#------------------------------------------------------------------------------ #$Date: 2024-09-17 04:11:17 +0300 (Tue, 17 Sep 2024) $ #$Revision: 294768 $ #$URL: file:///home/coder/svn-repositories/cod/cif/3/00/04/3000471.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_3000471 loop_ _publ_author_name 'Deka, Poonam' 'Jaiswal, Shilpi' 'Sarma, Parishmita' 'Bora, Debajit' 'Nakane, Takanori' 'Kawamoto, Akihiro' 'Kurisu, Genji' 'Mahanta, Sanjeev Pran' 'Patra, Abhijit' 'Ichiyanagi, Kouhei' 'Sasaki, Toshiyuki' 'Thakuria, Ranjit' _publ_section_title ; Analysis of Solid-State Emission of the p-Bis(2,2-dicyanovinyl)benzene Analogue through Combined X-ray, Synchrotron, and Microcrystal Electron Diffraction ; _journal_name_full 'Crystal Growth & Design' _journal_page_first 7222 _journal_page_last 7234 _journal_paper_doi 10.1021/acs.cgd.4c00856 _journal_volume 24 _journal_year 2024 _chemical_formula_moiety 'C14 H10 O2' _chemical_formula_sum 'C14 H10 O2' _chemical_formula_weight 210.23 _space_group_crystal_system orthorhombic _space_group_IT_number 43 _space_group_name_Hall 'F 2 -2d' _space_group_name_H-M_alt 'F d d 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2023-05-31 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 15.213 _cell_length_b 37.104 _cell_length_c 3.805 _cell_measurement_reflns_used 665 _cell_measurement_temperature 79 _cell_measurement_theta_max 0.8516496039453811 _cell_measurement_theta_min 0.18251886102793313 _cell_volume 2147.782 _computing_cell_refinement 'dials.two_theta_refine (Waterman et al., 2016)' _computing_data_collection 'Verlox (Thermo Fisher Scientific) and SerialEM (Mastronarde, 2005)' _computing_data_reduction 'dials.scale (Beilsten-Edmands et al., 2020)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 79 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device_type ; Talos Arctica G2 ; _diffrn_radiation_type electrons _diffrn_radiation_wavelength 0.02508 _diffrn_reflns_av_R_equivalents 0.2659 _diffrn_reflns_av_unetI/netI 0.2235 _diffrn_reflns_Laue_measured_fraction_full 0.984 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_l_max 4 _diffrn_reflns_limit_l_min -4 _diffrn_reflns_number 3308 _diffrn_reflns_point_group_measured_fraction_full 0.972 _diffrn_reflns_point_group_measured_fraction_max 0.972 _diffrn_reflns_theta_full 0.756 _diffrn_reflns_theta_max 0.756 _diffrn_reflns_theta_min 0.150 _exptl_absorpt_coefficient_mu 0.000 _exptl_crystal_density_diffrn 1.300 _exptl_crystal_description plate _exptl_crystal_F_000 347 _refine_diff_density_max 0.140 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.044 _refine_ls_abs_structure_details ; All f" are zero, so absolute structure could not be determined ; _refine_ls_extinction_coef 95636(76) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.261 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 74 _refine_ls_number_reflns 622 _refine_ls_number_restraints 52 _refine_ls_restrained_S_all 1.206 _refine_ls_R_factor_all 0.1519 _refine_ls_R_factor_gt 0.1339 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.3188 _refine_ls_wR_factor_ref 0.3280 _reflns_Friedel_coverage 0.663 _reflns_Friedel_fraction_full 0.954 _reflns_Friedel_fraction_max 