data_1ac
_audit_creation_date               2022-11-26
_audit_creation_method
;
Olex2 1.5-ac5-020
(compiled 2021.11.16 svn.r5db059d7 for Rigaku Oxford Diffraction, GUI svn.r6430)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_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.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C18 H18 O'
_chemical_formula_sum              'C18 H18 O'
_chemical_formula_weight           250.32
_chemical_melting_point            ?
_chemical_oxdiff_formula           C18H18O
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'
 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             14
_space_group_name_H-M_alt          'P 1 21/c 1'
_space_group_name_Hall             '-P 2ybc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'

_cell_length_a                     8.6010(2)
_cell_length_b                     20.0405(4)
_cell_length_c                     7.9500(2)
_cell_angle_alpha                  90
_cell_angle_beta                   101.172(2)
_cell_angle_gamma                  90
_cell_volume                       1344.36(5)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      7002
_cell_measurement_temperature      302.89(10)
_cell_measurement_theta_max        79.7050
_cell_measurement_theta_min        4.4040
_shelx_estimated_absorpt_T_max     0.919
_shelx_estimated_absorpt_T_min     0.894
_exptl_absorpt_coefficient_mu      0.575
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.70841
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.72a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'clear light colourless'
_exptl_crystal_colour_lustre       clear
_exptl_crystal_colour_modifier     light
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.237
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         prism
_exptl_crystal_F_000               536
_exptl_crystal_size_max            0.2
_exptl_crystal_size_mid            0.15
_exptl_crystal_size_min            0.15
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0297
_diffrn_reflns_av_unetI/netI       0.0218
_diffrn_reflns_Laue_measured_fraction_full  1.000
_diffrn_reflns_Laue_measured_fraction_max  0.983
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         25
_diffrn_reflns_limit_k_min         -22
_diffrn_reflns_limit_l_max         10
_diffrn_reflns_limit_l_min         -9
_diffrn_reflns_number              13669
_diffrn_reflns_point_group_measured_fraction_full  1.000
_diffrn_reflns_point_group_measured_fraction_max  0.983
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           79.709
_diffrn_reflns_theta_min           4.412
_diffrn_ambient_environment        air
_diffrn_ambient_temperature        302.89(10)
_diffrn_detector                   'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean   10.0000
_diffrn_detector_type              HyPix
_diffrn_measured_fraction_theta_full  1.000
_diffrn_measured_fraction_theta_max  0.983
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -72.00 -33.00   0.50    0.10    -- -104.00  77.00 120.00   78
  2  ω    -51.00 -22.00   0.50    0.10    -- -104.00  63.00  90.00   58
  3  ω    -52.00 -21.00   0.50    0.10    -- -104.00  63.00 -30.00   62
  4  ω      8.00  33.00   0.50    0.05    --  -15.46  29.00  22.00   50
  5  ω     -2.00  26.00   0.50    0.05    --   15.46  29.00  22.00   56
  6  ω    -22.00  15.00   0.50    0.05    --   15.46  77.00 120.00   74
  7  ω    -26.00  11.00   0.50    0.05    --   15.46  77.00  30.00   74
  8  ω    -17.00  59.00   0.50    0.05    --   15.46  57.00-120.00  152
  9  ω     -9.00  18.00   0.50    0.05    --   15.46  77.00 -60.00   54
 10  ω     31.00  98.00   0.50    0.05    --   15.46  29.00  22.00  134
 11  ω    108.00 149.00   0.50    0.10    --   71.98  77.00 -90.00   82
 12  ω    108.00 141.00   0.50    0.10    --   71.98  77.00-120.00   66
 13  ω    110.00 159.00   0.50    0.10    --  128.50  77.00-150.00   98
