 
data_cu_gg1902b_a 
  
_audit_creation_method            SHELXL-2014/6 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C21 H28 O' 
_chemical_formula_sum 
 'C21 H28 O' 
_chemical_formula_weight          296.43 
  
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' 
  
_space_group_crystal_system       triclinic 
_space_group_IT_number            2 
_space_group_name_H-M_alt         'P -1' 
_space_group_name_Hall            '-P 1' 
  
_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. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x, -y, -z' 
  
_cell_length_a                    6.8189(2) 
_cell_length_b                    11.2964(2) 
_cell_length_c                    11.9414(2) 
_cell_angle_alpha                 112.7040(10) 
_cell_angle_beta                  97.5670(10) 
_cell_angle_gamma                 90.1370(10) 
_cell_volume                      839.74(3) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     6187 
_cell_measurement_theta_min       4.06 
_cell_measurement_theta_max       69.20 
  
_exptl_crystal_description        block 
_exptl_crystal_colour             colorless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.172 
_exptl_crystal_F_000              324 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.200 
_exptl_crystal_size_mid           0.180 
_exptl_crystal_size_min           0.160 
_exptl_absorpt_coefficient_mu     0.526 
_shelx_estimated_absorpt_T_min    0.902 
_shelx_estimated_absorpt_T_max    0.921 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.69 
_exptl_absorpt_correction_T_max   0.75 
_exptl_absorpt_process_details    'SADABS V2014/2 (Bruker AXS Inc.)' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    'I\mS micro--focus source' 
_diffrn_measurement_device_type   'Bruker APEX-II CCD' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  8.3333 
_diffrn_reflns_number             14514 
_diffrn_reflns_av_unetI/netI      0.0285 
_diffrn_reflns_av_R_equivalents   0.0505 
_diffrn_reflns_limit_h_min        -7 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          4.055 
_diffrn_reflns_theta_max          69.399 
_diffrn_reflns_theta_full         67.679 
_diffrn_measured_fraction_theta_max   0.955 
_diffrn_measured_fraction_theta_full  0.964 
_diffrn_reflns_Laue_measured_fraction_max    0.955 
_diffrn_reflns_Laue_measured_fraction_full   0.964 
_diffrn_reflns_point_group_measured_fraction_max   0.955 
_diffrn_reflns_point_group_measured_fraction_full  0.964 
_reflns_number_total              3021 
_reflns_number_gt                 2516 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_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. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement 'SHELXL-2014/6 (Sheldrick, 2014)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0605P)²+0.1898P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          3021 
_refine_ls_number_parameters      202 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0473 
_refine_ls_R_factor_gt            0.0410 
_refine_ls_wR_factor_ref          0.1175 
_refine_ls_wR_factor_gt           0.1149 
_refine_ls_goodness_of_fit_ref    1.132 
_refine_ls_restrained_S_all       1.132 
_refine_ls_shift/su_max           0.002 
_refine_ls_shift/su_mean          0.000 
  
