#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:23:00 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/88/4028877.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_4028877
loop_
_publ_author_name
'Ram Tilak Naganaboina'
'Rama Krishna Peddinti'
_publ_contact_author_address
;     
Department of Chemistry, Indian Institute of Technology, Roorkee-247667,
Uttarakhand, India.
;
_publ_contact_author_email
'rkpedfcy@iitr.ernet.in, ramakpeddinti@gmail.com'
_publ_contact_author_fax         '+ (91) 133 227 3560'
_publ_contact_author_name        'Rama Krishna Peddinti'
_publ_contact_author_phone       '+(91) 133 228 5438'
_publ_section_title
;
 BF3.Etherate-Mediated Friedel-Crafts Arylation of
 2-Hydroxy-1,4-benzoxazines: Synthesis of 2-Aryl-1,4-benzoxazine
 Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              12819
_journal_page_last               12824
_journal_paper_doi               10.1021/jo402254n
_journal_volume                  78
_journal_year                    2013
_chemical_formula_moiety         'C20 H19 Cl N O6'
_chemical_formula_sum            'C20 H19 Cl N O6'
_chemical_formula_weight         404.81
_chemical_name_systematic
;
 ?
;
_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-2013
_cell_angle_alpha                90
_cell_angle_beta                 100.1020(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.8408(4)
_cell_length_b                   18.4917(7)
_cell_length_c                   9.6835(4)
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.372
_cell_volume                     1911.11(13)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0311
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            33196
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.908
_exptl_absorpt_coefficient_mu    0.237
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             844.0
_refine_diff_density_max         0.632
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.275
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3909
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.263
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0456
_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)+(0.1000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1491
_refine_ls_wR_factor_ref         0.1574
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3290
_reflns_number_total             3909
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo402254n_si_002.cif
_cod_data_source_block           datam_a
_cod_database_code               4028877
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelxl_version_number           2013-2
#END Tags that were not found in dictionaries
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
Cl1 Cl 0.84690(5) 0.79101(2) 0.62752(5) 0.0592(2) Uani 1 1 d . U
O4 O 0.66176(12) 0.49385(6) 0.64273(12) 0.0473(3) Uani 1 1 d . U
O3 O 0.52563(11) 0.42772(6) 0.84559(14) 0.0504(3) Uani 1 1 d . U
O5 O 0.89737(12) 0.53287(6) 1.15130(12) 0.0496(3) Uani 1 1 d . U
O6 O 0.88489(13) 0.41974(7) 1.23094(12) 0.0499(3) Uani 1 1 d . U
O2 O 0.83129(12) 0.32438(7) 0.62379(15) 0.0546(4) Uani 1 1 d . U
N1 N 0.80955(13) 0.55145(7) 0.87567(13) 0.0391(3) Uani 1 1 d . U
O1 O 0.51180(12) 0.17494(7) 0.7672(2) 0.0728(5) Uani 1 1 d . U
C4 C 0.67888(14) 0.37420(8) 0.73755(16) 0.0359(4) Uani 1 1 d . U
C9 C 0.78311(15) 0.59223(8) 0.75357(16) 0.0350(4) Uani 1 1 d . U
C8 C 0.78869(13) 0.47885(8) 0.87691(15) 0.0320(3) Uani 1 1 d . U
C14 C 0.82561(15) 0.66261(9) 0.74909(17) 0.0397(4) Uani 1 1 d . U
