#------------------------------------------------------------------------------
#$Date: 2023-08-05 11:33:36 +0300 (Sat, 05 Aug 2023) $
#$Revision: 285460 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/92/1569261.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_1569261
loop_
_publ_author_name
'Zhang, Xiao'
'Bai, Fan'
'Li, Miaomiao'
'Ru, Huihui'
'Wang, Lanzhi'
_publ_section_title
;
 NiFe2O4@SiO2@PrNH2--DPA--CeCl3: a cerium-based magnetic nano dual-acid
 catalyst with high efficacy and recyclability for domino sequential
 synthesis of lactam ring-fused 1,5-benzodiazepines
;
_journal_issue                   13
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              3987
_journal_page_last               3999
_journal_paper_doi               10.1039/D2CY01778D
_journal_volume                  13
_journal_year                    2023
_chemical_formula_sum            'C20 H21 Br2 N3 O2'
_chemical_formula_weight         495.22
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2022-10-14 deposited with the CCDC.	2023-06-01 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.765(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.7492(9)
_cell_length_b                   21.4852(19)
_cell_length_c                   8.9772(6)
_cell_measurement_reflns_used    2423
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.918
_cell_measurement_theta_min      2.687
_cell_volume                     2066.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0839
_diffrn_reflns_av_sigmaI/netI    0.0908
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9916
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.12
_exptl_absorpt_coefficient_mu    3.943
_exptl_absorpt_correction_T_max  0.6709
_exptl_absorpt_correction_T_min  0.3157
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.592
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.566
_refine_diff_density_min         -1.002
_refine_diff_density_rms         0.102
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0675
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0954P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1806
_refine_ls_wR_factor_ref         0.2001
_reflns_number_gt                1881
_reflns_number_total             3630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cy01778d2.cif
_cod_data_source_block           211211d
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 1569261.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1569261
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.54078(11) 0.16258(4) 0.52035(11) 0.0980(5) Uani 1 1 d . . .
Br2 Br 0.11931(11) 0.30404(5) -0.04201(11) 0.1022(4) Uani 1 1 d . . .
N1 N 0.3304(5) 0.5023(2) 0.9220(6) 0.0538(14) Uani 1 1 d . . .
H1 H 0.3731 0.5034 1.0073 0.065 Uiso 1 1 calc R . .
N2 N 0.0909(5) 0.4359(2) 0.5621(6) 0.0528(14) Uani 1 1 d . . .
H2 H 0.0147 0.4398 0.5831 0.063 Uiso 1 1 calc R . .
N3 N 0.3033(5) 0.4582(2) 0.3873(5) 0.0461(13) Uani 1 1 d . . .
H3 H 0.3590 0.4598 0.3179 0.055 Uiso 1 1 d R . .
O1 O 0.5019(4) 0.4784(2) 0.8019(5) 0.0572(12) Uani 1 1 d . . .
O2 O 0.8295(5) 0.0762(3) 0.1351(9) 0.100(2) Uani 1 1 d . . .
H2C H 0.7813 0.0471 0.1167 0.150 Uiso 1 1 calc R . .
C1 C 0.3854(7) 0.4817(3) 0.8000(7) 0.0470(16) Uani 1 1 d . . .
C2 C 0.2021(7) 0.5225(4) 0.9113(9) 0.072(2) Uani 1 1 d . . .
H2A H 0.1965 0.5642 0.8694 0.086 Uiso 1 1 calc R . .
H2B H 0.1728 0.5242 1.0105 0.086 Uiso 1 1 calc R . .
C3 C 0.1181(6) 0.4783(3) 0.8126(8) 0.0614(19) Uani 1 1 d . . .
H3C H 0.1013 0.4414 0.8696 0.074 Uiso 1 1 calc R . .
H3D H 0.0390 0.4987 0.7851 0.074 Uiso 1 1 calc R . .
C4 C 0.1779(6) 0.4591(3) 0.6699(7) 0.0453(15) Uani 1 1 d . . .
C5 C 0.3044(6) 0.4625(3) 0.6648(7) 0.0430(15) Uani 1 1 d . . .
C6 C 0.3727(6) 0.4412(3) 0.5352(6) 0.0440(15) Uani 1 1 d . . .
H6 H 0.4498 0.4658 0.5404 0.053 Uiso 1 1 calc R . .
C7 C 0.4150(6) 0.3728(3) 0.5364(7) 0.0426(15) Uani 1 1 d . . .
C8 C 0.5053(7) 0.3536(3) 0.4445(8) 0.0571(18) Uani 1 1 d . . .
H8 H 0.5418 0.3825 0.3847 0.068 Uiso 1 1 calc R . .
C9 C 0.5418(7) 0.2915(3) 0.4409(9) 0.070(2) Uani 1 1 d . . .
H9 H 0.6023 0.2793 0.3785 0.084 Uiso 1 1 calc R . .
C10 C 0.4893(7) 0.2480(3) 0.5289(8) 0.0594(19) Uani 1 1 d . . .
