# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
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data_UPC-H4
_database_code_depnum_ccdc_archive 'CCDC 1885768'
loop_
_audit_author_name
_audit_author_address
'yijie Wang'
;China University of Petroleum (East China)
China
;
_audit_update_record
;
2019-11-25 deposited with the CCDC. 2019-11-29 downloaded from the CCDC.
;
_audit_creation_date 2018-12-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2018/3
_chemical_name_common ?
_chemical_name_systematic HOF
_chemical_formula_moiety 'C28 H21 N12, C3 H7 N O'
_chemical_formula_sum 'C31 H29 N13 O'
_chemical_formula_weight 599.67
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
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'
_cell_length_a 16.6866(6)
_cell_length_b 6.5849(3)
_cell_length_c 34.8753(18)
_cell_angle_alpha 90
_cell_angle_beta 94.826(4)
_cell_angle_gamma 90
_cell_volume 3818.5(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3484
_cell_measurement_temperature 150(2)
_cell_measurement_theta_max 67.4620
_cell_measurement_theta_min 5.0620
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 0.561
_exptl_absorpt_correction_T_max 67.4620
_exptl_absorpt_correction_T_min 5.0620
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details ?
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear light violet'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier light
_exptl_crystal_colour_primary violet
_exptl_crystal_density_diffrn 1.043
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description needle
_exptl_crystal_F_000 1256
_exptl_crystal_preparation ?
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.1
_exptl_crystal_size_min 0.1
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0519
_diffrn_reflns_av_unetI/netI 0.0908
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_k_max 5
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 41
_diffrn_reflns_limit_l_min -32
_diffrn_reflns_number 14102
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 67.058
_diffrn_reflns_theta_max 67.058
_diffrn_reflns_theta_min 3.521
_diffrn_ambient_temperature 150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'multiwire proportional'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_source ?
_diffrn_special_details ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3650
_reflns_number_total 6795
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement ?
_computing_data_collection ?
_computing_data_reduction ?
_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 ?
_refine_diff_density_max 0.400
_refine_diff_density_min -0.428
_refine_diff_density_rms 0.065
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.937
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 408
_refine_ls_number_reflns 6795
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1338
_refine_ls_R_factor_gt 0.0825
_refine_ls_restrained_S_all 0.937
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1342P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2108
_refine_ls_wR_factor_ref 0.2433
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H) groups, All N(H) groups, All N(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
N11(H11), C10(H10), C25(H25), C22(H22), C24(H24), C16(H16), C17(H17),
C21(H21), C11(H11A), C7(H7), C3(H3), C8(H8), C2(H2), C33(H33)
2.b X=CH2 refined with riding coordinates:
N7(H7A,H7B), N6(H6A,H6B), N2(H2A,H2B), N1(H1A,H1B)
2.c Idealised Me refined as rotating group:
C31(H31A,H31B,H31C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
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
N10 N 0.35792(18) 0.1925(4) 0.15577(9) 0.0401(8) Uani 1 1 d . . . . .
N9 N 0.47327(18) 0.0749(4) 0.19365(9) 0.0388(7) Uani 1 1 d . . . . .
N12 N 0.42922(17) -1.2011(4) -0.03108(9) 0.0357(7) Uani 1 1 d . . . . .
N8 N 0.40748(19) 0.3766(4) 0.21236(9) 0.0429(8) Uani 1 1 d . . . . .
N5 N -0.07751(19) -1.1165(5) -0.09098(11) 0.0512(9) Uani 1 1 d . . . . .
N11 N 0.39550(16) -0.8397(4) 0.01165(8) 0.0342(7) Uani 1 1 d . . . . .
H11 H 0.437598 -0.891549 0.002882 0.041 Uiso 1 1 calc R . . . .
C15 C 0.3178(2) -0.9032(5) 0.00209(11) 0.0360(8) Uani 1 1 d . . . . .
N3 N -0.17741(19) -1.3754(5) -0.10436(10) 0.0483(9) Uani 1 1 d . . . . .
N7 N 0.2960(2) 0.4833(5) 0.17437(11) 0.0531(9) Uani 1 1 d . . . . .
H7A H 0.291978 0.584813 0.189586 0.064 Uiso 1 1 calc R . . . .
H7B H 0.261926 0.468438 0.154670 0.064 Uiso 1 1 calc R . . . .
C18 C 0.3958(2) -0.6809(5) 0.03733(10) 0.0360(8) Uani 1 1 d . . . . .
C6 C 0.2066(2) -1.1060(6) -0.02920(11) 0.0384(9) Uani 1 1 d . . . . .
N6 N 0.5177(2) 0.2499(5) 0.24783(10) 0.0522(9) Uani 1 1 d . . . . .
H6A H 0.515044 0.349538 0.263608 0.063 Uiso 1 1 calc R . . . .
H6B H 0.554931 0.160061 0.251697 0.063 Uiso 1 1 calc R . . . .
C23 C 0.4265(2) -0.1085(5) 0.13622(11) 0.0362(8) Uani 1 1 d . . . . .
C5 C 0.2945(2) -1.0708(5) -0.02047(11) 0.0369(8) Uani 1 1 d . . . . .
C28 C 0.3551(2) 0.3490(5) 0.18130(11) 0.0418(9) Uani 1 1 d . . . . .
C26 C 0.4180(2) 0.0637(5) 0.16371(10) 0.0351(8) Uani 1 1 d . . . . .
N4 N -0.0601(2) -1.4448(5) -0.06276(11) 0.0514(9) Uani 1 1 d . . . . .
C10 C 0.0920(2) -1.3317(6) -0.03012(12) 0.0461(10) Uani 1 1 d . . . . .
H10 H 0.069898 -1.454261 -0.022923 0.055 Uiso 1 1 calc R . . . .
C25 C 0.4806(2) -0.4336(5) 0.12141(11) 0.0415(9) Uani 1 1 d . . . . .
H25 H 0.509019 -0.549492 0.129578 0.050 Uiso 1 1 calc R . . . .
C22 C 0.3921(2) -0.0955(5) 0.09854(11) 0.0424(9) Uani 1 1 d . . . . .
H22 H 0.360837 0.016542 0.090865 0.051 Uiso 1 1 calc R . . . .
C24 C 0.4709(2) -0.2786(5) 0.14741(11) 0.0397(9) Uani 1 1 d . . . . .
H24 H 0.494334 -0.289019 0.172489 0.048 Uiso 1 1 calc R . . . .
C16 C 0.2675(2) -0.7783(5) 0.02267(11) 0.0414(9) Uani 1 1 d . . . . .
H16 H 0.211692 -0.786215 0.021643 0.050 Uiso 1 1 calc R . . . .
N2 N -0.1578(2) -1.6826(5) -0.07549(12) 0.0612(10) Uani 1 1 d . . . . .
H2A H -0.129900 -1.765265 -0.060665 0.073 Uiso 1 1 calc R . . . .
H2B H -0.203107 -1.720863 -0.086758 0.073 Uiso 1 1 calc R . . . .
C17 C 0.3140(2) -0.6450(6) 0.04414(11) 0.0399(9) Uani 1 1 d . . . . .
H17 H 0.295700 -0.546972 0.060496 0.048 Uiso 1 1 calc R . . . .
C27 C 0.4640(2) 0.2346(5) 0.21726(11) 0.0391(9) Uani 1 1 d . . . . .
C4 C 0.3476(2) -1.2119(5) -0.03572(10) 0.0380(8) Uani 1 1 d . . . . .
C19 C 0.4638(2) -0.5855(5) 0.05524(10) 0.0363(8) Uani 1 1 d . . . . .
C1 C 0.4559(2) -1.3659(5) -0.05078(11) 0.0379(9) Uani 1 1 d . . . . .
C21 C 0.4042(2) -0.2486(5) 0.07242(11) 0.0410(9) Uani 1 1 d . . . . .
H21 H 0.382001 -0.236363 0.047159 0.049 Uiso 1 1 calc R . . . .
C20 C 0.4488(2) -0.4197(5) 0.08326(11) 0.0358(8) Uani 1 1 d . . . . .
N1 N -0.1932(2) -1.0565(6) -0.13019(12) 0.0680(12) Uani 1 1 d . . . . .
H1A H -0.238152 -1.095776 -0.141698 0.082 Uiso 1 1 calc R . . . .
H1B H -0.176848 -0.934075 -0.133081 0.082 Uiso 1 1 calc R . . . .
C11 C 0.1712(2) -1.2866(6) -0.01864(12) 0.0465(10) Uani 1 1 d . . . . .
H11A H 0.201614 -1.379236 -0.003458 0.056 Uiso 1 1 calc R . . . .
C12 C -0.0367(2) -1.2542(6) -0.06906(12) 0.0471(10) Uani 1 1 d . . . . .
C9 C 0.0453(2) -1.1949(6) -0.05234(12) 0.0441(9) Uani 1 1 d . . . . .
C7 C 0.1581(2) -0.9645(6) -0.04935(12) 0.0486(10) Uani 1 1 d . . . . .
H7 H 0.179228 -0.838776 -0.055283 0.058 Uiso 1 1 calc R . . . .
C14 C -0.1311(2) -1.4974(6) -0.08095(12) 0.0471(10) Uani 1 1 d . . . . .
C3 C 0.3220(2) -1.3896(6) -0.05830(12) 0.0493(10) Uani 1 1 d . . . . .
H3 H 0.269247 -1.429260 -0.065182 0.059 Uiso 1 1 calc R . . . .
C13 C -0.1484(2) -1.1870(6) -0.10761(13) 0.0523(11) Uani 1 1 d . . . . .
C8 C 0.0785(2) -1.0082(6) -0.06073(13) 0.0530(11) Uani 1 1 d . . . . .
H8 H 0.046752 -0.911365 -0.074166 0.064 Uiso 1 1 calc R . . . .
C2 C 0.3879(2) -1.4842(6) -0.06721(12) 0.0487(10) Uani 1 1 d . . . . .
H2 H 0.390297 -1.603649 -0.081301 0.058 Uiso 1 1 calc R . . . .
