 
data_ghn424_0m_a
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H17 O2' 
_chemical_formula_weight          217.27

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'
 '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            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_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+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    7.6989(2)
_cell_length_b                    14.1778(3)
_cell_length_c                    12.0083(3)
_cell_angle_alpha                 90
_cell_angle_beta                  105.433(2)
_cell_angle_gamma                 90
_cell_volume                      1263.48(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used     4093
_cell_measurement_theta_min       2.8389
_cell_measurement_theta_max       28.2761
 
_exptl_crystal_description        lump
_exptl_crystal_colour             colorless
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.142          
_exptl_crystal_F_000              468
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.2
_exptl_crystal_size_mid           0.2
_exptl_crystal_size_min           0.1
_exptl_absorpt_coefficient_mu     0.075
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    Multi-Scan
_exptl_absorpt_correction_T_min   0.6954
_exptl_absorpt_correction_T_max   0.7457
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_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             11168
_diffrn_reflns_av_unetI/netI      0.0625
_diffrn_reflns_av_R_equivalents   0.0577
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        12
_diffrn_reflns_theta_min          2.271
_diffrn_reflns_theta_max          28.282
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.987
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.987
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.987
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              3092
_reflns_number_gt                 1957
_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        ?
_computing_cell_refinement        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_data_reduction         'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_structure_solution     'XT, VERSION 2014/4'
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_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)+(0.0362P)²+3.2656P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3092
_refine_ls_number_parameters      166
_refine_ls_number_restraints      6
_refine_ls_R_factor_all           0.1600
_refine_ls_R_factor_gt            0.1031
_refine_ls_wR_factor_ref          0.2306
_refine_ls_wR_factor_gt           0.2106
_refine_ls_goodness_of_fit_ref    1.126
_refine_ls_restrained_S_all       1.127
_refine_ls_shift/su_max           0.053
_refine_ls_shift/su_mean          0.004
 
