
-2 -5 0 929.919 21.7305 2
2 5 0 825.071 22.3996 2
2 5 0 869.477 20.4538 1
-3 -5 0 1.54246 5.05581 1
-3 -5 0 2.38833 3.22876 2
3 5 0 23.9483 4.51558 2
3 5 0 30.7820 4.20148 1
-4 -5 0 370.198 8.81395 2
-4 -5 0 382.977 10.2662 1
4 5 0 494.843 12.7886 1
4 5 0 467.785 21.0812 2
-5 -5 0 136.734 5.23170 1
-5 -5 0 135.773 4.84868 2
5 5 0 119.518 4.60190 2
5 5 0 122.226 4.97033 1
-6 -5 0 3.34400 4.30775 1
-6 -5 0 3.63580 4.08375 2
6 5 0 4.25722 3.49228 1
6 5 0 6.13757 4.14343 2
-7 -5 0 184.170 9.69576 2
-7 -5 0 179.437 17.9905 1
7 5 0 143.973 9.95867 2
7 5 0 162.737 9.75200 1
0 -6 0 960.415 33.6573 1
0 -6 0 915.746 32.6072 2
0 6 0 892.422 48.9377 1
0 6 0 857.877 44.5351 2
-1 -6 0 493.151 11.3983 1
-1 -6 0 465.357 12.1847 2
1 6 0 461.013 16.3847 2
1 6 0 503.969 19.1411 1
-2 -6 0 23.5294 3.46695 2
-2 -6 0 29.3784 5.23342 1
2 6 0 55.6566 4.47275 2
2 6 0 58.3030 5.53583 1
-3 -6 0 14.6834 3.49745 2
-3 -6 0 18.8286 4.22328 1
3 6 0 11.7422 4.14097 2
3 6 0 13.9191 5.08983 1
-4 -6 0 115.767 5.89404 1
-4 -6 0 104.901 5.12779 2
4 6 0 128.203 9.93601 2
4 6 0 135.880 8.75981 1
-5 -6 0 170.735 7.91638 1
-5 -6 0 182.024 7.31862 2
5 6 0 142.434 11.7445 1
5 6 0 128.917 14.0485 2
-6 -6 0 107.912 7.55110 1
-6 -6 0 92.3096 9.39043 2
6 6 0 126.508 17.3887 2
6 6 0 129.152 18.0538 1
0 -7 0 3.23575 7.76363 2
0 -7 0 -6.8511 3.92383 1
0 7 0 -5.3846 15.1833 1
0 7 0 0.45941 17.2064 2
-1 -7 0 149.424 4.62061 2
-1 -7 0 158.602 8.96578 1
1 7 0 140.251 14.6055 1
1 7 0 123.572 25.3179 2
-2 -7 0 362.240 11.2468 1
-2 -7 0 344.203 11.7323 2
2 7 0 413.294 19.3828 1
2 7 0 384.458 22.3410 2
-3 -7 0 202.865 10.1496 1
-3 -7 0 203.764 7.19012 2
3 7 0 200.870 13.1123 2
3 7 0 229.811 21.1275 1
-4 -7 0 83.3094 8.19519 1
-4 -7 0 73.3425 5.83223 2
4 7 0 46.7738 15.1837 2
4 7 0 69.4674 15.4233 1
-9 0 1 110.538 8.62979 2
-9 0 1 126.928 9.01439 1
-8 0 1 3.86677 5.31846 2
-8 0 1 9.53676 4.77364 1
-7 0 1 18.2747 4.68945 1
-7 0 1 17.7250 4.05849 2
-6 0 1 948.347 21.2743 2
-6 0 1 979.358 18.9992 1
-5 0 1 1190.00 21.6875 2
-5 0 1 1231.17 22.6377 1
-4 0 1 1028.22 18.7781 1
