# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
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# 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
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data_1_8_20srv004a
_database_code_depnum_ccdc_archive 'CCDC 2000830'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record
;
2020-05-04 deposited with the CCDC. 2020-07-20 downloaded from the CCDC.
;
_audit_creation_date 2020-02-03
_audit_creation_method
;
Olex2 1.3-beta
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number 2017/1
loop_
_audit_author_email
d.s.yufit@durham.ac.uk
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C25 H41 O2, C4 H12 N'
_chemical_formula_sum 'C29 H53 N O2'
_chemical_formula_weight 447.72
_chemical_absolute_configuration unk
_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 4
_space_group_name_H-M_alt 'P 1 21 1'
_space_group_name_Hall 'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a 4.5997(3)
_cell_length_b 56.635(4)
_cell_length_c 5.5074(4)
_cell_angle_alpha 90
_cell_angle_beta 99.223(4)
_cell_angle_gamma 90
_cell_volume 1416.16(17)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 2344
_cell_measurement_temperature 120.0
_cell_measurement_theta_max 68.79
_cell_measurement_theta_min 3.12
_shelx_estimated_absorpt_T_max 0.990
_shelx_estimated_absorpt_T_min 0.893
_exptl_absorpt_coefficient_mu 0.483
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.7971
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0911 before and 0.0693 after correction.
The Ratio of minimum to maximum transmission is 0.7971.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear blue'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_primary blue
_exptl_crystal_density_diffrn 1.050
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plank
_exptl_crystal_F_000 500
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.09
_exptl_crystal_size_min 0.02
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.1008
_diffrn_reflns_av_unetI/netI 0.1311
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_h_min -4
_diffrn_reflns_limit_k_max 68
_diffrn_reflns_limit_k_min -69
_diffrn_reflns_limit_l_max 6
_diffrn_reflns_limit_l_min -6
_diffrn_reflns_number 14017
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full 67.679
_diffrn_reflns_theta_max 69.996
_diffrn_reflns_theta_min 3.121
_diffrn_ambient_temperature 120.0
_diffrn_detector 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device '3-circle diffractometer'
_diffrn_measurement_device_type D8Venture
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type 'Cu K\a'
_diffrn_radiation_wavelength 1.54178
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_current 1.0
_diffrn_source_power 0.05
_diffrn_source_type 'Incoatec I\mS microsource'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.814
_reflns_Friedel_fraction_full 0.830
_reflns_Friedel_fraction_max 0.807
_reflns_number_gt 2440
_reflns_number_total 4784
_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_bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'SAINT v8.40A (Bruker AXS, 2019)'
_computing_data_collection 'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction 'SAINT v8.40A (Bruker AXS, 2019)'
_computing_molecular_graphics 'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution 'XS (Sheldrick, 2008)'
_refine_diff_density_max 0.216
_refine_diff_density_min -0.181
_refine_diff_density_rms 0.052
_refine_ls_abs_structure_details
;
Flack x determined using 749 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.1(6)
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.045
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 292
_refine_ls_number_reflns 4784
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.1647
_refine_ls_R_factor_gt 0.0894
_refine_ls_restrained_S_all 1.045
_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^)+(0.0890P)^2^+0.8900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.2105
_refine_ls_wR_factor_ref 0.2497
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H,H) groups, All N(H,H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C26(H26A,H26B), C27(H27A,
H27B), C28(H28A,H28B)
2.b Idealised Me refined as rotating group:
C25(H25A,H25B,H25C), N1(H1A,H1B,H1C), C29(H29A,H29B,H29C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_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
O1 O 0.2503(13) 0.46740(12) 2.4676(11) 0.0500(16) Uani 1 1 d . . . . .
O2 O -0.0456(15) 0.45610(11) 2.1325(11) 0.0541(17) Uani 1 1 d . . . . .
C1 C 0.152(2) 0.46921(17) 2.2430(18) 0.046(2) Uani 1 1 d . . . . .
C2 C 0.292(2) 0.48786(17) 2.0943(16) 0.049(2) Uani 1 1 d . . . . .
H2A H 0.422112 0.498092 2.210449 0.059 Uiso 1 1 calc R U . . .
H2B H 0.416775 0.479690 1.989920 0.059 Uiso 1 1 calc R U . . .
C3 C 0.071(2) 0.50344(15) 1.9305(17) 0.046(2) Uani 1 1 d . . . . .
H3A H -0.064313 0.493324 1.817585 0.056 Uiso 1 1 calc R U . . .
H3B H -0.047372 0.512351 2.034375 0.056 Uiso 1 1 calc R U . . .
C4 C 0.222(2) 0.52067(15) 1.7810(17) 0.045(2) Uani 1 1 d . . . . .
H4A H 0.350034 0.511733 1.685005 0.054 Uiso 1 1 calc R U . . .
H4B H 0.350313 0.531256 1.894806 0.054 Uiso 1 1 calc R U . . .
C5 C 0.008(2) 0.53559(15) 1.6057(16) 0.041(2) Uani 1 1 d . . . . .
H5A H -0.126057 0.524962 1.497776 0.049 Uiso 1 1 calc R U . . .
H5B H -0.112725 0.545080 1.702782 0.049 Uiso 1 1 calc R U . . .
C6 C 0.1558(19) 0.55209(17) 1.4462(16) 0.044(2) Uani 1 1 d . . . . .
H6A H 0.277905 0.542612 1.349887 0.053 Uiso 1 1 calc R U . . .
H6B H 0.289223 0.562789 1.554074 0.053 Uiso 1 1 calc R U . . .
C7 C -0.061(2) 0.56711(16) 1.2672(17) 0.046(2) Uani 1 1 d . . . . .
H7A H -0.198065 0.556462 1.161905 0.055 Uiso 1 1 calc R U . . .
H7B H -0.179221 0.576980 1.363312 0.055 Uiso 1 1 calc R U . . .
C8 C 0.089(2) 0.58294(16) 1.1050(17) 0.046(2) Uani 1 1 d . . . . .
H8A H 0.195230 0.573011 0.999793 0.055 Uiso 1 1 calc R U . . .
H8B H 0.236937 0.592763 1.210045 0.055 Uiso 1 1 calc R U . . .
C9 C -0.124(2) 0.59907(16) 0.9413(17) 0.047(2) Uani 1 1 d . . . . .
H9A H -0.280121 0.589293 0.845366 0.057 Uiso 1 1 calc R U . . .
H9B H -0.219389 0.609772 1.046940 0.057 Uiso 1 1 calc R U . . .
C10 C 0.014(2) 0.61301(16) 0.7743(19) 0.050(3) Uani 1 1 d . . . . .
C11 C 0.134(2) 0.62419(19) 0.6305(19) 0.052(3) Uani 1 1 d . . . . .
C12 C 0.267(2) 0.63692(18) 0.4671(19) 0.051(2) Uani 1 1 d . . . . .
C13 C 0.386(2) 0.64777(18) 0.3239(17) 0.050(3) Uani 1 1 d . . . . .
C14 C 0.527(2) 0.66189(16) 0.1495(19) 0.052(3) Uani 1 1 d . . . . .
H14A H 0.619072 0.651032 0.043016 0.062 Uiso 1 1 calc R U . . .
H14B H 0.686344 0.671523 0.243754 0.062 Uiso 1 1 calc R U . . .
C15 C 0.3169(19) 0.67814(17) -0.0120(16) 0.044(2) Uani 1 1 d . . . . .
H15A H 0.214250 0.688252 0.093918 0.053 Uiso 1 1 calc R U . . .
H15B H 0.166364 0.668465 -0.115941 0.053 Uiso 1 1 calc R U . . .
C16 C 0.470(2) 0.69382(16) -0.1773(17) 0.047(2) Uani 1 1 d . . . . .
H16A H 0.586451 0.683767 -0.273373 0.057 Uiso 1 1 calc R U . . .
H16B H 0.609031 0.704434 -0.073244 0.057 Uiso 1 1 calc R U . . .
C17 C 0.253(2) 0.70890(16) -0.3568(16) 0.041(2) Uani 1 1 d . . . . .
H17A H 0.121079 0.698243 -0.466672 0.049 Uiso 1 1 calc R U . . .
H17B H 0.128854 0.718254 -0.260926 0.049 Uiso 1 1 calc R U . . .
C18 C 0.4038(19) 0.72562(15) -0.5133(16) 0.041(2) Uani 1 1 d . . . . .
H18A H 0.526710 0.716299 -0.610214 0.049 Uiso 1 1 calc R U . . .
H18B H 0.536039 0.736273 -0.403723 0.049 Uiso 1 1 calc R U . . .
C19 C 0.187(2) 0.74043(16) -0.6879(16) 0.043(2) Uani 1 1 d . . . . .
H19A H 0.064665 0.749768 -0.590771 0.051 Uiso 1 1 calc R U . . .
H19B H 0.054424 0.729757 -0.796862 0.051 Uiso 1 1 calc R U . . .
C20 C 0.339(2) 0.75740(16) -0.8483(17) 0.046(2) Uani 1 1 d . . . . .
H20A H 0.469195 0.768252 -0.739611 0.055 Uiso 1 1 calc R U . . .
H20B H 0.463467 0.748102 -0.943895 0.055 Uiso 1 1 calc R U . . .
C21 C 0.120(2) 0.77190(17) -1.0252(16) 0.045(2) Uani 1 1 d . . . . .
H21A H -0.005759 0.761106 -1.137985 0.054 Uiso 1 1 calc R U . . .
H21B H -0.008789 0.780840 -0.930366 0.054 Uiso 1 1 calc R U . . .
C22 C 0.273(2) 0.78907(16) -1.1755(17) 0.048(2) Uani 1 1 d . . . . .
H22A H 0.407402 0.780119 -1.264785 0.058 Uiso 1 1 calc R U . . .
H22B H 0.393755 0.800127 -1.062129 0.058 Uiso 1 1 calc R U . . .
C23 C 0.059(2) 0.80337(15) -1.3616(17) 0.046(2) Uani 1 1 d . . . . .
H23A H -0.063739 0.792294 -1.473226 0.055 Uiso 1 1 calc R U . . .
H23B H -0.073259 0.812495 -1.271962 0.055 Uiso 1 1 calc R U . . .
C24 C 0.209(2) 0.82016(17) -1.5139(18) 0.054(3) Uani 1 1 d . . . . .
H24A H 0.342241 0.810988 -1.603066 0.064 Uiso 1 1 calc R U . . .
H24B H 0.333004 0.831169 -1.401810 0.064 Uiso 1 1 calc R U . . .
C25 C 0.000(2) 0.83460(17) -1.7005(19) 0.060(3) Uani 1 1 d . . . . .
H25A H -0.109803 0.823979 -1.822388 0.090 Uiso 1 1 calc R U . . .
H25B H 0.114410 0.845765 -1.783484 0.090 Uiso 1 1 calc R U . . .
H25C H -0.137329 0.843311 -1.615365 0.090 Uiso 1 1 calc R U . . .
N1 N -0.2246(16) 0.44747(13) 1.6567(14) 0.048(2) Uani 1 1 d . . . . .
H1A H -0.138084 0.451691 1.810827 0.058 Uiso 1 1 calc R U . . .
H1B H -0.396568 0.455527 1.615476 0.058 Uiso 1 1 calc R U . . .
H1C H -0.101673 0.450976 1.547654 0.058 Uiso 1 1 calc R U . . .
C26 C -0.285(2) 0.42190(17) 1.6502(17) 0.053(3) Uani 1 1 d . . . . .
H26A H -0.419488 0.418271 1.768738 0.064 Uiso 1 1 calc R U . . .
H26B H -0.098357 0.413320 1.703959 0.064 Uiso 1 1 calc R U . . .
C27 C -0.424(2) 0.41287(17) 1.3948(17) 0.056(3) Uani 1 1 d . . . . .
H27A H -0.604179 0.422088 1.336054 0.068 Uiso 1 1 calc R U . . .
H27B H -0.284012 0.415499 1.278131 0.068 Uiso 1 1 calc R U . . .
C28 C -0.501(3) 0.38716(18) 1.3957(18) 0.067(3) Uani 1 1 d . . . . .
H28A H -0.318805 0.378003 1.450352 0.080 Uiso 1 1 calc R U . . .
H28B H -0.634657 0.384542 1.517079 0.080 Uiso 1 1 calc R U . . .
C29 C -0.644(3) 0.3779(2) 1.1524(19) 0.083(4) Uani 1 1 d . . . . .
H29A H -0.502616 0.378165 1.037149 0.125 Uiso 1 1 calc R U . . .
H29B H -0.813691 0.387896 1.088547 0.125 Uiso 1 1 calc R U . . .
H29C H -0.710976 0.361717 1.171496 0.125 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.046(4) 0.068(4) 0.035(4) 0.001(3) 0.003(3) 0.001(3)
O2 0.064(4) 0.054(4) 0.042(4) 0.001(3) 0.000(3) -0.013(3)
C1 0.051(6) 0.047(6) 0.042(6) 0.000(5) 0.011(5) 0.006(5)
C2 0.049(6) 0.055(6) 0.041(6) 0.004(5) 0.001(5) -0.002(5)
C3 0.050(6) 0.048(6) 0.037(5) 0.000(4) -0.007(5) 0.002(5)
C4 0.041(6) 0.047(6) 0.050(6) -0.003(5) 0.009(5) -0.001(4)
C5 0.039(5) 0.046(5) 0.035(5) 0.000(4) 0.000(4) -0.004(4)
C6 0.044(6) 0.052(6) 0.038(5) -0.001(5) 0.007(4) -0.002(5)
C7 0.052(6) 0.047(5) 0.040(6) 0.004(5) 0.009(5) -0.003(5)
C8 0.052(6) 0.047(6) 0.038(6) 0.008(4) 0.006(5) 0.000(5)
C9 0.048(6) 0.056(6) 0.036(5) 0.011(5) 0.003(5) -0.005(5)
C10 0.045(6) 0.048(6) 0.050(6) 0.007(5) -0.009(5) 0.001(5)
C11 0.052(6) 0.053(6) 0.047(6) -0.002(5) -0.003(5) 0.000(5)
C12 0.051(6) 0.063(7) 0.040(5) 0.001(5) 0.007(5) 0.007(5)
C13 0.051(6) 0.064(7) 0.037(6) -0.003(5) 0.010(5) 0.004(5)
C14 0.045(6) 0.054(6) 0.059(7) 0.005(5) 0.017(5) 0.005(5)
C15 0.037(6) 0.063(6) 0.032(5) 0.001(5) 0.003(4) -0.004(5)
C16 0.043(6) 0.064(6) 0.036(6) 0.004(5) 0.012(4) -0.005(5)
C17 0.041(5) 0.053(5) 0.028(5) 0.001(4) 0.005(4) -0.001(5)
C18 0.036(5) 0.050(6) 0.037(5) 0.005(4) 0.007(4) 0.000(4)
C19 0.036(6) 0.058(6) 0.033(5) 0.005(4) 0.002(4) -0.001(4)
C20 0.040(6) 0.053(6) 0.044(6) 0.001(5) 0.007(5) 0.000(5)
C21 0.042(6) 0.065(6) 0.028(5) 0.003(5) 0.004(4) 0.004(5)
C22 0.042(6) 0.054(6) 0.048(6) 0.005(5) 0.004(5) 0.000(5)
C23 0.040(5) 0.051(6) 0.042(5) -0.001(5) -0.006(4) 0.002(4)
C24 0.054(7) 0.053(6) 0.051(6) 0.003(5) 0.000(5) 0.003(5)
C25 0.063(7) 0.055(6) 0.058(7) 0.010(5) -0.004(6) -0.003(5)
N1 0.039(4) 0.061(5) 0.042(4) -0.001(4) -0.001(3) 0.001(4)
C26 0.056(7) 0.060(7) 0.042(6) 0.010(5) 0.003(5) -0.002(5)
C27 0.071(7) 0.058(6) 0.037(6) -0.003(5) -0.002(5) -0.001(5)
C28 0.086(9) 0.052(6) 0.057(7) 0.005(5) -0.001(6) -0.009(6)
C29 0.114(11) 0.062(8) 0.063(8) -0.009(6) -0.018(8) -0.009(7)
_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
O1 C1 1.252(10) . ?
O2 C1 1.252(11) . ?
C1 C2 1.540(12) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.526(12) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.515(12) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.521(12) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.515(12) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.541(12) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.509(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.525(12) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.436(13) . ?
C10 C11 1.214(14) . ?
C11 C12 1.371(14) . ?
C12 C13 1.200(13) . ?
C13 C14 1.477(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.516(12) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.523(12) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.546(12) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.521(11) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.521(11) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.546(12) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.524(12) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.520(12) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.532(11) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.507(13) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.527(12) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C26 1.474(11) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.536(12) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.499(13) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29 1.490(13) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
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
O1 C1 C2 117.7(9) . . ?
O2 C1 O1 123.5(9) . . ?
O2 C1 C2 118.8(8) . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C3 C2 C1 114.5(8) . . ?
C3 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 112.0(8) . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C3 C4 C5 113.4(7) . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 C4 114.0(8) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
C5 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C5 C6 C7 114.0(7) . . ?
H6A C6 H6B 107.6 . . ?
C7 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 C6 113.3(8) . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C7 C8 C9 113.2(8) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C8 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C8 113.6(8) . . ?
C10 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C11 C10 C9 178.0(11) . . ?
C10 C11 C12 179.4(12) . . ?
C13 C12 C11 179.0(11) . . ?
C12 C13 C14 178.0(11) . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C13 C14 C15 113.9(8) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C14 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C14 C15 C16 113.0(7) . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C15 C16 C17 113.0(7) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C16 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 C16 113.5(7) . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C17 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C17 C18 C19 112.9(7) . . ?
H18A C18 H18B 107.8 . . ?
C19 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C18 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C18 C19 C20 113.2(7) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C19 C20 H20A 109.0 . . ?
C19 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C21 C20 C19 112.9(7) . . ?
C21 C20 H20A 109.0 . . ?
C21 C20 H20B 109.0 . . ?
C20 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 C20 112.2(8) . . ?
C22 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C21 C22 H22A 108.8 . . ?
C21 C22 H22B 108.8 . . ?
C21 C22 C23 113.6(8) . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
C22 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 C22 113.9(8) . . ?
C24 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C23 C24 H24A 108.6 . . ?
C23 C24 H24B 108.6 . . ?
C23 C24 C25 114.7(8) . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 H24A 108.6 . . ?
C25 C24 H24B 108.6 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C26 N1 H1A 109.5 . . ?
C26 N1 H1B 109.5 . . ?
C26 N1 H1C 109.5 . . ?
N1 C26 H26A 108.9 . . ?
N1 C26 H26B 108.9 . . ?
N1 C26 C27 113.5(8) . . ?
H26A C26 H26B 107.7 . . ?
C27 C26 H26A 108.9 . . ?
C27 C26 H26B 108.9 . . ?
C26 C27 H27A 109.1 . . ?
C26 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?
C28 C27 C26 112.6(8) . . ?
C28 C27 H27A 109.1 . . ?
C28 C27 H27B 109.1 . . ?
C27 C28 H28A 108.7 . . ?
C27 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
C29 C28 C27 114.1(9) . . ?
C29 C28 H28A 108.7 . . ?
C29 C28 H28B 108.7 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O2 0.91 1.77 2.663(10) 165.7 . yes
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
O1 C1 C2 C3 -132.1(9) . . . . ?
O2 C1 C2 C3 50.7(12) . . . . ?
C1 C2 C3 C4 -177.5(8) . . . . ?
C2 C3 C4 C5 177.0(8) . . . . ?
C3 C4 C5 C6 -177.2(8) . . . . ?
C4 C5 C6 C7 179.6(8) . . . . ?
C5 C6 C7 C8 -178.4(8) . . . . ?
C6 C7 C8 C9 -175.8(8) . . . . ?
C7 C8 C9 C10 -175.9(8) . . . . ?
C13 C14 C15 C16 175.8(8) . . . . ?
C14 C15 C16 C17 175.3(8) . . . . ?
C15 C16 C17 C18 176.9(8) . . . . ?
C16 C17 C18 C19 -179.7(8) . . . . ?
C17 C18 C19 C20 -179.8(7) . . . . ?
C18 C19 C20 C21 179.2(8) . . . . ?
C19 C20 C21 C22 178.1(7) . . . . ?
C20 C21 C22 C23 178.1(8) . . . . ?
C21 C22 C23 C24 -179.1(8) . . . . ?
C22 C23 C24 C25 -179.9(8) . . . . ?
N1 C26 C27 C28 -176.4(9) . . . . ?
C26 C27 C28 C29 178.2(11) . . . . ?
_iucr_refine_instructions_details
;
TITL 20srv004A in P21 #4
REM reset to P21 #4
CELL 1.54178 4.5997 56.6354 5.5074 90 99.2232 90
ZERR 2 0.0003 0.0039 0.0004 0 0.0038 0
LATT -1
SYMM -X,0.5+Y,-Z
SFAC C H N O
UNIT 58 106 2 4
L.S. 9
PLAN 12
SIZE 0.02 0.09 0.24
TEMP -153
CONF
HTAB N1 O2
BOND $h
fmap 2 53
acta
OMIT -2 140
OMIT 1 0 2
OMIT 1 0 3
WGHT 0.089 0.89
FVAR 0.23565
REM
REM
REM
O1 4 0.25027 0.46740 2.46763 11.00000 0.04603 0.06808 0.03478 =
0.00099 0.00327 0.00149
O2 4 -0.04559 0.45610 2.13247 11.00000 0.06395 0.05400 0.04160 =
0.00062 0.00021 -0.01324
C1 1 0.15155 0.46921 2.24296 11.00000 0.05105 0.04703 0.04225 =
0.00029 0.01073 0.00565
C2 1 0.29200 0.48786 2.09432 11.00000 0.04917 0.05497 0.04062 =
0.00401 0.00093 -0.00236
AFIX 23
H2a 2 0.42211 0.49809 2.21045 11.00000 -1.20000
H2b 2 0.41678 0.47969 1.98992 11.00000 -1.20000
AFIX 0
C3 1 0.07134 0.50344 1.93051 11.00000 0.04951 0.04791 0.03721 =
-0.00025 -0.00701 0.00232
AFIX 23
H3a 2 -0.06431 0.49332 1.81759 11.00000 -1.20000
H3b 2 -0.04737 0.51235 2.03437 11.00000 -1.20000
AFIX 0
C4 1 0.22240 0.52067 1.78104 11.00000 0.04052 0.04664 0.04963 =
-0.00261 0.00909 -0.00095
AFIX 23
H4a 2 0.35003 0.51173 1.68500 11.00000 -1.20000
H4b 2 0.35031 0.53126 1.89481 11.00000 -1.20000
AFIX 0
C5 1 0.00833 0.53560 1.60567 11.00000 0.03932 0.04604 0.03489 =
0.00013 0.00010 -0.00351
AFIX 23
H5a 2 -0.12606 0.52496 1.49778 11.00000 -1.20000
H5b 2 -0.11273 0.54508 1.70278 11.00000 -1.20000
AFIX 0
C6 1 0.15581 0.55209 1.44616 11.00000 0.04367 0.05158 0.03785 =
-0.00133 0.00738 -0.00225
AFIX 23
H6a 2 0.27791 0.54261 1.34989 11.00000 -1.20000
H6b 2 0.28922 0.56279 1.55407 11.00000 -1.20000
AFIX 0
C7 1 -0.06106 0.56711 1.26719 11.00000 0.05207 0.04702 0.03978 =
0.00427 0.00855 -0.00275
AFIX 23
H7a 2 -0.19806 0.55646 1.16191 11.00000 -1.20000
H7b 2 -0.17922 0.57698 1.36331 11.00000 -1.20000
AFIX 0
C8 1 0.08922 0.58294 1.10501 11.00000 0.05244 0.04665 0.03767 =
0.00839 0.00596 -0.00031
AFIX 23
H8a 2 0.19523 0.57301 0.99979 11.00000 -1.20000
H8b 2 0.23694 0.59276 1.21005 11.00000 -1.20000
AFIX 0
C9 1 -0.12398 0.59907 0.94133 11.00000 0.04843 0.05641 0.03567 =
0.01080 0.00253 -0.00503
AFIX 23
H9a 2 -0.28012 0.58929 0.84537 11.00000 -1.20000
H9b 2 -0.21939 0.60977 1.04694 11.00000 -1.20000
AFIX 0
C10 1 0.01410 0.61301 0.77427 11.00000 0.04493 0.04816 0.04991 =
0.00687 -0.00923 0.00082
C11 1 0.13436 0.62419 0.63046 11.00000 0.05216 0.05310 0.04707 =
-0.00235 -0.00266 0.00049
C12 1 0.26717 0.63692 0.46712 11.00000 0.05051 0.06270 0.03951 =
0.00095 0.00733 0.00700
C13 1 0.38631 0.64777 0.32388 11.00000 0.05072 0.06432 0.03718 =
-0.00348 0.01005 0.00417
C14 1 0.52730 0.66190 0.14952 11.00000 0.04482 0.05369 0.05930 =
0.00548 0.01688 0.00519
AFIX 23
H14a 2 0.61907 0.65103 0.04301 11.00000 -1.20000
H14b 2 0.68634 0.67152 0.24375 11.00000 -1.20000
AFIX 0
C15 1 0.31693 0.67814 -0.01203 11.00000 0.03688 0.06273 0.03171 =
0.00108 0.00313 -0.00426
AFIX 23
H15a 2 0.21425 0.68825 0.09392 11.00000 -1.20000
H15b 2 0.16636 0.66847 -0.11594 11.00000 -1.20000
AFIX 0
C16 1 0.47027 0.69382 -0.17730 11.00000 0.04269 0.06432 0.03632 =
0.00373 0.01160 -0.00476
AFIX 23
H16a 2 0.58645 0.68377 -0.27337 11.00000 -1.20000
H16b 2 0.60903 0.70443 -0.07324 11.00000 -1.20000
AFIX 0
C17 1 0.25273 0.70891 -0.35678 11.00000 0.04110 0.05323 0.02791 =
0.00143 0.00543 -0.00064
AFIX 23
H17a 2 0.12108 0.69824 -0.46667 11.00000 -1.20000
H17b 2 0.12885 0.71825 -0.26093 11.00000 -1.20000
AFIX 0
C18 1 0.40382 0.72562 -0.51327 11.00000 0.03632 0.05030 0.03655 =
0.00508 0.00651 -0.00046
AFIX 23
H18a 2 0.52671 0.71630 -0.61021 11.00000 -1.20000
H18b 2 0.53604 0.73627 -0.40372 11.00000 -1.20000
AFIX 0
C19 1 0.18711 0.74043 -0.68795 11.00000 0.03621 0.05775 0.03306 =
0.00492 0.00151 -0.00095
AFIX 23
H19a 2 0.06467 0.74977 -0.59077 11.00000 -1.20000
H19b 2 0.05442 0.72976 -0.79686 11.00000 -1.20000
AFIX 0
C20 1 0.33885 0.75740 -0.84828 11.00000 0.04040 0.05284 0.04390 =
0.00065 0.00740 0.00040
AFIX 23
H20a 2 0.46919 0.76825 -0.73961 11.00000 -1.20000
H20b 2 0.46347 0.74810 -0.94390 11.00000 -1.20000
AFIX 0
C21 1 0.12018 0.77190 -1.02518 11.00000 0.04171 0.06523 0.02816 =
0.00289 0.00370 0.00432
AFIX 23
H21a 2 -0.00576 0.76111 -1.13799 11.00000 -1.20000
H21b 2 -0.00879 0.78084 -0.93037 11.00000 -1.20000
AFIX 0
C22 1 0.27276 0.78907 -1.17551 11.00000 0.04190 0.05382 0.04755 =
0.00496 0.00355 0.00017
AFIX 23
H22a 2 0.40740 0.78012 -1.26479 11.00000 -1.20000
H22b 2 0.39376 0.80013 -1.06213 11.00000 -1.20000
AFIX 0
C23 1 0.05939 0.80337 -1.36165 11.00000 0.03984 0.05130 0.04183 =
-0.00055 -0.00557 0.00190
AFIX 23
H23a 2 -0.06374 0.79229 -1.47323 11.00000 -1.20000
H23b 2 -0.07326 0.81249 -1.27196 11.00000 -1.20000
AFIX 0
C24 1 0.20948 0.82016 -1.51389 11.00000 0.05434 0.05284 0.05089 =
0.00268 -0.00029 0.00292
AFIX 23
H24a 2 0.34224 0.81099 -1.60307 11.00000 -1.20000
H24b 2 0.33300 0.83117 -1.40181 11.00000 -1.20000
AFIX 0
C25 1 0.00047 0.83460 -1.70050 11.00000 0.06337 0.05478 0.05791 =
0.01043 -0.00355 -0.00349
AFIX 137
H25a 2 -0.10980 0.82398 -1.82239 11.00000 -1.50000
H25b 2 0.11441 0.84576 -1.78348 11.00000 -1.50000
H25c 2 -0.13733 0.84331 -1.61537 11.00000 -1.50000
AFIX 0
N1 3 -0.22457 0.44747 1.65665 11.00000 0.03867 0.06135 0.04187 =
-0.00077 -0.00092 0.00108
AFIX 137
H1a 2 -0.13808 0.45169 1.81083 11.00000 -1.20000
H1b 2 -0.39657 0.45553 1.61548 11.00000 -1.20000
H1c 2 -0.10167 0.45098 1.54765 11.00000 -1.20000
AFIX 0
C26 1 -0.28510 0.42190 1.65017 11.00000 0.05603 0.06007 0.04221 =
0.00992 0.00322 -0.00210
AFIX 23
H26a 2 -0.41949 0.41827 1.76874 11.00000 -1.20000
H26b 2 -0.09836 0.41332 1.70396 11.00000 -1.20000
AFIX 0
C27 1 -0.42371 0.41287 1.39477 11.00000 0.07088 0.05776 0.03703 =
-0.00272 -0.00230 -0.00121
AFIX 23
H27a 2 -0.60418 0.42209 1.33605 11.00000 -1.20000
H27b 2 -0.28401 0.41550 1.27813 11.00000 -1.20000
AFIX 0
C28 1 -0.50083 0.38716 1.39566 11.00000 0.08643 0.05226 0.05691 =
0.00476 -0.00134 -0.00914
AFIX 23
H28a 2 -0.31881 0.37800 1.45035 11.00000 -1.20000
H28b 2 -0.63466 0.38454 1.51708 11.00000 -1.20000
AFIX 0
C29 1 -0.64430 0.37795 1.15240 11.00000 0.11430 0.06228 0.06332 =
-0.00950 -0.01777 -0.00948
AFIX 137
H29a 2 -0.50262 0.37816 1.03715 11.00000 -1.50000
H29b 2 -0.81369 0.38790 1.08855 11.00000 -1.50000
H29c 2 -0.71098 0.36172 1.17150 11.00000 -1.50000
AFIX 0
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# 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_12_4_18srv481
_database_code_depnum_ccdc_archive 'CCDC 2000833'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record
;
2020-05-04 deposited with the CCDC. 2020-07-20 downloaded from the CCDC.