C11 C 0.4003(7) 0.2653(3) 0.6192(8) 0.0609(19) Uani 1 1 d . . .
H11 H 0.3645 0.2357 0.6779 0.073 Uiso 1 1 calc R . .
C12 C 0.3620(6) 0.3275(3) 0.6251(7) 0.0519(17) Uani 1 1 d . . .
H12 H 0.3013 0.3390 0.6878 0.062 Uiso 1 1 calc R . .
C13 C 0.1058(6) 0.4067(3) 0.4213(7) 0.0457(16) Uani 1 1 d . . .
C14 C 0.2061(6) 0.4163(3) 0.3358(7) 0.0456(15) Uani 1 1 d . . .
C15 C 0.2088(7) 0.3855(3) 0.1957(8) 0.0584(18) Uani 1 1 d . . .
H15 H 0.2765 0.3908 0.1388 0.070 Uiso 1 1 calc R . .
C16 C 0.1114(8) 0.3480(3) 0.1451(8) 0.063(2) Uani 1 1 d . . .
C17 C 0.0093(8) 0.3395(3) 0.2243(9) 0.065(2) Uani 1 1 d . . .
H17 H -0.0571 0.3149 0.1864 0.078 Uiso 1 1 calc R . .
C18 C 0.0070(7) 0.3683(3) 0.3621(9) 0.067(2) Uani 1 1 d . . .
H18 H -0.0615 0.3622 0.4172 0.080 Uiso 1 1 calc R . .
C19 C 0.7745(9) 0.1191(4) 0.2216(11) 0.093(3) Uani 1 1 d . . .
H19A H 0.7911 0.1074 0.3258 0.111 Uiso 1 1 calc R . .
H19B H 0.6849 0.1175 0.1980 0.111 Uiso 1 1 calc R . .
C20 C 0.8174(10) 0.1850(4) 0.2029(14) 0.120(4) Uani 1 1 d . . .
H20A H 0.9066 0.1857 0.2008 0.180 Uiso 1 1 calc R . .
H20B H 0.7939 0.2098 0.2850 0.180 Uiso 1 1 calc R . .
H20C H 0.7792 0.2016 0.1109 0.180 Uiso 1 1 calc R . .
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
C1 N1 C2 121.4(6) . . ?
C1 N1 H1 119.3 . . ?
C2 N1 H1 119.3 . . ?
C4 N2 C13 131.1(5) . . ?
C4 N2 H2 114.4 . . ?
C13 N2 H2 114.4 . . ?
C14 N3 C6 115.3(4) . . ?
C14 N3 H3 108.1 . . ?
C6 N3 H3 107.9 . . ?
C19 O2 H2C 109.5 . . ?
O1 C1 N1 120.5(6) . . ?
O1 C1 C5 120.7(6) . . ?
N1 C1 C5 118.7(6) . . ?
N1 C2 C3 111.4(6) . . ?
N1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
N1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C4 C3 C2 112.3(6) . . ?
C4 C3 H3C 109.1 . . ?
C2 C3 H3C 109.1 . . ?
C4 C3 H3D 109.1 . . ?
C2 C3 H3D 109.1 . . ?
H3C C3 H3D 107.9 . . ?
C5 C4 N2 127.8(6) . . ?
C5 C4 C3 120.0(6) . . ?
N2 C4 C3 112.1(5) . . ?
C4 C5 C1 120.2(6) . . ?
C4 C5 C6 124.3(6) . . ?
C1 C5 C6 115.2(5) . . ?
C5 C6 N3 111.7(5) . . ?
C5 C6 C7 116.7(5) . . ?
N3 C6 C7 111.2(5) . . ?
C5 C6 H6 105.4 . . ?
N3 C6 H6 105.4 . . ?
C7 C6 H6 105.4 . . ?
C8 C7 C12 117.8(6) . . ?
C8 C7 C6 120.0(5) . . ?
C12 C7 C6 122.1(6) . . ?
C7 C8 C9 120.8(7) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 120.5(7) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.0(6) . . ?
C11 C10 Br1 120.5(6) . . ?
C9 C10 Br1 119.6(5) . . ?
C10 C11 C12 120.6(6) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 120.3(6) . . ?
C11 C12 H12 119.8 . . ?
C7 C12 H12 119.8 . . ?
C14 C13 C18 118.2(6) . . ?
C14 C13 N2 124.8(5) . . ?
C18 C13 N2 116.9(6) . . ?
C13 C14 C15 119.5(6) . . ?
C13 C14 N3 119.7(5) . . ?
C15 C14 N3 120.8(6) . . ?
C16 C15 C14 119.7(7) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 122.1(7) . . ?
C15 C16 Br2 119.2(6) . . ?
C17 C16 Br2 118.7(5) . . ?
C16 C17 C18 118.6(7) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C17 C18 C13 121.9(7) . . ?
C17 C18 H18 119.1 . . ?
C13 C18 H18 119.1 . . ?
O2 C19 C20 114.8(8) . . ?