-4 0 1 992.987 17.9887 2
-3 0 1 23.6505 1.70936 1
-3 0 1 20.2965 1.47721 2
-2 0 1 4351.61 174.802 -2
-2 0 1 4351.61 174.802 1
-2 0 1 2213.29 41.0260 1
-2 0 1 2156.54 39.9025 2
-1 0 1 467.966 10.0562 2
-1 0 1 467.130 12.6915 1
-1 0 1 910.707 22.0838 -2
-1 0 1 910.707 22.0838 1
1 0 1 18.3169 0.97861 1
1 0 1 19.5301 1.01227 2
1 0 1 34.0092 2.58966 -2
1 0 1 34.0092 2.58966 1
2 0 1 5905.31 236.677 -2
2 0 1 5905.31 236.677 1
2 0 1 2814.96 61.6216 2
2 0 1 3193.87 69.4386 1
3 0 1 119.202 3.84331 1
3 0 1 110.674 3.90943 2
4 0 1 119.357 4.26847 2
4 0 1 127.540 4.36531 1
5 0 1 874.930 16.9131 1
5 0 1 832.351 16.5076 2
6 0 1 860.687 16.8895 2
6 0 1 890.116 18.3526 1
7 0 1 282.644 9.71974 2
7 0 1 303.619 10.1762 1
8 0 1 9.05122 5.46574 1
8 0 1 6.93819 5.68589 2
9 0 1 32.5047 7.20824 2
9 0 1 25.9954 6.79624 1
9 -1 -1 222.225 11.0218 2
9 -1 -1 209.063 10.9887 1
-9 1 1 241.706 11.6112 1
-9 1 1 213.266 12.1846 2
8 -1 -1 356.789 13.3674 2
8 -1 -1 360.733 13.1393 1
-8 1 1 395.956 12.6046 1
-8 1 1 362.509 10.9993 2
7 -1 -1 164.327 8.01154 2
7 -1 -1 171.501 8.31903 1
-7 1 1 128.006 6.31381 2
-7 1 1 135.996 6.57405 1
6 -1 -1 651.326 13.9718 2
6 -1 -1 686.859 15.4515 1
-6 1 1 789.632 15.0395 1
-6 1 1 747.791 14.7926 2
5 -1 -1 88.1173 3.72004 1
5 -1 -1 80.2575 3.48195 2
-5 1 1 79.2196 3.79086 1
-5 1 1 78.5809 3.04729 2
4 -1 -1 1510.43 32.6999 2
4 -1 -1 1583.17 32.4162 1
-4 1 1 1820.13 31.3506 1
-4 1 1 1749.14 31.4049 2
3 -1 -1 3965.02 65.7890 2
3 -1 -1 4074.32 66.5709 1
-3 1 1 3602.36 66.2711 2
-3 1 1 3804.97 77.1939 1
2 -1 -1 2538.26 43.1549 2
2 -1 -1 2654.87 42.1377 1
-2 1 1 2169.50 45.6234 2
-2 1 1 2267.28 51.5437 1
-2 1 1 4233.44 172.978 -2
-2 1 1 4233.44 172.978 1
1 -1 -1 77.1528 1.65303 1
1 -1 -1 71.7115 1.57974 2
-1 1 1 392.054 17.2540 -2
-1 1 1 392.054 17.2540 1
0 -1 -1 194.475 3.56733 2
0 -1 -1 208.455 3.85385 1
0 -1 -1 401.096 26.4590 -2
0 -1 -1 401.096 26.4590 1
0 1 1 449.787 15.6065 -2
0 1 1 449.787 15.6065 1
0 1 1 225.212 5.12004 2
0 1 1 235.991 5.33703 1
-1 -1 -1 718.408 13.6521 1
-1 -1 -1 686.428 14.4732 2