;
_audit_creation_date 2018-11-26
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2017/1
loop_
_audit_author_email
d.s.yufit@durham.ac.uk
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C25 H42 O2, C6 H5 N'
_chemical_formula_sum 'C31 H47 N O2'
_chemical_formula_weight 465.69
_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 0.0033 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'
_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 5.4494(3)
_cell_length_b 8.9235(5)
_cell_length_c 57.441(3)
_cell_angle_alpha 90
_cell_angle_beta 92.643(2)
_cell_angle_gamma 90
_cell_volume 2790.2(3)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 7852
_cell_measurement_temperature 120.0
_cell_measurement_theta_max 26.66
_cell_measurement_theta_min 2.31
_shelx_estimated_absorpt_T_max 0.985
_shelx_estimated_absorpt_T_min 0.976
_exptl_absorpt_coefficient_mu 0.067
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.9046
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1196 before and 0.0500 after correction. The Ratio of minimum to maximum transmission is 0.9046. The \l/2 correction factor is Not present.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.109
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description irregular
_exptl_crystal_F_000 1024
_exptl_crystal_size_max 0.36
_exptl_crystal_size_mid 0.31
_exptl_crystal_size_min 0.23
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0635
_diffrn_reflns_av_unetI/netI 0.0794
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 77
_diffrn_reflns_limit_l_min -74
_diffrn_reflns_number 34945
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 28.490
_diffrn_reflns_theta_min 2.130
_diffrn_ambient_temperature 120.0
_diffrn_detector 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device '3-circle diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Venture'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\mS microsource'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3792
_reflns_number_total 6537
_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_bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection 'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction 'SAINT v8.38A (Bruker AXS, 2016)'
_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 'XS (Sheldrick, 2008)'
_refine_diff_density_max 0.200
_refine_diff_density_min -0.285
_refine_diff_density_rms 0.046
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.034
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 321
_refine_ls_number_reflns 6537
_refine_ls_number_restraints 1
_refine_ls_R_factor_all 0.1242
_refine_ls_R_factor_gt 0.0560
_refine_ls_restrained_S_all 1.034
_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^)+(0.0530P)^2^+0.2900P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1073
_refine_ls_wR_factor_ref 0.1255
_refine_special_details ?
_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. Restrained distances
C6S-C3S \\sim C6SA-C3S
with sigma of 0.002
3. Others
Fixed Sof: C6S(0.6) H6S(0.6) C6SA(0.4) H6SA(0.4)
4.a Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
4.b Aromatic/amide H refined with riding coordinates:
C1S(H1S), C2S(H2S), C4S(H4S), C5S(H5S), C6S(H6S), C6SA(H6SA)
4.c Idealised Me refined as rotating group:
C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_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
O1 O 2.1835(2) 1.44720(12) 0.55142(2) 0.0338(3) Uani 1 1 d . . . . .
O2 O 2.41340(19) 1.24568(12) 0.54472(2) 0.0307(3) Uani 1 1 d . . . . .
C1 C 2.2338(3) 1.30197(17) 0.55283(3) 0.0215(4) Uani 1 1 d . . . . .
C2 C 2.0414(3) 1.21932(16) 0.56566(3) 0.0216(4) Uani 1 1 d . . . . .
H2A H 1.879984 1.236683 0.557490 0.026 Uiso 1 1 calc R . . . .
H2B H 2.034029 1.262935 0.581456 0.026 Uiso 1 1 calc R . . . .
C3 C 2.0804(3) 1.05200(16) 0.56806(3) 0.0216(4) Uani 1 1 d . . . . .
H3A H 2.239487 1.033350 0.576596 0.026 Uiso 1 1 calc R . . . .
H3B H 2.089043 1.007247 0.552351 0.026 Uiso 1 1 calc R . . . .
C4 C 1.8765(3) 0.97564(16) 0.58089(3) 0.0220(4) Uani 1 1 d . . . . .
H4A H 1.870687 1.019397 0.596694 0.026 Uiso 1 1 calc R . . . .
H4B H 1.717332 0.997012 0.572547 0.026 Uiso 1 1 calc R . . . .
C5 C 1.9073(3) 0.80671(17) 0.58311(3) 0.0226(4) Uani 1 1 d . . . . .
H5A H 1.916244 0.763061 0.567322 0.027 Uiso 1 1 calc R . . . .
H5B H 2.064889 0.785271 0.591731 0.027 Uiso 1 1 calc R . . . .
C6 C 1.7006(3) 0.73075(16) 0.59553(3) 0.0239(4) Uani 1 1 d . . . . .
H6A H 1.542048 0.756799 0.587435 0.029 Uiso 1 1 calc R . . . .
H6B H 1.697828 0.770032 0.611633 0.029 Uiso 1 1 calc R . . . .
C7 C 1.7254(3) 0.56107(16) 0.59647(3) 0.0222(4) Uani 1 1 d . . . . .
H7A H 1.884849 0.535413 0.604433 0.027 Uiso 1 1 calc R . . . .
H7B H 1.727571 0.522122 0.580342 0.027 Uiso 1 1 calc R . . . .
C8 C 1.5210(3) 0.48275(16) 0.60899(3) 0.0221(4) Uani 1 1 d . . . . .
H8A H 1.361386 0.503933 0.600706 0.026 Uiso 1 1 calc R . . . .
H8B H 1.514366 0.523015 0.625006 0.026 Uiso 1 1 calc R . . . .
C9 C 1.5613(3) 0.31369(17) 0.61011(3) 0.0221(4) Uani 1 1 d . . . . .
H9A H 1.568954 0.274798 0.594022 0.027 Uiso 1 1 calc R . . . .
H9B H 1.722285 0.293886 0.618220 0.027 Uiso 1 1 calc R . . . .
C10 C 1.3715(3) 0.23070(17) 0.62202(2) 0.0222(4) Uani 1 1 d . . . . .
C11 C 1.2156(3) 0.16268(17) 0.63157(3) 0.0215(4) Uani 1 1 d . . . . .
C12 C 1.0359(3) 0.08417(17) 0.64273(2) 0.0216(4) Uani 1 1 d . . . . .
C13 C 0.8795(3) 0.01540(17) 0.65202(3) 0.0226(4) Uani 1 1 d . . . . .
C14 C 0.6907(3) -0.06721(17) 0.66411(3) 0.0251(4) Uani 1 1 d . . . . .
H14A H 0.767949 -0.155167 0.671985 0.030 Uiso 1 1 calc R . . . .
H14B H 0.566452 -0.104863 0.652427 0.030 Uiso 1 1 calc R . . . .
C15 C 0.5612(3) 0.02632(17) 0.68218(2) 0.0203(3) Uani 1 1 d . . . . .
H15A H 0.685916 0.071939 0.693072 0.024 Uiso 1 1 calc R . . . .
H15B H 0.469280 0.108557 0.674161 0.024 Uiso 1 1 calc R . . . .
C16 C 0.3847(3) -0.06687(16) 0.69594(2) 0.0204(3) Uani 1 1 d . . . . .
H16A H 0.479015 -0.144605 0.704794 0.024 Uiso 1 1 calc R . . . .
H16B H 0.268209 -0.118570 0.684907 0.024 Uiso 1 1 calc R . . . .
C17 C 0.2395(3) 0.02560(16) 0.71286(2) 0.0202(3) Uani 1 1 d . . . . .
H17A H 0.356144 0.082242 0.723241 0.024 Uiso 1 1 calc R . . . .
H17B H 0.137541 0.099269 0.703886 0.024 Uiso 1 1 calc R . . . .
C18 C 0.0737(3) -0.06788(16) 0.72774(2) 0.0199(3) Uani 1 1 d . . . . .
H18A H 0.175973 -0.140964 0.736799 0.024 Uiso 1 1 calc R . . . .
H18B H -0.041825 -0.125207 0.717341 0.024 Uiso 1 1 calc R . . . .
C19 C -0.0733(3) 0.02422(16) 0.74453(2) 0.0195(3) Uani 1 1 d . . . . .
H19A H 0.042209 0.083062 0.754710 0.023 Uiso 1 1 calc R . . . .
H19B H -0.177817 0.096003 0.735432 0.023 Uiso 1 1 calc R . . . .
C20 C -0.2356(3) -0.06906(16) 0.75974(2) 0.0204(3) Uani 1 1 d . . . . .
H20A H -0.130960 -0.139880 0.769006 0.025 Uiso 1 1 calc R . . . .
H20B H -0.349774 -0.128906 0.749566 0.025 Uiso 1 1 calc R . . . .
C21 C -0.3849(3) 0.02373(16) 0.77629(2) 0.0201(3) Uani 1 1 d . . . . .
H21A H -0.270906 0.085774 0.786137 0.024 Uiso 1 1 calc R . . . .
H21B H -0.492834 0.092583 0.766983 0.024 Uiso 1 1 calc R . . . .
C22 C -0.5429(3) -0.06909(16) 0.79207(2) 0.0222(4) Uani 1 1 d . . . . .
H22A H -0.655349 -0.132295 0.782253 0.027 Uiso 1 1 calc R . . . .
H22B H -0.434899 -0.136751 0.801593 0.027 Uiso 1 1 calc R . . . .
C23 C -0.6941(3) 0.02466(17) 0.80825(2) 0.0212(3) Uani 1 1 d . . . . .
H23A H -0.802357 0.091976 0.798701 0.025 Uiso 1 1 calc R . . . .
H23B H -0.581413 0.088297 0.817980 0.025 Uiso 1 1 calc R . . . .
C24 C -0.8516(3) -0.06697(18) 0.82418(3) 0.0266(4) Uani 1 1 d . . . . .
H24A H -0.743140 -0.131370 0.834217 0.032 Uiso 1 1 calc R . . . .
H24B H -0.960300 -0.133385 0.814520 0.032 Uiso 1 1 calc R . . . .
C25 C -1.0088(3) 0.02897(18) 0.83960(3) 0.0307(4) Uani 1 1 d . . . . .
H25A H -1.118058 0.092320 0.829799 0.046 Uiso 1 1 calc GR . . . .
H25B H -0.902187 0.092401 0.849656 0.046 Uiso 1 1 calc GR . . . .
H25C H -1.107169 -0.036113 0.849265 0.046 Uiso 1 1 calc GR . . . .
H1 H 2.319(4) 1.500(2) 0.5436(3) 0.071(7) Uiso 1 1 d . . . . .
N1 N 0.4957(2) 0.37068(14) 0.46759(2) 0.0234(3) Uani 1 1 d . . . . .
C1S C 0.3014(3) 0.4100(2) 0.47915(3) 0.0329(4) Uani 1 1 d . . . . .
H1S H 0.265313 0.513658 0.480511 0.039 Uiso 1 1 calc R . . . .
C2S C 0.1500(3) 0.3097(2) 0.48923(3) 0.0436(5) Uani 1 1 d . . . . .
H2S H 0.013918 0.344473 0.497461 0.052 Uiso 1 1 calc R . . . .
C3S C 0.1935(3) 0.1590(2) 0.48753(3) 0.0436(5) Uani 1 1 d D . . . .
C4S C 0.3946(4) 0.11569(19) 0.47513(3) 0.0403(5) Uani 1 1 d . . . . .
H4S H 0.431983 0.012578 0.473195 0.048 Uiso 1 1 calc R . . . .
C5S C 0.5389(3) 0.22437(18) 0.46571(3) 0.0288(4) Uani 1 1 d . . . . .
H5S H 0.676880 0.193418 0.457397 0.035 Uiso 1 1 calc R . . . .
C6S C -0.0004(5) 0.0752(3) 0.50078(5) 0.0203(6) Uani 0.6 1 d D . P A 1
H6S H -0.116221 0.126854 0.509699 0.024 Uiso 0.6 1 calc R . P A 1
C6SA C 0.0918(9) 0.0049(4) 0.49362(8) 0.0278(10) Uani 0.4 1 d D . P A 2
H6SA H 0.165670 -0.083209 0.487866 0.033 Uiso 0.4 1 calc R . P A 2
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
O1 0.0299(7) 0.0207(7) 0.0521(8) 0.0095(6) 0.0147(6) -0.0017(5)
O2 0.0253(6) 0.0286(7) 0.0392(7) 0.0051(6) 0.0110(5) 0.0010(5)
C1 0.0211(9) 0.0208(9) 0.0224(8) 0.0029(7) -0.0003(7) -0.0024(7)
C2 0.0202(8) 0.0192(9) 0.0258(8) 0.0018(7) 0.0052(7) -0.0017(7)
C3 0.0203(8) 0.0188(9) 0.0261(9) 0.0007(7) 0.0040(7) -0.0009(7)
C4 0.0220(8) 0.0202(9) 0.0240(8) 0.0007(7) 0.0034(7) -0.0009(7)
C5 0.0206(8) 0.0192(9) 0.0283(9) 0.0037(7) 0.0048(7) -0.0003(7)
C6 0.0233(8) 0.0211(9) 0.0278(9) 0.0026(7) 0.0067(7) 0.0000(7)
C7 0.0211(8) 0.0204(9) 0.0254(9) 0.0032(7) 0.0044(7) 0.0007(7)
C8 0.0204(8) 0.0196(9) 0.0267(9) 0.0026(7) 0.0054(7) -0.0016(7)
C9 0.0195(8) 0.0214(9) 0.0258(9) 0.0054(7) 0.0059(7) -0.0022(7)
C10 0.0227(8) 0.0201(9) 0.0237(8) 0.0015(7) 0.0015(7) 0.0031(7)
C11 0.0217(8) 0.0209(9) 0.0221(8) 0.0027(7) 0.0034(7) 0.0009(7)
C12 0.0223(8) 0.0221(9) 0.0206(8) 0.0006(7) 0.0045(7) 0.0009(7)
C13 0.0244(9) 0.0205(9) 0.0234(8) -0.0005(7) 0.0064(7) 0.0012(7)
C14 0.0280(9) 0.0217(9) 0.0266(9) 0.0005(7) 0.0126(7) -0.0036(7)
C15 0.0202(8) 0.0201(8) 0.0209(8) 0.0009(7) 0.0056(6) -0.0020(7)
C16 0.0207(8) 0.0183(8) 0.0228(8) 0.0014(7) 0.0069(7) -0.0011(6)
C17 0.0201(8) 0.0176(8) 0.0234(8) 0.0004(7) 0.0063(7) -0.0003(7)
C18 0.0206(8) 0.0170(8) 0.0227(8) 0.0016(6) 0.0066(6) 0.0005(6)
C19 0.0190(8) 0.0178(8) 0.0219(8) 0.0003(7) 0.0050(6) 0.0003(6)
C20 0.0211(8) 0.0177(8) 0.0232(8) 0.0002(7) 0.0071(6) 0.0009(6)
C21 0.0200(8) 0.0178(8) 0.0229(8) -0.0002(7) 0.0048(6) 0.0014(6)
C22 0.0221(8) 0.0199(9) 0.0253(9) 0.0003(7) 0.0087(7) 0.0004(7)
C23 0.0205(8) 0.0201(8) 0.0234(8) 0.0016(7) 0.0051(7) 0.0008(7)
C24 0.0270(9) 0.0254(9) 0.0282(9) 0.0010(7) 0.0102(7) -0.0008(7)
C25 0.0316(9) 0.0331(10) 0.0286(9) 0.0019(8) 0.0131(8) 0.0007(8)
N1 0.0222(7) 0.0197(7) 0.0286(8) 0.0033(6) 0.0036(6) -0.0018(6)
C1S 0.0299(10) 0.0297(10) 0.0393(10) -0.0080(8) 0.0044(8) 0.0030(8)
C2S 0.0281(10) 0.0695(16) 0.0340(11) 0.0007(10) 0.0111(8) -0.0098(10)
C3S 0.0352(11) 0.0616(15) 0.0323(11) 0.0258(10) -0.0169(9) -0.0310(10)
C4S 0.0527(12) 0.0174(9) 0.0480(12) 0.0086(8) -0.0280(10) -0.0074(9)
C5S 0.0264(9) 0.0282(10) 0.0316(9) -0.0025(8) -0.0011(7) 0.0058(8)
C6S 0.0220(18) 0.018(2) 0.0208(15) -0.0035(13) 0.0022(13) 0.0073(13)
C6SA 0.031(3) 0.022(3) 0.030(3) 0.009(2) -0.006(2) -0.008(2)
_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
O1 C1 1.3262(18) . ?
O1 H1 1.00(2) . ?
O2 C1 1.2122(17) . ?
C1 C2 1.502(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.514(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5224(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.521(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5203(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.521(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5233(19) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.525(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.467(2) . ?
C10 C11 1.197(2) . ?
C11 C12 1.386(2) . ?
C12 C13 1.1957(19) . ?
C13 C14 1.466(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5294(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5206(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5238(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5210(18) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5228(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.5201(19) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.5240(18) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.5232(19) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.5209(19) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5214(19) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.5236(19) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N1 C1S 1.3229(19) . ?
N1 C5S 1.3319(19) . ?
C1S H1S 0.9500 . ?
C1S C2S 1.364(2) . ?
C2S H2S 0.9500 . ?
C2S C3S 1.370(3) . ?
C3S C4S 1.389(3) . ?
C3S C6S 1.526(2) . ?
C3S C6SA 1.528(3) . ?
C4S H4S 0.9500 . ?
C4S C5S 1.375(2) . ?
C5S H5S 0.9500 . ?
C6S C6S 1.346(6) 3_556 ?
C6S H6S 0.9500 . ?
C6SA C6SA 1.270(11) 3_556 ?
C6SA H6SA 0.9500 . ?
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
C1 O1 H1 109.8(12) . . ?
O1 C1 C2 111.28(13) . . ?
O2 C1 O1 123.33(14) . . ?
O2 C1 C2 125.38(14) . . ?
C1 C2 H2A 108.4 . . ?
C1 C2 H2B 108.4 . . ?
C1 C2 C3 115.53(12) . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 H2A 108.4 . . ?
C3 C2 H2B 108.4 . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C2 C3 C4 112.53(12) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 C3 113.81(12) . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 C4 113.56(13) . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C5 C6 C7 113.21(12) . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C6 C7 C8 114.08(12) . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
C7 C8 C9 111.52(12) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C8 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 C8 114.58(13) . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C11 C10 C9 179.48(16) . . ?
C10 C11 C12 179.69(17) . . ?
C13 C12 C11 178.91(16) . . ?
C12 C13 C14 178.22(16) . . ?
C13 C14 H14A 108.8 . . ?
C13 C14 H14B 108.8 . . ?
C13 C14 C15 113.75(13) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.8 . . ?
C15 C14 H14B 108.8 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C14 112.16(12) . . ?
C16 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
C15 C16 C17 113.26(12) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 C16 113.61(12) . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C17 C18 C19 113.79(12) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 C18 113.94(12) . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C19 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
C19 C20 C21 113.75(12) . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C20 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C22 C21 C20 114.10(12) . . ?
C22 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
C21 C22 H22A 108.8 . . ?
C21 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 C21 113.67(12) . . ?
C23 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
C22 C23 H23A 108.7 . . ?
C22 C23 H23B 108.7 . . ?
C22 C23 C24 114.11(12) . . ?
H23A C23 H23B 107.6 . . ?
C24 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C23 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
C23 C24 C25 113.30(13) . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1S N1 C5S 116.69(14) . . ?
N1 C1S H1S 118.2 . . ?
N1 C1S C2S 123.57(17) . . ?
C2S C1S H1S 118.2 . . ?
C1S C2S H2S 119.9 . . ?
C1S C2S C3S 120.26(18) . . ?
C3S C2S H2S 119.9 . . ?
C2S C3S C4S 116.91(16) . . ?
C2S C3S C6S 108.6(2) . . ?
C2S C3S C6SA 143.2(3) . . ?
C4S C3S C6S 134.5(2) . . ?
C4S C3S C6SA 99.8(3) . . ?
C3S C4S H4S 120.5 . . ?
C5S C4S C3S 119.00(17) . . ?
C5S C4S H4S 120.5 . . ?
N1 C5S C4S 123.57(16) . . ?
N1 C5S H5S 118.2 . . ?
C4S C5S H5S 118.2 . . ?
C3S C6S H6S 121.6 . . ?
C6S C6S C3S 116.8(3) 3_556 . ?
C6S C6S H6S 121.6 3_556 . ?
C3S C6SA H6SA 120.1 . . ?
C6SA C6SA C3S 119.9(6) 3_556 . ?
C6SA C6SA H6SA 120.1 3_556 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 1.00(2) 1.68(2) 2.6579(17) 165.2(18) 3_876 yes
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
O1 C1 C2 C3 179.50(13) . . . . ?
O2 C1 C2 C3 -0.7(2) . . . . ?
C1 C2 C3 C4 -179.08(13) . . . . ?
C2 C3 C4 C5 178.66(13) . . . . ?
C3 C4 C5 C6 -178.91(12) . . . . ?
C4 C5 C6 C7 176.77(13) . . . . ?
C5 C6 C7 C8 179.63(12) . . . . ?
C6 C7 C8 C9 -177.92(13) . . . . ?
C7 C8 C9 C10 179.83(12) . . . . ?
C13 C14 C15 C16 -174.52(13) . . . . ?
C14 C15 C16 C17 -175.88(12) . . . . ?
C15 C16 C17 C18 -176.54(12) . . . . ?
C16 C17 C18 C19 -179.51(12) . . . . ?
C17 C18 C19 C20 -178.93(12) . . . . ?
C18 C19 C20 C21 -179.24(12) . . . . ?
C19 C20 C21 C22 -178.41(13) . . . . ?
C20 C21 C22 C23 -179.10(12) . . . . ?
C21 C22 C23 C24 -179.70(13) . . . . ?
C22 C23 C24 C25 -177.84(13) . . . . ?
N1 C1S C2S C3S -0.6(3) . . . . ?
C1S N1 C5S C4S -0.4(2) . . . . ?
C1S C2S C3S C4S -0.4(3) . . . . ?
C1S C2S C3S C6S 178.80(17) . . . . ?
C1S C2S C3S C6SA -176.3(3) . . . . ?
C2S C3S C4S C5S 0.9(2) . . . . ?
C2S C3S C6S C6S 174.2(3) . . . 3_556 ?
C2S C3S C6SA C6SA -7.4(8) . . . 3_556 ?
C3S C4S C5S N1 -0.6(2) . . . . ?
C4S C3S C6S C6S -6.8(5) . . . 3_556 ?
C4S C3S C6SA C6SA 176.3(5) . . . 3_556 ?
C5S N1 C1S C2S 1.0(2) . . . . ?
C6S C3S C4S C5S -178.0(2) . . . . ?
C6SA C3S C4S C5S 178.5(2) . . . . ?
_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_instructions_details
;
TITL 18srv481 in P21/c #14
REM reset to P21/c #14
CELL 0.71073 5.4494 8.9235 57.44062 90 92.6433 90
ZERR 4 0.0003 0.0005 0.00311 0 0.0022 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 124 188 4 8
EQIV $1 3-X,2-Y,1-Z
SADI 0.002 C6S C3S C6SA C3S
L.S. 9
PLAN 5
SIZE 0.23 0.31 0.36
TEMP -153.15
HTAB O1 N1_$1
CONF
BOND $h
fmap 2
acta
OMIT -2 57
WGHT 0.053 0.29
FVAR 0.17869
REM
REM
REM
O1 4 2.18354 1.44720 0.55142 11.00000 0.02987 0.02067 0.05206 =
0.00955 0.01472 -0.00169
O2 4 2.41340 1.24568 0.54472 11.00000 0.02527 0.02862 0.03922 =
0.00510 0.01096 0.00095
C1 1 2.23376 1.30197 0.55283 11.00000 0.02111 0.02084 0.02239 =
0.00294 -0.00030 -0.00238
C2 1 2.04144 1.21932 0.56566 11.00000 0.02024 0.01923 0.02577 =
0.00180 0.00523 -0.00166
AFIX 23
H2a 2 2.03403 1.26294 0.58146 11.00000 -1.20000
H2b 2 1.87998 1.23668 0.55749 11.00000 -1.20000
AFIX 0
C3 1 2.08043 1.05200 0.56806 11.00000 0.02032 0.01879 0.02611 =
0.00073 0.00401 -0.00092
AFIX 23
H3a 2 2.08904 1.00725 0.55235 11.00000 -1.20000
H3b 2 2.23949 1.03335 0.57660 11.00000 -1.20000
AFIX 0
C4 1 1.87650 0.97564 0.58089 11.00000 0.02205 0.02022 0.02402 =
0.00074 0.00342 -0.00088
AFIX 23
H4a 2 1.71733 0.99701 0.57255 11.00000 -1.20000
H4b 2 1.87069 1.01940 0.59669 11.00000 -1.20000
AFIX 0
C5 1 1.90732 0.80671 0.58311 11.00000 0.02055 0.01922 0.02826 =
0.00365 0.00483 -0.00032
AFIX 23
H5a 2 2.06489 0.78527 0.59173 11.00000 -1.20000
H5b 2 1.91624 0.76306 0.56732 11.00000 -1.20000
AFIX 0
C6 1 1.70065 0.73075 0.59553 11.00000 0.02333 0.02113 0.02778 =
0.00260 0.00668 -0.00005
AFIX 23
H6a 2 1.69783 0.77003 0.61163 11.00000 -1.20000
H6b 2 1.54205 0.75680 0.58744 11.00000 -1.20000
AFIX 0
C7 1 1.72539 0.56107 0.59647 11.00000 0.02113 0.02044 0.02539 =
0.00315 0.00435 0.00067
AFIX 23
H7a 2 1.72757 0.52212 0.58034 11.00000 -1.20000
H7b 2 1.88485 0.53541 0.60443 11.00000 -1.20000
AFIX 0
C8 1 1.52097 0.48274 0.60899 11.00000 0.02040 0.01956 0.02666 =
0.00256 0.00542 -0.00164
AFIX 23
H8a 2 1.51437 0.52301 0.62501 11.00000 -1.20000
H8b 2 1.36139 0.50393 0.60071 11.00000 -1.20000
AFIX 0
C9 1 1.56129 0.31369 0.61011 11.00000 0.01953 0.02138 0.02582 =
0.00543 0.00586 -0.00222
AFIX 23
H9a 2 1.72228 0.29389 0.61822 11.00000 -1.20000
H9b 2 1.56895 0.27480 0.59402 11.00000 -1.20000
AFIX 0
C10 1 1.37151 0.23070 0.62202 11.00000 0.02270 0.02010 0.02372 =
0.00146 0.00146 0.00313
C11 1 1.21565 0.16268 0.63157 11.00000 0.02168 0.02087 0.02212 =
0.00270 0.00337 0.00095
C12 1 1.03586 0.08417 0.64273 11.00000 0.02234 0.02215 0.02057 =
0.00064 0.00446 0.00088
C13 1 0.87946 0.01540 0.65202 11.00000 0.02440 0.02051 0.02339 =
-0.00052 0.00638 0.00116
C14 1 0.69074 -0.06721 0.66411 11.00000 0.02803 0.02174 0.02662 =
0.00046 0.01258 -0.00362
AFIX 23
H14a 2 0.56645 -0.10486 0.65243 11.00000 -1.20000
H14b 2 0.76795 -0.15517 0.67199 11.00000 -1.20000
AFIX 0
C15 1 0.56120 0.02632 0.68218 11.00000 0.02019 0.02012 0.02088 =
0.00094 0.00559 -0.00197
AFIX 23
H15a 2 0.46928 0.10856 0.67416 11.00000 -1.20000
H15b 2 0.68592 0.07194 0.69307 11.00000 -1.20000
AFIX 0
C16 1 0.38467 -0.06687 0.69594 11.00000 0.02071 0.01831 0.02276 =
0.00142 0.00693 -0.00107
AFIX 23
H16a 2 0.26821 -0.11857 0.68491 11.00000 -1.20000
H16b 2 0.47901 -0.14460 0.70479 11.00000 -1.20000
AFIX 0
C17 1 0.23951 0.02561 0.71286 11.00000 0.02008 0.01757 0.02342 =
0.00043 0.00629 -0.00030
AFIX 23
H17a 2 0.13754 0.09927 0.70389 11.00000 -1.20000
H17b 2 0.35614 0.08224 0.72324 11.00000 -1.20000
AFIX 0
C18 1 0.07373 -0.06788 0.72774 11.00000 0.02061 0.01705 0.02267 =
0.00159 0.00661 0.00051
AFIX 23
H18a 2 -0.04183 -0.12521 0.71734 11.00000 -1.20000
H18b 2 0.17597 -0.14096 0.73680 11.00000 -1.20000
AFIX 0
C19 1 -0.07330 0.02423 0.74453 11.00000 0.01903 0.01782 0.02193 =
0.00027 0.00504 0.00026
AFIX 23
H19a 2 -0.17782 0.09601 0.73543 11.00000 -1.20000
H19b 2 0.04221 0.08306 0.75471 11.00000 -1.20000
AFIX 0
C20 1 -0.23564 -0.06906 0.75974 11.00000 0.02105 0.01766 0.02316 =
0.00018 0.00707 0.00092
AFIX 23
H20a 2 -0.34977 -0.12891 0.74957 11.00000 -1.20000
H20b 2 -0.13096 -0.13988 0.76901 11.00000 -1.20000
AFIX 0
C21 1 -0.38494 0.02373 0.77629 11.00000 0.01997 0.01785 0.02294 =
-0.00016 0.00479 0.00142
AFIX 23
H21a 2 -0.49284 0.09258 0.76698 11.00000 -1.20000
H21b 2 -0.27091 0.08577 0.78614 11.00000 -1.20000
AFIX 0
C22 1 -0.54286 -0.06909 0.79207 11.00000 0.02214 0.01987 0.02533 =
0.00027 0.00872 0.00037
AFIX 23
H22a 2 -0.43490 -0.13675 0.80159 11.00000 -1.20000
H22b 2 -0.65535 -0.13230 0.78225 11.00000 -1.20000
AFIX 0
C23 1 -0.69408 0.02466 0.80825 11.00000 0.02054 0.02007 0.02336 =
0.00159 0.00511 0.00077
AFIX 23
H23a 2 -0.58141 0.08830 0.81798 11.00000 -1.20000
H23b 2 -0.80236 0.09198 0.79870 11.00000 -1.20000
AFIX 0
C24 1 -0.85155 -0.06697 0.82418 11.00000 0.02698 0.02536 0.02820 =
0.00095 0.01015 -0.00077
AFIX 23
H24a 2 -0.96030 -0.13338 0.81452 11.00000 -1.20000
H24b 2 -0.74314 -0.13137 0.83422 11.00000 -1.20000
AFIX 0
C25 1 -1.00876 0.02897 0.83960 11.00000 0.03162 0.03308 0.02861 =
0.00189 0.01306 0.00066
AFIX 137
H25a 2 -1.11806 0.09232 0.82980 11.00000 -1.50000
H25b 2 -1.10717 -0.03611 0.84926 11.00000 -1.50000
H25c 2 -0.90219 0.09240 0.84966 11.00000 -1.50000
AFIX 0
H1 2 2.31856 1.50048 0.54360 11.00000 0.07133
N1 3 0.49572 0.37068 0.46759 11.00000 0.02221 0.01966 0.02863 =
0.00325 0.00362 -0.00178
C1S 1 0.30139 0.40996 0.47915 11.00000 0.02988 0.02971 0.03932 =
-0.00796 0.00438 0.00304
AFIX 43
H1S 2 0.26531 0.51366 0.48051 11.00000 -1.20000
AFIX 0
C2S 1 0.15002 0.30967 0.48923 11.00000 0.02807 0.06953 0.03400 =
0.00071 0.01106 -0.00976
AFIX 43
H2S 2 0.01392 0.34447 0.49746 11.00000 -1.20000
AFIX 0
C3S 1 0.19347 0.15895 0.48752 11.00000 0.03524 0.06162 0.03225 =
0.02580 -0.01687 -0.03103
C4S 1 0.39464 0.11569 0.47513 11.00000 0.05274 0.01743 0.04800 =
0.00864 -0.02798 -0.00744
AFIX 43
H4S 2 0.43198 0.01258 0.47319 11.00000 -1.20000
AFIX 0
C5S 1 0.53891 0.22437 0.46571 11.00000 0.02644 0.02820 0.03157 =
-0.00254 -0.00114 0.00579
AFIX 43
H5S 2 0.67688 0.19342 0.45740 11.00000 -1.20000
AFIX 0
PART 1
C6S 1 -0.00045 0.07524 0.50078 10.60000 0.02202 0.01809 0.02076 =
-0.00350 0.00223 0.00726
AFIX 43
H6S 2 -0.11622 0.12685 0.50970 10.60000 -1.20000
AFIX 0
PART 0
PART 2
C6SA 1 0.09176 0.00495 0.49362 10.40000 0.03112 0.02198 0.02967 =
0.00880 -0.00588 -0.00851
AFIX 43
H6SA 2 0.16567 -0.08321 0.48787 10.40000 -1.20000
AFIX 0
HKLF 4
END
;
#######################################################################
#
# 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_12_2_18srv457
_database_code_depnum_ccdc_archive 'CCDC 2000834'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record
;
2020-05-04 deposited with the CCDC. 2020-07-20 downloaded from the CCDC.
