#------------------------------------------------------------------------------ #$Date: 2026-03-04 22:02:21 +0000 (Wed, 04 Mar 2026) $ #$Revision: 304784 $ #$URL: svn://www.crystallography.net/cod/cif/7/06/43/7064315.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_7064315 loop_ _publ_author_name 'Tran, Vy-Phuong' 'Kundu, Arup' 'Scott, Madelyn N.' 'Iwanicki, Ainsley' 'Nalaoh, Phattananawee' 'Diers, James R.' 'Taniguchi, Masahiko' 'Bocian, David F.' 'Schlau-Cohen, Gabriela S.' 'Lindsey, Jonathan S.' _publ_section_title ; Synthesis and characterization of 5,15-bis(hydroxymethyl)porphyrins -- simple compounds distantly inspired by the chlorosomal bacteriochlorophylls ; _journal_issue 4 _journal_name_full 'New Journal of Chemistry' _journal_page_first 1990 _journal_page_last 2004 _journal_paper_doi 10.1039/D5NJ04118J _journal_volume 50 _journal_year 2026 _chemical_formula_moiety 'C44 H44 N4 O2 Zn' _chemical_formula_sum 'C44 H44 N4 O2 Zn' _chemical_formula_weight 726.20 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2025-09-10 _audit_creation_method ; Olex2 1.5 (compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314) ; _audit_update_record ; 2025-10-17 deposited with the CCDC. 2025-12-29 downloaded from the CCDC. ; _cell_angle_alpha 106.040(6) _cell_angle_beta 105.616(5) _cell_angle_gamma 106.667(6) _cell_formula_units_Z 1 _cell_length_a 8.2431(15) _cell_length_b 10.460(2) _cell_length_c 11.845(2) _cell_measurement_reflns_used 9879 _cell_measurement_temperature 100.00 _cell_measurement_theta_max 28.32 _cell_measurement_theta_min 2.72 _cell_volume 870.4(3) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 100.00 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0513 _diffrn_reflns_av_unetI/netI 0.0438 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 16179 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.484 _diffrn_reflns_theta_min 2.306 _diffrn_source_current 1.4 _diffrn_source_power 0.07 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.751 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6476 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1438 before and 0.0949 after correction. The Ratio of minimum to maximum transmission is 0.8684. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear dark violet' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary violet _exptl_crystal_density_diffrn 1.385 _exptl_crystal_description block _exptl_crystal_F_000 382 _exptl_crystal_size_max 0.552 _exptl_crystal_size_mid 0.301 _exptl_crystal_size_min 0.108 _refine_diff_density_max 0.645 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.124 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 233 _refine_ls_number_reflns 3998 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.067 _refine_ls_R_factor_all 