#------------------------------------------------------------------------------ #$Date: 2017-08-02 05:23:24 +0300 (Wed, 02 Aug 2017) $ #$Revision: 199448 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/88/7228823.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_7228823 loop_ _publ_author_name 'Bhat, Gulzar A.' 'Kalita, Alok Ch' 'Murugavel, Ramaswamy' _publ_section_title ; Intriguing Structural Chemistry of Neutral and Anionic Layered Monoalkylphosphates: Single-Source Precursors for High-Yield Ceramic Phosphates ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C7CE01066D _journal_year 2017 _chemical_formula_sum 'C8 H20 N O4 P' _chemical_formula_weight 225.22 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-03-06 deposited with the CCDC. 2017-08-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.199(4) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 22.8176(10) _cell_length_b 5.9912(3) _cell_length_c 18.3149(7) _cell_measurement_reflns_used 5071 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 30.6460 _cell_measurement_theta_min 2.6590 _cell_volume 2489.10(19) _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r3' _computing_data_collection 'CrystalClear-SM Expert 2.0 r3 (Rigaku, 2009)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Rigaku Saturn724' _diffrn_measurement_method \w _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_unetI/netI 0.0290 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 8941 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 25.000 _diffrn_reflns_theta_min 2.713 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.62804 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1998)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.202 _exptl_crystal_description needles _exptl_crystal_F_000 976 _exptl_crystal_size_max 0.170 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.040 _refine_diff_density_max 0.373 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 130 _refine_ls_number_reflns 2187 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0464 _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^)+(0.0534P)^2^+3.8950P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1150 _refine_ls_wR_factor_ref 0.1248 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1815 _reflns_number_total 2187 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce01066d2.cif _cod_data_source_block 2 _cod_original_cell_volume 2489.09(19) _cod_database_code 7228823 _shelx_shelxl_version_number 2014/7 _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 0.965 _shelx_estimated_absorpt_t_max 0.992 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL gb-200_a.res in C2/c CELL 0.71073 22.8176 5.9912 18.3149 90.000 96.199 90.000 ZERR 8.00 0.0010 0.0003 0.0007 0.000 0.004 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H N O P UNIT 64 160 8 32 8 MERG 2 OMIT -3.00 50.00 OMIT 2 0 0 OMIT 5 0 0 OMIT 0 0 2 MORE -1 EQIV $1 x, y-1, z HTAB N1 O4_$1 EQIV $2 -x+3/2, y-1/2, -z+3/2 HTAB N1 O2_$2 HTAB N1 O2 EQIV $3 -x+3/2, -y+3/2, -z+1 HTAB O3 O4_$3 FMAP 2 PLAN 20 SIZE 0.040 0.100 0.170 ACTA 52.00 HTAB 2.00000 BOND $H CONF LIST 6 L.S. 10 TEMP -123.00 WGHT 0.053400 3.895000 FVAR 0.27016 C1 1 0.900635 1.141530 0.640384 11.00000 0.05442 0.05301 = 0.07348 0.00101 0.00537 -0.01763 AFIX 137 H1D 2 0.913128 1.262701 0.609621 11.00000 -1.50000 H1E 2 0.934470 1.045616 0.656006 11.00000 -1.50000 H1F 2 0.885039 1.204644 0.683715 11.00000 -1.50000 AFIX 0 C2 1 0.853775 1.006777 0.597400 11.00000 0.04464 0.04196 = 0.05054 0.01402 0.00427 -0.00591 AFIX 23 H2A 2 0.820188 1.104042 0.579502 11.00000 -1.20000 H2B 2 0.869586 0.938712 0.554331 11.00000 -1.20000 AFIX 0 C3 1 0.637816 0.223677 0.666943 11.00000 0.03428 0.03835 = 0.02782 -0.00337 0.00104 0.00179 AFIX 13 H3A 2 0.629986 0.341357 0.703376 11.00000 -1.20000 AFIX 0 C4 1 0.599218 0.028130 0.677893 11.00000 0.05031 0.06955 = 0.12252 0.04444 -0.01144 -0.01994 AFIX 23 H4A 2 0.606517 -0.024029 0.729363 11.00000 -1.20000 H4B 2 0.608830 -0.095596 0.645392 11.00000 -1.20000 AFIX 0 C5 1 0.533664 0.092258 0.660487 11.00000 0.04402 0.10348 = 0.14700 0.04403 -0.00658 -0.02828 AFIX 23 H5A 2 0.508819 -0.041341 0.665205 11.00000 -1.20000 H5B 2 0.523102 0.204676 0.696461 11.00000 -1.20000 AFIX 0 C6 1 0.521562 0.185083 0.584593 11.00000 0.04067 0.10778 = 0.08124 -0.02766 -0.01736 0.00632 AFIX 23 H6A 2 0.479644 0.229923 0.575589 11.00000 -1.20000 H6B 2 0.528922 0.068644 0.548328 11.00000 -1.20000 AFIX 0 C7 1 0.560314 0.384261 0.574818 11.00000 0.04149 0.11097 = 0.06920 0.03264 -0.00142 0.01938 AFIX 23 H7A 2 0.550689 0.505214 0.608370 11.00000 -1.20000 H7B 2 0.552649 0.440098 0.523806 11.00000 -1.20000 AFIX 0 C8 1 0.626052 0.321806 0.591122 11.00000 0.03859 0.08137 = 0.04846 0.02509 0.00096 0.01264 AFIX 23 H8A 2 0.636770 0.212153 0.554367 11.00000 -1.20000 H8B 2 0.650661 0.456583 0.587432 11.00000 -1.20000 AFIX 0 N1 3 0.700964 0.155741 0.681292 11.00000 0.03706 0.02454 = 0.01853 -0.00064 -0.00162 0.00034 AFIX 137 H1A 2 0.708660 0.046002 0.649325 11.00000 -1.20000 H1B 2 0.708266 0.104268 0.728138 11.00000 -1.20000 H1C 2 0.724453 0.275548 0.675161 11.00000 -1.20000 AFIX 0 O1 4 0.834188 0.833619 0.644401 11.00000 0.04028 0.03172 = 0.02782 0.00631 -0.00412 -0.00391 O2 4 0.773745 0.516892 0.673522 11.00000 0.05079 0.02936 = 0.02141 0.00307 -0.00207 -0.00574 O3 4 0.804899 0.544448 0.546558 11.00000 0.06094 0.03708 = 0.02032 0.00095 -0.00097 0.02196 AFIX 147 H3 2 0.789969 0.599186 0.506590 11.00000 -1.50000 AFIX 0 O4 4 0.729091 0.815797 0.584272 11.00000 0.03653 0.03277 = 0.01873 -0.00112 0.00090 0.00579 P1 5 0.781677 0.674183 0.611918 11.00000 0.03775 0.02374 = 0.01605 0.00032 -0.00053 0.00225 HKLF 4 REM gb-200_a.res in C2/c REM R1 = 0.0464 for 1815 Fo > 4sig(Fo) and 0.0574 for all 2187 data REM 130 parameters refined using 0 restraints END WGHT 0.0534 3.8955 REM Instructions for potential hydrogen bonds HTAB N1 O4_$1 HTAB N1 O2_$2 HTAB N1 O2 HTAB O3 O4_$3 REM Highest difference peak 0.373, deepest hole -0.316, 1-sigma level 0.050 Q1 1 0.5966 -0.0257 0.6308 11.00000 