;
_audit_creation_date 2018-11-05
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2017/1
loop_
_audit_author_email
d.s.yufit@durham.ac.uk
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C25 H42 O2, C5 H4 N2'
_chemical_formula_sum 'C30 H46 N2 O2'
_chemical_formula_weight 466.69
_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 triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 5.3544(3)
_cell_length_b 6.8239(4)
_cell_length_c 39.920(2)
_cell_angle_alpha 87.742(4)
_cell_angle_beta 88.869(4)
_cell_angle_gamma 75.291(4)
_cell_volume 1409.64(14)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 5573
_cell_measurement_temperature 120.0
_cell_measurement_theta_max 74.78
_cell_measurement_theta_min 2.22
_shelx_estimated_absorpt_T_max 0.990
_shelx_estimated_absorpt_T_min 0.851
_exptl_absorpt_coefficient_mu 0.522
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.6828
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1364 before and 0.0876 after correction.
The Ratio of minimum to maximum transmission is 0.6828.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.100
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plank
_exptl_crystal_F_000 512
_exptl_crystal_size_max 0.32
_exptl_crystal_size_mid 0.09
_exptl_crystal_size_min 0.02
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.1445
_diffrn_reflns_av_unetI/netI 0.0888
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 48
_diffrn_reflns_limit_l_min -48
_diffrn_reflns_number 33397
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full 67.679
_diffrn_reflns_theta_max 68.990
_diffrn_reflns_theta_min 2.215
_diffrn_ambient_temperature 120.0
_diffrn_detector 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device '3-circle diffractometer'
_diffrn_measurement_device_type ?
_diffrn_measurement_method '\f and \w scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54178
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\mS microsource'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 3097
_reflns_number_total 5160
_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_bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'SAINT v8.38A (Bruker AXS, 2016)'
_computing_data_collection 'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction 'SAINT v8.38A (Bruker AXS, 2016)'
_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 'XM (Sheldrick, 2008)'
_refine_diff_density_max 0.198
_refine_diff_density_min -0.200
_refine_diff_density_rms 0.048
_refine_ls_extinction_coef 0.0019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref 1.090
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 312
_refine_ls_number_reflns 5160
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1569
_refine_ls_R_factor_gt 0.0994
_refine_ls_restrained_S_all 1.090
_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^)+(0.0270P)^2^+2.3500P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1798
_refine_ls_wR_factor_ref 0.2017
_refine_special_details ?
_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,H) groups
2.a Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
C1S(H1S), C2S(H2S), C4S(H4S), C5S(H5S)
2.c Idealised Me refined as rotating group:
C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_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
O1 O -1.4570(5) 2.4096(4) 0.40199(7) 0.0400(7) Uani 1 1 d . . . . .
O2 O -1.6372(5) 2.1512(4) 0.40995(7) 0.0428(8) Uani 1 1 d . . . . .
C1 C -1.4666(7) 2.2207(5) 0.39786(10) 0.0296(9) Uani 1 1 d . . . . .
C2 C -1.2495(7) 2.1067(5) 0.37678(10) 0.0317(9) Uani 1 1 d . . . . .
H2A H -1.085435 2.102159 0.388167 0.038 Uiso 1 1 calc R . . . .
H2B H -1.249051 2.183478 0.355217 0.038 Uiso 1 1 calc R . . . .
C3 C -1.2545(7) 1.8895(5) 0.36921(10) 0.0328(9) Uani 1 1 d . . . . .
H3A H -1.257648 1.810930 0.390535 0.039 Uiso 1 1 calc R . . . .
H3B H -1.413427 1.891695 0.356788 0.039 Uiso 1 1 calc R . . . .
C4 C -1.0187(7) 1.7863(5) 0.34847(10) 0.0324(9) Uani 1 1 d . . . . .
H4A H -1.014304 1.868597 0.327587 0.039 Uiso 1 1 calc R . . . .
H4B H -0.861199 1.783597 0.361236 0.039 Uiso 1 1 calc R . . . .
C5 C -1.0126(7) 1.5712(5) 0.33927(10) 0.0362(10) Uani 1 1 d . . . . .
H5A H -1.169538 1.572773 0.326443 0.043 Uiso 1 1 calc R . . . .
H5B H -1.014854 1.487556 0.360048 0.043 Uiso 1 1 calc R . . . .
C6 C -0.7744(7) 1.4749(5) 0.31842(10) 0.0326(9) Uani 1 1 d . . . . .
H6A H -0.618043 1.466133 0.331810 0.039 Uiso 1 1 calc R . . . .
H6B H -0.766593 1.563430 0.298377 0.039 Uiso 1 1 calc R . . . .
C7 C -0.7732(7) 1.2634(5) 0.30716(10) 0.0339(9) Uani 1 1 d . . . . .
H7A H -0.782403 1.175499 0.327237 0.041 Uiso 1 1 calc R . . . .
H7B H -0.929505 1.272667 0.293725 0.041 Uiso 1 1 calc R . . . .
C8 C -0.5360(7) 1.1650(6) 0.28648(10) 0.0342(9) Uani 1 1 d . . . . .
H8A H -0.379393 1.152398 0.300010 0.041 Uiso 1 1 calc R . . . .
H8B H -0.524653 1.253285 0.266529 0.041 Uiso 1 1 calc R . . . .
C9 C -0.5435(8) 0.9546(6) 0.27506(11) 0.0419(11) Uani 1 1 d . . . . .
H9A H -0.571746 0.871213 0.294947 0.050 Uiso 1 1 calc R . . . .
H9B H -0.692565 0.969636 0.260024 0.050 Uiso 1 1 calc R . . . .
C10 C -0.3085(8) 0.8467(6) 0.25751(10) 0.0363(10) Uani 1 1 d . . . . .
C11 C -0.1146(7) 0.7598(6) 0.24379(10) 0.0346(9) Uani 1 1 d . . . . .
C12 C 0.1081(7) 0.6586(6) 0.22772(10) 0.0341(9) Uani 1 1 d . . . . .
C13 C 0.3047(8) 0.5710(6) 0.21418(10) 0.0381(10) Uani 1 1 d . . . . .
C14 C 0.5427(7) 0.4628(6) 0.19764(11) 0.0404(10) Uani 1 1 d . . . . .
H14A H 0.686897 0.443462 0.213586 0.048 Uiso 1 1 calc R . . . .
H14B H 0.579275 0.547773 0.178423 0.048 Uiso 1 1 calc R . . . .
C15 C 0.5345(7) 0.2554(6) 0.18494(10) 0.0346(9) Uani 1 1 d . . . . .
H15A H 0.505416 0.167337 0.204149 0.042 Uiso 1 1 calc R . . . .
H15B H 0.387947 0.272902 0.169404 0.042 Uiso 1 1 calc R . . . .
C16 C 0.7852(7) 0.1525(6) 0.16684(11) 0.0383(10) Uani 1 1 d . . . . .
H16A H 0.814256 0.242133 0.147842 0.046 Uiso 1 1 calc R . . . .
H16B H 0.930845 0.135548 0.182493 0.046 Uiso 1 1 calc R . . . .
C17 C 0.7849(7) -0.0536(5) 0.15359(10) 0.0339(9) Uani 1 1 d . . . . .
H17A H 0.764987 -0.145610 0.172687 0.041 Uiso 1 1 calc R . . . .
H17B H 0.634515 -0.037978 0.138774 0.041 Uiso 1 1 calc R . . . .
C18 C 1.0293(7) -0.1493(6) 0.13424(11) 0.0376(10) Uani 1 1 d . . . . .
H18A H 1.179955 -0.158672 0.148761 0.045 Uiso 1 1 calc R . . . .
H18B H 1.044865 -0.059695 0.114615 0.045 Uiso 1 1 calc R . . . .
C19 C 1.0376(7) -0.3595(5) 0.12211(10) 0.0340(9) Uani 1 1 d . . . . .
H19A H 0.881671 -0.351329 0.108667 0.041 Uiso 1 1 calc R . . . .
H19B H 1.031759 -0.450852 0.141836 0.041 Uiso 1 1 calc R . . . .
C20 C 1.2756(7) -0.4519(6) 0.10105(11) 0.0380(10) Uani 1 1 d . . . . .
H20A H 1.431497 -0.458006 0.114382 0.046 Uiso 1 1 calc R . . . .
H20B H 1.280005 -0.361360 0.081166 0.046 Uiso 1 1 calc R . . . .
C21 C 1.2872(7) -0.6636(6) 0.08922(11) 0.0375(10) Uani 1 1 d . . . . .
H21A H 1.280312 -0.754104 0.109028 0.045 Uiso 1 1 calc R . . . .
H21B H 1.133346 -0.657504 0.075473 0.045 Uiso 1 1 calc R . . . .
C22 C 1.5281(7) -0.7542(6) 0.06877(10) 0.0373(10) Uani 1 1 d . . . . .
H22A H 1.681783 -0.757726 0.082408 0.045 Uiso 1 1 calc R . . . .
H22B H 1.533295 -0.664526 0.048802 0.045 Uiso 1 1 calc R . . . .
C23 C 1.5445(7) -0.9685(6) 0.05720(10) 0.0364(9) Uani 1 1 d . . . . .
H23A H 1.544997 -1.059632 0.077136 0.044 Uiso 1 1 calc R . . . .
H23B H 1.389116 -0.966253 0.044005 0.044 Uiso 1 1 calc R . . . .
C24 C 1.7840(8) -1.0533(6) 0.03600(11) 0.0439(11) Uani 1 1 d . . . . .
H24A H 1.939153 -1.053526 0.049093 0.053 Uiso 1 1 calc R . . . .
H24B H 1.782091 -0.963066 0.015921 0.053 Uiso 1 1 calc R . . . .
C25 C 1.8036(9) -1.2685(6) 0.02476(11) 0.0514(12) Uani 1 1 d . . . . .
H25A H 1.960990 -1.314806 0.011271 0.077 Uiso 1 1 calc GR . . . .
H25B H 1.652664 -1.268988 0.011297 0.077 Uiso 1 1 calc GR . . . .
H25C H 1.809630 -1.359504 0.044504 0.077 Uiso 1 1 calc GR . . . .
H1 H -1.614(9) 2.478(7) 0.4163(12) 0.077 Uiso 1 1 d R . . . .
N1 N 0.5109(6) 0.9082(4) 0.49756(8) 0.0354(8) Uani 1 1 d . . . . .
N2 N 1.1414(6) 0.6175(4) 0.43775(8) 0.0319(8) Uani 1 1 d . . . . .
C1S C 1.1052(7) 0.8142(6) 0.44419(10) 0.0332(9) Uani 1 1 d . . . . .
H1S H 1.225582 0.883740 0.435187 0.040 Uiso 1 1 calc R . . . .
C2S C 0.9014(7) 0.9204(6) 0.46327(10) 0.0345(9) Uani 1 1 d . . . . .
H2S H 0.881009 1.060156 0.467088 0.041 Uiso 1 1 calc R . . . .
C3S C 0.7271(7) 0.8186(6) 0.47672(10) 0.0315(9) Uani 1 1 d . . . . .
C4S C 0.7597(7) 0.6174(6) 0.46945(10) 0.0359(10) Uani 1 1 d . . . . .
H4S H 0.639377 0.545357 0.477588 0.043 Uiso 1 1 calc R . . . .
C5S C 0.9694(7) 0.5223(6) 0.45019(10) 0.0360(10) Uani 1 1 d . . . . .
H5S H 0.991993 0.383316 0.445616 0.043 Uiso 1 1 calc R . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0350(16) 0.0261(14) 0.060(2) -0.0178(13) 0.0161(14) -0.0089(12)
O2 0.0319(15) 0.0333(16) 0.064(2) -0.0106(14) 0.0175(14) -0.0096(13)
C1 0.0204(18) 0.028(2) 0.038(2) -0.0051(16) 0.0013(16) -0.0029(16)
C2 0.027(2) 0.027(2) 0.040(2) -0.0077(17) 0.0060(17) -0.0047(17)
C3 0.029(2) 0.030(2) 0.042(2) -0.0089(17) 0.0086(18) -0.0115(17)
C4 0.026(2) 0.030(2) 0.040(2) -0.0047(17) 0.0014(17) -0.0037(17)
C5 0.030(2) 0.028(2) 0.049(3) -0.0073(18) 0.0062(19) -0.0036(18)
C6 0.030(2) 0.027(2) 0.040(2) -0.0054(17) 0.0045(18) -0.0047(17)
C7 0.026(2) 0.030(2) 0.044(3) -0.0093(17) 0.0082(18) -0.0051(17)
C8 0.028(2) 0.032(2) 0.041(2) -0.0058(17) 0.0032(18) -0.0052(17)
C9 0.034(2) 0.040(2) 0.053(3) -0.017(2) 0.009(2) -0.0091(19)
C10 0.037(2) 0.032(2) 0.041(2) -0.0122(18) 0.0029(19) -0.0084(19)
C11 0.034(2) 0.027(2) 0.042(2) -0.0080(17) 0.0006(19) -0.0039(18)
C12 0.031(2) 0.030(2) 0.040(2) -0.0080(17) -0.0022(18) -0.0044(18)
C13 0.034(2) 0.031(2) 0.048(3) -0.0138(18) 0.004(2) -0.0046(19)
C14 0.032(2) 0.034(2) 0.055(3) -0.0152(19) 0.009(2) -0.0056(19)
C15 0.030(2) 0.032(2) 0.042(2) -0.0055(17) 0.0032(18) -0.0071(17)
C16 0.031(2) 0.034(2) 0.049(3) -0.0105(19) 0.0060(19) -0.0070(19)
C17 0.029(2) 0.029(2) 0.042(2) -0.0066(17) 0.0035(18) -0.0047(17)
C18 0.029(2) 0.029(2) 0.053(3) -0.0083(18) 0.0091(19) -0.0050(18)
C19 0.030(2) 0.031(2) 0.040(2) -0.0056(17) 0.0029(18) -0.0049(17)
C20 0.030(2) 0.032(2) 0.051(3) -0.0090(19) 0.0086(19) -0.0046(18)
C21 0.031(2) 0.030(2) 0.050(3) -0.0090(18) 0.0069(19) -0.0049(18)
C22 0.033(2) 0.033(2) 0.045(3) -0.0109(18) 0.0078(19) -0.0062(18)
C23 0.036(2) 0.032(2) 0.040(2) -0.0057(18) 0.0015(19) -0.0051(18)
C24 0.042(2) 0.034(2) 0.052(3) -0.011(2) 0.008(2) -0.003(2)
C25 0.060(3) 0.032(2) 0.058(3) -0.013(2) 0.006(2) -0.002(2)
N1 0.0291(17) 0.0321(17) 0.041(2) -0.0092(15) 0.0030(15) 0.0006(16)
N2 0.0248(16) 0.0283(17) 0.040(2) -0.0060(14) 0.0012(14) -0.0005(14)
C1S 0.030(2) 0.031(2) 0.039(2) -0.0030(17) 0.0017(17) -0.0076(17)
C2S 0.029(2) 0.032(2) 0.039(2) -0.0096(17) 0.0028(18) -0.0015(17)
C3S 0.0222(19) 0.036(2) 0.032(2) -0.0054(17) 0.0004(16) 0.0011(16)
C4S 0.033(2) 0.031(2) 0.042(3) -0.0074(18) 0.0093(19) -0.0046(18)
C5S 0.032(2) 0.027(2) 0.047(3) -0.0062(18) 0.0021(19) -0.0025(18)
_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
O1 C1 1.320(4) . ?
O1 H1 1.03(5) . ?
O2 C1 1.215(4) . ?
C1 C2 1.489(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.532(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.526(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.519(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.525(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.527(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.522(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.534(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.467(5) . ?
C10 C11 1.192(5) . ?
C11 C12 1.377(5) . ?
C12 C13 1.200(5) . ?
C13 C14 1.460(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.533(5) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.530(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.522(5) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.517(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.522(5) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.523(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.523(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.518(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.532(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.521(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.530(5) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N1 N1 1.251(6) 2_676 ?
N1 C3S 1.432(4) . ?
N2 C1S 1.341(4) . ?
N2 C5S 1.333(5) . ?
C1S H1S 0.9500 . ?
C1S C2S 1.380(5) . ?
C2S H2S 0.9500 . ?
C2S C3S 1.386(5) . ?
C3S C4S 1.381(5) . ?
C4S H4S 0.9500 . ?
C4S C5S 1.382(5) . ?
C5S H5S 0.9500 . ?
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
C1 O1 H1 108(3) . . ?
O1 C1 C2 112.6(3) . . ?
O2 C1 O1 122.6(3) . . ?
O2 C1 C2 124.7(3) . . ?
C1 C2 H2A 108.3 . . ?
C1 C2 H2B 108.3 . . ?
C1 C2 C3 115.9(3) . . ?
H2A C2 H2B 107.4 . . ?
C3 C2 H2A 108.3 . . ?
C3 C2 H2B 108.3 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.1(3) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.2(3) . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
C4 C5 C6 112.3(3) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
C5 C6 C7 113.0(3) . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C6 C7 H7A 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 C6 113.6(3) . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C7 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C7 C8 C9 112.2(3) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 C8 114.0(3) . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C11 C10 C9 178.6(4) . . ?
C10 C11 C12 179.4(5) . . ?
C13 C12 C11 178.8(4) . . ?
C12 C13 C14 179.4(4) . . ?
C13 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C13 C14 C15 114.1(3) . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C16 C15 C14 111.7(3) . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C15 C16 H16A 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C15 113.5(3) . . ?
C17 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C16 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 C16 113.0(3) . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C17 C18 C19 113.7(3) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19A 108.7 . . ?
C18 C19 H19B 108.7 . . ?
C18 C19 C20 114.0(3) . . ?
H19A C19 H19B 107.6 . . ?
C20 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C19 C20 H20A 108.7 . . ?
C19 C20 H20B 108.7 . . ?
C19 C20 C21 114.3(3) . . ?
H20A C20 H20B 107.6 . . ?
C21 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C20 C21 H21A 108.9 . . ?
C20 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 C20 113.4(3) . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C21 C22 H22A 108.8 . . ?
C21 C22 H22B 108.8 . . ?
C21 C22 C23 114.0(3) . . ?
H22A C22 H22B 107.6 . . ?
C23 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
C22 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 C22 112.9(3) . . ?
C24 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C23 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
C23 C24 C25 113.2(4) . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 N1 C3S 113.6(4) 2_676 . ?
C5S N2 C1S 117.8(3) . . ?
N2 C1S H1S 118.4 . . ?
N2 C1S C2S 123.1(4) . . ?
C2S C1S H1S 118.4 . . ?
C1S C2S H2S 120.7 . . ?
C1S C2S C3S 118.5(4) . . ?
C3S C2S H2S 120.7 . . ?
C2S C3S N1 124.5(3) . . ?
C4S C3S N1 116.9(3) . . ?
C4S C3S C2S 118.6(4) . . ?
C3S C4S H4S 120.4 . . ?
C3S C4S C5S 119.2(4) . . ?
C5S C4S H4S 120.4 . . ?
N2 C5S C4S 122.7(4) . . ?
N2 C5S H5S 118.6 . . ?
C4S C5S H5S 118.6 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N2 1.03(5) 1.66(5) 2.677(4) 173(4) 1_275 yes
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
O1 C1 C2 C3 -176.9(3) . . . . ?
O2 C1 C2 C3 2.5(6) . . . . ?
C1 C2 C3 C4 -178.2(4) . . . . ?
C2 C3 C4 C5 -178.7(3) . . . . ?
C3 C4 C5 C6 179.7(4) . . . . ?
C4 C5 C6 C7 -176.5(3) . . . . ?
C5 C6 C7 C8 -179.7(4) . . . . ?
C6 C7 C8 C9 -178.9(4) . . . . ?
C7 C8 C9 C10 -175.0(4) . . . . ?
C13 C14 C15 C16 178.1(4) . . . . ?
C14 C15 C16 C17 -179.6(4) . . . . ?
C15 C16 C17 C18 177.2(4) . . . . ?
C16 C17 C18 C19 177.5(4) . . . . ?
C17 C18 C19 C20 176.9(4) . . . . ?
C18 C19 C20 C21 179.2(4) . . . . ?
C19 C20 C21 C22 -179.0(4) . . . . ?
C20 C21 C22 C23 179.0(4) . . . . ?
C21 C22 C23 C24 178.4(4) . . . . ?
C22 C23 C24 C25 179.2(4) . . . . ?
N1 N1 C3S C2S 0.9(6) 2_676 . . . ?
N1 N1 C3S C4S -178.3(4) 2_676 . . . ?
N1 C3S C4S C5S -178.3(4) . . . . ?
N2 C1S C2S C3S 0.7(6) . . . . ?
C1S N2 C5S C4S -0.6(6) . . . . ?
C1S C2S C3S N1 178.5(4) . . . . ?
C1S C2S C3S C4S -2.3(6) . . . . ?
C2S C3S C4S C5S 2.5(6) . . . . ?
C3S C4S C5S N2 -1.0(6) . . . . ?
C5S N2 C1S C2S 0.8(6) . . . . ?