0.0353 _refine_ls_R_factor_gt 0.0345 _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^)+(0.0377P)^2^+0.4615P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0852 _refine_ls_wR_factor_ref 0.0858 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3870 _reflns_number_total 3998 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d5nj04118j2.cif _cod_data_source_block ncsu_pn99_a _cod_original_sg_symbol_H-M P-1 _cod_database_code 7064315 _shelx_shelxl_version_number 2019/1 _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 0.923 _shelx_estimated_absorpt_t_min 0.682 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14) 2.c Idealised Me refined as rotating group: C18(H18A,H18B,H18C) ; _shelx_res_file ; TITL NCSU_PN99_a.res in P-1 ncsu_pn99_a.res created by SHELXL-2019/1 at 18:19:03 on 10-Sep-2025 REM Old TITL NCSU_PN99 in P-1 REM SHELXT solution in P-1: R1 0.081, Rweak 0.011, Alpha 0.045 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C44 N4 O2 Zn CELL 0.71073 8.2431 10.4598 11.8452 106.04 105.616 106.667 ZERR 1 0.0015 0.002 0.002 0.006 0.005 0.006 LATT 1 SFAC C H N O Zn UNIT 44 44 4 2 1 L.S. 10 PLAN 5 SIZE 0.108 0.301 0.552 TEMP -173.15 CONF BOND fmap 2 MORE -1 BOND $H ACTA list 4 REM REM REM WGHT 0.037700 0.461500 FVAR 0.50703 C1 1 0.261113 0.252672 0.756264 11.00000 0.01436 0.01623 = 0.01513 0.00877 0.00617 0.00658 C2 1 0.167350 0.103084 0.704804 11.00000 0.02266 0.01632 = 0.01945 0.00722 0.00973 0.00718 AFIX 43 H2 2 0.149174 0.049067 0.620262 11.00000 -1.20000 AFIX 0 C3 1 0.100211 0.032289 0.776201 11.00000 0.02848 0.01735 = 0.03222 0.01429 0.01491 0.00555 AFIX 43 H3 2 0.036300 -0.069685 0.740382 11.00000 -1.20000 AFIX 0 C4 1 0.126606 0.110707 0.899936 11.00000 0.03418 0.03040 = 0.03133 0.02215 0.02023 0.01284 AFIX 43 H4 2 0.081913 0.062056 0.948943 11.00000 -1.20000 AFIX 0 C5 1 0.217815 0.259510 0.952080 11.00000 0.03078 0.02879 = 0.01887 0.01251 0.01371 0.01477 AFIX 43 H5 2 0.234124 0.313108 1.036270 11.00000 -1.20000 AFIX 0 C6 1 0.285491 0.330259 0.880752 11.00000 0.02092 0.01724 = 0.01617 0.00746 0.00655 0.00825 AFIX 43 H6 2 0.348909 0.432288 0.916910 11.00000 -1.20000 AFIX 0 C7 1 0.334040 0.329051 0.679488 11.00000 0.01622 0.01230 = 0.01257 0.00551 0.00657 0.00501 C8 1 0.525026 0.389654 0.716361 11.00000 0.01609 0.01193 = 0.01220 0.00517 0.00467 0.00508 C9 1 0.800069 0.498568 0.720419 11.00000 0.01442 0.01238 = 0.01139 0.00393 0.00289 0.00611 C10 1 0.822783 0.437816 0.816759 11.00000 0.01716 0.01925 = 0.01469 0.00825 0.00390 0.00815 AFIX 43 H10 2 0.935016 0.443509 0.871336 11.00000 -1.20000 AFIX 0 C11 1 0.653730 0.371217 0.814502 11.00000 0.01926 0.01727 = 0.01472 0.00937 0.00598 0.00750 AFIX 43 H11 2 0.625289 0.321826 0.867377 11.00000 -1.20000 AFIX 0 C12 1 0.205013 0.331423 0.575503 11.00000 0.01418 0.01098 = 0.01338 