#------------------------------------------------------------------------------ #$Date: 2021-11-04 03:32:32 +0200 (Thu, 04 Nov 2021) $ #$Revision: 270288 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061042.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_7061042 loop_ _publ_author_name 'Bhuin, Shouvik' 'Bhattacharya, Suman' 'Chakravarty, Manab' _publ_section_title ; Acceptor--donor--acceptor-linked triphenylamine and phenothiazine motifs as cousin molecules: the methyl effect on stimuli-responsiveness, crystallochromism, and dual-state emission ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ04190H _journal_year 2021 _chemical_formula_moiety 'C27 H20 N4' _chemical_formula_sum 'C27 H20 N4' _chemical_formula_weight 400.47 _chemical_name_common MTPADCA _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2020-02-08 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-03-09 deposited with the CCDC. 2021-10-22 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.274(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.1420(5) _cell_length_b 9.8864(6) _cell_length_c 21.3253(12) _cell_measurement_reflns_used 5965 _cell_measurement_temperature 298 _cell_measurement_theta_max 31.0980 _cell_measurement_theta_min 3.6010 _cell_volume 2121.0(2) _computing_cell_refinement 'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.20a (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 298 _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.869 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -52.00 12.00 0.50 45.00 -- -3.60 -57.00 0.00 128 2 \w -19.00 7.00 0.50 45.00 -- -3.60 -57.00 -60.00 52 3 \w -89.00 2.00 0.50 45.00 -- -3.60 -57.00-180.00 182 4 \w -85.00 -33.00 0.50 45.00 -- 3.60 -57.00 -30.00 104 5 \w -2.00 29.00 0.50 45.00 -- 3.60 -64.00 140.00 62 6 \w -78.00 -53.00 0.50 45.00 -- 3.60 -64.00 140.00 50 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Pro: Kappa dual home/near' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0573242000 _diffrn_orient_matrix_UB_12 -0.0123048000 _diffrn_orient_matrix_UB_13 -0.0219558000 _diffrn_orient_matrix_UB_21 0.0039764000 _diffrn_orient_matrix_UB_22 0.0665224000 _diffrn_orient_matrix_UB_23 -0.0120244000 _diffrn_orient_matrix_UB_31 0.0409040000 _diffrn_orient_matrix_UB_32 -0.0237740000 _diffrn_orient_matrix_UB_33 -0.0223110000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_unetI/netI 0.0374 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.869 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 22381 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.869 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 31.161 _diffrn_reflns_theta_min 3.125 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.89272 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.20a (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'metallic greenish green' _exptl_crystal_colour_lustre metallic _exptl_crystal_colour_modifier greenish _exptl_crystal_colour_primary green _exptl_crystal_density_diffrn 1.254 _exptl_crystal_description block _exptl_crystal_F_000 840 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.417 _refine_diff_density_min -0.424 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 282 _refine_ls_number_reflns 5970 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0733 _refine_ls_R_factor_gt 0.0502 _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^)+(0.0760P)^2^+0.7009P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1284 _refine_ls_wR_factor_ref 0.1438 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4462 _reflns_number_total 5970 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL exp_364-5b211218a_a.res in P2(1)/c exp_364-5b211218a.res created by SHELXL-2016/4 at 11:27:02 on 08-Feb-2020 REM Old TITL exp_364 -5B211218A in P21/c #14 REM SHELXT solution in P2(1)/c REM R1 0.141, Rweak 0.004, Alpha 0.020, Orientation as input REM Formula found by SHELXT: C27 N4 CELL 0.71073 10.141986 9.886419 21.325269 90 97.2739 90 ZERR 9 0.000523 0.000616 0.001226 0 0.005 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N UNIT 108 80 16 L.S. 10 PLAN 1 SIZE 0.2 0.2 0.1 TEMP 24.85 BOND $H LIST 6 MORE -1 CONF fmap 2 acta 52 REM REM REM WGHT 0.076000 0.700900 FVAR 0.46406 N001 3 0.738082 0.583952 0.512270 11.00000 0.01450 0.03836 = 0.02085 -0.00616 -0.00096 0.00423 AFIX 7 H00A 2 0.821072 0.596819 0.509660 11.00000 -1.20000 H00B 2 0.706283 0.653283 0.529540 11.00000 -1.20000 AFIX 0 N002 3 -0.063167 0.790455 0.317917 11.00000 0.01650 0.02809 = 0.01733 -0.00300 0.00008 0.00810 N003 3 0.453536 0.749409 0.528799 11.00000 0.02426 0.03436 = 0.02407 -0.00701 -0.00141 0.00581 N004 3 0.964207 0.400864 0.436401 11.00000 0.01993 0.05378 = 0.02883 -0.00733 -0.00120 0.00727 C005 1 0.330655 0.646855 0.362246 11.00000 0.01420 0.01810 = 0.01477 -0.00053 -0.00047 0.00074 C006 1 -0.141879 0.752817 0.261099 11.00000 0.01643 0.01616 = 0.01870 0.00308 -0.00084 0.00233 C007 1 0.230633 0.561903 0.333336 11.00000 0.01643 0.01653 = 0.01734 -0.00224 -0.00012 0.00146 AFIX 43 H007 2 0.251235 0.473184 0.323819 11.00000 -1.20000 AFIX 0 C008 1 0.467200 0.592886 0.378670 11.00000 0.01324 0.01722 = 0.01786 0.00041 0.00050 -0.00109 C009 1 0.298124 0.781100 0.374675 11.00000 0.01941 0.01806 = 0.02105 -0.00182 -0.00248 -0.00145 AFIX 43 H009 2 0.363545 0.839306 0.393486 11.00000 -1.20000 AFIX 0 C00A 1 0.523814 0.513129 0.335014 11.00000 0.01674 0.02176 = 0.01486 -0.00130 0.00033 -0.00127 AFIX 43 H00C 2 0.474230 0.493136 0.296409 11.00000 -1.20000 AFIX 0 C00B 1 0.541285 0.618653 0.437778 11.00000 0.01359 0.01924 = 0.01854 -0.00221 0.00031 -0.00038 C00C 1 0.487254 0.692849 0.486524 11.00000 0.01424 0.02410 = 0.02036 -0.00257 -0.00268 0.00057 C00D 1 0.101108 0.607910 0.318624 11.00000 0.01500 0.01986 = 0.01864 -0.00260 -0.00206 0.00034 AFIX 43 H00D 2 0.035478 0.549546 0.300142 11.00000 -1.20000 AFIX 0 C00E 1 0.652424 0.462967 0.347898 11.00000 0.01631 0.02213 = 0.01792 -0.00092 0.00368 -0.00022 C00F 1 0.725757 0.490602 0.406950 11.00000 0.01260 0.02598 = 0.02058 -0.00064 0.00140 0.00088 C00G 1 0.169125 0.828005 0.359164 11.00000 0.02239 0.01572 = 0.02165 -0.00163 -0.00057 0.00305 AFIX 43 H00G 2 0.149078 0.917627 0.367236 11.00000 -1.20000 AFIX 0 C00H 1 0.671441 0.566489 0.453799 11.00000 0.01269 0.02381 = 0.02009 -0.00075 0.00040 -0.00114 C00I 1 0.069049 0.741645 0.331502 11.00000 0.01622 0.02159 = 0.01478 0.00016 0.00054 0.00458 C00J 1 -0.082446 0.736067 0.206020 11.00000 0.02233 0.01920 = 0.02007 0.00175 0.00110 0.00170 AFIX 43 H00J 2 0.008417 0.750194 0.206853 11.00000 -1.20000 AFIX 0 C00K 1 0.858493 0.439044 0.422339 11.00000 0.01886 0.03412 = 0.02122 -0.00533 0.00236 0.00284 C00L 1 -0.118344 0.866319 0.365017 11.00000 0.02431 0.02562 = 0.01759 0.00110 0.00606 0.00839 C00M 1 0.713387 0.383406 0.298792 11.00000 0.02077 0.03190 = 0.02155 -0.00467 0.00456 0.00460 AFIX 137 H00E 2 0.645517 0.358741 0.265199 11.00000 -1.50000 H00F 2 0.754158 0.303102 0.317697 11.00000 -1.50000 H00H 2 0.779401 0.437586 0.282133 11.00000 -1.50000 AFIX 0 C00N 1 -0.278786 0.733197 0.258442 11.00000 0.01850 0.02190 = 0.03507 0.00820 0.00270 0.00182 AFIX 43 H00N 2 -0.320073 0.744695 0.294609 11.00000 -1.20000 AFIX 0 C00O 1 -0.158611 0.698363 0.149975 11.00000 0.04695 0.01969 = 0.01913 -0.00008 -0.00371 0.00363 AFIX 43 H00O 2 -0.117810 0.686559 0.113683 11.00000 -1.20000 AFIX 0 C00P 1 -0.201042 0.977201 0.348546 11.00000 0.03396 0.03130 = 0.02036 0.00451 0.00746 0.01463 AFIX 43 H00P 2 -0.219169 1.003562 0.306475 11.00000 -1.20000 AFIX 0 C00Q 1 -0.353598 0.696443 0.201726 11.00000 0.02026 0.02212 = 0.05432 0.00910 -0.01368 -0.00290 AFIX 43 H00Q 2 -0.444818 0.683996 0.200313 11.00000 -1.20000 AFIX 0 C00R 1 -0.293936 0.678135 0.147298 11.00000 0.04440 0.01921 = 0.03306 0.00211 -0.02176 -0.00019 AFIX 43 H00R 2 -0.344224 0.652665 0.109635 11.00000 -1.20000 AFIX 0 C00S 1 -0.089492 0.830132 0.428153 11.00000 0.04882 0.03550 = 0.02191 0.00747 0.01007 0.02014 AFIX 43 H00S 2 -0.034971 0.756261 0.439650 11.00000 -1.20000 AFIX 0 C00T 1 -0.256098 1.047939 0.395186 11.00000 0.04905 0.03642 = 0.03294 0.00280 0.01456 0.02395 AFIX 43 H00T 2 -0.313569 1.119713 0.384008 11.00000 -1.20000 AFIX 0 C00U 1 -0.142571 0.904951 0.474012 11.00000 0.09147 0.05956 = 0.01705 0.01093 0.01968 0.03802 AFIX 43 H00U 2 -0.121291 0.882013 0.516379 11.00000 -1.20000 AFIX 0 C00V 1 -0.226210 1.012574 0.457839 11.00000 