#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:40:54 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281571 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/90/7159060.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_7159060
loop_
_publ_author_name
'Chen, Wenxi'
'Mao, Yan'
'Wang, Min'
'Ling, Fei'
'Li, Changchang'
'Chen, Zhangpei'
'Yao, Jinzhong'
_publ_section_title
;
 Rh(III)-catalyzed [4 + 1] cyclization of aryl substituted pyrazoles with
 cyclopropanols via C-H activation.
;
_journal_issue                   4
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              775
_journal_page_last               782
_journal_paper_doi               10.1039/d2ob02001g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C19 H15 Br N2 O'
_chemical_formula_weight         367.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-11-01 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                100.097(6)
_cell_angle_beta                 96.581(6)
_cell_angle_gamma                96.739(6)
_cell_formula_units_Z            2
_cell_length_a                   5.537(3)
_cell_length_b                   11.122(5)
_cell_length_c                   13.317(6)
_cell_measurement_reflns_used    2220
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.64
_cell_measurement_theta_min      2.20
_cell_volume                     794.1(7)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.986
_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  0.0305
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7463
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.205
_exptl_absorpt_coefficient_mu    2.594
_exptl_absorpt_correction_T_max  0.856
_exptl_absorpt_correction_T_min  0.674
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3591
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0300P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0752
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2673
_reflns_number_total             3591
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob02001g2.cif
_cod_data_source_block           0811Y_0m
_cod_depositor_comments          'Adding full bibliography for 7159060.cif.'
_cod_database_code               7159060
_shelx_shelxl_version_number     2016/6
_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   0.652
_shelx_estimated_absorpt_t_max   0.860
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.85012(5) 0.57478(2) 0.63186(2) 0.05177(11) Uani 1 1 d . . . . .
O1 O 0.8123(3) 0.56719(16) 0.23338(13) 0.0530(5) Uani 1 1 d . . . . .
N1 N 0.3842(4) 0.85511(18) 0.29294(15) 0.0451(5) Uani 1 1 d . . . . .
N2 N 0.3037(4) 0.91475(19) 0.21803(16) 0.0512(5) Uani 1 1 d . . . . .
C1 C 0.0208(6) 1.0683(3) 0.2054(2) 0.0719(9) Uani 1 1 d . . . . .
H1A H 0.058924 1.057483 0.136099 0.108 Uiso 1 1 calc R U . . .
H1B H 0.075075 1.152156 0.239616 0.108 Uiso 1 1 calc R U . . .
H1C H -0.153437 1.049747 0.204096 0.108 Uiso 1 1 calc R U . . .
C2 C 0.1485(5) 0.9832(2) 0.2621(2) 0.0519(7) Uani 1 1 d . . . . .
C3 C 0.1285(5) 0.9643(3) 0.3619(2) 0.0615(8) Uani 1 1 d . . . . .
H3 H 0.029855 1.000683 0.407049 0.074 Uiso 1 1 calc R U . . .
C4 C 0.2841(4) 0.8811(2) 0.37951(19) 0.0451(6) Uani 1 1 d . . . . .
C5 C 0.3895(4) 0.8096(2) 0.45142(18) 0.0423(6) Uani 1 1 d . . . . .
C6 C 0.3548(5) 0.8034(3) 0.5516(2) 0.0615(8) Uani 1 1 d . . . . .
H6 H 0.242394 0.847350 0.583310 0.074 Uiso 1 1 calc R U . . .
C7 C 0.4897(5) 0.7307(3) 0.6041(2) 0.0542(7) Uani 1 1 d . . . . .
H7 H 0.466914 0.724480 0.671241 0.065 Uiso 1 1 calc R U . . .
C8 C 0.6575(4) 0.6680(2) 0.55611(18) 0.0403(6) Uani 1 1 d . . . . .
C9 C 0.6933(4) 0.6716(2) 0.45520(18) 0.0411(6) Uani 1 1 d . . . . .
H9 H 0.807698 0.628377 0.424128 0.049 Uiso 1 1 calc R U . . .