0.00408 0.00607 0.00394 C13 1 0.009519 0.272468 0.542430 11.00000 0.01440 0.01458 = 0.01697 0.00610 0.00726 0.00381 AFIX 43 H13 2 -0.053191 0.223727 0.584453 11.00000 -1.20000 AFIX 0 C14 1 -0.067524 0.299910 0.439977 11.00000 0.01193 0.01676 = 0.01671 0.00519 0.00490 0.00369 AFIX 43 H14 2 -0.194384 0.274582 0.397089 11.00000 -1.20000 AFIX 0 C15 1 0.079622 0.374906 0.408336 11.00000 0.01231 0.01068 = 0.01327 0.00238 0.00375 0.00429 C16 1 0.056222 0.424996 0.308424 11.00000 0.01293 0.01210 = 0.01223 0.00251 0.00260 0.00538 C17 1 -0.137248 0.394715 0.225573 11.00000 0.01278 0.01938 = 0.01717 0.00800 0.00308 0.00665 AFIX 23 H17A 2 -0.137459 0.479015 0.202984 11.00000 -1.20000 H17B 2 -0.216715 0.382443 0.274573 11.00000 -1.20000 AFIX 0 C18 1 -0.216717 0.259703 0.103731 11.00000 0.02057 0.02344 = 0.01752 0.00461 -0.00079 0.00476 AFIX 137 H18A 2 -0.342068 0.244244 0.054684 11.00000 -1.50000 H18B 2 -0.217521 0.175680 0.125385 11.00000 -1.50000 H18C 2 -0.141468 0.272699 0.053072 11.00000 -1.50000 AFIX 0 C19 1 0.542855 0.846344 0.574101 11.00000 0.03343 0.01909 = 0.02530 0.01020 0.01298 0.01150 AFIX 23 H19A 2 0.436417 0.826101 0.498648 11.00000 -1.20000 H19B 2 0.650126 0.854244 0.549780 11.00000 -1.20000 AFIX 0 C20 1 0.581893 0.985549 0.681007 11.00000 0.04672 0.01906 = 0.03830 0.00727 0.01806 0.01432 AFIX 23 H20A 2 0.479120 1.017443 0.662248 11.00000 -1.20000 H20B 2 0.695154 1.063536 0.693616 11.00000 -1.20000 AFIX 0 C21 1 0.604017 0.947296 0.797938 11.00000 0.03993 0.02678 = 0.02503 -0.00047 0.01048 0.01151 AFIX 23 H21A 2 0.717816 1.018600 0.869946 11.00000 -1.20000 H21B 2 0.498597 0.943601 0.823725 11.00000 -1.20000 AFIX 0 C22 1 0.612450 0.798881 0.755278 11.00000 0.02149 0.02429 = 0.01688 0.00414 0.00439 0.00583 AFIX 23 H22A 2 0.740247 0.807721 0.771659 11.00000 -1.20000 H22B 2 0.560980 0.741392 0.800373 11.00000 -1.20000 AFIX 0 N1 3 0.617408 0.467441 0.661016 11.00000 0.01253 0.01317 = 0.01244 0.00539 0.00383 0.00403 N2 3 0.244187 0.392538 0.492395 11.00000 0.01208 0.01305 = 0.01228 0.00570 0.00446 0.00403 O1 4 0.504662 0.733029 0.621945 11.00000 0.01894 0.01586 = 0.01578 0.00481 0.00405 0.00566 ZN1 5 0.500000 0.500000 0.500000 10.50000 0.01051 0.01608 = 0.01205 0.00791 0.00322 0.00360 HKLF 4 REM NCSU_PN99_a.res in P-1 REM wR2 = 0.0858, GooF = S = 1.067, Restrained GooF = 1.067 for all data REM R1 = 0.0345 for 3870 Fo > 4sig(Fo) and 0.0353 for all 3998 data REM 233 parameters refined using 0 restraints END WGHT 0.0377 0.4615 REM Highest difference peak 0.645, deepest hole -0.349, 1-sigma level 0.124 Q1 1 0.0059 0.3422 0.4185 11.00000 0.05 0.65 Q2 1 0.3003 0.2915 0.7190 11.00000 0.05 0.61 Q3 1 0.1078 0.3000 0.5660 11.00000 0.05 0.57 Q4 1 0.1668 0.4041 0.4563 11.00000 0.05 0.54 Q5 1 0.3383 0.4510 0.5190 11.00000 0.05 0.54 ; _shelx_res_checksum 69990 