0.07901 0.05682 = 0.02853 0.00119 0.02389 0.03502 AFIX 43 H00V 2 -0.262224 1.060989 0.488978 11.00000 -1.20000 AFIX 0 HKLF 4 REM exp_364-5b211218a_a.res in P2(1)/c REM R1 = 0.0502 for 4462 Fo > 4sig(Fo) and 0.0733 for all 5970 data REM 282 parameters refined using 0 restraints END WGHT 0.0762 0.6989 REM Highest difference peak 0.417, deepest hole -0.424, 1-sigma level 0.055 Q1 1 0.8143 0.5408 0.5233 11.00000 0.05 0.42 REM The information below was added by Olex2. REM REM R1 = 0.0502 for 4462 Fo > 4sig(Fo) and 0.0733 for all 23173 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.42, deepest hole -0.42 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0733 REM R1_gt = 0.0502 REM wR_ref = 0.1438 REM GOOF = 1.035 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 23173 REM Reflections_gt = 4462 REM Parameters = n/a REM Hole = -0.42 REM Peak = 0.42 REM Flack = n/a ; _cod_data_source_file d1nj04190h2.cif _cod_data_source_block exp_MTPADCA _cod_database_code 7061042 _shelx_shelxl_version_number 2016/4 _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_max 0.992 _shelx_estimated_absorpt_t_min 0.985 _reflns_odcompleteness_completeness 99.71 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 28.22 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Rotating group: N001(H00A,H00B) 2.b Aromatic/amide H refined with riding coordinates: C007(H007), C009(H009), C00A(H00C), C00D(H00D), C00G(H00G), C00J(H00J), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V) 2.c Idealised Me refined as rotating group: C00M(H00E,H00F,H00H) ; _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.077 _oxdiff_exptl_absorpt_empirical_full_min 0.907 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group N001 N 0.73808(11) 0.58395(14) 0.51227(5) 0.0248(3) Uani 1 1 d . . . . . H00A H 0.821072 0.596819 0.509660 0.030 Uiso 1 1 d GR . . . . H00B H 0.706283 0.653283 0.529540 0.030 Uiso 1 1 d GR . . . . N002 N -0.06317(11) 0.79045(13) 0.31792(5) 0.0208(2) Uani 1 1 d . . . . . N003 N 0.45354(12) 0.74941(14) 0.52880(6) 0.0280(3) Uani 1 1 d . . . . . N004 N 0.96421(12) 0.40086(16) 0.43640(6) 0.0346(3) Uani 1 1 d . . . . . C005 C 0.33066(11) 0.64686(13) 0.36225(6) 0.0159(2) Uani 1 1 d . . . . . C006 C -0.14188(12) 0.75282(13) 0.26110(6) 0.0174(2) Uani 1 1 d . . . . . C007 C 0.23063(12) 0.56190(13) 0.33334(6) 0.0170(2) Uani 1 1 d . . . . . H007 H 0.251235 0.473184 0.323819 0.020 Uiso 1 1 calc R . . . . C008 C 0.46720(12) 0.59289(13) 0.37867(6) 0.0162(2) Uani 1 1 d . . . . . C009 C 0.29812(13) 0.78110(14) 0.37468(6) 0.0199(3) Uani 1 1 d . . . . . H009 H 0.363545 0.839306 0.393486 0.024 Uiso 1 1 calc R . . . . C00A C 0.52381(12) 0.51313(13) 0.33501(6) 0.0179(2) Uani 1 1 d . . . . . H00C H 0.474230 0.493136 0.296409 0.022 Uiso 1 1 calc R . . . . C00B C 0.54128(12) 