#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:03:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178800 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/54/4105477.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_4105477
loop_
_publ_author_name
'Danny C. Hsu'
'Polo C.-H. Lam'
'Carla Slebodnick'
'Paul R. Carlier'
_publ_section_title
;
 Complete Mapping of the Stereochemical Course of Retentive
 Deprotonation/Alkylation of 1H-Benzo[e][1,4]diazepin-2(3H)-ones
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              18168
_journal_page_last               18176
_journal_paper_doi               10.1021/ja907507j
_journal_volume                  131
_journal_year                    2009
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H19 N3 O'
_chemical_formula_sum            'C20 H19 N3 O'
_chemical_formula_weight         317.38
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 118.459(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.7624(5)
_cell_length_b                   7.9949(2)
_cell_length_c                   10.9354(4)
_cell_measurement_reflns_used    6509
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.49
_cell_measurement_theta_min      4.60
_cell_volume                     827.23(7)
_computing_cell_refinement       'CrysAlis (Oxford Diffraction)'
_computing_data_collection       'CrysAlis (Oxford Diffraction)'
_computing_data_reduction        'CrysAlis (Oxford Diffraction)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 4.1570
_diffrn_detector_type            'Oxford Diffraction Onyx CCD'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction PX Ultra'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4277
_diffrn_reflns_theta_full        66.81
_diffrn_reflns_theta_max         66.81
_diffrn_reflns_theta_min         4.60
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_source_current           40
_diffrn_source_voltage           40
_diffrn_standards_decay_%        <2%
_diffrn_standards_interval_count 50
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.632
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_description       rod
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.146
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         2754
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0338
_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)+(0.0555P)²+0.1534P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0900
_reflns_number_gt                2684
_reflns_number_total             2754
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja907507j_si_002.cif
_cod_data_source_block           cs857
_cod_original_cell_volume        827.23(5)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4105477
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
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
O1 O 0.60663(12) 0.13658(16) 0.22739(11) 0.0259(3) Uani 1 1 d .
N1 N 0.79897(14) 0.06673(17) 0.20626(13) 0.0198(3) Uani 1 1 d .
N2 N 0.65776(13) 0.32114(16) -0.00950(12) 0.0181(3) Uani 1 1 d .
N3 N 0.93787(14) 0.51519(19) 0.27664(14) 0.0264(3) Uani 1 1 d .
C1 C 0.69868(16) 0.17631(19) 0.19853(14) 0.0186(3) Uani 1 1 d .
C2 C 0.69912(15) 0.35105(19) 0.13788(15) 0.0179(3) Uani 1 1 d .
C3 C 0.74527(15) 0.25168(19) -0.04222(15) 0.0165(3) Uani 1 1 d .
C4 C 0.88967(16) 0.19672(19) 0.06024(14) 0.0166(3) Uani 1 1 d .
C5 C 0.91419(16) 0.1113(2) 0.18205(15) 0.0189(3) Uani 1 1 d .
C6 C 0.7815(2) -0.1058(2) 0.24046(18) 0.0276(4) Uani 1 1 d .
H6A H 0.7975 -0.1108 0.3364 0.041 Uiso 1 1 calc R
H6B H 0.8499 -0.1781 0.2308 0.041 Uiso 1 1 calc R
H6C H 0.6854 -0.1441 0.1770 0.041 Uiso 1 1 calc R
C7 C 0.83783(16) 0.4374(2) 0.21591(15) 0.0189(3) Uani 1 1 d .
C8 C 0.58715(17) 0.4631(2) 0.14364(18) 0.0232(3) Uani 1 1 d .
H8A H 0.5834 0.5700 0.0981 0.035 Uiso 1 1 calc R
H8B H 0.6114 0.4832 0.2409 0.035 Uiso 1 1 calc R
H8C H 0.4948 0.4080 0.0956 0.035 Uiso 1 1 calc R
C9 C 0.69478(16) 0.22929(19) -0.19497(15) 0.0179(3) Uani 1 1 d .
C10 C 0.56861(16) 0.3060(2) -0.28949(16) 0.0218(3) Uani 1 1 d .
H10 H 0.5160 0.3697 -0.2567 0.026 Uiso 1 1 calc R
C11 C 0.52009(17) 0.2889(2) -0.43182(16) 0.0261(4) Uani 1 1 d .
H11 H 0.4331 0.3389 -0.4960 0.031 Uiso 1 1 calc R
C12 C 0.59767(18) 0.1998(2) -0.48034(16) 0.0254(4) Uani 1 1 d .
H12 H 0.5651 0.1912 -0.5776 0.031 Uiso 1 1 calc R
C13 C 0.72235(17) 0.1233(2) -0.38801(16) 0.0236(3) Uani 1 1 d .
H13 H 0.7756 0.0624 -0.4217 0.028 Uiso 1 1 calc R
C14 C 0.77051(16) 0.1352(2) -0.24470(15) 0.0202(3) Uani 1 1 d .
H14 H 0.8547 0.0793 -0.1813 0.024 Uiso 1 1 calc R
C15 C 1.00502(16) 0.2404(2) 0.04092(14) 0.0178(3) Uani 1 1 d .
H15 H 0.9890 0.3013 -0.0399 0.021 Uiso 1 1 calc R
C16 C 1.14219(16) 0.1971(2) 0.13692(16) 0.0203(3) Uani 1 1 d .
C17 C 1.16259(16) 0.1121(2) 0.25623(15) 0.0230(3) Uani 1 1 d .
H17 H 1.2561 0.0813 0.3224 0.028 Uiso 1 1 calc R
C18 C 1.05273(17) 0.0704(2) 0.28299(16) 0.0226(3) Uani 1 1 d .