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 C1 C 0.26111(19) 0.25267(16) 0.75626(13) 0.0143(3) Uani 1 1 d . . . . . C2 C 0.1674(2) 0.10308(16) 0.70480(15) 0.0191(3) Uani 1 1 d . . . . . H2 H 0.149174 0.049067 0.620262 0.023 Uiso 1 1 calc R U . . . C3 C 0.1002(2) 0.03229(18) 0.77620(17) 0.0249(3) Uani 1 1 d . . . . . H3 H 0.036300 -0.069685 0.740382 0.030 Uiso 1 1 calc R U . . . C4 C 0.1266(2) 0.11071(19) 0.89994(17) 0.0277(4) Uani 1 1 d . . . . . H4 H 0.081913 0.062056 0.948943 0.033 Uiso 1 1 calc R U . . . C5 C 0.2178(2) 0.25951(19) 0.95208(15) 0.0236(3) Uani 1 1 d . . . . . H5 H 0.234124 0.313108 1.036270 0.028 Uiso 1 1 calc R U . . . C6 C 0.2855(2) 0.33026(17) 0.88075(14) 0.0178(3) Uani 1 1 d . . . . . H6 H 0.348909 0.432288 0.916910 0.021 Uiso 1 1 calc R U . . . C7 C 0.33404(19) 0.32905(15) 0.67949(13) 0.0134(3) Uani 1 1 d . . . . . C8 C 0.52503(19) 0.38965(15) 0.71636(13) 0.0135(3) Uani 1 1 d . . . . . C9 C 0.80007(19) 0.49857(15) 0.72042(13) 0.0131(3) Uani 1 1 d . . . . . C10 C 0.8228(2) 0.43782(16) 0.81676(14) 0.0169(3) Uani 1 1 d . . . . . H10 H 0.935016 0.443509 0.871336 0.020 Uiso 1 1 calc R U . . . C11 C 0.6537(2) 0.37122(16) 0.81450(13) 0.0163(3) Uani 1 1 d . . . . . H11 H 0.625289 0.321826 0.867377 0.020 Uiso 1 1 calc R U . . . C12 C 0.20501(19) 0.33142(15) 0.57550(13) 0.0130(3) Uani 1 1 d . . . . . C13 C 0.00952(19) 0.27247(15) 0.54243(14) 0.0155(3) Uani 1 1 d . . . . . H13 H -0.053191 0.223727 0.584453 0.019 Uiso 1 1 calc R U . . . C14 C -0.06752(19) 0.29991(16) 0.43998(14) 0.0160(3) Uani 1 1 d . . . . . H14 H -0.194384 0.274582 0.397089 0.019 Uiso 1 1 calc R U . . . C15 C 0.07962(18) 0.37491(15) 0.40834(13) 0.0129(3) Uani 1 1 d . . . . . C16 C 0.05622(18) 0.42500(15) 0.30842(13) 0.0133(3) Uani 1 1 d . . . . . C17 C -0.13725(19) 0.39472(16) 0.22557(14) 0.0167(3) Uani 1 1 d . . . . . H17A H -0.137459 0.479015 0.202984 0.020 Uiso 1 1 calc R U . . . H17B H -0.216715 0.382443 0.274573 0.020 Uiso 1 1 calc R U . . . C18 C -0.2167(2) 0.25970(18) 0.10373(15) 0.0240(3) Uani 1 1 d . . . . . H18A H -0.342068 0.244244 0.054684 0.036 Uiso 1 1 calc R U . . . H18B H -0.217521 0.175680 0.125385 0.036 Uiso 1 1 calc R U . . . H18C H -0.141468 0.272699 0.053072 0.036 Uiso 1 1 calc R U . . . C19 C 0.5429(2) 0.84634(18) 0.57410(16) 0.0248(3) Uani 1 1 d . . . . . H19A H 0.436417 0.826101 0.498648 0.030 Uiso 1 1 calc R U . . . H19B H 0.650126 0.854244 0.549780 0.030 Uiso 1 1 calc R U . . . C20 C 0.5819(3) 0.9855(2) 0.68101(19) 0.0348(4) Uani 1 1 d . . . . . H20A H 0.479120 1.017443 0.662248 0.042 Uiso 1 1 calc R U . . . H20B H 0.695154 1.063536 0.693616 0.042 Uiso 1 1 calc R U . . . C21 C 0.6040(3) 0.9473(2) 0.79794(17) 0.0338(4) Uani 1 1 d . . . . . H21A H 0.717816 1.018600 0.869946 0.041 Uiso 1 1 calc R U . . . H21B H 0.498597 0.943601 