#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:36:08 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180400 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/69/7206936.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_7206936
loop_
_publ_author_name
'Spingler, Bernhard'
'Schnidrig, Stephan'
'Todorova, Tonya'
'Wild, Ferdinand'
_publ_section_title
;
 Some thoughts about the single crystal growth of small molecules
;
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              751
_journal_paper_doi               10.1039/c1ce05624g
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C24 H22 N4 O4'
_chemical_formula_weight         430.46
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 98.085(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.3329(2)
_cell_length_b                   12.7049(3)
_cell_length_c                   9.1195(2)
_cell_measurement_reflns_used    7141
_cell_measurement_temperature    183(2)
_cell_measurement_theta_max      32.6893
_cell_measurement_theta_min      2.7202
_cell_volume                     1070.58(4)
_computing_cell_refinement       'CrysAlisPro (Oxford, 2007)'
_computing_data_collection       'CrysAlisPro (Oxford, 2007)'
_computing_data_reduction        'CrysAlisPro (Oxford, 2007)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-97 (Altomare, 1999)'
_diffrn_ambient_temperature      183(2)
_diffrn_detector_area_resol_mean 10.4498
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_device_type  'Oxford Xcalibur Ruby CCD'
_diffrn_measurement_method       'ο oscillation scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14471
_diffrn_reflns_theta_full        30.44
_diffrn_reflns_theta_max         32.76
_diffrn_reflns_theta_min         2.73
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_correction_T_min  0.7360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug 3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3660
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0636P)²+0.2695P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1216
_refine_ls_wR_factor_ref         0.1294
_reflns_number_gt                3116
_reflns_number_total             3660
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1ce05624g.txt
_cod_data_source_block           bs071011
_cod_original_cell_volume        1070.59(4)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7206936
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
C2 C 0.99316(10) 0.05717(7) 0.99545(10) 0.02022(18) Uani 1 1 d .
C3 C 0.87413(10) 0.12662(7) 0.96459(10) 0.02056(18) Uani 1 1 d .
C4 C 0.93251(10) 0.23153(7) 0.97222(11) 0.02191(19) Uani 1 1 d .
C5 C 1.08023(11) 0.22206(7) 1.00530(12) 0.0264(2) Uani 1 1 d .
H5A H 1.1474 0.2786 1.0164 0.032 Uiso 1 1 calc R
C6 C 0.86144(11) 0.33569(7) 0.95676(11) 0.02233(19) Uani 1 1 d .
C7 C 0.76356(12) 0.36880(8) 1.04920(12) 0.0288(2) Uani 1 1 d .
H7A H 0.7342 0.3222 1.1209 0.035 Uiso 1 1 calc R
C8 C 0.70941(13) 0.47041(9) 1.03554(14) 0.0331(2) Uani 1 1 d .
H8A H 0.6428 0.4914 1.0997 0.040 Uiso 1 1 calc R
C10 C 0.83949(15) 0.50847(9) 0.84998(13) 0.0360(3) Uani 1 1 d .
H10A H 0.8670 0.5569 0.7796 0.043 Uiso 1 1 calc R
C11 C 0.90010(13) 0.40842(8) 0.85516(12) 0.0297(2) Uani 1 1 d .
H11A H 0.9671 0.3899 0.7901 0.036 Uiso 1 1 calc R
C12 C 0.72112(10) 0.09986(8) 0.92322(11) 0.02343(19) Uani 1 1 d .
C15 C 0.48603(12) 0.16686(9) 0.83969(15) 0.0356(3) Uani 1 1 d .
H15A H 0.4437 0.1294 0.9186 0.043 Uiso 1 1 calc R
H15B H 0.4705 0.1237 0.7485 0.043 Uiso 1 1 calc R
C16 C 0.41703(15) 0.27249(11) 0.8120(2) 0.0500(4) Uani 1 1 d .
H16A H 0.4291 0.3131 0.9043 0.075 Uiso 1 1 calc R
H16B H 0.3137 0.2636 0.7765 0.075 Uiso 1 1 calc R
H16C H 0.4631 0.3100 0.7372 0.075 Uiso 1 1 calc R
N1 N 1.11417(9) 0.11770(6) 1.01945(10) 0.02520(19) Uani 1 1 d .
