#------------------------------------------------------------------------------
#$Date: 2019-11-08 02:54:10 +0200 (Fri, 08 Nov 2019) $
#$Revision: 224899 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/85/7058591.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_7058591
loop_
_publ_author_name
'Arendt-Pindel, Agata'
'Marszałek-Harych, Aleksandra'
'Gębarowska, Elżbieta'
'Gębarowski, Tomasz'
'Jędrzkiewicz, Dawid'
'Pląskowska, Elżbieta'
'Zalewski, Dariusz'
'Gulia, Nurbey'
'Szafert, Sławomir'
'Ejfler, Jolanta'
_publ_section_title
;
 Design and functionalization of bioactive benzoxazines. An unexpected
 ortho-substitution effect
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              12042
_journal_paper_doi               10.1039/C8NJ06440G
_journal_volume                  43
_journal_year                    2019
_chemical_formula_moiety         'C20 H24 Br N O'
_chemical_formula_sum            'C20 H24 Br N O'
_chemical_formula_weight         374.31
_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
;
2018-08-06 deposited with the CCDC.    2019-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.65(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.652(5)
_cell_length_b                   8.838(3)
_cell_length_c                   11.184(3)
_cell_measurement_reflns_used    7795
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.9929
_cell_measurement_theta_min      2.8038
_cell_volume                     1736.3(9)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3359
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18215
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        25.500
_diffrn_reflns_theta_max         31.062
_diffrn_reflns_theta_min         2.943
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.372
_exptl_absorpt_correction_T_max  0.878
_exptl_absorpt_correction_T_min  0.488
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
            model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         5373
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.913
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0367
_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)+(0.0486P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0871
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3665
_reflns_number_total             5373
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8nj06440g2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 7058586--7058596.cif.'
_cod_database_code               7058591
_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   0.589
_shelx_estimated_absorpt_t_max   0.871
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 0.28594(2) 0.61228(2) 0.55910(2) 0.02452(7) Uani 1 1 d . .
O1 O 0.75971(7) 0.89956(16) 0.37594(12) 0.0200(3) Uani 1 1 d . .
N1 N 0.66237(9) 0.87170(18) 0.20998(15) 0.0172(3) Uani 1 1 d . .
C1 C 0.36952(11) 0.7035(2) 0.49132(17) 0.0184(4) Uani 1 1 d . .
C2 C 0.44301(11) 0.6614(2) 0.53177(19) 0.0225(4) Uani 1 1 d . .
H2 H 0.4518 0.5863 0.5923 0.027 Uiso 1 1 calc R U
C3 C 0.50389(11) 0.7295(2) 0.48347(18) 0.0217(4) Uani 1 1 d . .
H3 H 0.5543 0.7006 0.5116 0.026 Uiso 1 1 calc R U
C4 C 0.49234(10) 0.8395(2) 0.39448(17) 0.0173(4) Uani 1 1 d . .
C5 C 0.41784(11) 0.8781(2) 0.35422(17) 0.0185(4) Uani 1 1 d . .
H5 H 0.4089 0.9519 0.2927 0.022 Uiso 1 1 calc R U
C6 C 0.35604(11) 0.8111(2) 0.40196(18) 0.0207(4) Uani 1 1 d . .
H6 H 0.3055 0.8389 0.3736 0.025 Uiso 1 1 calc R U
C7 C 0.55928(11) 0.9135(2) 0.34255(19) 0.0200(4) Uani 1 1 d . .
H7A H 0.5911 0.9662 0.4075 0.024 Uiso 1 1 calc R U
H7B H 0.5402 0.9901 0.2824 0.024 Uiso 1 1 calc R U
C8 C 0.60818(11) 0.7986(2) 0.28316(18) 0.0182(4) Uani 1 1 d . .
H8A H 0.6366 0.7364 0.3461 0.022 Uiso 1 1 calc R U
H8B H 0.5747 0.7302 0.2316 0.022 Uiso 1 1 calc R U
C9 C 0.71391(11) 0.9727(2) 0.27685(18) 0.0202(4) Uani 1 1 d . .
H9A H 0.6844 1.0559 0.3092 0.024 Uiso 1 1 calc R U
H9B H 0.7483 1.0180 0.2218 0.024 Uiso 1 1 calc R U
C10 C 0.79563(10) 0.7704(2) 0.34061(18) 0.0176(4) Uani 1 1 d . .
C11 C 0.85386(11) 0.7105(2) 0.41859(18) 0.0190(4) Uani 1 1 d . .
H11 H 0.8673 0.7568 0.4944 0.023 Uiso 1 1 calc R U
C12 C 0.89246(11) 0.5828(2) 0.38550(17) 0.0185(4) Uani 1 1 d . .
H12 H 0.9317 0.5418 0.4403 0.022 Uiso 1 1 calc R U
C13 C 0.87549(10) 0.5127(2) 0.27418(17) 0.0153(4) Uani 1 1 d . .
C14 C 0.81474(10) 0.5731(2) 0.19935(17) 0.0156(4) Uani 1 1 d . .
H14 H 0.8007 0.5261 0.1240 0.019 Uiso 1 1 calc R U
C15 C 0.77409(10) 0.6992(2) 0.23094(17) 0.0156(4) Uani 1 1 d . .
C16 C 0.70755(11) 0.7610(2) 0.14827(18) 0.0182(4) Uani 1 1 d . .
H16A H 0.7272 0.8100 0.0780 0.022 Uiso 1 1 calc R U
H16B H 0.6743 0.6761 0.1185 0.022 Uiso 1 1 calc R U
C17 C 0.91968(11) 0.3761(2) 0.23394(18) 0.0188(4) Uani 1 1 d . .