-1 -1 -1 1445.71 88.5346 -2
-1 -1 -1 1445.71 88.5346 1
1 1 1 802.622 14.4411 1
1 1 1 771.438 13.3389 2
1 1 1 1589.65 66.7692 -2
1 1 1 1589.65 66.7692 1
-2 -1 -1 720.252 15.1513 2
-2 -1 -1 756.094 16.5653 1
2 1 1 1085.45 26.9426 -2
2 1 1 1085.45 26.9426 1
2 1 1 581.795 40.4372 2
2 1 1 585.617 29.5944 1
-3 -1 -1 1978.71 41.2994 1
-3 -1 -1 1905.13 39.9616 2
-3 -1 -1 4004.69 135.986 -2
-3 -1 -1 4004.69 135.986 1
3 1 1 1965.17 46.6977 2
3 1 1 1999.46 48.3787 1
3 1 1 4067.66 117.212 -2
3 1 1 4067.66 117.212 1
-4 -1 -1 1030.15 19.7820 1
-4 -1 -1 991.625 20.0649 2
4 1 1 1055.16 19.8691 1
4 1 1 1038.39 19.3289 2
-5 -1 -1 688.005 13.6916 2
-5 -1 -1 730.800 14.4492 1
5 1 1 656.877 14.2162 1
5 1 1 629.963 13.5126 2
-6 -1 -1 53.5746 3.70656 2
-6 -1 -1 57.6632 3.89951 1
6 1 1 69.2599 3.95334 1
6 1 1 63.9164 3.48522 2
-7 -1 -1 279.405 10.6204 2
-7 -1 -1 298.073 11.2956 1
7 1 1 289.655 9.56586 2
7 1 1 324.024 10.0905 1
-8 -1 -1 150.044 8.84301 2
-8 -1 -1 161.834 9.06271 1
8 1 1 188.816 8.88836 2
8 1 1 199.636 9.24353 1
-9 -1 -1 78.9019 8.34109 2
-9 -1 -1 86.7529 8.95785 1
9 1 1 60.9547 9.57579 1
9 1 1 44.5019 7.69404 2
9 -2 -1 86.1123 9.85825 2
9 -2 -1 96.1484 9.78489 1
-9 2 1 109.211 8.44901 1
-9 2 1 88.1547 6.93974 2
8 -2 -1 18.3355 5.80355 2
8 -2 -1 23.5259 5.77023 1
-8 2 1 14.6693 3.65201 2
-8 2 1 11.9875 4.30274 1
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;
_shelx_hkl_checksum 76395
_shelx_res_file
;
TITL m22123 : space group P21
m22123.res
created by SHELXL-2019/2 at 09:33:53 on 01-Sep-2022
CELL 0.71073 7.5162 6.1125 15.7249 90.000 98.625 90.000
ZERR 2 0.0003 0.0002 0.0005 0.000 0.001 0.000
LATT -1
SYMM -X, 1/2+Y, -Z
SFAC C H BR N O
UNIT 34 34 2 4 2
TEMP -183
SIZE 0.35 0.20 0.06
REM FORM slab cut from lath
REM COLR colourless
MERG 0
L.S. 10
ACTA
BOND $H
LIST 6
CONF
HTAB
REM Various planes for dihedrals etc.
MPLA C5 C6 C7 C8 C9 C10
MPLA 6 C12 C13 C14 C15 C16 C17 Br1
REM Torsion angle:
RTAB tors N1 C11 C12 C13
EQIV $2 x, y-1, z
HTAB C13 O1_$2
HTAB C14 O1_$2
HTAB
FMAP 2
PLAN 20
REM EXTI 0.000000 not needed.
