#------------------------------------------------------------------------------
#$Date: 2019-11-17 14:52:13 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230636 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/63/7156339.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_7156339
loop_
_publ_author_name
'Jiang, Wang'
'Sun, Jing'
'Liu, Ru-Zhang'
'Yan, Chao-Guo'
_publ_section_title
;
 Molecular diversity of the domino annulation reaction of
 2-aryl-3-nitrochromenes with pivaloylacetonitriles.
;
_journal_issue                   32
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              5816
_journal_page_last               5822
_journal_paper_doi               10.1039/c8ob01504j
_journal_volume                  16
_journal_year                    2018
_chemical_formula_moiety         'C25 H16 Br N O2'
_chemical_formula_sum            'C25 H16 Br N O2'
_chemical_formula_weight         442.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-06-12 deposited with the CCDC.
2018-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.226(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.3424(18)
_cell_length_b                   19.837(6)
_cell_length_c                   19.534(6)
_cell_measurement_reflns_used    2429
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      19.41
_cell_measurement_theta_min      2.32
_cell_volume                     2015.2(11)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1112
_diffrn_reflns_av_unetI/netI     0.1414
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            17985
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_min         2.375
_exptl_absorpt_coefficient_mu    2.061
_exptl_absorpt_correction_T_max  0.662
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.2514
_refine_ls_R_factor_gt           0.0778
_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)+(0.0524P)²+2.7711P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1415
_refine_ls_wR_factor_ref         0.1961
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1354
_reflns_number_total             3949
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ob01504j2.cif
_cod_data_source_block           5f
_cod_depositor_comments
'Adding full bibliography for 7156337--7156344.cif.'
_cod_database_code               7156339
_shelx_shelxl_version_number     2014/7
_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   0.638
_shelx_estimated_absorpt_t_max   0.683
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Br1 Br 1.4730(2) 1.25310(5) 0.26571(6) 0.1375(5) Uani 1 1 d . .
C1 C 0.2349(16) 0.9044(4) 0.3056(4) 0.094(2) Uani 1 1 d . .
H1 H 0.2411 0.8846 0.2629 0.113 Uiso 1 1 calc R U
C2 C 0.0792(16) 0.8763(4) 0.3458(5) 0.114(3) Uani 1 1 d . .
H2 H -0.0191 0.8384 0.3299 0.137 Uiso 1 1 calc R U
C3 C 0.0707(16) 0.9050(5) 0.4095(5) 0.104(3) Uani 1 1 d . .
H3 H -0.0306 0.8860 0.4374 0.124 Uiso 1 1 calc R U
C4 C 0.2097(16) 0.9606(5) 0.4311(4) 0.103(3) Uani 1 1 d . .
H4 H 0.2043 0.9797 0.4742 0.124 Uiso 1 1 calc R U
C5 C 0.3606(13) 0.9899(4) 0.3905(3) 0.089(2) Uani 1 1 d . .
H5 H 0.4495 1.0295 0.4056 0.107 Uiso 1 1 calc R U
C6 C 0.3806(13) 0.9607(4) 0.3274(3) 0.0687(18) Uani 1 1 d . .
C7 C 0.5377(13) 0.9907(4) 0.2843(3) 0.0651(18) Uani 1 1 d . .
C8 C 0.7129(13) 1.0421(4) 0.2938(3) 0.0625(17) Uani 1 1 d . .
C9 C 0.7845(15) 1.0841(4) 0.3528(4) 0.085(2) Uani 1 1 d . .
C10 C 0.4435(19) 0.8957(6) 0.0429(5) 0.102(3) Uani 1 1 d . .
H10 H 0.3084 0.9258 0.0286 0.122 Uiso 1 1 calc R U
C11 C 0.4160(18) 0.8295(8) 0.0196(4) 0.107(3) Uani 1 1 d . .
H11 H 0.2623 0.8149 -0.0093 0.129 Uiso 1 1 calc R U
C12 C 0.621(3) 0.7857(5) 0.0398(5) 0.091(2) Uani 1 1 d . .
C13 C 0.585(2) 0.7144(5) 0.0125(5) 0.156(4) Uani 1 1 d . .
H13A H 0.7388 0.6995 -0.0003 0.234 Uiso 1 1 calc R U
H13B H 0.4437 0.7128 -0.0279 0.234 Uiso 1 1 calc R U
H13C H 0.5491 0.6854 0.0485 0.234 Uiso 1 1 calc R U
C14 C 0.8411(18) 0.8078(6) 0.0812(5) 0.097(2) Uani 1 1 d . .
H14 H 0.9804 0.7787 0.0940 0.117 Uiso 1 1 calc R U
C15 C 0.8618(17) 0.8730(6) 0.1046(4) 0.101(3) Uani 1 1 d . .
H15 H 1.0153 0.8874 0.1337 0.121 Uiso 1 1 calc R U
C16 C 0.665(2) 0.9169(4) 0.0864(4) 0.085(2) Uani 1 1 d . .
C17 C 0.6924(16) 0.9901(5) 0.1121(3) 0.102(3) Uani 1 1 d . .
H17 H 0.5515 1.0165 0.0835 0.122 Uiso 1 1 calc R U
C18 C 0.6857(15) 0.9986(4) 0.1893(3) 0.081(2) Uani 1 1 d . .
C19 C 0.8103(13) 1.0468(4) 0.2307(3) 0.0658(18) Uani 1 1 d . .
C20 C 0.9897(13) 1.0895(4) 0.2060(3) 0.0708(18) Uani 1 1 d . .