O2 O 0.2860(5) -0.1782(9) 0.2259(2) 0.182(3) Uani 1 1 d . . . . .
N13 N 0.2564(6) 0.1031(12) 0.2564(3) 0.163(3) Uani 1 1 d . . . . .
C33 C 0.2535(8) -0.0489(14) 0.2307(3) 0.151(4) Uani 1 1 d . . . . .
H33 H 0.210452 -0.033391 0.212240 0.182 Uiso 1 1 calc R . . . .
C31 C 0.3252(9) 0.134(3) 0.2869(3) 0.276(10) Uani 1 1 d . . . . .
H31A H 0.370087 0.051671 0.280943 0.414 Uiso 1 1 calc GR . . . .
H31B H 0.308503 0.094998 0.311503 0.414 Uiso 1 1 calc GR . . . .
H31C H 0.340763 0.274179 0.287514 0.414 Uiso 1 1 calc GR . . . .
C30 C 0.1993(16) 0.250(3) 0.2564(8) 0.435(17) Uani 1 1 d . . . . .
H30A H 0.224754 0.380121 0.260551 0.652 Uiso 1 1 calc GR . . . .
H30B H 0.164936 0.224081 0.276560 0.652 Uiso 1 1 calc GR . . . .
H30C H 0.167851 0.250757 0.232031 0.652 Uiso 1 1 calc GR . . . .
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
N10 0.0368(16) 0.0272(15) 0.0534(19) -0.0045(14) -0.0142(14) 0.0043(13)
N9 0.0408(17) 0.0289(15) 0.0442(18) 0.0003(13) -0.0108(14) -0.0014(13)
N12 0.0308(15) 0.0284(15) 0.0458(18) -0.0046(13) -0.0096(13) -0.0002(12)
N8 0.0433(18) 0.0301(16) 0.053(2) -0.0027(14) -0.0111(15) 0.0028(14)
N5 0.0357(17) 0.0463(19) 0.069(2) 0.0008(17) -0.0143(16) -0.0023(15)
N11 0.0270(14) 0.0303(15) 0.0435(17) -0.0004(13) -0.0075(12) 0.0020(12)
C15 0.0310(17) 0.0269(17) 0.048(2) 0.0027(16) -0.0093(15) 0.0058(15)
N3 0.0375(17) 0.0416(18) 0.063(2) -0.0061(16) -0.0096(16) -0.0006(15)
N7 0.050(2) 0.0389(18) 0.066(2) -0.0116(17) -0.0218(17) 0.0087(16)
C18 0.0371(19) 0.0280(18) 0.041(2) 0.0012(15) -0.0098(15) 0.0028(15)
C6 0.0299(18) 0.040(2) 0.043(2) -0.0041(17) -0.0107(15) 0.0033(16)
N6 0.061(2) 0.0361(18) 0.054(2) -0.0111(15) -0.0269(17) 0.0092(16)
C23 0.0363(19) 0.0216(17) 0.049(2) -0.0004(15) -0.0086(16) 0.0000(14)
C5 0.0321(18) 0.0304(18) 0.046(2) 0.0012(16) -0.0112(15) 0.0036(15)
C28 0.041(2) 0.0294(18) 0.053(2) -0.0039(17) -0.0109(17) 0.0030(16)
C26 0.0360(18) 0.0234(17) 0.044(2) 0.0036(15) -0.0080(15) 0.0004(14)
N4 0.0402(18) 0.0424(19) 0.069(2) -0.0011(17) -0.0116(16) -0.0052(15)
C10 0.035(2) 0.043(2) 0.058(3) 0.0086(19) -0.0144(18) -0.0013(17)
C25 0.040(2) 0.0310(19) 0.051(2) 0.0031(17) -0.0127(17) 0.0097(16)
C22 0.053(2) 0.0253(18) 0.046(2) 0.0020(16) -0.0148(18) 0.0071(17)
C24 0.047(2) 0.0278(18) 0.042(2) -0.0009(16) -0.0099(17) 0.0036(16)
C16 0.0292(18) 0.0347(19) 0.059(2) -0.0021(18) -0.0064(16) 0.0061(15)
N2 0.047(2) 0.047(2) 0.086(3) -0.0030(19) -0.0148(19) -0.0048(17)
C17 0.0340(19) 0.036(2) 0.048(2) -0.0046(17) -0.0079(16) 0.0046(16)
C27 0.039(2) 0.0335(19) 0.043(2) 0.0021(16) -0.0077(16) -0.0007(16)
C4 0.0361(19) 0.0353(19) 0.040(2) -0.0014(16) -0.0122(15) -0.0011(16)
C19 0.0372(19) 0.0273(17) 0.042(2) 0.0020(15) -0.0080(16) 0.0026(15)
C1 0.0370(19) 0.0273(18) 0.047(2) -0.0013(16) -0.0078(16) -0.0003(15)
C21 0.048(2) 0.0279(18) 0.044(2) 0.0004(16) -0.0115(17) 0.0065(17)
C20 0.0303(17) 0.0293(18) 0.046(2) -0.0020(16) -0.0054(15) 0.0031(14)
N1 0.055(2) 0.045(2) 0.097(3) 0.007(2) -0.037(2) -0.0077(17)
C11 0.037(2) 0.043(2) 0.057(3) 0.0082(19) -0.0101(18) 0.0008(17)
C12 0.035(2) 0.048(2) 0.055(3) 0.000(2) -0.0080(18) 0.0066(18)
C9 0.036(2) 0.040(2) 0.054(2) 0.0021(18) -0.0069(17) 0.0006(17)
C7 0.037(2) 0.041(2) 0.065(3) 0.000(2) -0.0119(18) 0.0008(17)
C14 0.037(2) 0.039(2) 0.064(3) -0.0045(19) -0.0064(19) -0.0016(17)
C3 0.034(2) 0.047(2) 0.064(3) -0.015(2) -0.0098(18) -0.0016(18)
C13 0.039(2) 0.046(2) 0.069(3) -0.002(2) -0.0142(19) 0.0000(18)
C8 0.036(2) 0.045(2) 0.074(3) 0.010(2) -0.018(2) 0.0067(18)
C2 0.041(2) 0.041(2) 0.062(3) -0.014(2) -0.0056(19) -0.0022(18)
O2 0.279(9) 0.084(4) 0.187(6) -0.059(4) 0.043(6) 0.023(5)
N13 0.202(9) 0.107(5) 0.185(8) -0.034(5) 0.056(7) 0.001(6)
C33 0.246(13) 0.089(6) 0.119(7) -0.024(6) 0.019(7) 0.002(7)
C31 0.224(15) 0.46(3) 0.138(9) -0.069(13) -0.018(9) -0.119(17)
C30 0.50(4) 0.36(3) 0.46(3) -0.07(2) 0.15(3) 0.28(3)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
N10 C28 1.365(5) . ?
N10 C26 1.325(4) . ?
N9 C26 1.336(4) . ?
N9 C27 1.352(5) . ?
N12 C4 1.360(4) . ?
N12 C1 1.378(4) . ?
N8 C28 1.346(5) . ?
N8 C27 1.329(5) . ?
N5 C12 1.335(5) . ?
N5 C13 1.355(5) . ?
N11 C15 1.377(4) . ?
N11 C18 1.377(4) . ?
C15 C5 1.392(5) . ?
C15 C16 1.413(5) . ?
N3 C14 1.343(5) . ?
N3 C13 1.340(5) . ?
N7 C28 1.331(5) . ?
C18 C17 1.424(5) . ?
C18 C19 1.398(5) . ?
C6 C5 1.490(5) . ?
C6 C11 1.391(5) . ?
C6 C7 1.386(5) . ?
N6 C27 1.338(4) . ?
C23 C26 1.499(5) . ?
C23 C22 1.392(5) . ?
C23 C24 1.381(5) . ?
C5 C4 1.418(5) . ?
N4 C12 1.338(5) . ?
N4 C14 1.341(5) . ?
C10 C11 1.381(5) . ?
C10 C9 1.385(5) . ?
C25 C24 1.384(5) . ?
C25 C20 1.394(5) . ?
C22 C21 1.385(5) . ?
C16 C17 1.355(5) . ?
N2 C14 1.318(5) . ?
C4 C3 1.454(5) . ?
C19 C1 1.399(5) 3_635 ?
C19 C20 1.500(5) . ?
C1 C2 1.453(5) . ?
C21 C20 1.385(5) . ?
N1 C13 1.348(5) . ?
C12 C9 1.494(5) . ?
C9 C8 1.389(6) . ?
C7 C8 1.384(5) . ?
C3 C2 1.324(5) . ?
O2 C33 1.031(10) . ?
N13 C33 1.340(11) . ?
N13 C31 1.511(13) . ?
N13 C30 1.360(15) . ?
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
C26 N10 C28 114.4(3) . . ?
C26 N9 C27 114.3(3) . . ?
C4 N12 C1 105.2(3) . . ?
C27 N8 C28 114.5(3) . . ?
C12 N5 C13 113.4(3) . . ?
C18 N11 C15 109.8(3) . . ?
N11 C15 C5 126.2(3) . . ?
N11 C15 C16 106.7(3) . . ?
C5 C15 C16 126.8(3) . . ?
C13 N3 C14 114.3(3) . . ?
N11 C18 C17 106.5(3) . . ?
N11 C18 C19 126.2(3) . . ?
C19 C18 C17 127.2(3) . . ?
C11 C6 C5 120.7(3) . . ?
C7 C6 C5 121.4(3) . . ?
C7 C6 C11 117.8(3) . . ?
C22 C23 C26 120.2(3) . . ?
C24 C23 C26 120.7(3) . . ?
C24 C23 C22 119.1(3) . . ?
C15 C5 C6 117.5(3) . . ?
C15 C5 C4 125.3(3) . . ?
C4 C5 C6 117.2(3) . . ?
N8 C28 N10 124.8(3) . . ?
N7 C28 N10 116.7(3) . . ?
N7 C28 N8 118.5(3) . . ?
N10 C26 N9 126.1(3) . . ?
N10 C26 C23 117.5(3) . . ?
N9 C26 C23 116.4(3) . . ?