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 0.79728(15) 0.37793(10) 0.78440(9) 0.0262(3) Uani 1 1 d . . . . . 
C1 C 0.68161(19) 0.23154(12) 0.51632(12) 0.0146(3) Uani 1 1 d . . . . . 
C2 C 0.8776(2) 0.16696(13) 0.52924(13) 0.0172(3) Uani 1 1 d . . . . . 
H2A H 0.9600 0.2196 0.6079 0.021 Uiso 1 1 calc R U . . . 
H2B H 0.8492 0.0812 0.5296 0.021 Uiso 1 1 calc R U . . . 
C3 C 0.9912(2) 0.15289(13) 0.42229(13) 0.0190(3) Uani 1 1 d . . . . . 
H3 H 1.1183 0.1115 0.4319 0.023 Uiso 1 1 calc R U . . . 
C4 C 0.8666(2) 0.07016(13) 0.30004(13) 0.0222(3) Uani 1 1 d . . . . . 
H4A H 0.8380 -0.0167 0.2981 0.027 Uiso 1 1 calc R U . . . 
H4B H 0.9409 0.0610 0.2316 0.027 Uiso 1 1 calc R U . . . 
C5 C 0.6721(2) 0.13376(13) 0.28522(12) 0.0185(3) Uani 1 1 d . . . . . 
H5 H 0.5895 0.0795 0.2059 0.022 Uiso 1 1 calc R U . . . 
C6 C 0.7170(2) 0.26725(13) 0.28664(13) 0.0194(3) Uani 1 1 d . . . . . 
H6A H 0.5915 0.3082 0.2762 0.023 Uiso 1 1 calc R U . . . 
H6B H 0.7898 0.2594 0.2179 0.023 Uiso 1 1 calc R U . . . 
C7 C 0.8420(2) 0.35049(12) 0.40863(12) 0.0173(3) Uani 1 1 d . . . . . 
H7 H 0.8721 0.4374 0.4091 0.021 Uiso 1 1 calc R U . . . 
C8 C 0.72763(19) 0.36465(12) 0.51532(12) 0.0162(3) Uani 1 1 d . . . . . 
H8A H 0.6024 0.4064 0.5063 0.019 Uiso 1 1 calc R U . . . 
H8B H 0.8078 0.4197 0.5940 0.019 Uiso 1 1 calc R U . . . 
C9 C 0.55934(19) 0.14803(13) 0.39217(12) 0.0168(3) Uani 1 1 d . . . . . 
H9A H 0.5283 0.0619 0.3912 0.020 Uiso 1 1 calc R U . . . 
H9B H 0.4326 0.1878 0.3821 0.020 Uiso 1 1 calc R U . . . 
C10 C 1.0364(2) 0.28682(13) 0.42410(13) 0.0187(3) Uani 1 1 d . . . . . 
H10A H 1.1178 0.3405 0.5028 0.022 Uiso 1 1 calc R U . . . 
H10B H 1.1125 0.2792 0.3568 0.022 Uiso 1 1 calc R U . . . 
C11 C 0.5583(2) 0.23864(13) 0.61690(12) 0.0184(3) Uani 1 1 d . . . . . 
H11A H 0.4319 0.2761 0.6009 0.022 Uiso 1 1 calc R U . . . 
H11B H 0.5253 0.1494 0.6067 0.022 Uiso 1 1 calc R U . . . 
C12 C 0.6428(2) 0.31266(13) 0.75022(12) 0.0179(3) Uani 1 1 d . . . . . 
C13 C 0.52089(19) 0.29727(12) 0.84125(12) 0.0159(3) Uani 1 1 d . . . . . 
C14 C 0.5754(2) 0.20652(13) 0.89184(12) 0.0178(3) Uani 1 1 d . . . . . 
C15 C 0.4643(2) 0.19269(13) 0.97615(12) 0.0201(3) Uani 1 1 d . . . . . 
H15 H 0.4998 0.1314 1.0107 0.024 Uiso 1 1 calc R U . . . 
C16 C 0.3026(2) 0.26621(14) 1.01145(13) 0.0213(3) Uani 1 1 d . . . . . 
C17 C 0.2513(2) 0.35461(13) 0.95946(13) 0.0204(3) Uani 1 1 d . . . . . 
H17 H 0.1408 0.4049 0.9826 0.024 Uiso 1 1 calc R U . . . 
