#------------------------------------------------------------------------------
#$Date: 2020-06-24 04:12:00 +0300 (Wed, 24 Jun 2020) $
#$Revision: 253385 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/83/1558398.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1558398
loop_
_publ_author_name
'Inanaga, Kazato'
'Wollenburg, Marco'
'Bachman, Shoshana'
'Hafeman, Nicholas'
'Stoltz, Brian M.'
_publ_section_title
;
 Catalytic Enantioselective Synthesis of Carbocyclic and Heterocyclic
 Spiranes via a Decarboxylative Aldol Cyclization
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02366C
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H19 N O3'
_chemical_formula_sum            'C16 H19 N O3'
_chemical_formula_weight         273.32
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2017-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227),
 SHELXL-2014,
 and manual edit
;
_audit_update_record
;
2020-04-26 deposited with the CCDC.	2020-06-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.925(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.0356(4)
_cell_length_b                   10.8751(9)
_cell_length_c                   10.5262(7)
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    100
_cell_measurement_theta_max      78.21
_cell_measurement_theta_min      4.24
_cell_volume                     684.32(9)
_computing_cell_refinement       'SAINT V8.37A (Bruker-AXS, 2007)'
_computing_data_collection
'APEX3 BIS V6.2.1/2016-03-01 (Bruker-AXS, 2007)'
_computing_data_reduction        'SAINT V8.37A (Bruker-AXS, 2007)'
_computing_molecular_graphics    'DIAMOND 3 (Crystal Impact, 1999)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XT-2014/4 (Sheldrick, 2012)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CMOS Area Detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker PHOTON 100 CMOS'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            34337
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         78.780
_diffrn_reflns_theta_min         4.240
_diffrn_source                   'I\mS HB micro-focus sealed tube'
_diffrn_source_current           1
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatech I\mS HB'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.8741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0930 before and 0.0689 after correction.
The Ratio of minimum to maximum transmission is 0.8876.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
;
 Flack x determined using 1311 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.13(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0287
_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)+(0.0452P)²+0.1077P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0730
_refine_ls_wR_factor_ref         0.0736
_reflns_Friedel_coverage         0.872
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                2867
_reflns_number_total             2909
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02366c2.cif
_cod_data_source_block           p16478
_cod_original_cell_volume        684.32(8)
_cod_database_code               1558398
_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.
;
_shelx_estimated_absorpt_t_max   0.910
_shelx_estimated_absorpt_t_min   0.848
_refine_ls_abs_structure_hooft   0.15(4)
_olex2_refinement_description
;
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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 0.4857(2) 0.61503(12) 0.61173(12) 0.0198(3) Uani 1 1 d . . . . .
O2 O 0.6609(2) 0.35555(12) 0.44462(12) 0.0191(3) Uani 1 1 d . . . . .
H2 H 0.612(5) 0.277(3) 0.431(3) 0.038(7) Uiso 1 1 d . . . . .
O3 O 0.5125(3) 0.35452(15) 0.89447(13) 0.0320(4) Uani 1 1 d . . . . .
N1 N 0.4456(2) 0.41892(14) 0.68892(14) 0.0167(3) Uani 1 1 d . . . . .
C1 C 0.4223(3) 0.50887(16) 0.59537(16) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.3074(3) 0.45543(15) 0.47047(16) 0.0146(3) Uani 1 1 d . . . . .
C3 C 0.2088(3) 0.33321(16) 0.51106(16) 0.0166(3) Uani 1 1 d . . . . .
H3A H 0.047(4) 0.342(2) 0.515(2) 0.014(5) Uiso 1 1 d . . . . .
H3B H 0.225(4) 0.268(2) 0.454(2) 0.017(5) Uiso 1 1 d . . . . .
C4 C 0.3292(3) 0.30430(17) 0.64617(18) 0.0207(4) Uani 1 1 d . . . . .
H4A H 0.224(4) 0.280(3) 0.708(2) 0.027(6) Uiso 1 1 d . . . . .
H4B H 0.444(4) 0.240(2) 0.644(2) 0.021(6) Uiso 1 1 d . . . . .
