#------------------------------------------------------------------------------
#$Date: 2015-09-14 10:49:49 +0300 (Mon, 14 Sep 2015) $
#$Revision: 156297 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/77/7117777.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_7117777
loop_
_publ_author_name
'Bole Yu'
'Ying Chen'
'Mei Hong'
'Pingping Duan'
'Shifeng Gan'
'Hui Chao'
'Zujin Zhao'
'Jing Zhao'
_publ_section_title
;
 Rhodium-catalyzed C-H activation of hydrazines leads to isoquinolones
 with tunable aggregation-induced emission properties
;
_journal_name_full               Chem.Commun.
_journal_page_first              14365
_journal_paper_doi               10.1039/C5cc05239D
_journal_volume                  51
_journal_year                    2015
_chemical_formula_sum            'C18 H15 N O'
_chemical_formula_weight         261.31
_chemical_name_systematic
;
 ?
;
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2015-03-20 deposited with the CCDC.
2015-08-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.877(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.7421(2)
_cell_length_b                   7.51390(10)
_cell_length_c                   14.7733(10)
_cell_measurement_reflns_used    15169
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      6.70
_cell_volume                     1353.52(11)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_laue_measured_fraction_full 0.987
_diffrn_reflns_laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17762
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.270
_diffrn_reflns_theta_min         6.672
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2435
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0468
_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)+(0.0757P)²+0.0789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1303
_reflns_Friedel_coverage         0.000
_reflns_friedel_fraction_full    .
_reflns_friedel_fraction_max     .
_reflns_number_gt                1980
_reflns_number_total             2435
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5cc05239d2.cif
_cod_data_source_block           shelx
_cod_database_code               7117777
_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+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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.09671(7) 0.04637(16) 0.05479(6) 0.0658(3) Uani 1 1 d . . . . .
N1 N 0.08490(9) 0.07571(16) 0.12718(8) 0.0499(3) Uani 1 1 d D . . . .
H1N H 0.0950(12) 0.053(2) 0.0732(10) 0.060 Uiso 1 1 d D U . . .
C1 C 0.47518(13) 0.1259(3) 0.13033(13) 0.0763(5) Uani 1 1 d . . . . .
H1 H 0.5400 0.1329 0.1135 0.092 Uiso 1 1 calc R U . . .
C2 C 0.39859(12) -0.0016(2) 0.09055(11) 0.0675(4) Uani 1 1 d . . . . .
H2 H 0.4116 -0.0812 0.0468 0.081 Uiso 1 1 calc R U . . .
C3 C 0.30196(11) -0.0120(2) 0.11535(9) 0.0547(4) Uani 1 1 d . . . . .
H3 H 0.2503 -0.0983 0.0877 0.066 Uiso 1 1 calc R U . . .
C4 C 0.28136(10) 0.10530(18) 0.18120(9) 0.0495(3) Uani 1 1 d . . . . .
C5 C 0.17618(10) 0.09757(17) 0.20557(9) 0.0456(3) Uani 1 1 d . . . . .
C6 C 0.16277(10) 0.11145(17) 0.29326(9) 0.0457(3) Uani 1 1 d . . . . .
C7 C 0.05206(10) 0.11026(16) 0.30172(9) 0.0446(3) Uani 1 1 d . . . . .
C8 C -0.03823(10) 0.08939(16) 0.22105(9) 0.0455(3) Uani 1 1 d . . . . .
C9 C -0.14532(11) 0.0871(2) 0.22814(11) 0.0550(4) Uani 1 1 d . . . . .
H9 H -0.2041 0.0728 0.1740 0.066 Uiso 1 1 calc R U . . .
C10 C -0.16407(13) 0.1058(2) 0.31410(12) 0.0627(4) Uani 1 1 d . . . . .
H10 H -0.2353 0.1033 0.3188 0.075 Uiso 1 1 calc R U . . .
C11 C -0.02090(10) 0.06871(18) 0.12874(9) 0.0489(3) Uani 1 1 d . . . . .
C12 C 0.25581(11) 0.1266(2) 0.38196(9) 0.0573(4) Uani 1 1 d . . . . .
H12 H 0.2700 0.2472 0.4078 0.069 Uiso 1 1 calc R U . . .
C13 C 0.27642(13) -0.0191(3) 0.45451(11) 0.0733(5) Uani 1 1 d . . . . .
H13A H 0.2991 0.0151 0.5207 0.088 Uiso 1 1 calc R U . . .
H13B H 0.2301 -0.1239 0.4401 0.088 Uiso 1 1 calc R U . . .
C14 C 0.35492(13) 0.0109(3) 0.39890(12) 0.0798(5) Uani 1 1 d . . . . .
H14A H 0.3565 -0.0759 0.3507 0.096 Uiso 1 1 calc R U . . .
H14B H 0.4255 0.0630 0.4313 0.096 Uiso 1 1 calc R U . . .