 14  ω    151.00 176.00   0.50    0.10    --  128.50  77.00 -90.00   50
 15  ω    145.00 177.00   0.50    0.10    --  128.50  77.00 -30.00   64
 16  ω    108.00 139.00   0.50    0.10    --  128.50  77.00 -30.00   62
 17  ω    115.00 140.00   0.50    0.10    --  128.50  77.00  60.00   50
 18  ω     99.00 131.00   0.50    0.10    --  128.50  63.00  90.00   64
 19  ω    137.00 167.00   0.50    0.10    --  128.50  63.00  90.00   60
 20  ω    100.00 170.00   0.50    0.10    --  128.50  63.00 120.00  140
 21  ω     32.00  57.00   0.50    0.10    --   71.98  56.00 139.65   50
 22  ω     31.00  57.00   0.50    0.10    --   71.98  54.00 169.81   52
 23  ω     33.00  58.00   0.50    0.10    --   71.98  57.00 115.55   50
 24  ω     97.00 159.00   0.50    0.10    --  128.50  63.00  60.00  124
 25  ω    100.00 158.00   0.50    0.10    --  128.50  63.00 -90.00  116
 26  ω     88.00 132.00   0.50    0.10    --  128.50  50.00-150.00   88
 27  ω     89.00 178.00   0.50    0.10    --  128.50  50.00-180.00  178
 28  ω     87.00 141.00   0.50    0.10    --   71.98  51.00-152.56  108
 29  ω     31.00  74.00   0.50    0.10    --   71.98  51.00-152.56   86
 30  ω     89.00 114.00   0.50    0.10    --  128.50  50.00  90.00   50
 31  ω     93.00 122.00   0.50    0.10    --  128.50  50.00 120.00   58
 32  ω    123.00 149.00   0.50    0.10    --  128.50  38.00 150.00   52
 33  ω     92.00 142.00   0.50    0.10    --  128.50  50.00 150.00  100
 34  ω     90.00 115.00   0.50    0.10    --  128.50  38.00 150.00   50
 35  ω     86.00 120.00   0.50    0.10    --  128.50  38.00 120.00   68
 36  ω     84.00 115.00   0.50    0.10    --  128.50  38.00  90.00   62
 37  ω     63.00  97.00   0.50    0.10    --   71.98  45.00 120.00   68
 38  ω     25.00 153.00   0.50    0.10    --   71.98  29.00  22.00  256
 39  ω    151.00 176.00   0.50    0.10    --  128.50  38.00  90.00   50
 40  ω    121.00 148.00   0.50    0.10    --  128.50  29.00  22.00   54
 41  ω    151.00 176.00   0.50    0.10    --  128.50  38.00-150.00   50
 42  ω     84.00 121.00   0.50    0.10    --  128.50  38.00-150.00   74
 43  ω    100.00 143.00   0.50    0.10    --   71.98 125.00-120.00   86
 44  ω     52.00  77.00   0.50    0.10    --  128.50 -77.00  30.00   50
 45  ω     39.00  65.00   0.50    0.10    --  128.50 -77.00   0.00   52
 46  ω     42.00  75.00   0.50    0.10    --  128.50 -77.00 -90.00   66
 47  ω     37.00  62.00   0.50    0.10    --  128.50 -77.00-120.00   50
 48  ω    -17.00   8.00   0.50    0.10    --   71.98 -30.00 -90.00   50
 49  ω    -18.00   8.00   0.50    0.10    --   71.98 -30.00-120.00   52
 50  ω    -65.00 -30.00   0.50    0.05    --   15.46 -29.00-137.00   70
 51  ω     57.00  92.00   0.50    0.10    --  128.50-111.00 120.00   70
 52  ω     49.00  85.00   0.50    0.10    --  128.50-111.00  90.00   72
 53  ω     43.00  93.00   0.50    0.10    --  128.50-111.00   0.00  100
 54  ω     56.00  88.00   0.50    0.10    --  128.50 -91.00   0.00   64
 55  ω     56.00  83.00   0.50    0.10    --  128.50 -91.00  90.00   54
 56  ω     39.00  92.00   0.50    0.10    --  128.50 -91.00 120.00  106
 57  ω     50.00  90.00   0.50    0.10    --  128.50-111.00 -90.00   80
 58  ω     52.00  81.00   0.50    0.10    --  128.50-111.00-180.00   58
 59  ω      2.00  65.00   0.50    0.05    --   15.46 -99.00-120.00  126
 60  ω   -104.00 -58.00   0.50    0.10    -- -104.00 -29.00-137.00   92
 61  ω   -174.00-118.00   0.50    0.10    -- -104.00 -50.00  90.00  112
 62  ω   -109.00 -64.00   0.50    0.10    -- -104.00 -50.00 120.00   90
 63  ω    -89.00 -63.00   0.50    0.10    -- -104.00 -50.00 150.00   52
 64  ω    -88.00 -62.00   0.50    0.10    -- -104.00 -50.00  90.00   52
 65  ω    -93.00 -62.00   0.50    0.10    -- -104.00 -50.00  60.00   62
 66  ω    -95.00 -62.00   0.50    0.10    -- -104.00 -50.00  30.00   66
 67  ω    -65.00 -31.00   0.50    0.10    --  -71.98 -49.00  51.97   68