0.61865(13) 0.43778(6) 0.0173(2) Uani 1 1 d . . . . . C00C C 0.48725(12) 0.69285(14) 0.48652(6) 0.0200(3) Uani 1 1 d . . . . . C00D C 0.10111(12) 0.60791(13) 0.31862(6) 0.0182(3) Uani 1 1 d . . . . . H00D H 0.035478 0.549546 0.300142 0.022 Uiso 1 1 calc R . . . . C00E C 0.65242(12) 0.46297(14) 0.34790(6) 0.0187(3) Uani 1 1 d . . . . . C00F C 0.72576(12) 0.49060(14) 0.40695(6) 0.0198(3) Uani 1 1 d . . . . . C00G C 0.16913(13) 0.82800(13) 0.35916(6) 0.0202(3) Uani 1 1 d . . . . . H00G H 0.149078 0.917627 0.367236 0.024 Uiso 1 1 calc R . . . . C00H C 0.67144(12) 0.56649(14) 0.45380(6) 0.0190(3) Uani 1 1 d . . . . . C00I C 0.06905(12) 0.74164(14) 0.33150(6) 0.0176(3) Uani 1 1 d . . . . . C00J C -0.08245(13) 0.73607(14) 0.20602(6) 0.0207(3) Uani 1 1 d . . . . . H00J H 0.008417 0.750194 0.206853 0.025 Uiso 1 1 calc R . . . . C00K C 0.85849(13) 0.43904(16) 0.42234(7) 0.0247(3) Uani 1 1 d . . . . . C00L C -0.11834(13) 0.86632(15) 0.36502(6) 0.0222(3) Uani 1 1 d . . . . . C00M C 0.71339(13) 0.38341(16) 0.29879(6) 0.0246(3) Uani 1 1 d . . . . . H00E H 0.645517 0.358741 0.265199 0.037 Uiso 1 1 calc GR . . . . H00F H 0.754158 0.303102 0.317697 0.037 Uiso 1 1 calc GR . . . . H00H H 0.779401 0.437586 0.282133 0.037 Uiso 1 1 calc GR . . . . C00N C -0.27879(13) 0.73320(15) 0.25844(7) 0.0252(3) Uani 1 1 d . . . . . H00N H -0.320073 0.744695 0.294609 0.030 Uiso 1 1 calc R . . . . C00O C -0.15861(17) 0.69836(15) 0.14997(7) 0.0293(3) Uani 1 1 d . . . . . H00O H -0.117810 0.686559 0.113683 0.035 Uiso 1 1 calc R . . . . C00P C -0.20104(15) 0.97720(16) 0.34855(7) 0.0282(3) Uani 1 1 d . . . . . H00P H -0.219169 1.003562 0.306475 0.034 Uiso 1 1 calc R . . . . C00Q C -0.35360(15) 0.69644(16) 0.20173(9) 0.0338(4) Uani 1 1 d . . . . . H00Q H -0.444818 0.683996 0.200313 0.041 Uiso 1 1 calc R . . . . C00R C -0.29394(17) 0.67814(15) 0.14730(8) 0.0345(4) Uani 1 1 d . . . . . H00R H -0.344224 0.652665 0.109635 0.041 Uiso 1 1 calc R . . . . C00S C -0.08949(18) 0.83013(18) 0.42815(7) 0.0349(4) Uani 1 1 d . . . . . H00S H -0.034971 0.756261 0.439650 0.042 Uiso 1 1 calc R . . . . C00T C -0.25610(19) 1.04794(19) 0.39519(8) 0.0387(4) Uani 1 1 d . . . . . H00T H -0.313569 1.119713 0.384008 0.046 Uiso 1 1 calc R . . . . C00U C -0.1426(2) 0.9050(2) 0.47401(8) 0.0549(6) Uani 1 1 d . . . . . H00U H -0.121291 0.882013 0.516379 0.066 Uiso 1 1 calc R . . . . C00V C -0.2262(2) 1.0126(2) 0.45784(9) 0.0533(6) Uani 1 1 d . . . . . H00V H -0.262224 1.060989 0.488978 0.064 Uiso 1 1 calc R . . . . 