#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/76/1507699.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_1507699
loop_
_publ_author_name
'Xu, Qing-Long'
'Dai, Li-Xin'
'You, Shu-Li'
_publ_section_title
;
 Enantioselective synthesis of tetrahydroisoquinolines via
 iridium-catalyzed intramolecular Friedel-Crafts-type allylic alkylation
 of phenols.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2579
_journal_page_last               2581
_journal_paper_doi               10.1021/ol3008793
_journal_volume                  14
_journal_year                    2012
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H20 Br N O2'
_chemical_formula_weight         374.27
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 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                 108.305(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   27.921(4)
_cell_length_b                   7.0957(10)
_cell_length_c                   8.9295(13)
_cell_measurement_reflns_used    2360
_cell_measurement_temperature    133(2)
_cell_measurement_theta_max      28.59
_cell_measurement_theta_min      2.40
_cell_volume                     1679.6(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      133(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0373
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6131
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.40
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.457
_exptl_absorpt_correction_T_max  0.8870
_exptl_absorpt_correction_T_min  0.5462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.013(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3273
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0255P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0637
_refine_ls_wR_factor_ref         0.0781
_reflns_number_gt                2725
_reflns_number_total             3273
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol3008793_si_002.cif
_cod_data_source_block           dm11313
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

 Adding full bibliography for 1507699.cif.
;
_cod_original_sg_symbol_H-M      C2
_cod_database_code               1507699
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.245172(14) 0.75592(6) 0.30211(4) 0.02055(10) Uani 1 1 d .
C1 C 0.25076(14) 0.7444(9) 0.0955(4) 0.0179(7) Uani 1 1 d .
C2 C 0.20689(12) 0.7600(9) -0.0293(4) 0.0173(7) Uani 1 1 d .
C3 C 0.21039(12) 0.7534(10) -0.1831(3) 0.0180(6) Uani 1 1 d .
C4 C 0.25671(13) 0.7420(11) -0.2055(4) 0.0175(8) Uani 1 1 d .
H4 H 0.2589 0.7438 -0.3095 0.021 Uiso 1 1 calc R
C5 C 0.30042(14) 0.7280(6) -0.0781(4) 0.0140(9) Uani 1 1 d .
C6 C 0.35065(14) 0.7051(5) -0.1089(4) 0.0138(9) Uani 1 1 d .
H6 H 0.3513 0.5765 -0.1541 0.017 Uiso 1 1 calc R
C7 C 0.39499(14) 0.7188(5) 0.0431(4) 0.0174(10) Uani 1 1 d .
H7A H 0.4259 0.6715 0.0241 0.021 Uiso 1 1 calc R
H7B H 0.4006 0.8523 0.0760 0.021 Uiso 1 1 calc R
C8 C 0.34511(15) 0.7031(5) 0.2154(4) 0.0199(9) Uani 1 1 d .
H8A H 0.3572 0.8286 0.2600 0.024 Uiso 1 1 calc R
H8B H 0.3371 0.6284 0.2981 0.024 Uiso 1 1 calc R
C9 C 0.29815(15) 0.7260(6) 0.0756(4) 0.0163(9) Uani 1 1 d .
C10 C 0.35796(15) 0.8466(6) -0.2258(4) 0.0188(8) Uani 1 1 d .
H10 H 0.3547 0.9766 -0.2055 0.023 Uiso 1 1 calc R
C11 C 0.36865(16) 0.7995(5) -0.3554(4) 0.0252(11) Uani 1 1 d .
H11A H 0.3721 0.6705 -0.3787 0.030 Uiso 1 1 calc R
H11B H 0.3729 0.8946 -0.4250 0.030 Uiso 1 1 calc R
C12 C 0.16742(15) 0.7669(11) -0.4586(4) 0.0267(9) Uani 1 1 d .
H12A H 0.1854 0.8806 -0.4733 0.040 Uiso 1 1 calc R
H12B H 0.1331 0.7683 -0.5331 0.040 Uiso 1 1 calc R
H12C H 0.1853 0.6551 -0.4776 0.040 Uiso 1 1 calc R
C13 C 0.43054(16) 0.5874(6) 0.3072(4) 0.0236(9) Uani 1 1 d .
H13A H 0.4207 0.5414 0.3980 0.028 Uiso 1 1 calc R
H13B H 0.4468 0.7120 0.3355 0.028 Uiso 1 1 calc R
C14 C 0.46739(16) 0.4527(6) 0.2749(5) 0.0213(9) Uani 1 1 d .
C15 C 0.51090(16) 0.5147(6) 0.2429(5) 0.0235(9) Uani 1 1 d .
H15 H 0.5181 0.6457 0.2453 0.028 Uiso 1 1 calc R
C16 C 0.5437(2) 0.3868(7) 0.2076(6) 0.0304(12) Uani 1 1 d .
H16 H 0.5725 0.4319 0.1834 0.036 Uiso 1 1 calc R
C17 C 0.5351(2) 0.2002(7) 0.2073(7) 0.0385(15) Uani 1 1 d .
