#------------------------------------------------------------------------------
#$Date: 2020-11-06 15:13:06 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/76/7157689.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_7157689
loop_
_publ_author_name
'Chan, Chieh-Kai'
'Lai, Chien-Yu'
'Wang, Cheng-Chung'
_publ_section_title
;
 TMSOTf-catalyzed synthesis of substituted quinazolines using
 hexamethyldisilazane as a nitrogen source under neat and microwave
 irradiation conditions.
;
_journal_issue                   36
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              7201
_journal_page_last               7212
_journal_paper_doi               10.1039/d0ob01507e
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C21 H16 N2 O'
_chemical_formula_sum            'C21 H16 N2 O'
_chemical_formula_weight         312.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-03-05 deposited with the CCDC.	2020-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.6384(3)
_cell_length_b                   6.90900(10)
_cell_length_c                   30.7229(7)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    100.0(2)
_cell_measurement_theta_max      65.07
_cell_measurement_theta_min      2.88
_cell_volume                     3107.21(11)
_computing_cell_refinement       'APEX3 v2015.9-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_data_reduction        'SAINT V8.35A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 740)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            60225
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        65.073
_diffrn_reflns_theta_max         65.073
_diffrn_reflns_theta_min         2.877
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8284
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.164
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0375
_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)+(0.0472P)²+1.3833P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.0997
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2367
_reflns_number_total             2641
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob01507e2.cif
_cod_data_source_block           i17822
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'none' was changed to
'?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7157689--7157694.cif.
;
_cod_database_code               7157689
_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   0.834
_shelx_estimated_absorpt_t_max   0.900
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
O1 O 0.20890(6) 0.35914(15) 0.47376(3) 0.0200(3) Uani 1 1 d . . . . .
N1 N 0.55618(7) 0.33473(16) 0.34701(4) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.62377(7) 0.38901(16) 0.41684(4) 0.0158(3) Uani 1 1 d . . . . .
C1 C 0.55309(9) 0.35943(18) 0.39115(4) 0.0144(3) Uani 1 1 d . . . . .
C2 C 0.63727(9) 0.33371(19) 0.32804(4) 0.0151(3) Uani 1 1 d . . . . .
C3 C 0.71980(9) 0.35162(19) 0.35262(4) 0.0151(3) Uani 1 1 d . . . . .
C4 C 0.80966(9) 0.33565(19) 0.33582(4) 0.0166(3) Uani 1 1 d . . . . .
H4 H 0.818680 0.310689 0.305721 0.020 Uiso 1 1 calc R U . . .
C5 C 0.88358(9) 0.35604(19) 0.36279(5) 0.0190(3) Uani 1 1 d . . . . .
H5 H 0.943572 0.345143 0.351259 0.023 Uiso 1 1 calc R U . . .
C6 C 0.87127(9) 0.3930(2) 0.40749(5) 0.0191(3) Uani 1 1 d . . . . .
H6 H 0.923144 0.408790 0.425733 0.023 Uiso 1 1 calc R U . . .
C7 C 0.78575(9) 0.4066(2) 0.42493(4) 0.0182(3) Uani 1 1 d . . . . .
H7 H 0.778309 0.431651 0.455129 0.022 Uiso 1 1 calc R U . . .
C8 C 0.70819(9) 0.38319(19) 0.39796(4) 0.0153(3) Uani 1 1 d . . . . .
C9 C 0.46137(9) 0.35464(19) 0.41141(4) 0.0150(3) Uani 1 1 d . . . . .
C10 C 0.45272(9) 0.36193(19) 0.45681(4) 0.0158(3) Uani 1 1 d . . . . .
H10 H 0.506226 0.366221 0.474286 0.019 Uiso 1 1 calc R U . . .
C11 C 0.36836(9) 0.3630(2) 0.47665(4) 0.0174(3) Uani 1 1 d . . . . .
H11 H 0.363975 0.368777 0.507477 0.021 Uiso 1 1 calc R U . . .
C12 C 0.28924(9) 0.35556(19) 0.45127(4) 0.0162(3) Uani 1 1 d . . . . .
C13 C 0.29619(9) 0.3455(2) 0.40612(4) 0.0171(3) Uani 1 1 d . . . . .
H13 H 0.242606 0.339181 0.388732 0.021 Uiso 1 1 calc R U . . .
C14 C 0.38187(9) 0.34474(19) 0.38660(4) 0.0164(3) Uani 1 1 d . . . . .