WGHT 0.015800 0.099900
BASF 0.48604
FVAR 1.08994
BR1 3 0.090547 0.112863 0.950387 11.00000 0.01541 0.01942 =
0.02254 0.00283 0.00626 -0.00119
O1 5 0.672997 0.884387 0.839924 11.00000 0.02691 0.01401 =
0.03359 -0.00649 0.01451 -0.00233
N1 4 0.776314 0.602248 0.768958 11.00000 0.01588 0.01242 =
0.01359 -0.00073 0.00422 -0.00256
N2 4 0.802222 0.577290 0.589085 11.00000 0.01624 0.01020 =
0.01232 -0.00133 0.00315 -0.00175
C1 1 0.754435 0.391296 0.724081 11.00000 0.02580 0.01187 =
0.01492 -0.00079 0.00810 -0.00019
AFIX 23
H1A 2 0.666366 0.300535 0.749181 11.00000 -1.20000
H1B 2 0.870892 0.312654 0.731847 11.00000 -1.20000
AFIX 0
C2 1 0.689615 0.424764 0.628811 11.00000 0.02550 0.01194 =
0.01404 -0.00229 0.00500 -0.00602
AFIX 23
H2A 2 0.688355 0.281887 0.599077 11.00000 -1.20000
H2B 2 0.564666 0.480861 0.621072 11.00000 -1.20000
AFIX 0
C3 1 0.833135 0.784337 0.636072 11.00000 0.01612 0.01295 =
0.01592 0.00008 0.00164 -0.00204
AFIX 23
H3A 2 0.719803 0.869390 0.629414 11.00000 -1.20000
H3B 2 0.923829 0.871335 0.611219 11.00000 -1.20000
AFIX 0
C4 1 0.898516 0.745879 0.731184 11.00000 0.01413 0.01786 =
0.01463 0.00010 0.00441 -0.00366
AFIX 23
H4A 2 1.019905 0.679267 0.738344 11.00000 -1.20000
H4B 2 0.907757 0.887866 0.761819 11.00000 -1.20000
AFIX 0
C5 1 0.768761 0.591846 0.498299 11.00000 0.01010 0.01784 =
0.01362 0.00415 0.00102 0.00180
C6 1 0.819961 0.775338 0.454824 11.00000 0.01940 0.01905 =
0.01786 0.00197 0.00298 -0.00204
AFIX 43
H6 2 0.874536 0.895931 0.486795 11.00000 -1.20000
AFIX 0
C7 1 0.792229 0.784015 0.365533 11.00000 0.02177 0.02226 =
0.02020 0.00745 0.00658 -0.00083
AFIX 43
H7 2 0.828030 0.910876 0.337573 11.00000 -1.20000
AFIX 0
C8 1 0.713443 0.611584 0.316311 11.00000 0.01670 0.03074 =
0.01339 0.00192 0.00134 0.00420
AFIX 43
H8 2 0.694672 0.618576 0.255269 11.00000 -1.20000
AFIX 0
C9 1 0.663335 0.430068 0.358716 11.00000 0.02574 0.02723 =
0.01666 -0.00379 0.00101 -0.00651
AFIX 43
H9 2 0.610006 0.309579 0.326239 11.00000 -1.20000
AFIX 0
C10 1 0.688921 0.419035 0.447796 11.00000 0.02639 0.02161 =
0.01662 0.00124 0.00087 -0.00737
AFIX 43
H10 2 0.651625 0.291940 0.475097 11.00000 -1.20000
AFIX 0
C11 1 0.666807 0.689445 0.821222 11.00000 0.01464 0.01550 =
0.01297 0.00071 0.00009 0.00202
C12 1 0.533820 0.544361 0.856048 11.00000 0.01539 0.01511 =
0.00971 -0.00186 0.00068 -0.00014
C13 1 0.576997 0.339467 0.892050 11.00000 0.01267 0.01433 =
0.01146 -0.00188 0.00174 0.00263
AFIX 43
H13 2 0.696220 0.285267 0.894978 11.00000 -1.20000
AFIX 0
C14 1 0.447636 0.213170 0.923785 11.00000 0.01730 0.01317 =
0.00954 -0.00140 0.00101 0.00114
AFIX 43