0.954 _reflns_number_gt 484 _reflns_number_total 622 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file BP2-Start.cif _cod_data_source_block bp2-start _cod_depositor_comments 'Releasing structure 3000471 into public domain as published material.' _cod_original_cell_volume 2147.9 _cod_database_code 3000471 _shelx_shelxl_version_number 2018/3 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2. Rigid body (RIGU) restrains All non-hydrogen atoms with sigma for 1-2 distances of 0.05 and sigma for 1-3 distances of 0.05 3.a Aromatic/amide H refined with riding coordinates: C9(H9), C002(H002), C003(H003), C005(H005), C007(H007) ; _shelx_res_file ; TITL bp2-another_a.res in Fdd2 bp2-another.res created by SHELXL-2018/3 at 19:06:15 on 31-May-2023 REM Old TITL BP2-another in F 2 2 2 REM SHELXT solution in Fdd2: R1 0.272, Rweak 0.175, Alpha 0.109 REM 3.568 for 23 systematic absences, Orientation a'=b, b'=c, c'=a REM Flack x = -9.990 ( 9.990 ) from 174 Parsons' quotients REM Formula found by SHELXT: C6 N2 CELL 0.02508 15.2134 37.1043 3.8051 90 90 90 ZERR 8 0 0 0 0 0 0 LATT -4 SYMM -X,-Y,+Z SYMM 0.25+X,0.25-Y,0.25+Z SYMM 0.25-X,0.25+Y,0.25+Z SFAC C 0.731 36.995 1.195 11.297 0.456 2.814 0.125 0.346 0 0 0 0 0.77 12.011 SFAC H 0.375 15.495 0.141 4.126 0.022 0.025 -0.101 46.884 0 0 0 0 0.32 1.008 SFAC O 0.455 23.78 0.917 7.622 0.472 2.144 0.138 0.296 0 0 0 0 0.73 15.999 UNIT 112 80 16 RIGU 0.05 0.05 L.S. 100 PLAN 5 CONF list 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.200000 EXTI95636.296875 FVAR 2.63208 C9 1 0.370056 0.742576 0.375715 11.00000 0.06351 0.06159 = 0.05375 -0.02206 -0.01083 -0.00241 AFIX 43 H9 2 0.381566 0.764937 0.275357 11.00000 -1.20000 AFIX 0 C002 1 0.265647 0.699756 0.608310 11.00000 0.05289 0.05243 = 0.07792 -0.01321 0.01207 -0.00676 AFIX 43 H002 2 0.209385 0.693409 0.681143 11.00000 -1.20000 AFIX 0 C003 1 0.332246 0.674246 0.601141 11.00000 0.05998 0.05736 = 0.07655 0.02128 0.00978 -0.00628 AFIX 43 H003 2 0.317556 0.651108 0.674504 11.00000 -1.20000 AFIX 0 O1 3 0.558900 0.656253 0.386213 11.00000 0.07959 0.10125 = 0.10070 -0.00428 0.00093 0.00216 C005 1 0.435507 0.719841 0.385054 11.00000 0.08614 0.10801 = 0.02205 0.01556 0.02466 0.00416 AFIX 43 H005 2 0.492076 0.727194 0.326403 11.00000 -1.20000 AFIX 0 C006 1 0.285032 0.737096 0.499071 11.00000 0.06808 0.04930 = 0.03380 -0.00274 0.00625 -0.00506 C007 1 0.485472 0.655743 0.470677 11.00000 0.05899 0.09428 = 0.10657 0.00283 0.00642 -0.01992 AFIX 43 H007 2 0.468490 0.632708 0.539011 11.00000 -1.20000 AFIX 0 C008 1 0.416739 0.679580 0.497969 11.00000 0.05337 0.11025 = 0.04491 -0.01218 -0.00323 -0.00023 HKLF 4 REM bp2-another_a.res in Fdd2 REM wR2 = 0.3280, GooF = S = 1.261, Restrained GooF = 1.206 for all data REM R1 = 0.1339 for 484 Fo > 4sig(Fo) and 0.1519 for all 622 data REM 74 parameters refined using 52 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 0.140, deepest hole -0.150, 1-sigma level 0.044 Q1 1 0.5150 0.7182 0.2502 11.00000 0.05 0.11 Q2 1 0.2218 0.6992 1.1400 11.00000 0.05 0.10 Q3 1 0.4043 0.7899 0.1800 11.00000 0.05 0.09 Q4 1 0.4453 0.6399 0.9442 11.00000 0.05 0.09 Q5 1 0.4950 0.6620 0.0114 11.00000 0.05 0.09 ; _shelx_res_checksum 