#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:24:29 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178468 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/89/4028957.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4028957
loop_
_publ_author_name
'Andreu, Raquel'
'Carrasquer, Laura'
'Franco, Santiago'
'Garín, Javier'
'Orduna, Jesús'
'Martínez de Baroja, Natalia'
'Alicante, Raquel'
'Villacampa, Belén'
'Allain, Magali'
_publ_section_title
;
 4H-Pyran-4-ylidenes: Strong Proaromatic Donors for Organic Nonlinear
 Optical Chromophores
;
_journal_issue                   17
_journal_name_full               'The Journal of Organic Chemistry'
_journal_page_first              6647
_journal_page_last               6657
_journal_paper_doi               10.1021/jo901142f
_journal_volume                  74
_journal_year                    2009
_chemical_formula_moiety         'C24 H27 N1 O3'
_chemical_formula_sum            'C24 H27 N O3'
_chemical_formula_weight         377.47
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_date             2009-05-07T18:08:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 91.12(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.340(1)
_cell_length_b                   12.560(1)
_cell_length_c                   16.843(2)
_cell_measurement_reflns_used    7883
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.7
_cell_measurement_theta_min      2
_cell_volume                     2187.0(4)
_computing_cell_refinement       'SELECT,CELL, STOE IPDS'
_computing_data_collection       'EXPOSE, STOE IPDS'
_computing_data_reduction        'INTEGRATE, STOE IPDS'
_computing_molecular_graphics    'DIAMOND 3.1 (Crystal Impact GbR 2004)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'Direct methods (Sir92,Altomare et al.,1993)'
_diffrn_detector_area_resol_mean 6.66
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'Oscillation Phi Incr 1.4 deg'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16867
_diffrn_reflns_theta_full        25.86
_diffrn_reflns_theta_max         25.86
_diffrn_reflns_theta_min         2.02
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.146
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.115
_refine_diff_density_min         -0.11
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.881
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.881
_refine_ls_R_factor_gt           0.044
_refine_ls_shift/su_max          0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0553P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1139
_reflns_number_gt                2208
_reflns_number_total             4188
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo901142fsup2.cif
_cod_data_source_block           msz12
_cod_database_code               4028957
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_calc_flag
_atom_site_refinement_flags
C01 C 1.05025(17) 0.06960(14) 0.88273(9) 0.0537(4) Uani 1 d .
H01 H 1.1391 0.0722 0.8922 0.064 Uiso 1 calc R
C02 C 0.97061(18) 0.11741(13) 0.93796(9) 0.0524(4) Uani 1 d .
H02 H 0.8827 0.1203 0.9253 0.063 Uiso 1 calc R
C03 C 1.00968(17) 0.16100(14) 1.00976(9) 0.0530(4) Uani 1 d .
C04 C 1.1412(2) 0.16718(16) 1.03956(11) 0.0653(5) Uani 1 d .
C05 C 0.9343(2) 0.21119(13) 1.06937(9) 0.0567(5) Uani 1 d .
C06 C 0.7926(2) 0.21926(14) 1.07571(9) 0.0592(5) Uani 1 d .
C07 C 0.7365(2) 0.30670(17) 1.11172(11) 0.0781(6) Uani 1 d .
H07 H 0.788 0.3634 1.1284 0.094 Uiso 1 calc R
C08 C 0.6047(3) 0.3101(2) 1.12300(13) 0.0898(7) Uani 1 d .
H08 H 0.5686 0.3691 1.1474 0.108 Uiso 1 calc R
C09 C 0.5268(2) 0.2285(2) 1.09897(12) 0.0852(7) Uani 1 d .
H09 H 0.4381 0.2315 1.1069 0.102 Uiso 1 calc R
C10 C 0.5807(2) 0.14184(19) 1.06293(11) 0.0783(6) Uani 1 d .
H10 H 0.5281 0.0858 1.0461 0.094 Uiso 1 calc R
C11 C 0.7125(2) 0.13683(16) 1.05132(10) 0.0653(5) Uani 1 d .
H11 H 0.7478 0.0774 1.0269 0.078 Uiso 1 calc R
C12 C 1.00599(16) 0.01812(13) 0.81415(9) 0.0485(4) Uani 1 d .
C13 C 1.09400(16) -0.03788(13) 0.76528(9) 0.0507(4) Uani 1 d .
H13 H 1.1821 -0.0343 0.7772 0.061 Uiso 1 calc R
C14 C 1.05348(16) -0.09550(14) 0.70281(9) 0.0507(4) Uani 1 d .
C15 C 0.87375(16) 0.01236(13) 0.78875(9) 0.0509(4) Uani 1 d .
H15 H 0.8117 0.0495 0.8169 0.061 Uiso 1 calc R
C16 C 0.83676(16) -0.04530(14) 0.72529(9) 0.0510(4) Uani 1 d .
C17 C 1.13186(17) -0.16320(15) 0.64756(10) 0.0595(5) Uani 1 d .
C18 C 1.27457(19) -0.1587(2) 0.66978(13) 0.0913(7) Uani 1 d .
H18A H 1.3223 -0.2023 0.6339 0.137 Uiso 1 calc R
H18B H 1.2873 -0.1844 0.723 0.137 Uiso 1 calc R
H18C H 1.3044 -0.0865 0.6665 0.137 Uiso 1 calc R
C19 C 1.1122(2) -0.12094(19) 0.56267(10) 0.0863(7) Uani 1 d .