_olex2_submission_special_instructions 'No special instructions were received'
_iucr_refine_instructions_details
;
TITL 18srv457 in P-1 #2
REM Best SHELXD solution FINAL CC 88.78
REM Fragments: 27 7
REM reset to P-1 #2
CELL 1.54178 5.3544 6.8239 39.9203 87.7423 88.8694 75.2915
ZERR 2 0.0003 0.0004 0.0024 0.0037 0.0038 0.0041
LATT 1
SFAC C H N O
UNIT 60 92 4 4
EQIV $1 -3+X,2+Y,+Z
L.S. 9 0 0
PLAN 5
SIZE 0.02 0.09 0.32
TEMP -153.15
HTAB O1 N2_$1
BOND $h
CONF
fmap 2 53
acta
EXTI 0.0019
OMIT -2 138
OMIT -2 5 1
OMIT 4 6 3
WGHT 0.027 2.35
FVAR 0.16033
REM
REM
REM
O1 4 -1.45699 2.40961 0.40199 11.00000 0.03502 0.02612 0.06020 =
-0.01782 0.01613 -0.00889
O2 4 -1.63721 2.15118 0.40995 11.00000 0.03191 0.03327 0.06382 =
-0.01063 0.01748 -0.00961
C1 1 -1.46659 2.22070 0.39786 11.00000 0.02044 0.02832 0.03840 =
-0.00513 0.00134 -0.00294
C2 1 -1.24951 2.10675 0.37678 11.00000 0.02652 0.02723 0.04046 =
-0.00767 0.00601 -0.00469
AFIX 23
H2A 2 -1.08543 2.10216 0.38817 11.00000 -1.20000
H2B 2 -1.24905 2.18348 0.35522 11.00000 -1.20000
AFIX 0
C3 1 -1.25448 1.88946 0.36921 11.00000 0.02858 0.03014 0.04207 =
-0.00891 0.00864 -0.01149
AFIX 23
H3A 2 -1.25765 1.81093 0.39054 11.00000 -1.20000
H3B 2 -1.41343 1.89169 0.35679 11.00000 -1.20000
AFIX 0
C4 1 -1.01875 1.78628 0.34847 11.00000 0.02587 0.02998 0.03985 =
-0.00472 0.00141 -0.00369
AFIX 23
H4A 2 -1.01430 1.86860 0.32759 11.00000 -1.20000
H4B 2 -0.86120 1.78360 0.36124 11.00000 -1.20000
AFIX 0
C5 1 -1.01261 1.57121 0.33927 11.00000 0.02950 0.02776 0.04945 =
-0.00733 0.00624 -0.00361
AFIX 23
H5A 2 -1.16954 1.57277 0.32644 11.00000 -1.20000
H5B 2 -1.01485 1.48756 0.36005 11.00000 -1.20000
AFIX 0
C6 1 -0.77443 1.47494 0.31842 11.00000 0.03037 0.02680 0.03952 =
-0.00542 0.00449 -0.00469
AFIX 23
H6A 2 -0.61804 1.46613 0.33181 11.00000 -1.20000
H6B 2 -0.76659 1.56343 0.29838 11.00000 -1.20000
AFIX 0
C7 1 -0.77325 1.26344 0.30716 11.00000 0.02645 0.03028 0.04407 =
-0.00934 0.00815 -0.00515
AFIX 23
H7A 2 -0.78240 1.17550 0.32724 11.00000 -1.20000
H7B 2 -0.92951 1.27267 0.29373 11.00000 -1.20000
AFIX 0
C8 1 -0.53602 1.16498 0.28648 11.00000 0.02825 0.03215 0.04096 =
-0.00577 0.00319 -0.00517
AFIX 23
H8A 2 -0.37939 1.15240 0.30001 11.00000 -1.20000
H8B 2 -0.52465 1.25329 0.26653 11.00000 -1.20000
AFIX 0
C9 1 -0.54352 0.95459 0.27506 11.00000 0.03419 0.03959 0.05256 =
-0.01727 0.00907 -0.00914
AFIX 23
H9A 2 -0.57175 0.87121 0.29495 11.00000 -1.20000
H9B 2 -0.69256 0.96964 0.26002 11.00000 -1.20000
AFIX 0
C10 1 -0.30845 0.84668 0.25750 11.00000 0.03656 0.03173 0.04128 =
-0.01220 0.00288 -0.00845
C11 1 -0.11457 0.75975 0.24379 11.00000 0.03358 0.02701 0.04157 =
-0.00797 0.00062 -0.00385
C12 1 0.10810 0.65856 0.22772 11.00000 0.03076 0.03037 0.04001 =
-0.00803 -0.00217 -0.00442
C13 1 0.30474 0.57101 0.21418 11.00000 0.03444 0.03075 0.04812 =
-0.01384 0.00382 -0.00462
C14 1 0.54267 0.46277 0.19764 11.00000 0.03152 0.03378 0.05521 =
-0.01517 0.00877 -0.00560
AFIX 23
H14A 2 0.68690 0.44346 0.21359 11.00000 -1.20000
H14B 2 0.57927 0.54777 0.17842 11.00000 -1.20000
AFIX 0
C15 1 0.53448 0.25541 0.18494 11.00000 0.02960 0.03194 0.04210 =
-0.00547 0.00321 -0.00713
AFIX 23
H15A 2 0.50542 0.16734 0.20415 11.00000 -1.20000
H15B 2 0.38795 0.27290 0.16940 11.00000 -1.20000
AFIX 0
C16 1 0.78518 0.15254 0.16684 11.00000 0.03147 0.03431 0.04890 =
-0.01054 0.00603 -0.00701
AFIX 23
H16A 2 0.81426 0.24213 0.14784 11.00000 -1.20000
H16B 2 0.93085 0.13555 0.18249 11.00000 -1.20000
AFIX 0
C17 1 0.78494 -0.05359 0.15359 11.00000 0.02945 0.02922 0.04173 =
-0.00658 0.00354 -0.00468
AFIX 23
H17A 2 0.76499 -0.14561 0.17269 11.00000 -1.20000
H17B 2 0.63452 -0.03798 0.13877 11.00000 -1.20000
AFIX 0
C18 1 1.02929 -0.14928 0.13424 11.00000 0.02942 0.02937 0.05297 =
-0.00832 0.00906 -0.00504
AFIX 23
H18A 2 1.17996 -0.15867 0.14876 11.00000 -1.20000
H18B 2 1.04486 -0.05969 0.11461 11.00000 -1.20000
AFIX 0
C19 1 1.03764 -0.35951 0.12211 11.00000 0.03003 0.03099 0.03970 =
-0.00556 0.00295 -0.00494
AFIX 23
H19A 2 0.88167 -0.35133 0.10867 11.00000 -1.20000
H19B 2 1.03176 -0.45085 0.14184 11.00000 -1.20000
AFIX 0
C20 1 1.27560 -0.45190 0.10105 11.00000 0.02962 0.03210 0.05076 =
-0.00901 0.00859 -0.00462
AFIX 23
H20A 2 1.43150 -0.45801 0.11438 11.00000 -1.20000
H20B 2 1.28001 -0.36136 0.08117 11.00000 -1.20000
AFIX 0
C21 1 1.28720 -0.66361 0.08922 11.00000 0.03079 0.03020 0.05015 =
-0.00901 0.00691 -0.00486
AFIX 23
H21A 2 1.28031 -0.75410 0.10903 11.00000 -1.20000
H21B 2 1.13335 -0.65750 0.07547 11.00000 -1.20000
AFIX 0
C22 1 1.52814 -0.75418 0.06878 11.00000 0.03294 0.03309 0.04513 =
-0.01088 0.00781 -0.00623
AFIX 23
H22A 2 1.68178 -0.75773 0.08241 11.00000 -1.20000
H22B 2 1.53329 -0.66453 0.04880 11.00000 -1.20000
AFIX 0
C23 1 1.54450 -0.96852 0.05720 11.00000 0.03573 0.03167 0.04012 =
-0.00572 0.00151 -0.00512
AFIX 23
H23A 2 1.54500 -1.05963 0.07714 11.00000 -1.20000
H23B 2 1.38912 -0.96625 0.04401 11.00000 -1.20000
AFIX 0
C24 1 1.78397 -1.05331 0.03600 11.00000 0.04232 0.03422 0.05217 =
-0.01082 0.00817 -0.00343
AFIX 23
H24A 2 1.93915 -1.05353 0.04909 11.00000 -1.20000
H24B 2 1.78209 -0.96307 0.01592 11.00000 -1.20000
AFIX 0
C25 1 1.80357 -1.26848 0.02476 11.00000 0.05999 0.03180 0.05783 =
-0.01279 0.00586 -0.00226
AFIX 137
H25A 2 1.96099 -1.31481 0.01127 11.00000 -1.50000
H25B 2 1.65266 -1.26899 0.01130 11.00000 -1.50000
H25C 2 1.80963 -1.35950 0.04450 11.00000 -1.50000
AFIX 0
H1 2 -1.61382 2.47837 0.41626 11.00000 -1.50000
N1 3 0.51091 0.90824 0.49756 11.00000 0.02906 0.03214 0.04091 =
-0.00925 0.00304 0.00057
N2 3 1.14136 0.61750 0.43775 11.00000 0.02476 0.02830 0.03960 =
-0.00599 0.00124 -0.00047
C1S 1 1.10521 0.81419 0.44419 11.00000 0.02951 0.03104 0.03903 =
-0.00296 0.00169 -0.00760
AFIX 43
H1S 2 1.22558 0.88374 0.43519 11.00000 -1.20000
AFIX 0
C2S 1 0.90140 0.92041 0.46326 11.00000 0.02926 0.03182 0.03949 =
-0.00957 0.00277 -0.00148
AFIX 43
H2S 2 0.88101 1.06016 0.46709 11.00000 -1.20000
AFIX 0
C3S 1 0.72714 0.81862 0.47672 11.00000 0.02222 0.03561 0.03231 =
-0.00537 0.00044 0.00112
C4S 1 0.75968 0.61744 0.46945 11.00000 0.03262 0.03094 0.04230 =
-0.00736 0.00928 -0.00463
AFIX 43
H4S 2 0.63938 0.54536 0.47759 11.00000 -1.20000
AFIX 0
C5S 1 0.96941 0.52234 0.45019 11.00000 0.03169 0.02669 0.04737 =
-0.00622 0.00208 -0.00253
AFIX 43
H5S 2 0.99199 0.38332 0.44562 11.00000 -1.20000
AFIX 0
HKLF 4
END
;
#######################################################################
#
# 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_12_7_19srv360
_database_code_depnum_ccdc_archive 'CCDC 2000835'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record
;
2020-05-04 deposited with the CCDC. 2020-07-20 downloaded from the CCDC.
;
_audit_creation_date 2019-12-03
_audit_creation_method
;
Olex2 1.3-beta
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number 2017/1
loop_
_audit_author_email
d.s.yufit@durham.ac.uk
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety '2(C25 H41.5 O2), C4 H12 N'
_chemical_formula_sum 'C54 H95 N O4'
_chemical_formula_weight 822.30
_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 0.0033 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'
_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 13
_space_group_name_H-M_alt 'P 1 2/n 1'
_space_group_name_Hall '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'
_cell_length_a 9.5968(6)
_cell_length_b 4.6441(3)
_cell_length_c 57.520(4)
_cell_angle_alpha 90
_cell_angle_beta 92.590(2)
_cell_angle_gamma 90
_cell_volume 2561.0(3)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 9937
_cell_measurement_temperature 120.0
_cell_measurement_theta_max 28.93
_cell_measurement_theta_min 2.17
_shelx_estimated_absorpt_T_max 0.994
_shelx_estimated_absorpt_T_min 0.968
_exptl_absorpt_coefficient_mu 0.065
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.8171
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1545 before and 0.0602 after correction.
The Ratio of minimum to maximum transmission is 0.8171.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_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 1.066
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plank
_exptl_crystal_F_000 916
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.1
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0502
_diffrn_reflns_av_unetI/netI 0.0501
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 5
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_l_max 75
_diffrn_reflns_limit_l_min -72
_diffrn_reflns_number 30938
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.998
_diffrn_reflns_theta_min 2.138
_diffrn_ambient_temperature 120.0
_diffrn_detector 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device '3-circle diffractometer'
_diffrn_measurement_device_type D8Venture
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_current 1.0
_diffrn_source_power 0.05
_diffrn_source_type 'Incoatec I\mS microsource'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 4009
_reflns_number_total 6051
_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_bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection 'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction 'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics 'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 1.3-beta (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max 0.208
_refine_diff_density_min -0.180
_refine_diff_density_rms 0.039
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.049
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 274
_refine_ls_number_reflns 6051
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0945
_refine_ls_R_factor_gt 0.0561
_refine_ls_restrained_S_all 1.049
_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^)+(0.0380P)^2^+1.4200P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1217
_refine_ls_wR_factor_ref 0.1361
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
2. Others
Fixed Sof: H2(0.5)
3.a Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C26(H26A,H26B)
3.b Idealised Me refined as rotating group:
C25(H25A,H25B,H25C), C27(H27A,H27B,H27C)
3.c Idealised tetrahedral OH refined as rotating group:
O2(H2)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_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
O1 O -0.54670(11) 0.3340(3) 0.27315(2) 0.0334(3) Uani 1 1 d . . . . .
O2 O -0.37529(11) 0.1611(3) 0.25298(2) 0.0308(3) Uani 1 1 d . . . . .
H2 H -0.288039 0.174991 0.252909 0.046 Uiso 0.5 1 calc R U P A -1
C1 C -0.42126(16) 0.3223(4) 0.26912(3) 0.0251(3) Uani 1 1 d . . . . .
C2 C -0.31850(16) 0.4966(4) 0.28398(3) 0.0263(4) Uani 1 1 d . . . . .
H2A H -0.368359 0.655640 0.291486 0.032 Uiso 1 1 calc R U . . .
H2B H -0.248316 0.582435 0.273955 0.032 Uiso 1 1 calc R U . . .
C3 C -0.24449(15) 0.3112(3) 0.30272(3) 0.0236(3) Uani 1 1 d . . . . .
H3A H -0.315109 0.211967 0.311854 0.028 Uiso 1 1 calc R U . . .
H3B H -0.188262 0.162210 0.295163 0.028 Uiso 1 1 calc R U . . .
C4 C -0.14969(16) 0.4895(4) 0.31909(3) 0.0266(4) Uani 1 1 d . . . . .
H4A H -0.079440 0.588005 0.309826 0.032 Uiso 1 1 calc R U . . .
H4B H -0.206379 0.639767 0.326383 0.032 Uiso 1 1 calc R U . . .
C5 C -0.07427(16) 0.3157(4) 0.33819(3) 0.0245(3) Uani 1 1 d . . . . .
H5A H -0.015134 0.168921 0.330969 0.029 Uiso 1 1 calc R U . . .
H5B H -0.144062 0.213302 0.347285 0.029 Uiso 1 1 calc R U . . .
C6 C 0.01680(16) 0.5012(4) 0.35463(3) 0.0263(4) Uani 1 1 d . . . . .
H6A H 0.082347 0.613048 0.345363 0.032 Uiso 1 1 calc R U . . .
H6B H -0.043443 0.640136 0.362526 0.032 Uiso 1 1 calc R U . . .
C7 C 0.10003(16) 0.3296(4) 0.37299(3) 0.0262(3) Uani 1 1 d . . . . .
H7A H 0.163935 0.197477 0.365173 0.031 Uiso 1 1 calc R U . . .
H7B H 0.035115 0.210948 0.381850 0.031 Uiso 1 1 calc R U . . .
C8 C 0.18491(16) 0.5204(4) 0.38990(3) 0.0260(3) Uani 1 1 d . . . . .
H8A H 0.120596 0.645862 0.398284 0.031 Uiso 1 1 calc R U . . .
H8B H 0.246469 0.645993 0.380972 0.031 Uiso 1 1 calc R U . . .
C9 C 0.27412(17) 0.3475(4) 0.40764(3) 0.0291(4) Uani 1 1 d . . . . .
H9A H 0.212698 0.221660 0.416569 0.035 Uiso 1 1 calc R U . . .
H9B H 0.338757 0.222525 0.399280 0.035 Uiso 1 1 calc R U . . .
C10 C 0.35510(16) 0.5329(4) 0.42386(3) 0.0285(4) Uani 1 1 d . . . . .
C11 C 0.42073(16) 0.6922(4) 0.43660(3) 0.0283(4) Uani 1 1 d . . . . .
C12 C 0.49622(17) 0.8725(4) 0.45138(3) 0.0291(4) Uani 1 1 d . . . . .
C13 C 0.56135(16) 1.0328(4) 0.46412(3) 0.0286(4) Uani 1 1 d . . . . .
C14 C 0.64129(17) 1.2218(4) 0.48011(3) 0.0297(4) Uani 1 1 d . . . . .
H14A H 0.575752 1.344329 0.488501 0.036 Uiso 1 1 calc R U . . .
H14B H 0.700469 1.350059 0.470979 0.036 Uiso 1 1 calc R U . . .
C15 C 0.73404(16) 1.0572(4) 0.49788(3) 0.0256(3) Uani 1 1 d . . . . .
H15A H 0.674786 0.932378 0.507289 0.031 Uiso 1 1 calc R U . . .
H15B H 0.798316 0.931379 0.489515 0.031 Uiso 1 1 calc R U . . .
C16 C 0.81886(16) 1.2557(4) 0.51401(3) 0.0260(4) Uani 1 1 d . . . . .
H16A H 0.754635 1.386554 0.521897 0.031 Uiso 1 1 calc R U . . .
H16B H 0.880534 1.375490 0.504621 0.031 Uiso 1 1 calc R U . . .
C17 C 0.90755(16) 1.0943(4) 0.53234(3) 0.0258(4) Uani 1 1 d . . . . .
H17A H 0.845389 0.982461 0.542231 0.031 Uiso 1 1 calc R U . . .
H17B H 0.968124 0.955953 0.524452 0.031 Uiso 1 1 calc R U . . .
C18 C 0.99849(16) 1.2911(4) 0.54778(3) 0.0259(4) Uani 1 1 d . . . . .
H18A H 0.937604 1.425826 0.555981 0.031 Uiso 1 1 calc R U . . .
H18B H 1.058555 1.407047 0.537821 0.031 Uiso 1 1 calc R U . . .
C19 C 1.09072(16) 1.1309(4) 0.56575(3) 0.0262(4) Uani 1 1 d . . . . .
H19A H 1.030664 1.013522 0.575608 0.031 Uiso 1 1 calc R U . . .
H19B H 1.152162 0.997487 0.557537 0.031 Uiso 1 1 calc R U . . .
C20 C 1.18076(16) 1.3271(4) 0.58136(3) 0.0262(3) Uani 1 1 d . . . . .
H20A H 1.119601 1.464838 0.589186 0.031 Uiso 1 1 calc R U . . .
H20B H 1.243160 1.439741 0.571563 0.031 Uiso 1 1 calc R U . . .
C21 C 1.26907(16) 1.1667(4) 0.59977(3) 0.0267(3) Uani 1 1 d . . . . .
H21A H 1.335260 1.039849 0.591934 0.032 Uiso 1 1 calc R U . . .
H21B H 1.207393 1.042741 0.608813 0.032 Uiso 1 1 calc R U . . .
C22 C 1.35098(16) 1.3644(4) 0.61649(3) 0.0260(3) Uani 1 1 d . . . . .
H22A H 1.284698 1.490109 0.624431 0.031 Uiso 1 1 calc R U . . .
H22B H 1.411973 1.489716 0.607432 0.031 Uiso 1 1 calc R U . . .
C23 C 1.44047(16) 1.2042(4) 0.63481(3) 0.0276(4) Uani 1 1 d . . . . .
H23A H 1.380304 1.070433 0.643243 0.033 Uiso 1 1 calc R U . . .
H23B H 1.510389 1.087265 0.626888 0.033 Uiso 1 1 calc R U . . .
C24 C 1.51596(17) 1.4011(4) 0.65236(3) 0.0294(4) Uani 1 1 d . . . . .
H24A H 1.446106 1.516354 0.660434 0.035 Uiso 1 1 calc R U . . .
H24B H 1.575487 1.536203 0.643933 0.035 Uiso 1 1 calc R U . . .
C25 C 1.60636(19) 1.2388(4) 0.67043(3) 0.0387(4) Uani 1 1 d . . . . .
H25A H 1.679378 1.133106 0.662652 0.058 Uiso 1 1 calc R U . . .
H25B H 1.548401 1.102871 0.678740 0.058 Uiso 1 1 calc R U . . .
H25C H 1.649457 1.376001 0.681522 0.058 Uiso 1 1 calc R U . . .
N1 N -0.750000 0.0187(4) 0.250000 0.0237(4) Uani 1 2 d S T P . .
C26 C -0.69341(17) -0.1567(4) 0.23087(3) 0.0298(4) Uani 1 1 d . . . . .
H26A H -0.766799 -0.287443 0.224389 0.036 Uiso 1 1 calc R U . . .
H26B H -0.614677 -0.275812 0.237087 0.036 Uiso 1 1 calc R U . . .
C27 C -0.64402(17) 0.0382(4) 0.21190(3) 0.0327(4) Uani 1 1 d . . . . .
H27A H -0.609837 -0.078862 0.199181 0.049 Uiso 1 1 calc R U . . .
H27B H -0.568498 0.161411 0.218208 0.049 Uiso 1 1 calc R U . . .
H27C H -0.721698 0.158627 0.206006 0.049 Uiso 1 1 calc R U . . .
H1 H -0.6750(18) 0.138(4) 0.2567(3) 0.046(5) Uiso 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
O1 0.0225(6) 0.0391(7) 0.0384(7) -0.0058(6) -0.0010(5) -0.0020(5)
O2 0.0241(6) 0.0374(7) 0.0307(6) -0.0051(6) -0.0017(5) -0.0025(5)
C1 0.0239(8) 0.0250(8) 0.0261(8) 0.0040(7) -0.0038(6) -0.0026(7)
C2 0.0238(8) 0.0253(9) 0.0292(8) -0.0008(7) -0.0038(6) -0.0021(7)
C3 0.0211(7) 0.0245(8) 0.0251(8) -0.0027(7) -0.0015(6) -0.0034(7)
C4 0.0267(8) 0.0254(9) 0.0272(8) -0.0013(7) -0.0032(6) -0.0050(7)
C5 0.0243(8) 0.0252(8) 0.0237(8) -0.0027(7) -0.0014(6) -0.0032(7)
C6 0.0279(8) 0.0257(8) 0.0251(8) -0.0024(7) -0.0030(6) -0.0053(7)
C7 0.0273(8) 0.0268(9) 0.0242(8) -0.0035(7) -0.0025(6) -0.0026(7)
C8 0.0262(8) 0.0265(9) 0.0250(8) -0.0038(7) -0.0020(6) -0.0035(7)
C9 0.0317(8) 0.0284(9) 0.0268(8) -0.0041(7) -0.0042(7) -0.0020(8)
C10 0.0279(8) 0.0318(9) 0.0257(8) 0.0002(7) -0.0016(7) 0.0016(7)
C11 0.0271(8) 0.0331(9) 0.0243(8) -0.0009(7) -0.0023(6) 0.0011(8)
C12 0.0281(8) 0.0327(9) 0.0263(8) -0.0015(8) -0.0011(7) 0.0026(8)
C13 0.0276(8) 0.0311(9) 0.0268(8) -0.0008(7) -0.0017(7) 0.0023(7)
C14 0.0315(9) 0.0281(9) 0.0290(8) -0.0041(7) -0.0045(7) -0.0010(7)
C15 0.0260(8) 0.0257(9) 0.0248(8) -0.0027(7) -0.0011(6) -0.0027(7)
C16 0.0272(8) 0.0261(9) 0.0243(8) -0.0017(7) -0.0018(6) -0.0031(7)
C17 0.0268(8) 0.0264(9) 0.0240(8) -0.0019(7) -0.0015(6) -0.0014(7)
C18 0.0279(8) 0.0260(9) 0.0234(8) -0.0020(7) -0.0029(6) -0.0006(7)
C19 0.0264(8) 0.0264(9) 0.0255(8) -0.0018(7) -0.0021(6) -0.0014(7)
C20 0.0270(8) 0.0259(8) 0.0252(8) -0.0011(7) -0.0026(6) -0.0002(7)
C21 0.0275(8) 0.0274(9) 0.0251(8) 0.0000(7) -0.0016(6) -0.0025(7)
C22 0.0253(8) 0.0267(9) 0.0258(8) -0.0014(7) -0.0009(6) -0.0006(7)
C23 0.0274(8) 0.0293(9) 0.0259(8) -0.0014(7) -0.0009(6) -0.0004(7)
C24 0.0274(8) 0.0328(10) 0.0277(8) -0.0030(7) 0.0000(7) -0.0008(7)
C25 0.0382(10) 0.0459(12) 0.0314(9) -0.0011(8) -0.0060(8) -0.0024(9)
N1 0.0225(9) 0.0259(10) 0.0229(9) 0.000 0.0012(7) 0.000
C26 0.0305(8) 0.0300(9) 0.0289(8) -0.0035(8) 0.0026(7) 0.0039(8)
C27 0.0291(9) 0.0400(10) 0.0293(9) -0.0029(8) 0.0038(7) 0.0000(8)
_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
O1 C1 1.2372(18) . ?
O2 H2 0.8400 . ?
O2 C1 1.2862(19) . ?
C1 C2 1.510(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.529(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.524(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.520(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.525(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.521(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.524(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.530(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.466(2) . ?
C10 C11 1.200(2) . ?
C11 C12 1.376(2) . ?
C12 C13 1.200(2) . ?
C13 C14 1.463(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.529(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.518(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.522(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.522(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.524(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.521(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.521(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.522(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.523(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.521(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.523(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N1 C26 1.4910(19) . ?
N1 C26 1.4910(19) 2_355 ?
N1 H1 0.975(19) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.511(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
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
C1 O2 H2 109.5 . . ?
O1 C1 O2 121.94(14) . . ?
O1 C1 C2 119.12(15) . . ?
O2 C1 C2 118.93(13) . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C1 C2 C3 111.58(13) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 112.03(13) . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.18(14) . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
C4 C5 C6 112.89(14) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C5 C6 H6A 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 C5 113.76(14) . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
C6 C7 C8 112.78(14) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C7 C8 C9 112.80(14) . . ?
H8A C8 H8B 107.8 . . ?
C9 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C8 C9 H9A 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C10 C9 C8 112.39(14) . . ?
C10 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C11 C10 C9 177.78(18) . . ?
C10 C11 C12 179.4(2) . . ?
C13 C12 C11 179.1(2) . . ?
C12 C13 C14 178.42(19) . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C13 C14 C15 113.15(14) . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C14 C15 H15A 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C14 112.62(14) . . ?
C16 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C15 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C15 C16 C17 113.05(13) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.0 . . ?
C17 C16 H16B 109.0 . . ?
C16 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C18 C17 C16 113.34(13) . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C17 C18 H18A 108.8 . . ?
C17 C18 H18B 108.8 . . ?
C17 C18 C19 113.75(13) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.8 . . ?
C19 C18 H18B 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 C18 113.88(14) . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C19 C20 H20A 108.8 . . ?
C19 C20 H20B 108.8 . . ?
C19 C20 C21 113.67(14) . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C20 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
C20 C21 C22 113.58(14) . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
C21 C22 H22A 108.8 . . ?
C21 C22 H22B 108.8 . . ?
C21 C22 C23 113.65(14) . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
C22 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 C22 113.71(14) . . ?
C24 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C23 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
C23 C24 C25 113.27(15) . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C26 N1 C26 113.76(19) . 2_355 ?
C26 N1 H1 107.8(11) 2_355 . ?
C26 N1 H1 108.4(11) . . ?
N1 C26 H26A 109.7 . . ?
N1 C26 H26B 109.7 . . ?
N1 C26 C27 110.01(15) . . ?
H26A C26 H26B 108.2 . . ?
C27 C26 H26A 109.7 . . ?
C27 C26 H26B 109.7 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O2 0.84 1.62 2.444(2) 166.4 2_455 yes
N1 H1 O1 0.975(19) 1.769(18) 2.7365(16) 171.0(17) . yes
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
C3 C2 C1 O1 99.85(17) . . . . ?
C3 C2 C1 O2 -78.65(18) . . . . ?
C27 C26 N1 C26 177.70(15) . . . 2_355 ?
