#------------------------------------------------------------------------------
#$Date: 2019-11-24 08:05:31 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237234 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/44/1554435.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_1554435
loop_
_publ_author_name
'Liu, Siyuan'
'Zhang, Wenzhu'
'Qu, Jingping'
'Wang, Baomin'
_publ_section_title
;
 Engaging 2-methyl indolenines in a tandem condensation/1,5-hydride
 transfer/cyclization process: construction of a novel
 indolenine--tetrahydroquinoline assembly
;
_journal_issue                   20
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              3008
_journal_paper_doi               10.1039/C8QO00875B
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C22 H24 N2'
_chemical_formula_sum            'C22 H24 N2'
_chemical_formula_weight         316.43
_chemical_melting_point          ?
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2018-08-31 deposited with the CCDC.
2018-09-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 101.60(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.090(6)
_cell_length_b                   8.574(2)
_cell_length_c                   9.447(3)
_cell_measurement_reflns_used    1675
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.3111
_cell_measurement_theta_min      2.5553
_cell_volume                     1752.7(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_molecular_graphics    SHELXP-97
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 9.00cm
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0517
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12935
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.88
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.997
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            coloress
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3091
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0935
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0501P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1018
_refine_ls_wR_factor_ref         0.1190
_reflns_number_gt                1802
_reflns_number_total             3091
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8qo00875b2.cif
_cod_data_source_block           lsy-1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        1752.8(8)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1554435
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
C1 C 0.29248(4) 0.40303(10) 0.21619(9) 0.0408(3) Uani 1 1 d
C2 C 0.36329(4) 0.23637(10) 0.18692(10) 0.0455(3) Uani 1 1 d
C3 C 0.39620(5) 0.09898(12) 0.18804(12) 0.0620(4) Uani 1 1 d
H3 H 0.3795(4) 0.0045(10) 0.2253(9) 0.066(3) Uiso 1 1 d
C4 C 0.44976(5) 0.10274(13) 0.13238(12) 0.0714(4) Uani 1 1 d
H4 H 0.4724(4) 0.0149(11) 0.1305(10) 0.081(3) Uiso 1 1 d
C5 C 0.46938(5) 0.23741(14) 0.07726(13) 0.0732(4) Uani 1 1 d
H5 H 0.5106(4) 0.2400(11) 0.0359(11) 0.091(4) Uiso 1 1 d
C6 C 0.43617(5) 0.37476(13) 0.07691(12) 0.0664(4) Uani 1 1 d
H6 H 0.4475(4) 0.4764(12) 0.0346(10) 0.094(4) Uiso 1 1 d
C7 C 0.38294(4) 0.37257(10) 0.13253(10) 0.0467(3) Uani 1 1 d
C8 C 0.33715(4) 0.49816(10) 0.14734(10) 0.0445(3) Uani 1 1 d
C9 C 0.30530(5) 0.56380(13) -0.00043(12) 0.0673(4) Uani 1 1 d
H9A H 0.2850(5) 0.4805(13) -0.0710(12) 0.120(4) Uiso 1 1 d
H9B H 0.2711(5) 0.6368(11) 0.0125(11) 0.090(3) Uiso 1 1 d
H9C H 0.3367(5) 0.6253(11) -0.0393(10) 0.088(4) Uiso 1 1 d
