data_9242

#Crystallographer: Michael R. Gau

_audit_creation_date               2018-09-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2017/1'
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
;
_chemical_formula_moiety           'C20 H27 N O6'
_chemical_formula_sum              'C20 H27 N O6'
_chemical_formula_weight           377.42

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'

_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                     6.0300(2)
_cell_length_b                     19.3547(8)
_cell_length_c                     9.0029(3)
_cell_angle_alpha                  90
_cell_angle_beta                   102.4530(10)
_cell_angle_gamma                  90
_cell_volume                       1026.00(6)
_cell_formula_units_Z              2
_cell_measurement_reflns_used      9944
_cell_measurement_temperature      100
_cell_measurement_theta_max        25.392
_cell_measurement_theta_min        3.131
_exptl_absorpt_coefficient_mu      0.090
_exptl_absorpt_correction_T_max    0.7452
_exptl_absorpt_correction_T_min    0.7155
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     'SADABS v2016/2'
_exptl_crystal_colour              colorless
_exptl_crystal_density_diffrn      1.222
_exptl_crystal_description         bar
_exptl_crystal_F_000               404
_exptl_crystal_size_max            0.49
_exptl_crystal_size_mid            0.11
_exptl_crystal_size_min            0.07
_diffrn_reflns_av_R_equivalents    0.0254
_diffrn_reflns_av_unetI/netI       0.0203
_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         22
_diffrn_reflns_limit_k_min         -23
_diffrn_reflns_limit_l_max         10
_diffrn_reflns_limit_l_min         -10
_diffrn_reflns_number              16695
_diffrn_reflns_point_group_measured_fraction_full  0.993
_diffrn_reflns_point_group_measured_fraction_max  0.992
_diffrn_reflns_theta_full          25.242
_diffrn_reflns_theta_max           25.392
_diffrn_reflns_theta_min           3.131
_diffrn_ambient_temperature        100
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.998
_diffrn_measurement_device         'CMOS area detector'
_diffrn_measurement_device_type    'Bruker D8QUEST'
_diffrn_measurement_method         'ω and φ scans'
_diffrn_radiation_monochromator    graphite
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     'sealed tube'
_reflns_Friedel_coverage           0.925
_reflns_Friedel_fraction_full      0.987
_reflns_Friedel_fraction_max       0.985
_reflns_number_gt                  3630
_reflns_number_total               3746
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.38A (2016)'
_computing_data_collection         'Bruker APEX3 v2016.1-0'
_computing_data_reduction          'SAINT V8.38A (2016)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.180
_refine_diff_density_min           -0.283
_refine_diff_density_rms           0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 1669 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     0.2(2)
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.162
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       250
_refine_ls_number_reflns           3746
_refine_ls_number_restraints       1
_refine_ls_R_factor_all            0.0296
_refine_ls_R_factor_gt             0.0279
_refine_ls_restrained_S_all        1.162
_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)+(0.0367P)²+0.0896P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0653
_refine_ls_wR_factor_ref           0.0664
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual

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 0.7324(2) 0.53533(7) 0.80231(14) 0.0137(3) Uani 1 1 d . . . . .
 O2 O 0.4108(2) 0.56611(7) 0.87585(15) 0.0166(3) Uani 1 1 d . . . . .
 O3 O 0.6732(2) 0.36786(7) 0.87304(14) 0.0145(3) Uani 1 1 d . . . . .
 O4 O 0.7877(2) 0.32694(7) 0.66566(15) 0.0165(3) Uani 1 1 d . . . . .
 O5 O 0.4487(2) 0.50125(7) 0.47330(15) 0.0157(3) Uani 1 1 d . . . . .
 O6 O 0.6875(2) 0.41631(8) 0.43064(16) 0.0233(3) Uani 1 1 d . . . . .
 N1 N 0.5543(3) 0.42246(8) 0.65288(18) 0.0120(3) Uani 1 1 d . . . . .
 C1 C 0.4152(3) 0.46270(9) 0.7329(2) 0.0125(4) Uani 1 1 d . . . . .
 C2 C 0.5153(3) 0.52662(10) 0.81228(19) 0.0118(4) Uani 1 1 d . . . . .
 C3 C 0.8405(3) 0.60054(10) 0.8619(2) 0.0145(4) Uani 1 1 d . . . . .
 H3a H 1.004750 0.592840 0.902149 0.017 Uiso 1 1 calc R . . . .
 H3b H 0.773184 0.616975 0.946587 0.017 Uiso 1 1 calc R . . . .
 C4 C 0.8082(3) 0.65452(10) 0.7389(2) 0.0137(4) Uani 1 1 d . . . . .
 C5 C 0.6196(3) 0.69820(10) 0.7128(2) 0.0158(4) Uani 1 1 d . . . . .
 H5 H 0.508175 0.693300 0.772254 0.019 Uiso 1 1 calc R . . . .
 C6 C 0.5929(3) 0.74878(11) 0.6008(2) 0.0201(4) Uani 1 1 d . . . . .
 H6 H 0.464298 0.778422 0.584065 0.024 Uiso 1 1 calc R . . . .
 C7 C 0.7553(3) 0.75572(11) 0.5134(2) 0.0213(4) Uani 1 1 d . . . . .
 H7 H 0.737578 0.790135 0.436453 0.026 Uiso 1 1 calc R . . . .
 C8 C 0.9435(3) 0.71254(11) 0.5380(2) 0.0211(4) Uani 1 1 d . . . . .
 H8 H 1.054448 0.717587 0.478247 0.025 Uiso 1 1 calc R . . . .
 C9 C 0.9699(3) 0.66200(11) 0.6498(2) 0.0175(4) Uani 1 1 d . . . . .
 H9 H 1.098433 0.632376 0.665876 0.021 Uiso 1 1 calc R . . . .
 C10 C 0.2023(3) 0.44507(11) 0.7297(2) 0.0192(4) Uani 1 1 d . . . . .
 H10a H 0.138654 0.405440 0.674272 0.023 Uiso 1 1 calc R . . . .
 H10b H 0.113076 0.472045 0.782921 0.023 Uiso 1 1 calc R . . . .
 C11 C 0.6852(3) 0.36721(10) 0.7269(2) 0.0119(4) Uani 1 1 d . . . . .
 C12 C 0.7865(3) 0.31235(10) 0.9768(2) 0.0156(4) Uani 1 1 d . . . . .
 C13 C 0.7404(4) 0.33458(11) 1.1287(2) 0.0218(5) Uani 1 1 d . . . . .
 H13a H 0.803274 0.380838 1.154171 0.033 Uiso 1 1 calc GR . . . .
 H13b H 0.811868 0.301848 1.207654 0.033 Uiso 1 1 calc GR . . . .
 H13c H 0.576119 0.335441 1.122529 0.033 Uiso 1 1 calc GR . . . .
 C14 C 1.0404(3) 0.31180(13) 0.9810(3) 0.0256(5) Uani 1 1 d . . . . .
 H14a H 1.066786 0.292944 0.885312 0.038 Uiso 1 1 calc GR . . . .
 H14b H 1.118219 0.283031 1.065981 0.038 Uiso 1 1 calc GR . . . .
 H14c H 1.099505 0.359076 0.994569 0.038 Uiso 1 1 calc GR . . . .
 C15 C 0.6730(4) 0.24388(11) 0.9257(2) 0.0231(5) Uani 1 1 d . . . . .
 H15a H 0.509468 0.247601 0.920805 0.035 Uiso 1 1 calc GR . . . .
 H15b H 0.737526 0.207719 0.998453 0.035 Uiso 1 1 calc GR . . . .
 H15c H 0.698582 0.232084 0.824884 0.035 Uiso 1 1 calc GR . . . .
 C16 C 0.5754(3) 0.44438(10) 0.5072(2) 0.0142(4) Uani 1 1 d . . . . .
 C17 C 0.4064(3) 0.53124(11) 0.3183(2) 0.0160(4) Uani 1 1 d . . . . .
 C18 C 0.2545(4) 0.59217(11) 0.3344(2) 0.0215(4) Uani 1 1 d . . . . .
 H18a H 0.124338 0.576015 0.373841 0.032 Uiso 1 1 calc GR . . . .
 H18b H 0.200395 0.613841 0.234791 0.032 Uiso 1 1 calc GR . . . .
 H18c H 0.340901 0.625976 0.404993 0.032 Uiso 1 1 calc GR . . . .
 C19 C 0.6263(4) 0.55569(12) 0.2803(2) 0.0249(5) Uani 1 1 d . . . . .
 H19a H 0.708224 0.585097 0.362751 0.037 Uiso 1 1 calc GR . . . .
 H19b H 0.592687 0.582140 0.185293 0.037 Uiso 1 1 calc GR . . . .
 H19c H 0.720419 0.515641 0.268400 0.037 Uiso 1 1 calc GR . . . .
 C20 C 0.2811(4) 0.47832(12) 0.2058(2) 0.0251(5) Uani 1 1 d . . . . .
 H20a H 0.379306 0.438174 0.203337 0.038 Uiso 1 1 calc GR . . . .
 H20b H 0.240635 0.499038 0.104243 0.038 Uiso 1 1 calc GR . . . .
 H20c H 0.142743 0.463645 0.237445 0.038 Uiso 1 1 calc GR . . . .