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 1.0470(3) 0.4764(2) 0.1398(2) 0.0399(7) Uani 1 1 d . . . . .
O2 O 0.7769(3) 0.4841(2) 0.0120(2) 0.0402(7) Uani 1 1 d . . . . .
H2 H 0.8473 0.5049 -0.0477 0.049 Uiso 1 1 d . . . . .
C1 C 0.8805(4) 0.4748(3) 0.1173(3) 0.0333(8) Uani 1 1 d . . . . .
C2 C 0.7877(4) 0.4657(2) 0.2089(3) 0.0269(7) Uani 1 1 d . . . . .
C3 C 0.6097(4) 0.4688(3) 0.1931(3) 0.0297(8) Uani 1 1 d . . . . .
H3 H 0.5255 0.4729 0.1193 0.036 Uiso 1 1 calc R U . . .
C4 C 0.8887(5) 0.4574(3) 0.3339(3) 0.0356(9) Uani 1 1 d . . . . .
H4A H 0.9552 0.5162 0.3622 0.043 Uiso 1 1 calc R U . . .
H4B H 0.9749 0.4041 0.3465 0.043 Uiso 1 1 calc R U . . .
C5 C 0.7375(5) 0.4395(3) 0.3948(3) 0.0351(9) Uani 1 1 d . . . . .
H5 H 0.7558 0.4792 0.4658 0.042 Uiso 1 1 calc R U . . .
C6 C 0.5570(4) 0.4649(3) 0.3051(3) 0.0290(8) Uani 1 1 d . . . . .
C7 C 0.4720(5) 0.5597(3) 0.3280(4) 0.0496(12) Uani 1 1 d . . . . .
H7A H 0.3536 0.5682 0.2558 0.055 Uiso 1 1 d . . . . .
H7B H 0.4373 0.5463 0.4130 0.074 Uiso 1 1 d . . . . .
C9 C 0.4290(5) 0.3809(3) 0.3065(3) 0.0371(9) Uani 1 1 d . . . . .
H9A H 0.3352 0.3987 0.3452 0.044 Uiso 1 1 calc R U . . .
H9B H 0.3697 0.3596 0.2270 0.044 Uiso 1 1 calc R U . . .
C10 C 0.7126(5) 0.3368(3) 0.4217(3) 0.0416(10) Uani 1 1 d . . . . .
C11 C 0.5478(6) 0.3059(3) 0.3723(4) 0.0446(10) Uani 1 1 d . . . . .
C12 C 0.8654(7) 0.2827(4) 0.5004(4) 0.0691(16) Uani 1 1 d . . . . .
H12A H 0.9690 0.2822 0.4675 0.104 Uiso 1 1 calc R U . . .
H12B H 0.8269 0.2178 0.5085 0.104 Uiso 1 1 calc R U . . .
H12C H 0.8997 0.3130 0.5765 0.104 Uiso 1 1 calc R U . . .
C13 C 0.4728(8) 0.2092(4) 0.3798(6) 0.0773(18) Uani 1 1 d . . . . .
H13A H 0.3606 0.2142 0.4032 0.116 Uiso 1 1 calc R U . . .
H13B H 0.5604 0.1717 0.4368 0.116 Uiso 1 1 calc R U . . .
H13C H 0.4485 0.1784 0.3041 0.116 Uiso 1 1 calc R U . . .
C8 C 0.5845(14) 0.6496(9) 0.3050(17) 0.050(3) Uani 0.58(2) 1 d . U P A 1
C14 C 0.5726(19) 0.7114(8) 0.2895(17) 0.086(6) Uani 0.58(2) 1 d . . P A 1
H14A H 0.4600 0.7416 0.2822 0.103 Uiso 0.58(2) 1 calc R U P A 1
H14B H 0.6726 0.7468 0.2802 0.103 Uiso 0.58(2) 1 calc R U P A 1
C14" C 0.647(2) 0.7101(13) 0.3768(16) 0.074(5) Uani 0.42(2) 1 d . . P A 2
H14C H 0.5561 0.7571 0.3658 0.089 Uiso 0.42(2) 1 calc R U P A 2
H14D H 0.7707 0.7278 0.4010 0.089 Uiso 0.42(2) 1 calc R U P A 2
C8" C 0.609(2) 0.6339(9) 0.3612(14) 0.034(3) Uani 0.42(2) 1 d . . 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 1.238(4) . ?
O2 C1 1.309(4) . ?
O2 H2 1.0500 . ?
C1 C2 1.468(5) . ?
C2 C3 1.333(4) . ?
C2 C4 1.500(5) . ?
C3 C6 1.506(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.551(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.515(6) . ?
C5 C6 1.557(5) . ?
C5 H5 1.0000 . ?
C6 C9 1.548(5) . ?
C6 C7 1.551(5) . ?
C7 C8" 1.469(14) . ?
C7 C8 1.606(15) . ?
C7 H7A 1.0849 . ?
C7 H7B 1.1367 . ?
C9 C11 1.486(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.324(6) . ?
C10 C12 1.508(6) . ?
C11 C13 1.500(6) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C8 C14 0.896(13) . ?
C14 H14A 0.9500 . ?
C14 H14B 0.9500 . ?
C14" C8" 1.12(2) . ?
C14" H14C 0.9500 . ?
C14" H14D 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 O2 H2 113.3 . . ?
O1 C1 O2 122.6(3) . . ?
O1 C1 C2 121.3(3) . . ?
O2 C1 C2 116.1(3) . . ?
C3 C2 C1 125.2(3) . . ?
C3 C2 C4 112.6(3) . . ?
C1 C2 C4 122.0(3) . . ?
C2 C3 C6 112.5(3) . . ?
C2 C3 H3 123.8 . . ?
C6 C3 H3 123.8 . . ?
C2 C4 C5 103.3(3) . . ?
C2 C4 H4A 111.1 . . ?
C5 C4 H4A 111.1 . . ?
C2 C4 H4B 111.1 . . ?
C5 C4 H4B 111.1 . . ?
H4A C4 H4B 109.1 . . ?
C10 C5 C4 114.3(3) . . ?
C10 C5 C6 103.3(3) . . ?
C4 C5 C6 106.3(3) . . ?
C10 C5 H5 110.9 . . ?
C4 C5 H5 110.9 . . ?
C6 C5 H5 110.9 . . ?
C3 C6 C9 111.2(3) . . ?
C3 C6 C7 110.7(3) . . ?
C9 C6 C7 111.4(3) . . ?
C3 C6 C5 102.9(3) . . ?
C9 C6 C5 105.6(3) . . ?
C7 C6 C5 114.7(3) . . ?
C8" C7 C6 111.3(6) . . ?
C6 C7 C8 112.6(5) . . ?
C8" C7 H7A 121.8 . . ?
C6 C7 H7A 105.0 . . ?
C8 C7 H7A 98.7 . . ?
C8" C7 H7B 101.5 . . ?
C6 C7 H7B 103.1 . . ?
C8 C7 H7B 123.6 . . ?
H7A C7 H7B 112.8 . . ?
C11 C9 C6 104.7(3) . . ?
C11 C9 H9A 110.8 . . ?
C6 C9 H9A 110.8 . . ?
C11 C9 H9B 110.8 . . ?
C6 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
C11 C10 C12 127.4(4) . . ?
C11 C10 C5 112.5(4) . . ?
C12 C10 C5 120.0(4) . . ?
C10 C11 C9 112.5(4) . . ?
C10 C11 C13 127.9(4) . . ?
C9 C11 C13 119.6(4) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C14 C8 C7 141.5(13) . . ?
C8 C14 H14A 120.0 . . ?
C8 C14 H14B 120.0 . . ?
H14A C14 H14B 120.0 . . ?
C8" C14" H14C 120.0 . . ?
C8" C14" H14D 120.0 . . ?
H14C C14" H14D 120.0 . . ?
C14" C8" C7 150.8(16) . . ?
 
_refine_diff_density_max    0.325
_refine_diff_density_min   -0.294
_refine_diff_density_rms    0.066



