#------------------------------------------------------------------------------
#$Date: 2021-01-07 06:47:38 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260662 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/71/7127144.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_7127144
loop_
_publ_author_name
'Zhang, Xiao-Wen'
'Zhang, Hui'
'Wang, Hu-Chong'
'Zhu, Ming-Hui'
'Cong, Hengjiang'
'Liu, Wen-Bo'
_publ_section_title
;
 Pd-catalyzed arylation/aza-Michael addition cascade to C2-spiroindolines
 and azabicyclo[3.2.2]nonanones.
;
_journal_issue                   80
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              12013
_journal_page_last               12016
_journal_paper_doi               10.1039/d0cc04935b
_journal_volume                  56
_journal_year                    2020
_chemical_formula_sum            'C20 H21 N O'
_chemical_formula_weight         291.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2019-03-26 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.780(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.162(15)
_cell_length_b                   19.10(3)
_cell_length_c                   8.941(13)
_cell_measurement_reflns_used    5114
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.34
_cell_measurement_theta_min      4.26
_cell_volume                     1633(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker Kappa APEX-Duo CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11359
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.342
_diffrn_reflns_theta_min         4.265
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2012/1 (Bruker,2012)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4432
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0484
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0731P)²+0.2852P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1373
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3691
_reflns_number_total             4432
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc04935b2.cif
_cod_data_source_block           mx4_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7127144--7127145.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7127144
_shelx_shelxl_version_number     2016/4
_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_min   0.994
_shelx_estimated_absorpt_t_max   0.997
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'
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
N1 N 0.74973(9) 0.47534(5) 0.67381(11) 0.0353(2) Uani 1 1 d . . . . .
H1 H 0.4152(18) 0.4458(9) 0.8743(19) 0.059(4) Uiso 1 1 d . . . . .
O1 O 0.81444(13) 0.65660(6) 1.06696(11) 0.0665(3) Uani 1 1 d . . . . .
C1 C 0.57465(11) 0.53719(6) 0.74246(13) 0.0366(2) Uani 1 1 d . . . . .
C2 C 0.57309(11) 0.46015(6) 0.78042(12) 0.0351(2) Uani 1 1 d . . . . .
H2 H 0.4442(19) 0.3195(10) 0.899(2) 0.073(5) Uiso 1 1 d . . . . .
C3 C 0.48628(13) 0.42154(7) 0.84126(14) 0.0437(3) Uani 1 1 d . . . . .
H3 H 0.622(2) 0.2635(11) 0.824(2) 0.077(5) Uiso 1 1 d . . . . .
C6 C 0.69617(15) 0.35389(6) 0.75031(17) 0.0496(3) Uani 1 1 d . . . . .
H6 H 0.733(2) 0.4174(10) 0.125(2) 0.071(5) Uiso 1 1 d . . . . .
C5 C 0.60739(18) 0.31563(7) 0.81192(19) 0.0597(4) Uani 1 1 d . . . . .
H5 H 0.7520(17) 0.4837(9) 0.3585(18) 0.056(4) Uiso 1 1 d . . . . .
C4 C 0.50412(16) 0.34836(8) 0.85663(17) 0.0557(3) Uani 1 1 d . . . . .
H4 H 0.7667(17) 0.3302(9) 0.7177(18) 0.054(4) Uiso 1 1 d . . . . .
C7 C 0.67748(11) 0.42667(5) 0.73485(12) 0.0356(2) Uani 1 1 d . . . . .
H7 H 0.845(2) 0.3050(10) 0.150(2) 0.075(5) Uiso 1 1 d . . . . .
C8 C 0.72064(10) 0.54732(5) 0.72201(11) 0.0317(2) Uani 1 1 d . . . . .
H8 H 0.9798(19) 0.2643(11) 0.404(2) 0.075(5) Uiso 1 1 d . . . . .
C9 C 0.71534(14) 0.60222(6) 0.59503(13) 0.0408(2) Uani 1 1 d . . . . .
H9 H 1.0025(18) 0.3335(9) 0.635(2) 0.064(5) Uiso 1 1 d . . . . .
