 
data_mo_19132_0m_a
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             (+)-10r
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H21 N3 O2' 
_chemical_formula_weight          335.40

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       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
 
_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, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    5.71030(10)
_cell_length_b                    14.1241(4)
_cell_length_c                    21.9310(6)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      1768.80(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     125(2)
_cell_measurement_reflns_used     9962
_cell_measurement_theta_min       2.35
_cell_measurement_theta_max       30.35
 
_exptl_crystal_description        Needles
_exptl_crystal_colour             Colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.259          
_exptl_crystal_F_000              712
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.5
_exptl_crystal_size_mid           0.3
_exptl_crystal_size_min           0.1
_exptl_absorpt_coefficient_mu     0.083
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    'none'
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       125(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  ?
_diffrn_reflns_number             34837
_diffrn_reflns_av_unetI/netI      0.0266
_diffrn_reflns_av_R_equivalents   0.0387
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -20
_diffrn_reflns_limit_k_max        20
_diffrn_reflns_limit_l_min        -31
_diffrn_reflns_limit_l_max        31
_diffrn_reflns_theta_min          2.351
_diffrn_reflns_theta_max          30.460
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.997
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.997
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              5352
_reflns_number_gt                 4878
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.741
_reflns_Friedel_fraction_max      0.996
_reflns_Friedel_fraction_full     0.999
 