_iucr_refine_instructions_details
;
TITL 19srv360_a.res in P2/n
REM Old TITL 19srv360 in P2/n #13
REM SHELXT solution in P2/n
REM R1 0.159, Rweak 0.003, Alpha 0.031, Orientation as input
REM Formula found by SHELXT: C50 N5 O4
CELL 0.71073 9.5968 4.6441 57.52 90 92.59 90
ZERR 2 0.0006 0.0003 0.0035 0 0.002 0
LATT 1
SYMM 0.5-X,+Y,0.5-Z
SFAC C H N O
UNIT 108 190 2 8
EQIV $1 -1.5-X,+Y,0.5-Z
EQIV $2 -0.5-X,+Y,0.5-Z
L.S. 9
PLAN 5
SIZE 0.1 0.12 0.5
TEMP -153.15
HTAB N1 O1
CONF C3 C2 C1 O1
CONF C3 C2 C1 O2
CONF C27 C26 N1 C26_$1
HTAB O2 O2_$2
BOND $H
fmap 2 53
acta
OMIT -2 56
OMIT 0 0 6
WGHT 0.038 1.42
FVAR 0.62127
REM
REM
REM
O1 4 -0.54670 0.33401 0.27315 11.00000 0.02248 0.03908 0.03844 =
-0.00584 -0.00105 -0.00202
O2 4 -0.37529 0.16106 0.25298 11.00000 0.02411 0.03736 0.03065 =
-0.00512 -0.00171 -0.00245
PART -1
AFIX 147
H2 2 -0.28804 0.17501 0.25291 10.50000 -1.50000
AFIX 0
PART 0
C1 1 -0.42126 0.32228 0.26913 11.00000 0.02390 0.02498 0.02607 =
0.00398 -0.00380 -0.00264
C2 1 -0.31850 0.49655 0.28398 11.00000 0.02384 0.02530 0.02922 =
-0.00082 -0.00378 -0.00209
AFIX 23
H2a 2 -0.36836 0.65564 0.29149 11.00000 -1.20000
H2b 2 -0.24832 0.58244 0.27396 11.00000 -1.20000
AFIX 0
C3 1 -0.24449 0.31122 0.30272 11.00000 0.02108 0.02455 0.02509 =
-0.00271 -0.00155 -0.00337
AFIX 23
H3a 2 -0.31511 0.21197 0.31185 11.00000 -1.20000
H3b 2 -0.18826 0.16221 0.29516 11.00000 -1.20000
AFIX 0
C4 1 -0.14969 0.48946 0.31909 11.00000 0.02671 0.02542 0.02723 =
-0.00133 -0.00323 -0.00502
AFIX 23
H4a 2 -0.07944 0.58801 0.30983 11.00000 -1.20000
H4b 2 -0.20638 0.63977 0.32638 11.00000 -1.20000
AFIX 0
C5 1 -0.07427 0.31565 0.33819 11.00000 0.02428 0.02521 0.02367 =
-0.00269 -0.00145 -0.00321
AFIX 23
H5a 2 -0.01513 0.16892 0.33097 11.00000 -1.20000
H5b 2 -0.14406 0.21330 0.34729 11.00000 -1.20000
AFIX 0
C6 1 0.01680 0.50124 0.35463 11.00000 0.02791 0.02570 0.02506 =
-0.00240 -0.00301 -0.00535
AFIX 23
H6a 2 0.08235 0.61305 0.34536 11.00000 -1.20000
H6b 2 -0.04344 0.64014 0.36253 11.00000 -1.20000
AFIX 0
C7 1 0.10003 0.32964 0.37299 11.00000 0.02726 0.02683 0.02421 =
-0.00347 -0.00246 -0.00262
AFIX 23
H7a 2 0.16393 0.19748 0.36517 11.00000 -1.20000
H7b 2 0.03511 0.21095 0.38185 11.00000 -1.20000
AFIX 0
C8 1 0.18491 0.52040 0.38989 11.00000 0.02621 0.02652 0.02497 =
-0.00384 -0.00195 -0.00349
AFIX 23
H8a 2 0.12060 0.64586 0.39828 11.00000 -1.20000
H8b 2 0.24647 0.64599 0.38097 11.00000 -1.20000
AFIX 0
C9 1 0.27412 0.34752 0.40764 11.00000 0.03173 0.02845 0.02677 =
-0.00405 -0.00423 -0.00200
AFIX 23
H9a 2 0.21270 0.22166 0.41657 11.00000 -1.20000
H9b 2 0.33876 0.22252 0.39928 11.00000 -1.20000
AFIX 0
C10 1 0.35510 0.53292 0.42386 11.00000 0.02790 0.03178 0.02568 =
0.00024 -0.00163 0.00161
C11 1 0.42074 0.69216 0.43660 11.00000 0.02705 0.03314 0.02428 =
-0.00090 -0.00235 0.00111
C12 1 0.49622 0.87248 0.45138 11.00000 0.02810 0.03274 0.02632 =
-0.00151 -0.00107 0.00264
C13 1 0.56135 1.03282 0.46412 11.00000 0.02758 0.03114 0.02678 =
-0.00081 -0.00169 0.00228
C14 1 0.64129 1.22177 0.48011 11.00000 0.03146 0.02814 0.02902 =
-0.00412 -0.00446 -0.00100
AFIX 23
H14a 2 0.57575 1.34433 0.48850 11.00000 -1.20000
H14b 2 0.70047 1.35006 0.47098 11.00000 -1.20000
AFIX 0
C15 1 0.73404 1.05718 0.49788 11.00000 0.02604 0.02574 0.02481 =
-0.00270 -0.00106 -0.00275
AFIX 23
H15a 2 0.67479 0.93238 0.50729 11.00000 -1.20000
H15b 2 0.79832 0.93138 0.48951 11.00000 -1.20000
AFIX 0
C16 1 0.81886 1.25574 0.51401 11.00000 0.02724 0.02612 0.02429 =
-0.00173 -0.00179 -0.00308
AFIX 23
H16a 2 0.75463 1.38655 0.52190 11.00000 -1.20000
H16b 2 0.88053 1.37549 0.50462 11.00000 -1.20000
AFIX 0
C17 1 0.90755 1.09427 0.53234 11.00000 0.02679 0.02641 0.02402 =
-0.00190 -0.00154 -0.00140
AFIX 23
H17a 2 0.84539 0.98246 0.54223 11.00000 -1.20000
H17b 2 0.96813 0.95595 0.52445 11.00000 -1.20000
AFIX 0
C18 1 0.99848 1.29113 0.54778 11.00000 0.02786 0.02596 0.02340 =
-0.00203 -0.00293 -0.00064
AFIX 23
H18a 2 0.93760 1.42583 0.55598 11.00000 -1.20000
H18b 2 1.05855 1.40705 0.53782 11.00000 -1.20000
AFIX 0
C19 1 1.09072 1.13090 0.56575 11.00000 0.02642 0.02635 0.02552 =
-0.00183 -0.00213 -0.00142
AFIX 23
H19a 2 1.03066 1.01352 0.57561 11.00000 -1.20000
H19b 2 1.15216 0.99749 0.55754 11.00000 -1.20000
AFIX 0
C20 1 1.18076 1.32713 0.58136 11.00000 0.02704 0.02593 0.02523 =
-0.00110 -0.00259 -0.00020
AFIX 23
H20a 2 1.11960 1.46484 0.58919 11.00000 -1.20000
H20b 2 1.24316 1.43974 0.57156 11.00000 -1.20000
AFIX 0
C21 1 1.26907 1.16675 0.59977 11.00000 0.02746 0.02736 0.02510 =
0.00003 -0.00159 -0.00253
AFIX 23
H21a 2 1.33526 1.03985 0.59193 11.00000 -1.20000
H21b 2 1.20739 1.04274 0.60881 11.00000 -1.20000
AFIX 0
C22 1 1.35098 1.36445 0.61649 11.00000 0.02527 0.02668 0.02583 =
-0.00139 -0.00088 -0.00062
AFIX 23
H22a 2 1.28470 1.49011 0.62443 11.00000 -1.20000
H22b 2 1.41197 1.48972 0.60743 11.00000 -1.20000
AFIX 0
C23 1 1.44047 1.20419 0.63480 11.00000 0.02738 0.02932 0.02592 =
-0.00142 -0.00086 -0.00044
AFIX 23
H23a 2 1.38030 1.07043 0.64324 11.00000 -1.20000
H23b 2 1.51039 1.08726 0.62689 11.00000 -1.20000
AFIX 0
C24 1 1.51596 1.40105 0.65236 11.00000 0.02744 0.03285 0.02771 =
-0.00301 0.00002 -0.00080
AFIX 23
H24a 2 1.44611 1.51635 0.66043 11.00000 -1.20000
H24b 2 1.57549 1.53620 0.64393 11.00000 -1.20000
AFIX 0
C25 1 1.60636 1.23880 0.67043 11.00000 0.03825 0.04594 0.03137 =
-0.00111 -0.00597 -0.00237
AFIX 137
H25a 2 1.67938 1.13311 0.66265 11.00000 -1.50000
H25b 2 1.54840 1.10287 0.67874 11.00000 -1.50000
H25c 2 1.64946 1.37600 0.68152 11.00000 -1.50000
AFIX 0
N1 3 -0.75000 0.01871 0.25000 10.50000 0.02249 0.02586 0.02286 =
0.00000 0.00120 0.00000
C26 1 -0.69341 -0.15671 0.23087 11.00000 0.03053 0.03005 0.02892 =
-0.00350 0.00260 0.00387
AFIX 23
H26a 2 -0.76680 -0.28744 0.22439 11.00000 -1.20000
H26b 2 -0.61468 -0.27581 0.23709 11.00000 -1.20000
AFIX 0
C27 1 -0.64402 0.03823 0.21190 11.00000 0.02905 0.04000 0.02935 =
-0.00288 0.00379 0.00001
AFIX 137
H27a 2 -0.60984 -0.07886 0.19918 11.00000 -1.50000
H27b 2 -0.56850 0.16141 0.21821 11.00000 -1.50000
H27c 2 -0.72170 0.15862 0.20601 11.00000 -1.50000
AFIX 0
H1 2 -0.67498 0.13827 0.25672 11.00000 0.04600
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# 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_12_5_19srv342
_database_code_depnum_ccdc_archive 'CCDC 2000836'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record
;
2020-05-04 deposited with the CCDC. 2020-07-20 downloaded from the CCDC.
;
_audit_creation_date 2019-11-21
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2019.10.31 svn.r3677 for OlexSys, GUI svn.r5972)
;
_shelx_SHELXL_version_number 2018/3
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety '2(C25 H41 O2 1-), C10 H22 N2 2+'
_chemical_formula_sum 'C60 H104 N2 O4'
_chemical_formula_weight 917.45
_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 0.0033 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'
_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 triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 5.5770(4)
_cell_length_b 11.8339(8)
_cell_length_c 23.0041(15)
_cell_angle_alpha 100.670(2)
_cell_angle_beta 96.096(2)
_cell_angle_gamma 103.007(2)
_cell_volume 1436.25(17)
_cell_formula_units_Z 1
_cell_measurement_reflns_used 9931
_cell_measurement_temperature 120
_cell_measurement_theta_max 30.03
_cell_measurement_theta_min 2.74
_shelx_estimated_absorpt_T_max 0.994
_shelx_estimated_absorpt_T_min 0.952
_exptl_absorpt_coefficient_mu 0.064
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.8735
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker, 2016) was used for absorption correction.
wR2(int) was 0.1634 before and 0.0536 after correction.
The Ratio of minimum to maximum transmission is 0.8735.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour colourless
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.061
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description lathe
_exptl_crystal_F_000 510
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0500
0.00 0.00 -1.00 0.0240
0.00 -1.00 1.00 0.1470
0.00 1.00 -1.00 0.1520
-1.00 1.00 1.00 0.3310
1.00 0.00 -1.00 0.3350
0.00 1.00 1.00 0.1230
0.00 -1.00 -1.00 0.1130
_exptl_crystal_size_max 0.767
_exptl_crystal_size_mid 0.314
_exptl_crystal_size_min 0.1
_exptl_special_details
;
Data were collected in shutterless mode. Full sphere of reciprocal
space was nominally covered by 4 runs of 340 narrow-frame \w-scans (scan
width 0.5\%, 25s exposure), every run at a different \f angle.
Two runs of 358 \f-scans (scan width 1\%, 1.5s exposure) were used for
scaling overflowing intensities. Crystal to detector distance 3.49 cm.
;
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0455
_diffrn_reflns_av_unetI/netI 0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -17
_diffrn_reflns_limit_l_max 34
_diffrn_reflns_limit_l_min -34
_diffrn_reflns_number 36532
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 32.500
_diffrn_reflns_theta_min 2.194
_diffrn_ambient_temperature 120
_diffrn_detector 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device '3-circle area detector diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Venture'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_current 1.0
_diffrn_source_power 0.05
_diffrn_source_type 'Incoatec I\mS microsource'
_diffrn_source_voltage 50.0
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 7700
_reflns_number_total 10400
_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 'SAINT v8.38A (Bruker, 2017)'
_computing_data_collection 'APEX3 v.2016.1-0 (Bruker, 2016)'
_computing_data_reduction 'SAINT v8.38A (Bruker, 2017)'
_computing_molecular_graphics 'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015a)'
_computing_structure_solution 'ShelXT 2018/2 (Sheldrick, 2015)'
_refine_diff_density_max 0.506
_refine_diff_density_min -0.255
_refine_diff_density_rms 0.046
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.019
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 312
_refine_ls_number_reflns 10400
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0754
_refine_ls_R_factor_gt 0.0497
_refine_ls_restrained_S_all 1.019
_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^)+(0.0649P)^2^+0.3367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1263
_refine_ls_wR_factor_ref 0.1398
_refine_special_details
;
The methyl group was refined as a rigid body rotating around the C---C
bond, with a common refined U for three H atoms. Amino H atoms and H(28): refall,
other H atoms: riding model (constr).
;
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H,H) groups
2. Others
Uiso(H25A)=Uiso(H25B)=Uiso(H25C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C26(H26A,H26B), C27(H27A,
H27B), C29(H29A,H29B), C30(H30A,H30B)
3.b Idealised Me refined as rotating group:
C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary dual
_atom_sites_solution_secondary difmap
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
O1 O 0.08912(13) 1.19236(6) 0.56626(4) 0.02461(16) Uani 1 1 d . . . . .
O2 O -0.23764(13) 1.05641(6) 0.57759(4) 0.02412(16) Uani 1 1 d . . . . .
C1 C -0.00830(17) 1.10020(8) 0.58437(5) 0.01914(18) Uani 1 1 d . . . . .
C2 C 0.1684(2) 1.04557(9) 0.61812(6) 0.0319(3) Uani 1 1 d . . . . .
H2A H 0.308294 1.040292 0.595470 0.038 Uiso 1 1 calc R U . . .
H2B H 0.238817 1.100356 0.657288 0.038 Uiso 1 1 calc R U . . .
C3 C 0.06011(18) 0.92498(9) 0.62926(5) 0.02260(19) Uani 1 1 d . . . . .
H3A H -0.010186 0.869097 0.590399 0.027 Uiso 1 1 calc R U . . .
H3B H -0.077880 0.929338 0.652655 0.027 Uiso 1 1 calc R U . . .
C4 C 0.25156(18) 0.87686(8) 0.66300(5) 0.02062(18) Uani 1 1 d . . . . .
H4A H 0.400560 0.883328 0.642747 0.025 Uiso 1 1 calc R U . . .
H4B H 0.303736 0.926135 0.704108 0.025 Uiso 1 1 calc R U . . .
C5 C 0.15079(19) 0.74818(9) 0.66637(5) 0.02281(19) Uani 1 1 d . . . . .
H5A H 0.091595 0.700053 0.625183 0.027 Uiso 1 1 calc R U . . .
H5B H 0.005325 0.742815 0.687855 0.027 Uiso 1 1 calc R U . . .
C6 C 0.33847(18) 0.69470(8) 0.69753(4) 0.01960(18) Uani 1 1 d . . . . .
H6A H 0.393146 0.740198 0.739343 0.024 Uiso 1 1 calc R U . . .
H6B H 0.486628 0.701626 0.676964 0.024 Uiso 1 1 calc R U . . .
C7 C 0.22971(18) 0.56441(8) 0.69766(5) 0.02116(18) Uani 1 1 d . . . . .
H7A H 0.089565 0.558871 0.720910 0.025 Uiso 1 1 calc R U . . .
H7B H 0.161520 0.520933 0.655984 0.025 Uiso 1 1 calc R U . . .
C8 C 0.41524(18) 0.50373(8) 0.72376(4) 0.01991(18) Uani 1 1 d . . . . .
H8A H 0.480512 0.544915 0.765902 0.024 Uiso 1 1 calc R U . . .
H8B H 0.557242 0.509515 0.701098 0.024 Uiso 1 1 calc R U . . .
C9 C 0.2945(2) 0.37300(9) 0.72113(5) 0.0257(2) Uani 1 1 d . . . . .
H9A H 0.157685 0.368133 0.745406 0.031 Uiso 1 1 calc R U . . .
H9B H 0.220532 0.333654 0.679205 0.031 Uiso 1 1 calc R U . . .
C10 C 0.4683(2) 0.30857(9) 0.74285(5) 0.0249(2) Uani 1 1 d . . . . .
C11 C 0.6099(2) 0.25417(9) 0.75929(5) 0.0243(2) Uani 1 1 d . . . . .
C12 C 0.7688(2) 0.18977(9) 0.77797(5) 0.0250(2) Uani 1 1 d . . . . .
C13 C 0.9099(2) 0.13481(9) 0.79439(5) 0.0265(2) Uani 1 1 d . . . . .
C14 C 1.0930(2) 0.07545(9) 0.81628(6) 0.0298(2) Uani 1 1 d . . . . .
H14A H 1.171695 0.119579 0.857252 0.036 Uiso 1 1 calc R U . . .
H14B H 1.225099 0.080875 0.790626 0.036 Uiso 1 1 calc R U . . .
C15 C 0.99405(19) -0.05460(9) 0.81805(5) 0.02210(19) Uani 1 1 d . . . . .
H15A H 0.858324 -0.062387 0.842637 0.027 Uiso 1 1 calc R U . . .
H15B H 0.925192 -0.101504 0.777006 0.027 Uiso 1 1 calc R U . . .
C16 C 1.20275(19) -0.10238(9) 0.84458(5) 0.02272(19) Uani 1 1 d . . . . .
H16A H 1.335564 -0.094739 0.819159 0.027 Uiso 1 1 calc R U . . .
H16B H 1.274825 -0.051928 0.884729 0.027 Uiso 1 1 calc R U . . .
C17 C 1.12611(19) -0.23083(9) 0.85055(5) 0.02299(19) Uani 1 1 d . . . . .
H17A H 1.044926 -0.281620 0.811044 0.028 Uiso 1 1 calc R U . . .
H17B H 1.002961 -0.238247 0.878497 0.028 Uiso 1 1 calc R U . . .
C18 C 1.34798(19) -0.27476(9) 0.87348(5) 0.02247(19) Uani 1 1 d . . . . .
H18A H 1.469494 -0.267423 0.845140 0.027 Uiso 1 1 calc R U . . .
H18B H 1.430389 -0.222214 0.912482 0.027 Uiso 1 1 calc R U . . .
C19 C 1.28347(19) -0.40243(9) 0.88139(5) 0.02219(19) Uani 1 1 d . . . . .
H19A H 1.194111 -0.455209 0.843013 0.027 Uiso 1 1 calc R U . . .
H19B H 1.169987 -0.409387 0.911563 0.027 Uiso 1 1 calc R U . . .
C20 C 1.51278(19) -0.44372(9) 0.90120(5) 0.02231(19) Uani 1 1 d . . . . .
H20A H 1.623879 -0.437924 0.870472 0.027 Uiso 1 1 calc R U . . .
H20B H 1.604144 -0.389010 0.938883 0.027 Uiso 1 1 calc R U . . .
C21 C 1.45726(18) -0.57004(9) 0.91122(5) 0.02215(19) Uani 1 1 d . . . . .
H21A H 1.348358 -0.576189 0.942381 0.027 Uiso 1 1 calc R U . . .
H21B H 1.365670 -0.625293 0.873708 0.027 Uiso 1 1 calc R U . . .
C22 C 1.69196(19) -0.60734(9) 0.93040(5) 0.02304(19) Uani 1 1 d . . . . .
H22A H 1.784387 -0.550645 0.967402 0.028 Uiso 1 1 calc R U . . .
H22B H 1.799271 -0.601502 0.898896 0.028 Uiso 1 1 calc R U . . .
C23 C 1.64642(19) -0.73243(9) 0.94186(5) 0.0236(2) Uani 1 1 d . . . . .
H23A H 1.533279 -0.739869 0.972086 0.028 Uiso 1 1 calc R U . . .
H23B H 1.562269 -0.789909 0.904366 0.028 Uiso 1 1 calc R U . . .
C24 C 1.8838(2) -0.76391(10) 0.96370(5) 0.0295(2) Uani 1 1 d . . . . .
H24A H 1.965714 -0.707155 1.001594 0.035 Uiso 1 1 calc R U . . .
H24B H 1.998201 -0.754266 0.933878 0.035 Uiso 1 1 calc R U . . .
C25 C 1.8443(3) -0.88941(11) 0.97421(6) 0.0395(3) Uani 1 1 d . . . . .
H25A H 1.767560 -0.946527 0.936691 0.056(3) Uiso 1 1 calc R U . . .
H25B H 1.734787 -0.899370 1.004484 0.056(3) Uiso 1 1 calc R U . . .
H25C H 2.005223 -0.903266 0.988241 0.056(3) Uiso 1 1 calc R U . . .
N N 0.55795(14) 1.22887(7) 0.54666(4) 0.01583(15) Uani 1 1 d . . . . .
HA H 0.392(3) 1.2126(12) 0.5542(6) 0.030(3) Uiso 1 1 d . . . . .
HB H 0.635(3) 1.1686(13) 0.5560(6) 0.035(4) Uiso 1 1 d . . . . .
C26 C 0.69489(17) 1.34429(8) 0.58603(4) 0.01719(17) Uani 1 1 d . . . . .
H26A H 0.871143 1.362332 0.579727 0.021 Uiso 1 1 calc R U . . .
H26B H 0.690872 1.339394 0.628430 0.021 Uiso 1 1 calc R U . . .
C27 C 0.57886(17) 1.44337(8) 0.57270(4) 0.01645(16) Uani 1 1 d . . . . .
H27A H 0.678017 1.519941 0.598215 0.020 Uiso 1 1 calc R U . . .
H27B H 0.408455 1.429054 0.583109 0.020 Uiso 1 1 calc R U . . .
C28 C 0.56599(16) 1.45225(7) 0.50674(4) 0.01313(15) Uani 1 1 d . . . . .
H28 H 0.735(2) 1.4747(10) 0.4983(5) 0.014(3) Uiso 1 1 d . . . . .
C29 C 0.43855(17) 1.32917(7) 0.46755(4) 0.01694(17) Uani 1 1 d . . . . .
H29A H 0.260879 1.308760 0.472543 0.020 Uiso 1 1 calc R U . . .
H29B H 0.445873 1.332096 0.425028 0.020 Uiso 1 1 calc R U . . .
C30 C 0.55713(17) 1.23216(8) 0.48264(4) 0.01755(17) Uani 1 1 d . . . . .
H30A H 0.462651 1.154314 0.457507 0.021 Uiso 1 1 calc R U . . .
H30B H 0.730143 1.247543 0.473911 0.021 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0164(3) 0.0200(3) 0.0449(5) 0.0189(3) 0.0091(3) 0.0081(3)
O2 0.0152(3) 0.0182(3) 0.0436(4) 0.0161(3) 0.0037(3) 0.0064(2)
C1 0.0162(4) 0.0162(4) 0.0294(5) 0.0107(3) 0.0043(3) 0.0077(3)
C2 0.0192(5) 0.0207(5) 0.0580(8) 0.0220(5) -0.0043(5) 0.0032(4)
C3 0.0184(4) 0.0175(4) 0.0350(5) 0.0130(4) 0.0014(4) 0.0061(3)
C4 0.0214(4) 0.0181(4) 0.0261(5) 0.0106(4) 0.0025(3) 0.0085(3)
C5 0.0212(4) 0.0206(4) 0.0307(5) 0.0125(4) 0.0013(4) 0.0090(3)
C6 0.0221(4) 0.0181(4) 0.0213(4) 0.0075(3) 0.0011(3) 0.0088(3)
C7 0.0222(4) 0.0177(4) 0.0260(5) 0.0067(4) 0.0021(4) 0.0092(3)
C8 0.0234(4) 0.0177(4) 0.0214(4) 0.0064(3) 0.0024(3) 0.0094(3)
C9 0.0257(5) 0.0187(4) 0.0352(6) 0.0097(4) 0.0013(4) 0.0092(4)
C10 0.0291(5) 0.0180(4) 0.0298(5) 0.0083(4) 0.0041(4) 0.0083(4)
C11 0.0278(5) 0.0185(4) 0.0289(5) 0.0087(4) 0.0047(4) 0.0078(4)
C12 0.0276(5) 0.0191(4) 0.0310(5) 0.0092(4) 0.0049(4) 0.0078(4)
C13 0.0267(5) 0.0194(4) 0.0357(6) 0.0099(4) 0.0038(4) 0.0078(4)
C14 0.0226(5) 0.0204(5) 0.0492(7) 0.0131(4) 0.0019(4) 0.0079(4)
C15 0.0218(4) 0.0191(4) 0.0282(5) 0.0088(4) 0.0030(4) 0.0082(3)
C16 0.0221(5) 0.0202(4) 0.0289(5) 0.0097(4) 0.0029(4) 0.0086(4)
C17 0.0226(5) 0.0205(4) 0.0296(5) 0.0108(4) 0.0040(4) 0.0088(4)
C18 0.0231(5) 0.0207(4) 0.0269(5) 0.0107(4) 0.0025(4) 0.0083(4)
C19 0.0232(5) 0.0211(4) 0.0263(5) 0.0114(4) 0.0042(4) 0.0084(4)
C20 0.0226(5) 0.0209(4) 0.0257(5) 0.0105(4) 0.0010(4) 0.0069(3)
C21 0.0213(4) 0.0203(4) 0.0269(5) 0.0105(4) 0.0013(4) 0.0063(3)
C22 0.0220(5) 0.0190(4) 0.0293(5) 0.0098(4) -0.0003(4) 0.0060(3)
C23 0.0233(5) 0.0195(4) 0.0293(5) 0.0097(4) 0.0009(4) 0.0061(4)
C24 0.0300(5) 0.0225(5) 0.0380(6) 0.0096(4) -0.0015(4) 0.0111(4)
C25 0.0512(8) 0.0272(6) 0.0488(8) 0.0172(5) 0.0074(6) 0.0203(5)
N 0.0145(3) 0.0117(3) 0.0243(4) 0.0083(3) 0.0035(3) 0.0056(3)
C26 0.0195(4) 0.0135(4) 0.0201(4) 0.0059(3) 0.0006(3) 0.0065(3)
C27 0.0213(4) 0.0130(4) 0.0175(4) 0.0054(3) 0.0022(3) 0.0078(3)
C28 0.0147(4) 0.0093(3) 0.0169(4) 0.0048(3) 0.0027(3) 0.0043(3)
C29 0.0219(4) 0.0104(3) 0.0187(4) 0.0032(3) -0.0005(3) 0.0061(3)
C30 0.0209(4) 0.0108(3) 0.0221(4) 0.0040(3) 0.0026(3) 0.0064(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
O1 C1 1.2679(11) . ?
O2 C1 1.2482(12) . ?
C1 C2 1.5175(13) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.4991(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5258(13) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5194(13) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5220(13) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5253(13) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5195(13) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5291(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.4632(14) . ?
C10 C11 1.1986(14) . ?
C11 C12 1.3768(14) . ?
C12 C13 1.2013(14) . ?
C13 C14 1.4611(14) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5233(14) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5231(13) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5198(14) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5271(13) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5219(13) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.5238(14) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.5224(13) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.5206(14) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.5215(13) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5145(14) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.5198(15) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N HA 0.944(14) . ?
N HB 0.959(15) . ?
N C26 1.4814(12) . ?
N C30 1.4800(12) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.5232(12) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.5354(12) . ?
C28 C28 1.5399(16) 2_686 ?
C28 H28 0.971(12) . ?
C28 C29 1.5333(12) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C30 1.5219(12) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
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
O1 C1 C2 116.67(8) . . ?
O2 C1 O1 123.52(8) . . ?
O2 C1 C2 119.76(8) . . ?
C1 C2 H2A 108.2 . . ?
C1 C2 H2B 108.2 . . ?
H2A C2 H2B 107.3 . . ?
C3 C2 C1 116.46(9) . . ?
C3 C2 H2A 108.2 . . ?
C3 C2 H2B 108.2 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C2 C3 C4 112.76(8) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 112.46(8) . . ?
C5 C4 H4A 109.1 . . ?
C5 C4 H4B 109.1 . . ?
C4 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C4 C5 C6 114.39(8) . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C5 C6 H6A 109.2 . . ?
C5 C6 H6B 109.2 . . ?
C5 C6 C7 112.03(8) . . ?
H6A C6 H6B 107.9 . . ?
C7 C6 H6A 109.2 . . ?
C7 C6 H6B 109.2 . . ?
C6 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 C6 114.27(8) . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C7 C8 C9 111.27(8) . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C8 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C8 113.59(9) . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C11 C10 C9 178.43(12) . . ?
C10 C11 C12 178.91(11) . . ?
C13 C12 C11 179.19(11) . . ?
C12 C13 C14 176.21(12) . . ?
C13 C14 H14A 108.3 . . ?
C13 C14 H14B 108.3 . . ?
C13 C14 C15 116.07(9) . . ?
H14A C14 H14B 107.4 . . ?
C15 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C16 C15 C14 110.02(8) . . ?
C16 C15 H15A 109.7 . . ?
C16 C15 H15B 109.7 . . ?
C15 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 C15 115.23(8) . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C16 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C16 C17 C18 112.14(8) . . ?
H17A C17 H17B 107.9 . . ?
C18 C17 H17A 109.2 . . ?
C18 C17 H17B 109.2 . . ?
C17 C18 H18A 108.6 . . ?
C17 C18 H18B 108.6 . . ?
H18A C18 H18B 107.5 . . ?
C19 C18 C17 114.84(8) . . ?
C19 C18 H18A 108.6 . . ?
C19 C18 H18B 108.6 . . ?
C18 C19 H19A 109.1 . . ?
C18 C19 H19B 109.1 . . ?
C18 C19 C20 112.65(8) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C19 C20 H20A 108.6 . . ?
C19 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
C21 C20 C19 114.61(8) . . ?
C21 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
C20 C21 H21A 109.1 . . ?
C20 C21 H21B 109.1 . . ?
H21A C21 H21B 107.8 . . ?
C22 C21 C20 112.59(8) . . ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C21 C22 H22A 108.6 . . ?
C21 C22 H22B 108.6 . . ?
C21 C22 C23 114.68(8) . . ?
H22A C22 H22B 107.6 . . ?
C23 C22 H22A 108.6 . . ?
C23 C22 H22B 108.6 . . ?
C22 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 C22 112.99(9) . . ?
C24 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
C23 C24 H24A 108.7 . . ?
C23 C24 H24B 108.7 . . ?
C23 C24 C25 114.11(10) . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
HA N HB 110.2(12) . . ?
C26 N HA 108.0(8) . . ?
C26 N HB 108.6(9) . . ?
C30 N HA 108.7(8) . . ?
C30 N HB 109.8(8) . . ?
C30 N C26 111.51(7) . . ?
N C26 H26A 109.5 . . ?
N C26 H26B 109.5 . . ?
N C26 C27 110.62(7) . . ?
H26A C26 H26B 108.1 . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
C26 C27 H27A 109.1 . . ?
C26 C27 H27B 109.1 . . ?
C26 C27 C28 112.58(7) . . ?
H27A C27 H27B 107.8 . . ?
C28 C27 H27A 109.1 . . ?
C28 C27 H27B 109.1 . . ?
C27 C28 C28 111.86(9) . 2_686 ?
C27 C28 H28 108.3(7) . . ?
C28 C28 H28 107.7(7) 2_686 . ?
C29 C28 C27 108.48(7) . . ?
C29 C28 C28 112.21(9) . 2_686 ?
C29 C28 H28 108.1(7) . . ?
C28 C29 H29A 109.0 . . ?
C28 C29 H29B 109.0 . . ?
H29A C29 H29B 107.8 . . ?
C30 C29 C28 113.05(7) . . ?
C30 C29 H29A 109.0 . . ?
C30 C29 H29B 109.0 . . ?
N C30 C29 110.20(7) . . ?
N C30 H30A 109.6 . . ?
N C30 H30B 109.6 . . ?
C29 C30 H30A 109.6 . . ?
C29 C30 H30B 109.6 . . ?
H30A C30 H30B 108.1 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N HA O1 0.944(14) 1.711(14) 2.6534(10) 175.9(13) . yes
N HB O2 0.959(15) 1.761(15) 2.7173(10) 175.5(13) 1_655 yes
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
O1 C1 C2 C3 -168.81(10) . . . . ?
O2 C1 C2 C3 13.68(16) . . . . ?
C1 C2 C3 C4 179.57(10) . . . . ?
C2 C3 C4 C5 -171.83(10) . . . . ?
C3 C4 C5 C6 177.73(8) . . . . ?
C4 C5 C6 C7 -178.03(8) . . . . ?
C5 C6 C7 C8 175.33(8) . . . . ?
C6 C7 C8 C9 -178.76(8) . . . . ?
C7 C8 C9 C10 176.98(9) . . . . ?
C13 C14 C15 C16 -177.23(10) . . . . ?
C14 C15 C16 C17 178.25(9) . . . . ?
C15 C16 C17 C18 176.16(9) . . . . ?
