#------------------------------------------------------------------------------
#$Date: 2021-11-04 15:09:48 +0100 (Thu 04 de Nov de 2021) $
#$Revision: 270300 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/91/7129194.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_7129194
loop_
_publ_author_name
'Biswas, Subhamoy'
'Porashar, Bikoshita'
'Arandhara, Pallav Jyoti'
'Saikia, Anil K.'
_publ_section_title
;
 Synthesis of pyrimido[2,1-a]isoindolone and
 isoindolo[2,1-a]quinazolinone via intramolecular aza-Prins
 type reaction.
;
_journal_issue                   88
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11701
_journal_page_last               11704
_journal_paper_doi               10.1039/d1cc04554g
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-10-14 deposited with the CCDC.	2021-10-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.695(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5567(6)
_cell_length_b                   9.7212(6)
_cell_length_c                   15.0352(9)
_cell_measurement_reflns_used    9425
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.01
_cell_measurement_theta_min      2.46
_cell_volume                     1393.91(15)
_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 1.000
_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  0.0822
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            68044
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_min         2.456
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scans
_exptl_absorpt_process_details   multi-scans
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3453
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0499
_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)+(0.1000P)²+0.2056P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1768
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2375
_reflns_number_total             3453
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc04554g3.cif
_cod_data_source_block           SB-1P_0m_a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7129194
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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
N1 N 0.20557(13) 0.32576(14) 0.57558(9) 0.0407(3) Uani 1 1 d . . . . .
O2 O 0.01753(13) 0.19074(15) 0.59235(12) 0.0699(4) Uani 1 1 d . . . . .
N2 N 0.38442(14) 0.24670(15) 0.48250(10) 0.0480(4) Uani 1 1 d . . . . .
O1 O 0.58900(16) 0.12771(17) 0.46788(13) 0.0794(5) Uani 1 1 d . . . . .
C8 C 0.33325(15) 0.36243(16) 0.53058(10) 0.0375(3) Uani 1 1 d . . . . .
H5 H 0.312206 0.438490 0.489071 0.045 Uiso 1 1 calc R U . . .
C12 C 0.15006(15) 0.43458(17) 0.62762(11) 0.0392(4) Uani 1 1 d . . . . .
C5 C 0.45917(16) 0.40006(17) 0.59285(11) 0.0407(4) Uani 1 1 d . . . . .
C6 C 0.56929(16) 0.31420(18) 0.57443(12) 0.0457(4) Uani 1 1 d . . . . .
C9 C 0.12763(17) 0.20945(18) 0.55734(13) 0.0483(4) Uani 1 1 d . . . . .
C13 C 0.11993(18) 0.56066(19) 0.58774(12) 0.0482(4) Uani 1 1 d . . . . .
H10 H 0.128254 0.571715 0.526872 0.058 Uiso 1 1 calc R U . . .
C7 C 0.52193(18) 0.21685(19) 0.50379(13) 0.0506(4) Uani 1 1 d . . . . .
C17 C 0.13464(18) 0.4171(2) 0.71791(12) 0.0543(5) Uani 1 1 d . . . . .
H14 H 0.153998 0.332750 0.745181 0.065 Uiso 1 1 calc R U . . .
C4 C 0.47744(19) 0.5016(2) 0.65658(12) 0.0535(5) Uani 1 1 d . . . . .
H4 H 0.404839 0.561422 0.668046 0.064 Uiso 1 1 calc R U . . .
C1 C 0.70045(18) 0.3256(2) 0.62001(14) 0.0608(6) Uani 1 1 d . . . . .
H1 H 0.774080 0.267932 0.607047 0.073 Uiso 1 1 calc R U . . .
C10 C 0.18220(19) 0.1050(2) 0.49464(16) 0.0582(5) Uani 1 1 d . . . . .
H6 H 0.103388 0.065034 0.459844 0.070 Uiso 1 1 calc R U . . .
H7 H 0.227729 0.031679 0.529414 0.070 Uiso 1 1 calc R U . . .
C11 C 0.2850(2) 0.1620(2) 0.43140(14) 0.0599(5) Uani 1 1 d . . . . .
H9 H 0.333192 0.087375 0.403340 0.072 Uiso 1 1 calc R U . . .
H8 H 0.235790 0.216224 0.385142 0.072 Uiso 1 1 calc R U . . .
C14 C 0.0776(2) 0.6699(2) 0.63826(15) 0.0641(5) Uani 1 1 d . . . . .
H11 H 0.059848 0.754955 0.611614 0.077 Uiso 1 1 calc R U . . .
C16 C 0.0894(2) 0.5288(3) 0.76733(13) 0.0696(6) Uani 1 1 d . . . . .
H13 H 0.077918 0.518629 0.827931 0.083 Uiso 1 1 calc R U . . .