_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     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.1000P)²] 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_abs_structure_details
;
 Flack x determined using 1923 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.5(3)
_chemical_absolute_configuration  (3R,4R)-3-azido-3-methyl-6-((S)-phenylethoxy)-4-vinylchromane
_refine_ls_number_reflns          5352
_refine_ls_number_parameters      228
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0436
_refine_ls_R_factor_gt            0.0377
_refine_ls_wR_factor_ref          0.1223
_refine_ls_wR_factor_gt           0.1160
_refine_ls_goodness_of_fit_ref    0.958
_refine_ls_restrained_S_all       0.958
_refine_ls_shift/su_max           0.000
_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 0.4309(2) 0.38807(8) 0.32189(5) 0.0222(2) Uani 1 1 d . . . . .
N1 N 0.9242(2) 0.60667(10) 0.53412(6) 0.0245(3) Uani 1 1 d . . . . .
C1 C 0.3501(4) 0.03396(12) 0.29365(9) 0.0338(4) Uani 1 1 d . . . . .
H1 H 0.377324 -0.031738 0.287638 0.041 Uiso 1 1 calc R U . . .
O2 O 0.9833(2) 0.40376(8) 0.52838(6) 0.0308(3) Uani 1 1 d . . . . .
N2 N 0.9718(3) 0.63831(10) 0.58481(7) 0.0261(3) Uani 1 1 d . . . . .
C2 C 0.1609(4) 0.06399(13) 0.32759(10) 0.0407(5) Uani 1 1 d . . . . .
H2 H 0.056931 0.018767 0.344768 0.049 Uiso 1 1 calc R U . . .
C3 C 0.1213(4) 0.16037(12) 0.33685(9) 0.0337(4) Uani 1 1 d . . . . .
H3 H -0.008609 0.180498 0.360600 0.040 Uiso 1 1 calc R U . . .
N3 N 0.9970(4) 0.67044(14) 0.63172(8) 0.0445(4) Uani 1 1 d . . . . .
C4 C 0.2706(3) 0.22669(10) 0.31157(7) 0.0206(3) Uani 1 1 d . . . . .
C5 C 0.4608(3) 0.19654(12) 0.27718(8) 0.0291(3) Uani 1 1 d . . . . .
H5 H 0.564279 0.241562 0.259599 0.035 Uiso 1 1 calc R U . . .
C6 C 0.4993(3) 0.09988(12) 0.26853(9) 0.0338(4) Uani 1 1 d . . . . .
H6 H 0.629705 0.079382 0.245096 0.041 Uiso 1 1 calc R U . . .
C8 C 0.0798(3) 0.37195(12) 0.26807(8) 0.0269(3) Uani 1 1 d . . . . .
H8A H -0.066934 0.336534 0.263928 0.040 Uiso 1 1 calc R U . . .
H8B H 0.169909 0.366929 0.230184 0.040 Uiso 1 1 calc R U . . .
H8C H 0.044756 0.438653 0.276327 0.040 Uiso 1 1 calc R U . . .
C7 C 0.2216(3) 0.33129(10) 0.32037(7) 0.0210(3) Uani 1 1 d . . . . .
H7 H 0.133230 0.340405 0.359292 0.025 Uiso 1 1 calc R U . . .
C9 C 0.5636(3) 0.38766(10) 0.37412(7) 0.0189(3) Uani 1 1 d . . . . .
C10 C 0.5542(3) 0.31756(10) 0.41882(7) 0.0221(3) Uani 1 1 d . . . . .
H10 H 0.450924 0.265245 0.414604 0.027 Uiso 1 1 calc R U . . .
C11 C 0.6983(3) 0.32539(10) 0.46963(7) 0.0241(3) Uani 1 1 d . . . . .
H11 H 0.691168 0.278542 0.500661 0.029 Uiso 1 1 calc R U . . .
C12 C 0.8529(3) 0.40094(10) 0.47566(7) 0.0221(3) Uani 1 1 d . . . . .
C13 C 0.8671(3) 0.47049(10) 0.43046(7) 0.0188(3) Uani 1 1 d . . . . .
C14 C 0.7182(3) 0.46309(10) 0.38037(6) 0.0189(3) Uani 1 1 d . . . . .
H14 H 0.722322 0.510685 0.349785 0.023 Uiso 1 1 calc R U . . .
C15 C 1.1796(3) 0.46619(12) 0.52815(9) 0.0305(4) Uani 1 1 d . . . . .
H15A H 1.307955 0.436607 0.504535 0.037 Uiso 1 1 calc R U . . .
H15B H 1.235306 0.474526 0.570564 0.037 Uiso 1 1 calc R U . . .
C16 C 1.1267(3) 0.56316(11) 0.50111(8) 0.0234(3) Uani 1 1 d . . . . .
C17 C 1.0454(3) 0.55020(10) 0.43465(7) 0.0217(3) Uani 1 1 d . . . . .
H17 H 1.185402 0.530104 0.410523 0.026 Uiso 1 1 calc R U . . .
C18 C 0.9563(3) 0.64029(11) 0.40648(8) 0.0260(3) Uani 1 1 d . . . . .
H18 H 0.818886 0.667749 0.423303 0.031 Uiso 1 1 calc R U . . .
C19 C 1.0555(5) 0.68373(15) 0.36016(10) 0.0460(5) Uani 1 1 d . . . . .
H19A H 1.193205 0.658260 0.342208 0.055 Uiso 1 1 calc R U . . .
H19B H 0.989512 0.740576 0.344651 0.055 Uiso 1 1 calc R U . . .
C20 C 1.3434(3) 0.62511(14) 0.50508(9) 0.0344(4) Uani 1 1 d . . . . .
H20A H 1.470708 0.596057 0.481667 0.052 Uiso 1 1 calc R U . . .
H20B H 1.391017 0.631409 0.547818 0.052 Uiso 1 1 calc R U . . .
H20C H 1.308394 0.687846 0.488312 0.052 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 C9 1.3734(18) . ?
O1 C7 1.4396(18) . ?
N1 N2 1.2285(19) . ?
N1 C16 1.496(2) . ?
C1 C6 1.377(3) . ?
C1 C2 1.379(3) . ?
C1 H1 0.9500 . ?
O2 C12 1.3759(18) . ?
O2 C15 1.426(2) . ?
N2 N3 1.134(2) . ?
C2 C3 1.395(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C4 C7 1.516(2) . ?
C5 C6 1.396(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 C7 1.517(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7 H7 1.0000 . ?