C18 C 0.99162(11) 0.3444(3) 0.3172(2) 0.0268(5) Uani 1 1 d . .
H18A H 1.0238 0.4350 0.3231 0.040 Uiso 1 1 calc R U
H18B H 1.0196 0.2605 0.2848 0.040 Uiso 1 1 calc R U
H18C H 0.9777 0.3174 0.3971 0.040 Uiso 1 1 calc R U
C19 C 0.86884(13) 0.2350(3) 0.2308(3) 0.0381(6) Uani 1 1 d . .
H19A H 0.8535 0.2158 0.3114 0.057 Uiso 1 1 calc R U
H19B H 0.8971 0.1476 0.2046 0.057 Uiso 1 1 calc R U
H19C H 0.8234 0.2516 0.1746 0.057 Uiso 1 1 calc R U
C20 C 0.94463(15) 0.4062(3) 0.1083(2) 0.0361(6) Uani 1 1 d . .
H20A H 0.8996 0.4221 0.0512 0.054 Uiso 1 1 calc R U
H20B H 0.9734 0.3190 0.0828 0.054 Uiso 1 1 calc R U
H20C H 0.9769 0.4966 0.1108 0.054 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'
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
C10 O1 C9 112.64(15)
C9 N1 C8 113.48(16)
C9 N1 C16 108.24(15)
C8 N1 C16 112.37(15)
C2 C1 C6 120.70(18)
C2 C1 Br1 119.69(16)
C6 C1 Br1 119.61(14)
C1 C2 C3 119.61(19)
C1 C2 H2 120.2
C3 C2 H2 120.2
C2 C3 C4 121.14(19)
C2 C3 H3 119.4
C4 C3 H3 119.4
C5 C4 C3 118.06(18)
C5 C4 C7 121.23(18)
C3 C4 C7 120.70(18)
C4 C5 C6 121.54(19)
C4 C5 H5 119.2
C6 C5 H5 119.2
C1 C6 C5 118.93(18)
C1 C6 H6 120.5
C5 C6 H6 120.5
C4 C7 C8 112.07(16)
C4 C7 H7A 109.2
C8 C7 H7A 109.2
C4 C7 H7B 109.2
C8 C7 H7B 109.2
H7A C7 H7B 107.9
N1 C8 C7 112.17(16)
N1 C8 H8A 109.2
C7 C8 H8A 109.2
N1 C8 H8B 109.2
C7 C8 H8B 109.2
H8A C8 H8B 107.9
N1 C9 O1 113.38(16)
N1 C9 H9A 108.9
O1 C9 H9A 108.9
N1 C9 H9B 108.9
O1 C9 H9B 108.9
H9A C9 H9B 107.7
O1 C10 C11 117.90(17)
O1 C10 C15 121.99(17)
C11 C10 C15 120.10(18)
C10 C11 C12 119.73(18)
C10 C11 H11 120.1
C12 C11 H11 120.1
C11 C12 C13 122.07(18)
C11 C12 H12 119.0
C13 C12 H12 119.0
C12 C13 C14 116.63(17)
C12 C13 C17 122.81(17)
C14 C13 C17 120.56(17)
C15 C14 C13 122.57(18)
C15 C14 H14 118.7
C13 C14 H14 118.7
C14 C15 C10 118.78(17)
C14 C15 C16 121.33(17)
C10 C15 C16 119.89(17)
N1 C16 C15 111.95(16)
N1 C16 H16A 109.2
C15 C16 H16A 109.2
N1 C16 H16B 109.2
C15 C16 H16B 109.2
H16A C16 H16B 107.9
C18 C17 C13 112.56(17)
C18 C17 C19 108.35(18)
C13 C17 C19 109.50(17)
C18 C17 C20 107.07(18)
C13 C17 C20 109.44(17)
C19 C17 C20 109.9(2)
C17 C18 H18A 109.5
C17 C18 H18B 109.5
H18A C18 H18B 109.5
C17 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
C17 C19 H19A 109.5
C17 C19 H19B 109.5
H19A C19 H19B 109.5
C17 C19 H19C 109.5
H19A C19 H19C 109.5
H19B C19 H19C 109.5
C17 C20 H20A 109.5
C17 C20 H20B 109.5
H20A C20 H20B 109.5
C17 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.903(2)
O1 C10 1.383(2)
O1 C9 1.457(2)
N1 C9 1.432(3)
N1 C8 1.468(2)
N1 C16 1.476(2)
C1 C2 1.382(3)
C1 C6 1.383(3)
C2 C3 1.387(3)
C2 H2 0.9500
C3 C4 1.392(3)
C3 H3 0.9500
C4 C5 1.390(3)
C4 C7 1.515(3)
C5 C6 1.393(3)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.526(3)
C7 H7A 0.9900
C7 H7B 0.9900
C8 H8A 0.9900
C8 H8B 0.9900
C9 H9A 0.9900
C9 H9B 0.9900
C10 C11 1.386(3)
C10 C15 1.397(3)
C11 C12 1.388(3)
C11 H11 0.9500
C12 C13 1.397(3)
C12 H12 0.9500
C13 C14 1.400(3)
C13 C17 1.529(3)
C14 C15 1.390(3)
C14 H14 0.9500
C15 C16 1.523(3)
C16 H16A 0.9900
C16 H16B 0.9900
C17 C18 1.525(3)
C17 C19 1.534(3)
C17 C20 1.536(3)
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
C19 H19A 0.9800
C19 H19B 0.9800
C19 H19C 0.9800
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
