#------------------------------------------------------------------------------ #$Date: 2017-08-02 05:23:24 +0300 (Wed, 02 Aug 2017) $ #$Revision: 199448 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/88/7228826.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_7228826 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 'C9 H22 N O4 P' _chemical_formula_weight 239.24 _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 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 107.778(8) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.4545(12) _cell_length_b 6.1394(4) _cell_length_c 16.6944(12) _cell_measurement_reflns_used 2309 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 24.999 _cell_measurement_theta_min 3.180 _cell_volume 1313.15(18) _computing_data_reduction 'ShelXT (Sheldrick, 2015)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'OXFORD DIFFRACTIOM X CALIBUR-S' _diffrn_measurement_method 'omega(w)-q scan' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0509 _diffrn_reflns_av_unetI/netI 0.0447 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 8427 _diffrn_reflns_point_group_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 24.999 _diffrn_reflns_theta_max 24.999 _diffrn_reflns_theta_min 3.180 _exptl_absorpt_coefficient_mu 0.206 _exptl_absorpt_correction_T_max 0.735 _exptl_absorpt_correction_T_min 0.654 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.210 _exptl_crystal_description needles _exptl_crystal_F_000 520 _exptl_crystal_size_max 0.230 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.140 _refine_diff_density_max 0.820 _refine_diff_density_min -0.492 _refine_diff_density_rms 0.125 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.136 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 140 _refine_ls_number_reflns 2309 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.136 _refine_ls_R_factor_all 0.1070 _refine_ls_R_factor_gt 0.0935 _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/[\s^2^(Fo^2^)+(0.0800P)^2^+13.9616P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2879 _refine_ls_wR_factor_ref 0.2919 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1822 _reflns_number_total 2309 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ce01066d2.cif _cod_data_source_block 3 _cod_database_code 7228826 _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 0.954 _shelx_estimated_absorpt_t_max 0.972 _shelx_res_file ; shelx.res created by SHELXL-2014/7 TITL rm308_a.res in P2(1)/n CELL 0.71073 13.4545 6.1394 16.6944 90.000 107.778 90.000 ZERR 4.00 0.0012 0.0004 0.0012 0.000 0.008 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H N O P UNIT 36 88 4 16 4 MERG 2 OMIT -3.00 50.00 MORE -1 EQIV $1 -x, -y+2, -z HTAB O3 O4_$1 HTAB N1 O2 EQIV $2 -x+1/2, y-1/2, -z+1/2 HTAB N1 O3_$2 EQIV $3 -x+1/2, y+1/2, -z+1/2 HTAB N1 O4_$3 FMAP 2 PLAN 20 SIZE 0.140 0.180 0.230 ACTA 52.00 BOND $H CONF LIST 4 L.S. 60 TEMP -123.00 WGHT 0.080000 13.961600 FVAR 0.66522 P1 5 0.062987 1.033496 0.132610 11.00000 0.03358 0.02286 = 0.01733 0.00037 