#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:38:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180309 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/23/7152386.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_7152386
loop_
_publ_author_name
'Shiva Kumar, K.'
'Rambabu, D.'
'Prasad, Bagineni'
'Mujahid, Mohammad'
'Krishna, G. Rama'
'Basaveswara Rao, M. V.'
'Malla Reddy, C.'
'Vanaja, G. R.'
'Kalle, Arunasree M.'
'Pal, Manojit'
_publ_section_title
;
 A new approach to construct a fused 2-ylidene chromene ring: highly
 regioselective synthesis of novel chromeno quinoxalines.
;
_journal_issue                   24
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4774
_journal_page_last               4781
_journal_paper_doi               10.1039/c2ob25416f
_journal_volume                  10
_journal_year                    2012
_chemical_formula_sum            'C21 H20 N2 O2'
_chemical_formula_weight         332.15
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.361(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   19.497(2)
_cell_length_b                   5.5899(7)
_cell_length_c                   16.139(2)
_cell_measurement_temperature    273(2)
_cell_volume                     1687.7(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17443
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.09
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.093
_refine_ls_extinction_coef       0.0051(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         4075
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0579
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0975P)²+1.0814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1549
_refine_ls_wR_factor_ref         0.1905
_reflns_number_gt                2670
_reflns_number_total             4075
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25416f.txt
_cod_data_source_block           drb_11_a
_cod_original_cell_volume        1687.6(4)
_cod_database_code               7152386
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.69850(8) 1.1910(3) 0.99750(10) 0.0189(4) Uani 1 1 d .
N2 N 0.61301(9) 1.1101(3) 0.82607(10) 0.0190(4) Uani 1 1 d .
O1 O 0.79011(8) 0.6794(3) 0.93445(9) 0.0261(4) Uani 1 1 d .
O2 O 0.75085(9) 0.2238(3) 0.68010(9) 0.0282(4) Uani 1 1 d .
H2 H 0.7337 0.2426 0.6280 0.042 Uiso 1 1 calc R
C8 C 0.68862(10) 0.7815(4) 0.81333(12) 0.0187(4) Uani 1 1 d .
C7 C 0.66958(10) 0.9763(4) 0.86221(11) 0.0178(4) Uani 1 1 d .
C15 C 0.71314(10) 1.0175(4) 0.94923(11) 0.0183(4) Uani 1 1 d .
C1 C 0.64065(10) 1.3345(4) 0.96059(12) 0.0186(4) Uani 1 1 d .
C16 C 0.77679(10) 0.8654(4) 0.98522(12) 0.0186(4) Uani 1 1 d .
C12 C 0.77014(11) 0.4493(4) 0.80826(12) 0.0222(4) Uani 1 1 d .
C14 C 0.74792(10) 0.6383(4) 0.85117(12) 0.0199(4) Uani 1 1 d .
C5 C 0.53845(10) 1.4436(4) 0.83875(12) 0.0211(4) Uani 1 1 d .
H5 H 0.5102 1.4182 0.7825 0.025 Uiso 1 1 calc R
C6 C 0.59781(10) 1.2925(4) 0.87450(12) 0.0181(4) Uani 1 1 d .
C2 C 0.62325(11) 1.5255(4) 1.00823(12) 0.0225(5) Uani 1 1 d .
H2A H 0.6512 1.5548 1.0643 0.027 Uiso 1 1 calc R
C9 C 0.64933(11) 0.7282(4) 0.72817(12) 0.0212(4) Uani 1 1 d .
H9 H 0.6094 0.8198 0.7014 0.025 Uiso 1 1 calc R
C4 C 0.52243(11) 1.6260(4) 0.88639(13) 0.0228(5) Uani 1 1 d .
H4 H 0.4832 1.7235 0.8625 0.027 Uiso 1 1 calc R
C10 C 0.66896(11) 0.5425(4) 0.68371(12) 0.0227(5) Uani 1 1 d .
H10 H 0.6421 0.5081 0.6276 0.027 Uiso 1 1 calc R
C17 C 0.82348(11) 0.9000(4) 1.06257(13) 0.0233(5) Uani 1 1 d .
H17 H 0.8115 1.0191 1.0962 0.028 Uiso 1 1 calc R
C11 C 0.72939(11) 0.4056(4) 0.72311(12) 0.0222(5) Uani 1 1 d .
C13 C 0.83618(12) 0.3038(5) 0.85029(14) 0.0320(6) Uani 1 1 d .