 68  ω   -175.00-104.00   0.50    0.10    -- -104.00 -50.00  30.00  142
 69  ω   -161.00-135.00   0.50    0.10    -- -104.00 -50.00  60.00   52
 70  ω    -98.00 -72.00   0.50    0.10    -- -104.00 -38.00 120.00   52
 71  ω    -51.00 -26.00   0.50    0.05    --  -15.46 -29.00-137.00   50
 72  ω   -104.00 -33.00   0.50    0.10    --  -71.98 -29.00-137.00  142
 73  ω    -98.00 -62.00   0.50    0.10    --  -71.98 -45.00-180.00   72
 74  ω   -148.00 -89.00   0.50    0.10    --  -71.98 -61.00-180.00  118
 75  ω   -139.00 -95.00   0.50    0.10    --  -71.98-125.00  30.00   88
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        0.1580857000
_diffrn_orient_matrix_UB_12        -0.0156542000
_diffrn_orient_matrix_UB_13        0.1216350000
_diffrn_orient_matrix_UB_21        0.0913434000
_diffrn_orient_matrix_UB_22        0.0247293000
_diffrn_orient_matrix_UB_23        -0.1367188000
_diffrn_orient_matrix_UB_31        0.0029607000
_diffrn_orient_matrix_UB_32        0.0710851000
_diffrn_orient_matrix_UB_33        0.0741873000
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             'Cu K\a'
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'Rotating-anode X-ray tube'
_diffrn_source_type                'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2495
_reflns_number_total               2875
_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         'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_collection         'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_data_reduction          'CrysAlisPro 1.171.42.72a (Rigaku OD, 2022)'
_computing_molecular_graphics      'Olex2 1.5-ac5-020 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 1.5-ac5-020 (Dolomanov et al., 2009)'
_computing_structure_refinement    'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution      'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max           0.261
_refine_diff_density_min           -0.231
_refine_diff_density_rms           0.038
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     1.102
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       172
_refine_ls_number_reflns           2875
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0467
_refine_ls_R_factor_gt             0.0420
_refine_ls_restrained_S_all        1.102
_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)+(0.0642P)²+0.1560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1198
_refine_ls_wR_factor_ref           0.1236
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens     geom
_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 0.21435(12) 0.45062(5) 0.28238(12) 0.0639(3) Uani 1 1 d . . . . .
 C1 C 0.20811(18) 0.47186(7) 0.45465(18) 0.0589(3) Uani 1 1 d . . . . .
 H1A H 0.110654 0.456345 0.485785 0.071 Uiso 1 1 calc R U . . .
 H1B H 0.210021 0.520202 0.460969 0.071 Uiso 1 1 calc R U . . .
 C2 C 0.34683(15) 0.44387(6) 0.57507(16) 0.0483(3) Uani 1 1 d . . . . .
 H2 H 0.443529 0.465351 0.580579 0.058 Uiso 1 1 calc R U . . .
 C3 C 0.34521(13) 0.39061(6) 0.67618(14) 0.0420(3) Uani 1 1 d . . . . .
 C4 C 0.49048(14) 0.34691(6) 0.71105(15) 0.0475(3) Uani 1 1 d . . . . .
 H4A H 0.487799 0.318797 0.809763 0.057 Uiso 1 1 calc R U . . .
 H4B H 0.584808 0.374486 0.736460 0.057 Uiso 1 1 calc R U . . .
 C5 C 0.49612(16) 0.30271(6) 0.55177(16) 0.0504(3) Uani 1 1 d . . . . .
 H5A H 0.571588 0.266903 0.585563 0.061 Uiso 1 1 calc R U . . .
 H5B H 0.392738 0.282592 0.513524 0.061 Uiso 1 1 calc R U . . .
 C6 C 0.54183(14) 0.34010(6) 0.40266(15) 0.0463(3) Uani 1 1 d . . . . .
 C7 C 0.43613(15) 0.37534(6) 0.27670(15) 0.0464(3) Uani 1 1 d . . . . .
 C8 C 0.25915(16) 0.38223(7) 0.26744(17) 0.0539(3) Uani 1 1 d . . . . .
 H8A H 0.203117 0.364358 0.159150 0.065 Uiso 1 1 calc R U . . .
 H8B H 0.228528 0.356419 0.358985 0.065 Uiso 1 1 calc R U . . .
 C9 C 0.70299(16) 0.34157(8) 0.39435(18) 0.0588(3) Uani 1 1 d . . . . .
