#------------------------------------------------------------------------------
#$Date: 2020-01-31 02:17:23 +0200 (Fri, 31 Jan 2020) $
#$Revision: 247388 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/78/4037873.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_4037873
loop_
_publ_author_name
'Zhang, Jin'
'Wang, Xiaogang'
'Chen, Di'
'Kang, Yifan'
'Ma, Yangmin'
'Szostak, Michal'
_publ_section_title
;
 Synthesis of C6-Substituted Isoquinolino[1,2-b]quinazolines via
 Rh(III)-Catalyzed C-H Annulation with Sulfoxonium Ylides.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03065
_journal_year                    2020
_chemical_formula_sum            'C22 H14 N2 O'
_chemical_formula_weight         322.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 93.12(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.2243(8)
_cell_length_b                   10.511(2)
_cell_length_c                   34.796(7)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.08
_cell_measurement_theta_min      3.51
_cell_volume                     1542.7(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2224
_diffrn_reflns_av_unetI/netI     0.2949
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            11262
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.602
_diffrn_reflns_theta_min         2.617
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_description       acicular
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.014(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3499
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.2948
_refine_ls_R_factor_gt           0.1001
_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)+(0.0715P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1626
_refine_ls_wR_factor_ref         0.2176
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1147
_reflns_number_total             3499
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03065_si_002.cif
_cod_data_source_block           SUST_2244_0ma
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037873
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.987
_shelx_estimated_absorpt_t_max   0.990
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
C1 C 0.2272(12) 0.6650(4) 0.35153(14) 0.0426(14) Uani 1 1 d . .
H1 H 0.0933 0.6147 0.3358 0.051 Uiso 1 1 calc R U
C2 C 0.2632(12) 0.7918(4) 0.34313(16) 0.0512(16) Uani 1 1 d . .
H2 H 0.1530 0.8266 0.3218 0.061 Uiso 1 1 calc R U
C3 C 0.4600(13) 0.8679(5) 0.36592(16) 0.0548(16) Uani 1 1 d . .
H3 H 0.4837 0.9536 0.3602 0.066 Uiso 1 1 calc R U
C4 C 0.6218(14) 0.8145(5) 0.39748(17) 0.0601(17) Uani 1 1 d . .
H4 H 0.7546 0.8653 0.4132 0.072 Uiso 1 1 calc R U
C5 C 0.5907(13) 0.6872(5) 0.40621(15) 0.0476(15) Uani 1 1 d . .
H5 H 0.7042 0.6524 0.4273 0.057 Uiso 1 1 calc R U
C6 C 0.3893(12) 0.6117(4) 0.38331(14) 0.0373(13) Uani 1 1 d . .
C7 C 0.3224(11) 0.4802(4) 0.39652(13) 0.0346(13) Uani 1 1 d . .
C8 C 0.2617(11) 0.4595(5) 0.43343(14) 0.0446(14) Uani 1 1 d . .
H8 H 0.3101 0.5236 0.4512 0.053 Uiso 1 1 calc R U
C9 C 0.1252(12) 0.3431(5) 0.44704(14) 0.0391(13) Uani 1 1 d . .
C10 C 0.0642(13) 0.3235(5) 0.48624(15) 0.0513(15) Uani 1 1 d . .
H10 H 0.1302 0.3828 0.5048 0.062 Uiso 1 1 calc R U
C11 C -0.0928(15) 0.2161(6) 0.49637(17) 0.0650(18) Uani 1 1 d . .
H11 H -0.1318 0.2030 0.5221 0.078 Uiso 1 1 calc R U
C12 C -0.1942(15) 0.1276(6) 0.46980(17) 0.0692(19) Uani 1 1 d . .
H12 H -0.3007 0.0552 0.4774 0.083 Uiso 1 1 calc R U
C13 C -0.1368(13) 0.1465(5) 0.43108(15) 0.0540(16) Uani 1 1 d . .
H13 H -0.2102 0.0870 0.4129 0.065 Uiso 1 1 calc R U
C14 C 0.0271(12) 0.2520(5) 0.41925(14) 0.0382(13) Uani 1 1 d . .
C15 C 0.0953(11) 0.2694(4) 0.37925(14) 0.0354(13) Uani 1 1 d . .
