#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:23:56 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180260 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/46/7114629.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_7114629
loop_
_publ_author_name
'Virendra Kumar Tiwari'
'Govind Goroba Pawar'
'Himanshu Sekhar Jena'
'Manmohan Kapur'
_publ_section_title
;
 Palladium catalyzed, heteroatom-guided C-H functionalization in the
 synthesis of substituted isoquinolines and dihydroisoquinolines
;
_journal_name_full               Chem.Commun.
_journal_page_first              7322
_journal_paper_doi               10.1039/C4CC03165B
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C21 H23 N O'
_chemical_formula_sum            'C21 H23 N O'
_chemical_formula_weight         305.40
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 102.027(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0609(9)
_cell_length_b                   7.6268(6)
_cell_length_c                   22.661(2)
_cell_measurement_temperature    99(2)
_cell_volume                     1700.7(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      99(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_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  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0392
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            2721
_diffrn_reflns_theta_full        24.90
_diffrn_reflns_theta_max         24.90
_diffrn_reflns_theta_min         2.82
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656.0
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2649
_refine_ls_number_restraints     59
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0388
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1362
_reflns_number_gt                2351
_reflns_number_total             2649
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc03165b2.cif
_cod_data_source_block           790
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7114629
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
O1 O 0.73802(16) 0.5954(2) 0.97347(10) 0.0284(6) Uani 1 1 d U
N1 N 0.63005(19) 0.6087(2) 0.87482(11) 0.0189(7) Uani 1 1 d U
C6 C 0.5006(2) 0.4024(3) 0.77713(13) 0.0209(8) Uani 1 1 d U
C7 C 0.5547(2) 0.5776(3) 0.76726(14) 0.0164(7) Uani 1 1 d U
C8 C 0.5447(2) 0.6485(3) 0.70605(14) 0.0199(8) Uani 1 1 d U
C1 C 0.4943(2) 0.3526(3) 0.83582(13) 0.0193(8) Uani 1 1 d U
C5 C 0.4666(2) 0.2803(3) 0.73059(14) 0.0236(8) Uani 1 1 d U
H5 H 0.4689 0.3138 0.6904 0.028 Uiso 1 1 calc R
C14 C 0.6222(2) 0.6662(3) 0.81567(14) 0.0180(7) Uani 1 1 d U
H14 H 0.6665 0.7725 0.8093 0.022 Uiso 1 1 calc R
C9 C 0.4184(2) 0.6714(3) 0.66752(15) 0.0229(8) Uani 1 1 d U
H9 H 0.3385 0.6377 0.6807 0.027 Uiso 1 1 calc R
C17 C 0.5210(2) 0.4885(3) 0.88535(13) 0.0229(8) Uani 1 1 d U
H17 H 0.5529 0.4276 0.9248 0.028 Uiso 1 1 calc R
C13 C 0.6612(2) 0.6986(3) 0.68524(14) 0.0256(8) Uani 1 1 d U
