#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/84/1518401.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_1518401
loop_
_publ_author_name
'Yang, Qin'
'Xu, Tongyu'
'Yu, Zhengkun'
_publ_section_title
;
 Iron-mediated carboarylation/cyclization of propargylanilines with
 acetals: a concise route to indeno[2,1-c]quinolines.
;
_journal_issue                   24
_journal_name_full               'Organic letters'
_journal_page_first              6310
_journal_page_last               6313
_journal_paper_doi               10.1021/ol503039j
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C22 H14 Cl N'
_chemical_formula_weight         327.79
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 95.033(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9351(15)
_cell_length_b                   10.2398(15)
_cell_length_c                   15.259(2)
_cell_measurement_reflns_used    4097
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      2.40
_cell_volume                     1546.4(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      140(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0409
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14810
_diffrn_reflns_theta_full        30.56
_diffrn_reflns_theta_max         30.56
_diffrn_reflns_theta_min         2.06
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.248
_exptl_absorpt_correction_T_max  0.9637
_exptl_absorpt_correction_T_min  0.9248
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0762P)²+0.1902P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1206
_refine_ls_wR_factor_ref         0.1318
_reflns_number_gt                3654
_reflns_number_total             4707
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol503039j_si_001.cif
_cod_data_source_block           mo_dm14029_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 1518400--1518402.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1518401
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
_atom_site_refinement_flags
Cl1 Cl 0.88620(4) 0.14559(4) 1.01685(3) 0.03534(12) Uani 1 1 d .
N1 N 0.83681(10) 0.42087(12) 0.97250(7) 0.0223(2) Uani 1 1 d .
C1 C 0.70927(12) 0.60399(13) 0.91465(8) 0.0187(2) Uani 1 1 d .
C2 C 0.82866(12) 0.54573(14) 0.95154(8) 0.0213(3) Uani 1 1 d .
H2 H 0.9071 0.5984 0.9619 0.026 Uiso 1 1 calc R
C3 C 0.72384(12) 0.34644(13) 0.95684(8) 0.0197(3) Uani 1 1 d .
C4 C 0.73309(13) 0.21022(14) 0.97487(8) 0.0239(3) Uani 1 1 d .
C5 C 0.62519(15) 0.12906(15) 0.95908(9) 0.0279(3) Uani 1 1 d .
H5 H 0.6344 0.0383 0.9710 0.033 Uiso 1 1 calc R
C6 C 0.50005(14) 0.18022(14) 0.92497(9) 0.0262(3) Uani 1 1 d .
H6 H 0.4248 0.1234 0.9143 0.031 Uiso 1 1 calc R
C7 C 0.48508(13) 0.31000(14) 0.90706(8) 0.0221(3) Uani 1 1 d .
H7 H 0.3995 0.3428 0.8845 0.027 Uiso 1 1 calc R
C8 C 0.59624(12) 0.39641(13) 0.92175(7) 0.0178(2) Uani 1 1 d .
C9 C 0.59220(12) 0.53113(13) 0.90065(7) 0.0176(2) Uani 1 1 d .
C10 C 0.48473(12) 0.61694(13) 0.86076(8) 0.0184(2) Uani 1 1 d .
C11 C 0.34836(13) 0.59577(15) 0.83490(9) 0.0236(3) Uani 1 1 d .
H11 H 0.3086 0.5126 0.8425 0.028 Uiso 1 1 calc R
C12 C 0.27178(13) 0.69812(16) 0.79789(9) 0.0273(3) Uani 1 1 d .
H12 H 0.1788 0.6846 0.7801 0.033 Uiso 1 1 calc R
C13 C 0.32869(13) 0.81983(15) 0.78637(9) 0.0267(3) Uani 1 1 d .
H13 H 0.2744 0.8885 0.7607 0.032 Uiso 1 1 calc R
C14 C 0.46406(14) 0.84232(14) 0.81194(9) 0.0239(3) Uani 1 1 d .
H14 H 0.5032 0.9256 0.8038 0.029 Uiso 1 1 calc R
C15 C 0.54074(12) 0.74096(13) 0.84954(8) 0.0196(2) Uani 1 1 d .
C16 C 0.68971(12) 0.74194(13) 0.88160(8) 0.0203(2) Uani 1 1 d .