C10 C 0.5533(4) 0.7416(2) 0.40245(17) 0.0376(5) Uani 1 1 d . . . . .
C11 C 0.5483(4) 0.7595(2) 0.29098(17) 0.0410(6) Uani 1 1 d . . . . .
H11 H 0.711998 0.790787 0.277476 0.049 Uiso 1 1 calc R U . . .
C12 C 0.4333(4) 0.6464(2) 0.21062(17) 0.0413(6) Uani 1 1 d . . . . .
H12A H 0.283947 0.610747 0.232171 0.050 Uiso 1 1 calc R U . . .
H12B H 0.388019 0.672260 0.145954 0.050 Uiso 1 1 calc R U . . .
C13 C 0.5990(4) 0.5485(2) 0.19292(17) 0.0401(6) Uani 1 1 d . . . . .
C14 C 0.4970(4) 0.4282(2) 0.12363(16) 0.0391(5) Uani 1 1 d . . . . .
C15 C 0.6378(5) 0.3334(2) 0.11660(19) 0.0519(7) Uani 1 1 d . . . . .
H15 H 0.790554 0.344394 0.156734 0.062 Uiso 1 1 calc R U . . .
C16 C 0.5541(6) 0.2227(3) 0.0506(2) 0.0678(8) Uani 1 1 d . . . . .
H16 H 0.650206 0.159287 0.046602 0.081 Uiso 1 1 calc R U . . .
C17 C 0.3290(6) 0.2056(3) -0.0092(2) 0.0654(8) Uani 1 1 d . . . . .
H17 H 0.273143 0.130986 -0.054133 0.078 Uiso 1 1 calc R U . . .
C18 C 0.1882(5) 0.2983(3) -0.0026(2) 0.0636(8) Uani 1 1 d . . . . .
H18 H 0.036083 0.286694 -0.043200 0.076 Uiso 1 1 calc R U . . .
C19 C 0.2688(4) 0.4091(3) 0.06382(19) 0.0520(7) Uani 1 1 d . . . . .
H19 H 0.169770 0.471284 0.068544 0.062 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 0.0033 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'
Br Br -0.2901 2.4595 '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
C4 N1 N2 114.1(2) . . ?
C4 N1 C11 115.40(19) . . ?
N2 N1 C11 130.3(2) . . ?
C2 N2 N1 103.0(2) . . ?
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 . . ?
N2 C2 C3 111.6(2) . . ?
N2 C2 C1 120.7(2) . . ?
C3 C2 C1 127.6(3) . . ?
C4 C3 C2 105.7(2) . . ?
C4 C3 H3 127.2 . . ?
C2 C3 H3 127.2 . . ?
N1 C4 C3 105.5(2) . . ?
N1 C4 C5 107.1(2) . . ?
C3 C4 C5 147.4(3) . . ?
C6 C5 C10 120.7(2) . . ?
C6 C5 C4 131.5(2) . . ?
C10 C5 C4 107.8(2) . . ?
C5 C6 C7 119.2(2) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C8 C7 C6 119.4(2) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 122.5(2) . . ?
C7 C8 Br1 118.53(18) . . ?
C9 C8 Br1 118.96(19) . . ?
C10 C9 C8 117.7(2) . . ?
C10 C9 H9 121.1 . . ?
C8 C9 H9 121.1 . . ?
C9 C10 C5 120.4(2) . . ?
C9 C10 C11 129.1(2) . . ?
C5 C10 C11 110.50(19) . . ?
N1 C11 C12 109.37(18) . . ?
N1 C11 C10 98.77(18) . . ?
C12 C11 C10 114.50(19) . . ?
N1 C11 H11 111.2 . . ?
C12 C11 H11 111.2 . . ?
C10 C11 H11 111.2 . . ?
C13 C12 C11 113.87(18) . . ?
C13 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
O1 C13 C14 120.5(2) . . ?
O1 C13 C12 121.0(2) . . ?
C14 C13 C12 118.57(19) . . ?
C15 C14 C19 118.6(2) . . ?