C5 C 0.4948(3) 0.43727(16) 0.38427(16) 0.0156(3) Uani 1 1 d . . . . .
H5 H 0.565(3) 0.521(2) 0.377(2) 0.013(5) Uiso 1 1 d . . . . .
C6 C 0.4003(3) 0.39714(16) 0.24910(17) 0.0188(4) Uani 1 1 d . . . . .
H6A H 0.332(4) 0.315(2) 0.252(2) 0.023(6) Uiso 1 1 d . . . . .
H6B H 0.525(4) 0.391(2) 0.198(2) 0.017(5) Uiso 1 1 d . . . . .
C7 C 0.2230(3) 0.48783(17) 0.18695(17) 0.0195(4) Uani 1 1 d . . . . .
H7A H 0.289(4) 0.567(2) 0.178(2) 0.018(5) Uiso 1 1 d . . . . .
H7B H 0.163(4) 0.459(2) 0.100(2) 0.025(6) Uiso 1 1 d . . . . .
C8 C 0.0363(3) 0.50140(17) 0.27045(17) 0.0195(4) Uani 1 1 d . . . . .
H8A H -0.078(4) 0.563(2) 0.230(2) 0.016(5) Uiso 1 1 d . . . . .
H8B H -0.044(4) 0.420(2) 0.275(2) 0.014(5) Uiso 1 1 d . . . . .
C9 C 0.1301(3) 0.54541(16) 0.40487(16) 0.0167(3) Uani 1 1 d . . . . .
H9A H 0.004(3) 0.5526(19) 0.4600(17) 0.005(4) Uiso 1 1 d . . . . .
H9B H 0.200(4) 0.628(2) 0.405(2) 0.022(6) Uiso 1 1 d . . . . .
C10 C 0.5527(3) 0.42928(18) 0.81534(17) 0.0201(4) Uani 1 1 d . . . . .
C11 C 0.7218(3) 0.52872(17) 0.84707(16) 0.0177(4) Uani 1 1 d . . . . .
C12 C 0.7088(3) 0.60306(19) 0.95351(17) 0.0209(4) Uani 1 1 d . . . . .
H12 H 0.582(4) 0.593(3) 0.998(3) 0.027(6) Uiso 1 1 d . . . . .
C13 C 0.8724(3) 0.69131(18) 0.98827(17) 0.0215(4) Uani 1 1 d . . . . .
H13 H 0.870(4) 0.745(3) 1.062(2) 0.026(6) Uiso 1 1 d . . . . .
C14 C 1.0521(3) 0.70318(18) 0.92020(18) 0.0213(4) Uani 1 1 d . . . . .
H14 H 1.170(5) 0.761(3) 0.948(3) 0.034(7) Uiso 1 1 d . . . . .
C15 C 1.0660(3) 0.62821(18) 0.81440(18) 0.0219(4) Uani 1 1 d . . . . .
H15 H 1.194(4) 0.636(2) 0.764(2) 0.016(5) Uiso 1 1 d . . . . .
C16 C 0.9002(3) 0.54185(16) 0.77680(17) 0.0204(4) Uani 1 1 d . . . . .
H16 H 0.910(4) 0.489(3) 0.699(2) 0.029(7) Uiso 1 1 d . . . . .
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'
N N 0.0311 0.0180 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0620
0.00 0.00 -1.00 0.0520
0.00 1.00 0.00 0.1050
0.00 -1.00 0.00 0.1150
-1.00 0.00 0.00 0.0570
1.00 0.00 0.00 0.0830
0.00 1.00 1.00 0.0680
-3.00 -1.00 4.00 0.0760
5.00 0.00 -3.00 0.0930
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
C5 O2 H2 108.9(19) . . ?
C1 N1 C4 112.62(14) . . ?
C1 N1 C10 127.47(16) . . ?
C10 N1 C4 119.80(14) . . ?
O1 C1 N1 124.74(16) . . ?
O1 C1 C2 125.60(15) . . ?
N1 C1 C2 109.66(15) . . ?
