 
data_zhouF007
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H26 N2 O2' 
_chemical_formula_weight          326.43

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   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            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_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+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    8.5202(4)
_cell_length_b                    11.2279(6)
_cell_length_c                    17.8067(8)
_cell_angle_alpha                 90
_cell_angle_beta                  102.0455(13)
_cell_angle_gamma                 90
_cell_volume                      1665.95(14)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     335
_cell_measurement_theta_min       15
_cell_measurement_theta_max       15
 
_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.301          
_exptl_crystal_F_000              704
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.500
_exptl_crystal_size_mid           0.400
_exptl_crystal_size_min           0.300
_exptl_absorpt_coefficient_mu     0.084
_shelx_estimated_absorpt_T_min    0.959
_shelx_estimated_absorpt_T_max    0.975
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6197  
_exptl_absorpt_correction_T_max   0.7456
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method        'PHI & OMEGA SCAN'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             27450
_diffrn_reflns_av_unetI/netI      0.0239
_diffrn_reflns_av_R_equivalents   0.0431
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          2.158
_diffrn_reflns_theta_max          25.248
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              3003
_reflns_number_gt                 2540
_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 D8VENTURE DIFFRACTOMETER'
_computing_cell_refinement        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction         'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_solution     ?
_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)+(0.0774P)²+0.5340P] 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          3003
_refine_ls_number_parameters      217
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0577
_refine_ls_R_factor_gt            0.0479
_refine_ls_wR_factor_ref          0.1404
_refine_ls_wR_factor_gt           0.1315
_refine_ls_goodness_of_fit_ref    1.083
_refine_ls_restrained_S_all       1.083
_refine_ls_shift/su_max           0.001
_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 0.62981(15) 0.80721(13) 0.77104(7) 0.0490(4) Uani 1 1 d . . . . .
O2 O 0.11711(15) 0.93328(12) 1.10280(7) 0.0475(4) Uani 1 1 d . . . . .
N1 N 0.46719(18) 0.66996(13) 0.86439(9) 0.0425(4) Uani 1 1 d . . . . .
H1A H 0.5271 0.6201 0.8468 0.051 Uiso 1 1 calc R U . . .
N2 N 0.06729(16) 0.66468(13) 0.99230(8) 0.0376(4) Uani 1 1 d . . . . .
C1 C 0.7258(2) 0.8857(2) 0.73651(12) 0.0570(6) Uani 1 1 d . . . . .
H1B H 0.8184 0.8438 0.7276 0.085 Uiso 1 1 calc R U . . .
H1C H 0.6641 0.9143 0.6886 0.085 Uiso 1 1 calc R U . . .
H1D H 0.7596 0.9518 0.7702 0.085 Uiso 1 1 calc R U . . .
C2 C 0.4916(2) 0.85346(16) 0.78777(9) 0.0373(4) Uani 1 1 d . . . . .
C3 C 0.4239(2) 0.96240(17) 0.76405(9) 0.0427(4) Uani 1 1 d . . . . .
H3A H 0.4715 1.0112 0.7329 0.051 Uiso 1 1 calc R U . . .
C4 C 0.2851(2) 0.99943(17) 0.78649(10) 0.0435(5) Uani 1 1 d . . . . .
H4A H 0.2400 1.0725 0.7694 0.052 Uiso 1 1 calc R U . . .
C5 C 0.2123(2) 0.93001(16) 0.83375(9) 0.0372(4) Uani 1 1 d . . . . .
H5A H 0.1192 0.9555 0.8483 0.045 Uiso 1 1 calc R U . . .
C6 C 0.28193(19) 0.82154(15) 0.85872(9) 0.0317(4) Uani 1 1 d . . . . .
C7 C 0.4187(2) 0.78291(15) 0.83477(9) 0.0337(4) Uani 1 1 d . . . . .
C8 C 0.23410(19) 0.72521(14) 0.90939(9) 0.0321(4) Uani 1 1 d . . . . .
C9 C 0.3941(2) 0.65435(15) 0.93198(10) 0.0386(4) Uani 1 1 d . . . . .
H9A H 0.3711 0.5699 0.9384 0.046 Uiso 1 1 calc R U . . .
