#------------------------------------------------------------------------------
#$Date: 2019-11-25 17:50:24 +0100 (lun 25 de nov de 2019) $
#$Revision: 241560 $
#$URL: svn://www.crystallography.net/cod/cif/4/13/13/4131337.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_4131337
loop_
_publ_author_name
'Chen, Dongping'
'Xu, Guangqing'
'Zhou, Qinghai'
'Chung, Lung Wa'
'Tang, Wenjun'
_publ_section_title
;
 Practical and Asymmetric Reductive Coupling of Isoquinolines Templated by
 Chiral Diborons.
;
_journal_issue                   29
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9767
_journal_page_last               9770
_journal_paper_doi               10.1021/jacs.7b04256
_journal_volume                  139
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H20 N2 O2, C2 O'
_chemical_formula_sum            'C24 H20 N2 O3'
_chemical_formula_weight         384.42
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_Hall           'P 2 2ab'
_space_group_name_H-M_alt        'P 21 21 2'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.5702(10)
_cell_length_b                   6.0644(9)
_cell_length_c                   10.9344(10)
_cell_measurement_reflns_used    7502
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.56
_cell_measurement_theta_min      6.08
_cell_volume                     966.16(18)
_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-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7790
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         66.669
_diffrn_reflns_theta_min         6.074
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_coef       0.056(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         1680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0628P)²+0.2380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1125
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1652
_reflns_number_total             1680
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b04256_si_003.cif
_cod_data_source_block           A
_cod_database_code               4131337
_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.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
C1 C 0.1580(2) 0.4526(6) 0.9034(3) 0.0562(8) Uani 1 1 d . . .
H1A H 0.1676 0.5561 0.9686 0.084 Uiso 1 1 calc R U .
H1B H 0.2162 0.3985 0.8752 0.084 Uiso 1 1 calc R U .
H1C H 0.1216 0.3316 0.9325 0.084 Uiso 1 1 calc R U .
C2 C 0.10914(17) 0.5644(5) 0.8001(2) 0.0426(7) Uani 1 1 d . . .
C3 C 0.12886(17) 0.2274(4) 0.6794(3) 0.0412(6) Uani 1 1 d . . .
H3 H 0.1359 0.1385 0.7480 0.049 Uiso 1 1 calc R U .
C4 C 0.14674(17) 0.1456(4) 0.5690(2) 0.0425(7) Uani 1 1 d . . .
H4 H 0.1627 -0.0022 0.5611 0.051 Uiso 1 1 calc R U .
C5 C 0.14181(16) 0.2832(4) 0.4608(2) 0.0376(6) Uani 1 1 d . . .
C6 C 0.17962(17) 0.2220(5) 0.3478(3) 0.0445(7) Uani 1 1 d . . .
H6 H 0.2076 0.0850 0.3394 0.053 Uiso 1 1 calc R U .
C7 C 0.17573(18) 0.3635(5) 0.2488(2) 0.0462(7) Uani 1 1 d . . .
H7 H 0.2000 0.3203 0.1739 0.055 Uiso 1 1 calc R U .
C8 C 0.13569(17) 0.5693(5) 0.2611(2) 0.0444(7) Uani 1 1 d . . .
H8 H 0.1342 0.6649 0.1946 0.053 Uiso 1 1 calc R U .
C9 C 0.09797(17) 0.6335(4) 0.3714(2) 0.0390(6) Uani 1 1 d . . .
H9 H 0.0713 0.7722 0.3789 0.047 Uiso 1 1 calc R U .
C10 C 0.09975(16) 0.4913(4) 0.4714(2) 0.0355(6) Uani 1 1 d . . .
C11 C 0.05061(15) 0.5443(4) 0.5885(2) 0.0350(6) Uani 1 1 d . . .
H11 H 0.0491 0.7048 0.5986 0.042 Uiso 1 1 calc R U .
C12 C 0.1003(3) 0.9642(7) 0.0291(4) 0.0759(10) Uani 1 1 d . . .
N1 N 0.09929(14) 0.4473(4) 0.69340(19) 0.0372(5) Uani 1 1 d . . .
O1 O 0.07993(14) 0.7525(3) 0.80951(17) 0.0486(6) Uani 1 1 d . . .