C16 C17 C18 C19 179.13(9) . . . . ?
C17 C18 C19 C20 177.01(9) . . . . ?
C18 C19 C20 C21 178.57(9) . . . . ?
C19 C20 C21 C22 179.52(9) . . . . ?
C20 C21 C22 C23 179.17(9) . . . . ?
C21 C22 C23 C24 -177.25(9) . . . . ?
C22 C23 C24 C25 -178.72(10) . . . . ?
N C26 C27 C28 -56.21(10) . . . . ?
C26 N C30 C29 -58.55(9) . . . . ?
C26 C27 C28 C28 176.56(9) . . . 2_686 ?
C26 C27 C28 C29 52.25(10) . . . . ?
C27 C28 C29 C30 -52.59(10) . . . . ?
C28 C28 C29 C30 -176.68(9) 2_686 . . . ?
C28 C29 C30 N 56.43(10) . . . . ?
C30 N C26 C27 58.73(9) . . . . ?
_shelx_res_file
;
TITL 19asb011_a.res in P-1
19srv342.res
created by SHELXL-2018/3 at 22:19:40 on 21-Nov-2019
REM Old TITL 19asb011 in P-1 #2
REM SHELXT solution in P-1: R1 0.156, Rweak 0.005, Alpha 0.033
REM 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C28 N3 O2
CELL 0.71073 5.577 11.8339 23.0041 100.67 96.096 103.007
ZERR 1 0.0004 0.0008 0.0015 0.002 0.002 0.002
LATT 1
SFAC C H N O
UNIT 60 104 2 4
EQIV $1 1+X,+Y,+Z
L.S. 7
PLAN 11
SIZE 0.1 0.314 0.767
TEMP -153.15
CONF
HTAB N O1
HTAB N O2_$1
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
OMIT -3 65
REM
REM
REM
WGHT 0.064900 0.336700
FVAR 1.04732 0.05580
O1 4 0.089123 1.192363 0.566265 11.00000 0.01642 0.02003 =
0.04486 0.01886 0.00913 0.00811
O2 4 -0.237636 1.056413 0.577590 11.00000 0.01524 0.01821 =
0.04358 0.01608 0.00365 0.00638
C1 1 -0.008302 1.100201 0.584365 11.00000 0.01618 0.01615 =
0.02940 0.01074 0.00432 0.00771
C2 1 0.168436 1.045569 0.618125 11.00000 0.01918 0.02069 =
0.05804 0.02198 -0.00427 0.00323
AFIX 23
H2A 2 0.308294 1.040292 0.595470 11.00000 -1.20000
H2B 2 0.238817 1.100356 0.657288 11.00000 -1.20000
AFIX 0
C3 1 0.060111 0.924975 0.629260 11.00000 0.01837 0.01751 =
0.03504 0.01302 0.00144 0.00607
AFIX 23
H3A 2 -0.010186 0.869097 0.590399 11.00000 -1.20000
H3B 2 -0.077880 0.929338 0.652655 11.00000 -1.20000
AFIX 0
C4 1 0.251564 0.876857 0.662997 11.00000 0.02141 0.01814 =
0.02609 0.01059 0.00247 0.00847
AFIX 23
H4A 2 0.400560 0.883328 0.642747 11.00000 -1.20000
H4B 2 0.303736 0.926135 0.704108 11.00000 -1.20000
AFIX 0
C5 1 0.150792 0.748178 0.666369 11.00000 0.02116 0.02063 =
0.03067 0.01248 0.00135 0.00903
AFIX 23
H5A 2 0.091595 0.700053 0.625183 11.00000 -1.20000
H5B 2 0.005325 0.742815 0.687855 11.00000 -1.20000
AFIX 0
C6 1 0.338474 0.694705 0.697529 11.00000 0.02207 0.01805 =
0.02131 0.00748 0.00113 0.00875
AFIX 23
H6A 2 0.393146 0.740198 0.739343 11.00000 -1.20000
H6B 2 0.486628 0.701626 0.676964 11.00000 -1.20000
AFIX 0
C7 1 0.229713 0.564406 0.697655 11.00000 0.02223 0.01774 =
0.02599 0.00672 0.00212 0.00919
AFIX 23
H7A 2 0.089565 0.558871 0.720910 11.00000 -1.20000
H7B 2 0.161520 0.520933 0.655984 11.00000 -1.20000
AFIX 0
C8 1 0.415244 0.503729 0.723759 11.00000 0.02337 0.01774 =
0.02138 0.00642 0.00242 0.00944
AFIX 23
H8A 2 0.480512 0.544915 0.765902 11.00000 -1.20000
H8B 2 0.557242 0.509515 0.701098 11.00000 -1.20000
AFIX 0
C9 1 0.294524 0.373000 0.721134 11.00000 0.02569 0.01868 =
0.03524 0.00965 0.00135 0.00925
AFIX 23
H9A 2 0.157685 0.368133 0.745406 11.00000 -1.20000
H9B 2 0.220532 0.333654 0.679205 11.00000 -1.20000
AFIX 0
C10 1 0.468292 0.308572 0.742851 11.00000 0.02907 0.01801 =
0.02980 0.00832 0.00405 0.00827
C11 1 0.609892 0.254169 0.759286 11.00000 0.02784 0.01855 =
0.02895 0.00867 0.00470 0.00778
C12 1 0.768824 0.189774 0.777974 11.00000 0.02756 0.01910 =
0.03100 0.00920 0.00495 0.00779
C13 1 0.909916 0.134813 0.794391 11.00000 0.02668 0.01944 =
0.03567 0.00995 0.00376 0.00777
C14 1 1.093031 0.075453 0.816285 11.00000 0.02257 0.02043 =
0.04916 0.01314 0.00191 0.00791
AFIX 23
H14A 2 1.171695 0.119579 0.857252 11.00000 -1.20000
H14B 2 1.225099 0.080875 0.790626 11.00000 -1.20000
AFIX 0
C15 1 0.994048 -0.054599 0.818052 11.00000 0.02178 0.01912 =
0.02816 0.00876 0.00296 0.00818
AFIX 23
H15A 2 0.858324 -0.062387 0.842637 11.00000 -1.20000
H15B 2 0.925192 -0.101504 0.777006 11.00000 -1.20000
AFIX 0
C16 1 1.202752 -0.102380 0.844577 11.00000 0.02212 0.02025 =
0.02894 0.00973 0.00290 0.00860
AFIX 23
H16A 2 1.335564 -0.094739 0.819159 11.00000 -1.20000
H16B 2 1.274825 -0.051928 0.884729 11.00000 -1.20000
AFIX 0
C17 1 1.126105 -0.230832 0.850554 11.00000 0.02257 0.02055 =
0.02965 0.01079 0.00398 0.00878
AFIX 23
H17A 2 1.044926 -0.281620 0.811044 11.00000 -1.20000
H17B 2 1.002961 -0.238247 0.878497 11.00000 -1.20000
AFIX 0
C18 1 1.347982 -0.274763 0.873479 11.00000 0.02307 0.02070 =
0.02693 0.01074 0.00251 0.00826
AFIX 23
H18A 2 1.469494 -0.267423 0.845140 11.00000 -1.20000
H18B 2 1.430389 -0.222214 0.912482 11.00000 -1.20000
AFIX 0
C19 1 1.283470 -0.402434 0.881391 11.00000 0.02323 0.02109 =
0.02627 0.01140 0.00417 0.00843
AFIX 23
H19A 2 1.194111 -0.455209 0.843013 11.00000 -1.20000
H19B 2 1.169987 -0.409387 0.911563 11.00000 -1.20000
AFIX 0
C20 1 1.512783 -0.443721 0.901200 11.00000 0.02263 0.02086 =
0.02571 0.01048 0.00098 0.00690
AFIX 23
H20A 2 1.623879 -0.437924 0.870472 11.00000 -1.20000
H20B 2 1.604144 -0.389010 0.938883 11.00000 -1.20000
AFIX 0
C21 1 1.457263 -0.570037 0.911216 11.00000 0.02129 0.02035 =
0.02695 0.01047 0.00132 0.00629
AFIX 23
H21A 2 1.348358 -0.576189 0.942381 11.00000 -1.20000
H21B 2 1.365670 -0.625293 0.873708 11.00000 -1.20000
AFIX 0
C22 1 1.691960 -0.607337 0.930397 11.00000 0.02202 0.01903 =
0.02932 0.00978 -0.00031 0.00597
AFIX 23
H22A 2 1.784387 -0.550645 0.967402 11.00000 -1.20000
H22B 2 1.799271 -0.601502 0.898896 11.00000 -1.20000
AFIX 0
C23 1 1.646420 -0.732426 0.941864 11.00000 0.02327 0.01949 =
0.02931 0.00966 0.00085 0.00609
AFIX 23
H23A 2 1.533279 -0.739869 0.972086 11.00000 -1.20000
H23B 2 1.562269 -0.789909 0.904366 11.00000 -1.20000
AFIX 0
C24 1 1.883792 -0.763912 0.963703 11.00000 0.03003 0.02250 =
0.03799 0.00961 -0.00147 0.01107
AFIX 23
H24A 2 1.965714 -0.707155 1.001594 11.00000 -1.20000
H24B 2 1.998201 -0.754266 0.933878 11.00000 -1.20000
AFIX 0
C25 1 1.844337 -0.889412 0.974213 11.00000 0.05125 0.02720 =
0.04878 0.01719 0.00736 0.02030
AFIX 137
H25A 2 1.767560 -0.946527 0.936691 11.00000 21.00000
H25B 2 1.734787 -0.899370 1.004484 11.00000 21.00000
H25C 2 2.005223 -0.903266 0.988241 11.00000 21.00000
AFIX 0
N 3 0.557954 1.228872 0.546658 11.00000 0.01447 0.01169 =
0.02434 0.00827 0.00354 0.00560
HA 2 0.391890 1.212589 0.554175 11.00000 0.03046
HB 2 0.635480 1.168577 0.556049 11.00000 0.03505
C26 1 0.694892 1.344292 0.586033 11.00000 0.01952 0.01350 =
0.02007 0.00586 0.00056 0.00653
AFIX 23
H26A 2 0.871143 1.362332 0.579727 11.00000 -1.20000
H26B 2 0.690872 1.339394 0.628430 11.00000 -1.20000
AFIX 0
C27 1 0.578855 1.443366 0.572696 11.00000 0.02126 0.01304 =
0.01745 0.00539 0.00225 0.00782
AFIX 23
H27A 2 0.678017 1.519941 0.598215 11.00000 -1.20000
H27B 2 0.408455 1.429054 0.583109 11.00000 -1.20000
AFIX 0
C28 1 0.565994 1.452247 0.506744 11.00000 0.01470 0.00929 =
0.01687 0.00483 0.00267 0.00425
H28 2 0.734927 1.474749 0.498252 11.00000 0.01392
C29 1 0.438553 1.329170 0.467550 11.00000 0.02191 0.01043 =
0.01868 0.00317 -0.00052 0.00614
AFIX 23
H29A 2 0.260879 1.308760 0.472543 11.00000 -1.20000
H29B 2 0.445873 1.332096 0.425028 11.00000 -1.20000
AFIX 0
C30 1 0.557126 1.232162 0.482638 11.00000 0.02092 0.01084 =
0.02213 0.00404 0.00265 0.00638
AFIX 23
H30A 2 0.462651 1.154314 0.457507 11.00000 -1.20000
H30B 2 0.730143 1.247543 0.473911 11.00000 -1.20000
AFIX 0
HKLF 4
REM 19asb011_a.res in P-1
REM wR2 = 0.1398, GooF = S = 1.019, Restrained GooF = 1.019 for all data
REM R1 = 0.0497 for 7700 Fo > 4sig(Fo) and 0.0754 for all 10400 data
REM 312 parameters refined using 0 restraints
END
WGHT 0.0660 0.3325
REM Highest difference peak 0.506, deepest hole -0.255, 1-sigma level 0.046
Q1 1 0.2059 0.8017 0.6628 11.00000 0.05 0.51
Q2 1 0.1596 0.9984 0.6548 11.00000 0.05 0.45
Q3 1 0.1043 0.9787 0.5905 11.00000 0.05 0.43
Q4 1 0.5000 1.5000 0.5000 10.50000 0.05 0.41
Q5 1 0.3402 0.9342 0.6799 11.00000 0.05 0.39
Q6 1 0.5696 1.4433 0.5390 11.00000 0.05 0.38
Q7 1 0.4997 1.2827 0.4778 11.00000 0.05 0.37
Q8 1 0.2751 0.6248 0.6928 11.00000 0.05 0.36
Q9 1 0.3481 0.4358 0.7213 11.00000 0.05 0.35
Q10 1 0.6326 1.3969 0.5789 11.00000 0.05 0.33
Q11 1 1.5886 -0.5857 0.9221 11.00000 0.05 0.33
;
_shelx_res_checksum 16069
#######################################################################
#
# 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_1_19srv221
_database_code_depnum_ccdc_archive 'CCDC 2000831'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record
;
2020-05-04 deposited with the CCDC. 2020-07-20 downloaded from the CCDC.
;
_audit_creation_date 2019-07-15
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2017/1
loop_
_audit_author_email
d.s.yufit@durham.ac.uk
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C25 H42 O2'
_chemical_formula_sum 'C25 H42 O2'
_chemical_formula_weight 374.58
_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 0.0032 0.0015 '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 0.0108 0.0057 '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 triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 4.5738(3)
_cell_length_b 5.3909(3)
_cell_length_c 46.647(3)
_cell_angle_alpha 88.6499(15)
_cell_angle_beta 88.5073(14)
_cell_angle_gamma 81.4017(14)
_cell_volume 1136.64(12)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 5706
_cell_measurement_temperature 100.0
_cell_measurement_theta_max 30.53
_cell_measurement_theta_min 2.96
_shelx_estimated_absorpt_T_max 0.999
_shelx_estimated_absorpt_T_min 0.992
_exptl_absorpt_coefficient_mu 0.063
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.7743
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1415 before and 0.0688 after correction.
The Ratio of minimum to maximum transmission is 0.7743.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.094
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plank
_exptl_crystal_F_000 416
_exptl_crystal_size_max 0.12
_exptl_crystal_size_mid 0.04
_exptl_crystal_size_min 0.01
_exptl_transmission_factor_max 1.0000
_exptl_transmission_factor_min 0.7743
_diffrn_reflns_av_R_equivalents 0.0574
_diffrn_reflns_av_unetI/netI 0.0775
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max 6
_diffrn_reflns_limit_h_min -6
_diffrn_reflns_limit_k_max 7
_diffrn_reflns_limit_k_min -7
_diffrn_reflns_limit_l_max 65
_diffrn_reflns_limit_l_min -66
_diffrn_reflns_number 21023
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full 24.415
_diffrn_reflns_theta_max 29.497
_diffrn_reflns_theta_min 0.847
_diffrn_ambient_temperature 100.0
_diffrn_detector 'Photon counting pixel array'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type 'Dectris Pilatus 2M'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device 'Fixed \c 3-circle diffractometer'
_diffrn_measurement_device_type 'Fluid Film Devices'
_diffrn_measurement_method '\f and \w rotation with 0.1 degree frames'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator 'Silicon 111'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type synchrotron
_diffrn_radiation_wavelength 0.6889
_diffrn_source Synchrotron
_diffrn_source_type 'Undulator, I19, DLS, RAL'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5115
_reflns_number_total 6893
_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 'SAINT V8.38A (Bruker AXS, 2016)'
_computing_data_collection 'GDA 8.44; generic data acquisition software'
_computing_data_reduction 'SAINT V8.38A (Bruker AXS, 2016)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max 0.533
_refine_diff_density_min -0.273
_refine_diff_density_rms 0.068
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.035
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 249
_refine_ls_number_reflns 6893
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0802
_refine_ls_R_factor_gt 0.0640
_refine_ls_restrained_S_all 1.035
_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^)+(0.1100P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1772
_refine_ls_wR_factor_ref 0.1886
_refine_special_details ?
_olex2_refinement_description
;
1. Fixed Uiso
At 1.2 times of:
All C(H,H) groups
At 1.5 times of:
All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
2.b Idealised Me refined as rotating group:
C25(H25A,H25B,H25C)
;
_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
O1 O 0.25012(15) 2.76982(13) -0.00177(2) 0.01893(18) Uani 1 1 d . . . . .
O2 O 0.53138(15) 2.87853(12) 0.03292(2) 0.01831(18) Uani 1 1 d . . . . .
C1 C 0.3499(2) 2.75262(17) 0.02466(2) 0.0133(2) Uani 1 1 d . . . . .
C2 C 0.2140(2) 2.57029(18) 0.04356(2) 0.0159(2) Uani 1 1 d . . . . .
H2A H 0.156061 2.438123 0.031447 0.019 Uiso 1 1 calc R . . . .
H2B H 0.031404 2.659475 0.052672 0.019 Uiso 1 1 calc R . . . .
C3 C 0.4148(2) 2.44489(17) 0.06708(2) 0.0132(2) Uani 1 1 d . . . . .
H3A H 0.590880 2.343943 0.058160 0.016 Uiso 1 1 calc R . . . .
H3B H 0.483456 2.575727 0.078650 0.016 Uiso 1 1 calc R . . . .
C4 C 0.2551(2) 2.27598(17) 0.08664(2) 0.0143(2) Uani 1 1 d . . . . .
H4A H 0.156254 2.165585 0.074663 0.017 Uiso 1 1 calc R . . . .
H4B H 0.099810 2.381763 0.097920 0.017 Uiso 1 1 calc R . . . .
C5 C 0.4595(2) 2.11348(17) 0.10722(2) 0.0136(2) Uani 1 1 d . . . . .
H5A H 0.612959 2.005715 0.095950 0.016 Uiso 1 1 calc R . . . .
H5B H 0.560586 2.223665 0.119016 0.016 Uiso 1 1 calc R . . . .
C6 C 0.2983(2) 1.94779(17) 0.12703(2) 0.0142(2) Uani 1 1 d . . . . .
H6A H 0.189003 1.843999 0.115196 0.017 Uiso 1 1 calc R . . . .
H6B H 0.151339 2.056299 0.138919 0.017 Uiso 1 1 calc R . . . .
C7 C 0.5013(2) 1.77530(17) 0.14675(2) 0.0147(2) Uani 1 1 d . . . . .
H7A H 0.653410 1.671200 0.134943 0.018 Uiso 1 1 calc R . . . .
H7B H 0.604240 1.878919 0.159219 0.018 Uiso 1 1 calc R . . . .
C8 C 0.3381(2) 1.60387(17) 0.16549(2) 0.0144(2) Uani 1 1 d . . . . .
H8A H 0.242924 1.494230 0.153079 0.017 Uiso 1 1 calc R . . . .
H8B H 0.180281 1.707188 0.176725 0.017 Uiso 1 1 calc R . . . .
C9 C 0.5443(2) 1.44019(19) 0.18610(2) 0.0189(2) Uani 1 1 d . . . . .
H9A H 0.709647 1.346082 0.174886 0.023 Uiso 1 1 calc R . . . .
H9B H 0.629326 1.550262 0.199278 0.023 Uiso 1 1 calc R . . . .
C10 C 0.3960(2) 1.26217(18) 0.20303(2) 0.0183(2) Uani 1 1 d . . . . .
C11 C 0.2716(2) 1.11325(18) 0.21631(2) 0.0183(2) Uani 1 1 d . . . . .
C12 C 0.1314(2) 0.94212(18) 0.23186(2) 0.0181(2) Uani 1 1 d . . . . .
C13 C 0.0079(2) 0.79318(18) 0.24520(2) 0.0182(2) Uani 1 1 d . . . . .
C14 C -0.1392(2) 0.61542(18) 0.26241(2) 0.0178(2) Uani 1 1 d . . . . .
H14A H -0.227752 0.506215 0.249403 0.021 Uiso 1 1 calc R . . . .
H14B H -0.301677 0.709895 0.273945 0.021 Uiso 1 1 calc R . . . .
C15 C 0.0712(2) 0.45052(17) 0.28260(2) 0.0138(2) Uani 1 1 d . . . . .
H15A H 0.225589 0.346521 0.271032 0.017 Uiso 1 1 calc R . . . .
H15B H 0.170453 0.559446 0.294728 0.017 Uiso 1 1 calc R . . . .
C16 C -0.0894(2) 0.27965(17) 0.30180(2) 0.0138(2) Uani 1 1 d . . . . .
H16A H -0.199766 0.179249 0.289651 0.017 Uiso 1 1 calc R . . . .
H16B H -0.234899 0.384321 0.314221 0.017 Uiso 1 1 calc R . . . .
C17 C 0.1188(2) 0.10260(17) 0.32062(2) 0.0134(2) Uani 1 1 d . . . . .
H17A H 0.257790 -0.007405 0.308119 0.016 Uiso 1 1 calc R . . . .
H17B H 0.236671 0.203121 0.331958 0.016 Uiso 1 1 calc R . . . .
C18 C -0.0385(2) -0.06090(17) 0.34107(2) 0.0132(2) Uani 1 1 d . . . . .
H18A H -0.159322 -0.159196 0.329770 0.016 Uiso 1 1 calc R . . . .
H18B H -0.174660 0.048971 0.353832 0.016 Uiso 1 1 calc R . . . .
C19 C 0.1713(2) -0.24128(17) 0.35948(2) 0.0132(2) Uani 1 1 d . . . . .
H19A H 0.305835 -0.352456 0.346714 0.016 Uiso 1 1 calc R . . . .
H19B H 0.293839 -0.143060 0.370592 0.016 Uiso 1 1 calc R . . . .
C20 C 0.0144(2) -0.40294(17) 0.38022(2) 0.0134(2) Uani 1 1 d . . . . .
H20A H -0.110360 -0.499367 0.369132 0.016 Uiso 1 1 calc R . . . .
H20B H -0.118146 -0.291770 0.393161 0.016 Uiso 1 1 calc R . . . .
C21 C 0.2238(2) -0.58560(17) 0.39834(2) 0.0134(2) Uani 1 1 d . . . . .
H21A H 0.353821 -0.698853 0.385413 0.016 Uiso 1 1 calc R . . . .
H21B H 0.351051 -0.489457 0.409160 0.016 Uiso 1 1 calc R . . . .
C22 C 0.0668(2) -0.74363(17) 0.41942(2) 0.0142(2) Uani 1 1 d . . . . .
H22A H -0.064464 -0.836162 0.408621 0.017 Uiso 1 1 calc R . . . .
H22B H -0.059433 -0.630292 0.432629 0.017 Uiso 1 1 calc R . . . .
C23 C 0.2744(2) -0.93125(17) 0.43710(2) 0.0142(2) Uani 1 1 d . . . . .
H23A H 0.401535 -1.044330 0.423934 0.017 Uiso 1 1 calc R . . . .
H23B H 0.404557 -0.839024 0.448069 0.017 Uiso 1 1 calc R . . . .
C24 C 0.1139(2) -1.08869(18) 0.45787(2) 0.0178(2) Uani 1 1 d . . . . .
H24A H -0.018350 -1.179029 0.446921 0.021 Uiso 1 1 calc R . . . .
H24B H -0.011264 -0.975637 0.471192 0.021 Uiso 1 1 calc R . . . .
C25 C 0.3209(2) -1.27909(19) 0.47534(2) 0.0217(2) Uani 1 1 d . . . . .
H25A H 0.444230 -1.393209 0.462342 0.032 Uiso 1 1 calc GR . . . .
H25B H 0.203884 -1.375559 0.488050 0.032 Uiso 1 1 calc GR . . . .
H25C H 0.447493 -1.190925 0.486851 0.032 Uiso 1 1 calc GR . . . .
H1 H 0.333(3) 2.893(3) -0.0112(4) 0.061(5) Uiso 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
O1 0.0248(4) 0.0201(4) 0.0142(3) 0.0084(3) -0.0090(3) -0.0108(3)
O2 0.0231(4) 0.0184(4) 0.0155(3) 0.0067(3) -0.0073(3) -0.0098(3)
C1 0.0138(4) 0.0126(4) 0.0126(4) 0.0040(3) -0.0022(3) 0.0008(3)
C2 0.0154(5) 0.0176(5) 0.0157(4) 0.0087(3) -0.0050(3) -0.0065(4)
C3 0.0149(4) 0.0136(4) 0.0116(4) 0.0053(3) -0.0023(3) -0.0038(3)
C4 0.0151(4) 0.0139(4) 0.0143(4) 0.0072(3) -0.0026(3) -0.0040(3)
C5 0.0155(5) 0.0133(4) 0.0122(4) 0.0055(3) -0.0018(3) -0.0036(4)
C6 0.0154(5) 0.0138(4) 0.0136(4) 0.0061(3) -0.0014(3) -0.0038(4)
C7 0.0161(5) 0.0154(5) 0.0129(4) 0.0060(3) -0.0018(3) -0.0040(4)
C8 0.0184(5) 0.0141(4) 0.0114(4) 0.0059(3) -0.0025(3) -0.0048(4)
C9 0.0218(5) 0.0193(5) 0.0161(5) 0.0099(4) -0.0040(4) -0.0057(4)
C10 0.0231(5) 0.0171(5) 0.0145(4) 0.0056(4) -0.0036(4) -0.0023(4)
C11 0.0249(5) 0.0167(5) 0.0126(4) 0.0047(3) -0.0033(4) -0.0015(4)
C12 0.0238(5) 0.0164(5) 0.0134(4) 0.0046(3) -0.0031(4) -0.0012(4)
C13 0.0229(5) 0.0174(5) 0.0139(4) 0.0054(4) -0.0040(4) -0.0017(4)
C14 0.0198(5) 0.0180(5) 0.0161(5) 0.0099(4) -0.0043(4) -0.0052(4)
C15 0.0167(5) 0.0132(4) 0.0119(4) 0.0054(3) -0.0027(3) -0.0036(3)
C16 0.0152(4) 0.0135(4) 0.0129(4) 0.0061(3) -0.0025(3) -0.0035(3)
C17 0.0144(4) 0.0126(4) 0.0132(4) 0.0064(3) -0.0019(3) -0.0026(3)
C18 0.0144(4) 0.0121(4) 0.0131(4) 0.0062(3) -0.0026(3) -0.0021(3)
C19 0.0148(4) 0.0119(4) 0.0130(4) 0.0057(3) -0.0022(3) -0.0029(3)
C20 0.0149(4) 0.0116(4) 0.0134(4) 0.0055(3) -0.0025(3) -0.0020(3)
C21 0.0153(4) 0.0112(4) 0.0137(4) 0.0052(3) -0.0023(3) -0.0025(3)
C22 0.0162(5) 0.0116(4) 0.0144(4) 0.0060(3) -0.0024(3) -0.0016(3)
C23 0.0168(5) 0.0117(4) 0.0140(4) 0.0055(3) -0.0029(3) -0.0025(3)
C24 0.0215(5) 0.0154(5) 0.0158(5) 0.0077(4) -0.0015(4) -0.0016(4)
C25 0.0296(5) 0.0168(5) 0.0181(5) 0.0087(4) -0.0043(4) -0.0027(4)
_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
O1 C1 1.3219(10) . ?
O2 C1 1.2232(11) . ?
C1 C2 1.4977(12) . ?
C2 C3 1.5288(11) . ?
C3 C4 1.5232(11) . ?
C4 C5 1.5249(11) . ?
C5 C6 1.5222(12) . ?
C6 C7 1.5230(11) . ?
C7 C8 1.5196(12) . ?
C8 C9 1.5332(11) . ?
C9 C10 1.4616(12) . ?
C10 C11 1.2028(13) . ?
C11 C12 1.3816(13) . ?
C12 C13 1.2023(13) . ?
C13 C14 1.4640(13) . ?
C14 C15 1.5343(12) . ?
C15 C16 1.5230(12) . ?
C16 C17 1.5232(11) . ?
C17 C18 1.5227(12) . ?
C18 C19 1.5258(11) . ?
C19 C20 1.5238(12) . ?
C20 C21 1.5238(11) . ?
C21 C22 1.5215(12) . ?
C22 C23 1.5228(11) . ?
C23 C24 1.5194(12) . ?
C24 C25 1.5243(12) . ?
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
O1 C1 C2 113.71(8) . . ?
O2 C1 O1 122.80(8) . . ?
O2 C1 C2 123.47(8) . . ?
C1 C2 C3 114.59(7) . . ?
C4 C3 C2 111.60(7) . . ?
C3 C4 C5 113.43(7) . . ?
C6 C5 C4 113.27(7) . . ?
C5 C6 C7 113.91(7) . . ?
C8 C7 C6 113.15(7) . . ?
C7 C8 C9 112.29(7) . . ?
C10 C9 C8 113.27(8) . . ?
C11 C10 C9 178.27(10) . . ?
C10 C11 C12 179.22(10) . . ?
C13 C12 C11 179.47(10) . . ?
C12 C13 C14 177.94(10) . . ?
C13 C14 C15 113.00(7) . . ?
C16 C15 C14 112.29(7) . . ?
C15 C16 C17 113.00(7) . . ?
C18 C17 C16 113.87(7) . . ?
C17 C18 C19 113.67(7) . . ?
C20 C19 C18 113.78(7) . . ?
C19 C20 C21 113.82(7) . . ?
C22 C21 C20 113.78(7) . . ?
C21 C22 C23 114.14(7) . . ?
C24 C23 C22 113.43(7) . . ?
C23 C24 C25 113.60(8) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.910(18) 1.752(18) 2.6581(9) 172.9(15) 2_6;5 yes
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
O1 C1 C2 C3 150.06(8) . . . . ?
O2 C1 C2 C3 -31.47(13) . . . . ?
