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#$Date: 2020-08-06 17:43:29 +0300 (Thu, 06 Aug 2020) $
#$Revision: 255092 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157548.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_7157548
loop_
_publ_author_name
'Bou-Petit, Elisabeth'
'Plans, Arnau'
'Rodríguez-Picazo, Nieves'
'Torres-Coll, Antoni'
'Puigjaner, Cristina'
'Font-Bardia, Mercè'
'Teixidó, Jordi'
'Ramon Y Cajal, Santiago'
'Estrada-Tejedor, Roger'
'Borrell, José I'
_publ_section_title
;
 C4-C5 fused pyrazol-3-amines: when the degree of unsaturation and
 electronic characteristics of the fused ring controls regioselectivity in
 Ullmann and acylation reactions.
;
_journal_issue                   27
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5145
_journal_page_last               5156
_journal_paper_doi               10.1039/d0ob00796j
_journal_volume                  18
_journal_year                    2020
_chemical_formula_sum            'C18 H14 N4 O'
_chemical_formula_weight         302.33
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-03-11 deposited with the CCDC.	2020-06-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 128.1800(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.7141(13)
_cell_length_b                   6.4562(3)
_cell_length_c                   20.6251(10)
_cell_measurement_reflns_used    7790
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.95
_cell_volume                     2900.9(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24789
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.605
_diffrn_reflns_theta_min         2.947
_diffrn_source                   microfocus
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6825
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       prism
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.292
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.066
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     216
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0646
_refine_ls_R_factor_gt           0.0491
_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)+(0.0807P)²+2.6312P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1476
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2631
_reflns_number_total             3348
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob00796j5.cif
_cod_data_source_block           mo_023WB46_0m_a
_cod_depositor_comments
'Adding full bibliography for 7157548--7157549.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7157548
_shelx_shelxl_version_number     2018/3
_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   0.974
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.29346(6) 0.8892(2) 0.58507(8) 0.0331(3) Uani 1 1 d . . . . .
N1 N 0.32782(6) 0.7044(2) 0.52798(9) 0.0246(3) Uani 1 1 d . . . . .
H1N H 0.294315 0.628276 0.500476 0.030 Uiso 1 1 calc R U . . .
N2 N 0.37314(6) 0.5226(2) 0.47322(8) 0.0218(3) Uani 1 1 d . . . . .
N3 N 0.42539(6) 0.5497(2) 0.47790(8) 0.0227(3) Uani 1 1 d . . . . .
N4 N 0.50789(7) 0.7858(2) 0.54386(10) 0.0293(3) Uani 1 1 d . . . . .
H4NA H 0.5254(10) 0.705(4) 0.5282(13) 0.036(6) Uiso 1 1 d . . . . .
H4NB H 0.5215(14) 0.917(5) 0.5636(18) 0.069(8) Uiso 1 1 d . . . . .
C1 C 0.42307(8) 1.3272(3) 0.68974(12) 0.0349(4) Uani 1 1 d . . . . .
H1 H 0.430397 1.364787 0.651974 0.042 Uiso 1 1 calc R U . . .
C2 C 0.43355(9) 1.4701(3) 0.74808(14) 0.0457(6) Uani 1 1 d . . . . .
H2 H 0.447846 1.605322 0.749813 0.055 Uiso 1 1 calc R U . . .
C3 C 0.42317(9) 1.4154(4) 0.80316(14) 0.0469(6) Uani 1 1 d . . . . .
H3 H 0.430685 1.513061 0.842937 0.056 Uiso 1 1 calc R U . . .
C4 C 0.40196(9) 1.2202(4) 0.80103(12) 0.0418(5) Uani 1 1 d . . . . .
H4 H 0.394960 1.183850 0.839234 0.050 Uiso 1 1 calc R U . . .
C5 C 0.39088(8) 1.0769(3) 0.74302(11) 0.0340(4) Uani 1 1 d . . . . .
H5 H 0.375822 0.943094 0.741170 0.041 Uiso 1 1 calc R U . . .
C6 C 0.40184(7) 1.1292(3) 0.68707(10) 0.0280(4) Uani 1 1 d . . . . .
C7 C 0.39258(7) 0.9752(3) 0.62695(10) 0.0246(4) Uani 1 1 d . . . . .
C8 C 0.43366(7) 0.9490(3) 0.61145(10) 0.0237(3) Uani 1 1 d . . . . .
H8 H 0.469169 1.034086 0.638381 0.028 Uiso 1 1 calc R U . . .