0.823725 0.041 Uiso 1 1 calc R U . . . C22 C 0.6125(2) 0.79888(18) 0.75528(15) 0.0232(3) Uani 1 1 d . . . . . H22A H 0.740247 0.807721 0.771659 0.028 Uiso 1 1 calc R U . . . H22B H 0.560980 0.741392 0.800373 0.028 Uiso 1 1 calc R U . . . N1 N 0.61741(16) 0.46744(13) 0.66102(11) 0.0130(2) Uani 1 1 d . . . . . N2 N 0.24419(16) 0.39254(13) 0.49240(11) 0.0125(2) Uani 1 1 d . . . . . O1 O 0.50466(14) 0.73303(11) 0.62194(10) 0.0180(2) Uani 1 1 d . . . . . Zn1 Zn 0.500000 0.500000 0.500000 0.01292(8) Uani 1 2 d S . P . . 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 0.0144(6) 0.0162(7) 0.0151(6) 0.0088(5) 0.0062(5) 0.0066(5) C2 0.0227(7) 0.0163(7) 0.0195(7) 0.0072(6) 0.0097(6) 0.0072(6) C3 0.0285(8) 0.0174(8) 0.0322(9) 0.0143(7) 0.0149(7) 0.0055(6) C4 0.0342(9) 0.0304(9) 0.0313(9) 0.0221(8) 0.0202(7) 0.0128(7) C5 0.0308(8) 0.0288(9) 0.0189(7) 0.0125(7) 0.0137(7) 0.0148(7) C6 0.0209(7) 0.0172(7) 0.0162(7) 0.0075(6) 0.0066(6) 0.0083(6) C7 0.0162(6) 0.0123(6) 0.0126(6) 0.0055(5) 0.0066(5) 0.0050(5) C8 0.0161(7) 0.0119(6) 0.0122(6) 0.0052(5) 0.0047(5) 0.0051(5) C9 0.0144(6) 0.0124(6) 0.0114(6) 0.0039(5) 0.0029(5) 0.0061(5) C10 0.0172(7) 0.0193(7) 0.0147(6) 0.0083(6) 0.0039(5) 0.0081(6) C11 0.0193(7) 0.0173(7) 0.0147(6) 0.0094(6) 0.0060(6) 0.0075(6) C12 0.0142(6) 0.0110(6) 0.0134(6) 0.0041(5) 0.0061(5) 0.0039(5) C13 0.0144(6) 0.0146(7) 0.0170(7) 0.0061(5) 0.0073(5) 0.0038(5) C14 0.0119(6) 0.0168(7) 0.0167(7) 0.0052(5) 0.0049(5) 0.0037(5) C15 0.0123(6) 0.0107(6) 0.0133(6) 0.0024(5) 0.0038(5) 0.0043(5) C16 0.0129(6) 0.0121(6) 0.0122(6) 0.0025(5) 0.0026(5) 0.0054(5) C17 0.0128(6) 0.0194(7) 0.0172(7) 0.0080(6) 0.0031(5) 0.0067(6) C18 0.0206(7) 0.0234(8) 0.0175(7) 0.0046(6) -0.0008(6) 0.0048(6) C19 0.0334(9) 0.0191(8) 0.0253(8) 0.0102(6) 0.0130(7) 0.0115(7) C20 0.0467(11) 0.0191(8) 0.0383(10) 0.0073(7) 0.0181(9) 0.0143(8) C21 0.0399(10) 0.0268(9) 0.0250(9) -0.0005(7) 0.0105(8) 0.0115(8) C22 0.0215(7) 0.0243(8) 0.0169(7) 0.0041(6) 0.0044(6) 0.0058(6) N1 0.0125(5) 0.0132(5) 0.0124(5) 0.0054(4) 0.0038(4) 0.0040(4) N2 0.0121(5) 0.0131(5) 0.0123(5) 0.0057(4) 0.0045(4) 0.0040(4) O1 0.0189(5) 0.0159(5) 0.0158(5) 0.0048(4) 0.0040(4) 0.0057(4) Zn1 0.01051(12) 0.01608(13) 0.01205(12) 0.00791(9) 0.00322(9) 0.00360(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 1.00 0.00 0.1610 0.00 0.00 -1.00 0.0730 0.00 0.00 1.00 0.1180 0.00 -1.00 0.00 0.0540 0.00 1.00 0.00 0.0210 1.00 0.00 0.00 0.2310 1.00 -1.00 0.00 0.2150 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 C2 C1 C6 118.80(14) . . ? C2 C1 C7 120.57(13) . . ? C6 C1 C7 120.63(13) . . ? C1 C2 H2 119.7 . . ? C3 C2 C1 120.53(14) . . ? C3 C2 H2 119.7 . . ? C2 C3 H3 120.0 . . ? C4 C3 C2 119.98(15) . . ? C4 C3 H3 120.0 . . ? C3 C4 H4 119.9 . . ? C5 C4 C3 120.23(15) . . ? C5 C4 H4 119.9 . . ? C4 C5 H5 120.1 . . ? C4 C5 C6 119.76(15) . . ? C6 C5 H5 120.1 . . ? C1 C6 H6 119.7 . . ? C5 C6 C1 120.68(15) . . ? C5 C6 H6 119.7 . . ? C8 C7 C1 117.20(12) . . ? C8 C7 C12 125.77(13) . . ? C12 C7 C1 117.02(12) . . ? C7 C8 C11 124.53(13) . . ? N1 C8 C7 125.81(13) . . ? N1 C8 C11 109.56(12) . . ? C16 C9 C10 124.74(13) 2_666 . ? N1 C9 C10 109.30(12) . . ? N1 C9 C16 125.95(12) . 