C1 C2 C3 C4 176.14(7) . . . . ?
C2 C3 C4 C5 170.29(7) . . . . ?
C3 C4 C5 C6 179.15(7) . . . . ?
C4 C5 C6 C7 177.26(7) . . . . ?
C5 C6 C7 C8 -177.64(7) . . . . ?
C6 C7 C8 C9 -177.47(7) . . . . ?
C7 C8 C9 C10 -176.26(7) . . . . ?
C13 C14 C15 C16 176.01(7) . . . . ?
C14 C15 C16 C17 176.28(7) . . . . ?
C15 C16 C17 C18 177.10(7) . . . . ?
C16 C17 C18 C19 178.94(7) . . . . ?
C17 C18 C19 C20 179.31(7) . . . . ?
C18 C19 C20 C21 179.23(7) . . . . ?
C19 C20 C21 C22 178.96(7) . . . . ?
C20 C21 C22 C23 178.57(7) . . . . ?
C21 C22 C23 C24 -179.59(7) . . . . ?
C22 C23 C24 C25 179.25(8) . . . . ?
_iucr_refine_instructions_details
;
TITL 12srv221
CELL 0.6889 4.5738 5.3909 46.6472 88.6499 88.5073 81.4017
ZERR 2 0.0003 0.0003 0.0026 0.0015 0.0014 0.0014
LATT 1
SFAC C H O
DISP C 0.0032 0.0015 10.8482
DISP H -0 0 0.6228
DISP O 0.0108 0.0057 30.1916
UNIT 50 84 4
EQIV $1 1-X,6-Y,-Z
L.S. 9 0 0
PLAN 5
SIZE 0.01 0.04 0.12
TEMP -173.15
HTAB O1 O2_$1
CONF
BOND $h
fmap 2 53
acta
OMIT -2 59
WGHT 0.11
FVAR 0.20258
REM
REM
REM
O1 3 0.25012 2.76982 -0.00177 11.00000 0.02481 0.02008 0.01422 =
0.00843 -0.00898 -0.01078
O2 3 0.53138 2.87853 0.03292 11.00000 0.02309 0.01841 0.01551 =
0.00668 -0.00730 -0.00982
C1 1 0.34985 2.75263 0.02466 11.00000 0.01383 0.01264 0.01262 =
0.00399 -0.00221 0.00076
C2 1 0.21395 2.57029 0.04356 11.00000 0.01537 0.01756 0.01569 =
0.00866 -0.00503 -0.00646
AFIX 23
H2A 2 0.15606 2.43812 0.03145 11.00000 -1.20000
H2B 2 0.03140 2.65948 0.05267 11.00000 -1.20000
AFIX 0
C3 1 0.41482 2.44489 0.06709 11.00000 0.01485 0.01357 0.01163 =
0.00526 -0.00234 -0.00385
AFIX 23
H3A 2 0.59088 2.34394 0.05816 11.00000 -1.20000
H3B 2 0.48346 2.57573 0.07865 11.00000 -1.20000
AFIX 0
C4 1 0.25511 2.27598 0.08664 11.00000 0.01507 0.01394 0.01431 =
0.00725 -0.00257 -0.00395
AFIX 23
H4A 2 0.15625 2.16559 0.07466 11.00000 -1.20000
H4B 2 0.09981 2.38176 0.09792 11.00000 -1.20000
AFIX 0
C5 1 0.45947 2.11348 0.10722 11.00000 0.01545 0.01332 0.01223 =
0.00548 -0.00176 -0.00359
AFIX 23
H5A 2 0.61296 2.00571 0.09595 11.00000 -1.20000
H5B 2 0.56059 2.22367 0.11902 11.00000 -1.20000
AFIX 0
C6 1 0.29831 1.94779 0.12703 11.00000 0.01543 0.01377 0.01359 =
0.00606 -0.00142 -0.00381
AFIX 23
H6A 2 0.18900 1.84400 0.11520 11.00000 -1.20000
H6B 2 0.15134 2.05630 0.13892 11.00000 -1.20000
AFIX 0
C7 1 0.50132 1.77530 0.14675 11.00000 0.01611 0.01537 0.01289 =
0.00605 -0.00182 -0.00397
AFIX 23
H7A 2 0.65341 1.67120 0.13494 11.00000 -1.20000
H7B 2 0.60424 1.87892 0.15922 11.00000 -1.20000
AFIX 0
C8 1 0.33812 1.60387 0.16548 11.00000 0.01837 0.01407 0.01141 =
0.00592 -0.00249 -0.00476
AFIX 23
H8A 2 0.24292 1.49423 0.15308 11.00000 -1.20000
H8B 2 0.18028 1.70719 0.17672 11.00000 -1.20000
AFIX 0
C9 1 0.54428 1.44019 0.18610 11.00000 0.02182 0.01932 0.01612 =
0.00992 -0.00398 -0.00575
AFIX 23
H9A 2 0.70965 1.34608 0.17489 11.00000 -1.20000
H9B 2 0.62933 1.55026 0.19928 11.00000 -1.20000
AFIX 0
C10 1 0.39599 1.26217 0.20303 11.00000 0.02309 0.01707 0.01452 =
0.00562 -0.00363 -0.00226
C11 1 0.27158 1.11325 0.21631 11.00000 0.02488 0.01672 0.01258 =
0.00468 -0.00329 -0.00146
C12 1 0.13141 0.94212 0.23186 11.00000 0.02375 0.01639 0.01337 =
0.00461 -0.00308 -0.00115
C13 1 0.00787 0.79318 0.24521 11.00000 0.02288 0.01741 0.01387 =
0.00539 -0.00401 -0.00168
C14 1 -0.13917 0.61542 0.26241 11.00000 0.01982 0.01795 0.01614 =
0.00990 -0.00428 -0.00519
AFIX 23
H14A 2 -0.22775 0.50621 0.24940 11.00000 -1.20000
H14B 2 -0.30168 0.70990 0.27394 11.00000 -1.20000
AFIX 0
C15 1 0.07117 0.45052 0.28259 11.00000 0.01674 0.01319 0.01185 =
0.00545 -0.00274 -0.00360
AFIX 23
H15A 2 0.22559 0.34652 0.27103 11.00000 -1.20000
H15B 2 0.17045 0.55945 0.29473 11.00000 -1.20000
AFIX 0
C16 1 -0.08939 0.27965 0.30180 11.00000 0.01521 0.01348 0.01294 =
0.00608 -0.00252 -0.00352
AFIX 23
H16A 2 -0.19977 0.17925 0.28965 11.00000 -1.20000
H16B 2 -0.23490 0.38432 0.31422 11.00000 -1.20000
AFIX 0
C17 1 0.11876 0.10260 0.32062 11.00000 0.01441 0.01255 0.01319 =
0.00635 -0.00190 -0.00259
AFIX 23
H17A 2 0.25779 -0.00741 0.30812 11.00000 -1.20000
H17B 2 0.23667 0.20312 0.33196 11.00000 -1.20000
AFIX 0
C18 1 -0.03848 -0.06090 0.34107 11.00000 0.01437 0.01207 0.01307 =
0.00616 -0.00264 -0.00213
AFIX 23
H18A 2 -0.15932 -0.15920 0.32977 11.00000 -1.20000
H18B 2 -0.17466 0.04897 0.35383 11.00000 -1.20000
AFIX 0
C19 1 0.17127 -0.24127 0.35948 11.00000 0.01481 0.01186 0.01299 =
0.00572 -0.00224 -0.00287
AFIX 23
H19A 2 0.30584 -0.35246 0.34671 11.00000 -1.20000
H19B 2 0.29384 -0.14306 0.37059 11.00000 -1.20000
AFIX 0
C20 1 0.01437 -0.40294 0.38022 11.00000 0.01491 0.01157 0.01341 =
0.00551 -0.00250 -0.00197
AFIX 23
H20A 2 -0.11036 -0.49937 0.36913 11.00000 -1.20000
H20B 2 -0.11815 -0.29177 0.39316 11.00000 -1.20000
AFIX 0
C21 1 0.22379 -0.58560 0.39834 11.00000 0.01533 0.01122 0.01371 =
0.00517 -0.00234 -0.00252
AFIX 23
H21A 2 0.35382 -0.69885 0.38541 11.00000 -1.20000
H21B 2 0.35105 -0.48946 0.40916 11.00000 -1.20000
AFIX 0
C22 1 0.06680 -0.74363 0.41942 11.00000 0.01619 0.01160 0.01444 =
0.00597 -0.00240 -0.00157
AFIX 23
H22A 2 -0.06446 -0.83616 0.40862 11.00000 -1.20000
H22B 2 -0.05943 -0.63029 0.43263 11.00000 -1.20000
AFIX 0
C23 1 0.27436 -0.93125 0.43710 11.00000 0.01682 0.01172 0.01401 =
0.00549 -0.00286 -0.00254
AFIX 23
H23A 2 0.40153 -1.04433 0.42393 11.00000 -1.20000
H23B 2 0.40456 -0.83902 0.44807 11.00000 -1.20000
AFIX 0
C24 1 0.11391 -1.08869 0.45787 11.00000 0.02153 0.01536 0.01582 =
0.00766 -0.00146 -0.00156
AFIX 23
H24A 2 -0.01835 -1.17903 0.44692 11.00000 -1.20000
H24B 2 -0.01126 -0.97564 0.47119 11.00000 -1.20000
AFIX 0
C25 1 0.32085 -1.27909 0.47534 11.00000 0.02957 0.01684 0.01811 =
0.00868 -0.00430 -0.00270
AFIX 137
H25A 2 0.44423 -1.39321 0.46234 11.00000 -1.50000
H25B 2 0.20388 -1.37556 0.48805 11.00000 -1.50000
H25C 2 0.44749 -1.19093 0.48685 11.00000 -1.50000
AFIX 0
H1 2 0.33322 2.89278 -0.01115 11.00000 0.06059
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
# start Validation Reply Form
_vrf_PLAT708_1_19srv221
;
PROBLEM: D-H..A Calc 110.4(11), Rep 172.9(15), Dev.. 56.82 Sigma
RESPONSE: The peculiar shape of the molecule creates contradiction between two
CIF "requirements":
- the centre mass of the molecule should be in the unit cell (fulfilled);
and
- the maximum symcode translation supposed to be 5 or less.
In this case the acceptor of the hydrogen bond has symm code 1-x,6-y,-z and
it causes miscalculations and appearance of this "A-alert". In our opinion
the first requirement makes sense, while the second one is just software
restriction, originated, probably from original FORTRAN code.
;
#######################################################################
#
# 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_12_3_19srv220
_database_code_depnum_ccdc_archive 'CCDC 2000837'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record
;
2020-05-04 deposited with the CCDC. 2020-07-20 downloaded from the CCDC.
;
_audit_creation_date 2019-07-12
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2017/1
loop_
_audit_author_email
d.s.yufit@durham.ac.uk
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety '2(C25 H42 O2), C10 H8 N2'
_chemical_formula_sum 'C60 H92 N2 O4'
_chemical_formula_weight 905.35
_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 0.0032 0.0015 '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 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0108 0.0057 '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 5.4415(2)
_cell_length_b 8.9535(4)
_cell_length_c 55.673(3)
_cell_angle_alpha 90
_cell_angle_beta 90.8823(10)
_cell_angle_gamma 90
_cell_volume 2712.1(2)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 9987
_cell_measurement_temperature 100.0
_cell_measurement_theta_max 30.47
_cell_measurement_theta_min 2.23
_shelx_estimated_absorpt_T_max 0.998
_shelx_estimated_absorpt_T_min 0.992
_exptl_absorpt_coefficient_mu 0.064
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.7796
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1545 before and 0.0844after correction.
The Ratio of minimum to maximum transmission is 0.7796.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.109
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description needle
_exptl_crystal_F_000 996
_exptl_crystal_size_max 0.12
_exptl_crystal_size_mid 0.04
_exptl_crystal_size_min 0.03
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0663
_diffrn_reflns_av_unetI/netI 0.0476
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -7
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 78
_diffrn_reflns_limit_l_min -78
_diffrn_reflns_number 47696
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 24.415
_diffrn_reflns_theta_max 28.997
_diffrn_reflns_theta_min 0.709
_diffrn_ambient_temperature 100.0
_diffrn_detector 'Photon counting pixel array'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'Dectris Pilatus 2M'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device 'Fixed \c 3-circle diffractometer'
_diffrn_measurement_device_type 'Fluid Film Devices'
_diffrn_measurement_method '\f and \w rotation with 0.1 degree frames'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator 'Silicon 111'
_diffrn_radiation_probe x-ray
_diffrn_radiation_type synchrotron
_diffrn_radiation_wavelength 0.6889
_diffrn_source Synchrotron
_diffrn_source_type 'Undulator, I19, DLS, RAL'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 7025
_reflns_number_total 7923
_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_bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement ?
_computing_data_collection 'GDA 8.44; generic data acquisition software'
_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 'XS (Sheldrick, 2008)'
_refine_diff_density_max 0.653
_refine_diff_density_min -0.341
_refine_diff_density_rms 0.063
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.069
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 303
_refine_ls_number_reflns 7923
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0562
_refine_ls_R_factor_gt 0.0529
_refine_ls_restrained_S_all 1.069
_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^)+(0.1000P)^2^+0.2400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1510
_refine_ls_wR_factor_ref 0.1553
_refine_special_details ?
_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:
C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B),
C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
C1S(H1S), C2S(H2S), C4S(H4S), C5S(H5S)
2.c Idealised Me refined as rotating group:
C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_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
O1 O 2.31234(12) -1.02535(7) 0.45453(2) 0.02275(16) Uani 1 1 d . . . . .
O2 O 2.54190(11) -0.82297(7) 0.46224(2) 0.01945(15) Uani 1 1 d . . . . .
C1 C 2.35906(15) -0.88017(9) 0.45348(2) 0.01217(16) Uani 1 1 d . . . . .
C2 C 2.15916(14) -0.79788(8) 0.43979(2) 0.01242(16) Uani 1 1 d . . . . .
H2A H 2.000461 -0.816942 0.447692 0.015 Uiso 1 1 calc R . . . .
H2B H 2.147390 -0.839636 0.423347 0.015 Uiso 1 1 calc R . . . .
C3 C 2.19634(14) -0.62979(8) 0.43795(2) 0.01223(16) Uani 1 1 d . . . . .
H3A H 2.353039 -0.609362 0.429769 0.015 Uiso 1 1 calc R . . . .
H3B H 2.208026 -0.586739 0.454311 0.015 Uiso 1 1 calc R . . . .
C4 C 1.98584(14) -0.55442(9) 0.42408(2) 0.01221(16) Uani 1 1 d . . . . .
H4A H 1.976541 -0.596751 0.407665 0.015 Uiso 1 1 calc R . . . .
H4B H 1.829139 -0.577308 0.432101 0.015 Uiso 1 1 calc R . . . .
C5 C 2.01480(14) -0.38502(9) 0.42232(2) 0.01369(16) Uani 1 1 d . . . . .
H5A H 2.027317 -0.342927 0.438740 0.016 Uiso 1 1 calc R . . . .
H5B H 2.169987 -0.362181 0.414031 0.016 Uiso 1 1 calc R . . . .
C6 C 1.80214(15) -0.30918(9) 0.40886(2) 0.01413(16) Uani 1 1 d . . . . .
H6A H 1.794981 -0.347188 0.392168 0.017 Uiso 1 1 calc R . . . .
H6B H 1.645885 -0.336055 0.416648 0.017 Uiso 1 1 calc R . . . .
C7 C 1.82661(15) -0.13935(9) 0.40833(2) 0.01335(16) Uani 1 1 d . . . . .
H7A H 1.982213 -0.112786 0.400396 0.016 Uiso 1 1 calc R . . . .
H7B H 1.836301 -0.101801 0.425043 0.016 Uiso 1 1 calc R . . . .
C8 C 1.61395(15) -0.06135(9) 0.39520(2) 0.01368(16) Uani 1 1 d . . . . .
H8A H 1.458495 -0.082806 0.403541 0.016 Uiso 1 1 calc R . . . .
H8B H 1.599101 -0.100769 0.378628 0.016 Uiso 1 1 calc R . . . .
C9 C 1.65536(15) 0.10821(9) 0.39434(2) 0.01431(17) Uani 1 1 d . . . . .
H9A H 1.671459 0.146254 0.410987 0.017 Uiso 1 1 calc R . . . .
H9B H 1.812221 0.128295 0.386165 0.017 Uiso 1 1 calc R . . . .
C10 C 1.45830(15) 0.19047(9) 0.38194(2) 0.01407(16) Uani 1 1 d . . . . .
C11 C 1.29523(15) 0.25857(9) 0.37191(2) 0.01386(16) Uani 1 1 d . . . . .
C12 C 1.11004(15) 0.33674(9) 0.36046(2) 0.01414(16) Uani 1 1 d . . . . .
C13 C 0.94623(16) 0.40549(9) 0.35076(2) 0.01469(17) Uani 1 1 d . . . . .
C14 C 0.75012(16) 0.48843(9) 0.33833(2) 0.01654(18) Uani 1 1 d . . . . .
H14A H 0.822703 0.575852 0.330178 0.020 Uiso 1 1 calc R . . . .
H14B H 0.633298 0.526207 0.350358 0.020 Uiso 1 1 calc R . . . .
C15 C 0.60845(14) 0.39401(8) 0.31967(2) 0.01159(16) Uani 1 1 d . . . . .
H15A H 0.726195 0.348399 0.308445 0.014 Uiso 1 1 calc R . . . .
H15B H 0.521270 0.312264 0.327951 0.014 Uiso 1 1 calc R . . . .
C16 C 0.42278(15) 0.48806(9) 0.30549(2) 0.01251(16) Uani 1 1 d . . . . .
H16A H 0.511807 0.565259 0.296327 0.015 Uiso 1 1 calc R . . . .
H16B H 0.313572 0.539797 0.316857 0.015 Uiso 1 1 calc R . . . .
C17 C 0.26636(14) 0.39512(9) 0.28809(2) 0.01175(16) Uani 1 1 d . . . . .
H17A H 0.169972 0.321912 0.297375 0.014 Uiso 1 1 calc R . . . .
H17B H 0.376257 0.338529 0.277395 0.014 Uiso 1 1 calc R . . . .
C18 C 0.09031(15) 0.48919(9) 0.27273(2) 0.01256(16) Uani 1 1 d . . . . .
H18A H 0.186865 0.561787 0.263341 0.015 Uiso 1 1 calc R . . . .
H18B H -0.018503 0.546499 0.283434 0.015 Uiso 1 1 calc R . . . .
C19 C -0.06815(14) 0.39626(9) 0.25545(2) 0.01168(16) Uani 1 1 d . . . . .
H19A H 0.040764 0.337262 0.244993 0.014 Uiso 1 1 calc R . . . .
H19B H -0.167269 0.325135 0.264873 0.014 Uiso 1 1 calc R . . . .
C20 C -0.24068(15) 0.49019(9) 0.23968(2) 0.01305(17) Uani 1 1 d . . . . .
H20A H -0.348262 0.550163 0.250130 0.016 Uiso 1 1 calc R . . . .
H20B H -0.141523 0.560393 0.230088 0.016 Uiso 1 1 calc R . . . .
C21 C -0.40102(14) 0.39670(9) 0.22267(2) 0.01212(16) Uani 1 1 d . . . . .
H21A H -0.503408 0.328476 0.232295 0.015 Uiso 1 1 calc R . . . .
H21B H -0.293336 0.334551 0.212553 0.015 Uiso 1 1 calc R . . . .
C22 C -0.56902(15) 0.49012(9) 0.20634(2) 0.01393(17) Uani 1 1 d . . . . .
H22A H -0.674446 0.553819 0.216434 0.017 Uiso 1 1 calc R . . . .
H22B H -0.466586 0.556788 0.196442 0.017 Uiso 1 1 calc R . . . .
C23 C -0.73241(15) 0.39596(9) 0.18976(2) 0.01303(16) Uani 1 1 d . . . . .
H23A H -0.626789 0.331853 0.179755 0.016 Uiso 1 1 calc R . . . .
H23B H -0.835159 0.329614 0.199685 0.016 Uiso 1 1 calc R . . . .
C24 C -0.89994(16) 0.48829(10) 0.17331(2) 0.01776(18) Uani 1 1 d . . . . .
H24A H -0.797451 0.551940 0.162920 0.021 Uiso 1 1 calc R . . . .
H24B H -1.002015 0.554907 0.183247 0.021 Uiso 1 1 calc R . . . .
C25 C -1.06817(17) 0.39207(11) 0.15748(2) 0.02095(19) Uani 1 1 d . . . . .
H25A H -1.171777 0.329679 0.167654 0.031 Uiso 1 1 calc GR . . . .
H25B H -0.968246 0.328097 0.147210 0.031 Uiso 1 1 calc GR . . . .
H25C H -1.172475 0.456683 0.147427 0.031 Uiso 1 1 calc GR . . . .
H1 H 2.452(4) -1.077(2) 0.4625(3) 0.076(6) Uiso 1 1 d . . . . .
N1 N 0.64263(13) 0.79175(8) 0.47373(2) 0.01451(15) Uani 1 1 d . . . . .
C1S C 0.58254(15) 0.64809(9) 0.47061(2) 0.01393(16) Uani 1 1 d . . . . .
H1S H 0.439913 0.625574 0.461244 0.017 Uiso 1 1 calc R . . . .
C2S C 0.71642(15) 0.53027(9) 0.48025(2) 0.01230(16) Uani 1 1 d . . . . .
H2S H 0.666804 0.430063 0.477360 0.015 Uiso 1 1 calc R . . . .
C3S C 0.92644(14) 0.56103(8) 0.49436(2) 0.00996(15) Uani 1 1 d . . . . .
C4S C 0.99141(16) 0.71141(9) 0.49727(2) 0.01552(17) Uani 1 1 d . . . . .
H4S H 1.133723 0.737913 0.506409 0.019 Uiso 1 1 calc R . . . .
C5S C 0.84586(16) 0.82156(9) 0.48668(2) 0.01784(18) Uani 1 1 d . . . . .
H5S H 0.893075 0.922967 0.488737 0.021 Uiso 1 1 calc R . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0201(3) 0.0088(3) 0.0388(4) 0.0056(2) -0.0171(3) -0.0005(2)
O2 0.0157(3) 0.0141(3) 0.0281(3) 0.0020(2) -0.0118(2) -0.0003(2)
C1 0.0122(3) 0.0096(3) 0.0146(3) 0.0015(3) -0.0032(3) 0.0016(3)
C2 0.0110(3) 0.0088(3) 0.0173(4) 0.0013(3) -0.0072(3) 0.0012(3)
C3 0.0110(3) 0.0086(3) 0.0168(4) 0.0016(3) -0.0057(3) 0.0010(3)
C4 0.0120(4) 0.0091(3) 0.0153(4) 0.0010(3) -0.0062(3) 0.0018(3)
C5 0.0117(4) 0.0103(3) 0.0189(4) 0.0030(3) -0.0065(3) 0.0013(3)
C6 0.0131(4) 0.0105(3) 0.0185(4) 0.0026(3) -0.0085(3) 0.0012(3)
C7 0.0122(4) 0.0099(3) 0.0177(4) 0.0039(3) -0.0072(3) 0.0011(3)
C8 0.0116(4) 0.0109(3) 0.0183(4) 0.0032(3) -0.0077(3) 0.0016(3)
C9 0.0120(4) 0.0120(4) 0.0186(4) 0.0046(3) -0.0072(3) 0.0010(3)
C10 0.0140(4) 0.0121(3) 0.0159(4) 0.0028(3) -0.0052(3) 0.0003(3)
C11 0.0144(4) 0.0132(4) 0.0138(3) 0.0024(3) -0.0045(3) 0.0008(3)
C12 0.0144(4) 0.0144(4) 0.0135(3) 0.0012(3) -0.0052(3) 0.0001(3)
C13 0.0161(4) 0.0138(4) 0.0140(4) 0.0002(3) -0.0076(3) 0.0009(3)
C14 0.0180(4) 0.0130(4) 0.0183(4) -0.0010(3) -0.0127(3) 0.0039(3)
C15 0.0118(3) 0.0109(3) 0.0118(3) 0.0008(2) -0.0065(3) 0.0020(3)
C16 0.0129(4) 0.0107(4) 0.0136(3) 0.0008(3) -0.0088(3) 0.0014(3)
C17 0.0115(4) 0.0102(4) 0.0134(3) 0.0006(2) -0.0068(3) 0.0007(3)
C18 0.0129(4) 0.0108(4) 0.0138(4) 0.0003(3) -0.0084(3) 0.0004(3)
C19 0.0114(4) 0.0104(4) 0.0130(4) 0.0004(2) -0.0070(3) 0.0004(3)
C20 0.0133(4) 0.0104(4) 0.0152(4) -0.0002(3) -0.0089(3) 0.0002(3)
C21 0.0118(4) 0.0106(3) 0.0137(4) 0.0000(3) -0.0077(3) 0.0001(3)
C22 0.0141(4) 0.0109(4) 0.0165(4) -0.0002(3) -0.0096(3) 0.0003(3)
C23 0.0123(4) 0.0124(4) 0.0142(4) 0.0001(3) -0.0077(3) -0.0004(3)
C24 0.0190(4) 0.0156(4) 0.0183(4) 0.0005(3) -0.0123(3) 0.0016(3)
C25 0.0191(4) 0.0243(4) 0.0191(4) 0.0007(3) -0.0123(3) -0.0014(3)
N1 0.0158(3) 0.0101(3) 0.0174(3) 0.0017(2) -0.0072(3) 0.0020(2)
C1S 0.0131(4) 0.0119(4) 0.0165(4) 0.0022(3) -0.0074(3) -0.0002(3)
C2S 0.0126(3) 0.0094(3) 0.0147(3) 0.0010(3) -0.0060(3) -0.0006(3)
C3S 0.0107(3) 0.0087(3) 0.0104(3) 0.0008(2) -0.0039(3) 0.0017(3)
C4S 0.0173(4) 0.0095(3) 0.0194(4) 0.0004(3) -0.0106(3) 0.0005(3)
C5S 0.0214(4) 0.0079(3) 0.0238(4) 0.0004(3) -0.0119(3) 0.0006(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
O1 C1 1.3260(10) . ?
O1 H1 0.99(2) . ?
O2 C1 1.2145(10) . ?
C1 C2 1.5104(10) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.5222(10) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5286(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5282(11) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.5281(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.5268(11) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.5281(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5357(11) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.4651(10) . ?
C10 C11 1.2063(11) . ?
C11 C12 1.3756(11) . ?
C12 C13 1.2043(11) . ?
C13 C14 1.4650(11) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.5374(11) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.5260(10) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.5261(10) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.5277(10) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.5281(10) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.5280(10) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.5276(10) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.5284(10) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.5258(10) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5258(10) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.5269(11) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N1 C1S 1.3378(10) . ?
N1 C5S 1.3376(10) . ?
C1S H1S 0.9500 . ?
C1S C2S 1.3856(11) . ?
C2S H2S 0.9500 . ?
C2S C3S 1.4040(10) . ?
C3S C3S 1.4878(14) 3_766 ?
C3S C4S 1.4008(11) . ?
C4S H4S 0.9500 . ?
C4S C5S 1.3905(11) . ?
C5S H5S 0.9500 . ?
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
C1 O1 H1 109.5(13) . . ?
O1 C1 C2 111.31(7) . . ?
O2 C1 O1 123.51(7) . . ?
O2 C1 C2 125.17(7) . . ?
C1 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C1 C2 C3 114.88(6) . . ?
H2A C2 H2B 107.5 . . ?
C3 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C2 C3 C4 111.78(6) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.8 . . ?
C5 C4 C3 113.16(6) . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C4 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 C4 113.23(7) . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
C5 C6 H6A 109.0 . . ?
C5 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C7 C6 C5 112.74(6) . . ?
C7 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C6 C7 C8 113.50(7) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 C9 110.87(6) . . ?
H8A C8 H8B 108.1 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C8 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C10 C9 C8 113.89(7) . . ?
C10 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C11 C10 C9 179.43(9) . . ?
C10 C11 C12 179.73(11) . . ?
C13 C12 C11 179.02(9) . . ?
C12 C13 C14 178.46(9) . . ?
C13 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C13 C14 C15 113.23(7) . . ?
H14A C14 H14B 107.7 . . ?
C15 C14 H14A 108.9 . . ?
C15 C14 H14B 108.9 . . ?
C14 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 C14 111.55(6) . . ?
C16 C15 H15A 109.3 . . ?
C16 C15 H15B 109.3 . . ?
C15 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C15 C16 C17 112.69(6) . . ?
H16A C16 H16B 107.8 . . ?
C17 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C16 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
C16 C17 C18 113.17(6) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 108.9 . . ?
C18 C17 H17B 108.9 . . ?
C17 C18 H18A 108.9 . . ?
C17 C18 H18B 108.9 . . ?
C17 C18 C19 113.28(7) . . ?
H18A C18 H18B 107.7 . . ?
C19 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C18 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 C18 113.44(7) . . ?
C20 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
C19 C20 H20A 108.9 . . ?
C19 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C21 C20 C19 113.25(7) . . ?
C21 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C20 C21 H21A 108.9 . . ?
C20 C21 H21B 108.9 . . ?
C20 C21 C22 113.55(7) . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C21 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C23 C22 C21 113.26(7) . . ?
C23 C22 H22A 108.9 . . ?
C23 C22 H22B 108.9 . . ?
C22 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 C22 113.64(7) . . ?