H14 H 0.386268 0.337346 0.355791 0.020 Uiso 1 1 calc R U . . .
C15 C 0.12582(9) 0.3576(2) 0.44921(5) 0.0200(3) Uani 1 1 d . . . . .
H15A H 0.124750 0.469047 0.429492 0.030 Uiso 1 1 calc R U . . .
H15B H 0.073621 0.364804 0.469119 0.030 Uiso 1 1 calc R U . . .
H15C H 0.122182 0.237796 0.432212 0.030 Uiso 1 1 calc R U . . .
C16 C 0.63470(9) 0.3108(2) 0.27977(4) 0.0157(3) Uani 1 1 d . . . . .
C17 C 0.57412(9) 0.1763(2) 0.26169(4) 0.0180(3) Uani 1 1 d . . . . .
H17 H 0.536549 0.100248 0.280217 0.022 Uiso 1 1 calc R U . . .
C18 C 0.56850(9) 0.1532(2) 0.21700(4) 0.0207(3) Uani 1 1 d . . . . .
H18 H 0.528230 0.059481 0.205005 0.025 Uiso 1 1 calc R U . . .
C19 C 0.62174(9) 0.2670(2) 0.18972(4) 0.0220(3) Uani 1 1 d . . . . .
H19 H 0.617544 0.251717 0.159055 0.026 Uiso 1 1 calc R U . . .
C20 C 0.68087(10) 0.4025(2) 0.20716(5) 0.0214(3) Uani 1 1 d . . . . .
H20 H 0.716593 0.481503 0.188428 0.026 Uiso 1 1 calc R U . . .
C21 C 0.68813(9) 0.4234(2) 0.25194(4) 0.0184(3) Uani 1 1 d . . . . .
H21 H 0.729741 0.514909 0.263743 0.022 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C12 O1 C15 117.76(10) . . ?
C2 N1 C1 117.86(11) . . ?
C1 N2 C8 116.84(11) . . ?
N2 C1 N1 125.98(12) . . ?
N2 C1 C9 117.64(12) . . ?
N1 C1 C9 116.37(11) . . ?
N1 C2 C3 121.68(12) . . ?
N1 C2 C16 114.57(11) . . ?
C3 C2 C16 123.75(12) . . ?
C4 C3 C8 118.70(12) . . ?
C4 C3 C2 125.80(12) . . ?
C8 C3 C2 115.48(12) . . ?
C5 C4 C3 120.31(12) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.48(13) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C7 C6 C5 120.83(12) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C8 119.88(12) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
N2 C8 C7 118.28(12) . . ?
N2 C8 C3 121.97(12) . . ?
C7 C8 C3 119.74(12) . . ?
C14 C9 C10 118.10(12) . . ?
C14 C9 C1 121.93(12) . . ?
C10 C9 C1 119.97(12) . . ?
C11 C10 C9 121.45(12) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C10 C11 C12 119.74(12) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
O1 C12 C13 124.63(12) . . ?
O1 C12 C11 115.55(12) . . ?
C13 C12 C11 119.82(12) . . ?
C14 C13 C12 119.72(12) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 121.16(12) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
O1 C15 H15A 109.5 . . ?
O1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 118.82(12) . . ?
C21 C16 C2 122.38(12) . . ?
C17 C16 C2 118.76(12) . . ?
C18 C17 C16 120.52(13) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 120.00(13) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 120.05(13) . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C19 C20 C21 120.15(13) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 120.44(13) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
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 C12 1.3642(16) . ?
O1 C15 1.4311(16) . ?
N1 C2 1.3224(17) . ?
N1 C1 1.3676(17) . ?
N2 C1 1.3174(17) . ?
N2 C8 1.3658(17) . ?
C1 C9 1.4803(18) . ?
C2 C3 1.4301(18) . ?
C2 C16 1.4919(18) . ?
C3 C4 1.4173(18) . ?
C3 C8 1.4199(19) . ?
C4 C5 1.3701(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.408(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.3650(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.4148(18) . ?
C7 H7 0.9500 . ?
C9 C14 1.3929(18) . ?
C9 C10 1.4017(19) . ?
C10 C11 1.3772(19) . ?
C10 H10 0.9500 . ?
C11 C12 1.3972(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.3926(19) . ?
C13 C14 1.3902(18) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.3956(19) . ?
C16 C17 1.3994(19) . ?
C17 C18 1.3846(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