0.00288 0.00248 O4 4 0.063074 0.834072 0.080399 11.00000 0.03699 0.02127 = 0.01877 0.00052 0.00036 0.00548 O2 4 0.167460 1.128579 0.177956 11.00000 0.03985 0.03357 = 0.02196 0.00321 0.00220 -0.00527 O3 4 -0.011687 1.208959 0.078590 11.00000 0.05176 0.03281 = 0.01791 -0.00067 0.00023 0.01742 AFIX 147 H3 2 -0.028360 1.173615 0.027593 11.00000 -1.50000 AFIX 0 O1 4 0.014304 0.976000 0.205627 11.00000 0.03804 0.03992 = 0.02207 -0.00287 0.00756 -0.00820 N1 3 0.275284 1.043656 0.344234 11.00000 0.03353 0.02064 = 0.02176 0.00201 0.00096 -0.00025 AFIX 137 H1A 2 0.243489 1.086917 0.290337 11.00000 -1.20000 H1B 2 0.299261 0.905044 0.344284 11.00000 -1.20000 H1C 2 0.329741 1.134126 0.368486 11.00000 -1.20000 AFIX 0 C5 1 0.250080 0.965652 0.482074 11.00000 0.03246 0.04914 = 0.03086 0.00996 0.00457 -0.00037 AFIX 23 H5A 2 0.271706 0.812234 0.479781 11.00000 -1.20000 H5B 2 0.313008 1.052724 0.510170 11.00000 -1.20000 AFIX 0 C4 1 0.199124 1.051627 0.392564 11.00000 0.02703 0.02821 = 0.02845 -0.00022 0.00210 -0.00613 AFIX 13 H4 2 0.138958 0.954760 0.364081 11.00000 -1.20000 AFIX 0 C9 1 0.158518 1.282086 0.392108 11.00000 0.04532 0.03725 = 0.03928 0.00446 0.01506 0.00747 AFIX 23 H9A 2 0.122710 1.327633 0.333488 11.00000 -1.20000 H9B 2 0.217763 1.382498 0.415948 11.00000 -1.20000 AFIX 0 C2 1 -0.084151 0.858882 0.186740 11.00000 0.03589 0.04406 = 0.03563 -0.00447 0.00897 -0.00525 AFIX 13 H2A 2 -0.116718 0.852296 0.124343 11.00000 -1.20000 AFIX 0 C3 1 -0.152912 0.988783 0.224103 11.00000 0.04356 0.05160 = 0.05812 -0.01402 0.01572 0.00132 AFIX 137 H3A 2 -0.122656 0.991674 0.285453 11.00000 -1.50000 H3B 2 -0.222318 0.921941 0.209144 11.00000 -1.50000 H3C 2 -0.158851 1.137917 0.202215 11.00000 -1.50000 AFIX 0 C6 1 0.172444 0.980990 0.531679 11.00000 0.04013 0.07735 = 0.04066 0.01821 0.01494 0.00086 AFIX 23 H6A 2 0.112650 0.883180 0.506147 11.00000 -1.20000 H6B 2 0.206382 0.931685 0.590125 11.00000 -1.20000 AFIX 0 C1 1 -0.062601 0.629750 0.220719 11.00000 0.05445 0.04441 = 0.08104 -0.00077 0.02736 -0.00795 AFIX 137 H1D 2 -0.021733 0.551833 0.190263 11.00000 -1.50000 H1E 2 -0.128841 0.553600 0.213224 11.00000 -1.50000 H1F 2 -0.023256 0.635244 0.280701 11.00000 -1.50000 AFIX 0 C8 1 0.082247 1.295841 0.443895 11.00000 0.05043 0.05925 = 0.05096 0.00009 0.02413 0.01113 AFIX 23 H8A 2 0.060192 1.448972 0.446138 11.00000 -1.20000 H8B 2 0.019315 1.208152 0.416404 11.00000 -1.20000 AFIX 0 C7 1 0.132914 1.212163 0.532881 11.00000 0.05030 0.09487 = 0.03459 -0.01191 0.01942 0.00024 AFIX 23 H7A 2 0.191871 1.308351 0.562161 11.00000 -1.20000 H7B 2 0.081387 1.215797 0.564373 11.00000 -1.20000 AFIX 0 HKLF 4 REM rm308_a.res in P2(1)/n REM R1 = 0.0935 for 1822 Fo > 4sig(Fo) and 0.1070 for all 2309 data REM 140 parameters refined using 0 restraints END WGHT 0.0800 13.9616 REM Highest difference peak 0.820, deepest hole -0.492, 1-sigma level 0.125 Q1 1 0.0929 1.0356 0.2851 11.00000 0.05 0.82 Q2 1 -0.1791 1.0197 0.0538 11.00000 0.05 0.74 Q3 1 -0.0214 0.9694 0.0228 11.00000 0.05 0.68 Q4 1 0.2757 1.0463 0.2040 11.00000 0.05 0.50 Q5 1 0.2535 