52077 _shelx_hkl_file ; 6 -26 -2 87.55 359.23 9 11 3 46.15 53.29 11 -25 -1 114.67 177.24 7 -19 -1 240.28 85.64 10 -16 0 112.29 82.79 -3 -19 -3 61.38 82.55 0 -16 -2 74.46 59.24 3 -13 -1 328.78 51.15 11 -9 1 437.26 78.51 7 -3 1 293.33 26.41 -6 10 0 693.72 53.53 5 17 3 118.95 60.19 -2 20 2 122.28 76.60 -12 20 0 134.65 131.32 -9 23 1 226.48 132.27 1 -25 -3 70.18 143.69 4 -22 -2 224.58 107.77 12 -18 0 160.82 117.29 8 -12 0 78.03 60.66 4 10 2 187.70 28.31 -13 13 -1 29.74 90.40 -10 16 0 129.89 85.41 1 23 3 49.96 99.44 -6 26 2 145.12 141.08 6 -24 -2 53.05 123.71 9 -21 -1 324.74 118.95 -1 -21 -3 56.38 88.02 2 -18 -2 187.94 71.85 5 -15 -1 86.83 60.19 13 -11 1 90.64 84.69 -5 -15 -3 43.54 47.58 4 -6 0 187.23 27.83 -9 -9 -3 29.02 16.18 12 -2 2 64.71 35.21 -10 0 -2 47.58 21.17 -7 3 -1 173.19 26.88 -4 6 0 221.49 28.79 -11 9 -1 318.55 66.37 0 16 2 48.77 58.05 -4 22 2 151.78 96.83 -11 25 1 102.06 159.39 8 -26 -2 -30.45 112.77 11 -23 -1 52.81 105.87 10 -14 0 38.30 61.38 -2 -12 -2 81.60 38.30 1 -9 -1 184.61 32.59 -1 9 1 219.82 30.45 -8 12 0 86.36 60.66 3 19 3 43.06 68.28 -12 18 0 97.30 87.55 -9 21 1 229.57 89.21 -1 25 3 101.35 115.86 -6 24 2 6.42 92.78 1 -23 -3 27.60 84.69 4 -20 -2 6.90 61.14 12 -16 0 88.26 67.33 7 -17 -1 57.33 58.29 9 -5 1 66.14 36.16 -6 -6 -2 168.67 12.85 7 13 3 15.23 29.98 2 12 2 68.99 34.26 -10 14 0 31.64 56.38 -2 18 2 211.97 60.19 1 21 3 42.11 69.71 -11 23 1 -21.65 87.55 8 -24 -2 93.50 76.60 11 -21 -1 75.18 71.13 6 -22 -2 152.02 67.56 14 -18 0 41.39 68.04 9 -19 -1 190.80 65.19 -3 -17 -3 39.02 50.44 0 -14 -2 256.70 44.25 3 -11 -1 241.23 35.21 11 -7 1 65.19 41.63 6 -8 0 430.84 37.83 -6 8 0 494.12 37.59 -13 11 -1 38.54 64.95 -4 20 2 31.17 54.96 -1 -19 -3 35.69 51.86 2 -16 -2 153.92 45.91 5 -13 -1 262.88 42.35 13 -9 1 74.46 48.77 8 -10 0 136.32 37.35 -3 -3 -1 839.08 20.22 -12 2 -2 83.98 33.54 -9 5 -1 85.88 32.12 5 15 3 17.84 38.54 0 14 2 221.49 38.30 -12 16 0 60.66 61.14 -9 19 1 125.85 58.52 -1 23 3 24.74 60.19 -6 22 2 148.21 62.33 3 -23 -3 44.96 63.76 1 -21 -3 63.76 56.38 4 -18 -2 174.86 49.72 12 -14 0 126.09 55.91 7 -15 -1 128.47 47.10 10 -12 0 260.74 45.68 -7 -11 -3 27.12 29.26 -8 10 0 113.24 36.40 3 17 3 42.58 42.11 -2 16 2 169.15 47.34 -14 18 0 12.61 64.95 -11 21 1 82.31 62.81 8 -22 -2 31.64 64.47 11 -19 -1 72.80 59.95 6 -20 -2 133.70 58.52 14 -16 0 3.81 61.14 9 -17 -1 137.51 54.96 -11 7 -1 64.95 39.02 -10 12 0 286.43 49.72 1 19 3 31.88 48.29 -4 18 2 165.82 50.91 -5 -13 -3 139.41 36.40 -4 -8 -2 324.50 26.17 -13 9 -1 65.66 48.29 -12 14 0 71.37 49.96 -9 17 1 117.52 53.77 -1 21 3 61.14 54.24 -6 20 2 104.91 56.62 -11 19 1 32.12 59.00 -3 23 3 15.23 56.38 3 -21 -3 112.05 63.28 1 -19 -3 125.14 54.48 -1 -17 -3 94.45 47.34 -3 -15 -3 146.79 42.58 0 -12 -2 241.95 36.87 -2 -10 -2 681.35 37.11 12 0 2 46.63 29.98 10 2 2 57.57 19.75 -14 16 0 0.71 59.71 10 -22 -2 31.88 68.52 13 -19 -1 69.47 65.42 8 -20 -2 102.30 63.04 11 -17 -1 104.20 58.29 6 -18 -2 163.20 56.86 14 -14 0 42.11 54.72 9 -15 -1 96.83 51.86 4 -16 -2 164.87 48.29 12 -12 0 47.58 48.29 7 -13 -1 147.97 46.15 2 -14 -2 369.94 46.87 15 -9 1 12.61 49.96 10 -10 0 99.68 45.20 5 -11 -1 404.67 42.35 13 -7 1 134.18 44.49 8 -8 0 245.99 39.02 11 -5 1 92.78 39.02 6 -6 0 223.39 30.45 1 -7 -1 656.61 31.17 9 -3 1 100.16 29.02 1 5 1 1168.81 34.26 4 -4 0 357.33 23.55 7 -1 1 141.55 21.65 6 6 2 152.49 14.99 -4 4 0 389.44 23.79 -1 7 1 650.18 32.12 -6 6 0 231.72 29.26 2 10 2 538.85 35.21 -8 8 0 282.86 37.35 5 13 3 154.87 36.87 3 15 3 197.46 44.49 -2 14 2 238.85 44.73 1 17 3 118.47 47.34 -4 16 2 228.39 48.06 -9 15 1 114.91 51.15 -1 19 3 75.41 56.86 -6 18 2 153.92 54.48 -11 17 1 75.18 57.10 -3 21 3 73.51 55.43 10 -20 -2 21.41 63.76 5 -21 -3 106.58 59.95 -11 5 -1 59.95 33.54 7 11 3 72.56 29.50 -13 7 -1 165.82 41.16 -10 10 0 74.46 43.30 -15 9 -1 13.32 52.10 -12 12 0 33.07 49.96 -14 14 0 -5.23 57.33 -13 19 1 15.94 68.99 13 -17 -1 -0.24 56.14 8 -18 -2 103.73 53.77 3 -19 -3 14.27 54.96 11 -15 -1 25.93 48.53 6 -16 -2 260.98 48.06 1 -17 -3 29.02 48.77 14 -12 0 34.97 49.25 -1 -15 -3 25.46 41.63 -7 1 -1 151.78 18.56 -9 3 -1 113.48 26.17 9 9 3 40.44 18.56 9 -13 -1 126.09 39.73 4 -14 -2 63.52 34.02 12 -10 0 200.55 38.54 7 -11 -1 148.45 32.35 -3 -13 -3 4.76 32.12 15 -7 1 53.53 40.68 -6 16 2 149.64 38.78 -11 15 1 27.12 44.96 -3 19 3 36.64 44.96 -13 17 1 14.75 51.15 -5 21 3 67.09 50.20 10 -18 -2 32.35 47.10 5 -19 -3 117.05 45.20 2 -12 -2 127.99 29.50 10 -8 0 58.05 30.21 -5 -11 -3 174.86 26.41 13 -5 1 132.75 32.35 -5 -1 -1 271.92 9.99 -12 0 -2 4.28 22.84 -4 14 2 38.06 29.74 -9 13 1 95.16 34.50 -14 12 0 45.44 40.68 -1 17 3 23.31 38.78 13 -15 -1 55.91 46.87 8 -16 -2 130.37 39.25 3 -17 -3 39.97 34.50 0 -10 -2 958.51 34.97 8 -6 0 383.50 24.98 -10 8 0 43.30 25.22 -2 12 2 117.05 26.17 -12 10 0 198.41 35.69 1 15 3 37.11 33.78 7 -19 -3 97.54 47.58 11 -13 -1 54.24 37.35 6 -14 -2 65.90 30.21 1 -15 -3 46.87 32.59 14 -10 0 28.31 36.64 -7 -9 -3 53.53 18.79 11 -3 1 48.29 21.17 -8 6 0 366.13 23.31 0 10 2 798.16 30.21 -15 7 -1 48.29 35.21 3 13 3 76.84 25.69 -13 15 1 34.73 38.78 -5 19 3 71.13 38.30 10 -16 -2 48.77 38.78 5 -17 -3 57.57 39.73 9 -11 -1 28.79 25.93 4 -12 -2 219.82 25.69 -1 -13 -3 71.13 27.83 12 -8 0 379.21 33.07 -2 -8 -2 425.84 20.22 -10 -2 -2 35.21 13.08 -13 5 -1 163.91 27.60 -11 13 1 67.09 31.88 -3 17 3 49.25 34.73 13 -13 -1 25.22 37.35 8 -14 -2 116.57 34.02 7 -9 -1 99.44 21.65 15 -5 1 40.92 31.40 6 -4 0 238.62 15.70 -6 4 0 222.20 14.75 -11 3 -1 55.91 19.75 2 8 2 414.90 18.79 5 11 3 147.50 21.41 -4 12 2 208.64 25.22 -9 11 1 20.46 25.69 -14 10 0 29.98 34.97 -1 15 3 39.25 29.26 -7 19 3 98.25 44.73 12 -16 -2 64.47 47.10 7 -17 -3 148.21 48.77 3 -15 -3 191.03 35.45 11 -11 -1 94.45 32.12 2 -10 -2 686.35 28.55 -3 -11 -3 107.06 23.08 10 -6 0 40.44 22.12 9 -1 1 23.08 13.80 -7 9 1 94.45 20.22 -12 8 0 327.83 32.35 1 13 3 156.06 30.21 -13 13 1 104.68 39.49 -5 17 3 61.14 37.35 10 -14 -2 213.16 42.11 6 -12 -2 133.22 28.31 1 -13 -3 80.89 29.02 14 -8 0 141.79 37.11 13 -3 1 160.58 29.26 12 2 2 63.52 17.13 -1 5 1 1294.18 32.12 -15 5 -1 45.44 36.16 -11 11 1 102.06 33.07 -3 15 3 40.21 35.45 -12 16 2 103.96 50.67 5 -15 -3 144.17 39.97 13 -11 -1 91.12 40.68 9 -9 -1 321.17 30.21 -4 -6 -2 254.08 13.80 -9 -7 -3 4.76 9.04 -9 1 -1 25.46 14.51 -10 6 0 44.96 21.89 -7 17 3 224.34 48.77 12 -14 -2 63.04 51.86 7 -15 -3 8.33 51.86 8 -12 -2 30.93 34.50 4 -10 -2 249.80 25.93 12 -6 0 421.32 35.45 0 -8 -2 88.98 17.84 8 -4 0 232.43 19.75 4 -2 0 84.22 8.80 7 9 3 20.70 19.03 3 