H13 H 0.7485 0.6848 0.7106 0.031 Uiso 1 1 calc R
C15 C 0.7352(2) 0.6483(3) 0.92217(15) 0.0214(8) Uani 1 1 d U
C10 C 0.4071(2) 0.7423(3) 0.61041(15) 0.0251(8) Uani 1 1 d U
H10 H 0.3201 0.7572 0.5849 0.030 Uiso 1 1 calc R
C2 C 0.4570(2) 0.1824(3) 0.84700(14) 0.0256(8) Uani 1 1 d U
H2 H 0.4532 0.1482 0.8869 0.031 Uiso 1 1 calc R
C11 C 0.5236(3) 0.7919(3) 0.59032(15) 0.0293(9) Uani 1 1 d U
H11 H 0.5166 0.8414 0.5513 0.035 Uiso 1 1 calc R
C4 C 0.4294(2) 0.1104(3) 0.74221(15) 0.0270(8) Uani 1 1 d U
H4 H 0.4071 0.0281 0.7102 0.032 Uiso 1 1 calc R
C3 C 0.4251(2) 0.0618(3) 0.80021(15) 0.0276(8) Uani 1 1 d U
H3 H 0.4003 -0.0545 0.8083 0.033 Uiso 1 1 calc R
C18 C 0.3897(2) 0.5894(3) 0.88759(14) 0.0249(8) Uani 1 1 d U
H18A H 0.3580 0.6490 0.8484 0.030 Uiso 1 1 calc R
H18B H 0.3188 0.5039 0.8926 0.030 Uiso 1 1 calc R
C19 C 0.4032(2) 0.7250(3) 0.93743(14) 0.0239(8) Uani 1 1 d U
H19A H 0.4632 0.8208 0.9293 0.029 Uiso 1 1 calc R
H19B H 0.4464 0.6700 0.9763 0.029 Uiso 1 1 calc R
C16 C 0.8497(2) 0.7574(3) 0.90763(15) 0.0280(8) Uani 1 1 d U
H16A H 0.9193 0.7753 0.9444 0.042 Uiso 1 1 calc R
H16B H 0.8142 0.8713 0.8916 0.042 Uiso 1 1 calc R
H16C H 0.8898 0.6964 0.8775 0.042 Uiso 1 1 calc R
C20 C 0.2663(3) 0.8016(3) 0.94277(15) 0.0302(9) Uani 1 1 d U
H20A H 0.2249 0.8599 0.9043 0.036 Uiso 1 1 calc R
H20B H 0.2053 0.7049 0.9492 0.036 Uiso 1 1 calc R
C12 C 0.6492(3) 0.7680(3) 0.62793(16) 0.0308(9) Uani 1 1 d U
H12 H 0.7289 0.7999 0.6142 0.037 Uiso 1 1 calc R
C21 C 0.2763(3) 0.9325(3) 0.99359(14) 0.0371(9) Uani 1 1 d U
H21A H 0.3155 0.8753 1.0320 0.056 Uiso 1 1 calc R
H21B H 0.1854 0.9765 0.9948 0.056 Uiso 1 1 calc R
H21C H 0.3344 1.0305 0.9869 0.056 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'
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
C15 N1 C14 124.08(19)
C15 N1 C17 118.9(2)
C14 N1 C17 116.9(2)
C5 C6 C1 119.0(2)
C5 C6 C7 122.0(2)
C1 C6 C7 118.8(3)
C14 C7 C8 120.5(2)
C14 C7 C6 118.0(3)
C8 C7 C6 121.3(3)
C9 C8 C13 118.1(3)
C9 C8 C7 120.68(19)
C13 C8 C7 121.2(2)
C2 C1 C6 119.7(3)
C2 C1 C17 121.3(2)
C6 C1 C17 118.95(19)
C4 C5 C6 120.8(2)
C7 C14 N1 122.8(2)
C10 C9 C8 121.4(2)
N1 C17 C1 109.10(16)
N1 C17 C18 111.39(17)
C1 C17 C18 110.3(2)
C12 C13 C8 120.3(3)
O1 C15 N1 122.0(2)
O1 C15 C16 121.3(3)
N1 C15 C16 116.6(3)
C9 C10 C11 120.0(3)
C1 C2 C3 120.5(2)
C12 C11 C10 119.1(3)
C3 C4 C5 119.7(3)
C4 C3 C2 120.2(2)
C19 C18 C17 114.9(2)
C18 C19 C20 112.2(2)
C21 C20 C19 113.3(2)
C11 C12 C13 121.2(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C15 1.225(3)
N1 C15 1.374(4)
N1 C14 1.397(3)
N1 C17 1.486(2)
C6 C5 1.395(4)
C6 C1 1.398(3)
C6 C7 1.477(3)
C7 C14 1.346(4)
C7 C8 1.472(4)
C8 C9 1.395(4)
C8 C13 1.404(3)
C1 C2 1.389(3)
C1 C17 1.510(4)
C5 C4 1.389(3)
C9 C10 1.385(4)
C17 C18 1.539(3)
C13 C12 1.384(4)
C15 C16 1.512(3)
C10 C11 1.394(3)
C2 C3 1.390(4)
C11 C12 1.382(4)
C4 C3 1.375(4)
C18 C19 1.516(4)
C19 C20 1.524(3)
C20 C21 1.511(4)