C12 N4 C14 115.0(3) . . ?
C11 C10 C9 120.1(4) . . ?
C24 C25 C20 121.4(3) . . ?
C21 C22 C23 120.3(3) . . ?
C23 C24 C25 120.2(3) . . ?
C17 C16 C15 108.7(3) . . ?
C16 C17 C18 108.2(3) . . ?
N8 C27 N9 125.8(3) . . ?
N8 C27 N6 118.0(3) . . ?
N6 C27 N9 116.1(3) . . ?
N12 C4 C5 124.9(3) . . ?
N12 C4 C3 110.6(3) . . ?
C5 C4 C3 124.5(3) . . ?
C18 C19 C1 126.7(3) . 3_635 ?
C18 C19 C20 116.4(3) . . ?
C1 C19 C20 116.9(3) 3_635 . ?
N12 C1 C19 126.0(3) . 3_635 ?
N12 C1 C2 110.2(3) . . ?
C19 C1 C2 123.8(3) 3_635 . ?
C22 C21 C20 121.2(3) . . ?
C25 C20 C19 120.2(3) . . ?
C21 C20 C25 117.8(3) . . ?
C21 C20 C19 122.0(3) . . ?
C10 C11 C6 121.6(4) . . ?
N5 C12 N4 126.1(4) . . ?
N5 C12 C9 116.9(4) . . ?
N4 C12 C9 116.8(3) . . ?
C10 C9 C12 120.1(4) . . ?
C10 C9 C8 118.6(4) . . ?
C8 C9 C12 121.1(3) . . ?
C8 C7 C6 120.7(4) . . ?
N4 C14 N3 125.0(4) . . ?
N2 C14 N3 117.2(4) . . ?
N2 C14 N4 117.8(4) . . ?
C2 C3 C4 107.1(3) . . ?
N3 C13 N5 126.1(4) . . ?
N3 C13 N1 116.9(4) . . ?
N1 C13 N5 116.9(4) . . ?
C7 C8 C9 120.9(4) . . ?
C3 C2 C1 106.9(3) . . ?
C33 N13 C31 123.5(12) . . ?
C33 N13 C30 123.1(16) . . ?
C30 N13 C31 113.3(15) . . ?
O2 C33 N13 137.3(13) . . ?
_iucr_refine_instructions_details
;
TITL 1 in P2(1)/c
1-sr.res
created by SHELXL-2018/3 at 17:14:04 on 14-Dec-2018
CELL 1.54178 16.6866 6.5849 34.8753 90 94.826 90
ZERR 4 0.0006 0.0003 0.0018 0 0.004 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 124 116 52 4
L.S. 5
PLAN 4
TEMP -0.15
BOND
fmap 2
acta
SHEL 999 0.837
OMIT 2 1 1
OMIT -2 1 9
OMIT -2 1 7
OMIT -1 2 4
OMIT 0 0 12
OMIT 1 1 1
OMIT 3 1 2
OMIT 4 1 7
OMIT 3 1 7
OMIT 1 0 2
OMIT -3 2 7
OMIT 1 0 6
REM
REM
REM
WGHT 0.134200
FVAR 3.66459
N10 3 0.357920 0.192487 0.155765 11.00000 0.03677 0.02723 =
0.05335 -0.00449 -0.01416 0.00433
N9 3 0.473265 0.074890 0.193654 11.00000 0.04084 0.02895 =
0.04417 0.00030 -0.01081 -0.00141
N12 3 0.429216 -1.201134 -0.031079 11.00000 0.03081 0.02838 =
0.04583 -0.00464 -0.00956 -0.00023
N8 3 0.407484 0.376609 0.212363 11.00000 0.04329 0.03008 =
0.05276 -0.00268 -0.01105 0.00280
N5 3 -0.077514 -1.116490 -0.090983 11.00000 0.03565 0.04632 =
0.06854 0.00078 -0.01430 -0.00232
N11 3 0.395496 -0.839724 0.011648 11.00000 0.02702 0.03029 =
0.04353 -0.00038 -0.00750 0.00199
AFIX 43
H11 2 0.437598 -0.891549 0.002882 11.00000 -1.20000
AFIX 0
C15 1 0.317764 -0.903150 0.002089 11.00000 0.03096 0.02688 =
0.04788 0.00267 -0.00930 0.00580
N3 3 -0.177410 -1.375419 -0.104361 11.00000 0.03750 0.04157 =
0.06344 -0.00614 -0.00964 -0.00058
N7 3 0.296037 0.483254 0.174366 11.00000 0.04957 0.03887 =
0.06648 -0.01164 -0.02178 0.00867
AFIX 93
H7A 2 0.291978 0.584813 0.189586 11.00000 -1.20000
H7B 2 0.261926 0.468438 0.154670 11.00000 -1.20000
AFIX 0
C18 1 0.395758 -0.680947 0.037334 11.00000 0.03709 0.02803 =
0.04068 0.00119 -0.00982 0.00280
C6 1 0.206581 -1.106030 -0.029204 11.00000 0.02988 0.03966 =
0.04330 -0.00412 -0.01074 0.00327
N6 3 0.517715 0.249884 0.247828 11.00000 0.06093 0.03609 =
0.05413 -0.01115 -0.02690 0.00920
AFIX 93
H6A 2 0.515044 0.349538 0.263608 11.00000 -1.20000
H6B 2 0.554931 0.160061 0.251697 11.00000 -1.20000
AFIX 0
C23 1 0.426543 -0.108511 0.136220 11.00000 0.03628 0.02161 =
0.04865 -0.00044 -0.00857 0.00000
C5 1 0.294452 -1.070826 -0.020467 11.00000 0.03207 0.03044 =
0.04576 0.00122 -0.01122 0.00361
C28 1 0.355103 0.349026 0.181295 11.00000 0.04074 0.02936 =
0.05294 -0.00394 -0.01089 0.00296
C26 1 0.418026 0.063724 0.163705 11.00000 0.03597 0.02343 =
0.04402 0.00357 -0.00797 0.00035
N4 3 -0.060135 -1.444790 -0.062763 11.00000 0.04015 0.04244 =
0.06892 -0.00110 -0.01161 -0.00518
C10 1 0.091956 -1.331747 -0.030122 11.00000 0.03517 0.04253 =
0.05760 0.00860 -0.01440 -0.00128
AFIX 43
H10 2 0.069898 -1.454261 -0.022923 11.00000 -1.20000
AFIX 0
C25 1 0.480641 -0.433609 0.121414 11.00000 0.03999 0.03096 =
0.05062 0.00313 -0.01269 0.00968
AFIX 43
H25 2 0.509019 -0.549492 0.129578 11.00000 -1.20000
AFIX 0
C22 1 0.392114 -0.095506 0.098539 11.00000 0.05256 0.02525 =
0.04611 0.00196 -0.01482 0.00706
AFIX 43
H22 2 0.360837 0.016542 0.090865 11.00000 -1.20000
AFIX 0
C24 1 0.470916 -0.278598 0.147410 11.00000 0.04661 0.02778 =
0.04241 -0.00086 -0.00987 0.00361
AFIX 43
H24 2 0.494334 -0.289019 0.172489 11.00000 -1.20000
AFIX 0
C16 1 0.267476 -0.778258 0.022667 11.00000 0.02923 0.03467 =
0.05868 -0.00210 -0.00643 0.00612
AFIX 43
H16 2 0.211692 -0.786215 0.021643 11.00000 -1.20000
AFIX 0
N2 3 -0.157791 -1.682625 -0.075491 11.00000 0.04740 0.04698 =
0.08563 -0.00302 -0.01478 -0.00483
AFIX 93
H2A 2 -0.129900 -1.765265 -0.060665 11.00000 -1.20000
H2B 2 -0.203107 -1.720863 -0.086758 11.00000 -1.20000
AFIX 0
C17 1 0.314001 -0.645013 0.044136 11.00000 0.03400 0.03583 =
0.04807 -0.00462 -0.00786 0.00462
AFIX 43
H17 2 0.295700 -0.546972 0.060496 11.00000 -1.20000
AFIX 0
C27 1 0.463972 0.234590 0.217258 11.00000 0.03892 0.03351 =
0.04313 0.00206 -0.00766 -0.00072
C4 1 0.347560 -1.211895 -0.035723 11.00000 0.03611 0.03529 =
0.03995 -0.00139 -0.01219 -0.00112
C19 1 0.463816 -0.585471 0.055240 11.00000 0.03722 0.02727 =
0.04240 0.00196 -0.00801 0.00258
C1 1 0.455860 -1.365948 -0.050777 11.00000 0.03701 0.02735 =
0.04745 -0.00133 -0.00776 -0.00028
C21 1 0.404210 -0.248631 0.072417 11.00000 0.04848 0.02793 =
0.04409 0.00044 -0.01152 0.00646
AFIX 43
H21 2 0.382001 -0.236363 0.047159 11.00000 -1.20000
AFIX 0
C20 1 0.448812 -0.419744 0.083258 11.00000 0.03033 0.02927 =
0.04634 -0.00204 -0.00541 0.00307
N1 3 -0.193211 -1.056533 -0.130189 11.00000 0.05521 0.04462 =
0.09676 0.00669 -0.03719 -0.00767
AFIX 93
H1A 2 -0.238152 -1.095776 -0.141698 11.00000 -1.20000
H1B 2 -0.176848 -0.934075 -0.133081 11.00000 -1.20000
AFIX 0
C11 1 0.171176 -1.286614 -0.018635 11.00000 0.03702 0.04258 =
0.05742 0.00824 -0.01009 0.00077
AFIX 43
H11A 2 0.201614 -1.379236 -0.003458 11.00000 -1.20000
AFIX 0
C12 1 -0.036741 -1.254197 -0.069057 11.00000 0.03540 0.04849 =
0.05545 -0.00023 -0.00804 0.00662
C9 1 0.045325 -1.194867 -0.052342 11.00000 0.03621 0.04019 =
0.05400 0.00213 -0.00687 0.00062
C7 1 0.158066 -0.964473 -0.049350 11.00000 0.03683 0.04081 =
0.06537 -0.00045 -0.01191 0.00083
AFIX 43
H7 2 0.179228 -0.838776 -0.055283 11.00000 -1.20000
AFIX 0
C14 1 -0.131088 -1.497383 -0.080945 11.00000 0.03736 0.03853 =
0.06356 -0.00454 -0.00636 -0.00158
C3 1 0.321988 -1.389571 -0.058298 11.00000 0.03448 0.04712 =
0.06394 -0.01499 -0.00982 -0.00155
AFIX 43
H3 2 0.269247 -1.429260 -0.065182 11.00000 -1.20000
AFIX 0
C13 1 -0.148405 -1.187004 -0.107610 11.00000 0.03850 0.04639 =
0.06874 -0.00194 -0.01421 0.00002
C8 1 0.078466 -1.008237 -0.060727 11.00000 0.03645 0.04485 =
0.07383 0.00978 -0.01776 0.00670
AFIX 43
H8 2 0.046752 -0.911365 -0.074166 11.00000 -1.20000
AFIX 0
C2 1 0.387924 -1.484217 -0.067209 11.00000 0.04101 0.04129 =
0.06204 -0.01415 -0.00558 -0.00225
AFIX 43
H2 2 0.390297 -1.603649 -0.081301 11.00000 -1.20000
AFIX 0
O2 4 0.285973 -0.178213 0.225933 11.00000 0.27908 0.08423 =
0.18743 -0.05886 0.04259 0.02267
N13 3 0.256446 0.103060 0.256395 11.00000 0.20231 0.10731 =
0.18524 -0.03386 0.05642 0.00097
C33 1 0.253510 -0.048892 0.230739 11.00000 0.24634 0.08918 =
0.11934 -0.02422 0.01944 0.00177
AFIX 43
H33 2 0.210452 -0.033391 0.212240 11.00000 -1.20000