C10 C 0.67887(17) 0.67498(7) 0.64387(16) 0.0507(3) Uani 1 1 d . . . . .
H10 H 0.9367(16) 0.5030(8) 0.6618(17) 0.048(4) Uiso 1 1 d . . . . .
C11 C 0.78334(18) 0.69853(7) 0.80413(17) 0.0535(3) Uani 1 1 d . . . . .
H11 H 0.9449(16) 0.4311(8) 0.7594(18) 0.051(4) Uiso 1 1 d . . . . .
C12 C 0.80937(12) 0.64302(6) 0.93187(14) 0.0427(3) Uani 1 1 d . . . . .
H12 H 0.9252(18) 0.5693(9) 0.8716(18) 0.056(4) Uiso 1 1 d . . . . .
C13 C 0.83184(12) 0.56878(6) 0.88293(13) 0.0390(2) Uani 1 1 d . . . . .
H13 H 0.8320(15) 0.5360(8) 0.9671(18) 0.051(4) Uiso 1 1 d . . . . .
C14 C 0.88774(11) 0.45765(6) 0.66405(14) 0.0398(2) Uani 1 1 d . . . . .
H14 H 0.879(2) 0.7065(10) 0.788(2) 0.074(5) Uiso 1 1 d . . . . .
C15 C 0.87717(10) 0.41444(6) 0.51693(13) 0.0357(2) Uani 1 1 d . . . . .
H15 H 0.7537(18) 0.7412(10) 0.843(2) 0.069(5) Uiso 1 1 d . . . . .
C16 C 0.94567(14) 0.35005(7) 0.52969(15) 0.0454(3) Uani 1 1 d . . . . .
H16 H 0.8090(16) 0.6035(8) 0.5787(17) 0.051(4) Uiso 1 1 d . . . . .
C17 C 0.93381(16) 0.31012(7) 0.39441(17) 0.0544(3) Uani 1 1 d . . . . .
H17 H 0.6444(17) 0.5868(8) 0.4912(19) 0.055(4) Uiso 1 1 d . . . . .
C18 C 0.85383(15) 0.33450(8) 0.24526(17) 0.0554(3) Uani 1 1 d . . . . .
H18 H 0.4974(15) 0.5480(7) 0.6376(17) 0.043(3) Uiso 1 1 d . . . . .
C19 C 0.78748(14) 0.39935(8) 0.23045(16) 0.0536(3) Uani 1 1 d . . . . .
H19 H 0.5630(15) 0.5672(8) 0.8254(17) 0.051(4) Uiso 1 1 d . . . . .
C20 C 0.79909(13) 0.43907(7) 0.36595(15) 0.0450(3) Uani 1 1 d . . . . .
H21 H 0.6760(18) 0.7096(9) 0.562(2) 0.066(5) Uiso 1 1 d . . . . .
H20 H 0.5810(17) 0.6737(8) 0.6505(18) 0.053(4) 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 0.0033 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'
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
C7 N1 C14 120.30(12) . . ?
C7 N1 C8 108.38(12) . . ?
C14 N1 C8 120.75(8) . . ?
C2 C1 C8 103.22(8) . . ?
C2 C1 H18 109.9(8) . . ?
C8 C1 H18 109.4(8) . . ?
C2 C1 H19 112.9(9) . . ?
C8 C1 H19 112.3(9) . . ?
H18 C1 H19 109.0(12) . . ?
C3 C2 C7 120.64(14) . . ?
C3 C2 C1 131.22(11) . . ?
C7 C2 C1 108.07(10) . . ?
C2 C3 C4 119.01(13) . . ?
C2 C3 H1 119.6(10) . . ?
C4 C3 H1 121.4(10) . . ?
C7 C6 C5 117.95(14) . . ?
C7 C6 H4 121.4(10) . . ?
C5 C6 H4 120.6(10) . . ?
C4 C5 C6 121.60(15) . . ?
C4 C5 H3 120.7(11) . . ?
C6 C5 H3 117.7(11) . . ?
C5 C4 C3 120.13(12) . . ?