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 N001 0.0145(5) 0.0384(7) 0.0209(6) -0.0062(5) -0.0010(4) 0.0042(5) N002 0.0165(5) 0.0281(6) 0.0173(5) -0.0030(4) 0.0001(4) 0.0081(4) N003 0.0243(6) 0.0344(7) 0.0241(6) -0.0070(5) -0.0014(5) 0.0058(5) N004 0.0199(6) 0.0538(9) 0.0288(7) -0.0073(6) -0.0012(5) 0.0073(6) C005 0.0142(5) 0.0181(6) 0.0148(5) -0.0005(4) -0.0005(4) 0.0007(5) C006 0.0164(5) 0.0162(6) 0.0187(6) 0.0031(4) -0.0008(4) 0.0023(5) C007 0.0164(5) 0.0165(6) 0.0173(6) -0.0022(4) -0.0001(4) 0.0015(5) C008 0.0132(5) 0.0172(6) 0.0179(6) 0.0004(4) 0.0005(4) -0.0011(4) C009 0.0194(6) 0.0181(6) 0.0211(6) -0.0018(5) -0.0025(5) -0.0015(5) C00A 0.0167(5) 0.0218(6) 0.0149(5) -0.0013(5) 0.0003(4) -0.0013(5) C00B 0.0136(5) 0.0192(6) 0.0185(6) -0.0022(5) 0.0003(4) -0.0004(5) C00C 0.0142(5) 0.0241(7) 0.0204(6) -0.0026(5) -0.0027(4) 0.0006(5) C00D 0.0150(5) 0.0199(6) 0.0186(6) -0.0026(5) -0.0021(4) 0.0003(5) C00E 0.0163(5) 0.0221(6) 0.0179(6) -0.0009(5) 0.0037(4) -0.0002(5) C00F 0.0126(5) 0.0260(7) 0.0206(6) -0.0006(5) 0.0014(4) 0.0009(5) C00G 0.0224(6) 0.0157(6) 0.0216(6) -0.0016(5) -0.0006(5) 0.0030(5) C00H 0.0127(5) 0.0238(7) 0.0201(6) -0.0007(5) 0.0004(4) -0.0011(5) C00I 0.0162(5) 0.0216(6) 0.0148(5) 0.0002(5) 0.0005(4) 0.0046(5) C00J 0.0223(6) 0.0192(6) 0.0201(6) 0.0018(5) 0.0011(5) 0.0017(5) C00K 0.0189(6) 0.0341(8) 0.0212(6) -0.0053(5) 0.0024(5) 0.0028(6) C00L 0.0243(6) 0.0256(7) 0.0176(6) 0.0011(5) 0.0061(5) 0.0084(5) C00M 0.0208(6) 0.0319(7) 0.0215(6) -0.0047(5) 0.0046(5) 0.0046(6) C00N 0.0185(6) 0.0219(7) 0.0351(8) 0.0082(6) 0.0027(5) 0.0018(5) C00O 0.0469(9) 0.0197(7) 0.0191(6) -0.0001(5) -0.0037(6) 0.0036(6) C00P 0.0340(8) 0.0313(8) 0.0204(6) 0.0045(6) 0.0075(5) 0.0146(6) C00Q 0.0203(7) 0.0221(7) 0.0543(10) 0.0091(7) -0.0137(6) -0.0029(6) C00R 0.0444(9) 0.0192(7) 0.0331(8) 0.0021(6) -0.0218(7) -0.0002(6) C00S 0.0488(9) 0.0355(9) 0.0219(7) 0.0075(6) 0.0101(6) 0.0201(8) C00T 0.0491(10) 0.0364(9) 0.0329(8) 0.0028(7) 0.0146(7) 0.0240(8) C00U 0.0915(16) 0.0596(13) 0.0171(7) 0.0109(8) 0.0197(8) 0.0380(12) C00V 0.0790(15) 0.0568(12) 0.0285(8) 0.0012(8) 0.0239(9) 0.0350(11) 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 _geom_angle_site_symmetry_3 _geom_angle_publ_flag H00A N001 H00B 109.5 . . ? C00H N001 H00A 109.8 . . ? C00H N001 H00B 109.0 . . ? C006 N002 C00I 120.10(10) . . ? C006 N002 C00L 120.90(10) . . ? C00I N002 C00L 118.72(10) . . ? C007 C005 C008 119.42(11) . . ? C007 C005 C009 118.50(11) . . ? C009 C005 C008 122.08(11) . . ? C00J C006 N002 119.68(11) . . ? C00N C006 N002 121.48(12) . . ? C00N C006 C00J 118.85(12) . . ? C005 C007 H007 119.5 . . ? C00D C007 C005 121.04(12) . . ? C00D C007 H007 119.5 . . ? C00A C008 C005 119.70(11) . . ? C00A C008 C00B 118.76(11) . . ? C00B C008 C005 121.54(11) . . ? C005 C009 H009 119.7 . . ? C00G C009 C005 120.59(12) . . ? C00G C009 H009 119.7 . . ? C008 C00A H00C 119.2 . . ? C00E C00A C008 121.60(11) . . ? C00E C00A H00C 119.2 . . ? C008 C00B C00C 122.11(11) . . ? C008 C00B C00H 121.69(11) . . ? C00H C00B C00C 116.11(11) . . ? N003 C00C C00B 174.26(13) . . ? C007 