O2 O 0.0000 1.0000 0.0833(5) 0.138(2) Uani 1 2 d S T P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
O1 C2 N1 121.2(3) . .
O1 C2 C1 121.7(3) . .
N1 C2 C1 117.2(3) . .
C4 C3 N1 120.7(2) . .
C4 C3 H3 119.7 . .
N1 C3 H3 119.7 . .
C3 C4 C5 121.1(2) . .
C3 C4 H4 119.4 . .
C5 C4 H4 119.4 . .
C6 C5 C10 118.7(2) . .
C6 C5 C4 123.2(2) . .
C10 C5 C4 118.0(2) . .
C7 C6 C5 120.6(3) . .
C7 C6 H6 119.7 . .
C5 C6 H6 119.7 . .
C6 C7 C8 120.1(3) . .
C6 C7 H7 120.0 . .
C8 C7 H7 120.0 . .
C9 C8 C7 120.4(3) . .
C9 C8 H8 119.8 . .
C7 C8 H8 119.8 . .
C8 C9 C10 120.2(2) . .
C8 C9 H9 119.9 . .
C10 C9 H9 119.9 . .
C9 C10 C5 119.9(2) . .
C9 C10 C11 121.9(2) . .
C5 C10 C11 118.0(2) . .
N1 C11 C10 110.44(19) . .
N1 C11 C11 108.42(18) . 2_565
C10 C11 C11 112.00(16) . 2_565
N1 C11 H11 108.6 . .
C10 C11 H11 108.6 . .
C11 C11 H11 108.6 2_565 .
C2 N1 C3 123.3(2) . .
C2 N1 C11 120.4(2) . .
C3 N1 C11 116.2(2) . .
C12 O2 C12 136.3(5) . 2_575
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.497(4) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 O1 1.222(4) .
C2 N1 1.374(4) .
C3 C4 1.331(4) .
C3 N1 1.410(3) .
C3 H3 0.9300 .
C4 C5 1.449(4) .
C4 H4 0.9300 .
C5 C6 1.402(4) .
C5 C10 1.408(4) .
C6 C7 1.383(4) .
C6 H6 0.9300 .
C7 C8 1.384(4) .
C7 H7 0.9300 .
C8 C9 1.381(4) .
C8 H8 0.9300 .
C9 C10 1.393(3) .
C9 H9 0.9300 .
C10 C11 1.502(3) .
C11 N1 1.471(3) .
C11 C11 1.570(4) 2_565
C11 H11 0.9800 .
C12 O2 1.591(5) .
O2 C12 1.592(5) 2_575
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_4
N1 C3 C4 C5 3.8(4) . .
C3 C4 C5 C6 164.8(3) . .
C3 C4 C5 C10 -12.9(4) . .
C10 C5 C6 C7 0.1(4) . .
C4 C5 C6 C7 -177.6(2) . .
C5 C6 C7 C8 1.1(4) . .
C6 C7 C8 C9 -1.1(4) . .
C7 C8 C9 C10 -0.1(4) . .
C8 C9 C10 C5 1.3(4) . .
C8 C9 C10 C11 -173.2(2) . .
C6 C5 C10 C9 -1.3(3) . .
C4 C5 C10 C9 176.5(2) . .
C6 C5 C10 C11 173.4(2) . .
C4 C5 C10 C11 -8.8(3) . .
C9 C10 C11 N1 -149.3(2) . .
C5 C10 C11 N1 36.1(3) . .
C9 C10 C11 C11 89.8(3) . 2_565
C5 C10 C11 C11 -84.8(3) . 2_565
O1 C2 N1 C3 -177.7(2) . .
C1 C2 N1 C3 3.0(3) . .
O1 C2 N1 C11 -1.8(4) . .
C1 C2 N1 C11 178.9(2) . .
C4 C3 N1 C2 -157.2(3) . .
C4 C3 N1 C11 26.8(3) . .
C10 C11 N1 C2 138.8(2) . .
C11 C11 N1 C2 -98.1(3) 2_565 .
C10 C11 N1 C3 -45.0(3) . .
C11 C11 N1 C3 78.1(3) 2_565 .