AFIX 0
C31 1 0.325216 0.133776 0.286865 11.00000 0.22437 0.45874 =
0.13846 -0.06867 -0.01759 -0.11915
AFIX 137
H31A 2 0.370087 0.051671 0.280943 11.00000 -1.50000
H31B 2 0.308503 0.094998 0.311503 11.00000 -1.50000
H31C 2 0.340763 0.274179 0.287514 11.00000 -1.50000
AFIX 0
C30 1 0.199294 0.250337 0.256383 11.00000 0.50161 0.36184 =
0.45890 -0.07256 0.14637 0.28163
AFIX 137
H30A 2 0.224754 0.380121 0.260551 11.00000 -1.50000
H30B 2 0.164936 0.224081 0.276560 11.00000 -1.50000
H30C 2 0.167851 0.250757 0.232031 11.00000 -1.50000
AFIX 0
HKLF 4
REM 1 in P2(1)/c
REM wR2 = 0.2433, GooF = S = 0.937, Restrained GooF = 0.937 for all data
REM R1 = 0.0825 for 3650 Fo > 4sig(Fo) and 0.1338 for all 6795 data
REM 408 parameters refined using 0 restraints
END
WGHT 0.1343 0.0000
REM Highest difference peak 0.400, deepest hole -0.428, 1-sigma level 0.065
Q1 1 0.5000 -1.0000 0.0000 10.50000 0.05 0.31
Q2 1 -0.1717 -1.6459 -0.1106 11.00000 0.05 0.30
Q3 1 0.2751 0.2944 0.3265 11.00000 0.05 0.28
Q4 1 0.2194 -0.2495 0.2435 11.00000 0.05 0.27
REM The information below was added by Olex2.
REM
REM R1 = 0.0825 for 3650 Fo > 4sig(Fo) and 0.1338 for all 14155 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 0.40, deepest hole -0.43
REM Mean Shift 0, Max Shift -0.001.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.1338
REM R1_gt = 0.0825
REM wR_ref = 0.2433
REM GOOF = 0.937
REM Shift_max = -0.001
REM Shift_mean = 0
REM Reflections_all = 14155
REM Reflections_gt = 3650
REM Parameters = n/a
REM Hole = -0.43
REM Peak = 0.40
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'
# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 1.000 -0.005 0.250 585 131 ' '
2 1.000 -0.035 0.750 585 131 ' '
_platon_squeeze_details
;
;
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# Audit and citation data items may have been added by the CCDC.
# Please retain this information to preserve the provenance of
# this file and to allow appropriate attribution of the data.
#
#######################################################################
data_UPC-H4a
_database_code_depnum_ccdc_archive 'CCDC 1885770'
loop_
_audit_author_name
_audit_author_address
'yijie Wang'
;China University of Petroleum (East China)
China
;
_audit_update_record
;
2019-11-25 deposited with the CCDC. 2019-11-29 downloaded from the CCDC.
;
_audit_creation_date 2019-11-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number 2013-2
_chemical_name_common ?
_chemical_name_systematic HOF
_chemical_formula_moiety 'C28 H21 N12, 2(C3 H7 N O), H2 O'
_chemical_formula_sum 'C34 H37 N14 O3'
_chemical_formula_weight 689.77
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_H-M_alt 'P 1 21/c 1'
_space_group_name_Hall '-P 2ybc'
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'
_cell_length_a 16.2396(6)
_cell_length_b 6.5461(2)
_cell_length_c 33.4443(11)
_cell_angle_alpha 90
_cell_angle_beta 90.790(3)
_cell_angle_gamma 90
_cell_volume 3555.0(2)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 3260
_cell_measurement_temperature 150(2)
_cell_measurement_theta_max 68.2150
_cell_measurement_theta_min 5.2790
_shelx_estimated_absorpt_T_max 0.931
_shelx_estimated_absorpt_T_min 0.714
_exptl_absorpt_coefficient_mu 0.722
_exptl_absorpt_correction_T_max 68.2150
_exptl_absorpt_correction_T_min 5.2790
_exptl_absorpt_correction_type ?
_exptl_absorpt_process_details ?
_exptl_crystal_colour 'clear light violet'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier light
_exptl_crystal_colour_primary violet
_exptl_crystal_density_diffrn 1.289
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_description needle
_exptl_crystal_F_000 1452
_exptl_crystal_preparation ?
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.1
_exptl_crystal_size_min 0.1
_exptl_special_details
;
?
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0293
_diffrn_reflns_av_unetI/netI 0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max 17
_diffrn_reflns_limit_h_min -19
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -5
_diffrn_reflns_limit_l_max 31
_diffrn_reflns_limit_l_min -40
_diffrn_reflns_number 12711
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full 67.679
_diffrn_reflns_theta_max 70.603
_diffrn_reflns_theta_min 3.768
_diffrn_ambient_temperature 150
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type 'multiwire proportional'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_source ?
_diffrn_special_details ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 4410
_reflns_number_total 6450
_reflns_special_details
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_reflns_threshold_expression 'I > 2\s(I)'
_computing_cell_refinement ?
_computing_data_collection ?
_computing_data_reduction ?
_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 'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max 0.612
_refine_diff_density_min -0.673
_refine_diff_density_rms 0.061
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.023
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 472
_refine_ls_number_reflns 6450
_refine_ls_number_restraints 4
_refine_ls_R_factor_all 0.1054
_refine_ls_R_factor_gt 0.0723
_refine_ls_restrained_S_all 1.023
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[\s^2^(Fo^2^)+(0.1111P)^2^+1.6540P]
where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1787
_refine_ls_wR_factor_ref 0.2069
_refine_special_details
;
?
;
_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. Restrained distances
H1WB-O1W
0.85 with sigma of 0.01
O1W-H1WA
0.85 with sigma of 0.01
H1WA-H1WB
1.34 with sigma of 0.01
H1WB-H6A
2.2 with sigma of 0.01
3.a Me refined with riding coordinates:
C30(H30A,H30B,H30C), C29(H29A,H29B,H29C), C33(H33A,H33B,H33C), C32(H32A,H32B,
H32C)
3.b Aromatic/amide H refined with riding coordinates:
C27(H27), C22(H22), C20(H20), C18(H18), C17(H17), C14(H14), C11(H11),
C10(H10), C7(H7), C5(H5), C2(H2A), C1(H1), C31(H31), C34(H34)
3.c X=CH2 refined with riding coordinates:
N4(H4A,H4B), N6(H6A,H6B), N5(H5A,H5B), N3(H3A,H3B)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary iterative
_atom_sites_solution_secondary ?
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
N2 N 0.39184(15) 0.3280(4) 0.48881(7) 0.0274(5) Uani 1 1 d . . . . .
N1 N 0.56604(14) 0.2982(4) 0.46823(7) 0.0286(5) Uani 1 1 d . . . . .
N8 N 0.39897(16) -0.9163(4) 0.28265(7) 0.0333(6) Uani 1 1 d . . . . .
C28 C 0.40631(17) -0.5960(4) 0.33307(8) 0.0283(6) Uani 1 1 d . . . . .
N12 N 1.16309(15) 0.1069(4) 0.38328(8) 0.0358(6) Uani 1 1 d . . . . .
N11 N 0.34293(15) -0.7238(4) 0.33681(7) 0.0312(5) Uani 1 1 d . . . . .
N10 N 0.46651(15) -0.6137(4) 0.30628(7) 0.0337(6) Uani 1 1 d . . . . .
N9 N 1.05366(16) 0.0481(4) 0.42889(8) 0.0386(6) Uani 1 1 d . . . . .
C27 C 0.45911(18) -0.2498(5) 0.35116(8) 0.0308(6) Uani 1 1 d . . . . .
H27 H 0.4842 -0.2441 0.3264 0.037 Uiso 1 1 calc R . . . .
C26 C 0.41285(17) -0.4207(4) 0.36094(8) 0.0288(6) Uani 1 1 d . . . . .
C25 C 0.34325(18) -0.8839(5) 0.31116(8) 0.0320(6) Uani 1 1 d . . . . .
N7 N 1.06529(16) 0.3707(4) 0.39719(8) 0.0393(6) Uani 1 1 d . . . . .
N4 N 1.14880(17) -0.1994(4) 0.41481(9) 0.0429(7) Uani 1 1 d . . . . .
