#------------------------------------------------------------------------------
#$Date: 2019-11-24 15:08:59 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238285 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/50/1555037.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_1555037
loop_
_publ_author_name
'Son, Jeong-Yu'
'Kim, Sunghwa'
'Jeon, Woo Hyung'
'Lee, Phil Ho'
_publ_section_title
;
 Synthesis of Cinnolin-3(2H)-one Derivatives from Rh-Catalyzed Reaction of
 Azobenzenes with Diazotized Meldrum's Acid.
;
_journal_issue                   10
_journal_name_full               'Organic letters'
_journal_page_first              2518
_journal_page_last               2521
_journal_paper_doi               10.1021/acs.orglett.5b01052
_journal_volume                  17
_journal_year                    2015
_chemical_formula_sum            'C17 H14 N2 O3'
_chemical_formula_weight         294.30
_chemical_name_common            SJY-002
_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
_cell_angle_alpha                90
_cell_angle_beta                 103.0642(12)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9224(2)
_cell_length_b                   9.3813(2)
_cell_length_c                   18.2533(4)
_cell_measurement_reflns_used    8905
_cell_measurement_temperature    296.(2)
_cell_measurement_theta_max      27.9070
_cell_measurement_theta_min      2.2908
_cell_volume                     1488.32(6)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            34659
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.212
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3705
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0572
_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)+(0.0425P)²+0.5528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1245
_reflns_number_gt                2589
_reflns_number_total             3705
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol5b01052_si_001.cif
_cod_data_source_block           I
_cod_database_code               1555037
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
C C1 0.20203(18) 0.46848(16) 0.03339(9) 0.0369(4) Uani d . . 1
C C2 0.1966(2) 0.61470(18) 0.01045(11) 0.0476(5) Uani d . . 1
H H2 0.2159 0.6392 -0.0359 0.057 Uiso calc U R 1
C C3 0.1634(2) 0.71633(19) 0.05601(12) 0.0552(5) Uani d . . 1
H H3 0.1581 0.8111 0.0407 0.066 Uiso calc U R 1
C C4 0.1364(2) 0.6806(2) 0.12721(13) 0.0564(5) Uani d . . 1
H H4 0.1145 0.753 0.158 0.068 Uiso calc U R 1
C C5 0.1413(2) 0.54499(19) 0.15179(11) 0.0485(5) Uani d . . 1
H H5 0.1247 0.5252 0.1993 0.058 Uiso calc U R 1
C C6 0.17217(18) 0.43069(17) 0.10491(9) 0.0369(4) Uani d . . 1
C C7 0.17703(18) 0.28826(17) 0.12328(9) 0.0363(4) Uani d . . 1
C C8 0.19452(18) 0.18112(17) 0.06975(9) 0.0349(4) Uani d . . 1
C C9 0.1565(2) 0.23430(19) 0.19748(10) 0.0430(4) Uani d . . 1
C C10 0.2575(3) 0.0729(3) 0.29585(12) 0.0694(6) Uani d . . 1
H H10A 0.1684 0.0108 0.2847 0.083 Uiso calc U R 1
H H10B 0.2455 0.1394 0.3348 0.083 Uiso calc U R 1
C C11 0.3993(4) -0.0116(4) 0.32101(17) 0.1131(12) Uani d . . 1
H H11A 0.4065 -0.081 0.2833 0.17 Uiso calc U R 1
H H11B 0.3965 -0.0592 0.3672 0.17 Uiso calc U R 1
H H11C 0.487 0.0504 0.3288 0.17 Uiso calc U R 1
C C12 0.28526(19) 0.13964(16) -0.04702(9) 0.0357(4) Uani d . . 1
C C13 0.4281(2) 0.1618(2) -0.06143(11) 0.0482(5) Uani d . . 1
H H13 0.4902 0.2357 -0.0378 0.058 Uiso calc U R 1
C C14 0.4785(2) 0.0732(2) -0.11139(12) 0.0574(5) Uani d . . 1
H H14 0.5745 0.0879 -0.1219 0.069 Uiso calc U R 1
C C15 0.3876(3) -0.0362(2) -0.14537(12) 0.0580(5) Uani d . . 1
H H15 0.4223 -0.0965 -0.1784 0.07 Uiso calc U R 1
C C16 0.2450(2) -0.0571(2) -0.13069(11) 0.0560(5) Uani d . . 1
H H16 0.1835 -0.1315 -0.1541 0.067 Uiso calc U R 1
C C17 0.1915(2) 0.03118(18) -0.08141(10) 0.0435(4) Uani d . . 1
H H17 0.0945 0.0175 -0.0718 0.052 Uiso calc U R 1
N N1 0.23787(16) 0.37371(14) -0.01385(8) 0.0385(3) Uani d . . 1
N N2 0.23523(15) 0.23565(13) 0.00486(7) 0.0352(3) Uani d . . 1
O O1 0.04965(16) 0.26322(16) 0.22435(8) 0.0621(4) Uani d . . 1
O O2 0.27202(15) 0.14967(15) 0.22872(7) 0.0566(4) Uani d . . 1
O O3 0.17673(14) 0.05303(11) 0.07635(7) 0.0465(3) Uani d . . 1
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
N1 C1 C2 116.69(16)
N1 C1 C6 123.18(14)
C2 C1 C6 120.12(15)
C3 C2 C1 119.82(18)
C2 C3 C4 120.57(17)
C5 C4 C3 122.04(18)
C4 C5 C6 120.19(18)
C7 C6 C1 117.37(14)
C7 C6 C5 125.40(16)
C1 C6 C5 117.23(15)
C6 C7 C8 121.10(15)
C6 C7 C9 123.09(15)
C8 C7 C9 115.73(14)
O3 C8 N2 120.22(14)
O3 C8 C7 125.83(15)
N2 C8 C7 113.95(13)
O1 C9 O2 125.01(17)
O1 C9 C7 124.47(18)
O2 C9 C7 110.51(14)
O2 C10 C11 107.20(18)
C13 C12 C17 121.31(16)
C13 C12 N2 117.84(15)
C17 C12 N2 120.84(14)
C12 C13 C14 119.26(17)
C15 C14 C13 120.20(18)
C14 C15 C16 120.02(18)
C15 C16 C17 120.81(18)
C12 C17 C16 118.39(17)
C1 N1 N2 117.44(13)
N1 N2 C8 125.92(13)
N1 N2 C12 114.10(12)
C8 N2 C12 119.94(12)
C9 O2 C10 116.86(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 N1 1.327(2)
C1 C2 1.432(2)
C1 C6 1.435(2)
C2 C3 1.342(3)
C3 C4 1.414(3)
C4 C5 1.347(3)
C5 C6 1.437(2)
C6 C7 1.376(2)
C7 C8 1.435(2)
C7 C9 1.495(2)
C8 O3 1.2217(18)
C8 N2 1.411(2)
C9 O1 1.198(2)
C9 O2 1.324(2)
C10 O2 1.452(2)
C10 C11 1.475(3)
C12 C13 1.375(2)
C12 C17 1.375(2)
C12 N2 1.449(2)
C13 C14 1.382(3)
C14 C15 1.367(3)
C15 C16 1.372(3)
C16 C17 1.385(2)
N1 N2 1.3410(18)
