#------------------------------------------------------------------------------
#$Date: 2020-10-06 13:23:25 +0200 (mar 06 de oct de 2020) $
#$Revision: 258016 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/05/7240582.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_7240582
loop_
_publ_author_name
'Patel, Divyang M.'
'Patel, Hetal J.'
'Padrón, José M.'
'Patel, Hitendra M.'
_publ_section_title
;
 A novel substrate directed multicomponent reaction for the syntheses of
 tetrahydro-spiro[pyrazolo[4,3-f]quinoline]-8,5′-pyrimidines and
 tetrahydro-pyrazolo[4,3-f]pyrimido[4,5-b]quinolines via selective
 multiple C--C bond formation under metal-free conditions
;
_journal_issue                   33
_journal_name_full               'RSC Advances'
_journal_page_first              19600
_journal_page_last               19609
_journal_paper_doi               10.1039/D0RA02990D
_journal_volume                  10
_journal_year                    2020
_chemical_formula_moiety         'C18 H12 BR N5 O2'
_chemical_formula_sum            'C18 H12 Br N5 O2'
_chemical_formula_weight         410.24
_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-2018/3
_audit_update_record
;
2020-03-13 deposited with the CCDC.	2020-05-08 downloaded from the CCDC.
;
_cell_angle_alpha                94.851(4)
_cell_angle_beta                 97.256(4)
_cell_angle_gamma                111.253(3)
_cell_formula_units_Z            2
_cell_length_a                   10.1063(13)
_cell_length_b                   10.6214(12)
_cell_length_c                   12.8286(16)
_cell_measurement_reflns_used    3708
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      2.2
_cell_volume                     1260.4(3)
_computing_cell_refinement       'SAINT V8.38A (BRUKER AXS INC.,2017)'
_computing_data_collection       'APEX3 INC. BRUKER SOFTWARE PACKAGE'
_computing_data_reduction        'SAINT V8.38A (BRUKER AXS INC.,2017)'
_computing_molecular_graphics    'ORTEP3 MERCURY AND PLATON'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT-2014/5 (SHELDRICK,2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'BRUKER D8 VENTURE,PHOTON 200'
_diffrn_measurement_method       'PHI AND OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            36113
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.494
_diffrn_reflns_theta_min         2.194
_diffrn_source                   'FINE FOCUS SEALED TUBE'
_exptl_absorpt_coefficient_mu    1.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS-2016/2'
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.081
_exptl_crystal_density_meas      1.081
_exptl_crystal_density_method    'NOT MEASURED'
_exptl_crystal_description       'BLOCK TYPE'
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.258
_exptl_transmission_factor_max   0.7454
_exptl_transmission_factor_min   0.4850
_platon_squeeze_details
;
;
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5181
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0584
_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)+(0.1160P)²+0.1783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1734
_refine_ls_wR_factor_ref         0.1865
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3708
_reflns_number_total             5181
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra02990d2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI SCAN' was
changed to 'multi-scan' 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 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7240580--7240582.cif.
;
_cod_database_code               7240582
_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.
;
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 0.47503(5) 0.65155(5) 0.58689(3) 0.0986(3) Uani 1 1 d . . . . .
O1 O -0.0441(2) 0.6728(2) 0.33058(17) 0.0597(6) Uani 1 1 d . . . . .
C4 C -0.2119(3) 0.4530(3) 0.0806(2) 0.0413(6) Uani 1 1 d . . . . .
N2 N -0.3289(2) 0.4927(2) 0.06412(18) 0.0493(6) Uani 1 1 d . . . . .
H2 H -0.390611 0.456823 0.006790 0.059 Uiso 1 1 calc R U . . .
N3 N -0.2060(2) 0.3646(2) 0.00579(18) 0.0475(5) Uani 1 1 d . . . . .
H3 H -0.270335 0.335296 -0.050642 0.057 Uiso 1 1 calc R U . . .
C12 C 0.0037(3) 0.4642(3) 0.1909(2) 0.0397(5) Uani 1 1 d . . . . .