C5 C4 H2 118.8(11) . . ?
C3 C4 H2 121.1(11) . . ?
C6 C7 N1 128.52(12) . . ?
C6 C7 C2 120.67(11) . . ?
N1 C7 C2 110.80(13) . . ?
N1 C8 C9 112.03(12) . . ?
N1 C8 C13 110.83(9) . . ?
C9 C8 C13 109.73(12) . . ?
N1 C8 C1 101.94(9) . . ?
C9 C8 C1 111.93(9) . . ?
C13 C8 C1 110.19(12) . . ?
C8 C9 C10 111.04(13) . . ?
C8 C9 H16 108.9(9) . . ?
C10 C9 H16 110.3(9) . . ?
C8 C9 H17 108.5(9) . . ?
C10 C9 H17 111.1(9) . . ?
H16 C9 H17 106.8(12) . . ?
C11 C10 C9 111.89(12) . . ?
C11 C10 H21 109.7(10) . . ?
C9 C10 H21 110.2(10) . . ?
C11 C10 H20 109.5(9) . . ?
C9 C10 H20 109.2(9) . . ?
H21 C10 H20 106.2(13) . . ?
C12 C11 C10 112.84(13) . . ?
C12 C11 H14 106.0(11) . . ?
C10 C11 H14 107.1(10) . . ?
C12 C11 H15 108.4(10) . . ?
C10 C11 H15 112.2(11) . . ?
H14 C11 H15 110.1(15) . . ?
O1 C12 C11 122.42(14) . . ?
O1 C12 C13 121.48(12) . . ?
C11 C12 C13 116.09(14) . . ?
C12 C13 C8 112.26(10) . . ?
C12 C13 H12 105.2(10) . . ?
C8 C13 H12 109.3(9) . . ?
C12 C13 H13 109.6(9) . . ?
C8 C13 H13 110.8(9) . . ?
H12 C13 H13 109.5(13) . . ?
N1 C14 C15 112.60(9) . . ?
N1 C14 H10 107.0(9) . . ?
C15 C14 H10 109.9(8) . . ?
N1 C14 H11 111.0(9) . . ?
C15 C14 H11 108.3(9) . . ?
H10 C14 H11 107.9(12) . . ?
C20 C15 C16 118.66(11) . . ?
C20 C15 C14 120.17(14) . . ?
C16 C15 C14 121.16(11) . . ?
C15 C16 C17 120.90(13) . . ?
C15 C16 H9 118.7(10) . . ?
C17 C16 H9 120.4(10) . . ?
C18 C17 C16 119.93(15) . . ?
C18 C17 H8 119.2(11) . . ?
C16 C17 H8 120.8(11) . . ?
C17 C18 C19 119.78(13) . . ?
C17 C18 H7 119.0(11) . . ?
C19 C18 H7 121.2(11) . . ?
C18 C19 C20 120.17(14) . . ?
C18 C19 H6 120.2(11) . . ?
C20 C19 H6 119.6(11) . . ?
C15 C20 C19 120.53(15) . . ?
C15 C20 H5 118.0(9) . . ?
C19 C20 H5 121.5(9) . . ?
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
N1 C7 1.4044(18) . ?
N1 C14 1.474(2) . ?
N1 C8 1.500(2) . ?
O1 C12 1.219(2) . ?
C1 C2 1.511(3) . ?
C1 C8 1.567(3) . ?
C1 H18 1.020(14) . ?
C1 H19 0.976(15) . ?
C2 C3 1.3938(19) . ?
C2 C7 1.412(2) . ?
C3 C4 1.410(3) . ?
C3 H1 0.984(17) . ?
C6 C7 1.403(3) . ?
C6 C5 1.410(2) . ?
C6 H4 0.972(17) . ?
C5 C4 1.391(3) . ?
C5 H3 1.01(2) . ?
C4 H2 0.985(19) . ?
C8 C9 1.533(2) . ?
C8 C13 1.554(2) . ?
C9 C10 1.539(2) . ?
C9 H16 1.011(15) . ?
C9 H17 1.007(16) . ?