H19A H 1.161 -0.1636 0.5267 0.13 Uiso 1 calc R
H19B H 1.1412 -0.0484 0.5602 0.13 Uiso 1 calc R
H19C H 1.0221 -0.1243 0.5481 0.13 Uiso 1 calc R
C20 C 1.0842(2) -0.27827(17) 0.65228(14) 0.0865(7) Uani 1 d .
H20A H 1.1331 -0.3219 0.617 0.13 Uiso 1 calc R
H20B H 0.9943 -0.2812 0.6371 0.13 Uiso 1 calc R
H20C H 1.0952 -0.3039 0.7057 0.13 Uiso 1 calc R
C21 C 0.70243(18) -0.06325(17) 0.69213(11) 0.0673(5) Uani 1 d .
C22 C 0.6953(2) -0.0253(2) 0.60541(13) 0.1129(10) Uani 1 d .
H22A H 0.6096 -0.0368 0.5842 0.169 Uiso 1 calc R
H22B H 0.7563 -0.0645 0.5747 0.169 Uiso 1 calc R
H22C H 0.7155 0.0493 0.6032 0.169 Uiso 1 calc R
C23 C 0.6734(2) -0.1830(2) 0.69664(16) 0.0988(8) Uani 1 d .
H23A H 0.5878 -0.1964 0.6759 0.148 Uiso 1 calc R
H23B H 0.6792 -0.206 0.7509 0.148 Uiso 1 calc R
H23C H 0.7351 -0.2215 0.6659 0.148 Uiso 1 calc R
C24 C 0.60321(19) -0.0017(2) 0.74000(15) 0.0973(8) Uani 1 d .
H24A H 0.5182 -0.0145 0.7182 0.146 Uiso 1 calc R
H24B H 0.6221 0.073 0.7376 0.146 Uiso 1 calc R
H24C H 0.607 -0.0251 0.7943 0.146 Uiso 1 calc R
N01 N 1.00641(18) 0.24945(14) 1.12714(9) 0.0744(5) Uani 1 d .
O01 O 0.92563(11) -0.09927(10) 0.68244(6) 0.0575(3) Uani 1 d .
O02 O 1.13841(14) 0.22508(11) 1.10913(7) 0.0790(4) Uani 1 d .
O03 O 1.24348(15) 0.13257(13) 1.01648(8) 0.0842(5) Uani 1 d .
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 0 '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 0.006 '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
C02 C01 C12 124.45(17)
C03 C02 C01 126.17(17)
C02 C03 C05 129.47(17)
C02 C03 C04 125.73(17)
C05 C03 C04 104.78(15)
O03 C04 O02 119.53(19)
O03 C04 C03 133.65(18)
O02 C04 C03 106.81(18)
N01 C05 C03 111.96(18)
N01 C05 C06 118.34(16)
C03 C05 C06 129.60(15)
C11 C06 C07 118.0(2)
C11 C06 C05 121.12(17)
C07 C06 C05 120.71(18)
C08 C07 C06 120.5(2)
C09 C08 C07 121.1(2)
C08 C09 C10 119.1(2)
C09 C10 C11 120.7(2)
C10 C11 C06 120.67(19)
C01 C12 C13 120.32(16)
C01 C12 C15 124.72(16)
C13 C12 C15 114.90(14)
C14 C13 C12 121.86(16)
C13 C14 O01 120.35(15)
C13 C14 C17 128.79(16)
O01 C14 C17 110.86(14)
C16 C15 C12 121.56(15)
C15 C16 O01 120.47(15)
C15 C16 C21 128.62(16)
O01 C16 C21 110.90(14)
C14 C17 C18 111.02(15)
C14 C17 C20 108.84(14)
C18 C17 C20 109.61(18)
C14 C17 C19 108.47(15)
C18 C17 C19 109.12(16)
C20 C17 C19 109.77(17)
C16 C21 C24 110.68(16)
C16 C21 C23 107.97(16)
C24 C21 C23 109.59(18)
C16 C21 C22 109.46(17)
C24 C21 C22 108.94(19)
C23 C21 C22 110.19(18)
C05 N01 O02 107.19(15)
C14 O01 C16 120.80(12)
C04 O02 N01 109.08(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C01 C02 1.391(2)
C01 C12 1.393(2)
C02 C03 1.381(2)
C03 C05 1.430(2)
C03 C04 1.442(3)
C04 O03 1.215(2)
C04 O02 1.380(2)
C05 N01 1.306(2)
C05 C06 1.474(3)
C06 C11 1.383(3)
C06 C07 1.387(3)
C07 C08 1.380(3)
C08 C09 1.360(3)
C09 C10 1.370(3)
C10 C11 1.382(3)
C12 C13 1.425(2)
C12 C15 1.427(2)
C13 C14 1.338(2)
C14 O01 1.3601(19)
C14 C17 1.508(2)
C15 C16 1.341(2)
C16 O01 1.3605(19)
C16 C21 1.504(2)
C17 C18 1.516(3)
C17 C20 1.530(3)
C17 C19 1.535(2)
C21 C24 1.527(3)
C21 C23 1.536(3)
C21 C22 1.537(3)
N01 O02 1.437(2)