C1 C2 C3 103.79(13) . . ?
C1 C2 C5 105.78(13) . . ?
C1 C2 C9 110.59(13) . . ?
C3 C2 C5 113.05(14) . . ?
C3 C2 C9 113.64(13) . . ?
C9 C2 C5 109.56(13) . . ?
C2 C3 H3A 110.4(14) . . ?
C2 C3 H3B 113.5(15) . . ?
H3A C3 H3B 106.9(19) . . ?
C4 C3 C2 106.35(14) . . ?
C4 C3 H3A 108.9(12) . . ?
C4 C3 H3B 110.8(14) . . ?
N1 C4 C3 104.75(14) . . ?
N1 C4 H4A 109.8(15) . . ?
N1 C4 H4B 107.4(14) . . ?
C3 C4 H4A 113.3(14) . . ?
C3 C4 H4B 111.4(14) . . ?
H4A C4 H4B 110(2) . . ?
O2 C5 C2 110.05(13) . . ?
O2 C5 H5 108.8(12) . . ?
O2 C5 C6 112.88(14) . . ?
C2 C5 H5 105.8(12) . . ?
C6 C5 C2 111.85(13) . . ?
C6 C5 H5 107.2(12) . . ?
C5 C6 H6A 109.8(15) . . ?
C5 C6 H6B 108.3(13) . . ?
C5 C6 C7 111.34(14) . . ?
H6A C6 H6B 108(2) . . ?
C7 C6 H6A 109.0(15) . . ?
C7 C6 H6B 110.7(13) . . ?
C6 C7 H7A 110.0(14) . . ?
C6 C7 H7B 109.7(15) . . ?
H7A C7 H7B 107(2) . . ?
C8 C7 C6 110.05(14) . . ?
C8 C7 H7A 108.6(13) . . ?
C8 C7 H7B 111.1(15) . . ?
C7 C8 H8A 109.8(13) . . ?
C7 C8 H8B 110.0(12) . . ?
H8A C8 H8B 107.1(17) . . ?
C9 C8 C7 110.78(13) . . ?
C9 C8 H8A 108.9(13) . . ?
C9 C8 H8B 110.2(12) . . ?
C2 C9 H9A 108.6(11) . . ?
C2 C9 H9B 107.7(14) . . ?
C8 C9 C2 111.22(14) . . ?
C8 C9 H9A 110.0(10) . . ?
C8 C9 H9B 112.7(14) . . ?
H9A C9 H9B 106.4(18) . . ?
O3 C10 N1 119.27(17) . . ?
O3 C10 C11 121.84(17) . . ?
N1 C10 C11 118.82(15) . . ?
C12 C11 C10 119.22(16) . . ?
C12 C11 C16 120.00(17) . . ?
C16 C11 C10 120.62(16) . . ?
C11 C12 H12 117.5(16) . . ?
C13 C12 C11 119.77(17) . . ?
C13 C12 H12 122.7(16) . . ?
C12 C13 H13 122.3(16) . . ?
C14 C13 C12 120.43(17) . . ?
C14 C13 H13 117.2(16) . . ?
C13 C14 H14 120.1(16) . . ?
C13 C14 C15 119.81(17) . . ?
C15 C14 H14 120.0(17) . . ?
C14 C15 H15 120.5(13) . . ?
C16 C15 C14 120.19(17) . . ?
C16 C15 H15 119.3(13) . . ?
C11 C16 H16 120.5(15) . . ?
C15 C16 C11 119.77(16) . . ?
C15 C16 H16 119.7(15) . . ?
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 1.221(2) . ?
O2 H2 0.91(4) . ?
O2 C5 1.422(2) . ?
O3 C10 1.212(2) . ?
N1 C1 1.381(2) . ?
N1 C4 1.471(2) . ?
N1 C10 1.401(2) . ?
C1 C2 1.515(2) . ?
C2 C3 1.541(2) . ?
C2 C5 1.557(2) . ?
C2 C9 1.541(2) . ?
C3 H3A 0.99(2) . ?
C3 H3B 0.94(2) . ?