H12 H 0.061664 0.537919 0.155305 0.048 Uiso 1 1 calc R U . . .
C1 C -0.1099(3) 0.5084(3) 0.1747(2) 0.0399(5) Uani 1 1 d . . . . .
N1 N -0.2501(2) 0.6390(2) 0.22216(19) 0.0509(6) Uani 1 1 d . . . . .
H1 H -0.264371 0.696361 0.266337 0.061 Uiso 1 1 calc R U . . .
C5 C -0.0958(3) 0.3207(3) 0.0197(2) 0.0455(6) Uani 1 1 d . . . . .
O2 O -0.4562(2) 0.6161(2) 0.11710(19) 0.0642(6) Uani 1 1 d . . . . .
C11 C 0.0116(3) 0.3664(3) 0.1123(2) 0.0423(6) Uani 1 1 d . . . . .
C2 C -0.1273(3) 0.6123(3) 0.2495(2) 0.0427(6) Uani 1 1 d . . . . .
C3 C -0.3520(3) 0.5838(3) 0.1320(2) 0.0483(6) Uani 1 1 d . . . . .
C10 C 0.1204(3) 0.3081(3) 0.1191(2) 0.0503(7) Uani 1 1 d . . . . .
C13 C 0.1163(3) 0.5146(3) 0.2875(2) 0.0424(6) Uani 1 1 d . . . . .
C18 C 0.2532(3) 0.6069(3) 0.2842(2) 0.0511(7) Uani 1 1 d . . . . .
H18 H 0.273704 0.641389 0.221312 0.061 Uiso 1 1 calc R U . . .
C14 C 0.0890(3) 0.4626(3) 0.3818(2) 0.0545(7) Uani 1 1 d . . . . .
H14 H -0.002018 0.399540 0.385143 0.065 Uiso 1 1 calc R U . . .
C6 C -0.0929(4) 0.2240(3) -0.0636(2) 0.0577(7) Uani 1 1 d . . . . .
H6 H -0.164011 0.196566 -0.123622 0.069 Uiso 1 1 calc R U . . .
N5 N 0.3055(4) 0.2387(4) 0.1560(3) 0.0841(10) Uani 1 1 d . . . . .
C17 C 0.3600(3) 0.6486(3) 0.3727(3) 0.0604(8) Uani 1 1 d . . . . .
H17 H 0.451482 0.711075 0.369639 0.072 Uiso 1 1 calc R U . . .
C8 C 0.1161(4) 0.2138(3) 0.0337(3) 0.0583(8) Uani 1 1 d . . . . .
C9 C 0.2435(4) 0.3187(4) 0.1917(3) 0.0689(9) Uani 1 1 d . . . . .
H9 H 0.276019 0.375367 0.256479 0.083 Uiso 1 1 calc R U . . .
C15 C 0.1942(4) 0.5028(4) 0.4701(2) 0.0642(9) Uani 1 1 d . . . . .
H15 H 0.175196 0.467475 0.532898 0.077 Uiso 1 1 calc R U . . .
C16 C 0.3298(4) 0.5973(4) 0.4641(3) 0.0606(8) Uani 1 1 d . . . . .
C7 C 0.0114(4) 0.1714(3) -0.0572(3) 0.0632(8) Uani 1 1 d . . . . .
H7 H 0.012728 0.108846 -0.111873 0.076 Uiso 1 1 calc R U . . .
N4 N 0.2277(3) 0.1754(3) 0.0599(3) 0.0765(9) Uani 1 1 d . . . . .
H4 H 0.247087 0.117389 0.020093 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 0.0033 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
N3 C4 N2 116.0(2) . . ?
N3 C4 C1 124.8(2) . . ?
N2 C4 C1 119.2(2) . . ?
C3 N2 C4 124.4(2) . . ?
C3 N2 H2 117.8 . . ?
C4 N2 H2 117.8 . . ?
C4 N3 C5 118.0(2) . . ?
C4 N3 H3 121.0 . . ?
C5 N3 H3 121.0 . . ?
C1 C12 C11 118.5(2) . . ?
C1 C12 C13 122.7(2) . . ?