C10 C 0.5055(2) 0.70092(18) 1.00438(11) 0.0422(4) Uani 1 1 d . . . . .
H10A H 0.5955 0.6468 1.0189 0.051 Uiso 1 1 calc R U . . .
H10B H 0.5476 0.7779 0.9936 0.051 Uiso 1 1 calc R U . . .
C11 C 0.4208(2) 0.71344(18) 1.07098(10) 0.0430(5) Uani 1 1 d . . . . .
H11A H 0.4969 0.7394 1.1164 0.052 Uiso 1 1 calc R U . . .
H11B H 0.3782 0.6368 1.0820 0.052 Uiso 1 1 calc R U . . .
C12 C 0.28486(18) 0.80317(15) 1.05163(9) 0.0325(4) Uani 1 1 d . . . . .
C13 C 0.34335(19) 0.93104(16) 1.04422(9) 0.0371(4) Uani 1 1 d . . . . .
H13A H 0.4427 0.9462 1.0809 0.045 Uiso 1 1 calc R U . . .
H13B H 0.3600 0.9462 0.9928 0.045 Uiso 1 1 calc R U . . .
C14 C 0.2078(2) 1.00691(17) 1.06145(10) 0.0436(4) Uani 1 1 d . . . . .
H14A H 0.2506 1.0754 1.0922 0.052 Uiso 1 1 calc R U . . .
H14B H 0.1400 1.0350 1.0141 0.052 Uiso 1 1 calc R U . . .
C15 C 0.1963(2) 0.82013(17) 1.11742(10) 0.0418(4) Uani 1 1 d . . . . .
H15A H 0.2755 0.8249 1.1659 0.050 Uiso 1 1 calc R U . . .
C16 C 0.0750(2) 0.7249(2) 1.12449(11) 0.0524(5) Uani 1 1 d . . . . .
H16A H 0.0082 0.7525 1.1589 0.063 Uiso 1 1 calc R U . . .
H16B H 0.1311 0.6540 1.1468 0.063 Uiso 1 1 calc R U . . .
C17 C -0.0309(2) 0.69331(18) 1.04770(12) 0.0464(5) Uani 1 1 d . . . . .
H17A H -0.0977 0.6255 1.0538 0.056 Uiso 1 1 calc R U . . .
H17B H -0.1007 0.7599 1.0290 0.056 Uiso 1 1 calc R U . . .
C18 C 0.16518(17) 0.76674(14) 0.97828(9) 0.0296(4) Uani 1 1 d . . . . .
H18A H 0.0933 0.8342 0.9617 0.036 Uiso 1 1 calc R U . . .
C19 C -0.0256(2) 0.63585(17) 0.91581(11) 0.0458(5) Uani 1 1 d . . . . .
H19A H -0.1127 0.6921 0.9001 0.055 Uiso 1 1 calc R U . . .
H19B H -0.0697 0.5561 0.9146 0.055 Uiso 1 1 calc R U . . .
C20 C 0.0955(2) 0.64501(18) 0.86457(11) 0.0476(5) Uani 1 1 d . . . . .
H20A H 0.0471 0.6810 0.8157 0.057 Uiso 1 1 calc R U . . .
H20B H 0.1358 0.5668 0.8552 0.057 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 C2 1.376(2) . ?
O1 C1 1.426(2) . ?
O2 C14 1.435(2) . ?
O2 C15 1.436(2) . ?
N1 C7 1.402(2) . ?
N1 C9 1.476(2) . ?
N2 C17 1.456(2) . ?
N2 C19 1.462(2) . ?
N2 C18 1.469(2) . ?
C2 C3 1.380(3) . ?
C2 C7 1.389(2) . ?
C3 C4 1.389(3) . ?
C4 C5 1.385(2) . ?
C5 C6 1.387(2) . ?
C6 C7 1.391(2) . ?
C6 C8 1.518(2) . ?
C8 C18 1.539(2) . ?
C8 C9 1.557(2) . ?
C8 C20 1.565(2) . ?
C9 C10 1.525(3) . ?
C10 C11 1.518(2) . ?
C11 C12 1.519(2) . ?
C12 C15 1.532(2) . ?
C12 C13 1.534(2) . ?
C12 C18 1.535(2) . ?
C13 C14 1.517(3) . ?
C15 C16 1.511(3) . ?
C16 C17 1.515(3) . ?
C19 C20 1.517(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 C1 117.01(16) . . ?
C14 O2 C15 108.65(13) . . ?
C7 N1 C9 105.83(13) . . ?
C17 N2 C19 113.84(14) . . ?
C17 N2 C18 111.70(14) . . ?
C19 N2 C18 103.33(13) . . ?
O1 C2 C3 126.15(16) . . ?
O1 C2 C7 115.19(16) . . ?
C3 C2 C7 118.63(16) . . ?
C2 C3 C4 120.23(16) . . ?
C5 C4 C3 121.51(17) . . ?
C4 C5 C6 118.23(16) . . ?
C5 C6 C7 120.36(15) . . ?
C5 C6 C8 131.79(15) . . ?
C7 C6 C8 107.82(14) . . ?
C2 C7 C6 121.00(16) . . ?
C2 C7 N1 127.49(16) . . ?
C6 C7 N1 111.51(15) . . ?
C6 C8 C18 116.91(13) . . ?
C6 C8 C9 100.86(13) . . ?
C18 C8 C9 114.09(13) . . ?
C6 C8 C20 111.99(14) . . ?
C18 C8 C20 102.01(13) . . ?
C9 C8 C20 111.38(14) . . ?
N1 C9 C10 110.76(14) . . ?
N1 C9 C8 102.96(13) . . ?
C10 C9 C8 113.59(14) . . ?
C11 C10 C9 112.23(14) . . ?
C10 C11 C12 110.40(14) . . ?
C11 C12 C15 112.51(13) . . ?
C11 C12 C13 113.21(14) . . ?
C15 C12 C13 99.79(14) . . ?
C11 C12 C18 110.84(14) . . ?
C15 C12 C18 109.76(13) . . ?
C13 C12 C18 110.25(13) . . ?
C14 C13 C12 103.50(13) . . ?
O2 C14 C13 107.11(15) . . ?
O2 C15 C16 109.73(15) . . ?
O2 C15 C12 105.01(13) . . ?
C16 C15 C12 115.49(16) . . ?
C15 C16 C17 112.30(15) . . ?
N2 C17 C16 110.17(14) . . ?
N2 C18 C12 111.29(13) . . ?
N2 C18 C8 102.93(13) . . ?
C12 C18 C8 117.57(12) . . ?
N2 C19 C20 103.97(14) . . ?
C19 C20 C8 105.54(14) . . ?
 
_refine_diff_density_max    0.502
_refine_diff_density_min   -0.453
_refine_diff_density_rms    0.058

_shelxl_version_number 2014/6