C3 C4 1.538(2) . ?
C4 H4A 1.00(3) . ?
C4 H4B 0.99(3) . ?
C5 H5 1.02(2) . ?
C5 C6 1.522(2) . ?
C6 H6A 0.98(3) . ?
C6 H6B 0.99(2) . ?
C6 C7 1.534(2) . ?
C7 H7A 0.96(3) . ?
C7 H7B 0.98(3) . ?
C7 C8 1.529(2) . ?
C8 H8A 1.01(2) . ?
C8 H8B 1.01(2) . ?
C8 C9 1.527(2) . ?
C9 H9A 1.020(19) . ?
C9 H9B 0.99(3) . ?
C10 C11 1.493(2) . ?
C11 C12 1.392(3) . ?
C11 C16 1.395(2) . ?
C12 H12 0.96(3) . ?
C12 C13 1.389(3) . ?
C13 H13 0.97(3) . ?
C13 C14 1.386(3) . ?
C14 H14 0.96(3) . ?
C14 C15 1.392(3) . ?
C15 H15 0.99(2) . ?
C15 C16 1.390(3) . ?
C16 H16 1.01(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.91(4) 1.89(4) 2.7986(19) 175(3) 2_646
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
O1 C1 C2 C3 -165.21(17) . . . . ?
O1 C1 C2 C5 75.6(2) . . . . ?
O1 C1 C2 C9 -43.0(2) . . . . ?
O2 C5 C6 C7 -179.66(14) . . . . ?
O3 C10 C11 C12 -51.7(3) . . . . ?
O3 C10 C11 C16 123.8(2) . . . . ?
N1 C1 C2 C3 14.98(17) . . . . ?
N1 C1 C2 C5 -104.25(15) . . . . ?
N1 C1 C2 C9 137.20(14) . . . . ?
N1 C10 C11 C12 131.41(18) . . . . ?
N1 C10 C11 C16 -53.1(2) . . . . ?
C1 N1 C4 C3 -3.70(19) . . . . ?
C1 N1 C10 O3 161.61(18) . . . . ?
C1 N1 C10 C11 -21.4(3) . . . . ?
C1 C2 C3 C4 -16.70(17) . . . . ?
C1 C2 C5 O2 60.06(17) . . . . ?
C1 C2 C5 C6 -173.63(14) . . . . ?
C1 C2 C9 C8 171.94(14) . . . . ?
C2 C3 C4 N1 12.86(18) . . . . ?
C2 C5 C6 C7 55.58(18) . . . . ?
C3 C2 C5 O2 -52.86(18) . . . . ?
C3 C2 C5 C6 73.45(18) . . . . ?
C3 C2 C9 C8 -71.81(17) . . . . ?
C4 N1 C1 O1 172.87(17) . . . . ?
C4 N1 C1 C2 -7.32(18) . . . . ?
C4 N1 C10 O3 -14.3(3) . . . . ?
C4 N1 C10 C11 162.72(16) . . . . ?
C5 C2 C3 C4 97.43(16) . . . . ?
C5 C2 C9 C8 55.72(17) . . . . ?
C5 C6 C7 C8 -56.81(19) . . . . ?
C6 C7 C8 C9 58.18(19) . . . . ?
C7 C8 C9 C2 -58.66(18) . . . . ?
C9 C2 C3 C4 -136.87(15) . . . . ?
C9 C2 C5 O2 179.28(13) . . . . ?
C9 C2 C5 C6 -54.41(18) . . . . ?
C10 N1 C1 O1 -3.3(3) . . . . ?
C10 N1 C1 C2 176.56(15) . . . . ?
C10 N1 C4 C3 172.76(15) . . . . ?
C10 C11 C12 C13 176.38(16) . . . . ?
C10 C11 C16 C15 -174.62(17) . . . . ?
C11 C12 C13 C14 -2.1(3) . . . . ?
C12 C11 C16 C15 0.8(3) . . . . ?
C12 C13 C14 C15 1.6(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C11 -1.3(3) . . . . ?
C16 C11 C12 C13 0.9(3) . . . . ?