C11 C12 C13 118.8(2) . . ?
C1 C12 H12 90.1 . . ?
C11 C12 H12 90.1 . . ?
C13 C12 H12 90.1 . . ?
C12 C1 C4 118.1(2) . . ?
C12 C1 C2 123.4(2) . . ?
C4 C1 C2 118.5(2) . . ?
C3 N1 C2 127.1(2) . . ?
C3 N1 H1 116.5 . . ?
C2 N1 H1 116.5 . . ?
N3 C5 C11 122.4(2) . . ?
N3 C5 C6 116.6(3) . . ?
C11 C5 C6 121.0(3) . . ?
C12 C11 C5 118.1(2) . . ?
C12 C11 C10 125.0(3) . . ?
C5 C11 C10 117.0(2) . . ?
O1 C2 N1 119.6(2) . . ?
O1 C2 C1 125.3(2) . . ?
N1 C2 C1 115.0(2) . . ?
O2 C3 N2 123.6(3) . . ?
O2 C3 N1 120.7(2) . . ?
N2 C3 N1 115.7(2) . . ?
C8 C10 C9 103.5(3) . . ?
C8 C10 C11 118.6(3) . . ?
C9 C10 C11 137.9(3) . . ?
C18 C13 C14 118.4(3) . . ?
C18 C13 C12 121.1(2) . . ?
C14 C13 C12 120.4(2) . . ?
C17 C18 C13 121.1(3) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C15 C14 C13 121.0(3) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 H6 119.2 . . ?
C5 C6 H6 119.2 . . ?
C9 N5 N4 106.0(3) . . ?
C16 C17 C18 119.2(3) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
N4 C8 C7 129.5(3) . . ?
N4 C8 C10 106.6(3) . . ?
C7 C8 C10 123.8(3) . . ?
N5 C9 C10 111.6(4) . . ?
N5 C9 H9 124.2 . . ?
C10 C9 H9 124.2 . . ?
C14 C15 C16 118.9(3) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C17 C16 C15 121.4(3) . . ?
C17 C16 Br1 120.2(3) . . ?
C15 C16 Br1 118.4(3) . . ?
C6 C7 C8 118.1(3) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 H7 121.0 . . ?
C8 N4 N5 112.2(3) . . ?
C8 N4 H4 123.9 . . ?
N5 N4 H4 123.9 . . ?
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 C16 1.902(3) . ?
O1 C2 1.215(3) . ?
C4 N3 1.307(3) . ?
C4 N2 1.391(3) . ?
C4 C1 1.411(4) . ?
N2 C3 1.350(4) . ?
N2 H2 0.8600 . ?
N3 C5 1.353(3) . ?
N3 H3 0.8600 . ?
C12 C1 1.389(4) . ?
C12 C11 1.416(4) . ?
C12 C13 1.486(4) . ?
C12 H12 0.9800 . ?
C1 C2 1.475(3) . ?
N1 C3 1.374(3) . ?
N1 C2 1.380(3) . ?
N1 H1 0.8600 . ?
C5 C11 1.422(4) . ?
C5 C6 1.429(4) . ?
O2 C3 1.219(3) . ?
C11 C10 1.442(4) . ?
C10 C8 1.406(4) . ?
C10 C9 1.419(5) . ?
C13 C18 1.384(4) . ?
C13 C14 1.390(4) . ?
C18 C17 1.381(4) . ?
C18 H18 0.9300 . ?
C14 C15 1.371(4) . ?
C14 H14 0.9300 . ?
C6 C7 1.357(5) . ?
C6 H6 0.9300 . ?
N5 C9 1.311(4) . ?
N5 N4 1.350(5) . ?
C17 C16 1.358(5) . ?
C17 H17 0.9300 . ?
C8 N4 1.346(4) . ?
C8 C7 1.391(5) . ?
C9 H9 0.9300 . ?
C15 C16 1.391(5) . ?
C15 H15 0.9300 . ?
C7 H7 0.9300 . ?
N4 H4 0.8600 . ?
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
N3 C4 N2 C3 -179.3(3) . . . . ?