C18 C 0.3580(2) 0.37156(13) 0.87404(12) 0.0175(3) Uani 1 1 d . . . . . 
C19 C 0.2983(2) 0.47184(14) 0.82355(14) 0.0223(3) Uani 1 1 d . . . . . 
H19A H 0.3971 0.4805 0.7741 0.033 Uiso 1 1 calc R U . . . 
H19B H 0.2904 0.5545 0.8915 0.033 Uiso 1 1 calc R U . . . 
H19C H 0.1687 0.4457 0.7722 0.033 Uiso 1 1 calc R U . . . 
C20 C 0.7515(2) 0.12688(14) 0.85650(13) 0.0232(3) Uani 1 1 d . . . . . 
H20A H 0.7708 0.0722 0.9034 0.035 Uiso 1 1 calc R U . . . 
H20B H 0.8702 0.1838 0.8746 0.035 Uiso 1 1 calc R U . . . 
H20C H 0.7279 0.0729 0.7686 0.035 Uiso 1 1 calc R U . . . 
C21 C 0.1886(2) 0.25354(17) 1.10677(15) 0.0328(4) Uani 1 1 d . . . . . 
H21A H 0.2454 0.1878 1.1340 0.049 Uiso 1 1 calc R U . . . 
H21B H 0.0495 0.2284 1.0712 0.049 Uiso 1 1 calc R U . . . 
H21C H 0.1970 0.3361 1.1771 0.049 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 C12 1.2129(16) . ? 
C1 C11 1.5321(17) . ? 
C1 C8 1.5402(17) . ? 
C1 C9 1.5407(18) . ? 
C1 C2 1.5427(17) . ? 
C2 C3 1.5362(18) . ? 
C2 H2A 0.9900 . ? 
C2 H2B 0.9900 . ? 
C3 C4 1.531(2) . ? 
C3 C10 1.5347(18) . ? 
C3 H3 1.0000 . ? 
C4 C5 1.5318(19) . ? 
C4 H4A 0.9900 . ? 
C4 H4B 0.9900 . ? 
C5 C6 1.5311(18) . ? 
C5 C9 1.5327(17) . ? 
C5 H5 1.0000 . ? 
C6 C7 1.5313(19) . ? 
C6 H6A 0.9900 . ? 
C6 H6B 0.9900 . ? 
C7 C10 1.5334(18) . ? 
C7 C8 1.5369(17) . ? 
C7 H7 1.0000 . ? 
C8 H8A 0.9900 . ? 
C8 H8B 0.9900 . ? 
C9 H9A 0.9900 . ? 
C9 H9B 0.9900 . ? 
C10 H10A 0.9900 . ? 
C10 H10B 0.9900 . ? 
C11 C12 1.5146(19) . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
C12 C13 1.5118(17) . ? 
C13 C18 1.3990(18) . ? 
C13 C14 1.4052(18) . ? 
C14 C15 1.3902(19) . ? 
C14 C20 1.5086(18) . ? 
C15 C16 1.393(2) . ? 
C15 H15 0.9500 . ? 
C16 C17 1.389(2) . ? 
C16 C21 1.5095(19) . ? 
C17 C18 1.3972(18) . ? 
C17 H17 0.9500 . ? 
C18 C19 1.5089(19) . ? 
C19 H19A 0.9800 . ? 
C19 H19B 0.9800 . ? 
C19 H19C 0.9800 . ? 
C20 H20A 0.9800 . ? 
C20 H20B 0.9800 . ? 
C20 H20C 0.9800 . ? 
C21 H21A 0.9800 . ? 
C21 H21B 0.9800 . ? 
C21 H21C 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 
C11 C1 C8 112.47(11) . . ? 
C11 C1 C9 107.40(10) . . ? 
C8 C1 C9 108.24(10) . . ? 
C11 C1 C2 111.32(10) . . ? 
C8 C1 C2 109.18(10) . . ? 
C9 C1 C2 108.06(10) . . ? 
C3 C2 C1 110.10(10) . . ? 
C3 C2 H2A 109.6 . . ? 
C1 C2 H2A 109.6 . . ? 
C3 C2 H2B 109.6 . . ? 
C1 C2 H2B 109.6 . . ? 
H2A C2 H2B 108.2 . . ? 
C4 C3 C10 109.45(11) . . ? 
C4 C3 C2 110.21(11) . . ? 
C10 C3 C2 108.93(11) . . ? 
C4 C3 H3 109.4 . . ? 
C10 C3 H3 109.4 . . ? 