11 3 42.82 25.46 -9 9 1 361.13 31.88 -14 8 0 189.37 40.21 -1 13 3 68.28 34.73 -13 11 1 69.47 46.87 -5 15 3 132.04 46.15 10 -12 -2 139.41 40.44 3 -13 -3 31.64 36.40 11 -9 -1 537.90 41.39 -1 -11 -3 15.70 28.79 7 -7 -1 341.86 25.93 -5 -9 -3 145.12 23.31 15 -3 1 82.55 38.78 -4 2 0 89.93 9.28 -8 4 0 287.86 20.94 -13 3 -1 225.53 31.40 0 8 2 124.42 18.08 -12 6 0 515.53 37.11 -4 10 2 209.35 26.17 -12 14 2 70.66 54.24 5 -13 -3 245.99 47.34 13 -9 -1 54.24 46.87 6 -10 -2 112.53 29.98 14 -6 0 6.66 39.49 11 -1 1 36.16 20.70 4 6 2 339.25 15.70 -7 7 1 324.74 25.93 -11 9 1 493.17 41.63 -3 13 3 49.01 38.30 -7 15 3 1.90 48.53 12 -12 -2 23.31 51.86 1 -11 -3 164.39 35.21 9 -7 -1 22.84 29.50 2 -8 -2 385.88 24.50 10 -4 0 23.55 23.08 -15 3 -1 55.91 39.25 1 11 3 80.17 28.79 7 -13 -3 47.58 46.63 15 -9 -1 2.14 56.86 8 -10 -2 111.81 35.69 -3 -9 -3 62.57 24.98 13 -1 1 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458.91 639.96 -2 26 0 157.25 633.77 -2 28 0 318.79 885.95 -11 -25 1 83.50 583.57 -11 -23 1 11.42 607.36 -11 -21 1 72.56 623.54 -13 7 1 484.37 300.23 11 15 -1 -1.67 849.07 11 17 -1 0.00 849.07 11 19 -1 182.47 847.64 11 21 -1 140.84 839.55 -2 30 0 1073.65 855.02 -2 32 0 446.07 781.74 -2 34 0 305.70 864.30 -13 1 1 113.48 598.08 -13 3 1 177.24 524.10 -13 5 1 614.98 475.57 11 23 -1 -19.51 777.22 11 25 -1 161.54 907.83 -2 36 0 72.08 811.72 -2 38 0 51.39 779.60 -13 -19 1 0.00 814.34 -13 -17 1 -84.46 831.70 -13 -15 1 -124.66 827.18 -13 -13 1 -44.49 933.76 -13 -11 1 109.91 899.51 -13 -9 1 -240.04 873.34 -13 -7 1 134.18 833.61 -13 -5 1 -6.66 773.66 -13 -3 1 252.89 698.24 -13 -1 1 -153.21 637.81 0 -38 0 -27.83 996.09 0 -36 0 109.20 1038.68 0 -34 0 -88.98 1079.36 0 -32 0 34.73 1080.31 0 -30 0 -233.62 1089.11 0 -28 0 -24.50 1085.54 0 -26 0 -259.07 1083.88 0 -24 0 -8.80 1047.72 0 -22 0 -132.27 990.15 0 -20 0 284.05 947.09 0 -18 0 -94.45 902.84 0 -16 0 286.43 844.31 0 -14 0 -56.14 771.28 0 -12 0 802.20 701.57 0 -10 0 123.71 605.22 13 -1 -1 223.15 850.02 13 1 -1 50.67 922.58 13 3 -1 369.70 903.31 13 5 -1 238.85 1013.46 13 7 -1 385.88 1043.44 13 9 -1 116.33 1149.30 13 11 -1 347.57 1221.86 13 13 -1 221.96 1273.96 13 15 -1 29.26 1128.13 13 17 -1 212.21 1161.91 13 19 -1 0.00 1174.04 0 10 0 209.83 613.31 0 12 0 2809.14 733.93 0 14 0 -287.15 804.34 0 16 0 1307.51 886.90 0 18 0 431.08 936.38 0 20 0 711.33 997.05 0 22 0 314.74 1055.09 0 24 0 256.22 1096.96 0 26 0 10.94 1131.94 0 28 0 141.08 1178.09 0 30 0 -220.06 1220.67 0 32 0 135.60 1205.68 0 34 0 32.35 1240.89 0 36 0 240.04 1440.49 0 38 0 102.54 1397.91 13 -9 -1 15.70 709.42 13 -7 -1 88.26 749.15 13 -5 -1 220.53 788.41 13 -3 -1 229.34 762.24 -2 -38 0 -189.13 1509.01 -2 -36 0 49.48 1489.98 -2 -34 0 -32.59 1492.12 -15 -9 1 168.91 1299.42 -15 -7 1 -204.36 1220.91 13 -11 -1 -178.43 731.07 -2 -32 0 376.60 1684.58 -2 -30 0 473.42 1689.10 -2 -28 0 -266.69 1636.52 -2 -26 0 -157.97 1565.15 -15 -5 1 240.04 1384.35 -15 -3 1 -393.73 1289.19 -15 -1 1 11.18 1382.68 -15 1 1 -366.13 1199.50 -2 -24 0 97.06 1744.53 -2 -22 0 -147.50 1688.15 -2 -20 0 371.36 1541.60 2 28 0 657.08 1932.47 2 30 0 898.32 2034.06 2 32 0 355.19 2050.71 2 34 0 707.52 2131.36 2 36 0 -3.81 2157.77 2 38 0 27.36 2207.25 -15 3 1 -368.03 1203.07 -15 5 1 -173.67 