0.05 0.37 Q2 1 0.5319 0.0243 0.6110 11.00000 0.05 0.29 Q3 1 0.5523 0.4317 0.6218 11.00000 0.05 0.28 Q4 1 0.6210 0.3952 0.6528 11.00000 0.05 0.28 Q5 1 0.6395 0.2022 0.6237 11.00000 0.05 0.22 Q6 1 0.6191 -0.1010 0.6028 11.00000 0.05 0.21 Q7 1 0.7867 0.5360 0.6590 11.00000 0.05 0.20 Q8 1 0.7406 0.7204 0.5893 11.00000 0.05 0.19 Q9 1 0.7871 0.4748 0.6827 11.00000 0.05 0.19 Q10 1 0.6030 -0.1130 0.6874 11.00000 0.05 0.19 Q11 1 0.5722 0.0669 0.6824 11.00000 0.05 0.18 Q12 1 0.6508 0.3683 0.5572 11.00000 0.05 0.18 Q13 1 0.5126 0.0684 0.6817 11.00000 0.05 0.18 Q14 1 0.7075 0.7854 0.5648 11.00000 0.05 0.18 Q15 1 0.7498 0.5772 0.6833 11.00000 0.05 0.17 Q16 1 0.7587 0.8610 0.5811 11.00000 0.05 0.16 Q17 1 0.8115 0.7885 0.6318 11.00000 0.05 0.15 Q18 1 0.9209 1.0507 0.6765 11.00000 0.05 0.15 Q19 1 0.7282 0.5390 0.6635 11.00000 0.05 0.14 Q20 1 0.5427 0.2364 0.5638 11.00000 0.05 0.14 ; _shelx_res_checksum 49294 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp C1 C 0.90064(13) 1.1415(5) 0.64038(18) 0.0604(8) Uani 1 1 d . . H1D H 0.9131 1.2627 0.6096 0.091 Uiso 1 1 calc R U H1E H 0.9345 1.0456 0.6560 0.091 Uiso 1 1 calc R U H1F H 0.8850 1.2046 0.6837 0.091 Uiso 1 1 calc R U C2 C 0.85377(12) 1.0068(5) 0.59740(15) 0.0458(7) Uani 1 1 d . . H2A H 0.8202 1.1040 0.5795 0.055 Uiso 1 1 calc R U H2B H 0.8696 0.9387 0.5543 0.055 Uiso 1 1 calc R U C3 C 0.63782(10) 0.2237(4) 0.66694(12) 0.0337(6) Uani 1 1 d . . H3A H 0.6300 0.3414 0.7034 0.040 Uiso 1 1 calc R U C4 C 0.59922(14) 0.0281(6) 0.6779(2) 0.0823(12) Uani 1 1 d . . H4A H 0.6065 -0.0240 0.7294 0.099 Uiso 1 1 calc R U H4B H 0.6088 -0.0956 0.6454 0.099 Uiso 1 1 calc R U C5 C 0.53366(15) 0.0923(8) 0.6605(3) 0.0994(15) Uani 1 1 d . . H5A H 0.5088 -0.0413 0.6652 0.119 Uiso 1 1 calc R U H5B H 0.5231 0.2047 0.6965 0.119 Uiso 1 1 calc R U C6 C 0.52156(14) 0.1851(7) 0.5846(2) 0.0783(12) Uani 1 1 d . . H6A H 0.4796 0.2299 0.5756 0.094 Uiso 1 1 calc R U H6B H 0.5289 0.0686 0.5483 0.094 Uiso 1 1 calc R U C7 C 0.56031(13) 0.3843(7) 0.57482(19) 0.0744(11) Uani 1 1 d . . H7A H 0.5507 0.5052 0.6084 0.089 Uiso 1 1 calc R U H7B H 0.5526 0.4401 0.5238 0.089 Uiso 1 1 calc R U C8 C 0.62605(12) 0.3218(6) 0.59112(16) 0.0564(8) Uani 1 1 d . . H8A H 0.6368 0.2122 0.5544 0.068 Uiso 1 1 calc R U H8B H 0.6507 0.4566 0.5874 0.068 Uiso 1 1 calc R U N1 N 0.70096(8) 0.1557(3) 0.68129(9) 0.0271(4) Uani 1 1 d . . H1A H 0.7087 0.0460 0.6493 0.032 Uiso 1 1 calc R U H1B H 0.7083 0.1043 0.7281 0.032 Uiso 1 1 calc R U H1C H 0.7245 0.2755 0.6752 0.032 Uiso 1 1 calc R U O1 O 0.83419(7) 0.8336(3) 0.64440(8) 0.0338(4) Uani 1 1 d . . O2 O 0.77375(7) 0.5169(3) 0.67352(8) 0.0343(4) Uani 1 1 d . . O3 O 0.80490(8) 0.5444(3) 0.54656(8) 0.0398(5) Uani 1 1 d . . H3 H 0.7900 0.5992 0.5066 0.060 Uiso 1 1 calc R U O4 O 0.72909(6) 0.8158(3) 0.58427(7) 0.0295(4) Uani 1 1 d . . P1 P 0.78168(3) 0.67418(10) 0.61192(3) 0.0261(2) Uani 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 C1 0.0544(18) 0.0530(19) 0.073(2) 0.0010(16) 0.0054(15) -0.0176(15) C2 0.0446(14) 0.0420(16) 0.0505(16) 0.0140(13) 