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 C2 1.342(2) . ?
 O1 C3 1.468(2) . ?
 O2 C2 1.210(2) . ?
 O3 C11 1.333(2) . ?
 O3 C12 1.489(2) . ?
 O4 C11 1.201(2) . ?
 O5 C16 1.337(2) . ?
 O5 C17 1.482(2) . ?
 O6 C16 1.195(2) . ?
 N1 C1 1.446(2) . ?
 N1 C11 1.409(2) . ?
 N1 C16 1.410(2) . ?
 C1 C2 1.490(3) . ?
 C1 C10 1.322(3) . ?
 C3 C4 1.504(3) . ?
 C4 C5 1.396(3) . ?
 C4 C9 1.397(3) . ?
 C5 C6 1.390(3) . ?
 C6 C7 1.389(3) . ?
 C7 C8 1.388(3) . ?
 C8 C9 1.388(3) . ?
 C12 C13 1.516(3) . ?
 C12 C14 1.523(3) . ?
 C12 C15 1.517(3) . ?
 C17 C18 1.519(3) . ?
 C17 C19 1.515(3) . ?
 C17 C20 1.521(3) . ?

loop_
  _geom_angle_atom_site_label_1
  _geom_angle_atom_site_label_2
  _geom_angle_atom_site_label_3
  _geom_angle
  _geom_angle_site_symmetry_1
  _geom_angle_site_symmetry_3
  _geom_angle_publ_flag
 C2 O1 C3 116.49(14) . . ?
 C11 O3 C12 119.80(14) . . ?
 C16 O5 C17 120.74(15) . . ?
 C11 N1 C1 119.95(15) . . ?
 C11 N1 C16 120.99(15) . . ?
 C16 N1 C1 118.68(15) . . ?
 N1 C1 C2 117.90(16) . . ?
 C10 C1 N1 121.00(17) . . ?
 C10 C1 C2 121.03(17) . . ?
 O1 C2 C1 111.87(15) . . ?
 O2 C2 O1 124.55(18) . . ?
 O2 C2 C1 123.58(17) . . ?
 O1 C3 C4 110.55(15) . . ?
 C5 C4 C3 121.07(17) . . ?
 C5 C4 C9 118.99(18) . . ?
 C9 C4 C3 119.93(17) . . ?
 C6 C5 C4 120.78(18) . . ?
 C7 C6 C5 119.58(19) . . ?
 C8 C7 C6 120.20(19) . . ?
 C9 C8 C7 120.16(18) . . ?
 C8 C9 C4 120.28(18) . . ?
 O3 C11 N1 108.41(15) . . ?
 O4 C11 O3 127.04(17) . . ?
 O4 C11 N1 124.54(17) . . ?
 O3 C12 C13 102.27(15) . . ?
 O3 C12 C14 110.08(16) . . ?
 O3 C12 C15 108.94(15) . . ?
 C13 C12 C14 110.98(17) . . ?
 C13 C12 C15 111.28(17) . . ?
 C15 C12 C14 112.77(18) . . ?
 O5 C16 N1 107.36(15) . . ?
 O6 C16 O5 127.52(18) . . ?
 O6 C16 N1 125.12(18) . . ?
 O5 C17 C18 101.47(15) . . ?
 O5 C17 C19 110.69(16) . . ?
 O5 C17 C20 108.83(16) . . ?
 C18 C17 C20 111.31(17) . . ?
 C19 C17 C18 110.74(17) . . ?
 C19 C17 C20 113.17(17) . . ?