H16 H 0.7064 0.8049 0.9315 0.024 Uiso 1 1 calc R
C17 C 0.78036(12) 0.77438(13) 0.80950(9) 0.0211(3) Uani 1 1 d .
C18 C 0.78163(14) 0.69187(16) 0.73745(9) 0.0267(3) Uani 1 1 d .
H18 H 0.7258 0.6164 0.7340 0.032 Uiso 1 1 calc R
C19 C 0.86329(15) 0.71799(18) 0.67035(10) 0.0335(3) Uani 1 1 d .
H19 H 0.8635 0.6606 0.6215 0.040 Uiso 1 1 calc R
C20 C 0.94449(14) 0.82795(19) 0.67491(11) 0.0372(4) Uani 1 1 d .
H20 H 1.0006 0.8463 0.6291 0.045 Uiso 1 1 calc R
C21 C 0.94373(14) 0.91044(17) 0.74583(12) 0.0374(4) Uani 1 1 d .
H21 H 0.9998 0.9857 0.7490 0.045 Uiso 1 1 calc R
C22 C 0.86127(14) 0.88452(15) 0.81324(10) 0.0287(3) Uani 1 1 d .
H22 H 0.8607 0.9426 0.8618 0.034 Uiso 1 1 calc R
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'
Cl Cl 0.1484 0.1585 '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
C2 N1 C3 117.93(11)
C9 C1 C2 120.23(12)
C9 C1 C16 111.84(11)
C2 C1 C16 127.84(12)
N1 C2 C1 122.83(12)
N1 C2 H2 118.6
C1 C2 H2 118.6
N1 C3 C4 118.48(12)
N1 C3 C8 123.86(12)
C4 C3 C8 117.65(12)
C5 C4 C3 121.85(12)
C5 C4 Cl1 119.04(11)
C3 C4 Cl1 119.10(10)
C4 C5 C6 119.68(13)
C4 C5 H5 120.2
C6 C5 H5 120.2
C7 C6 C5 121.00(13)
C7 C6 H6 119.5
C5 C6 H6 119.5
C6 C7 C8 120.48(12)
C6 C7 H7 119.8
C8 C7 H7 119.8
C9 C8 C7 124.46(11)
C9 C8 C3 116.17(11)
C7 C8 C3 119.32(12)
C1 C9 C8 118.93(11)
C1 C9 C10 108.15(11)
C8 C9 C10 132.86(11)
C11 C10 C15 119.48(12)
C11 C10 C9 132.49(12)
C15 C10 C9 108.03(11)
C12 C11 C10 118.87(13)
C12 C11 H11 120.6
C10 C11 H11 120.6
C11 C12 C13 121.07(13)
C11 C12 H12 119.5
C13 C12 H12 119.5
C12 C13 C14 120.67(13)
C12 C13 H13 119.7
C14 C13 H13 119.7
C15 C14 C13 118.55(13)
C15 C14 H14 120.7
C13 C14 H14 120.7
C14 C15 C10 121.35(12)
C14 C15 C16 127.99(12)
C10 C15 C16 110.65(11)
C1 C16 C15 101.26(10)
C1 C16 C17 112.35(10)
C15 C16 C17 113.04(10)
C1 C16 H16 110.0
C15 C16 H16 110.0
C17 C16 H16 110.0
C22 C17 C18 118.92(13)
C22 C17 C16 121.86(13)
C18 C17 C16 119.22(12)
C19 C18 C17 120.94(14)
C19 C18 H18 119.5
C17 C18 H18 119.5
C20 C19 C18 119.74(16)
C20 C19 H19 120.1
C18 C19 H19 120.1
C21 C20 C19 119.79(14)
C21 C20 H20 120.1
C19 C20 H20 120.1
C20 C21 C22 120.53(15)
C20 C21 H21 119.7
C22 C21 H21 119.7
C17 C22 C21 120.08(15)
C17 C22 H22 120.0
C21 C22 H22 120.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.7295(13)
N1 C2 1.3186(18)