H14 2 0.477362 0.073859 0.948719 11.00000 -1.20000
AFIX 0
C15 1 0.274769 0.295155 0.918185 11.00000 0.01350 0.01744 =
0.01100 -0.00151 0.00346 -0.00324
C16 1 0.229031 0.501415 0.886678 11.00000 0.01223 0.01856 =
0.01378 0.00074 0.00291 0.00287
AFIX 43
H16 2 0.110701 0.556801 0.885896 11.00000 -1.20000
AFIX 0
C17 1 0.361040 0.626664 0.855978 11.00000 0.01936 0.01448 =
0.01169 0.00136 0.00115 0.00305
AFIX 43
H17 2 0.332668 0.769940 0.834754 11.00000 -1.20000
AFIX 0
HKLF 5
REM m22123 : space group P21
REM wR2 = 0.0491, GooF = S = 1.044, Restrained GooF = 1.044 for all data
REM R1 = 0.0225 for 6410 Fo > 4sig(Fo) and 0.0266 for all 6918 data
REM 191 parameters refined using 1 restraints
END
WGHT 0.0158 0.0999
REM No hydrogen bonds found for HTAB generation
REM Highest difference peak 0.293, deepest hole -0.222, 1-sigma level 0.049
Q1 1 0.1390 -0.0269 0.9380 11.00000 0.05 0.29
Q2 1 0.6041 0.6124 0.8388 11.00000 0.05 0.27
Q3 1 0.7235 0.5098 0.3416 11.00000 0.05 0.22
Q4 1 0.7084 0.7148 0.3439 11.00000 0.05 0.21
Q5 1 0.5638 0.4513 0.8830 11.00000 0.05 0.21
Q6 1 0.7394 0.5081 0.4758 11.00000 0.05 0.20
Q7 1 0.7635 0.7897 0.4173 11.00000 0.05 0.20
Q8 1 0.0375 0.1153 0.8972 11.00000 0.05 0.20
Q9 1 0.2788 0.7591 0.8041 11.00000 0.05 0.19
Q10 1 0.8638 0.7550 0.6790 11.00000 0.05 0.19
Q11 1 0.7749 0.5968 0.5408 11.00000 0.05 0.19
Q12 1 0.7313 0.4062 0.4067 11.00000 0.05 0.19
Q13 1 0.7540 0.6969 0.4749 11.00000 0.05 0.18
Q14 1 0.7367 0.5120 0.6124 11.00000 0.05 0.18
Q15 1 0.0452 0.2555 0.9646 11.00000 0.05 0.18
Q16 1 0.8541 0.7536 0.4170 11.00000 0.05 0.18
Q17 1 0.7438 0.6306 0.8084 11.00000 0.05 0.17
Q18 1 0.4961 0.2518 0.8857 11.00000 0.05 0.17
Q19 1 0.8468 0.5968 0.7734 11.00000 0.05 0.17
Q20 1 0.6220 0.2926 0.8769 11.00000 0.05 0.17
;
_shelx_res_checksum 39843
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.09055(3) 0.11286(6) 0.95039(2) 0.01878(8) Uani d 1 . .
O O1 0.6730(3) 0.8844(4) 0.83992(15) 0.0238(5) Uani d 1 . .
N N1 0.7763(3) 0.6022(7) 0.76896(13) 0.0138(4) Uani d 1 . .
N N2 0.8022(3) 0.5773(4) 0.58908(14) 0.0128(6) Uani d 1 . .
C C1 0.7544(4) 0.3913(5) 0.72408(19) 0.0170(6) Uani d 1 . .
H H1A 0.666366 0.300535 0.749181 0.020 Uiso calc 1 . .
H H1B 0.870892 0.312654 0.731847 0.020 Uiso calc 1 . .
C C2 0.6896(4) 0.4248(5) 0.62881(19) 0.0170(6) Uani d 1 . .
H H2A 0.688355 0.281887 0.599077 0.020 Uiso calc 1 . .
H H2B 0.564666 0.480861 0.621072 0.020 Uiso calc 1 . .
C C3 0.8331(4) 0.7843(5) 0.63607(18) 0.0151(6) Uani d 1 . .
H H3A 0.719803 0.869390 0.629414 0.018 Uiso calc 1 . .
H H3B 0.923829 0.871335 0.611219 0.018 Uiso calc 1 . .