2_666 ? C9 C10 H10 126.4 . . ? C11 C10 C9 107.15(12) . . ? C11 C10 H10 126.4 . . ? C8 C11 H11 126.5 . . ? C10 C11 C8 107.02(12) . . ? C10 C11 H11 126.5 . . ? C7 C12 C13 124.52(13) . . ? N2 C12 C7 125.77(13) . . ? N2 C12 C13 109.69(12) . . ? C12 C13 H13 126.5 . . ? C14 C13 C12 107.00(12) . . ? C14 C13 H13 126.5 . . ? C13 C14 H14 126.4 . . ? C13 C14 C15 107.14(12) . . ? C15 C14 H14 126.4 . . ? C16 C15 C14 124.66(13) . . ? N2 C15 C14 109.46(12) . . ? N2 C15 C16 125.86(13) . . ? C9 C16 C15 124.71(13) 2_666 . ? C9 C16 C17 117.30(12) 2_666 . ? C15 C16 C17 117.99(13) . . ? C16 C17 H17A 109.0 . . ? C16 C17 H17B 109.0 . . ? C16 C17 C18 112.84(12) . . ? H17A C17 H17B 107.8 . . ? C18 C17 H17A 109.0 . . ? C18 C17 H17B 109.0 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? H19A C19 H19B 108.6 . . ? C20 C19 H19A 110.4 . . ? C20 C19 H19B 110.4 . . ? O1 C19 H19A 110.4 . . ? O1 C19 H19B 110.4 . . ? O1 C19 C20 106.50(14) . . ? C19 C20 H20A 110.8 . . ? C19 C20 H20B 110.8 . . ? C19 C20 C21 104.76(15) . . ? H20A C20 H20B 108.9 . . ? C21 C20 H20A 110.8 . . ? C21 C20 H20B 110.8 . . ? C20 C21 H21A 111.0 . . ? C20 C21 H21B 111.0 . . ? H21A C21 H21B 109.0 . . ? C22 C21 C20 103.97(14) . . ? C22 C21 H21A 111.0 . . ? C22 C21 H21B 111.0 . . ? C21 C22 H22A 110.8 . . ? C21 C22 H22B 110.8 . . ? H22A C22 H22B 108.9 . . ? O1 C22 C21 104.85(13) . . ? O1 C22 H22A 110.8 . . ? O1 C22 H22B 110.8 . . ? C8 N1 C9 106.97(11) . . ? C8 N1 Zn1 125.81(9) . . ? C9 N1 Zn1 126.46(10) . . ? C12 N2 C15 106.71(11) . . ? C12 N2 Zn1 126.20(9) . . ? C15 N2 Zn1 126.99(10) . . ? C19 O1 Zn1 117.70(9) . . ? C22 O1 C19 106.05(12) . . ? C22 O1 Zn1 118.34(9) . . ? N1 Zn1 N1 180.0 . 2_666 ? N1 Zn1 O1 87.10(4) . 2_666 ? N1 Zn1 O1 92.90(4) 2_666 2_666 ? N1 Zn1 O1 92.90(4) . . ? N1 Zn1 O1 87.10(4) 2_666 . ? N2 Zn1 N1 89.54(5) . 2_666 ? N2 Zn1 N1 90.46(5) . . ? N2 Zn1 N1 89.54(5) 2_666 . ? N2 Zn1 N1 90.46(5) 2_666 2_666 ? N2 Zn1 N2 180.0 2_666 . ? N2 Zn1 O1 88.47(4) 2_666 . ? N2 Zn1 O1 91.53(4) 2_666 2_666 ? N2 Zn1 O1 88.47(4) . 2_666 ? N2 Zn1 O1 91.53(4) . . ? O1 Zn1 O1 180.0 . 2_666 ? 