1284.43 -15 7 1 163.68 1337.48 15 5 -1 -626.16 2305.03 15 7 -1 -285.48 2474.65 15 9 -1 -79.22 2006.94 -4 -36 0 393.25 2407.33 -4 -34 0 524.10 2973.29 -4 -32 0 -13.80 2904.54 -4 -30 0 239.09 2109.47 -2 -18 0 1574.91 1842.07 -2 -16 0 909.97 1309.41 2 20 0 818.86 2060.23 2 22 0 95.87 2186.08 2 24 0 223.15 2289.56 2 26 0 -270.26 2389.01 -15 9 1 -503.64 1223.53 15 1 -1 82.79 1920.10 15 3 -1 -136.56 1947.46 -6 -36 0 521.72 2609.54 -4 -28 0 996.09 2354.04 -4 -26 0 922.58 2249.60 -2 -14 0 1317.74 1346.05 2 18 0 1222.10 1602.27 4 34 0 -281.68 2413.75 4 36 0 -34.73 2832.22 15 -3 -1 123.00 1286.33 15 -1 -1 63.04 1715.27 -6 -34 0 204.12 2642.37 -6 -32 0 -999.90 2526.51 -4 -24 0 281.44 1977.91 -4 -22 0 419.90 1838.50 -2 -12 0 0.00 926.15 4 26 0 403.96 1686.01 4 28 0 739.40 2227.71 4 30 0 709.42 2267.68 4 32 0 -366.61 2309.07 15 -5 -1 36.64 1034.63 -6 -30 0 187.94 1992.19 -6 -28 0 72.08 1840.64 -4 -20 0 364.23 1295.37 4 24 0 0.00 1320.59 6 34 0 -257.65 1556.35 6 36 0 407.53 2213.44 15 -7 -1 29.02 501.73 -8 -32 0 -108.96 1351.76 -8 -30 0 42.58 942.57 -6 -26 0 142.27 1209.02 -6 -24 0 130.13 978.96 -4 -18 0 44.96 831.23 -4 -16 0 1249.22 455.34 6 32 0 -158.44 1319.88 -8 -28 0 0.00 733.93 -6 -22 0 -33.54 542.65 9 -29 -1 19.51 263.59 11 -23 -1 686.82 548.13 15 -9 -1 -48.77 296.19 -10 -30 0 1.67 575.01 -8 -26 0 18.32 522.67 -8 -24 0 41.16 396.82 -6 -20 0 93.73 400.63 -6 -18 0 196.27 229.57 7 -33 -1 4.76 209.35 -10 -28 0 -54.24 394.68 -10 -26 0 166.29 351.14 -8 -22 0 177.95 265.02 -6 -16 0 126.33 190.08 9 -27 -1 35.92 118.47 -10 -24 0 893.08 265.02 -8 -20 0 401.34 198.89 -6 -14 0 108.72 100.87 10 28 0 72.32 277.87 5 -35 -1 56.62 163.68 7 -31 -1 9.28 139.17 -12 -24 0 12.85 211.97 -10 -22 0 81.60 183.90 -10 -20 0 58.76 132.99 -8 -18 0 69.47 138.22 6 14 0 8.33 87.31 8 20 0 287.62 147.26 10 24 0 603.08 160.82 10 26 0 80.41 200.08 3 -37 -1 53.05 169.86 5 -33 -1 47.10 121.33 7 -29 -1 116.10 102.06 9 -25 -1 126.80 70.89 -12 -22 0 50.67 163.20 -10 -18 0 76.60 125.14 -8 -16 0 139.41 103.25 -6 -12 0 403.01 83.27 -4 -8 0 665.41 56.86 8 18 0 49.96 113.00 10 22 0 62.09 145.83 -7 33 1 26.64 108.25 3 -35 -1 49.96 129.18 5 -31 -1 55.43 99.68 -12 -20 0 75.18 127.52 -10 -16 0 63.28 99.92 -8 -14 0 136.08 83.50 -6 -10 0 918.30 68.75 6 12 0 288.10 65.90 8 16 0 146.79 88.50 10 20 0 16.89 113.95 12 24 0 30.93 145.83 -11 25 1 44.49 61.62 -9 29 1 -12.85 84.69 -5 35 1 8.33 99.44 1 -37 -1 70.18 132.04 3 -33 -1 76.60 90.64 7 -27 -1 29.50 65.42 -12 -18 0 72.80 104.44 -10 -14 0 60.90 81.36 -8 -12 0 11.42 66.14 -4 -6 0 231.95 35.45 6 10 0 734.88 59.48 8 14 0 113.48 71.61 10 18 0 28.31 93.26 12 20 0 98.02 93.50 12 22 0 -12.13 118.24 -9 27 1 45.20 54.48 -7 31 1 1.19 84.22 -3 37 1 11.18 104.20 -1 -37 -1 57.81 103.49 1 -35 -1 72.08 104.91 3 -31 -1 115.86 72.08 5 -29 -1 58.05 64.71 9 -23 -1 240.99 40.44 -14 -18 0 9.99 100.39 -12 -16 0 29.74 83.27 -6 -8 0 742.25 49.01 4 6 0 198.89 30.93 8 12 0 23.08 55.19 10 16 0 16.18 75.41 12 18 0 81.12 90.88 -7 29 1 26.64 64.71 -5 33 1 -15.46 79.46 -3 35 1 22.36 83.98 -3 -37 -1 21.17 97.30 -1 -35 -1 44.73 83.98 1 -33 -1 332.82 84.93 7 -25 -1 50.20 41.63 -14 -16 0 -5.23 80.17 -12 -14 0 113.72 68.75 -10 -12 0 381.59 60.19 -8 -10 0 63.04 52.81 6 8 0 