C10 C 0.36601(5) 0.62873(12) 0.24931(13) 0.0712(4) Uani 1 1 d
H10A H 0.3968(4) 0.6786(11) 0.2087(11) 0.087(3) Uiso 1 1 d
H10B H 0.3320(4) 0.7082(11) 0.2599(10) 0.079(3) Uiso 1 1 d
H10C H 0.3856(5) 0.5816(13) 0.3509(11) 0.103(4) Uiso 1 1 d
C11 C 0.23694(4) 0.47034(10) 0.26330(10) 0.0421(3) Uani 1 1 d
H11 H 0.2317(3) 0.5778(9) 0.2329(8) 0.038(2) Uiso 1 1 d
C12 C 0.17785(4) 0.38509(11) 0.19312(11) 0.0512(3) Uani 1 1 d
H12 H 0.1841(4) 0.2765(10) 0.2189(9) 0.058(3) Uiso 1 1 d
C13 C 0.15587(5) 0.40846(13) 0.03227(12) 0.0676(4) Uani 1 1 d
H13A H 0.1622(4) 0.5215(11) 0.0099(10) 0.083(3) Uiso 1 1 d
H13B H 0.1795(4) 0.3429(11) -0.0276(10) 0.081(3) Uiso 1 1 d
C14 C 0.08732(5) 0.37284(14) 0.00833(14) 0.0873(5) Uani 1 1 d
H14A H 0.0623(5) 0.4188(14) -0.0856(12) 0.118(4) Uiso 1 1 d
H14B H 0.0792(5) 0.2605(15) 0.0089(13) 0.130(5) Uiso 1 1 d
C15 C 0.06797(5) 0.43973(14) 0.14172(14) 0.0744(4) Uani 1 1 d
H15A H 0.0486(5) 0.5450(13) 0.1260(11) 0.111(4) Uiso 1 1 d
H15B H 0.0336(5) 0.3757(12) 0.1732(11) 0.101(4) Uiso 1 1 d
C16 C 0.24435(4) 0.46271(11) 0.42826(10) 0.0501(3) Uani 1 1 d
H16A H 0.2828(4) 0.5247(10) 0.4768(10) 0.075(3) Uiso 1 1 d
H16B H 0.2532(4) 0.3510(10) 0.4557(9) 0.067(3) Uiso 1 1 d
C17 C 0.18743(4) 0.51866(10) 0.47778(11) 0.0508(3) Uani 1 1 d
C18 C 0.12943(4) 0.50794(11) 0.38446(11) 0.0539(3) Uani 1 1 d
C19 C 0.07702(5) 0.56469(12) 0.43145(13) 0.0697(4) Uani 1 1 d
H19 H 0.0356(4) 0.5572(12) 0.3631(11) 0.088(3) Uiso 1 1 d
C20 C 0.08250(5) 0.62610(13) 0.56808(14) 0.0811(4) Uani 1 1 d
H20 H 0.0448(4) 0.6655(11) 0.5962(11) 0.087(3) Uiso 1 1 d
C21 C 0.13846(6) 0.63463(13) 0.66141(13) 0.0797(4) Uani 1 1 d
H21 H 0.1451(5) 0.6757(13) 0.7613(12) 0.105(4) Uiso 1 1 d
C22 C 0.19074(5) 0.58127(12) 0.61459(12) 0.0646(4) Uani 1 1 d
H22 H 0.2329(4) 0.5822(11) 0.6788(10) 0.071(3) Uiso 1 1 d
N1 N 0.30718(3) 0.25840(8) 0.23885(9) 0.0486(3) Uani 1 1 d
N2 N 0.12469(3) 0.44151(10) 0.25073(10) 0.0625(3) Uani 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N1 C1 C11 120.94(8)
N1 C1 C8 115.02(8)
C11 C1 C8 123.97(8)
C7 C2 C3 121.27(9)
C7 C2 N1 111.96(8)
C3 C2 N1 126.77(9)
C2 C3 C4 117.64(10)
C5 C4 C3 121.43(10)
C4 C5 C6 120.54(11)
C7 C6 C5 118.54(10)
C2 C7 C6 120.57(9)
C2 C7 C8 107.67(8)
C6 C7 C8 131.76(9)
C7 C8 C1 99.32(7)
C7 C8 C10 112.31(8)
C1 C8 C10 110.28(8)
C7 C8 C9 111.79(8)
C1 C8 C9 111.48(8)
C10 C8 C9 111.13(8)
C1 C11 C12 111.44(8)
C1 C11 C16 110.95(7)
C12 C11 C16 109.14(8)
N2 C12 C13 102.07(8)
N2 C12 C11 110.99(8)
C13 C12 C11 116.53(9)
C12 C13 C14 103.44(10)
C13 C14 C15 103.82(9)
N2 C15 C14 104.18(9)
C17 C16 C11 112.12(8)
C22 C17 C18 118.72(10)
C22 C17 C16 121.45(9)
C18 C17 C16 119.84(9)
N2 C18 C17 119.78(9)
N2 C18 C19 121.28(9)
C17 C18 C19 118.93(10)
C20 C19 C18 120.34(10)
C21 C20 C19 121.49(11)
C20 C21 C22 118.46(11)
C17 C22 C21 122.03(10)
C1 N1 C2 106.03(8)
C18 N2 C15 123.55(9)
C18 N2 C12 123.97(8)
C15 N2 C12 111.89(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.2888(11)
C1 C11 1.5020(13)
C1 C8 1.5232(13)
C2 C7 1.3805(13)
C2 C3 1.3831(14)
C2 N1 1.4342(13)
C3 C4 1.3884(16)
C4 C5 1.3721(16)
C5 C6 1.3870(15)
C6 C7 1.3812(15)
C7 C8 1.5031(13)
C8 C10 1.5300(14)
C8 C9 1.5380(14)
C11 C12 1.5264(13)
C11 C16 1.5353(14)
C12 N2 1.4716(13)
C12 C13 1.5127(15)
C13 C14 1.5164(16)
C14 C15 1.5219(18)
C15 N2 1.4533(13)
C16 C17 1.5056(14)
C17 C22 1.3878(15)
C17 C18 1.4047(13)
C18 N2 1.3705(14)
C18 C19 1.4073(15)
C19 C20 1.3766(17)
C20 C21 1.3684(16)
C21 C22 1.3944(16)