0.0043(12) -0.0059(12) C3 0.0343(12) 0.0384(14) 0.0278(12) -0.0034(10) 0.0010(9) 0.0018(11) C4 0.0503(19) 0.070(2) 0.123(3) 0.044(2) -0.0114(19) -0.0199(17) C5 0.0440(19) 0.103(3) 0.147(4) 0.044(3) -0.007(2) -0.028(2) C6 0.0407(17) 0.108(3) 0.081(3) -0.028(2) -0.0174(16) 0.0063(19) C7 0.0415(17) 0.111(3) 0.069(2) 0.033(2) -0.0014(14) 0.0194(19) C8 0.0386(15) 0.081(2) 0.0485(17) 0.0251(15) 0.0010(12) 0.0126(15) N1 0.0371(10) 0.0245(10) 0.0185(9) -0.0006(7) -0.0016(7) 0.0003(8) O1 0.0403(9) 0.0317(9) 0.0278(8) 0.0063(7) -0.0041(7) -0.0039(7) O2 0.0508(10) 0.0294(9) 0.0214(8) 0.0031(7) -0.0021(7) -0.0057(8) O3 0.0609(11) 0.0371(10) 0.0203(8) 0.0010(7) -0.0010(7) 0.0220(9) O4 0.0365(9) 0.0328(9) 0.0187(8) -0.0011(6) 0.0009(6) 0.0058(7) P1 0.0377(4) 0.0237(3) 0.0160(3) 0.0003(2) -0.0005(2) 0.0023(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' P P 0.1023 0.0942 '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 H1D 109.5 C2 C1 H1E 109.5 H1D C1 H1E 109.5 C2 C1 H1F 109.5 H1D C1 H1F 109.5 H1E C1 H1F 109.5 O1 C2 C1 108.8(2) O1 C2 H2A 109.9 C1 C2 H2A 109.9 O1 C2 H2B 109.9 C1 C2 H2B 109.9 H2A C2 H2B 108.3 C4 C3 N1 109.6(2) C4 C3 C8 112.4(2) N1 C3 C8 109.97(19) C4 C3 H3A 108.3 N1 C3 H3A 108.3 C8 C3 H3A 108.3 C3 C4 C5 110.5(3) C3 C4 H4A 109.6 C5 C4 H4A 109.6 C3 C4 H4B 109.6 C5 C4 H4B 109.6 H4A C4 H4B 108.1 C6 C5 C4 111.2(3) C6 C5 H5A 109.4 C4 C5 H5A 109.4 C6 C5 H5B 109.4 C4 C5 H5B 109.4 H5A C5 H5B 108.0 C5 C6 C7 110.7(3) C5 C6 H6A 109.5 C7 C6 H6A 109.5 C5 C6 H6B 109.5 C7 C6 H6B 109.5 H6A C6 H6B 108.1 C6 C7 C8 110.8(3) C6 C7 H7A 109.5 C8 C7 H7A 109.5 C6 C7 H7B 109.5 C8 C7 H7B 109.5 H7A C7 H7B 108.1 C3 C8 C7 110.2(2) C3 C8 H8A 109.6 C7 C8 H8A 109.6 C3 C8 H8B 109.6 C7 C8 H8B 109.6 H8A C8 H8B 108.1 C3 N1 H1A 109.5 C3 N1 H1B 109.5 H1A N1 H1B 109.5 C3 N1 H1C 109.5 H1A N1 H1C 109.5 H1B N1 H1C 109.5 C2 O1 P1 118.31(15) P1 O3 H3 109.5 O2 P1 O4 116.74(9) O2 P1 O3 110.01(9) O4 P1 O3 110.14(8) O2 P1 O1 104.06(8) O4 P1 O1 109.01(9) O3 P1 O1 106.23(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 C2 1.494(4) C1 H1D 0.9800 C1 H1E 0.9800 C1 H1F 0.9800 C2 O1 1.449(3) C2 H2A 0.9900 C2 H2B 0.9900 C3 C4 1.492(4) C3 N1 1.493(3) C3 C8 1.505(3) C3 H3A 1.0000 C4 C5 1.544(5) C4 H4A 0.9900 C4 H4B 0.9900 C5 C6 1.495(5) C5 H5A 0.9900 C5 H5B 0.9900 C6 C7 1.507(5) C6 H6A 0.9900 C6 H6B 0.9900 C7 C8 1.543(4) C7 H7A 0.9900 C7 H7B 0.9900 C8 H8A 0.9900 C8 H8B 0.9900 N1 H1A 0.9100 N1 H1B 0.9100 N1 H1C 0.9100 O1 P1 1.5963(16) O2 P1 1.4960(15) O3 P1 1.5668(16) O3 H3 0.8400 O4 P1 1.5115(15) loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O4 0.91 1.91 2.822(2) 177.0 1_545 N1 H1B O2 0.91 1.88 2.786(2) 175.9 4_646 N1 H1C O2 0.91 1.83 2.741(2) 173.9 . O3 H3 O4 0.84 1.75 2.577(2) 168.0 7_666 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 N1 C3 C4 C5 -177.9(3) C8 C3 C4 C5 -55.3(4) C3 C4 C5 C6 55.8(5) C4 C5 C6 C7 -57.1(5) C5 C6 C7 C8 57.2(4) C4 C3 C8 C7 55.5(4) N1 C3 C8 C7 177.9(3) C6 C7 C8 C3 -55.8(4) C1 C2 O1 P1 177.02(18) C2 O1 P1 O2 179.21(17) C2 O1 P1 O4 -55.57(19) C2 O1 P1 O3 63.09(19)