O2 C19 H19A 108.6 . . ?
C20 C19 H19A 108.6 . . ?
O2 C19 H19B 108.6 . . ?
C20 C19 H19B 108.6 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
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 C10 1.919(7) . ?
Br2 C16 1.935(7) . ?
N1 C1 1.362(8) . ?
N1 C2 1.442(8) . ?
N1 H1 0.8600 . ?
N2 C4 1.381(8) . ?
N2 C13 1.432(8) . ?
N2 H2 0.8600 . ?
N3 C14 1.427(7) . ?
N3 C6 1.512(8) . ?
N3 H3 0.9000 . ?
O1 C1 1.253(7) . ?
O2 C19 1.370(9) . ?
O2 H2C 0.8200 . ?
C1 C5 1.492(9) . ?
C2 C3 1.539(10) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.537(9) . ?
C3 H3C 0.9700 . ?
C3 H3D 0.9700 . ?
C4 C5 1.367(8) . ?
C5 C6 1.498(8) . ?
C6 C7 1.538(8) . ?
C6 H6 0.9800 . ?
C7 C8 1.388(9) . ?
C7 C12 1.407(9) . ?
C8 C9 1.393(10) . ?
C8 H8 0.9300 . ?
C9 C10 1.375(10) . ?
C9 H9 0.9300 . ?
C10 C11 1.357(9) . ?
C11 C12 1.401(9) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.390(9) . ?
C13 C18 1.413(9) . ?
C14 C15 1.424(9) . ?
C15 C16 1.367(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.369(11) . ?
C17 C18 1.385(10) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.503(12) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
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
C2 N1 C1 O1 163.0(6) . . . . ?
C2 N1 C1 C5 -17.6(9) . . . . ?
C1 N1 C2 C3 43.0(9) . . . . ?
N1 C2 C3 C4 -43.2(9) . . . . ?
C13 N2 C4 C5 3.7(10) . . . . ?
C13 N2 C4 C3 -172.2(6) . . . . ?
C2 C3 C4 C5 22.2(9) . . . . ?
C2 C3 C4 N2 -161.6(6) . . . . ?
N2 C4 C5 C1 -172.3(5) . . . . ?
C3 C4 C5 C1 3.3(8) . . . . ?
N2 C4 C5 C6 0.4(10) . . . . ?
C3 C4 C5 C6 176.0(5) . . . . ?
O1 C1 C5 C4 172.0(5) . . . . ?
N1 C1 C5 C4 -7.4(8) . . . . ?
O1 C1 C5 C6 -1.3(8) . . . . ?
N1 C1 C5 C6 179.3(5) . . . . ?
C4 C5 C6 N3 40.3(7) . . . . ?
C1 C5 C6 N3 -146.6(5) . . . . ?
C4 C5 C6 C7 -89.1(7) . . . . ?
C1 C5 C6 C7 83.9(6) . . . . ?
C14 N3 C6 C5 -82.7(6) . . . . ?
C14 N3 C6 C7 49.6(7) . . . . ?
C5 C6 C7 C8 -163.0(6) . . . . ?
N3 C6 C7 C8 67.3(7) . . . . ?
C5 C6 C7 C12 19.1(8) . . . . ?
N3 C6 C7 C12 -110.6(6) . . . . ?
C12 C7 C8 C9 -0.1(10) . . . . ?
C6 C7 C8 C9 -178.0(6) . . . . ?
C7 C8 C9 C10 -0.2(12) . . . . ?
C8 C9 C10 C11 0.5(12) . . . . ?
C8 C9 C10 Br1 179.5(6) . . . . ?
C9 C10 C11 C12 -0.6(11) . . . . ?
Br1 C10 C11 C12 -179.6(6) . . . . ?
C10 C11 C12 C7 0.4(10) . . . . ?
C8 C7 C12 C11 0.0(10) . . . . ?
C6 C7 C12 C11 177.9(6) . . . . ?
C4 N2 C13 C14 -26.8(10) . . . . ?
C4 N2 C13 C18 157.3(6) . . . . ?
C18 C13 C14 C15 -2.7(9) . . . . ?
N2 C13 C14 C15 -178.5(6) . . . . ?
C18 C13 C14 N3 175.7(5) . . . . ?
N2 C13 C14 N3 -0.2(9) . . . . ?
C6 N3 C14 C13 60.8(7) . . . . ?
C6 N3 C14 C15 -120.9(6) . . . . ?
C13 C14 C15 C16 1.7(9) . . . . ?
N3 C14 C15 C16 -176.7(6) . . . . ?
C14 C15 C16 C17 0.8(10) . . . . ?
C14 C15 C16 Br2 -177.8(5) . . . . ?
C15 C16 C17 C18 -2.1(11) . . . . ?
Br2 C16 C17 C18 176.4(5) . . . . ?
C16 C17 C18 C13 1.0(11) . . . . ?
C14 C13 C18 C17 1.4(10) . . . . ?
N2 C13 C18 C17 177.6(6) . . . . ?