H4A H 1.1917 -0.2423 0.4026 0.051 Uiso 1 1 calc R . . . .
H4B H 1.1234 -0.2789 0.4310 0.051 Uiso 1 1 calc R . . . .
C24 C 0.43570(17) -0.0973(4) 0.41543(8) 0.0276(6) Uani 1 1 d . . . . .
C23 C 0.53691(17) 0.1270(4) 0.44917(8) 0.0279(6) Uani 1 1 d . . . . .
C22 C 0.91291(18) 0.1812(5) 0.46813(9) 0.0370(7) Uani 1 1 d . . . . .
H22 H 0.9392 0.0636 0.4773 0.044 Uiso 1 1 calc R . . . .
N6 N 0.28186(16) -1.0171(4) 0.31507(8) 0.0389(6) Uani 1 1 d . . . . .
H6A H 0.2786 -1.1214 0.2995 0.047 Uiso 1 1 calc DR . . . .
H6B H 0.2455 -0.9989 0.3332 0.047 Uiso 1 1 calc R . . . .
C21 C 0.64978(17) 0.2929(5) 0.46341(8) 0.0289(6) Uani 1 1 d . . . . .
C20 C 0.37589(18) -0.4258(5) 0.39832(8) 0.0314(6) Uani 1 1 d . . . . .
H20 H 0.3426 -0.5357 0.4051 0.038 Uiso 1 1 calc R . . . .
C19 C 0.45847(19) -0.7765(5) 0.28152(8) 0.0321(6) Uani 1 1 d . . . . .
C18 C 0.67350(18) 0.1107(5) 0.44153(9) 0.0352(7) Uani 1 1 d . . . . .
H18 H 0.7267 0.0733 0.4346 0.042 Uiso 1 1 calc R . . . .
C17 C 0.30239(17) 0.1250(5) 0.45622(9) 0.0334(6) Uani 1 1 d . . . . .
H17 H 0.2808 0.0234 0.4397 0.040 Uiso 1 1 calc R . . . .
C16 C 0.45440(17) 0.0708(4) 0.44420(8) 0.0285(6) Uani 1 1 d . . . . .
C15 C 0.95108(18) 0.3069(5) 0.44052(10) 0.0382(7) Uani 1 1 d . . . . .
C14 C 0.46870(17) -0.0897(5) 0.37714(8) 0.0303(6) Uani 1 1 d . . . . .
H14 H 0.4976 0.0256 0.3692 0.036 Uiso 1 1 calc R . . . .
C13 C 0.31389(17) 0.3899(4) 0.49888(8) 0.0297(6) Uani 1 1 d . . . . .
C12 C 0.38758(17) 0.1682(4) 0.46257(8) 0.0289(6) Uani 1 1 d . . . . .
N5 N 0.51688(18) -0.7960(4) 0.25413(8) 0.0424(7) Uani 1 1 d . . . . .
H5A H 0.5156 -0.8971 0.2377 0.051 Uiso 1 1 calc R . . . .
H5B H 0.5559 -0.7074 0.2529 0.051 Uiso 1 1 calc R . . . .
C11 C 0.38837(19) -0.2679(5) 0.42543(8) 0.0322(6) Uani 1 1 d . . . . .
H11 H 0.3649 -0.2757 0.4506 0.039 Uiso 1 1 calc R . . . .
C10 C 0.83554(18) 0.2319(5) 0.48192(9) 0.0369(7) Uani 1 1 d . . . . .
H10 H 0.8105 0.1483 0.5007 0.044 Uiso 1 1 calc R . . . .
C9 C 1.13319(19) 0.2972(5) 0.37887(9) 0.0360(7) Uani 1 1 d . . . . .
C8 C 1.12147(19) -0.0093(5) 0.40862(9) 0.0360(7) Uani 1 1 d . . . . .
C7 C 0.25819(18) 0.2586(5) 0.47860(9) 0.0350(7) Uani 1 1 d . . . . .
H7 H 0.2011 0.2628 0.4803 0.042 Uiso 1 1 calc R . . . .
C6 C 0.79463(18) 0.4053(5) 0.46826(9) 0.0336(7) Uani 1 1 d . . . . .
C5 C 0.60502(18) 0.0077(5) 0.43325(9) 0.0341(7) Uani 1 1 d . . . . .
H5 H 0.6011 -0.1165 0.4199 0.041 Uiso 1 1 calc R . . . .
C4 C 0.70602(17) 0.4389(5) 0.47791(8) 0.0305(6) Uani 1 1 d . . . . .
C3 C 1.02926(18) 0.2394(5) 0.42144(9) 0.0364(7) Uani 1 1 d . . . . .
N3 N 1.17309(18) 0.4225(5) 0.35401(9) 0.0483(7) Uani 1 1 d . . . . .
H3A H 1.2159 0.3799 0.3417 0.058 Uiso 1 1 calc R . . . .
H3B H 1.1558 0.5454 0.3504 0.058 Uiso 1 1 calc R . . . .
C2 C 0.8361(2) 0.5366(6) 0.44290(12) 0.0499(9) Uani 1 1 d . . . . .
H2A H 0.8114 0.6586 0.4350 0.060 Uiso 1 1 calc R . . . .
C1 C 0.9137(2) 0.4885(6) 0.42920(12) 0.0512(9) Uani 1 1 d . . . . .
H1 H 0.9409 0.5784 0.4123 0.061 Uiso 1 1 calc R . . . .
O1 O 1.0914(2) 0.7670(6) 0.30942(11) 0.0813(10) Uani 1 1 d . . . . .
O1W O 0.2239(4) -1.3596(6) 0.26317(14) 0.1098(15) Uani 1 1 d D . . . .
N13 N 1.0051(3) 1.0354(9) 0.31109(17) 0.1007(17) Uani 1 1 d . . . . .
C31 C 1.0648(7) 0.9316(17) 0.3045(4) 0.252(9) Uani 1 1 d . . . . .
H31 H 1.1031 1.0093 0.2907 0.302 Uiso 1 1 calc R . . . .
C30 C 0.9847(11) 1.2270(17) 0.3006(4) 0.310(11) Uani 1 1 d . . . . .
H30A H 0.9317 1.2600 0.3112 0.465 Uiso 1 1 calc R . . . .
H30B H 0.9827 1.2377 0.2720 0.465 Uiso 1 1 calc R . . . .
H30C H 1.0251 1.3202 0.3112 0.465 Uiso 1 1 calc R . . . .
C29 C 0.9460(7) 0.931(3) 0.3358(3) 0.262(9) Uani 1 1 d . . . . .
H29A H 0.8997 1.0189 0.3402 0.393 Uiso 1 1 calc R . . . .
H29B H 0.9713 0.8963 0.3610 0.393 Uiso 1 1 calc R . . . .
H29C H 0.9277 0.8088 0.3225 0.393 Uiso 1 1 calc R . . . .
N14 N 0.2859(3) -1.8978(15) 0.1817(2) 0.136(3) Uani 1 1 d . . . . .
O2 O 0.2095(7) -1.7316(12) 0.2268(3) 0.266(6) Uani 1 1 d . . . . .
C34 C 0.2388(6) -1.8863(14) 0.2126(3) 0.133(3) Uani 1 1 d . . . . .
H34 H 0.2261 -2.0086 0.2253 0.159 Uiso 1 1 calc R . . . .
C33 C 0.3198(6) -2.075(3) 0.1667(4) 0.264(10) Uani 1 1 d . . . . .
H33A H 0.3524 -2.0428 0.1438 0.396 Uiso 1 1 calc R . . . .
H33B H 0.2765 -2.1674 0.1590 0.396 Uiso 1 1 calc R . . . .
H33C H 0.3540 -2.1374 0.1868 0.396 Uiso 1 1 calc R . . . .
C32 C 0.3101(7) -1.706(3) 0.1659(7) 0.408(17) Uani 1 1 d . . . . .
H32A H 0.3447 -1.7278 0.1432 0.612 Uiso 1 1 calc R . . . .
H32B H 0.3399 -1.6308 0.1860 0.612 Uiso 1 1 calc R . . . .
H32C H 0.2621 -1.6308 0.1577 0.612 Uiso 1 1 calc R . . . .
H2 H 0.4321(19) 0.390(4) 0.4964(8) 0.017(7) Uiso 1 1 d . . . . .
H1WA H 0.211(3) -1.486(3) 0.2594(14) 0.073(15) Uiso 1 1 d D . . . .