C C4 0.8985(4) 0.7459(5) 0.73118(19) 0.0153(6) Uani d 1 . .
H H4A 1.019905 0.679267 0.738344 0.018 Uiso calc 1 . .
H H4B 0.907757 0.887866 0.761819 0.018 Uiso calc 1 . .
C C5 0.7688(3) 0.5918(7) 0.49830(16) 0.0139(6) Uani d 1 . .
C C6 0.8200(4) 0.7753(5) 0.4548(2) 0.0187(6) Uani d 1 . .
H H6 0.874536 0.895931 0.486795 0.022 Uiso calc 1 . .
C C7 0.7922(5) 0.7840(5) 0.3655(2) 0.0211(7) Uani d 1 . .
H H7 0.828030 0.910876 0.337573 0.025 Uiso calc 1 . .
C C8 0.7134(3) 0.6116(10) 0.31631(16) 0.0204(5) Uani d 1 . .
H H8 0.694672 0.618576 0.255269 0.024 Uiso calc 1 . .
C C9 0.6633(5) 0.4301(6) 0.3587(2) 0.0234(7) Uani d 1 . .
H H9 0.610006 0.309579 0.326239 0.028 Uiso calc 1 . .
C C10 0.6889(5) 0.4190(5) 0.4478(2) 0.0218(7) Uani d 1 . .
H H10 0.651625 0.291940 0.475097 0.026 Uiso calc 1 . .
C C11 0.6668(4) 0.6894(5) 0.82122(18) 0.0146(6) Uani d 1 . .
C C12 0.5338(4) 0.5444(4) 0.85605(17) 0.0135(6) Uani d 1 . .
C C13 0.5770(4) 0.3395(5) 0.89205(18) 0.0128(6) Uani d 1 . .
H H13 0.696220 0.285267 0.894978 0.015 Uiso calc 1 . .
C C14 0.4476(4) 0.2132(5) 0.92378(17) 0.0134(6) Uani d 1 . .
H H14 0.477362 0.073859 0.948719 0.016 Uiso calc 1 . .
C C15 0.2748(4) 0.2952(5) 0.91818(18) 0.0138(6) Uani d 1 . .
C C16 0.2290(4) 0.5014(5) 0.88668(18) 0.0148(6) Uani d 1 . .
H H16 0.110701 0.556801 0.885896 0.018 Uiso calc 1 . .
C C17 0.3610(3) 0.6267(8) 0.85598(15) 0.0153(5) Uani d 1 . .
H H17 0.332668 0.769940 0.834754 0.018 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
Br1 0.01541(13) 0.01942(13) 0.02254(13) -0.0012(2) 0.00626(9) 0.00283(19)
O1 0.0269(12) 0.0140(11) 0.0336(13) -0.0023(9) 0.0145(11) -0.0065(9)
N1 0.0159(10) 0.0124(10) 0.0136(9) -0.0026(16) 0.0042(8) -0.0007(16)
N2 0.0162(11) 0.0102(17) 0.0123(10) -0.0017(9) 0.0032(8) -0.0013(10)
C1 0.0258(17) 0.0119(14) 0.0149(15) -0.0002(12) 0.0081(13) -0.0008(12)
C2 0.0255(17) 0.0119(14) 0.0140(15) -0.0060(12) 0.0050(12) -0.0023(11)
C3 0.0161(16) 0.0129(14) 0.0159(15) -0.0020(11) 0.0016(12) 0.0001(12)
C4 0.0141(15) 0.0179(15) 0.0146(14) -0.0037(11) 0.0044(12) 0.0001(11)
C5 0.0101(11) 0.0178(17) 0.0136(11) 0.0018(15) 0.0010(9) 0.0042(15)
C6 0.0194(17) 0.0190(16) 0.0179(16) -0.0020(13) 0.0030(13) 0.0020(12)
C7 0.0218(18) 0.0223(17) 0.0202(16) -0.0008(13) 0.0066(13) 0.0074(13)
C8 0.0167(12) 0.0307(14) 0.0134(11) 0.004(2) 0.0013(9) 0.002(2)