 H9 H 0.774786 0.318667 0.476819 0.071 Uiso 1 1 calc R U . . .
 C10 C 0.75877(18) 0.37607(8) 0.2671(2) 0.0673(4) Uani 1 1 d . . . . .
 H10 H 0.866556 0.376404 0.265234 0.081 Uiso 1 1 calc R U . . .
 C11 C 0.65413(19) 0.40980(8) 0.14357(19) 0.0650(4) Uani 1 1 d . . . . .
 H11 H 0.690435 0.432970 0.057429 0.078 Uiso 1 1 calc R U . . .
 C12 C 0.49524(18) 0.40896(7) 0.14857(17) 0.0572(3) Uani 1 1 d . . . . .
 H12 H 0.424899 0.431494 0.063940 0.069 Uiso 1 1 calc R U . . .
 C13 C 0.20052(13) 0.36842(6) 0.73663(14) 0.0428(3) Uani 1 1 d . . . . .
 C14 C 0.09986(15) 0.41549(7) 0.78916(16) 0.0508(3) Uani 1 1 d . . . . .
 H14 H 0.122652 0.460662 0.782298 0.061 Uiso 1 1 calc R U . . .
 C15 C -0.03312(16) 0.39627(8) 0.85121(18) 0.0591(3) Uani 1 1 d . . . . .
 H15 H -0.099235 0.428445 0.884072 0.071 Uiso 1 1 calc R U . . .
 C16 C -0.06750(16) 0.32974(8) 0.86429(19) 0.0619(4) Uani 1 1 d . . . . .
 H16 H -0.156386 0.316731 0.906558 0.074 Uiso 1 1 calc R U . . .
 C17 C 0.03064(17) 0.28241(8) 0.8143(2) 0.0636(4) Uani 1 1 d . . . . .
 H17 H 0.007497 0.237356 0.822963 0.076 Uiso 1 1 calc R U . . .
 C18 C 0.16362(15) 0.30133(7) 0.75132(18) 0.0531(3) Uani 1 1 d . . . . .
 H18 H 0.228868 0.268790 0.718516 0.064 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 1.4452(17) . ?
 O1 C8 1.4347(16) . ?
 C1 C2 1.4873(19) . ?
 C2 C3 1.3379(16) . ?
 C3 C4 1.5068(16) . ?
 C3 C13 1.4863(15) . ?
 C4 C5 1.5538(17) . ?
 C5 C6 1.5172(17) . ?
 C6 C7 1.4055(17) . ?
 C6 C9 1.4007(18) . ?
 C7 C8 1.5160(18) . ?
 C7 C12 1.3968(18) . ?
 C9 C10 1.386(2) . ?
 C10 C11 1.374(2) . ?
 C11 C12 1.375(2) . ?
 C13 C14 1.3978(17) . ?
 C13 C18 1.3916(17) . ?
 C14 C15 1.3852(18) . ?
 C15 C16 1.374(2) . ?
 C16 C17 1.378(2) . ?
 C17 C18 1.3874(18) . ?

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
 C8 O1 C1 114.82(10) . . ?
 O1 C1 C2 109.05(10) . . ?
 C3 C2 C1 125.96(12) . . ?
 C2 C3 C4 117.99(11) . . ?
 C2 C3 C13 122.67(11) . . ?
 C13 C3 C4 118.89(10) . . ?
 C3 C4 C5 109.70(9) . . ?
 C6 C5 C4 114.14(10) . . ?
 C7 C6 C5 125.10(11) . . ?
 C9 C6 C5 117.12(11) . . ?
 C9 C6 C7 117.73(12) . . ?
 C6 C7 C8 125.82(11) . . ?
 C12 C7 C6 119.04(12) . . ?
 C12 C7 C8 115.13(12) . . ?
 O1 C8 C7 111.48(11) . . ?
 C10 C9 C6 122.05(14) . . ?
 C11 C10 C9 119.71(14) . . ?
 C10 C11 C12 119.36(14) . . ?
 C11 C12 C7 122.09(13) . . ?
 C14 C13 C3 120.04(11) . . ?
 C18 C13 C3 122.34(11) . . ?
 C18 C13 C14 117.54(11) . . ?
 C15 C14 C13 121.38(13) . . ?
 C16 C15 C14 120.10(13) . . ?
 C15 C16 C17 119.55(13) . . ?
 C16 C17 C18 120.65(13) . . ?
 C17 C18 C13 120.78(13) . . ?

_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  1.568
_oxdiff_exptl_absorpt_empirical_full_min  0.637