H1WB H 0.272(2) -1.355(9) 0.2525(17) 0.24(6) Uiso 1 1 d 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
N2 0.0199(11) 0.0290(13) 0.0334(11) -0.0045(10) 0.0068(9) -0.0023(10)
N1 0.0262(12) 0.0261(12) 0.0337(11) -0.0037(10) 0.0096(9) -0.0010(10)
N8 0.0378(14) 0.0290(13) 0.0333(12) -0.0039(10) 0.0116(10) -0.0001(11)
C28 0.0302(14) 0.0280(15) 0.0271(12) 0.0010(11) 0.0106(10) 0.0004(12)
N12 0.0310(13) 0.0347(15) 0.0419(13) -0.0046(11) 0.0099(10) 0.0020(11)
N11 0.0327(13) 0.0295(13) 0.0316(11) -0.0044(10) 0.0108(9) 0.0004(10)
N10 0.0359(13) 0.0326(14) 0.0331(12) -0.0001(11) 0.0161(10) -0.0002(11)
N9 0.0318(13) 0.0351(15) 0.0491(14) 0.0002(12) 0.0126(11) 0.0040(12)
C27 0.0321(15) 0.0322(16) 0.0284(12) 0.0033(12) 0.0088(11) 0.0016(12)
C26 0.0284(14) 0.0277(15) 0.0305(13) -0.0021(12) 0.0050(11) 0.0024(11)
C25 0.0326(15) 0.0305(16) 0.0333(13) 0.0012(12) 0.0082(11) -0.0006(12)
N7 0.0305(13) 0.0335(14) 0.0542(15) -0.0001(12) 0.0159(11) 0.0065(11)
N4 0.0404(15) 0.0328(15) 0.0559(16) -0.0035(13) 0.0134(12) 0.0041(12)
C24 0.0273(14) 0.0242(14) 0.0315(13) -0.0023(11) 0.0042(10) 0.0031(11)
C23 0.0270(14) 0.0276(14) 0.0292(12) -0.0012(11) 0.0072(10) 0.0029(11)
C22 0.0254(14) 0.0382(18) 0.0475(16) 0.0041(14) 0.0074(12) 0.0033(13)
N6 0.0388(14) 0.0357(15) 0.0428(13) -0.0112(12) 0.0160(11) -0.0065(12)
C21 0.0228(13) 0.0328(15) 0.0313(13) -0.0023(12) 0.0089(10) 0.0020(12)
C20 0.0349(15) 0.0261(15) 0.0337(13) -0.0004(12) 0.0121(11) -0.0009(12)
C19 0.0387(16) 0.0267(15) 0.0311(13) -0.0002(12) 0.0134(11) 0.0010(12)
C18 0.0267(14) 0.0372(17) 0.0419(15) -0.0079(13) 0.0088(12) 0.0064(13)
C17 0.0275(14) 0.0302(16) 0.0427(15) -0.0056(13) 0.0052(12) -0.0053(12)
C16 0.0287(14) 0.0251(14) 0.0319(13) 0.0013(11) 0.0088(11) 0.0001(11)
C15 0.0248(15) 0.0386(18) 0.0517(17) 0.0012(15) 0.0120(13) 0.0001(13)
C14 0.0299(14) 0.0295(15) 0.0316(13) 0.0038(12) 0.0073(11) -0.0022(12)
C13 0.0245(13) 0.0296(15) 0.0354(13) 0.0008(12) 0.0108(11) -0.0011(12)
C12 0.0295(14) 0.0263(15) 0.0310(13) 0.0003(11) 0.0093(11) -0.0019(12)
N5 0.0500(17) 0.0339(15) 0.0442(14) -0.0089(12) 0.0262(12) -0.0064(13)
C11 0.0365(15) 0.0319(16) 0.0284(13) -0.0013(12) 0.0102(11) 0.0012(13)
C10 0.0274(15) 0.0432(18) 0.0405(15) 0.0040(14) 0.0120(12) -0.0006(13)
C9 0.0311(15) 0.0355(17) 0.0417(15) -0.0044(13) 0.0086(12) 0.0011(13)
C8 0.0308(15) 0.0353(17) 0.0420(15) -0.0047(13) 0.0057(12) 0.0015(13)
C7 0.0259(14) 0.0318(16) 0.0477(16) -0.0026(13) 0.0097(12) -0.0035(12)
C6 0.0258(14) 0.0336(16) 0.0417(15) -0.0075(13) 0.0132(11) 0.0016(12)
C5 0.0302(15) 0.0332(16) 0.0390(14) -0.0090(13) 0.0069(12) 0.0054(13)
C4 0.0247(14) 0.0321(16) 0.0350(13) -0.0012(12) 0.0123(11) -0.0012(12)
C3 0.0274(15) 0.0370(18) 0.0450(16) -0.0013(14) 0.0091(12) 0.0016(13)
N3 0.0467(17) 0.0386(16) 0.0603(17) 0.0052(14) 0.0257(14) 0.0087(13)
C2 0.0370(18) 0.0355(18) 0.078(2) 0.0117(17) 0.0253(17) 0.0096(15)
C1 0.0383(18) 0.0382(19) 0.078(2) 0.0147(18) 0.0313(17) 0.0047(15)
O1 0.087(2) 0.067(2) 0.090(2) 0.0069(18) -0.0023(19) 0.0153(19)
O1W 0.160(5) 0.079(3) 0.091(3) -0.019(2) 0.024(3) -0.049(3)
N13 0.092(3) 0.093(4) 0.116(4) -0.030(3) -0.053(3) 0.026(3)
C31 0.251(12) 0.200(10) 0.297(14) -0.171(10) -0.217(12) 0.161(10)
C30 0.48(2) 0.137(8) 0.302(15) -0.027(10) -0.322(17) 0.038(12)
C29 0.173(10) 0.49(3) 0.125(7) -0.041(12) 0.003(7) -0.174(14)
N14 0.068(3) 0.215(8) 0.124(5) 0.081(5) -0.004(3) -0.015(4)
O2 0.344(12) 0.163(6) 0.287(10) -0.134(7) -0.160(9) 0.139(8)
C34 0.188(9) 0.105(6) 0.103(5) -0.004(5) -0.030(6) 0.000(6)
C33 0.120(8) 0.42(2) 0.252(14) -0.177(16) -0.058(8) 0.122(11)
C32 0.097(7) 0.45(3) 0.67(4) 0.43(3) 0.059(14) -0.009(12)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
N2 C13 1.375(4) . ?
N2 C12 1.367(4) . ?
N1 C23 1.370(4) . ?
N1 C21 1.372(4) . ?
N8 C25 1.340(4) . ?
N8 C19 1.332(4) . ?
C28 N11 1.334(4) . ?
C28 N10 1.340(3) . ?
C28 C26 1.481(4) . ?
N12 C9 1.345(4) . ?
N12 C8 1.330(4) . ?
N11 C25 1.354(4) . ?
N10 C19 1.355(4) . ?
N9 C8 1.354(4) . ?
N9 C3 1.336(4) . ?
C27 C26 1.389(4) . ?
C27 C14 1.369(4) . ?
C26 C20 1.395(4) . ?
C25 N6 1.333(4) . ?
N7 C9 1.357(4) . ?
N7 C3 1.324(4) . ?
N4 C8 1.337(4) . ?
C24 C16 1.491(4) . ?
C24 C14 1.396(4) . ?
C24 C11 1.399(4) . ?
C23 C16 1.397(4) . ?
C23 C5 1.461(4) . ?
C22 C15 1.389(4) . ?
C22 C10 1.385(4) . ?
C21 C18 1.454(4) . ?
C21 C4 1.404(4) . ?
C20 C11 1.388(4) . ?
C19 N5 1.334(4) . ?
C18 C5 1.326(4) . ?
C17 C12 1.425(4) . ?
C17 C7 1.362(4) . ?
C16 C12 1.407(4) . ?
C15 C3 1.496(4) . ?
C15 C1 1.386(5) . ?
C13 C7 1.414(4) . ?
C13 C4 1.404(4) 3_666 ?
C10 C6 1.390(5) . ?
C9 N3 1.341(4) . ?
C6 C4 1.495(4) . ?
C6 C2 1.388(4) . ?
C4 C13 1.404(4) 3_666 ?
C2 C1 1.383(4) . ?
O1 C31 1.171(10) . ?
N13 C31 1.208(10) . ?
N13 C30 1.342(11) . ?
N13 C29 1.446(11) . ?
N14 C34 1.299(10) . ?
N14 C33 1.380(13) . ?
N14 C32 1.418(14) . ?
O2 C34 1.217(10) . ?
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
C12 N2 C13 110.1(2) . . ?
C23 N1 C21 105.1(2) . . ?
C19 N8 C25 114.1(3) . . ?
N11 C28 N10 125.4(3) . . ?
N11 C28 C26 118.4(2) . . ?
N10 C28 C26 116.2(3) . . ?
C8 N12 C9 114.4(3) . . ?
C28 N11 C25 114.6(2) . . ?
C28 N10 C19 114.3(3) . . ?
C3 N9 C8 114.1(3) . . ?
C14 C27 C26 121.6(3) . . ?
C27 C26 C28 120.7(2) . . ?
C27 C26 C20 118.1(3) . . ?
C20 C26 C28 121.2(3) . . ?
N8 C25 N11 125.6(3) . . ?
N6 C25 N8 118.6(3) . . ?
N6 C25 N11 115.8(2) . . ?
C3 N7 C9 114.5(3) . . ?
C14 C24 C16 119.2(3) . . ?
C14 C24 C11 117.8(3) . . ?
C11 C24 C16 122.9(2) . . ?
N1 C23 C16 126.5(2) . . ?
N1 C23 C5 110.4(2) . . ?
C16 C23 C5 123.1(3) . . ?
C10 C22 C15 119.7(3) . . ?
N1 C21 C18 110.5(3) . . ?
N1 C21 C4 125.7(3) . . ?
C4 C21 C18 123.8(3) . . ?
C11 C20 C26 120.5(3) . . ?
N8 C19 N10 125.9(3) . . ?
N8 C19 N5 118.5(3) . . ?
N5 C19 N10 115.6(3) . . ?
C5 C18 C21 107.1(3) . . ?
C7 C17 C12 108.0(3) . . ?
C23 C16 C24 117.2(2) . . ?
C23 C16 C12 124.9(3) . . ?
C12 C16 C24 117.7(2) . . ?
C22 C15 C3 119.9(3) . . ?
C1 C15 C22 119.5(3) . . ?
C1 C15 C3 120.5(3) . . ?
C27 C14 C24 120.9(3) . . ?
N2 C13 C7 106.8(3) . . ?
N2 C13 C4 126.2(3) . 3_666 ?
C4 C13 C7 126.9(3) 3_666 . ?
N2 C12 C17 106.7(2) . . ?
N2 C12 C16 126.5(3) . . ?
C16 C12 C17 126.7(3) . . ?
C20 C11 C24 120.9(2) . . ?
C22 C10 C6 121.2(3) . . ?
N12 C9 N7 125.0(3) . . ?
N3 C9 N12 117.2(3) . . ?
N3 C9 N7 117.8(3) . . ?
N12 C8 N9 125.8(3) . . ?
N12 C8 N4 117.4(3) . . ?
N4 C8 N9 116.8(3) . . ?
C17 C7 C13 108.4(3) . . ?
C10 C6 C4 120.4(3) . . ?
C2 C6 C10 118.2(3) . . ?
C2 C6 C4 121.2(3) . . ?
C18 C5 C23 106.8(3) . . ?
C21 C4 C6 116.7(3) . . ?
C13 C4 C21 125.5(3) 3_666 . ?
C13 C4 C6 117.8(3) 3_666 . ?
N9 C3 C15 116.7(3) . . ?