H14 H 0.8751 0.6832 0.8274 0.048 Uiso 1 1 calc R U
C15 C 0.81728(14) 0.43887(8) 0.99513(16) 0.0359(4) Uani 1 1 d . U
H15 H 0.8023 0.3893 0.9898 0.043 Uiso 1 1 calc R U
C16 C 0.86982(14) 0.46974(9) 1.12832(16) 0.0369(4) Uani 1 1 d . U
C3 C 0.72811(15) 0.31304(9) 0.68384(18) 0.0385(4) Uani 1 1 d . U
C5 C 0.57111(14) 0.36602(8) 0.79683(17) 0.0382(4) Uani 1 1 d . U
C7 C 0.74390(14) 0.44588(8) 0.73451(16) 0.0361(4) Uani 1 1 d . U
H7 H 0.8180 0.4377 0.6914 0.043 Uiso 1 1 calc R U
C10 C 0.70941(16) 0.56245(9) 0.63497(17) 0.0404(4) Uani 1 1 d . U
C6 C 0.51685(15) 0.29876(9) 0.8063(2) 0.0437(4) Uani 1 1 d . U
H6 H 0.4455 0.2939 0.8466 0.052 Uiso 1 1 calc R U
C2 C 0.67562(16) 0.24507(9) 0.6927(2) 0.0461(4) Uani 1 1 d . U
H2 H 0.7105 0.2046 0.6576 0.055 Uiso 1 1 calc R U
C13 C 0.79364(17) 0.70188(9) 0.62706(19) 0.0442(4) Uani 1 1 d . U
C1 C 0.57090(15) 0.23868(9) 0.7545(2) 0.0467(4) Uani 1 1 d . U
C12 C 0.7205(2) 0.67338(11) 0.5100(2) 0.0570(5) Uani 1 1 d . U
H12 H 0.6993 0.7008 0.4289 0.068 Uiso 1 1 calc R U
C11 C 0.6785(2) 0.60217(11) 0.5151(2) 0.0565(5) Uani 1 1 d . U
H11 H 0.6293 0.5817 0.4365 0.068 Uiso 1 1 calc R U
C17 C 0.9288(2) 0.44626(13) 1.37068(18) 0.0608(5) Uani 1 1 d . U
H17A H 1.0064 0.4717 1.3731 0.091 Uiso 1 1 calc R U
H17B H 0.9417 0.4063 1.4349 0.091 Uiso 1 1 calc R U
H17C H 0.8676 0.4785 1.3973 0.091 Uiso 1 1 calc R U
C19 C 0.8839(2) 0.26469(11) 0.5641(3) 0.0606(5) Uani 1 1 d . U
H19A H 0.9050 0.2277 0.6337 0.091 Uiso 1 1 calc R U
H19B H 0.9582 0.2798 0.5308 0.091 Uiso 1 1 calc R U
H19C H 0.8244 0.2460 0.4872 0.091 Uiso 1 1 calc R U
C18 C 0.4138(2) 0.42309(11) 0.9022(3) 0.0623(6) Uani 1 1 d . U
H18A H 0.3460 0.4083 0.8302 0.093 Uiso 1 1 calc R U
H18B H 0.3952 0.4695 0.9379 0.093 Uiso 1 1 calc R U
H18C H 0.4245 0.3883 0.9769 0.093 Uiso 1 1 calc R U
C20 C 0.5827(2) 0.11157(11) 0.7755(4) 0.0880(9) Uani 1 1 d . U
H20A H 0.6127 0.1043 0.6889 0.132 Uiso 1 1 calc R U
H20B H 0.5315 0.0712 0.7922 0.132 Uiso 1 1 calc R U
H20C H 0.6526 0.1155 0.8511 0.132 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'
Cl Cl 0.1484 0.1585 '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 O4 C7 113.71(12)
C5 O3 C18 118.05(13)
C16 O6 C17 115.93(14)
C3 O2 C19 118.34(14)
C8 N1 C9 122.19(13)
C1 O1 C20 118.06(15)
C3 C4 C5 117.98(14)
C3 C4 C7 119.86(14)
C5 C4 C7 122.13(13)
C14 C9 N1 121.13(14)
C14 C9 C10 119.48(14)
N1 C9 C10 119.36(14)
C15 C8 N1 122.18(13)
C15 C8 C7 122.84(13)
N1 C8 C7 114.70(13)
C13 C14 C9 119.16(15)
C8 C15 C16 122.66(13)
O5 C16 O6 122.02(14)
O5 C16 C15 126.37(15)
O6 C16 C15 111.60(13)
O2 C3 C2 122.76(14)
O2 C3 C4 115.58(14)
C2 C3 C4 121.66(15)
O3 C5 C6 123.11(15)
O3 C5 C4 115.59(13)
C6 C5 C4 121.29(14)
O4 C7 C4 108.20(12)
O4 C7 C8 112.25(12)
C4 C7 C8 114.54(12)
C11 C10 O4 120.25(15)
C11 C10 C9 120.56(16)
O4 C10 C9 119.07(14)
C5 C6 C1 118.87(15)
C1 C2 C3 118.84(15)
C12 C13 C14 121.92(16)
C12 C13 Cl1 120.57(14)
C14 C13 Cl1 117.50(14)
O1 C1 C2 123.48(15)
O1 C1 C6 115.20(15)
C2 C1 C6 121.31(15)
C13 C12 C11 118.59(17)
C10 C11 C12 120.29(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C13 1.7461(17)
O4 C10 1.377(2)
O4 C7 1.4463(19)
O3 C5 1.3600(19)
O3 C18 1.418(2)
O5 C16 1.216(2)
O6 C16 1.3462(19)
O6 C17 1.440(2)
O2 C3 1.364(2)
O2 C19 1.412(2)
N1 C8 1.3618(19)
N1 C9 1.389(2)
O1 C1 1.357(2)
O1 C20 1.396(3)
C4 C3 1.390(2)
C4 C5 1.397(2)
C4 C7 1.504(2)
C9 C14 1.384(2)
C9 C10 1.392(2)
C8 C15 1.352(2)
C8 C7 1.508(2)
C14 C13 1.378(2)
C15 C16 1.434(2)
C3 C2 1.389(2)
C5 C6 1.386(2)
C10 C11 1.365(2)
C6 C1 1.390(2)
C2 C1 1.378(3)
C13 C12 1.369(3)
C12 C11 1.397(3)
