#------------------------------------------------------------------------------
#$Date: 2018-10-05 15:19:55 +0300 (Fri, 05 Oct 2018) $
#$Revision: 211332 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/45/7204534.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_7204534
loop_
_publ_author_name
'Bulman Page, Philip C.'
'Allin, Steven M.'
'Maddocks, Suzanne J.'
'Elsegood, Mark R. J.'
_publ_section_title
;
 New ligands for asymmetric diethylzinc additions to aromatic
 aldehydes, demonstrating substrate-dependent nonlinear effects
;
_journal_issue                   24
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2827
_journal_paper_doi               10.1039/b208810j
_journal_year                    2002
_chemical_formula_sum            'C15 H15 N O'
_chemical_formula_weight         225.28
_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 for ArH, free xyz for others'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'all non-H atoms found by direct methods'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.650(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.2981(6)
_cell_length_b                   10.1999(9)
_cell_length_c                   8.6263(8)
_cell_measurement_reflns_used    4698
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.72
_cell_measurement_theta_min      2.48
_cell_volume                     611.91(9)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.934
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5345
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.71
_diffrn_reflns_theta_min         2.48
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Sheldrick, G.M.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.90
_exptl_crystal_size_mid          0.49
_exptl_crystal_size_min          0.45
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(10)
_refine_ls_extinction_coef       0.013(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2768
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0295
_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)+(0.0477P)²+0.0836P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                2680
_reflns_number_total             2768
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            b208810j.txt
_cod_data_source_block           2
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7204534
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
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.36492(16) 0.39844(11) 0.48216(14) 0.0300(2) Uani 1 1 d . . .
H1A H 0.370(3) 0.329(2) 0.549(2) 0.045 Uiso 1 1 d . . .
C1 C 0.27148(18) 0.35367(13) 0.31289(18) 0.0331(3) Uani 1 1 d . . .
H1C H 0.195(3) 0.4228(19) 0.241(2) 0.040 Uiso 1 1 d . . .
H1D H 0.222(2) 0.264(2) 0.304(2) 0.040 Uiso 1 1 d . . .
C2 C 0.48209(15) 0.36780(11) 0.37425(13) 0.0218(2) Uani 1 1 d . . .
H2 H 0.549(2) 0.4450(16) 0.3432(18) 0.026 Uiso 1 1 d . . .
C3 C 0.61181(15) 0.24751(10) 0.40642(13) 0.0197(2) Uani 1 1 d . . .
O1 O 0.51053(12) 0.14826(8) 0.46221(10) 0.02453(18) Uani 1 1 d . . .
H1B H 0.571(3) 0.077(2) 0.469(2) 0.037 Uiso 1 1 d . . .
C4 C 0.64126(15) 0.21247(11) 0.24280(13) 0.0213(2) Uani 1 1 d . . .
C5 C 0.76478(17) 0.28820(13) 0.18304(15) 0.0277(2) Uani 1 1 d . . .
H5 H 0.8373 0.3568 0.2477 0.033 Uiso 1 1 calc R . .
C6 C 0.7821(2) 0.26353(15) 0.02903(16) 0.0357(3) Uani 1 1 d . . .
H6 H 0.8648 0.3162 -0.0114 0.043 Uiso 1 1 calc R . .
C7 C 0.6785(2) 0.16209(16) -0.06528(15) 0.0372(3) Uani 1 1 d . . .
H7 H 0.6894 0.1456 -0.1705 0.045 Uiso 1 1 calc R . .
C8 C 0.5595(2) 0.08538(14) -0.00494(15) 0.0330(3) Uani 1 1 d . . .
H8 H 0.4912 0.0145 -0.0681 0.040 Uiso 1 1 calc R . .
C9 C 0.53890(16) 0.11094(12) 0.14747(14) 0.0259(2) Uani 1 1 d . . .
H9 H 0.4545 0.0588 0.1865 0.031 Uiso 1 1 calc R . .
C10 C 0.80523(15) 0.27418(11) 0.53599(13) 0.0213(2) Uani 1 1 d . . .
C11 C 0.84870(17) 0.39178(11) 0.62165(14) 0.0247(2) Uani 1 1 d . . .
H11 H 0.7581 0.4615 0.5976 0.030 Uiso 1 1 calc R . .
C12 C 1.02466(18) 0.40790(12) 0.74265(14) 0.0283(3) Uani 1 1 d . . .
H12 H 1.0535 0.4887 0.7996 0.034 Uiso 1 1 calc R . .
C13 C 1.15742(18) 0.30655(13) 0.77997(15) 0.0311(3) Uani 1 1 d . . .
H13 H 1.2763 0.3171 0.8633 0.037 Uiso 1 1 calc R . .
C14 C 1.11501(18) 0.18906(14) 0.69418(16) 0.0322(3) Uani 1 1 d . . .
H14 H 1.2055 0.1193 0.7190 0.039 Uiso 1 1 calc R . .
C15 C 0.94103(18) 0.17338(12) 0.57249(15) 0.0276(3) Uani 1 1 d . . .
H15 H 0.9143 0.0933 0.5136 0.033 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 59.70(8) . . ?
C2 C1 N1 59.88(8) . . ?
C1 C2 N1 60.42(8) . . ?
C1 C2 C3 120.66(10) . . ?
N1 C2 C3 120.18(10) . . ?
O1 C3 C2 106.10(8) . . ?
O1 C3 C4 112.23(9) . . ?
C2 C3 C4 105.84(8) . . ?
O1 C3 C10 109.72(9) . . ?
C2 C3 C10 111.92(9) . . ?
C4 C3 C10 110.91(8) . . ?
C9 C4 C5 118.94(10) . . ?
C9 C4 C3 121.19(10) . . ?
C5 C4 C3 119.77(10) . . ?
C6 C5 C4 120.39(12) . . ?
C7 C6 C5 120.11(12) . . ?
C8 C7 C6 119.56(12) . . ?
C7 C8 C9 120.63(12) . . ?
C4 C9 C8 120.35(11) . . ?
C11 C10 C15 118.83(10) . . ?
C11 C10 C3 123.32(10) . . ?
C15 C10 C3 117.81(10) . . ?
C10 C11 C12 120.46(11) . . ?
C13 C12 C11 120.34(11) . . ?
C12 C13 C14 119.41(11) . . ?
C15 C14 C13 120.35(12) . . ?
C14 C15 C10 120.60(11) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.4759(15) . ?
N1 C1 1.4839(19) . ?
C1 C2 1.4731(16) . ?
C2 C3 1.5230(15) . ?
C3 O1 1.4208(12) . ?
C3 C4 1.5329(14) . ?
C3 C10 1.5359(15) . ?
C4 C9 1.3908(16) . ?
C4 C5 1.3990(16) . ?
C5 C6 1.3949(16) . ?
C6 C7 1.390(2) . ?
C7 C8 1.382(2) . ?
C8 C9 1.3926(17) . ?
C10 C11 1.3941(16) . ?
C10 C15 1.3962(16) . ?
C11 C12 1.3974(17) . ?
C12 C13 1.3863(18) . ?
C13 C14 1.3931(19) . ?
C14 C15 1.3898(17) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1B N1 0.84(2) 1.89(2) 2.6990(14) 159.2(17) 2_646
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21189872
