#------------------------------------------------------------------------------
#$Date: 2020-05-05 16:51:13 +0300 (Tue, 05 May 2020) $
#$Revision: 251734 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157417.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_7157417
loop_
_publ_author_name
'Ning, Yi'
'He, Xinwei'
'Zuo, Youpeng'
'Wang, Jian'
'Tang, Qiang'
'Xie, Mengqing'
'Li, Ruxue'
'Shang, Yongjia'
_publ_section_title
;
 Rh-Catalyzed C-H activation/intramolecular condensation for the
 construction of benzo[f]pyrazolo[1,5-a][1,3]diazepines.
;
_journal_issue                   15
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2893
_journal_page_last               2901
_journal_paper_doi               10.1039/d0ob00382d
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C18 H19 N3 O'
_chemical_formula_weight         293.36
_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-2018/1
_audit_update_record
;
2020-01-11 deposited with the CCDC.	2020-03-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.667(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2409(13)
_cell_length_b                   19.433(4)
_cell_length_c                   10.923(2)
_cell_measurement_reflns_used    5559
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.24
_cell_measurement_theta_min      2.81
_cell_volume                     1529.5(5)
_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-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0408
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14727
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.369
_diffrn_reflns_theta_min         2.096
_exptl_absorpt_coefficient_mu    0.081
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2800
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0462
_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)+(0.0630P)²+0.4168P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1269
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2181
_reflns_number_total             2800
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00382d2.cif
_cod_data_source_block           mp_a
_cod_depositor_comments
'Adding full bibliography for 7157416--7157417.cif.'
_cod_original_cell_volume        1529.4(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7157417
_shelx_shelxl_version_number     2018/1
_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   0.982
_shelx_estimated_absorpt_t_max   0.984
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
C1 C 0.4168(2) 0.58338(9) 0.78751(16) 0.0315(4) Uani 1 1 d . . . . .
C2 C 0.3547(3) 0.55030(10) 0.88887(18) 0.0410(5) Uani 1 1 d . . . . .
H2 H 0.414322 0.557973 0.967060 0.049 Uiso 1 1 calc R U . . .
C3 C 0.2058(3) 0.50640(11) 0.8735(2) 0.0513(6) Uani 1 1 d . . . . .
H3 H 0.161176 0.485740 0.941537 0.062 Uiso 1 1 calc R U . . .
C4 C 0.1226(3) 0.49303(12) 0.7570(2) 0.0527(6) Uani 1 1 d . . . . .
H4 H 0.027713 0.460708 0.745501 0.063 Uiso 1 1 calc R U . . .
C5 C 0.1803(2) 0.52765(10) 0.65758(19) 0.0434(5) Uani 1 1 d . . . . .
H5 H 0.121456 0.518848 0.579583 0.052 Uiso 1 1 calc R U . . .
C6 C 0.3249(2) 0.57572(9) 0.67046(16) 0.0316(4) Uani 1 1 d . . . . .
C7 C 0.3674(2) 0.61573(9) 0.56021(16) 0.0306(4) Uani 1 1 d . . . . .
C8 C 0.2127(2) 0.64440(10) 0.48086(16) 0.0353(4) Uani 1 1 d . . . . .
C9 C 0.2543(2) 0.68458(10) 0.36917(17) 0.0407(5) Uani 1 1 d . . . . .
H9A H 0.279561 0.732011 0.392911 0.049 Uiso 1 1 calc R U . . .
H9B H 0.145482 0.684224 0.309791 0.049 Uiso 1 1 calc R U . . .
C10 C 0.4188(2) 0.65636(10) 0.30824(16) 0.0351(4) Uani 1 1 d . . . . .
C11 C 0.5835(2) 0.65569(10) 0.40689(16) 0.0376(4) Uani 1 1 d . . . . .
H11A H 0.683013 0.629206 0.376626 0.045 Uiso 1 1 calc R U . . .
H11B H 0.627680 0.702497 0.419890 0.045 Uiso 1 1 calc R U . . .
C12 C 0.5423(2) 0.62640(9) 0.52796(16) 0.0312(4) Uani 1 1 d . . . . .
C13 C 0.7204(2) 0.62811(9) 0.72998(16) 0.0328(4) Uani 1 1 d . . . . .
C14 C 0.8737(2) 0.65274(11) 0.79804(18) 0.0417(5) Uani 1 1 d . . . . .
H14 H 0.988954 0.662182 0.771147 0.050 Uiso 1 1 calc R U . . .
C15 C 0.8211(3) 0.66086(10) 0.91730(18) 0.0418(5) Uani 1 1 d . . . . .