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 C1 C2 1.394(2) . ? C1 C6 1.400(2) . ? C1 C7 1.4990(19) . ? C2 H2 0.9500 . ? C2 C3 1.390(2) . ? C3 H3 0.9500 . ? C3 C4 1.389(2) . ? C4 H4 0.9500 . ? C4 C5 1.384(2) . ? C5 H5 0.9500 . ? C5 C6 1.391(2) . ? C6 H6 0.9500 . ? C7 C8 1.405(2) . ? C7 C12 1.4056(19) . ? C8 C11 1.4462(19) . ? C8 N1 1.3711(18) . ? C9 C10 1.4474(19) . ? C9 C16 1.409(2) 2_666 ? C9 N1 1.3748(18) . ? C10 H10 0.9500 . ? C10 C11 1.357(2) . ? C11 H11 0.9500 . ? C12 C13 1.4447(19) . ? C12 N2 1.3720(18) . ? C13 H13 0.9500 . ? C13 C14 1.357(2) . ? C14 H14 0.9500 . ? C14 C15 1.4452(19) . ? C15 C16 1.4107(19) . ? C15 N2 1.3760(17) . ? C16 C17 1.5175(19) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C17 C18 1.530(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C19 C20 1.523(2) . ? C19 O1 1.4416(19) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C20 C21 1.524(3) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 C22 1.522(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C22 O1 1.4320(18) . ? N1 Zn1 2.0602(12) . ? N2 Zn1 2.0495(12) . ? O1 Zn1 2.4494(11) . ? 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 C1 C2 C3 C4 -0.1(3) . . . . ? C1 C7 C8 C11 6.3(2) . . . . ? C1 C7 C8 N1 -177.68(13) . . . . ? C1 C7 C12 C13 3.4(2) . . . . ? C1 C7 C12 N2 -178.36(12) . . . . ? C2 C1 C6 C5 0.1(2) . . . . ? C2 C1 C7 C8 -110.59(16) . . . . ? C2 C1 C7 C12 68.30(18) . . . . ? C2 C3 C4 C5 0.7(3) . . . . ? C3 C4 C5 C6 -1.0(3) . . . . ? C4 C5 C6 C1 0.5(2) . . . . ? C6 C1 C2 C3 -0.3(2) . . . . ? C6 C1 C7 C8 69.58(18) . . . . ? C6 C1 C7 C12 -111.53(16) . . . . ? C7 C1 C2 C3 179.82(14) . . . . ? C7 C1 C6 C5 179.97(14) . . . . ? C7 C8 C11 C10 176.26(14) . . . . ? C7 C8 N1 C9 -176.32(13) . . . . ? C7 C8 N1 Zn1 -5.8(2) . . . . ? C7 C12 C13 C14 177.88(13) . . . . ? C7 C12 N2 C15 -178.02(13) . . . . ? C7 C12 N2 Zn1 -1.5(2) . . . . ? C8 C7 C12 C13 -177.77(13) . . . . ? C8 C7 C12 N2 0.4(2) . . . . ? C9 C10 C11 C8 0.26(16) . . . . ? C9 C16 C17 C18 83.91(16) 2_666 . . . ? C10 C9 N1 C8 0.00(16) . . . . ? C10 C9 N1 Zn1 -170.41(9) . . . . ? C11 C8 N1 C9 0.17(16) . . . . ? C11 C8 N1 Zn1 170.65(9) . . . . ? C12 C7 C8 C11 -172.43(14) . . . . ? C12 C7 C8 N1 3.5(2) . . . . ? C12 C13 C14 C15 0.48(16) . . . . ? C13 C12 N2 C15 0.39(15) . . . . ? C13 C12 N2 Zn1 176.96(9) . . . . ? C13 C14 C15 C16 -178.72(13) . . . . ? C13 C14 C15 N2 -0.25(16) . . . . ? C14 C15 C16 C9 178.25(13) . . . 2_666 ? C14 C15 C16 C17 -1.8(2) . . . . ? C14 C15 N2 C12 -0.10(15) . . . . ? C14 C15 N2 Zn1 -176.63(9) . . . . ? C15 C16 C17 C18 -96.05(16) . . . . ? C16 C9 C10 C11 -179.07(14) 2_666 . . . ? C16 C9 N1 C8 178.88(13) 2_666 . . . ? C16 C9 N1 Zn1 8.5(2) 2_666 . . . ? C16 C15 N2 C12 178.34(13) . . . . ? C16 C15 N2 Zn1 1.8(2) . . . . ? C19 C20 C21 C22 10.5(2) . . . . ? C20 C19 O1 C22 -31.73(17) . . . . ? C20 C19 O1 Zn1 -166.89(11) . . . . ? C20 C21 C22 O1 -29.78(19) . . . . ? C21 C22 O1 C19 38.52(16) . . . . ? C21 C22 O1 Zn1 173.33(10) . . . . ? N1 C8 C11 C10 -0.28(17) . . . . ? N1 C9 C10 C11 -0.17(17) . . . . ? N2 C12 C13 C14 -0.56(16) . . . . ? N2 C15 C16 C9 0.0(2) . . . 2_666 ? N2 C15 C16 C17 180.00(13) . . . . ? O1 C19 C20 C21 12.1(2) . . . . ?