# 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).
# 
# 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_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 λ/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       'φ and ω 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 > 2σ(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/[σ²(Fo²)+(0.0890P)²+0.8900P] where P=(Fo²+2Fc²)/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 . . .


_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) . . . . ?


_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 λ/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       'φ and ω 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 > 2σ(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/[σ²(Fo²)+(0.0530P)²+0.2900P] where P=(Fo²+2Fc²)/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


_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'
####################################################################### 
# 
# 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 λ/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       'φ and ω 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 > 2σ(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+0.001xFc²λ³/sin(2θ)]^-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/[σ²(Fo²)+(0.0270P)²+2.3500P] where P=(Fo²+2Fc²)/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 . . . .


_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'
####################################################################### 
# 
# 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 λ/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       'φ and ω 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 > 2σ(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/[σ²(Fo²)+(0.0380P)²+1.4200P] where P=(Fo²+2Fc²)/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 . . . . .


_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 ?


_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 λ/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 ω-scans (scan 
width 0.5°, 25s exposure), every run at a different φ angle.
Two runs of 358 φ-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       'φ and ω 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 > 2σ(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/[σ²(Fo²)+(0.0649P)²+0.3367P] where P=(Fo²+2Fc²)/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 . . .


_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) . . . . ?

####################################################################### 
# 
# 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 λ/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 χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'φ and ω 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 > 2σ(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/[σ²(Fo²)+(0.1100P)²] where P=(Fo²+2Fc²)/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 . . . . .


_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) . . . . ?

_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 λ/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 χ 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'φ and ω 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 > 2σ(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/[σ²(Fo²)+(0.1000P)²+0.2400P] where P=(Fo²+2Fc²)/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 . . . .


_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) . . . . ?


_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 λ/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       'φ and ω 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 > 2σ(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/[σ²(Fo²)+(0.0610P)²+0.4700P] where P=(Fo²+2Fc²)/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 . . . . .


_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) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