C16 C 0.4147(12) 0.3823(5) 0.33384(14) 0.0351(13) Uani 1 1 d . .
C17 C 0.2936(11) 0.2878(4) 0.30593(13) 0.0336(12) Uani 1 1 d . .
C18 C 0.1006(12) 0.1925(4) 0.31794(14) 0.0382(13) Uani 1 1 d . .
C19 C 0.0010(12) 0.0973(4) 0.29144(14) 0.0460(15) Uani 1 1 d . .
H19 H -0.1246 0.0305 0.2993 0.055 Uiso 1 1 calc R U
C20 C 0.0879(13) 0.1024(5) 0.25429(14) 0.0507(16) Uani 1 1 d . .
H20 H 0.0195 0.0396 0.2369 0.061 Uiso 1 1 calc R U
C21 C 0.2783(13) 0.2012(5) 0.24216(15) 0.0508(15) Uani 1 1 d . .
H21 H 0.3340 0.2049 0.2167 0.061 Uiso 1 1 calc R U
C22 C 0.3843(11) 0.2937(5) 0.26800(14) 0.0426(14) Uani 1 1 d . .
H22 H 0.5146 0.3590 0.2602 0.051 Uiso 1 1 calc R U
N1 N 0.2680(9) 0.3785(3) 0.36961(10) 0.0309(10) Uani 1 1 d . .
N2 N 0.0111(9) 0.1802(4) 0.35513(12) 0.0423(12) Uani 1 1 d . .
O1 O 0.6226(8) 0.4599(3) 0.32850(9) 0.0464(10) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 C6 120.4(5)
C3 C2 C1 120.8(5)
C2 C3 C4 118.7(5)
C5 C4 C3 121.3(6)
C4 C5 C6 119.5(5)
C5 C6 C1 119.3(5)
C5 C6 C7 118.4(5)
C1 C6 C7 121.8(5)
C8 C7 N1 118.3(4)
C8 C7 C6 119.7(4)
N1 C7 C6 121.2(4)
C7 C8 C9 123.5(5)
C14 C9 C10 120.0(5)
C14 C9 C8 117.4(5)
C10 C9 C8 122.4(5)
C11 C10 C9 119.1(5)
C12 C11 C10 121.9(6)
C11 C12 C13 119.5(5)
C14 C13 C12 121.2(5)
C13 C14 C9 118.4(5)
C13 C14 C15 121.1(5)
C9 C14 C15 120.5(5)
N2 C15 N1 124.2(4)
N2 C15 C14 118.0(5)
N1 C15 C14 117.7(4)
O1 C16 N1 120.3(5)
O1 C16 C17 125.6(5)
N1 C16 C17 114.2(5)
C18 C17 C22 121.3(5)
C18 C17 C16 119.1(5)
C22 C17 C16 119.6(5)
C17 C18 N2 123.7(4)
C17 C18 C19 118.7(5)
N2 C18 C19 117.5(5)
C20 C19 C18 120.4(5)
C19 C20 C21 120.4(5)
C22 C21 C20 119.9(5)
C21 C22 C17 119.2(5)
C15 N1 C16 119.2(4)
C15 N1 C7 121.2(4)
C16 N1 C7 119.3(4)
C15 N2 C18 117.5(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.375(6)
C1 C6 1.387(6)
C2 C3 1.373(7)
C3 C4 1.381(7)
C4 C5 1.379(6)
C5 C6 1.384(6)
C6 C7 1.489(6)
C7 C8 1.341(6)
C7 N1 1.431(5)
C8 C9 1.443(6)
C9 C14 1.408(6)
C9 C10 1.417(7)
C10 C11 1.365(7)
C11 C12 1.364(7)
C12 C13 1.396(7)
C13 C14 1.382(6)
C14 C15 1.448(6)
C15 N2 1.295(5)
C15 N1 1.409(5)
C16 O1 1.220(5)
C16 N1 1.421(6)
C16 C17 1.462(6)
C17 C18 1.371(6)
C17 C22 1.396(6)
C18 N2 1.374(6)
C18 C19 1.410(6)
C19 C20 1.364(6)
C20 C21 1.392(7)
C21 C22 1.382(6)