C15 C 0.02964(12) 0.13000(18) 0.38913(10) 0.0556(4) Uani 1 1 d . . . . .
H15 H 0.0874 0.1442 0.4441 0.067 Uiso 1 1 calc R U . . .
C16 C -0.07588(13) 0.1286(2) 0.39439(11) 0.0631(4) Uani 1 1 d . . . . .
H16 H -0.0887 0.1431 0.4528 0.076 Uiso 1 1 calc R U . . .
C17 C 0.35985(11) 0.2338(2) 0.22057(11) 0.0625(4) Uani 1 1 d . . . . .
H17 H 0.3476 0.3140 0.2644 0.075 Uiso 1 1 calc R U . . .
C18 C 0.45590(13) 0.2433(3) 0.19514(12) 0.0765(5) Uani 1 1 d . . . . .
H18 H 0.5079 0.3297 0.2221 0.092 Uiso 1 1 calc R U . . .
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
C11 N1 C5 125.81(12) . .
C11 N1 H1N 115.2(10) . .
C5 N1 H1N 118.7(10) . .
C2 C1 C18 119.82(14) . .
C2 C1 H1 120.1 . .
C18 C1 H1 120.1 . .
C1 C2 C3 120.18(15) . .
C1 C2 H2 119.9 . .
C3 C2 H2 119.9 . .
C2 C3 C4 120.75(13) . .
C2 C3 H3 119.6 . .
C4 C3 H3 119.6 . .
C17 C4 C3 118.23(12) . .
C17 C4 C5 121.03(12) . .
C3 C4 C5 120.69(11) . .
C6 C5 N1 119.73(12) . .
C6 C5 C4 126.85(11) . .
N1 C5 C4 113.42(11) . .
C5 C6 C7 118.42(12) . .
C5 C6 C12 123.67(12) . .
C7 C6 C12 117.92(11) . .
C8 C7 C15 117.09(12) . .
C8 C7 C6 120.31(12) . .
C15 C7 C6 122.61(12) . .
C9 C8 C7 120.96(12) . .
C9 C8 C11 119.13(12) . .
C7 C8 C11 119.90(11) . .
C10 C9 C8 120.41(14) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
C9 C10 C16 119.38(13) . .
C9 C10 H10 120.3 . .
C16 C10 H10 120.3 . .
O1 C11 N1 120.90(12) . .
O1 C11 C8 123.32(12) . .
N1 C11 C8 115.78(12) . .
C14 C12 C6 121.32(13) . .
C14 C12 C13 59.44(11) . .
C6 C12 C13 120.04(13) . .
C14 C12 H12 114.9 . .
C6 C12 H12 114.9 . .
C13 C12 H12 114.9 . .
C14 C13 C12 60.03(11) . .
C14 C13 H13A 117.8 . .
C12 C13 H13A 117.8 . .
C14 C13 H13B 117.8 . .
C12 C13 H13B 117.8 . .
H13A C13 H13B 114.9 . .
C13 C14 C12 60.53(11) . .
C13 C14 H14A 117.7 . .
C12 C14 H14A 117.7 . .
C13 C14 H14B 117.7 . .
C12 C14 H14B 117.7 . .
H14A C14 H14B 114.8 . .
C16 C15 C7 121.00(14) . .
C16 C15 H15 119.5 . .
C7 C15 H15 119.5 . .
C15 C16 C10 121.16(13) . .
C15 C16 H16 119.4 . .
C10 C16 H16 119.4 . .
C18 C17 C4 120.55(14) . .
C18 C17 H17 119.7 . .
C4 C17 H17 119.7 . .
C1 C18 C17 120.48(15) . .
C1 C18 H18 119.8 . .
C17 C18 H18 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C11 1.2418(16) .
N1 C11 1.3559(17) .
N1 C5 1.3924(16) .
N1 H1N 0.861(14) .
C1 C2 1.372(2) .
C1 C18 1.375(3) .
C1 H1 0.9300 .
C2 C3 1.3850(19) .
C2 H2 0.9300 .
C3 C4 1.393(2) .
C3 H3 0.9300 .
C4 C17 1.3904(19) .
C4 C5 1.4863(17) .
C5 C6 1.3591(19) .
C6 C7 1.4519(18) .
C6 C12 1.4945(18) .
C7 C8 1.4045(18) .
C7 C15 1.4090(19) .
C8 C9 1.3986(18) .
C8 C11 1.4517(18) .
C9 C10 1.366(2) .
C9 H9 0.9300 .
C10 C16 1.387(2) .
C10 H10 0.9300 .
C12 C14 1.493(2) .
C12 C13 1.501(2) .
C12 H12 0.9800 .
C13 C14 1.484(2) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C15 C16 1.369(2) .
C15 H15 0.9300 .
C16 H16 0.9300 .
C17 C18 1.382(2) .
C17 H17 0.9300 .
C18 H18 0.9300 .
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
N1 H1N O1 0.861(14) 2.039(14) 2.8855(15) 167.5(15) 3