1.3224 0.4994 11.00000 0.05 0.50 Q6 1 0.3100 1.0499 0.2205 11.00000 0.05 0.49 Q7 1 0.0236 1.1897 0.2326 11.00000 0.05 0.46 Q8 1 -0.1096 1.0297 0.3642 11.00000 0.05 0.45 Q9 1 0.3119 0.6874 0.5062 11.00000 0.05 0.44 Q10 1 0.2607 1.5285 0.4425 11.00000 0.05 0.43 Q11 1 0.1006 0.8476 0.2282 11.00000 0.05 0.41 Q12 1 0.2287 1.1751 0.1528 11.00000 0.05 0.40 Q13 1 0.4007 0.9166 0.5751 11.00000 0.05 0.38 Q14 1 0.2372 0.9746 0.2779 11.00000 0.05 0.36 Q15 1 0.1447 1.0272 0.0945 11.00000 0.05 0.35 Q16 1 0.0257 1.0084 0.4306 11.00000 0.05 0.35 Q17 1 0.0932 0.6723 0.3442 11.00000 0.05 0.35 Q18 1 0.2003 0.9841 0.6583 11.00000 0.05 0.34 Q19 1 0.4262 0.9714 0.5627 11.00000 0.05 0.34 Q20 1 -0.0430 1.0286 0.1727 11.00000 0.05 0.34 ; _shelx_res_checksum 46546 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_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 P1 P 0.06299(14) 1.0335(3) 0.13261(10) 0.0257(5) Uani 1 1 d . . O4 O 0.0631(4) 0.8341(7) 0.0804(3) 0.0275(11) Uani 1 1 d . . O2 O 0.1675(4) 1.1286(8) 0.1780(3) 0.0334(12) Uani 1 1 d . . O3 O -0.0117(4) 1.2090(8) 0.0786(3) 0.0365(13) Uani 1 1 d . . H3 H -0.0284 1.1736 0.0276 0.055 Uiso 1 1 calc R U O1 O 0.0143(4) 0.9760(8) 0.2056(3) 0.0337(12) Uani 1 1 d . . N1 N 0.2753(4) 1.0437(9) 0.3442(3) 0.0270(13) Uani 1 1 d . . H1A H 0.2435 1.0869 0.2903 0.032 Uiso 1 1 calc R U H1B H 0.2993 0.9050 0.3443 0.032 Uiso 1 1 calc R U H1C H 0.3297 1.1341 0.3685 0.032 Uiso 1 1 calc R U C5 C 0.2501(6) 0.9657(14) 0.4821(5) 0.0386(18) Uani 1 1 d . . H5A H 0.2717 0.8122 0.4798 0.046 Uiso 1 1 calc R U H5B H 0.3130 1.0527 0.5102 0.046 Uiso 1 1 calc R U C4 C 0.1991(5) 1.0516(11) 0.3926(4) 0.0293(15) Uani 1 1 d . . H4 H 0.1390 0.9548 0.3641 0.035 Uiso 1 1 calc R U C9 C 0.1585(6) 1.2821(13) 0.3921(5) 0.0401(19) Uani 1 1 d . . H9A H 0.1227 1.3276 0.3335 0.048 Uiso 1 1 calc R U H9B H 0.2178 1.3825 0.4159 0.048 Uiso 1 1 calc R U C2 C -0.0842(6) 0.8589(13) 0.1867(5) 0.0390(18) Uani 1 1 d . . H2A H -0.1167 0.8523 0.1243 0.047 Uiso 1 1 calc R U C3 C -0.1529(7) 0.9888(15) 0.2241(6) 0.051(2) Uani 1 1 d . . H3A H -0.1227 0.9917 0.2855 0.077 Uiso 1 1 calc R U H3B H -0.2223 0.9219 0.2091 0.077 Uiso 1 1 calc R U H3C H -0.1589 1.1379 0.2022 0.077 Uiso 1 1 calc R U C6 C 0.1724(7) 0.9810(17) 0.5317(5) 0.052(2) Uani 1 1 d . . H6A H 0.1126 0.8832 0.5061 0.063 Uiso 1 1 calc R U H6B H 0.2064 0.9317 0.5901 0.063 Uiso 1 1 calc R U C1 C -0.0626(7) 0.6297(15) 0.2207(7) 0.058(3) Uani 1 1 d . . H1D H -0.0217 0.5518 0.1903 0.088 Uiso 1 1 calc R U H1E H -0.1288 0.5536 0.2132 0.088 Uiso 1 1 calc R U H1F H -0.0233 0.6352 0.2807 0.088 Uiso 1 1 calc R U C8 C 0.0822(7) 1.2958(16) 0.4439(5) 0.052(2) Uani 1 1 d . . H8A H 0.0602 1.4490 0.4461 0.062 Uiso 1 1 calc R U H8B H 0.0193 1.2082 0.4164 0.062 Uiso 1 1 calc R U C7 C 0.1329(7) 1.2122(19) 0.5329(5) 0.058(3) Uani 1 1 d . . H7A H 0.1919 1.3084 0.5622 0.070 Uiso 1 1 calc R U H7B H 0.0814 1.2158 0.5644 0.070 Uiso 1 1 calc R U 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 P1 0.0336(10) 0.0229(9) 0.0173(8) 0.0004(7) 0.0029(7) 0.0025(7) O4 0.037(3) 0.021(2) 0.019(2) 