N7 C3 N9 126.2(3) . . ?
N7 C3 C15 117.0(3) . . ?
C1 C2 C6 120.9(3) . . ?
C2 C1 C15 120.2(3) . . ?
C31 N13 C30 132.4(14) . . ?
C31 N13 C29 112.3(11) . . ?
C30 N13 C29 115.3(12) . . ?
O1 C31 N13 141.9(16) . . ?
C34 N14 C33 125.5(10) . . ?
C34 N14 C32 114.6(13) . . ?
C33 N14 C32 119.5(12) . . ?
O2 C34 N14 126.6(11) . . ?
_shelx_res_file
;
TITL 1 in P2(1)/c
CELL 1.54178 16.2396 6.5461 33.4443 90 90.79 90
ZERR 4 0.0006 0.0002 0.0011 0 0.003 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 136 148 56 12
DFIX 0.85 0.01 H1Wb O1W
DFIX 0.85 0.01 O1W H1Wa
DFIX 1.34 0.01 H1Wa H1Wb
DFIX 2.2 0.01 H1Wb H6a
L.S. 4
PLAN 20
SIZE 0.1 0.5 0.1
TEMP -0.15
BOND
fmap 2
acta
OMIT -2 0 6
OMIT 0 0 10
OMIT -1 2 3
OMIT -1 0 8
OMIT 1 1 9
OMIT 0 1 1
OMIT 3 1 4
OMIT -6 0 6
OMIT -3 2 7
OMIT -1 1 8
OMIT -7 1 6
OMIT -2 0 2
OMIT 4 3 0
OMIT 6 1 10
OMIT 6 0 6
OMIT 5 0 2
OMIT -3 0 12
OMIT 7 1 0
OMIT 3 4 6
OMIT -9 0 14
OMIT -10 1 21
OMIT -4 0 14
OMIT -7 2 6
OMIT 5 0 6
OMIT -18 3 1
OMIT 0 1 11
OMIT -5 3 7
OMIT -7 2 1
OMIT 6 7 11
OMIT 1 2 8
OMIT -11 3 12
OMIT 3 2 5
OMIT -7 4 9
OMIT -2 2 9
OMIT -5 1 3
OMIT 6 6 6
OMIT -1 0 18
OMIT -7 1 22
OMIT -4 2 7
OMIT -6 1 8
OMIT 4 1 39
OMIT -1 4 18
OMIT -7 2 10
OMIT 5 1 13
OMIT -3 1 7
OMIT -6 2 8
OMIT -2 4 12
OMIT 3 2 22
OMIT -13 1 13
OMIT -2 7 16
OMIT 4 1 14
OMIT -2 2 3
OMIT 2 0 2
OMIT -3 0 14
OMIT 10 1 0
OMIT -6 1 26
OMIT -2 1 14
OMIT -3 2 6
OMIT 2 2 6
OMIT 2 3 19
OMIT -6 2 10
OMIT -11 2 18
OMIT 1 0 2
OMIT 4 7 12
OMIT 8 2 23
OMIT 6 2 11
OMIT 1 1 3
OMIT 1 4 2
OMIT -4 4 9
OMIT 14 1 1
OMIT -9 0 18
OMIT -1 3 17
OMIT 5 0 8
OMIT 7 6 6
OMIT 1 3 9
OMIT -4 2 4
OMIT -3 2 11
OMIT -2 4 10
OMIT 4 2 5
OMIT -9 5 4
OMIT 0 1 3
OMIT 1 2 31
OMIT -8 2 7
OMIT -1 2 14
OMIT 2 1 7
OMIT 1 1 1
OMIT 2 0 4
OMIT 4 3 10
OMIT 9 5 17
OMIT 1 1 0
OMIT 0 0 12
OMIT 16 3 17
OMIT 13 3 15
OMIT 8 1 2
OMIT 6 0 10
OMIT 11 4 24
OMIT 5 7 15
OMIT -15 2 10
OMIT -15 2 5
OMIT -2 3 15
OMIT -2 3 9
OMIT -4 6 16
OMIT 7 4 7
OMIT 3 2 7
OMIT -4 2 10
OMIT -6 5 4
OMIT -1 3 26
OMIT -12 0 12
OMIT 7 1 1
OMIT -9 2 20
OMIT 8 6 8
OMIT 2 0 18
OMIT -1 1 2
OMIT 14 2 3
OMIT -3 2 17
OMIT -12 0 10
OMIT -1 2 1
OMIT -1 3 13
OMIT -6 1 1
OMIT 4 0 14
OMIT -6 1 27
OMIT 6 7 12
OMIT -5 5 14
OMIT -10 1 20
OMIT -4 5 20
OMIT 10 2 11
OMIT 4 3 34
OMIT 9 0 18
OMIT 2 5 6
OMIT -4 3 5
OMIT 5 1 9
OMIT 5 4 0
OMIT -5 2 30
OMIT 6 0 0
OMIT 2 1 2
OMIT -1 5 19
OMIT -13 3 10
OMIT -10 2 4
OMIT 5 3 2
OMIT 1 2 1
OMIT 0 6 24
OMIT 0 3 3
OMIT 1 5 0
OMIT -4 3 7
OMIT 7 1 20
OMIT -2 7 13
OMIT 9 3 9
OMIT 15 4 12
OMIT 18 0 10
OMIT -16 3 6
OMIT 8 1 16
OMIT 18 3 0
OMIT 4 7 8
OMIT -5 0 4
OMIT 4 3 11
OMIT -10 1 18
OMIT 1 2 5
OMIT -12 0 8
OMIT 2 3 8
OMIT 3 0 10
OMIT -6 3 5
OMIT 4 2 3
OMIT 8 3 3
OMIT 5 0 4
OMIT -5 1 17
OMIT -9 1 21
OMIT 1 4 18
OMIT -6 0 24
OMIT -9 3 13
OMIT 3 2 0
OMIT 3 2 3
OMIT -3 1 11
OMIT -4 4 7
OMIT -4 0 22
OMIT 7 3 3
OMIT -12 0 24
OMIT -5 3 9
OMIT 1 0 16
OMIT 11 2 1
OMIT -5 3 5
OMIT 3 1 17
OMIT -3 1 24
OMIT 7 1 37
OMIT -14 3 5
OMIT -2 7 19
OMIT -3 3 15
OMIT 6 0 16
OMIT -3 1 3
OMIT 5 2 32
OMIT -2 3 28
OMIT -4 0 16
OMIT -5 4 5
OMIT -14 0 2
OMIT 14 1 0
OMIT -9 1 27
OMIT -9 0 16
OMIT 15 4 0
OMIT 10 4 10
OMIT -2 6 25
OMIT -1 7 14
OMIT -4 1 13
OMIT -3 4 2
OMIT 15 2 10
OMIT 4 2 1
OMIT -18 0 12
OMIT 3 1 8
OMIT 7 3 14
OMIT -6 3 2
REM
REM
REM
WGHT 0.111100 1.654000
FVAR 0.10914
N2 3 0.391836 0.328033 0.488806 11.00000 0.01992 0.02898 =
0.03342 -0.00455 0.00682 -0.00225
N1 3 0.566042 0.298214 0.468235 11.00000 0.02623 0.02609 =
0.03368 -0.00368 0.00957 -0.00101
N8 3 0.398965 -0.916314 0.282653 11.00000 0.03777 0.02898 =
0.03335 -0.00385 0.01160 -0.00009
C28 1 0.406311 -0.596020 0.333074 11.00000 0.03015 0.02796 =
0.02710 0.00099 0.01057 0.00039
N12 3 1.163087 0.106870 0.383283 11.00000 0.03100 0.03470 =
0.04188 -0.00456 0.00993 0.00198
N11 3 0.342932 -0.723845 0.336808 11.00000 0.03271 0.02947 =
0.03162 -0.00442 0.01079 0.00038
N10 3 0.466507 -0.613742 0.306278 11.00000 0.03590 0.03262 =
0.03312 -0.00006 0.01608 -0.00021
N9 3 1.053664 0.048056 0.428893 11.00000 0.03182 0.03510 =
0.04908 0.00023 0.01256 0.00402
C27 1 0.459105 -0.249846 0.351161 11.00000 0.03214 0.03223 =
0.02837 0.00330 0.00877 0.00164
AFIX 43
H27 2 0.484178 -0.244075 0.326353 11.00000 -1.20000
AFIX 0
C26 1 0.412850 -0.420694 0.360938 11.00000 0.02836 0.02766 =
0.03049 -0.00214 0.00501 0.00242
C25 1 0.343252 -0.883868 0.311161 11.00000 0.03257 0.03050 =
0.03326 0.00115 0.00818 -0.00061
N7 3 1.065293 0.370727 0.397190 11.00000 0.03054 0.03346 =
0.05418 -0.00014 0.01595 0.00651
N4 3 1.148801 -0.199409 0.414806 11.00000 0.04037 0.03279 =
0.05586 -0.00346 0.01336 0.00410
AFIX 93
H4A 2 1.191748 -0.242262 0.402600 11.00000 -1.20000
H4B 2 1.123439 -0.278898 0.430993 11.00000 -1.20000
AFIX 0
C24 1 0.435695 -0.097346 0.415427 11.00000 0.02726 0.02417 =
0.03147 -0.00226 0.00418 0.00306
C23 1 0.536906 0.127027 0.449174 11.00000 0.02699 0.02755 =
0.02920 -0.00123 0.00723 0.00291
C22 1 0.912911 0.181172 0.468133 11.00000 0.02543 0.03823 =
0.04753 0.00415 0.00745 0.00334
AFIX 43
H22 2 0.939181 0.063598 0.477307 11.00000 -1.20000
AFIX 0
N6 3 0.281863 -1.017145 0.315069 11.00000 0.03875 0.03570 =
0.04282 -0.01118 0.01603 -0.00646
AFIX 93
H6A 2 0.278590 -1.121372 0.299474 11.00000 -1.20000
H6B 2 0.245517 -0.998931 0.333186 11.00000 -1.20000
AFIX 0
C21 1 0.649783 0.292858 0.463412 11.00000 0.02281 0.03276 =
0.03131 -0.00230 0.00892 0.00203
C20 1 0.375889 -0.425783 0.398320 11.00000 0.03488 0.02606 =
0.03371 -0.00041 0.01210 -0.00091
AFIX 43
H20 2 0.342642 -0.535744 0.405130 11.00000 -1.20000
AFIX 0
C19 1 0.458474 -0.776487 0.281517 11.00000 0.03869 0.02671 =
0.03113 -0.00021 0.01335 0.00100
C18 1 0.673501 0.110650 0.441526 11.00000 0.02675 0.03715 =
0.04193 -0.00790 0.00878 0.00643
AFIX 43
H18 2 0.726703 0.073307 0.434630 11.00000 -1.20000
AFIX 0
C17 1 0.302391 0.124955 0.456224 11.00000 0.02751 0.03024 =