C9 C 0.42300(7) 0.7949(2) 0.55519(10) 0.0214(3) Uani 1 1 d . . . . .
C10 C 0.37132(7) 0.6710(2) 0.51789(9) 0.0213(3) Uani 1 1 d . . . . .
C11 C 0.33566(7) 0.8563(3) 0.58086(10) 0.0263(4) Uani 1 1 d . . . . .
C12 C 0.45435(7) 0.7127(2) 0.52625(10) 0.0207(3) Uani 1 1 d . . . . .
C13 C 0.33313(7) 0.3532(2) 0.42769(10) 0.0219(3) Uani 1 1 d . . . . .
C14 C 0.29856(8) 0.2663(3) 0.44864(11) 0.0269(4) Uani 1 1 d . . . . .
H14 H 0.301878 0.318474 0.494318 0.032 Uiso 1 1 calc R U . . .
C15 C 0.25922(8) 0.1031(3) 0.40258(12) 0.0310(4) Uani 1 1 d . . . . .
H15 H 0.234379 0.047124 0.415515 0.037 Uiso 1 1 calc R U . . .
C16 C 0.25584(9) 0.0211(3) 0.33789(12) 0.0331(4) Uani 1 1 d . . . . .
H16 H 0.229140 -0.091749 0.306826 0.040 Uiso 1 1 calc R U . . .
C17 C 0.29180(9) 0.1050(3) 0.31873(11) 0.0338(4) Uani 1 1 d . . . . .
H17 H 0.290166 0.047123 0.275057 0.041 Uiso 1 1 calc R U . . .
C18 C 0.32999(8) 0.2720(3) 0.36256(11) 0.0284(4) Uani 1 1 d . . . . .
H18 H 0.353805 0.330567 0.348391 0.034 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'
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
C10 N1 C11 120.77(13) . . ?
C10 N1 H1N 119.6 . . ?
C11 N1 H1N 119.6 . . ?
C10 N2 N3 109.69(12) . . ?
C10 N2 C13 130.78(13) . . ?
N3 N2 C13 119.51(12) . . ?
C12 N3 N2 105.69(12) . . ?
C12 N4 H4NA 116.2(14) . . ?
C12 N4 H4NB 121.1(19) . . ?
H4NA N4 H4NB 122(2) . . ?
C6 C1 C2 119.8(2) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.62(18) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 119.24(17) . . ?
C1 C6 C7 119.90(17) . . ?
C5 C6 C7 120.85(17) . . ?
C8 C7 C11 120.20(15) . . ?
C8 C7 C6 122.59(15) . . ?
C11 C7 C6 117.14(14) . . ?
C7 C8 C9 119.72(15) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 118.81(14) . . ?
C10 C9 C12 103.91(14) . . ?
C8 C9 C12 137.13(15) . . ?
N2 C10 N1 128.78(14) . . ?
N2 C10 C9 109.05(14) . . ?
N1 C10 C9 122.17(14) . . ?
O1 C11 N1 118.75(15) . . ?
O1 C11 C7 123.35(15) . . ?
N1 C11 C7 117.86(14) . . ?
N3 C12 N4 121.62(14) . . ?
N3 C12 C9 111.61(14) . . ?
N4 C12 C9 126.77(15) . . ?
C14 C13 C18 120.23(15) . . ?
C14 C13 N2 120.77(14) . . ?
C18 C13 N2 118.99(15) . . ?
C15 C14 C13 119.69(15) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 120.49(16) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.49(16) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 120.75(17) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C13 119.30(16) . . ?
C17 C18 H18 120.4 . . ?
C13 C18 H18 120.4 . . ?
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
O1 C11 1.243(2) . ?
N1 C10 1.361(2) . ?
N1 C11 1.380(2) . ?
N1 H1N 0.8800 . ?
N2 C10 1.352(2) . ?
N2 N3 1.4013(18) . ?
N2 C13 1.421(2) . ?
N3 C12 1.325(2) . ?
N4 C12 1.375(2) . ?
N4 H4NA 0.90(2) . ?
N4 H4NB 0.91(3) . ?
C1 C6 1.394(3) . ?
C1 C2 1.397(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.380(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.483(2) . ?
C7 C8 1.370(2) . ?
C7 C11 1.459(2) . ?
C8 C9 1.414(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(2) . ?
C9 C12 1.427(2) . ?
C13 C14 1.390(2) . ?
C13 C18 1.394(2) . ?
C14 C15 1.386(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.389(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.385(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