C19 C 1.26591(17) 0.2431(2) 0.11564(17) 0.0257(4) Uani 1 1 d .
H19A H 1.3082 0.1413 0.1015 0.039 Uiso 1 1 calc R
H19B H 1.3364 0.3027 0.1978 0.039 Uiso 1 1 calc R
H19C H 1.2338 0.3154 0.0337 0.039 Uiso 1 1 calc R
C20 C 1.08577(19) -0.0050(3) 0.42131(17) 0.0345(4) Uani 1 1 d .
H20A H 1.0693 -0.1259 0.4107 0.052 Uiso 1 1 calc R
H20B H 1.0246 0.0453 0.4549 0.052 Uiso 1 1 calc R
H20C H 1.1849 0.0167 0.4884 0.052 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 N1 C5 124.03(13)
C1 N1 C6 115.32(13)
C5 N1 C6 120.64(13)
C3 N2 C2 119.77(12)
O1 C1 N1 122.38(15)
O1 C1 C2 121.07(14)
N1 C1 C2 116.32(13)
N2 C2 C7 113.58(12)
N2 C2 C8 107.91(12)
C7 C2 C8 107.44(13)
N2 C2 C1 105.15(11)
C7 C2 C1 112.31(12)
C8 C2 C1 110.39(12)
N2 C3 C4 124.16(13)
N2 C3 C9 115.95(12)
C4 C3 C9 119.88(13)
C15 C4 C5 119.02(14)
C15 C4 C3 119.81(13)
C5 C4 C3 121.02(13)
C4 C5 C18 120.44(14)
C4 C5 N1 120.56(13)
C18 C5 N1 118.99(13)
N3 C7 C2 174.06(16)
C14 C9 C10 119.39(13)
C14 C9 C3 121.93(13)
C10 C9 C3 118.68(13)
C11 C10 C9 119.91(14)
C12 C11 C10 120.43(14)
C13 C12 C11 120.18(14)
C12 C13 C14 120.09(15)
C9 C14 C13 119.96(14)
C16 C15 C4 121.61(14)
C15 C16 C17 117.81(14)
C15 C16 C19 121.58(14)
C17 C16 C19 120.59(14)
C18 C17 C16 123.04(14)
C17 C18 C5 118.01(14)
C17 C18 C20 119.43(14)
C5 C18 C20 122.41(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2165(19)
N1 C1 1.361(2)
N1 C5 1.431(2)
N1 C6 1.465(2)
N2 C3 1.282(2)
N2 C2 1.4727(18)
N3 C7 1.143(2)
C1 C2 1.547(2)
C2 C7 1.490(2)
C2 C8 1.527(2)
C3 C4 1.485(2)
C3 C9 1.5009(19)
C4 C15 1.399(2)
C4 C5 1.405(2)
C5 C18 1.407(2)
C9 C14 1.396(2)
C9 C10 1.397(2)
C10 C11 1.393(2)
C11 C12 1.382(2)
C12 C13 1.380(2)
C13 C14 1.400(2)
C15 C16 1.387(2)
C16 C17 1.393(2)
C16 C19 1.502(2)
C17 C18 1.387(2)
C18 C20 1.505(2)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 N1 C1 O1 -175.73(13)
C6 N1 C1 O1 4.9(2)
C5 N1 C1 C2 9.70(19)
C6 N1 C1 C2 -169.68(13)
C3 N2 C2 C7 50.42(19)
C3 N2 C2 C8 169.42(13)
C3 N2 C2 C1 -72.75(16)
O1 C1 C2 N2 -107.44(14)
N1 C1 C2 N2 67.20(15)
O1 C1 C2 C7 128.58(15)
N1 C1 C2 C7 -56.78(16)
O1 C1 C2 C8 8.70(18)
N1 C1 C2 C8 -176.66(13)
C2 N2 C3 C4 0.2(2)
C2 N2 C3 C9 -178.88(13)
N2 C3 C4 C15 -131.65(16)
C9 C3 C4 C15 47.4(2)
N2 C3 C4 C5 43.8(2)
C9 C3 C4 C5 -137.18(15)
C15 C4 C5 C18 0.0(2)
C3 C4 C5 C18 -175.47(14)
C15 C4 C5 N1 179.09(13)
C3 C4 C5 N1 3.6(2)
C1 N1 C5 C4 -51.8(2)
C6 N1 C5 C4 127.55(16)
C1 N1 C5 C18 127.33(16)
C6 N1 C5 C18 -53.3(2)
N2 C3 C9 C14 -170.86(14)
C4 C3 C9 C14 10.0(2)
N2 C3 C9 C10 9.5(2)
C4 C3 C9 C10 -169.64(14)
C14 C9 C10 C11 -0.4(2)
C3 C9 C10 C11 179.26(15)
C9 C10 C11 C12 -1.5(3)
C10 C11 C12 C13 1.6(3)
C11 C12 C13 C14 0.2(3)
C10 C9 C14 C13 2.2(2)
C3 C9 C14 C13 -177.42(14)
C12 C13 C14 C9 -2.2(2)
C5 C4 C15 C16 2.0(2)
C3 C4 C15 C16 177.48(14)
C4 C15 C16 C17 -1.8(2)
C4 C15 C16 C19 179.59(14)
C15 C16 C17 C18 -0.4(2)
C19 C16 C17 C18 178.26(15)
C16 C17 C18 C5 2.2(2)
C16 C17 C18 C20 -173.48(16)
C4 C5 C18 C17 -2.0(2)
N1 C5 C18 C17 178.87(13)
C4 C5 C18 C20 173.58(16)
N1 C5 C18 C20 -5.6(2)