C2 C3 H3 109.4 . . ? 
C3 C4 C5 109.39(11) . . ? 
C3 C4 H4A 109.8 . . ? 
C5 C4 H4A 109.8 . . ? 
C3 C4 H4B 109.8 . . ? 
C5 C4 H4B 109.8 . . ? 
H4A C4 H4B 108.2 . . ? 
C6 C5 C4 109.62(11) . . ? 
C6 C5 C9 108.95(11) . . ? 
C4 C5 C9 109.23(11) . . ? 
C6 C5 H5 109.7 . . ? 
C4 C5 H5 109.7 . . ? 
C9 C5 H5 109.7 . . ? 
C5 C6 C7 109.56(11) . . ? 
C5 C6 H6A 109.8 . . ? 
C7 C6 H6A 109.8 . . ? 
C5 C6 H6B 109.8 . . ? 
C7 C6 H6B 109.8 . . ? 
H6A C6 H6B 108.2 . . ? 
C6 C7 C10 109.50(11) . . ? 
C6 C7 C8 109.80(11) . . ? 
C10 C7 C8 109.24(10) . . ? 
C6 C7 H7 109.4 . . ? 
C10 C7 H7 109.4 . . ? 
C8 C7 H7 109.4 . . ? 
C7 C8 C1 109.99(10) . . ? 
C7 C8 H8A 109.7 . . ? 
C1 C8 H8A 109.7 . . ? 
C7 C8 H8B 109.7 . . ? 
C1 C8 H8B 109.7 . . ? 
H8A C8 H8B 108.2 . . ? 
C5 C9 C1 111.31(11) . . ? 
C5 C9 H9A 109.4 . . ? 
C1 C9 H9A 109.4 . . ? 
C5 C9 H9B 109.4 . . ? 
C1 C9 H9B 109.4 . . ? 
H9A C9 H9B 108.0 . . ? 
C7 C10 C3 109.68(11) . . ? 
C7 C10 H10A 109.7 . . ? 
C3 C10 H10A 109.7 . . ? 
C7 C10 H10B 109.7 . . ? 
C3 C10 H10B 109.7 . . ? 
H10A C10 H10B 108.2 . . ? 
C12 C11 C1 119.57(11) . . ? 
C12 C11 H11A 107.4 . . ? 
C1 C11 H11A 107.4 . . ? 
C12 C11 H11B 107.4 . . ? 
C1 C11 H11B 107.4 . . ? 
H11A C11 H11B 107.0 . . ? 
O1 C12 C13 121.07(12) . . ? 
O1 C12 C11 124.22(12) . . ? 
C13 C12 C11 114.69(11) . . ? 
C18 C13 C14 120.96(12) . . ? 
C18 C13 C12 120.71(12) . . ? 
C14 C13 C12 118.33(12) . . ? 
C15 C14 C13 118.48(12) . . ? 
C15 C14 C20 120.73(12) . . ? 
C13 C14 C20 120.79(12) . . ? 
C14 C15 C16 121.83(13) . . ? 
C14 C15 H15 119.1 . . ? 
C16 C15 H15 119.1 . . ? 
C17 C16 C15 118.50(13) . . ? 
C17 C16 C21 120.38(13) . . ? 
C15 C16 C21 121.10(13) . . ? 
C16 C17 C18 121.71(13) . . ? 
C16 C17 H17 119.1 . . ? 
C18 C17 H17 119.1 . . ? 
C17 C18 C13 118.52(12) . . ? 
C17 C18 C19 119.18(12) . . ? 
C13 C18 C19 122.27(12) . . ? 
C18 C19 H19A 109.5 . . ? 
C18 C19 H19B 109.5 . . ? 
H19A C19 H19B 109.5 . . ? 
C18 C19 H19C 109.5 . . ? 
H19A C19 H19C 109.5 . . ? 
H19B C19 H19C 109.5 . . ? 
C14 C20 H20A 109.5 . . ? 
C14 C20 H20B 109.5 . . ? 
H20A C20 H20B 109.5 . . ? 
C14 C20 H20C 109.5 . . ? 
H20A C20 H20C 109.5 . . ? 
H20B C20 H20C 109.5 . . ? 
C16 C21 H21A 109.5 . . ? 
C16 C21 H21B 109.5 . . ? 
H21A C21 H21B 109.5 . . ? 
C16 C21 H21C 109.5 . . ? 
H21A C21 H21C 109.5 . . ? 
H21B C21 H21C 109.5 . . ? 
  
_refine_diff_density_max    0.292 
_refine_diff_density_min   -0.260 
_refine_diff_density_rms    0.042 
  
_shelxl_version_number 2014/6 
  
  
  