0.0005(19) 0.0004(19) 0.005(2) O2 0.040(3) 0.034(3) 0.022(2) 0.003(2) 0.002(2) -0.005(2) O3 0.052(3) 0.033(3) 0.018(2) -0.001(2) 0.000(2) 0.017(2) O1 0.038(3) 0.040(3) 0.022(2) -0.003(2) 0.008(2) -0.008(2) N1 0.034(3) 0.021(3) 0.022(3) 0.002(2) 0.001(2) 0.000(2) C5 0.032(4) 0.049(5) 0.031(4) 0.010(4) 0.005(3) 0.000(4) C4 0.027(3) 0.028(4) 0.028(4) 0.000(3) 0.002(3) -0.006(3) C9 0.045(5) 0.037(4) 0.039(4) 0.004(3) 0.015(4) 0.007(4) C2 0.036(4) 0.044(5) 0.036(4) -0.004(4) 0.009(3) -0.005(3) C3 0.044(5) 0.052(5) 0.058(5) -0.014(4) 0.016(4) 0.001(4) C6 0.040(5) 0.077(7) 0.041(5) 0.018(5) 0.015(4) 0.001(4) C1 0.054(6) 0.044(5) 0.081(7) -0.001(5) 0.027(5) -0.008(4) C8 0.050(5) 0.059(6) 0.051(5) 0.000(4) 0.024(4) 0.011(4) C7 0.050(5) 0.095(8) 0.035(5) -0.012(5) 0.019(4) 0.000(5) 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 O2 P1 O4 116.4(3) O2 P1 O3 111.3(3) O4 P1 O3 110.0(3) O2 P1 O1 104.0(3) O4 P1 O1 109.7(3) O3 P1 O1 104.7(3) P1 O3 H3 109.5 C2 O1 P1 120.3(4) C4 N1 H1A 109.5 C4 N1 H1B 109.5 H1A N1 H1B 109.5 C4 N1 H1C 109.5 H1A N1 H1C 109.5 H1B N1 H1C 109.5 C6 C5 C4 109.4(6) C6 C5 H5A 109.8 C4 C5 H5A 109.8 C6 C5 H5B 109.8 C4 C5 H5B 109.8 H5A C5 H5B 108.2 N1 C4 C9 109.6(6) N1 C4 C5 109.9(5) C9 C4 C5 112.3(6) N1 C4 H4 108.3 C9 C4 H4 108.3 C5 C4 H4 108.3 C4 C9 C8 110.5(7) C4 C9 H9A 109.5 C8 C9 H9A 109.5 C4 C9 H9B 109.5 C8 C9 H9B 109.5 H9A C9 H9B 108.1 O1 C2 C3 106.5(6) O1 C2 C1 108.7(6) C3 C2 C1 114.4(7) O1 C2 H2A 109.0 C3 C2 H2A 109.0 C1 C2 H2A 109.0 C2 C3 H3A 109.5 C2 C3 H3B 109.5 H3A C3 H3B 109.5 C2 C3 H3C 109.5 H3A C3 H3C 109.5 H3B C3 H3C 109.5 C7 C6 C5 111.5(7) C7 C6 H6A 109.3 C5 C6 H6A 109.3 C7 C6 H6B 109.3 C5 C6 H6B 109.3 H6A C6 H6B 108.0 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 C7 C8 C9 110.8(7) C7 C8 H8A 109.5 C9 C8 H8A 109.5 C7 C8 H8B 109.5 C9 C8 H8B 109.5 H8A C8 H8B 108.1 C6 C7 C8 110.9(8) C6 C7 H7A 109.5 C8 C7 H7A 109.5 C6 C7 H7B 109.5 C8 C7 H7B 109.5 H7A C7 H7B 108.0 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance P1 O2 1.497(5) P1 O4 1.503(5) P1 O3 1.559(5) P1 O1 1.590(5) O3 H3 0.8400 O1 C2 1.455(9) N1 C4 1.486(9) N1 H1A 0.9100 N1 H1B 0.9100 N1 H1C 0.9100 C5 C6 1.521(11) C5 C4 1.535(9) C5 H5A 0.9900 C5 H5B 0.9900 C4 C9 1.516(10) C4 H4 1.0000 C9 C8 1.533(11) C9 H9A 0.9900 C9 H9B 0.9900 C2 C3 1.494(11) C2 C1 1.511(12) C2 H2A 1.0000 C3 H3A 0.9800 C3 H3B 0.9800 C3 H3C 0.9800 C6 C7 1.518(14) C6 H6A 0.9900 C6 H6B 0.9900 C1 H1D 0.9800 C1 H1E 0.9800 C1 H1F 0.9800 C8 C7 1.522(12) C8 H8A 0.9900 C8 H8B 0.9900 C7 H7A 0.9900 C7 H7B 0.9900 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 O3 H3 O4 0.84 1.72 2.544(6) 166.6 3_575 N1 H1A O2 0.91 1.86 2.761(7) 170.1 . N1 H1B O3 0.91 3.00 3.674(8) 131.7 2_545 N1 H1C O4 0.91 1.89 2.797(7) 176.6 2 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 O2 P1 O1 C2 -173.8(5) O4 P1 O1 C2 -48.7(6) O3 P1 O1 C2 69.3(6) C6 C5 C4 N1 178.3(7) C6 C5 C4 C9 56.1(9) N1 C4 C9 C8 -178.3(6) C5 C4 C9 C8 -55.9(8) P1 O1 C2 C3 -128.1(6) P1 O1 C2 C1 108.2(7) C4 C5 C6 C7 -56.5(9) C4 C9 C8 C7 55.4(10) C5 C6 C7 C8 57.7(10) C9 C8 C7 C6 -56.4(10)