C24 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C23 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
C23 C24 C25 112.84(7) . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C5S N1 C1S 117.41(7) . . ?
N1 C1S H1S 118.1 . . ?
N1 C1S C2S 123.76(7) . . ?
C2S C1S H1S 118.1 . . ?
C1S C2S H2S 120.5 . . ?
C1S C2S C3S 119.08(7) . . ?
C3S C2S H2S 120.5 . . ?
C2S C3S C3S 121.33(9) . 3_766 ?
C4S C3S C2S 117.07(7) . . ?
C4S C3S C3S 121.61(8) . 3_766 ?
C3S C4S H4S 120.3 . . ?
C5S C4S C3S 119.45(7) . . ?
C5S C4S H4S 120.3 . . ?
N1 C5S C4S 123.21(8) . . ?
N1 C5S H5S 118.4 . . ?
C4S C5S H5S 118.4 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N1 0.99(2) 1.68(2) 2.6449(9) 163.8(19) 1_735 yes
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
O1 C1 C2 C3 179.28(7) . . . . ?
O2 C1 C2 C3 -1.63(11) . . . . ?
C1 C2 C3 C4 -179.48(6) . . . . ?
C2 C3 C4 C5 178.86(7) . . . . ?
C3 C4 C5 C6 -178.93(7) . . . . ?
C4 C5 C6 C7 177.08(7) . . . . ?
C5 C6 C7 C8 -179.30(7) . . . . ?
C6 C7 C8 C9 -177.49(7) . . . . ?
C7 C8 C9 C10 179.89(7) . . . . ?
C13 C14 C15 C16 -174.56(7) . . . . ?
C14 C15 C16 C17 -175.82(7) . . . . ?
C15 C16 C17 C18 -176.59(6) . . . . ?
C16 C17 C18 C19 -179.49(7) . . . . ?
C17 C18 C19 C20 -178.79(6) . . . . ?
C18 C19 C20 C21 -179.27(7) . . . . ?
C19 C20 C21 C22 -178.40(7) . . . . ?
C20 C21 C22 C23 -178.81(7) . . . . ?
C21 C22 C23 C24 -179.72(7) . . . . ?
C22 C23 C24 C25 -178.01(7) . . . . ?
N1 C1S C2S C3S 0.66(13) . . . . ?
C1S N1 C5S C4S -1.46(13) . . . . ?
C1S C2S C3S C3S 178.53(9) . . . 3_766 ?
C1S C2S C3S C4S -1.67(11) . . . . ?
C2S C3S C4S C5S 1.18(12) . . . . ?
C3S C3S C4S C5S -179.03(9) 3_766 . . . ?
C3S C4S C5S N1 0.41(14) . . . . ?
C5S N1 C1S C2S 0.93(13) . . . . ?
_iucr_refine_instructions_details
;
TITL P_BPY in P21/c #14
REM reset to P21/c #14
CELL 0.6889 5.4415 8.9535 55.6735 90 90.8823 90
ZERR 2 0.0002 0.0004 0.0026 0 0.001 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
DISP C 0.0032 0.0015 10.8482
DISP H -0 0 0.6228
DISP N 0.006 0.003 18.3366
DISP O 0.0108 0.0057 30.1916
UNIT 120 184 4 8
EQIV $1 2+X,-2+Y,+Z
L.S. 9 0 0
PLAN 5
SIZE 0.03 0.04 0.12
TEMP -173.15
HTAB O1 N1_$1
BOND $h
CONF
fmap 2 53
acta
OMIT -2 58
OMIT -1 2 16
OMIT -1 1 5
WGHT 0.1 0.24
FVAR 0.10565
REM
REM
REM
O1 4 2.31234 -1.02535 0.45453 11.00000 0.02006 0.00881 0.03885 =
0.00561 -0.01706 -0.00050
O2 4 2.54190 -0.82297 0.46224 11.00000 0.01574 0.01414 0.02809 =
0.00202 -0.01176 -0.00033
C1 1 2.35907 -0.88017 0.45348 11.00000 0.01223 0.00960 0.01459 =
0.00153 -0.00321 0.00156
C2 1 2.15916 -0.79788 0.43979 11.00000 0.01099 0.00876 0.01729 =
0.00125 -0.00719 0.00116
AFIX 23
H2a 2 2.00046 -0.81694 0.44769 11.00000 -1.20000
H2b 2 2.14739 -0.83964 0.42335 11.00000 -1.20000
AFIX 0
C3 1 2.19634 -0.62979 0.43795 11.00000 0.01103 0.00864 0.01684 =
0.00159 -0.00566 0.00103
AFIX 23
H3a 2 2.35304 -0.60936 0.42977 11.00000 -1.20000
H3b 2 2.20803 -0.58674 0.45431 11.00000 -1.20000
AFIX 0
C4 1 1.98584 -0.55442 0.42408 11.00000 0.01198 0.00914 0.01531 =
0.00100 -0.00616 0.00182
AFIX 23
H4a 2 1.97654 -0.59675 0.40767 11.00000 -1.20000
H4b 2 1.82914 -0.57731 0.43210 11.00000 -1.20000
AFIX 0
C5 1 2.01480 -0.38502 0.42232 11.00000 0.01166 0.01030 0.01890 =
0.00301 -0.00647 0.00131
AFIX 23
H5a 2 2.16999 -0.36218 0.41403 11.00000 -1.20000
H5b 2 2.02732 -0.34293 0.43874 11.00000 -1.20000
AFIX 0
C6 1 1.80214 -0.30918 0.40886 11.00000 0.01310 0.01052 0.01849 =
0.00257 -0.00849 0.00121
AFIX 23
H6a 2 1.79498 -0.34719 0.39217 11.00000 -1.20000
H6b 2 1.64589 -0.33605 0.41665 11.00000 -1.20000
AFIX 0
C7 1 1.82661 -0.13935 0.40833 11.00000 0.01221 0.00991 0.01769 =
0.00385 -0.00718 0.00110
AFIX 23
H7a 2 1.98221 -0.11279 0.40040 11.00000 -1.20000
H7b 2 1.83630 -0.10180 0.42504 11.00000 -1.20000
AFIX 0
C8 1 1.61395 -0.06136 0.39520 11.00000 0.01160 0.01091 0.01829 =
0.00321 -0.00771 0.00162
AFIX 23
H8a 2 1.45850 -0.08281 0.40354 11.00000 -1.20000
H8b 2 1.59910 -0.10077 0.37863 11.00000 -1.20000
AFIX 0
C9 1 1.65536 0.10821 0.39434 11.00000 0.01205 0.01204 0.01861 =
0.00459 -0.00719 0.00099
AFIX 23
H9a 2 1.67146 0.14625 0.41099 11.00000 -1.20000
H9b 2 1.81222 0.12829 0.38616 11.00000 -1.20000
AFIX 0
C10 1 1.45830 0.19047 0.38194 11.00000 0.01400 0.01209 0.01594 =
0.00281 -0.00518 0.00032
C11 1 1.29523 0.25857 0.37191 11.00000 0.01444 0.01322 0.01380 =
0.00236 -0.00446 0.00076
C12 1 1.11004 0.33674 0.36046 11.00000 0.01440 0.01436 0.01348 =
0.00122 -0.00517 0.00014
C13 1 0.94623 0.40549 0.35076 11.00000 0.01606 0.01377 0.01402 =
0.00017 -0.00760 0.00089
C14 1 0.75012 0.48843 0.33833 11.00000 0.01796 0.01295 0.01830 =
-0.00104 -0.01267 0.00391
AFIX 23
H14a 2 0.82270 0.57585 0.33018 11.00000 -1.20000
H14b 2 0.63330 0.52621 0.35036 11.00000 -1.20000
AFIX 0
C15 1 0.60845 0.39401 0.31967 11.00000 0.01185 0.01091 0.01182 =
0.00080 -0.00650 0.00202
AFIX 23
H15a 2 0.72620 0.34840 0.30845 11.00000 -1.20000
H15b 2 0.52127 0.31226 0.32795 11.00000 -1.20000
AFIX 0
C16 1 0.42278 0.48806 0.30549 11.00000 0.01294 0.01070 0.01362 =
0.00081 -0.00885 0.00138
AFIX 23
H16a 2 0.51181 0.56526 0.29633 11.00000 -1.20000
H16b 2 0.31357 0.53980 0.31686 11.00000 -1.20000
AFIX 0
C17 1 0.26636 0.39512 0.28809 11.00000 0.01149 0.01018 0.01336 =
0.00064 -0.00683 0.00073
AFIX 23
H17a 2 0.16997 0.32191 0.29738 11.00000 -1.20000
H17b 2 0.37626 0.33853 0.27740 11.00000 -1.20000
AFIX 0
C18 1 0.09031 0.48919 0.27273 11.00000 0.01289 0.01076 0.01377 =
0.00032 -0.00840 0.00042
AFIX 23
H18a 2 0.18687 0.56179 0.26334 11.00000 -1.20000
H18b 2 -0.01850 0.54650 0.28343 11.00000 -1.20000
AFIX 0
C19 1 -0.06815 0.39626 0.25545 11.00000 0.01140 0.01039 0.01303 =
0.00039 -0.00698 0.00038
AFIX 23
H19a 2 0.04076 0.33726 0.24499 11.00000 -1.20000
H19b 2 -0.16727 0.32514 0.26487 11.00000 -1.20000
AFIX 0
C20 1 -0.24068 0.49019 0.23968 11.00000 0.01325 0.01037 0.01524 =
-0.00018 -0.00891 0.00020
AFIX 23
H20a 2 -0.14152 0.56039 0.23009 11.00000 -1.20000
H20b 2 -0.34826 0.55016 0.25013 11.00000 -1.20000
AFIX 0
C21 1 -0.40102 0.39670 0.22267 11.00000 0.01179 0.01060 0.01371 =
0.00001 -0.00769 0.00006
AFIX 23
H21a 2 -0.29334 0.33455 0.21255 11.00000 -1.20000
H21b 2 -0.50341 0.32848 0.23230 11.00000 -1.20000
AFIX 0
C22 1 -0.56902 0.49012 0.20634 11.00000 0.01410 0.01089 0.01648 =
-0.00020 -0.00957 0.00028
AFIX 23
H22a 2 -0.67445 0.55382 0.21643 11.00000 -1.20000
H22b 2 -0.46659 0.55679 0.19644 11.00000 -1.20000
AFIX 0
C23 1 -0.73242 0.39596 0.18976 11.00000 0.01232 0.01237 0.01416 =
0.00011 -0.00773 -0.00040
AFIX 23
H23a 2 -0.62679 0.33185 0.17976 11.00000 -1.20000
H23b 2 -0.83516 0.32961 0.19969 11.00000 -1.20000
AFIX 0
C24 1 -0.89994 0.48829 0.17331 11.00000 0.01899 0.01559 0.01833 =
0.00053 -0.01228 0.00159
AFIX 23
H24a 2 -0.79745 0.55194 0.16292 11.00000 -1.20000
H24b 2 -1.00202 0.55491 0.18325 11.00000 -1.20000
AFIX 0
C25 1 -1.06817 0.39207 0.15748 11.00000 0.01907 0.02427 0.01911 =
0.00071 -0.01228 -0.00139
AFIX 137
H25a 2 -1.17178 0.32968 0.16765 11.00000 -1.50000
H25b 2 -0.96825 0.32810 0.14721 11.00000 -1.50000
H25c 2 -1.17247 0.45668 0.14743 11.00000 -1.50000
AFIX 0
H1 2 2.45186 -1.07722 0.46247 11.00000 0.07581
N1 3 0.64263 0.79175 0.47373 11.00000 0.01578 0.01012 0.01739 =
0.00172 -0.00718 0.00203
C1S 1 0.58254 0.64809 0.47061 11.00000 0.01309 0.01192 0.01655 =
0.00218 -0.00738 -0.00018
AFIX 43
H1S 2 0.43991 0.62557 0.46124 11.00000 -1.20000
AFIX 0
C2S 1 0.71642 0.53027 0.48025 11.00000 0.01260 0.00942 0.01470 =
0.00105 -0.00598 -0.00061
AFIX 43
H2S 2 0.66680 0.43006 0.47736 11.00000 -1.20000
AFIX 0
C3S 1 0.92644 0.56103 0.49437 11.00000 0.01069 0.00871 0.01036 =
0.00084 -0.00391 0.00168
C4S 1 0.99141 0.71141 0.49727 11.00000 0.01730 0.00951 0.01941 =
0.00037 -0.01057 0.00049
AFIX 43
H4S 2 1.13372 0.73791 0.50641 11.00000 -1.20000
AFIX 0
C5S 1 0.84586 0.82156 0.48668 11.00000 0.02144 0.00791 0.02379 =
0.00044 -0.01190 0.00061
AFIX 43
H5S 2 0.89307 0.92297 0.48874 11.00000 -1.20000
AFIX 0
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# 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_1_6_19srv296
_database_code_depnum_ccdc_archive 'CCDC 2000832'
loop_
_audit_author_name
_audit_author_address
'Dmitry Yufit'
;Durham University
United Kingdom
;
_audit_update_record
;
2020-05-04 deposited with the CCDC. 2020-07-20 downloaded from the CCDC.
;
_audit_creation_date 2019-10-04
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2017/1
loop_
_audit_author_email
d.s.yufit@durham.ac.uk
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C4 H7 O2, C4 H10 N O'
_chemical_formula_sum 'C8 H17 N O3'
_chemical_formula_weight 175.22
_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 0.0033 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'
_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 15
_space_group_name_H-M_alt 'C 1 2/c 1'
_space_group_name_Hall '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 20.0926(14)
_cell_length_b 8.0678(6)
_cell_length_c 11.6061(8)
_cell_angle_alpha 90
_cell_angle_beta 97.064(3)
_cell_angle_gamma 90
_cell_volume 1867.1(2)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 7317
_cell_measurement_temperature 120.0
_cell_measurement_theta_max 31.47
_cell_measurement_theta_min 2.72
_shelx_estimated_absorpt_T_max 0.981
_shelx_estimated_absorpt_T_min 0.960
_exptl_absorpt_coefficient_mu 0.094
_exptl_absorpt_correction_T_max 1.0000
_exptl_absorpt_correction_T_min 0.8943
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1051 before and 0.0421 after correction.
The Ratio of minimum to maximum transmission is 0.8943.
The \l/2 correction factor is Not present.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear colourless'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_primary colourless
_exptl_crystal_density_diffrn 1.247
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 768
_exptl_crystal_size_max 0.44
_exptl_crystal_size_mid 0.25
_exptl_crystal_size_min 0.21
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0313
_diffrn_reflns_av_unetI/netI 0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 27
_diffrn_reflns_limit_h_min -27
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 13471
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 29.497
_diffrn_reflns_theta_min 2.723
_diffrn_ambient_temperature 120.0
_diffrn_detector 'Bruker PHOTON 100 CMOS'
_diffrn_detector_area_resol_mean 10.4
_diffrn_detector_type 'CMOS sensor'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device '3-circle diffractometer'
_diffrn_measurement_device_type 'Bruker D8 Venture'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_monochromator 'focusing mirrors'
_diffrn_radiation_probe X-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'microfocus sealed X-ray tube'
_diffrn_source_type 'Incoatec I\mS microsource'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 2060
_reflns_number_total 2587
_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_bruker_data_scaling 'SADABS V2012/1 (Bruker AXS Inc.)'
_computing_cell_refinement 'SAINT v8.38A (Bruker AXS, 2016)'
_computing_data_collection 'APEX3 v.2017.3_0 (Bruker AXS, 2017)'
_computing_data_reduction 'SAINT v8.38A (Bruker AXS, 2016)'
_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 'XS (Sheldrick, 2008)'
_refine_diff_density_max 0.361
_refine_diff_density_min -0.198
_refine_diff_density_rms 0.044
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.023
_refine_ls_hydrogen_treatment refall
_refine_ls_matrix_type full
_refine_ls_number_parameters 177
_refine_ls_number_reflns 2587
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0505
_refine_ls_R_factor_gt 0.0356
_refine_ls_restrained_S_all 1.023
_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^)+(0.0610P)^2^+0.4700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0931
_refine_ls_wR_factor_ref 0.1011
_refine_special_details ?
_olex2_refinement_description
;
;
_atom_sites_solution_hydrogens difmap
_atom_sites_solution_primary direct
_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
O1 O 0.20176(3) 0.52110(10) 0.21686(6) 0.02317(18) Uani 1 1 d . . . . .
O2 O 0.27758(3) 0.44727(10) 0.10205(6) 0.02516(19) Uani 1 1 d . . . . .
C1 C 0.26107(5) 0.49257(12) 0.19833(8) 0.0169(2) Uani 1 1 d . . . . .
C2 C 0.31702(5) 0.52136(13) 0.29776(8) 0.0183(2) Uani 1 1 d . . . . .
C3 C 0.38272(5) 0.43454(13) 0.28497(8) 0.0181(2) Uani 1 1 d . . . . .
C4 C 0.43913(5) 0.49128(14) 0.37645(10) 0.0236(2) Uani 1 1 d . . . . .
H2A H 0.3008(6) 0.4896(15) 0.3687(12) 0.025(3) Uiso 1 1 d . . . . .
H2B H 0.3232(6) 0.6426(17) 0.3011(10) 0.028(3) Uiso 1 1 d . . . . .
H3A H 0.3758(6) 0.3130(17) 0.2903(10) 0.027(3) Uiso 1 1 d . . . . .
H3B H 0.3956(6) 0.4578(14) 0.2065(11) 0.017(3) Uiso 1 1 d . . . . .
H4A H 0.4478(6) 0.6120(17) 0.3698(11) 0.028(3) Uiso 1 1 d . . . . .
H4B H 0.4820(7) 0.4316(18) 0.3650(12) 0.039(4) Uiso 1 1 d . . . . .
H4C H 0.4276(7) 0.4710(16) 0.4540(13) 0.036(4) Uiso 1 1 d . . . . .
O3 O 0.03524(3) 0.41949(10) 0.39721(6) 0.02511(19) Uani 1 1 d . . . . .
N1 N 0.17150(4) 0.52441(11) 0.44001(7) 0.01714(18) Uani 1 1 d . . . . .
C5 C 0.15221(5) 0.34688(13) 0.44330(9) 0.0237(2) Uani 1 1 d . . . . .
C6 C 0.08779(5) 0.31946(14) 0.36362(9) 0.0249(2) Uani 1 1 d . . . . .
C7 C 0.05219(5) 0.58958(14) 0.38868(9) 0.0214(2) Uani 1 1 d . . . . .
C8 C 0.11544(5) 0.63203(12) 0.46736(8) 0.0173(2) Uani 1 1 d . . . . .
H1A H 0.1838(7) 0.5457(16) 0.3678(13) 0.032(3) Uiso 1 1 d . . . . .
H1B H 0.2096(7) 0.5378(17) 0.4948(13) 0.037(4) Uiso 1 1 d . . . . .
H5A H 0.1466(6) 0.3189(16) 0.5243(12) 0.032(3) Uiso 1 1 d . . . . .
H5B H 0.1882(7) 0.2842(17) 0.4185(11) 0.032(3) Uiso 1 1 d . . . . .
H6A H 0.0935(6) 0.3466(16) 0.2856(12) 0.026(3) Uiso 1 1 d . . . . .
H6B H 0.0734(6) 0.2044(17) 0.3694(11) 0.032(3) Uiso 1 1 d . . . . .
H7A H 0.0144(6) 0.6537(16) 0.4115(11) 0.028(3) Uiso 1 1 d . . . . .
H7B H 0.0588(5) 0.6126(15) 0.3101(10) 0.019(3) Uiso 1 1 d . . . . .
H8A H 0.1107(6) 0.6116(16) 0.5486(11) 0.024(3) Uiso 1 1 d . . . . .
H8B H 0.1288(6) 0.7449(15) 0.4560(10) 0.019(3) Uiso 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
O1 0.0147(3) 0.0406(4) 0.0138(3) -0.0017(3) 0.0001(2) 0.0012(3)
O2 0.0183(3) 0.0447(5) 0.0121(3) -0.0057(3) 0.0001(3) 0.0015(3)
C1 0.0162(4) 0.0220(5) 0.0118(4) 0.0010(3) -0.0003(3) -0.0021(3)
C2 0.0150(4) 0.0271(5) 0.0122(4) -0.0027(4) -0.0007(3) -0.0007(3)
C3 0.0160(4) 0.0203(5) 0.0173(5) -0.0012(4) -0.0003(3) -0.0009(3)
C4 0.0180(5) 0.0256(6) 0.0249(5) -0.0008(4) -0.0062(4) 0.0007(4)
O3 0.0206(4) 0.0295(4) 0.0261(4) -0.0036(3) 0.0063(3) -0.0083(3)
N1 0.0144(4) 0.0250(4) 0.0117(4) -0.0004(3) 0.0001(3) 0.0015(3)
C5 0.0306(5) 0.0205(5) 0.0199(5) -0.0012(4) 0.0022(4) 0.0072(4)
C6 0.0315(5) 0.0219(5) 0.0218(5) -0.0056(4) 0.0052(4) -0.0049(4)
C7 0.0155(4) 0.0258(5) 0.0225(5) 0.0022(4) 0.0014(3) 0.0016(4)
C8 0.0186(4) 0.0174(4) 0.0159(4) -0.0006(3) 0.0024(3) 0.0015(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
O1 C1 1.2579(11) . ?
O2 C1 1.2584(11) . ?
C1 C2 1.5266(12) . ?
C2 C3 1.5177(13) . ?
C2 H2A 0.957(13) . ?
C2 H2B 0.986(14) . ?
C3 C4 1.5250(13) . ?
C3 H3A 0.993(14) . ?
C3 H3B 0.994(12) . ?
C4 H4A 0.994(13) . ?
C4 H4B 1.009(14) . ?
C4 H4C 0.970(15) . ?
O3 C6 1.4211(13) . ?
O3 C7 1.4203(13) . ?
N1 C5 1.4855(14) . ?
N1 C8 1.4871(12) . ?
N1 H1A 0.919(14) . ?
N1 H1B 0.940(15) . ?
C5 C6 1.5117(15) . ?
C5 H5A 0.986(14) . ?
C5 H5B 0.956(14) . ?
C6 H6A 0.952(13) . ?
C6 H6B 0.977(14) . ?
C7 C8 1.5103(13) . ?
C7 H7A 0.982(13) . ?
C7 H7B 0.956(12) . ?
C8 H8A 0.974(13) . ?
C8 H8B 0.963(12) . ?
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
O1 C1 O2 124.31(8) . . ?
O1 C1 C2 117.90(8) . . ?
O2 C1 C2 117.74(8) . . ?
C1 C2 H2A 108.2(8) . . ?
C1 C2 H2B 104.9(7) . . ?
C3 C2 C1 115.11(8) . . ?
C3 C2 H2A 110.7(7) . . ?
C3 C2 H2B 110.8(7) . . ?
H2A C2 H2B 106.6(10) . . ?
C2 C3 C4 111.98(8) . . ?
C2 C3 H3A 108.7(7) . . ?
C2 C3 H3B 109.2(7) . . ?
C4 C3 H3A 110.5(7) . . ?
C4 C3 H3B 109.1(7) . . ?
H3A C3 H3B 107.3(9) . . ?
C3 C4 H4A 111.2(7) . . ?
C3 C4 H4B 109.8(8) . . ?
C3 C4 H4C 110.7(9) . . ?
H4A C4 H4B 107.2(11) . . ?
H4A C4 H4C 107.6(10) . . ?
H4B C4 H4C 110.2(11) . . ?
C7 O3 C6 109.69(7) . . ?
C5 N1 C8 110.52(8) . . ?
C5 N1 H1A 107.7(8) . . ?
C5 N1 H1B 106.7(9) . . ?
C8 N1 H1A 112.4(8) . . ?
C8 N1 H1B 111.3(8) . . ?
H1A N1 H1B 108.0(12) . . ?
N1 C5 C6 109.38(8) . . ?
N1 C5 H5A 107.8(8) . . ?
N1 C5 H5B 107.0(8) . . ?
C6 C5 H5A 111.1(8) . . ?
C6 C5 H5B 111.2(8) . . ?
H5A C5 H5B 110.2(11) . . ?
O3 C6 C5 110.99(8) . . ?
O3 C6 H6A 108.1(8) . . ?
O3 C6 H6B 106.5(8) . . ?
C5 C6 H6A 110.7(8) . . ?
C5 C6 H6B 109.6(8) . . ?
H6A C6 H6B 110.8(11) . . ?
O3 C7 C8 111.60(8) . . ?
O3 C7 H7A 106.9(8) . . ?
O3 C7 H7B 108.5(7) . . ?
C8 C7 H7A 109.8(8) . . ?
C8 C7 H7B 109.1(7) . . ?
H7A C7 H7B 111.0(10) . . ?
N1 C8 C7 109.98(8) . . ?
N1 C8 H8A 106.0(7) . . ?
N1 C8 H8B 107.0(7) . . ?
C7 C8 H8A 111.8(7) . . ?
C7 C8 H8B 111.1(7) . . ?
H8A C8 H8B 110.8(10) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O1 0.919(14) 1.842(15) 2.7322(11) 162.5(12) . yes
N1 H1B O2 0.940(15) 1.735(15) 2.6731(10) 176.1(13) 6_566 yes
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
O1 C1 C2 C3 160.91(9) . . . . ?
O2 C1 C2 C3 -21.46(13) . . . . ?
C1 C2 C3 C4 170.58(9) . . . . ?
O3 C7 C8 N1 56.63(11) . . . . ?
N1 C5 C6 O3 -58.94(11) . . . . ?
C5 N1 C8 C7 -53.32(10) . . . . ?
C6 O3 C7 C8 -60.75(10) . . . . ?
C7 O3 C6 C5 61.90(11) . . . . ?
C8 N1 C5 C6 54.39(11) . . . . ?
_iucr_refine_instructions_details
;
TITL 19srv296 in C2/c #15
REM reset to C2/c #15
CELL 0.71073 20.0926 8.0678 11.6061 90 97.0639 90
ZERR 8 0.0014 0.0006 0.0008 0 0.003 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H N O
UNIT 64 136 8 24
EQIV $1 +X,1-Y,0.5+Z
L.S. 9 0 0
PLAN 5
SIZE 0.21 0.25 0.44
TEMP -153.15
HTAB N1 O1
HTAB N1 O2_$1
CONF
BOND $h
fmap 2 53
acta
OMIT -2 59
WGHT 0.061 0.47
FVAR 0.17942
REM
REM
REM
O1 4 0.20176 0.52110 0.21686 11.00000 0.01471 0.04063 0.01375 =
-0.00174 0.00011 0.00121
O2 4 0.27758 0.44727 0.10205 11.00000 0.01825 0.04467 0.01210 =
-0.00572 0.00011 0.00154
C1 1 0.26107 0.49258 0.19833 11.00000 0.01614 0.02206 0.01183 =
0.00096 -0.00036 -0.00214
C2 1 0.31702 0.52137 0.29777 11.00000 0.01499 0.02709 0.01217 =
-0.00268 -0.00072 -0.00074
C3 1 0.38272 0.43454 0.28497 11.00000 0.01600 0.02034 0.01735 =
-0.00122 -0.00031 -0.00090
C4 1 0.43913 0.49128 0.37645 11.00000 0.01801 0.02559 0.02489 =
-0.00078 -0.00621 0.00073
H2a 2 0.30077 0.48960 0.36875 11.00000 0.02513
H2b 2 0.32316 0.64265 0.30113 11.00000 0.02828
H3a 2 0.37583 0.31308 0.29035 11.00000 0.02671
H3b 2 0.39556 0.45779 0.20651 11.00000 0.01655
H4a 2 0.44784 0.61193 0.36975 11.00000 0.02801
H4b 2 0.48196 0.43161 0.36503 11.00000 0.03881
H4c 2 0.42761 0.47093 0.45399 11.00000 0.03596
O3 4 0.03523 0.41949 0.39721 11.00000 0.02056 0.02953 0.02608 =
-0.00357 0.00630 -0.00832
N1 3 0.17151 0.52441 0.44001 11.00000 0.01437 0.02495 0.01171 =
-0.00041 0.00007 0.00152
C5 1 0.15221 0.34688 0.44330 11.00000 0.03057 0.02046 0.01993 =
-0.00117 0.00220 0.00719
C6 1 0.08778 0.31946 0.36362 11.00000 0.03142 0.02190 0.02186 =
-0.00559 0.00521 -0.00493
C7 1 0.05219 0.58958 0.38868 11.00000 0.01554 0.02580 0.02248 =
0.00220 0.00139 0.00154
C8 1 0.11545 0.63203 0.46736 11.00000 0.01857 0.01736 0.01595 =
-0.00057 0.00236 0.00147
H1a 2 0.18375 0.54567 0.36779 11.00000 0.03144
H1b 2 0.20957 0.53772 0.49482 11.00000 0.03694
H5a 2 0.14656 0.31892 0.52426 11.00000 0.03147
H5b 2 0.18818 0.28416 0.41847 11.00000 0.03245
H6a 2 0.09349 0.34661 0.28564 11.00000 0.02625
H6b 2 0.07338 0.20445 0.36934 11.00000 0.03175
H7a 2 0.01439 0.65369 0.41154 11.00000 0.02801
H7b 2 0.05884 0.61260 0.31011 11.00000 0.01909
H8a 2 0.11068 0.61157 0.54861 11.00000 0.02385
H8b 2 0.12878 0.74493 0.45600 11.00000 0.01855
HKLF 4
END
;
_olex2_submission_special_instructions 'No special instructions were received'