C2 C 0.7171(2) 0.4252(3) 0.68486(15) 0.0725(7) Uani 1 1 d . . . . .
H2 H 0.803222 0.434328 0.716819 0.087 Uiso 1 1 calc R U . . .
C3 C 0.6077(2) 0.5120(3) 0.70335(15) 0.0710(6) Uani 1 1 d . . . . .
H3 H 0.621503 0.578321 0.747645 0.085 Uiso 1 1 calc R U . . .
C15 C 0.0618(2) 0.6533(3) 0.72683(16) 0.0716(6) Uani 1 1 d . . . . .
H12 H 0.032019 0.726966 0.760277 0.086 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
C9 N1 C12 120.04(13) . . ?
C9 N1 C8 124.15(14) . . ?
C12 N1 C8 114.62(12) . . ?
C7 N2 C8 113.69(15) . . ?
C7 N2 C11 126.56(16) . . ?
C8 N2 C11 118.73(13) . . ?
N2 C8 N1 111.03(13) . . ?
N2 C8 C5 102.48(12) . . ?
N1 C8 C5 114.86(13) . . ?
N2 C8 H5 109.4 . . ?
N1 C8 H5 109.4 . . ?
C5 C8 H5 109.4 . . ?
C17 C12 C13 119.99(16) . . ?
C17 C12 N1 120.62(16) . . ?
C13 C12 N1 119.27(14) . . ?
C4 C5 C6 120.43(16) . . ?
C4 C5 C8 131.27(15) . . ?
C6 C5 C8 108.25(15) . . ?
C5 C6 C1 121.65(19) . . ?
C5 C6 C7 109.23(14) . . ?
C1 C6 C7 129.12(17) . . ?
O2 C9 N1 120.59(17) . . ?
O2 C9 C10 120.92(17) . . ?
N1 C9 C10 118.48(15) . . ?
C14 C13 C12 120.11(18) . . ?
C14 C13 H10 119.9 . . ?
C12 C13 H10 119.9 . . ?
O1 C7 N2 124.8(2) . . ?
O1 C7 C6 128.91(18) . . ?
N2 C7 C6 106.23(14) . . ?
C12 C17 C16 118.7(2) . . ?
C12 C17 H14 120.6 . . ?
C16 C17 H14 120.6 . . ?
C5 C4 C3 118.1(2) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C2 C1 C6 117.63(19) . . ?
C2 C1 H1 121.2 . . ?
C6 C1 H1 121.2 . . ?
C9 C10 C11 114.32(16) . . ?
C9 C10 H6 108.7 . . ?
C11 C10 H6 108.7 . . ?
C9 C10 H7 108.7 . . ?
C11 C10 H7 108.7 . . ?
H6 C10 H7 107.6 . . ?
N2 C11 C10 107.83(16) . . ?
N2 C11 H9 110.1 . . ?
C10 C11 H9 110.1 . . ?
N2 C11 H8 110.1 . . ?
C10 C11 H8 110.1 . . ?
H9 C11 H8 108.5 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H11 119.9 . . ?
C13 C14 H11 119.9 . . ?
C15 C16 C17 120.37(19) . . ?
C15 C16 H13 119.8 . . ?
C17 C16 H13 119.8 . . ?
C1 C2 C3 121.09(19) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 121.0(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C14 C15 C16 120.6(2) . . ?
C14 C15 H12 119.7 . . ?
C16 C15 H12 119.7 . . ?
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
N1 C9 1.372(2) . ?
N1 C12 1.437(2) . ?
N1 C8 1.4765(19) . ?
O2 C9 1.220(2) . ?
N2 C7 1.364(2) . ?
N2 C8 1.440(2) . ?
N2 C11 1.441(2) . ?
O1 C7 1.224(2) . ?
C8 C5 1.521(2) . ?
C8 H5 0.9800 . ?
C12 C17 1.385(2) . ?
C12 C13 1.386(2) . ?
C5 C4 1.379(3) . ?
C5 C6 1.385(2) . ?
C6 C1 1.394(2) . ?
C6 C7 1.472(3) . ?
C9 C10 1.502(3) . ?
C13 C14 1.381(3) . ?
C13 H10 0.9300 . ?
C17 C16 1.400(3) . ?
C17 H14 0.9300 . ?
C4 C3 1.394(3) . ?
C4 H4 0.9300 . ?
C1 C2 1.376(3) . ?
C1 H1 0.9300 . ?
C10 C11 1.516(3) . ?
C10 H6 0.9700 . ?
C10 H7 0.9700 . ?
C11 H9 0.9700 . ?
C11 H8 0.9700 . ?
C14 C15 1.359(4) . ?
C14 H11 0.9300 . ?
C16 C15 1.373(4) . ?
C16 H13 0.9300 . ?
C2 C3 1.386(4) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C15 H12 0.9300 . ?