C9 0.0257(19) 0.0272(18) 0.0167(16) -0.0065(14) 0.0010(13) -0.0038(13)
C10 0.0264(19) 0.0216(17) 0.0166(16) -0.0074(13) 0.0009(13) 0.0012(13)
C11 0.0146(14) 0.0155(13) 0.0130(13) 0.0020(10) 0.0001(11) 0.0007(10)
C12 0.0154(14) 0.0151(15) 0.0097(13) -0.0001(10) 0.0007(11) -0.0019(9)
C13 0.0127(14) 0.0143(14) 0.0115(13) 0.0026(11) 0.0017(11) -0.0019(11)
C14 0.0173(15) 0.0132(14) 0.0095(13) 0.0011(11) 0.0010(11) -0.0014(11)
C15 0.0135(14) 0.0174(15) 0.0110(14) -0.0032(11) 0.0035(11) -0.0015(11)
C16 0.0122(14) 0.0186(15) 0.0138(14) 0.0029(11) 0.0029(11) 0.0007(12)
C17 0.0194(12) 0.0145(14) 0.0117(11) 0.0030(19) 0.0012(9) 0.0014(16)
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'
Br Br -0.2901 2.4595 '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'
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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 N1 C4 . . 119.1(3) ?
C11 N1 C1 . . 127.0(3) ?
C4 N1 C1 . . 111.4(2) ?
C5 N2 C2 . . 116.4(2) ?
C5 N2 C3 . . 116.4(3) ?
C2 N2 C3 . . 113.2(2) ?
N1 C1 C2 . . 110.6(2) ?
N1 C1 H1A . . 109.5 ?
C2 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 108.1 ?
N2 C2 C1 . . 112.8(2) ?
N2 C2 H2A . . 109.0 ?
C1 C2 H2A . . 109.0 ?
N2 C2 H2B . . 109.0 ?
C1 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
N2 C3 C4 . . 111.4(2) ?
N2 C3 H3A . . 109.3 ?
C4 C3 H3A . . 109.3 ?
N2 C3 H3B . . 109.3 ?
C4 C3 H3B . . 109.3 ?
H3A C3 H3B . . 108.0 ?
N1 C4 C3 . . 111.3(2) ?
N1 C4 H4A . . 109.4 ?
C3 C4 H4A . . 109.4 ?
N1 C4 H4B . . 109.4 ?
C3 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
C6 C5 C10 . . 117.0(2) ?
C6 C5 N2 . . 121.6(3) ?
C10 C5 N2 . . 121.4(3) ?
C7 C6 C5 . . 121.0(3) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C8 C7 C6 . . 121.5(3) ?
C8 C7 H7 . . 119.3 ?
C6 C7 H7 . . 119.3 ?
C9 C8 C7 . . 117.9(2) ?
C9 C8 H8 . . 121.1 ?
C7 C8 H8 . . 121.1 ?
C8 C9 C10 . . 121.5(3) ?
C8 C9 H9 . . 119.3 ?
C10 C9 H9 . . 119.3 ?
C9 C10 C5 . . 121.2(3) ?
C9 C10 H10 . . 119.4 ?
C5 C10 H10 . . 119.4 ?
O1 C11 N1 . . 121.5(3) ?
O1 C11 C12 . . 119.4(3) ?
N1 C11 C12 . . 119.1(3) ?
C17 C12 C13 . . 119.1(3) ?
C17 C12 C11 . . 117.3(3) ?
C13 C12 C11 . . 123.6(3) ?
C14 C13 C12 . . 120.8(3) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C15 C14 C13 . . 118.5(3) ?
C15 C14 H14 . . 120.8 ?
C13 C14 H14 . . 120.8 ?
C16 C15 C14 . . 122.4(3) ?
C16 C15 Br1 . . 118.6(2) ?
C14 C15 Br1 . . 119.0(2) ?