C15 C14 C13 118.8(2) . . ?
C19 C14 C13 122.6(2) . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 119.7(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.7(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C14 120.3(3) . . ?
C18 C19 H19 119.9 . . ?
C14 C19 H19 119.9 . . ?
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
Br1 C8 1.900(2) . ?
O1 C13 1.219(3) . ?
N1 C4 1.337(3) . ?
N1 N2 1.354(3) . ?
N1 C11 1.476(3) . ?
N2 C2 1.332(3) . ?
C1 C2 1.500(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.397(4) . ?
C3 C4 1.367(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.462(3) . ?
C5 C6 1.381(3) . ?
C5 C10 1.394(3) . ?
C6 C7 1.386(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.375(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.387(3) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.529(3) . ?
C11 C12 1.522(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.509(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.494(3) . ?
C14 C15 1.380(3) . ?
C14 C19 1.387(3) . ?
C15 C16 1.377(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.375(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.360(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 N2 C2 1.2(3) . . . . ?
C11 N1 N2 C2 175.7(2) . . . . ?
N1 N2 C2 C3 -1.4(3) . . . . ?
N1 N2 C2 C1 178.2(2) . . . . ?
N2 C2 C3 C4 1.1(3) . . . . ?
C1 C2 C3 C4 -178.5(3) . . . . ?
N2 N1 C4 C3 -0.6(3) . . . . ?
C11 N1 C4 C3 -175.9(2) . . . . ?
N2 N1 C4 C5 179.86(19) . . . . ?
C11 N1 C4 C5 4.5(3) . . . . ?
C2 C3 C4 N1 -0.3(3) . . . . ?
C2 C3 C4 C5 178.9(4) . . . . ?
N1 C4 C5 C6 178.6(3) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
N1 C4 C5 C10 -0.1(3) . . . . ?
C3 C4 C5 C10 -179.3(4) . . . . ?
C10 C5 C6 C7 1.6(4) . . . . ?
C4 C5 C6 C7 -177.0(3) . . . . ?
C5 C6 C7 C8 1.0(4) . . . . ?
C6 C7 C8 C9 -1.8(4) . . . . ?
C6 C7 C8 Br1 177.3(2) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
Br1 C8 C9 C10 -179.05(16) . . . . ?
C8 C9 C10 C5 2.5(3) . . . . ?
C8 C9 C10 C11 -178.1(2) . . . . ?
C6 C5 C10 C9 -3.4(4) . . . . ?
C4 C5 C10 C9 175.5(2) . . . . ?
C6 C5 C10 C11 177.1(2) . . . . ?
C4 C5 C10 C11 -4.0(3) . . . . ?
C4 N1 C11 C12 113.5(2) . . . . ?
N2 N1 C11 C12 -61.0(3) . . . . ?
C4 N1 C11 C10 -6.5(3) . . . . ?
N2 N1 C11 C10 179.1(2) . . . . ?
C9 C10 C11 N1 -173.4(2) . . . . ?
C5 C10 C11 N1 6.0(2) . . . . ?
C9 C10 C11 C12 70.6(3) . . . . ?
C5 C10 C11 C12 -110.0(2) . . . . ?
N1 C11 C12 C13 173.02(18) . . . . ?
C10 C11 C12 C13 -77.2(2) . . . . ?
C11 C12 C13 O1 -6.7(3) . . . . ?
C11 C12 C13 C14 173.92(18) . . . . ?
O1 C13 C14 C15 8.2(3) . . . . ?
C12 C13 C14 C15 -172.5(2) . . . . ?
O1 C13 C14 C19 -170.0(2) . . . . ?
C12 C13 C14 C19 9.3(3) . . . . ?
C19 C14 C15 C16 0.7(4) . . . . ?
C13 C14 C15 C16 -177.5(2) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C15 C16 C17 C18 -0.5(5) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
C17 C18 C19 C14 1.1(4) . . . . ?
C15 C14 C19 C18 -1.3(4) . . . . ?
C13 C14 C19 C18 176.9(2) . . . . ?