C9 C14 1.3904(19) . ?
C9 C10 1.394(2) . ?
C10 C11 1.390(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.391(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(2) . ?
C13 C14 1.3932(19) . ?
C13 C17 1.521(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.523(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C20 1.518(2) . ?
C16 C17 1.541(2) . ?
C17 C18 1.503(2) . ?
C17 H17 1.0000 . ?
C18 C19 1.315(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9500 . ?
C19 H19B 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C9 O1 C7 118.36(11) . . ?
N2 N1 C16 114.59(13) . . ?
C6 C1 C2 119.52(16) . . ?
C6 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C12 O2 C15 116.12(13) . . ?
N3 N2 N1 174.2(2) . . ?
C1 C2 C3 120.39(18) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.18(17) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.48(15) . . ?
C3 C4 C7 119.69(14) . . ?
C5 C4 C7 120.82(14) . . ?
C4 C5 C6 119.80(16) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.63(17) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C7 C4 113.12(13) . . ?
O1 C7 C8 104.47(12) . . ?
C4 C7 C8 111.80(13) . . ?
O1 C7 H7 109.1 . . ?
C4 C7 H7 109.1 . . ?
C8 C7 H7 109.1 . . ?
O1 C9 C14 115.43(12) . . ?
O1 C9 C10 124.63(13) . . ?
C14 C9 C10 119.94(13) . . ?
C11 C10 C9 118.99(14) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 120.85(14) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
O2 C12 C11 116.44(13) . . ?
O2 C12 C13 122.97(13) . . ?
C11 C12 C13 120.57(14) . . ?
C14 C13 C12 118.09(13) . . ?
C14 C13 C17 120.79(13) . . ?
C12 C13 C17 121.09(13) . . ?
C9 C14 C13 121.53(13) . . ?
C9 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
O2 C15 C16 113.67(12) . . ?
O2 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
O2 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
N1 C16 C20 111.43(13) . . ?
N1 C16 C15 109.53(14) . . ?
C20 C16 C15 109.53(13) . . ?
N1 C16 C17 105.88(12) . . ?
C20 C16 C17 111.62(14) . . ?
C15 C16 C17 108.75(12) . . ?
C18 C17 C13 112.06(12) . . ?
C18 C17 C16 112.97(12) . . ?
C13 C17 C16 110.30(13) . . ?
C18 C17 H17 107.1 . . ?
C13 C17 H17 107.1 . . ?
C16 C17 H17 107.1 . . ?
C19 C18 C17 124.53(19) . . ?
C19 C18 H18 117.7 . . ?
C17 C18 H18 117.7 . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C16 C20 H20A 109.5 . . ?
C16 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C16 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C6 C1 C2 C3 -0.4(3) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C4 C7 178.16(19) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C7 C4 C5 C6 -178.51(17) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C9 O1 C7 C4 -76.67(16) . . . . ?
C9 O1 C7 C8 161.51(12) . . . . ?
C3 C4 C7 O1 149.10(15) . . . . ?
C5 C4 C7 O1 -32.4(2) . . . . ?
C3 C4 C7 C8 -93.30(18) . . . . ?
C5 C4 C7 C8 85.15(19) . . . . ?
C7 O1 C9 C14 -161.19(13) . . . . ?
C7 O1 C9 C10 19.9(2) . . . . ?
O1 C9 C10 C11 179.92(14) . . . . ?
C14 C9 C10 C11 1.0(2) . . . . ?
C9 C10 C11 C12 -1.1(2) . . . . ?
C15 O2 C12 C11 165.01(14) . . . . ?
C15 O2 C12 C13 -16.5(2) . . . . ?
C10 C11 C12 O2 178.24(15) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
O2 C12 C13 C14 -176.74(14) . . . . ?
C11 C12 C13 C14 1.7(2) . . . . ?
O2 C12 C13 C17 5.3(2) . . . . ?
C11 C12 C13 C17 -176.32(14) . . . . ?
O1 C9 C14 C13 -178.58(13) . . . . ?
C10 C9 C14 C13 0.4(2) . . . . ?
C12 C13 C14 C9 -1.8(2) . . . . ?
C17 C13 C14 C9 176.23(13) . . . . ?
C12 O2 C15 C16 44.60(19) . . . . ?
N2 N1 C16 C20 -45.4(2) . . . . ?
N2 N1 C16 C15 75.93(17) . . . . ?
N2 N1 C16 C17 -166.97(13) . . . . ?
O2 C15 C16 N1 55.47(17) . . . . ?
O2 C15 C16 C20 177.96(14) . . . . ?
O2 C15 C16 C17 -59.81(18) . . . . ?
C14 C13 C17 C18 34.11(19) . . . . ?
C12 C13 C17 C18 -147.97(14) . . . . ?
C14 C13 C17 C16 160.89(13) . . . . ?
C12 C13 C17 C16 -21.19(19) . . . . ?
N1 C16 C17 C18 54.28(17) . . . . ?
C20 C16 C17 C18 -67.15(17) . . . . ?
C15 C16 C17 C18 171.90(14) . . . . ?
N1 C16 C17 C13 -71.99(15) . . . . ?
C20 C16 C17 C13 166.58(13) . . . . ?
C15 C16 C17 C13 45.63(16) . . . . ?
C13 C17 C18 C19 -119.4(2) . . . . ?
C16 C17 C18 C19 115.3(2) . . . . ?
 
_refine_diff_density_max    0.239
_refine_diff_density_min   -0.167
_refine_diff_density_rms    0.036