C16 C 0.3774(3) 0.58414(11) 0.25831(19) 0.0477(5) Uani 1 1 d . . . . .
H16A H 0.482192 0.567345 0.219879 0.072 Uiso 1 1 calc R U . . .
H16B H 0.270486 0.585509 0.198917 0.072 Uiso 1 1 calc R U . . .
H16C H 0.353403 0.554107 0.324701 0.072 Uiso 1 1 calc R U . . .
C17 C 0.4614(3) 0.70320(13) 0.20240(19) 0.0551(6) Uani 1 1 d . . . . .
H17A H 0.488126 0.748768 0.233197 0.083 Uiso 1 1 calc R U . . .
H17B H 0.356053 0.704655 0.141795 0.083 Uiso 1 1 calc R U . . .
H17C H 0.566942 0.685645 0.165665 0.083 Uiso 1 1 calc R U . . .
C18 C 0.9372(3) 0.68534(14) 1.0294(2) 0.0637(7) Uani 1 1 d . . . . .
H18A H 0.957272 0.733996 1.023240 0.096 Uiso 1 1 calc R U . . .
H18B H 1.054522 0.661921 1.036025 0.096 Uiso 1 1 calc R U . . .
H18C H 0.874527 0.675837 1.100969 0.096 Uiso 1 1 calc R U . . .
N1 N 0.58234(19) 0.62302(8) 0.80569(13) 0.0344(4) Uani 1 1 d . . . . .
N2 N 0.6459(2) 0.64305(9) 0.92369(14) 0.0423(4) Uani 1 1 d . . . . .
N3 N 0.69942(19) 0.61192(8) 0.60559(14) 0.0393(4) Uani 1 1 d . . . . .
H3A H 0.789955 0.591626 0.575068 0.047 Uiso 1 1 calc R U . . .
O1 O 0.05050(17) 0.63938(9) 0.50405(13) 0.0554(4) 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 121.28(16) . . ?
C6 C1 N1 120.46(15) . . ?
C2 C1 N1 118.20(16) . . ?
C3 C2 C1 120.07(19) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 119.78(18) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.81(19) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 121.95(19) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C1 C6 C5 116.70(16) . . ?
C1 C6 C7 124.68(15) . . ?
C5 C6 C7 118.61(16) . . ?
C12 C7 C8 117.83(16) . . ?
C12 C7 C6 123.99(15) . . ?
C8 C7 C6 118.17(14) . . ?
O1 C8 C7 122.73(16) . . ?
O1 C8 C9 118.71(16) . . ?
C7 C8 C9 118.50(14) . . ?
C8 C9 C10 113.31(15) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C16 110.67(15) . . ?
C9 C10 C11 106.54(14) . . ?
C16 C10 C11 110.92(16) . . ?
C9 C10 C17 109.98(16) . . ?
C16 C10 C17 108.98(16) . . ?
C11 C10 C17 109.72(15) . . ?
C12 C11 C10 114.66(14) . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C7 C12 N3 122.76(16) . . ?
C7 C12 C11 123.88(16) . . ?
N3 C12 C11 113.36(14) . . ?
C14 C13 N1 107.57(16) . . ?
C14 C13 N3 128.25(16) . . ?
N1 C13 N3 124.17(15) . . ?
C13 C14 C15 105.40(16) . . ?
C13 C14 H14 127.3 . . ?
C15 C14 H14 127.3 . . ?
N2 C15 C14 111.68(16) . . ?
N2 C15 C18 120.35(18) . . ?
C14 C15 C18 127.97(18) . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 N1 N2 110.43(14) . . ?
C13 N1 C1 127.84(15) . . ?
N2 N1 C1 118.79(14) . . ?
C15 N2 N1 104.91(15) . . ?
C12 N3 C13 124.01(14) . . ?
C12 N3 H3A 118.0 . . ?
C13 N3 H3A 118.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.390(2) . ?
C1 C2 1.392(2) . ?
C1 N1 1.422(2) . ?
C2 C3 1.372(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.491(2) . ?
C7 C12 1.364(2) . ?
C7 C8 1.457(2) . ?
C8 O1 1.230(2) . ?
C8 C9 1.504(3) . ?
C9 C10 1.523(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C16 1.525(3) . ?
C10 C11 1.526(2) . ?
C10 C17 1.527(3) . ?
C11 C12 1.497(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N3 1.379(2) . ?
C13 C14 1.361(3) . ?
C13 N1 1.362(2) . ?
C13 N3 1.388(2) . ?
C14 C15 1.402(3) . ?
C14 H14 0.9300 . ?
C15 N2 1.323(2) . ?
C15 C18 1.493(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 N2 1.381(2) . ?
N3 H3A 0.8600 . ?