C00D H00D 119.9 . . ? C007 C00D C00I 120.19(12) . . ? C00I C00D H00D 119.9 . . ? C00A C00E C00F 118.98(12) . . ? C00A C00E C00M 120.48(11) . . ? C00F C00E C00M 120.52(11) . . ? C00E C00F C00H 121.75(11) . . ? C00E C00F C00K 120.62(12) . . ? C00H C00F C00K 117.61(11) . . ? C009 C00G H00G 119.7 . . ? C009 C00G C00I 120.56(12) . . ? C00I C00G H00G 119.7 . . ? N001 C00H C00B 121.14(12) . . ? N001 C00H C00F 121.66(11) . . ? C00F C00H C00B 117.15(11) . . ? C00D C00I N002 121.25(12) . . ? C00D C00I C00G 119.09(11) . . ? C00G C00I N002 119.66(12) . . ? C006 C00J H00J 119.9 . . ? C00O C00J C006 120.22(13) . . ? C00O C00J H00J 119.9 . . ? N004 C00K C00F 177.61(16) . . ? C00P C00L N002 120.85(12) . . ? C00S C00L N002 119.68(12) . . ? C00S C00L C00P 119.47(13) . . ? C00E C00M H00E 109.5 . . ? C00E C00M H00F 109.5 . . ? C00E C00M H00H 109.5 . . ? H00E C00M H00F 109.5 . . ? H00E C00M H00H 109.5 . . ? H00F C00M H00H 109.5 . . ? C006 C00N H00N 120.0 . . ? C00Q C00N C006 120.09(14) . . ? C00Q C00N H00N 120.0 . . ? C00J C00O H00O 119.5 . . ? C00R C00O C00J 121.05(15) . . ? C00R C00O H00O 119.5 . . ? C00L C00P H00P 120.1 . . ? C00T C00P C00L 119.84(13) . . ? C00T C00P H00P 120.1 . . ? C00N C00Q H00Q 119.6 . . ? C00R C00Q C00N 120.90(14) . . ? C00R C00Q H00Q 119.6 . . ? C00O C00R C00Q 118.89(13) . . ? C00O C00R H00R 120.6 . . ? C00Q C00R H00R 120.6 . . ? C00L C00S H00S 120.2 . . ? C00L C00S C00U 119.55(15) . . ? C00U C00S H00S 120.2 . . ? C00P C00T H00T 119.7 . . ? C00V C00T C00P 120.51(15) . . ? C00V C00T H00T 119.7 . . ? C00S C00U H00U 119.4 . . ? C00V C00U C00S 121.12(16) . . ? C00V C00U H00U 119.4 . . ? C00T C00V H00V 120.3 . . ? C00U C00V C00T 119.47(16) . . ? C00U C00V H00V 120.3 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N001 H00A 0.8600 . ? N001 H00B 0.8600 . ? N001 C00H 1.3520(16) . ? N002 C006 1.4138(16) . ? N002 C00I 1.4200(16) . ? N002 C00L 1.4237(17) . ? N003 C00C 1.1491(18) . ? N004 C00K 1.1404(19) . ? C005 C007 1.3986(17) . ? C005 C008 1.4840(16) . ? C005 C009 1.4010(18) . ? C006 C00J 1.3963(18) . ? C006 C00N 1.3960(18) . ? C007 H007 0.9300 . ? C007 C00D 1.3880(17) . ? C008 C00A 1.3977(18) . ? C008 C00B 1.4066(16) . ? C009 H009 0.9300 . ? C009 C00G 1.3880(18) . ? C00A H00C 0.9300 . ? C00A C00E 1.3900(18) . ? C00B C00C 1.4364(18) . ? C00B C00H 1.4181(17) . ? C00D H00D 0.9300 . ? C00D C00I 1.3971(18) . ? C00E C00F 1.4059(18) . ? C00E C00M 1.5038(18) . ? C00F C00H 1.4156(18) . ? C00F C00K 1.4380(18) . ? C00G H00G 0.9300 . ? C00G C00I 1.3984(18) . ? C00J H00J 0.9300 . ? C00J C00O 1.3894(19) . ? C00L C00P 1.3978(19) . ? C00L C00S 1.3880(19) . ? C00M H00E 0.9600 . ? C00M H00F 0.9600 . ? C00M H00H 0.9600 . ? C00N H00N 0.9300 . ? C00N C00Q 1.392(2) . ? C00O H00O 0.9300 . ? C00O C00R 1.381(2) . ? C00P H00P 0.9300 . ? C00P C00T 1.390(2) . ? C00Q H00Q 0.9300 . ? C00Q C00R 1.387(3) . ? C00R H00R 0.9300 . ? C00S H00S 0.9300 . ? C00S C00U 1.388(2) . ? C00T H00T 0.9300 . ? C00T C00V 1.377(2) . ? C00U H00U 0.9300 . ? C00U C00V 1.377(3) . ? C00V H00V 0.9300 . ? 