C10 C11 1.534(3) . ?
C10 H21 0.982(19) . ?
C10 H20 1.016(16) . ?
C11 C12 1.515(2) . ?
C11 H14 1.042(19) . ?
C11 H15 0.970(19) . ?
C12 C13 1.524(2) . ?
C13 H12 0.988(17) . ?
C13 H13 0.978(16) . ?
C14 C15 1.526(2) . ?
C14 H10 1.002(16) . ?
C14 H11 0.992(16) . ?
C15 C20 1.396(2) . ?
C15 C16 1.399(2) . ?
C16 C17 1.400(2) . ?
C16 H9 0.973(18) . ?
C17 C18 1.386(3) . ?
C17 H8 0.98(2) . ?
C18 C19 1.395(3) . ?
C18 H7 1.00(2) . ?
C19 C20 1.400(2) . ?
C19 H6 0.978(18) . ?
C20 H5 0.969(17) . ?
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
C8 C1 C2 C3 165.64(11) . . . . ?
C8 C1 C2 C7 -17.57(11) . . . . ?
C7 C2 C3 C4 -0.04(17) . . . . ?
C1 C2 C3 C4 176.41(12) . . . . ?
C7 C6 C5 C4 -0.1(2) . . . . ?
C6 C5 C4 C3 -0.2(2) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C5 C6 C7 N1 -178.35(12) . . . . ?
C5 C6 C7 C2 0.22(19) . . . . ?
C14 N1 C7 C6 -19.91(17) . . . . ?
C8 N1 C7 C6 -164.80(12) . . . . ?
C14 N1 C7 C2 161.41(9) . . . . ?
C8 N1 C7 C2 16.52(12) . . . . ?
C3 C2 C7 C6 -0.17(16) . . . . ?
C1 C2 C7 C6 -177.37(11) . . . . ?
C3 C2 C7 N1 178.63(10) . . . . ?
C1 C2 C7 N1 1.43(12) . . . . ?
C7 N1 C8 C9 -146.12(10) . . . . ?
C14 N1 C8 C9 69.18(13) . . . . ?
C7 N1 C8 C13 90.95(15) . . . . ?
C14 N1 C8 C13 -53.75(14) . . . . ?
C7 N1 C8 C1 -26.30(11) . . . . ?
C14 N1 C8 C1 -171.00(9) . . . . ?
C2 C1 C8 N1 25.85(11) . . . . ?
C2 C1 C8 C9 145.75(9) . . . . ?
C2 C1 C8 C13 -91.86(11) . . . . ?
N1 C8 C9 C10 177.46(10) . . . . ?
C13 C8 C9 C10 -58.99(15) . . . . ?
C1 C8 C9 C10 63.67(13) . . . . ?
C8 C9 C10 C11 57.53(17) . . . . ?
C9 C10 C11 C12 -49.07(17) . . . . ?
C10 C11 C12 O1 -136.41(15) . . . . ?
C10 C11 C12 C13 44.71(18) . . . . ?
O1 C12 C13 C8 134.10(14) . . . . ?
C11 C12 C13 C8 -47.01(16) . . . . ?
N1 C8 C13 C12 177.37(9) . . . . ?
C9 C8 C13 C12 53.12(14) . . . . ?
C1 C8 C13 C12 -70.56(13) . . . . ?
C7 N1 C14 C15 82.03(15) . . . . ?
C8 N1 C14 C15 -137.40(10) . . . . ?
N1 C14 C15 C20 55.32(15) . . . . ?
N1 C14 C15 C16 -125.19(12) . . . . ?
C20 C15 C16 C17 -1.50(19) . . . . ?
C14 C15 C16 C17 179.01(12) . . . . ?
C15 C16 C17 C18 0.3(2) . . . . ?
C16 C17 C18 C19 1.1(2) . . . . ?
C17 C18 C19 C20 -1.4(2) . . . . ?
C16 C15 C20 C19 1.26(18) . . . . ?
C14 C15 C20 C19 -179.23(11) . . . . ?
C18 C19 C20 C15 0.1(2) . . . . ?