N1 C3 1.3603(17)
C1 C9 1.3825(17)
C1 C2 1.4009(17)
C1 C16 1.5067(19)
C2 H2 0.9500
C3 C4 1.423(2)
C3 C8 1.4271(17)
C4 C5 1.361(2)
C5 C6 1.406(2)
C5 H5 0.9500
C6 C7 1.362(2)
C6 H6 0.9500
C7 C8 1.4175(17)
C7 H7 0.9500
C8 C9 1.4164(19)
C9 C10 1.4726(17)
C10 C11 1.3945(17)
C10 C15 1.4030(19)
C11 C12 1.386(2)
C11 H11 0.9500
C12 C13 1.386(2)
C12 H12 0.9500
C13 C14 1.3863(19)
C13 H13 0.9500
C14 C15 1.3821(18)
C14 H14 0.9500
C15 C16 1.5175(17)
C16 C17 1.5185(17)
C16 H16 1.0000
C17 C22 1.3832(19)
C17 C18 1.387(2)
C18 C19 1.3871(19)
C18 H18 0.9500
C19 C20 1.383(2)
C19 H19 0.9500
C20 C21 1.373(3)
C20 H20 0.9500
C21 C22 1.396(2)
C21 H21 0.9500
C22 H22 0.9500
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
C2 H2 N1 0.95 2.66 3.4396(17) 139.9 3_767
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
C3 N1 C2 C1 0.35(18)
C9 C1 C2 N1 1.61(19)
C16 C1 C2 N1 -174.86(12)
C2 N1 C3 C4 176.76(11)
C2 N1 C3 C8 -2.08(18)
N1 C3 C4 C5 -178.53(12)
C8 C3 C4 C5 0.39(18)
N1 C3 C4 Cl1 0.71(16)
C8 C3 C4 Cl1 179.63(9)
C3 C4 C5 C6 -0.8(2)
Cl1 C4 C5 C6 179.98(10)
C4 C5 C6 C7 0.3(2)
C5 C6 C7 C8 0.6(2)
C6 C7 C8 C9 176.39(12)
C6 C7 C8 C3 -0.95(18)
N1 C3 C8 C9 1.77(17)
C4 C3 C8 C9 -177.09(11)
N1 C3 C8 C7 179.33(11)
C4 C3 C8 C7 0.47(17)
C2 C1 C9 C8 -1.84(17)
C16 C1 C9 C8 175.15(10)
C2 C1 C9 C10 -179.42(11)
C16 C1 C9 C10 -2.42(14)
C7 C8 C9 C1 -177.17(11)
C3 C8 C9 C1 0.25(16)
C7 C8 C9 C10 -0.3(2)
C3 C8 C9 C10 177.11(12)
C1 C9 C10 C11 -178.62(13)
C8 C9 C10 C11 4.3(2)
C1 C9 C10 C15 1.32(13)
C8 C9 C10 C15 -175.79(12)
C15 C10 C11 C12 0.57(19)
C9 C10 C11 C12 -179.49(13)
C10 C11 C12 C13 0.1(2)
C11 C12 C13 C14 -0.2(2)
C12 C13 C14 C15 -0.3(2)
C13 C14 C15 C10 0.97(19)
C13 C14 C15 C16 179.39(12)
C11 C10 C15 C14 -1.11(19)
C9 C10 C15 C14 178.94(11)
C11 C10 C15 C16 -179.78(11)
C9 C10 C15 C16 0.27(13)
C9 C1 C16 C15 2.45(13)
C2 C1 C16 C15 179.16(12)
C9 C1 C16 C17 -118.44(11)
C2 C1 C16 C17 58.27(17)
C14 C15 C16 C1 179.87(12)
C10 C15 C16 C1 -1.57(13)
C14 C15 C16 C17 -59.73(17)
C10 C15 C16 C17 118.83(12)
C1 C16 C17 C22 -128.82(13)
C15 C16 C17 C22 117.33(14)
C1 C16 C17 C18 51.62(16)
C15 C16 C17 C18 -62.23(16)
C22 C17 C18 C19 0.6(2)
C16 C17 C18 C19 -179.84(13)
C17 C18 C19 C20 -0.2(2)
C18 C19 C20 C21 0.0(2)
C19 C20 C21 C22 -0.3(2)
C18 C17 C22 C21 -0.8(2)
C16 C17 C22 C21 179.64(13)
C20 C21 C22 C17 0.6(2)