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 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N002 C006 C00J C00O 179.64(12) . . . . ? N002 C006 C00N C00Q 179.86(13) . . . . ? N002 C00L C00P C00T 178.60(15) . . . . ? N002 C00L C00S C00U 179.48(18) . . . . ? C005 C007 C00D C00I 1.23(19) . . . . ? C005 C008 C00A C00E 178.58(12) . . . . ? C005 C008 C00B C00C 3.0(2) . . . . ? C005 C008 C00B C00H 179.57(12) . . . . ? C005 C009 C00G C00I 0.7(2) . . . . ? C006 N002 C00I C00D -41.08(18) . . . . ? C006 N002 C00I C00G 139.89(13) . . . . ? C006 N002 C00L C00P -44.2(2) . . . . ? C006 N002 C00L C00S 135.97(15) . . . . ? C006 C00J C00O C00R 0.7(2) . . . . ? C006 C00N C00Q C00R 0.3(2) . . . . ? C007 C005 C008 C00A 44.52(17) . . . . ? C007 C005 C008 C00B -134.70(13) . . . . ? C007 C005 C009 C00G 0.64(19) . . . . ? C007 C00D C00I N002 -178.88(12) . . . . ? C007 C00D C00I C00G 0.16(19) . . . . ? C008 C005 C007 C00D 178.49(12) . . . . ? C008 C005 C009 C00G -179.47(12) . . . . ? C008 C00A C00E C00F 1.6(2) . . . . ? C008 C00A C00E C00M -176.84(13) . . . . ? C008 C00B C00H N001 -175.33(13) . . . . ? C008 C00B C00H C00F 1.95(19) . . . . ? C009 C005 C007 C00D -1.62(19) . . . . ? C009 C005 C008 C00A -135.37(13) . . . . ? C009 C005 C008 C00B 45.41(18) . . . . ? C009 C00G C00I N002 177.93(12) . . . . ? C009 C00G C00I C00D -1.1(2) . . . . ? C00A C008 C00B C00C -176.24(12) . . . . ? C00A C008 C00B C00H 0.34(19) . . . . ? C00A C00E C00F C00H 0.9(2) . . . . ? C00A C00E C00F C00K 179.21(13) . . . . ? C00B C008 C00A C00E -2.18(19) . . . . ? C00C C00B C00H N001 1.45(19) . . . . ? C00C C00B C00H C00F 178.73(12) . . . . ? C00E C00F C00H N001 174.70(13) . . . . ? C00E C00F C00H C00B -2.6(2) . . . . ? C00I N002 C006 C00J -35.22(19) . . . . ? C00I N002 C006 C00N 145.47(13) . . . . ? C00I N002 C00L C00P 141.89(14) . . . . ? C00I N002 C00L C00S -37.9(2) . . . . ? C00J C006 C00N C00Q 0.5(2) . . . . ? C00J C00O C00R C00Q 0.2(2) . . . . ? C00K C00F C00H N001 -3.7(2) . . . . ? C00K C00F C00H C00B 179.03(13) . . . . ? C00L N002 C006 C00J 150.96(13) . . . . ? C00L N002 C006 C00N -28.3(2) . . . . ? C00L N002 C00I C00D 132.86(14) . . . . ? C00L N002 C00I C00G -46.17(18) . . . . ? C00L C00P C00T C00V 2.2(3) . . . . ? C00L C00S C00U C00V 1.7(4) . . . . ? C00M C00E C00F C00H 179.29(13) . . . . ? C00M C00E C00F C00K -2.3(2) . . . . ? C00N C006 C00J C00O -1.0(2) . . . . ? C00N C00Q C00R C00O -0.7(2) . . . . ? C00P C00L C00S C00U -0.3(3) . . . . ? C00P C00T C00V C00U -0.9(4) . . . . ? C00S C00L C00P C00T -1.6(3) . . . . ? C00S C00U C00V C00T -1.0(4) . . . . ?