H1A H 1.2027 0.0929 1.0412 0.030 Uiso 1 1 calc R
N9 N 0.74520(12) 0.54089(7) 0.93747(12) 0.0353(2) Uani 1 1 d .
O13 O 0.66724(9) 0.01199(6) 0.91840(12) 0.0378(2) Uani 1 1 d .
O14 O 0.64014(8) 0.18467(6) 0.88512(9) 0.02837(18) Uani 1 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 0.0000 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_3
N1 C2 C3 106.89(8) .
N1 C2 C2 119.35(10) 3_757
C3 C2 C2 133.76(11) 3_757
C2 C3 C4 106.66(8) .
C2 C3 C12 128.01(8) .
C4 C3 C12 125.22(8) .
C5 C4 C3 106.92(8) .
C5 C4 C6 121.47(9) .
C3 C4 C6 131.56(9) .
N1 C5 C4 108.54(8) .
C11 C6 C7 117.14(9) .
C11 C6 C4 120.21(9) .
C7 C6 C4 122.45(9) .
C8 C7 C6 119.28(10) .
N9 C8 C7 124.08(11) .
N9 C10 C11 124.20(11) .
C10 C11 C6 119.19(10) .
O13 C12 O14 120.88(9) .
O13 C12 C3 127.03(9) .
O14 C12 C3 112.07(8) .
O14 C15 C16 107.04(10) .
C2 N1 C5 110.98(8) .
C10 N9 C8 116.11(10) .
C12 O14 C15 116.67(8) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 N1 1.3584(12) .
C2 C3 1.4156(12) .
C2 C2 1.4596(18) 3_757
C3 C4 1.4379(13) .
C3 C12 1.4649(13) .
C4 C5 1.3745(14) .
C4 C6 1.4780(13) .
C5 N1 1.3651(12) .
C6 C11 1.3916(14) .
C6 C7 1.3924(14) .
C7 C8 1.3855(15) .
C8 N9 1.3406(16) .
C10 N9 1.3335(17) .
C10 C11 1.3894(15) .
C12 O13 1.2227(12) .
C12 O14 1.3338(11) .
C15 O14 1.4574(13) .
C15 C16 1.4946(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
N1 H1A O13 0.88 1.81 2.6216(11) 153.2 3_757
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
_geom_torsion_site_symmetry_1
N1 C2 C3 C4 -0.12(10) .
C2 C2 C3 C4 -179.90(13) 3_757
N1 C2 C3 C12 176.29(9) .
C2 C2 C3 C12 -3.5(2) 3_757
C2 C3 C4 C5 0.43(11) .
C12 C3 C4 C5 -176.11(9) .
C2 C3 C4 C6 -177.01(10) .
C12 C3 C4 C6 6.46(17) .
C3 C4 C5 N1 -0.58(12) .
C6 C4 C5 N1 177.17(9) .
C5 C4 C6 C11 56.72(14) .
C3 C4 C6 C11 -126.15(12) .
C5 C4 C6 C7 -117.89(12) .
C3 C4 C6 C7 59.23(15) .
C11 C6 C7 C8 0.40(16) .
C4 C6 C7 C8 175.17(10) .
C6 C7 C8 N9 0.01(18) .
N9 C10 C11 C6 0.25(19) .
C7 C6 C11 C10 -0.51(16) .
C4 C6 C11 C10 -175.41(10) .
C2 C3 C12 O13 5.80(18) .
C4 C3 C12 O13 -178.41(10) .
C2 C3 C12 O14 -172.58(9) .
C4 C3 C12 O14 3.21(14) .
C3 C2 N1 C5 -0.24(11) .
C2 C2 N1 C5 179.58(11) 3_757
C4 C5 N1 C2 0.52(12) .
C11 C10 N9 C8 0.16(19) .
C7 C8 N9 C10 -0.29(18) .
O13 C12 O14 C15 0.61(15) .
C3 C12 O14 C15 179.10(9) .
C16 C15 O14 C12 176.46(11) .