570.96 41.87 10 14 0 37.83 60.66 12 16 0 -0.95 73.51 -5 31 1 0.71 62.33 -3 33 1 15.94 64.95 -1 37 1 13.80 97.54 -3 -35 -1 42.82 78.27 -1 -33 -1 237.43 68.52 1 -31 -1 82.79 58.52 3 -29 -1 508.63 63.04 5 -27 -1 40.68 44.01 -14 -14 0 -12.61 65.42 -12 -12 0 -1.90 54.96 -10 -10 0 7.61 46.39 -8 -8 0 284.29 39.97 8 10 0 68.75 39.97 10 12 0 287.86 50.91 12 14 0 79.22 61.14 14 18 0 -28.31 75.89 -11 23 1 18.79 31.17 -9 25 1 66.61 36.16 -7 27 1 3.09 41.87 -5 29 1 29.74 47.10 -3 31 1 37.11 50.20 -1 35 1 14.04 76.37 1 37 1 30.21 75.18 -5 -35 -1 19.98 72.32 -3 -33 -1 41.39 62.09 -1 -31 -1 44.49 54.96 1 -29 -1 19.27 47.58 -14 -12 0 39.25 52.81 -6 -6 0 139.17 29.50 -4 -4 0 342.82 21.89 4 4 0 335.20 19.03 6 6 0 119.90 25.22 8 8 0 219.82 33.54 14 16 0 4.28 60.66 -1 33 1 285.72 64.47 1 35 1 11.18 58.76 3 37 1 6.66 67.09 -5 -33 -1 30.21 60.90 -3 -31 -1 267.88 54.48 3 -27 -1 309.03 41.39 5 -25 -1 77.08 31.64 7 -23 -1 63.04 27.12 -14 -10 0 78.75 47.82 -12 -10 0 202.69 47.82 -10 -8 0 24.50 31.64 10 10 0 13.80 39.25 12 12 0 6.42 43.06 14 14 0 -1.19 50.20 -7 25 1 28.79 27.60 -5 27 1 42.35 33.78 -3 29 1 313.08 44.49 -1 31 1 42.82 49.72 1 33 1 120.85 52.34 3 35 1 19.03 57.81 -7 -33 -1 -0.95 59.71 -5 -31 -1 49.01 52.10 -1 -29 -1 19.03 41.16 1 -27 -1 71.37 34.73 9 -21 -1 256.70 22.12 -12 -8 0 577.39 43.54 -8 -6 0 484.61 31.17 10 8 0 18.79 29.98 12 10 0 166.29 37.83 14 12 0 31.88 44.25 -9 23 1 120.14 21.89 -3 27 1 263.12 34.50 -1 29 1 11.42 36.16 1 31 1 34.73 44.01 3 33 1 37.11 50.91 5 35 1 45.91 59.48 -7 -31 -1 11.66 53.77 -5 -29 -1 79.70 41.39 -3 -29 -1 272.87 46.63 -1 -27 -1 34.97 36.16 3 -25 -1 29.50 29.50 11 -19 -1 88.50 21.17 -14 -8 0 211.02 44.73 -10 -6 0 29.50 28.07 -6 -4 0 338.30 20.46 6 4 0 311.65 19.27 8 6 0 443.45 28.07 14 10 0 68.28 43.54 -5 25 1 41.39 27.60 1 29 1 13.32 38.06 3 31 1 180.33 47.10 5 33 1 24.50 48.29 7 33 1 -13.32 50.44 -7 -29 -1 57.33 49.48 -3 -27 -1 141.31 39.73 1 -25 -1 17.37 28.31 5 -23 -1 230.29 26.17 -12 -6 0 487.46 39.73 -8 -4 0 299.28 22.60 10 6 0 27.12 25.46 12 8 0 518.63 40.44 -7 23 1 42.58 18.56 -3 25 1 26.64 26.41 -1 27 1 38.30 34.02 3 29 1 184.85 43.30 5 31 1 6.42 48.29 7 31 1 0.00 41.63 -9 -29 -1 51.62 49.25 -7 -27 -1 14.51 45.44 -5 -27 -1 45.20 42.11 -1 -25 -1 31.17 30.93 3 -23 -1 -3.57 23.79 7 -21 -1 30.21 16.65 -14 -6 0 29.50 36.16 -10 -4 0 2.38 20.22 -4 -2 0 63.76 9.99 4 2 0 72.56 9.04 8 4 0 272.16 19.98 14 8 0 226.48 41.39 -11 21 1 115.62 14.99 -1 25 1 11.66 26.41 1 27 1 18.08 33.07 3 27 1 157.97 39.25 5 29 1 64.95 45.44 -9 -27 -1 11.18 47.58 -5 -25 -1 162.72 35.45 -3 -25 -1 16.89 29.74 1 -23 -1 37.83 21.65 -12 -4 0 305.94 29.50 12 6 0 467.48 34.73 -5 23 1 189.13 21.89 1 25 1 8.56 25.69 5 27 1 50.91 37.59 -11 -25 -1 123.47 43.54 -9 -25 -1 68.28 38.78 -7 -25 -1 63.28 34.73 -1 -23 -1 40.92 20.94 5 -21 -1 85.64 16.18 -14 -4 0 370.41 31.88 10 4 0 3.57 17.84 14 6 0 31.88 29.98 -9 21 1 364.94 15.94 -3 23 1 13.32 17.60 3 25 1 2.85 25.69 -3 -23 -1 45.91 44.25 -8 -2 0 -21.41 25.69 5 25 1 77.32 57.10 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' ; _shelx_hkl_checksum 51007 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' 