0.04273 -0.00559 0.00519 -0.00527
AFIX 43
H17 2 0.280782 0.023366 0.439715 11.00000 -1.20000
AFIX 0
C16 1 0.454395 0.070808 0.444200 11.00000 0.02870 0.02515 =
0.03194 0.00126 0.00883 0.00014
C15 1 0.951082 0.306856 0.440525 11.00000 0.02477 0.03861 =
0.05165 0.00121 0.01197 0.00007
C14 1 0.468705 -0.089724 0.377138 11.00000 0.02991 0.02954 =
0.03164 0.00377 0.00729 -0.00218
AFIX 43
H14 2 0.497596 0.025644 0.369172 11.00000 -1.20000
AFIX 0
C13 1 0.313889 0.389868 0.498878 11.00000 0.02447 0.02960 =
0.03540 0.00081 0.01077 -0.00111
C12 1 0.387579 0.168231 0.462567 11.00000 0.02950 0.02633 =
0.03100 0.00031 0.00929 -0.00188
N5 3 0.516883 -0.795966 0.254126 11.00000 0.04997 0.03390 =
0.04416 -0.00886 0.02621 -0.00639
AFIX 93
H5A 2 0.515554 -0.897106 0.237719 11.00000 -1.20000
H5B 2 0.555871 -0.707386 0.252874 11.00000 -1.20000
AFIX 0
C11 1 0.388374 -0.267933 0.425425 11.00000 0.03646 0.03192 =
0.02844 -0.00127 0.01018 0.00119
AFIX 43
H11 2 0.364943 -0.275673 0.450597 11.00000 -1.20000
AFIX 0
C10 1 0.835537 0.231855 0.481924 11.00000 0.02737 0.04318 =
0.04049 0.00402 0.01197 -0.00059
AFIX 43
H10 2 0.810489 0.148272 0.500670 11.00000 -1.20000
AFIX 0
C9 1 1.133185 0.297197 0.378866 11.00000 0.03108 0.03554 =
0.04165 -0.00435 0.00863 0.00109
C8 1 1.121472 -0.009272 0.408619 11.00000 0.03080 0.03530 =
0.04199 -0.00468 0.00570 0.00149
C7 1 0.258190 0.258611 0.478604 11.00000 0.02592 0.03178 =
0.04766 -0.00265 0.00972 -0.00346
AFIX 43
H7 2 0.201097 0.262809 0.480265 11.00000 -1.20000
AFIX 0
C6 1 0.794634 0.405350 0.468262 11.00000 0.02582 0.03364 =
0.04165 -0.00749 0.01317 0.00159
C5 1 0.605025 0.007724 0.433245 11.00000 0.03022 0.03322 =
0.03895 -0.00896 0.00686 0.00536
AFIX 43
H5 2 0.601124 -0.116525 0.419869 11.00000 -1.20000
AFIX 0
C4 1 0.706018 0.438919 0.477911 11.00000 0.02473 0.03213 =
0.03501 -0.00116 0.01230 -0.00120
C3 1 1.029261 0.239368 0.421443 11.00000 0.02740 0.03698 =
0.04495 -0.00126 0.00906 0.00159
N3 3 1.173090 0.422470 0.354011 11.00000 0.04667 0.03859 =
0.06034 0.00519 0.02573 0.00870
AFIX 93
H3A 2 1.215931 0.379887 0.341683 11.00000 -1.20000
H3B 2 1.155841 0.545391 0.350398 11.00000 -1.20000
AFIX 0
C2 1 0.836129 0.536650 0.442905 11.00000 0.03702 0.03551 =
0.07795 0.01170 0.02530 0.00961
AFIX 43
H2A 2 0.811415 0.658606 0.435028 11.00000 -1.20000
AFIX 0
C1 1 0.913703 0.488543 0.429203 11.00000 0.03834 0.03825 =
0.07781 0.01466 0.03134 0.00469
AFIX 43
H1 2 0.940858 0.578362 0.412346 11.00000 -1.20000
AFIX 0
O1 4 1.091383 0.766993 0.309416 11.00000 0.08735 0.06693 =
0.08958 0.00692 -0.00226 0.01526
O1W 4 0.223891 -1.359627 0.263170 11.00000 0.15963 0.07891 =
0.09148 -0.01870 0.02355 -0.04921
N13 3 1.005080 1.035406 0.311094 11.00000 0.09162 0.09307 =
0.11600 -0.03028 -0.05294 0.02568
C31 1 1.064842 0.931572 0.304492 11.00000 0.25136 0.19962 =
0.29748 -0.17090 -0.21707 0.16081
AFIX 43
H31 2 1.103071 1.009322 0.290707 11.00000 -1.20000
AFIX 0
C30 1 0.984697 1.226951 0.300643 11.00000 0.48328 0.13698 =
0.30166 -0.02662 -0.32179 0.03761
AFIX 33
H30A 2 0.931696 1.259960 0.311242 11.00000 -1.50000
H30B 2 0.982687 1.237737 0.272019 11.00000 -1.50000
H30C 2 1.025126 1.320185 0.311190 11.00000 -1.50000
AFIX 0
C29 1 0.945997 0.931102 0.335773 11.00000 0.17281 0.48727 =
0.12506 -0.04111 0.00253 -0.17395
AFIX 33
H29A 2 0.899676 1.018923 0.340223 11.00000 -1.50000
H29B 2 0.971336 0.896305 0.360967 11.00000 -1.50000
H29C 2 0.927744 0.808812 0.322518 11.00000 -1.50000
AFIX 0
N14 3 0.285904 -1.897794 0.181661 11.00000 0.06819 0.21526 =
0.12395 0.08114 -0.00354 -0.01499
O2 4 0.209463 -1.731634 0.226771 11.00000 0.34404 0.16326 =
0.28709 -0.13412 -0.16009 0.13893
C34 1 0.238763 -1.886285 0.212648 11.00000 0.18833 0.10522 =
0.10308 -0.00360 -0.03020 0.00026
AFIX 43
H34 2 0.226134 -2.008589 0.225314 11.00000 -1.20000
AFIX 0
C33 1 0.319796 -2.074826 0.166671 11.00000 0.12050 0.41788 =
0.25223 -0.17714 -0.05840 0.12189
AFIX 33
H33A 2 0.352370 -2.042799 0.143769 11.00000 -1.50000
H33B 2 0.276548 -2.167396 0.158984 11.00000 -1.50000
H33C 2 0.354046 -2.137421 0.186832 11.00000 -1.50000
AFIX 0
C32 1 0.310085 -1.706361 0.165856 11.00000 0.09652 0.45477 =
0.67429 0.43019 0.05935 -0.00864
AFIX 33
H32A 2 0.344717 -1.727796 0.143205 11.00000 -1.50000
H32B 2 0.339856 -1.630846 0.185969 11.00000 -1.50000
H32C 2 0.262059 -1.630807 0.157691 11.00000 -1.50000
AFIX 0
H2 2 0.432087 0.390410 0.496399 11.00000 0.01660
H1WA 2 0.210968 -1.486433 0.259409 11.00000 0.07257
H1WB 2 0.271787 -1.355106 0.252525 11.00000 0.23540
HKLF 4
REM 1 in P2(1)/c
REM R1 = 0.0723 for 4410 Fo > 4sig(Fo) and 0.1054 for all 6450 data
REM 472 parameters refined using 4 restraints
END
WGHT 0.1110 1.6534
REM Highest difference peak 0.612, deepest hole -0.673, 1-sigma level 0.061
Q1 1 0.1984 -1.7738 0.2334 11.00000 0.05 0.61
Q2 1 1.0560 1.1288 0.2774 11.00000 0.05 0.59
Q3 1 1.0817 0.9369 0.2992 11.00000 0.05 0.53
Q4 1 1.0260 0.8454 0.3290 11.00000 0.05 0.40
Q5 1 0.2478 -1.5065 0.2491 11.00000 0.05 0.34
Q6 1 0.9311 1.1263 0.3240 11.00000 0.05 0.30
Q7 1 0.2977 -2.1680 0.1714 11.00000 0.05 0.28
Q8 1 0.3256 -2.3414 0.1687 11.00000 0.05 0.27
Q9 1 0.3173 -1.6564 0.1811 11.00000 0.05 0.26
Q10 1 1.0733 0.1550 0.4532 11.00000 0.05 0.25
Q11 1 0.2996 -1.3659 0.2612 11.00000 0.05 0.23
Q12 1 0.4148 -0.4950 0.3518 11.00000 0.05 0.22
Q13 1 1.2037 0.4227 0.3821 11.00000 0.05 0.22
Q14 1 0.3635 -2.0209 0.1284 11.00000 0.05 0.21
Q15 1 0.4982 -0.6535 0.3352 11.00000 0.05 0.20
Q16 1 0.3137 -1.8960 0.1399 11.00000 0.05 0.20
Q17 1 0.3958 -0.4320 0.3774 11.00000 0.05 0.20
Q18 1 1.1285 1.3007 0.2894 11.00000 0.05 0.19
Q19 1 0.2680 -1.4990 0.1883 11.00000 0.05 0.19
Q20 1 0.1647 -2.2373 0.1512 11.00000 0.05 0.19
;
_shelx_res_checksum 70613
_olex2_submission_special_instructions 'No special instructions were received'