H17 H 0.5579 0.1139 0.1840 0.046 Uiso 1 1 calc R
C18 C 0.49273(19) 0.1346(7) 0.2413(7) 0.0467(14) Uani 1 1 d .
H18 H 0.4864 0.0030 0.2413 0.056 Uiso 1 1 calc R
C19 C 0.45969(15) 0.2609(11) 0.2752(5) 0.0372(9) Uani 1 1 d .
H19 H 0.4311 0.2142 0.2992 0.045 Uiso 1 1 calc R
N1 N 0.38513(12) 0.6081(4) 0.1693(3) 0.0171(7) Uani 1 1 d .
O1 O 0.16095(9) 0.7769(5) -0.0061(3) 0.0188(6) Uani 1 1 d .
H1 H 0.1444 0.8636 -0.0634 0.028 Uiso 1 1 calc R
O2 O 0.16520(9) 0.7621(7) -0.3013(2) 0.0213(5) 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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 C1 C9 122.9(3)
C2 C1 Br1 117.3(2)
C9 C1 Br1 119.8(3)
O1 C2 C1 121.5(3)
O1 C2 C3 120.4(3)
C1 C2 C3 118.0(3)
O2 C3 C4 125.0(3)
O2 C3 C2 114.9(3)
C4 C3 C2 120.1(3)
C3 C4 C5 120.8(3)
C3 C4 H4 119.6
C5 C4 H4 119.6
C4 C5 C9 120.5(3)
C4 C5 C6 118.9(3)
C9 C5 C6 120.5(3)
C10 C6 C5 112.8(3)
C10 C6 C7 109.0(3)
C5 C6 C7 111.7(3)
C10 C6 H6 107.7
C5 C6 H6 107.7
C7 C6 H6 107.7
N1 C7 C6 110.7(3)
N1 C7 H7A 109.5
C6 C7 H7A 109.5
N1 C7 H7B 109.5
C6 C7 H7B 109.5
H7A C7 H7B 108.1
N1 C8 C9 110.9(3)
N1 C8 H8A 109.5
C9 C8 H8A 109.5
N1 C8 H8B 109.5
C9 C8 H8B 109.5
H8A C8 H8B 108.0
C5 C9 C1 117.6(3)
C5 C9 C8 121.3(3)
C1 C9 C8 121.2(3)
C11 C10 C6 123.6(4)
C11 C10 H10 118.2
C6 C10 H10 118.2
C10 C11 H11A 120.0
C10 C11 H11B 120.0
H11A C11 H11B 120.0
O2 C12 H12A 109.5
O2 C12 H12B 109.5
H12A C12 H12B 109.5
O2 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
N1 C13 C14 111.5(3)
N1 C13 H13A 109.3
C14 C13 H13A 109.3
N1 C13 H13B 109.3
C14 C13 H13B 109.3
H13A C13 H13B 108.0
C19 C14 C15 117.1(4)
C19 C14 C13 120.9(4)
C15 C14 C13 122.0(4)
C16 C15 C14 121.0(4)
C16 C15 H15 119.5
C14 C15 H15 119.5
C17 C16 C15 120.8(5)
C17 C16 H16 119.6
C15 C16 H16 119.6
C16 C17 C18 119.5(5)
C16 C17 H17 120.3
C18 C17 H17 120.3
C19 C18 C17 120.1(5)
C19 C18 H18 120.0
C17 C18 H18 120.0
C14 C19 C18 121.6(5)
C14 C19 H19 119.2
C18 C19 H19 119.2
C7 N1 C8 108.2(3)
C7 N1 C13 112.1(3)
C8 N1 C13 110.0(3)
C2 O1 H1 109.5
C3 O2 C12 116.5(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.901(3)
C1 C2 1.377(4)
C1 C9 1.395(5)
C2 O1 1.367(4)
C2 C3 1.408(4)
C3 O2 1.369(4)
C3 C4 1.371(5)
C4 C5 1.386(5)
C4 H4 0.9500
C5 C9 1.394(4)
C5 C6 1.520(5)
C6 C10 1.508(5)
C6 C7 1.526(5)
C6 H6 1.0000
C7 N1 1.469(4)
C7 H7A 0.9900
C7 H7B 0.9900
C8 N1 1.470(5)
C8 C9 1.508(5)
C8 H8A 0.9900
C8 H8B 0.9900
C10 C11 1.325(5)
C10 H10 0.9500
C11 H11A 0.9500
C11 H11B 0.9500
C12 O2 1.426(4)
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 0.9800
C13 N1 1.471(5)
C13 C14 1.497(6)
C13 H13A 0.9900
C13 H13B 0.9900
C14 C19 1.378(9)
C14 C15 1.403(6)
C15 C16 1.395(7)
C15 H15 0.9500
C16 C17 1.345(8)
C16 H16 0.9500
C17 C18 1.392(8)
C17 H17 0.9500
C18 C19 1.386(8)
C18 H18 0.9500
C19 H19 0.9500
O1 H1 0.8400
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
O1 H1 N1 0.84 2.02 2.850(5) 168.1 4
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 30651894 ChemSpider
