Substrate Directed C-H Activation for the Synthesis of Benzo[c]cinnolines through a Sequential C-C and C-N Bond Formation.
Reddy, B. V. Subba; Reddy, C. Ravikumar; Reddy, M. Rajashekhar; Yarlagadda, Suresh; Sridhar, B.; Organic letters 17 (2015) 3730–3733; doi:10.1021/acs.orglett.5b01717

data_1529873
_publ_section_title
;
 Substrate Directed C-H Activation for the Synthesis of Benzo[c]cinnolines
 through a Sequential C-C and C-N Bond Formation.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3730
_journal_page_last               3733
_journal_paper_doi               10.1021/acs.orglett.5b01717
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C20 H24 N2 O4'
_chemical_formula_sum            'C20 H24 N2 O4'
_chemical_formula_weight         356.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-23
_audit_creation_method
;
  Olex2 1.2
  (compiled Dec  5 2012 16:20:19, GUI svn.r4385)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.244(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.5233(13)
_cell_length_b                   7.6374(8)
_cell_length_c                   11.6452(13)
_cell_measurement_reflns_used    7074
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.67
_cell_volume                     961.56(18)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9906
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.247
_diffrn_reflns_theta_min         1.864
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; Bruker,2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.231
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 1580 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3841
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.152
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0601
_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/[\s^2^(Fo^2^)+(0.0974P)^2^+0.4626P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1826
_refine_ls_wR_factor_ref         0.1846
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    0.986
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                3678
_reflns_number_total             3841
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol5b01717_si_001.cif
_cod_data_source_block           ay68m
_cod_database_code               1529873
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.052) H5(0.056) H8(0.058) H9(0.066) H11(0.057) H12(0.05)
 H13A(0.083) H13B(0.083) H14A(0.116) H14B(0.116) H14C(0.116) H15A(0.11)
 H15B(0.11) H15C(0.11) H17A(0.093) H17B(0.093) H17C(0.093) H19A(0.146)
 H19B(0.146) H19C(0.146) H20A(0.105) H20B(0.105) H20C(0.105)
 Fixed X: H2(0.5948) H5(0.7533) H8(0.9309) H9(1.1355) H11(1.2047) H12(1.0002)
 H13A(1.3569) H13B(1.3751) H14A(1.3133) H14B(1.3345) H14C(1.4451) H15A(0.3927)
 H15B(0.3707) H15C(0.371) H17A(0.908) H17B(0.9803) H17C(0.8443) H19A(0.7371)
 H19B(0.6598) H19C(0.7862) H20A(0.4774) H20B(0.4433) H20C(0.5565)
 Fixed Y: H2(0.7287) H5(0.6099) H8(0.7945) H9(0.7692) H11(0.5133) H12(0.5328)
 H13A(0.5025) H13B(0.705) H14A(0.5303) H14B(0.7329) H14C(0.6036) H15A(0.7148)
 H15B(0.7724) H15C(0.5731) H17A(1.2193) H17B(1.1952) H17C(1.2664) H19A(0.6707)
 H19B(0.5033) H19C(0.4849) H20A(0.4858) H20B(0.685) H20C(0.6128)
 Fixed Z: H2(-0.0112) H5(0.4011) H8(0.4746) H9(0.5963) H11(0.3283) H12(0.2082)
 H13A(0.5367) H13B(0.5344) H14A(0.7164) H14B(0.7145) H14C(0.7328) H15A(-0.0194)
 H15B(0.1007) H15C(0.0685) H17A(0.0657) H17B(0.206) H17C(0.1607) H19A(-0.3664)
 H19B(-0.3626) H19C(-0.3842) H20A(0.3143) H20B(0.3092) H20C(0.4175)
;
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.987
_shelx_hkl_checksum              84195
_shelx_res_checksum              6802
_shelx_shelxl_version_number     2014/7