C15 C16 C17 . . 118.3(3) ?
C15 C16 H16 . . 120.9 ?
C17 C16 H16 . . 120.9 ?
C12 C17 C16 . . 120.9(4) ?
C12 C17 H17 . . 119.6 ?
C16 C17 H17 . . 119.6 ?
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
Br1 C15 . 1.904(3) ?
O1 C11 . 1.227(4) ?
N1 C11 . 1.356(4) ?
N1 C4 . 1.460(4) ?
N1 C1 . 1.467(4) ?
N2 C5 . 1.415(3) ?
N2 C2 . 1.461(4) ?
N2 C3 . 1.466(4) ?
C1 C2 . 1.518(4) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.521(4) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.397(5) ?
C5 C10 . 1.401(5) ?
C6 C7 . 1.389(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.387(6) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.376(6) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.387(4) ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C11 C12 . 1.500(4) ?
C12 C17 . 1.393(4) ?
C12 C13 . 1.393(4) ?
C13 C14 . 1.391(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.383(4) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.379(4) ?
C16 C17 . 1.395(5) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
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
_geom_hbond_publ_flag
C13 H13 O1 1_545 0.95 2.60 3.018(4) 107.3 no
C14 H14 O1 1_545 0.95 2.68 3.052(4) 104.0 no
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 C1 C2 . . . . 105.4(3) ?
C4 N1 C1 C2 . . . . -56.4(3) ?
C5 N2 C2 C1 . . . . 170.4(3) ?
C3 N2 C2 C1 . . . . -50.7(3) ?
N1 C1 C2 N2 . . . . 52.8(3) ?
C5 N2 C3 C4 . . . . -170.3(2) ?
C2 N2 C3 C4 . . . . 50.8(3) ?
C11 N1 C4 C3 . . . . -105.9(3) ?
C1 N1 C4 C3 . . . . 57.5(3) ?
N2 C3 C4 N1 . . . . -54.1(3) ?
C2 N2 C5 C6 . . . . 158.2(3) ?
C3 N2 C5 C6 . . . . 20.7(4) ?
C2 N2 C5 C10 . . . . -24.3(4) ?
C3 N2 C5 C10 . . . . -161.8(3) ?
C10 C5 C6 C7 . . . . 0.0(5) ?
N2 C5 C6 C7 . . . . 177.6(3) ?
C5 C6 C7 C8 . . . . -0.2(5) ?
C6 C7 C8 C9 . . . . -0.1(5) ?
C7 C8 C9 C10 . . . . 0.5(5) ?
C8 C9 C10 C5 . . . . -0.7(5) ?
C6 C5 C10 C9 . . . . 0.4(5) ?
N2 C5 C10 C9 . . . . -177.2(3) ?
C4 N1 C11 O1 . . . . -2.8(4) ?
C1 N1 C11 O1 . . . . -163.3(3) ?
C4 N1 C11 C12 . . . . 176.5(2) ?
C1 N1 C11 C12 . . . . 16.0(4) ?
O1 C11 C12 C17 . . . . 42.2(4) ?
N1 C11 C12 C17 . . . . -137.1(3) ?
O1 C11 C12 C13 . . . . -134.3(3) ?
N1 C11 C12 C13 . . . . 46.4(4) ?
C17 C12 C13 C14 . . . . 3.2(4) ?
C11 C12 C13 C14 . . . . 179.6(3) ?
C12 C13 C14 C15 . . . . 0.5(4) ?
C13 C14 C15 C16 . . . . -3.6(4) ?
C13 C14 C15 Br1 . . . . 173.6(2) ?
C14 C15 C16 C17 . . . . 2.9(4) ?
Br1 C15 C16 C17 . . . . -174.3(2) ?
C13 C12 C17 C16 . . . . -3.8(4) ?
C11 C12 C17 C16 . . . . 179.5(3) ?
C15 C16 C17 C12 . . . . 0.9(4) ?
_cod_database_fobs_code 2244179