H13A H 0.8780 0.3984 0.8541 0.048 Uiso 1 1 calc R
H13B H 0.8371 0.1636 0.8163 0.048 Uiso 1 1 calc R
H13C H 0.8353 0.2570 0.9072 0.048 Uiso 1 1 calc R
C18 C 0.89358(12) 0.7709(4) 1.10299(14) 0.0268(5) Uani 1 1 d .
C3 C 0.56520(11) 1.6679(4) 0.97197(13) 0.0240(5) Uani 1 1 d .
H3 H 0.5538 1.7929 1.0038 0.029 Uiso 1 1 calc R
C21 C 0.88570(14) 0.5015(4) 1.10430(16) 0.0351(6) Uani 1 1 d .
H21A H 0.8535 0.4599 1.1373 0.053 Uiso 1 1 calc R
H21B H 0.9315 0.4302 1.1301 0.053 Uiso 1 1 calc R
H21C H 0.8671 0.4436 1.0463 0.053 Uiso 1 1 calc R
C19 C 0.92087(16) 0.8555(5) 1.19770(18) 0.0522(9) Uani 1 1 d .
H19A H 0.9234 1.0271 1.1993 0.078 Uiso 1 1 calc R
H19B H 0.9675 0.7902 1.2235 0.078 Uiso 1 1 calc R
H19C H 0.8886 0.8020 1.2291 0.078 Uiso 1 1 calc R
C20 C 0.94635(14) 0.8389(6) 1.0534(2) 0.0540(9) Uani 1 1 d .
H20A H 0.9300 0.7774 0.9957 0.081 Uiso 1 1 calc R
H20B H 0.9924 0.7723 1.0818 0.081 Uiso 1 1 calc R
H20C H 0.9500 1.0100 1.0516 0.081 Uiso 1 1 calc R
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
C15 N1 C1 117.30(16)
C7 N2 C6 117.21(16)
C14 O1 C16 122.50(16)
C14 C8 C9 117.53(19)
C14 C8 C7 119.90(17)
C9 C8 C7 122.57(18)
N2 C7 C15 121.88(18)
N2 C7 C8 119.51(16)
C15 C7 C8 118.61(17)
N1 C15 C7 121.68(18)
N1 C15 C16 119.03(16)
C7 C15 C16 119.28(18)
N1 C1 C2 119.92(17)
N1 C1 C6 120.66(18)
C2 C1 C6 119.43(18)
C17 C16 O1 117.84(18)
C17 C16 C15 123.94(19)
O1 C16 C15 118.19(16)
C14 C12 C11 116.67(18)
C14 C12 C13 121.87(18)
C11 C12 C13 121.44(19)
O1 C14 C12 115.14(17)
O1 C14 C8 121.45(18)
C12 C14 C8 123.39(17)
C4 C5 C6 120.40(18)
N2 C6 C5 119.69(17)
N2 C6 C1 121.25(18)
C5 C6 C1 119.06(19)
C3 C2 C1 120.15(18)
C10 C9 C8 121.03(19)
C5 C4 C3 120.46(19)
C9 C10 C11 119.88(18)
C16 C17 C18 128.7(2)
O2 C11 C10 121.15(17)
O2 C11 C12 117.36(18)
C10 C11 C12 121.49(19)
C21 C18 C20 110.0(2)
C21 C18 C17 113.29(19)
C20 C18 C17 108.41(19)
C21 C18 C19 107.4(2)
C20 C18 C19 110.4(2)
C17 C18 C19 107.3(2)
C2 C3 C4 120.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C15 1.324(3)
N1 C1 1.376(3)
N2 C7 1.324(3)
N2 C6 1.367(3)
O1 C14 1.383(2)
O1 C16 1.393(2)
O2 C11 1.361(3)
C8 C14 1.397(3)
C8 C9 1.404(3)
C8 C7 1.453(3)
C7 C15 1.440(2)
C15 C16 1.481(3)
C1 C2 1.411(3)
C1 C6 1.425(3)
C16 C17 1.336(3)
C12 C14 1.397(3)
C12 C11 1.402(3)
C12 C13 1.513(3)
C5 C4 1.365(3)
C5 C6 1.418(3)
C2 C3 1.373(3)
C9 C10 1.376(3)
C4 C3 1.417(3)
C10 C11 1.399(3)
C17 C18 1.521(3)
C18 C21 1.515(3)
C18 C20 1.519(4)
C18 C19 1.544(3)