'x+1/4, -y+1/4, z+1/4' '-x+1/4, y+1/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/4, -y+3/4, z+3/4' '-x+1/4, y+3/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' 'x+3/4, -y+1/4, z+3/4' '-x+3/4, y+1/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' 'x+3/4, -y+3/4, z+1/4' '-x+3/4, y+3/4, z+1/4' 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 C9 C 0.3701(8) 0.7426(5) 0.376(4) 0.060(5) Uani 1 1 d . . . . . H9 H 0.381566 0.764937 0.275357 0.072 Uiso 1 1 calc R U . . . C002 C 0.2656(9) 0.6998(5) 0.608(5) 0.061(5) Uani 1 1 d . . . . . H002 H 0.209385 0.693409 0.681143 0.073 Uiso 1 1 calc R U . . . C003 C 0.3322(9) 0.6742(5) 0.601(5) 0.065(5) Uani 1 1 d . . . . . H003 H 0.317556 0.651108 0.674504 0.078 Uiso 1 1 calc R U . . . O1 O 0.5589(11) 0.6563(6) 0.386(6) 0.094(6) Uani 1 1 d . . . . . C005 C 0.4355(11) 0.7198(7) 0.385(4) 0.072(6) Uani 1 1 d . . . . . H005 H 0.492076 0.727194 0.326403 0.086 Uiso 1 1 calc R U . . . C006 C 0.2850(8) 0.7371(5) 0.499(3) 0.050(4) Uani 1 1 d . . . . . C007 C 0.4855(11) 0.6557(6) 0.471(6) 0.087(7) Uani 1 1 d . . . . . H007 H 0.468490 0.632708 0.539011 0.104 Uiso 1 1 calc R U . . . C008 C 0.4167(9) 0.6796(6) 0.498(4) 0.070(6) 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 C9 0.064(9) 0.062(12) 0.054(10) -0.022(8) -0.011(7) -0.002(8) C002 0.053(7) 0.052(11) 0.078(13) -0.013(8) 0.012(7) -0.007(7) C003 0.060(8) 0.057(11) 0.077(12) 0.021(9) 0.010(8) -0.006(7) O1 0.080(9) 0.101(15) 0.101(16) -0.004(12) 0.001(9) 0.002(9) C005 0.086(10) 0.108(17) 0.022(7) 0.016(9) 0.025(7) 0.004(11) C006 0.068(9) 0.049(11) 0.034(9) -0.003(6) 0.006(6) -0.005(6) C007 0.059(10) 0.094(17) 0.107(16) 0.003(14) 0.006(10) -0.020(10) C008 0.053(8) 0.110(17) 0.045(10) -0.012(10) -0.003(6) 0.000(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0000 0.0000 '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' O O 0.0000 0.0000 '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 C005 C9 H9 116.4 . . C005 C9 C006 127(2) . . C006 C9 H9 116.4 . . C003 C002 H002 120.4 . . C003 C002 C006 119.3(12) . . C006 C002 H002 120.4 . . C002 C003 H003 116.7 . . C008 C003 C002 126.7(18) . . C008 C003 H003 116.7 . . C9 C005 H005 120.6 . . C9 C005 C008 118.7(15) . . C008 C005 H005 120.6 . . C9 C006 C002 114.7(14) . . C9 C006 C006 126.4(19) . 14_565 C006 C006 C002 118.6(13) 14_565 . O1 C007 H007 111.0 . . O1 C007 C008 138(2) . . C008 C007 H007 111.0 . . C003 C008 C005 112.8(15) . . C003 C008 C007 130(2) . . C007 C008 C005 116.8(15) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C9 H9 0.9300 . C9 C005 1.31(3) . C9 C006 1.39(2) . C002 H002 0.9300 . C002 C003 1.39(2) . C002 C006 1.48(3) . C003 H003 0.9300 . C003 C008 1.36(2) . O1 C007 1.16(2) . C005 H005 0.9300 . C005 C008 1.58(3) . C006 C006 1.43(3) 14_565 C007 H007 0.9300 . C007 C008 1.37(3) . 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 C9 C005 C008 C003 -5(2) . . . . C9 C005 C008 C007 173.7(17) . . . . C002 C003 C008 C005 1(3) . . . . C002 C003 C008 C007 -177(2) . . . . C003 C002 C006 C9 4(2) . . . . C003 C002 C006 C006 178.4(13) . . . 14_565 O1 C007 C008 C003 179(3) . . . . O1 C007 C008 C005 1(4) . . . . C005 C9 C006 C002 -9(2) . . . . C005 C9 C006 C006 177.3(14) . . . 14_565 C006 C9 C005 C008 9(3) . . . . C006 C002 C003 C008 -1(3) . . . .