C1 C4 N2 C3 0.9(4) . . . . ?
N2 C4 N3 C5 -178.5(2) . . . . ?
C1 C4 N3 C5 1.3(4) . . . . ?
C11 C12 C1 C4 0.2(4) . . . . ?
C13 C12 C1 C4 -179.3(2) . . . . ?
C11 C12 C1 C2 -178.4(2) . . . . ?
C13 C12 C1 C2 2.1(4) . . . . ?
N3 C4 C1 C12 -1.6(4) . . . . ?
N2 C4 C1 C12 178.1(2) . . . . ?
N3 C4 C1 C2 177.0(3) . . . . ?
N2 C4 C1 C2 -3.2(4) . . . . ?
C4 N3 C5 C11 0.4(4) . . . . ?
C4 N3 C5 C6 179.9(3) . . . . ?
C1 C12 C11 C5 1.3(4) . . . . ?
C13 C12 C11 C5 -179.1(2) . . . . ?
C1 C12 C11 C10 -178.2(3) . . . . ?
C13 C12 C11 C10 1.4(4) . . . . ?
N3 C5 C11 C12 -1.7(4) . . . . ?
C6 C5 C11 C12 178.9(3) . . . . ?
N3 C5 C11 C10 177.8(3) . . . . ?
C6 C5 C11 C10 -1.6(4) . . . . ?
C3 N1 C2 O1 177.5(3) . . . . ?
C3 N1 C2 C1 -2.9(4) . . . . ?
C12 C1 C2 O1 2.2(4) . . . . ?
C4 C1 C2 O1 -176.4(3) . . . . ?
C12 C1 C2 N1 -177.4(3) . . . . ?
C4 C1 C2 N1 4.0(4) . . . . ?
C4 N2 C3 O2 -179.0(3) . . . . ?
C4 N2 C3 N1 0.4(4) . . . . ?
C2 N1 C3 O2 -179.9(3) . . . . ?
C2 N1 C3 N2 0.7(4) . . . . ?
C12 C11 C10 C8 -178.8(3) . . . . ?
C5 C11 C10 C8 1.7(4) . . . . ?
C12 C11 C10 C9 0.1(5) . . . . ?
C5 C11 C10 C9 -179.4(3) . . . . ?
C1 C12 C13 C18 -105.1(3) . . . . ?
C11 C12 C13 C18 75.3(3) . . . . ?
C1 C12 C13 C14 79.3(3) . . . . ?
C11 C12 C13 C14 -100.3(3) . . . . ?
C14 C13 C18 C17 -1.1(4) . . . . ?
C12 C13 C18 C17 -176.8(3) . . . . ?
C18 C13 C14 C15 0.9(4) . . . . ?
C12 C13 C14 C15 176.5(3) . . . . ?
N3 C5 C6 C7 -178.9(3) . . . . ?
C11 C5 C6 C7 0.6(5) . . . . ?
C13 C18 C17 C16 0.4(5) . . . . ?
C9 C10 C8 N4 0.9(3) . . . . ?
C11 C10 C8 N4 -179.9(3) . . . . ?
C9 C10 C8 C7 179.9(3) . . . . ?
C11 C10 C8 C7 -1.0(5) . . . . ?
N4 N5 C9 C10 0.8(4) . . . . ?
C8 C10 C9 N5 -1.1(4) . . . . ?
C11 C10 C9 N5 180.0(4) . . . . ?
C13 C14 C15 C16 0.1(4) . . . . ?
C18 C17 C16 C15 0.6(5) . . . . ?
C18 C17 C16 Br1 179.5(2) . . . . ?
C14 C15 C16 C17 -0.8(5) . . . . ?
C14 C15 C16 Br1 -179.7(2) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
N4 C8 C7 C6 178.6(3) . . . . ?
C10 C8 C7 C6 -0.1(5) . . . . ?
C7 C8 N4 N5 -179.4(3) . . . . ?
C10 C8 N4 N5 -0.5(4) . . . . ?
C9 N5 N4 C8 -0.2(4) . . . . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.071 0.000 0.415 524 101 ' '