C21 C 1.1175(14) 1.1442(4) 0.2419(4) 0.081(2) Uani 1 1 d . .
H21 H 1.0882 1.1563 0.2854 0.098 Uiso 1 1 calc R U
C22 C 1.2876(15) 1.1806(3) 0.2134(4) 0.090(2) Uani 1 1 d . .
C23 C 1.3247(16) 1.1654(5) 0.1478(5) 0.097(2) Uani 1 1 d . .
H23 H 1.4363 1.1913 0.1284 0.116 Uiso 1 1 calc R U
C24 C 1.1981(16) 1.1125(5) 0.1112(4) 0.094(2) Uani 1 1 d . .
H24 H 1.2223 1.1024 0.0667 0.113 Uiso 1 1 calc R U
C25 C 1.0337(14) 1.0738(4) 0.1401(4) 0.077(2) Uani 1 1 d . .
N1 N 0.8462(15) 1.1185(4) 0.4010(4) 0.126(3) Uani 1 1 d . .
O1 O 0.5200(8) 0.9630(2) 0.2187(2) 0.0871(14) Uani 1 1 d . .
O2 O 0.9312(10) 1.0177(3) 0.1034(2) 0.0895(15) Uani 1 1 d . .
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'
Br Br -0.2901 2.4595 '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
C6 C1 C2 121.6(7)
C6 C1 H1 119.2
C2 C1 H1 119.2
C3 C2 C1 119.6(8)
C3 C2 H2 120.2
C1 C2 H2 120.2
C4 C3 C2 119.4(8)
C4 C3 H3 120.3
C2 C3 H3 120.3
C3 C4 C5 121.3(8)
C3 C4 H4 119.3
C5 C4 H4 119.3
C4 C5 C6 120.5(7)
C4 C5 H5 119.7
C6 C5 H5 119.7
C1 C6 C5 117.5(7)
C1 C6 C7 121.2(6)
C5 C6 C7 121.3(7)
C8 C7 O1 108.9(5)
C8 C7 C6 134.3(6)
O1 C7 C6 116.8(7)
C7 C8 C9 127.1(6)
C7 C8 C19 107.5(6)
C9 C8 C19 125.3(7)
N1 C9 C8 179.2(8)
C16 C10 C11 120.8(9)
C16 C10 H10 119.6
C11 C10 H10 119.6
C12 C11 C10 118.9(8)
C12 C11 H11 120.5
C10 C11 H11 120.5
C14 C12 C11 119.7(8)
C14 C12 C13 122.9(12)
C11 C12 C13 117.4(12)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 C15 120.3(8)
C12 C14 H14 119.9
C15 C14 H14 119.9
C16 C15 C14 121.6(9)
C16 C15 H15 119.2
C14 C15 H15 119.2
C15 C16 C10 118.6(9)
C15 C16 C17 121.0(11)
C10 C16 C17 120.3(10)
O2 C17 C18 107.3(6)
O2 C17 C16 110.1(6)
C18 C17 C16 114.0(7)
O2 C17 H17 108.4
C18 C17 H17 108.4
C16 C17 H17 108.4
C19 C18 O1 113.6(6)
C19 C18 C17 124.0(7)
O1 C18 C17 121.7(8)
C18 C19 C20 119.9(6)
C18 C19 C8 104.2(6)
C20 C19 C8 136.0(7)
C21 C20 C25 118.2(7)
C21 C20 C19 125.5(6)
C25 C20 C19 116.3(7)
C22 C21 C20 120.2(7)
C22 C21 H21 119.9
C20 C21 H21 119.9
C23 C22 C21 120.8(8)
C23 C22 Br1 119.9(7)
C21 C22 Br1 119.3(6)
C24 C23 C22 119.9(8)
C24 C23 H23 120.0
C22 C23 H23 120.0
C23 C24 C25 120.1(7)
C23 C24 H24 120.0
C25 C24 H24 120.0
O2 C25 C24 117.0(7)
O2 C25 C20 122.2(7)
C24 C25 C20 120.7(8)
C18 O1 C7 105.8(6)
C25 O2 C17 120.5(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C22 1.905(8)
C1 C6 1.373(9)
C1 C2 1.384(9)
C1 H1 0.9300
C2 C3 1.380(10)
C2 H2 0.9300
C3 C4 1.342(10)
C3 H3 0.9300
C4 C5 1.381(9)
C4 H4 0.9300
C5 C6 1.388(8)
C5 H5 0.9300
C6 C7 1.447(8)
C7 C8 1.367(8)
C7 O1 1.377(7)
C8 C9 1.403(10)
C8 C19 1.447(7)
C9 N1 1.147(9)
C10 C16 1.355(10)
C10 C11 1.385(11)
C10 H10 0.9300
C11 C12 1.383(11)
C11 H11 0.9300
C12 C14 1.340(10)
C12 C13 1.509(12)
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 C15 1.366(10)
C14 H14 0.9300
C15 C16 1.350(10)
C15 H15 0.9300
C16 C17 1.531(10)
C17 O2 1.434(8)
C17 C18 1.525(9)
C17 H17 0.9800
C18 C19 1.329(8)
C18 O1 1.359(7)
C19 C20 1.441(9)
C20 C21 1.384(9)
C20 C25 1.396(8)
C21 C22 1.375(9)
C21 H21 0.9300
C22 C23 1.374(9)
C23 C24 1.360(10)
C23 H23 0.9300
C24 C25 1.380(9)
C24 H24 0.9300
C25 O2 1.370(8)
