#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:21:14 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180423 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/92/7209247.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_7209247
loop_
_publ_author_name
'Chęcińska, Lilianna'
'Morgenroth, Wolfgang'
'Paulmann, Carsten'
'Jayatilaka, Dylan'
'Dittrich, Birger'
_publ_section_title
;
 A comparison of electron density from Hirshfeld-atom refinement, X-ray
 wavefunction refinement and multipole refinement on three urea
 derivatives
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              2084
_journal_paper_doi               10.1039/c2ce26964c
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety         'C2 H6 N2 O'
_chemical_formula_sum            'C2 H6 N2 O'
_chemical_formula_weight         74.09
_chemical_name_common            N-methylurea
_chemical_name_systematic
;
N-methylurea
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           XD2006
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.741(1)
_cell_length_b                   6.743(1)
_cell_length_c                   8.580(2)
_cell_measurement_temperature    8(2)
_cell_volume                     390.00(12)
_computing_cell_refinement       'XDS (Kabsch, 1993; 2010)'
_computing_data_collection       'MarCCD (Paulmann & Morgenroth, 2006)'
_computing_data_reduction        'XDS (Kabsch, 1993; 2010)'
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      8(2)
_diffrn_detector_type            'MarCCD detector'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Huber diffractometer'
_diffrn_measurement_method       'φ scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.5166
_diffrn_reflns_av_R_equivalents  0.0829
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18822
_diffrn_reflns_theta_full        31.94
_diffrn_reflns_theta_max         31.94
_diffrn_reflns_theta_min         2.79
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             160
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.485
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1971
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.027
_refine_ls_R_factor_gt           0.027
_refine_ls_R_Fsqd_factor         0.051
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w2 = 1/[s²(Fo²)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.058
_reflns_number_gt                1920
_reflns_number_total             1985
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c2ce26964c.txt
_cod_data_source_block           murea
_cod_database_code               7209247
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 -X,1/2+Y,1/2-Z
4 1/2+X,1/2-Y,-Z
loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) C(1) Z O(1) N(1) Y
N(1) C(1) X N(1) C(11) Y
N(2) C(1) X N(2) H(2A) Y
C(1) O(1) Z C(1) N(2) Y
C(11) N(1) Z C(11) H(11A) Y
H(1) N(1) Z H(1) C(1) Y
H(2A) N(2) Z H(2A) C(1) Y
H(2B) N(2) Z H(2B) C(1) Y
H(11A) C(11) Z H(11A) H(11C) Y
H(11B) C(11) Z H(11B) H(11A) Y
H(11C) C(11) Z H(11C) H(11B) Y
loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
O(1) 6.29(5) 0 0.002(11) 0.014(11) -0.035(14) 0.014(14) -0.025(11) 0.003(12)
-0.057(13) 0.002(12) 0.061(11) -0.009(10) 0.020(10) 0.011(12) -0.013(11)
-0.002(10) -0.008(10) 0.059(14) -0.013(12) -0.007(12) -0.011(13) -0.014(12)
-0.003(12) -0.001(12) -0.000(12) -0.008(11) 0.983(4) 1 1 1 1 1 2 4.466 2 4.466
2 4.466 3 4.466 4 4.466
N(1) 5.07(7) 0 0.038(15) -0.010(16) 0 0.006(15) 0 0 -0.008(14) 0.033(14) 0
0.010(14) -0.003(13) 0 0 0.157(14) 0.023(12) 0.026(18) 0 0 0.012(16) 0.010(17)
0 0 0.010(15) -0.036(15) 0.994(5) 1 1 1 1 1 2 3.83936 2 3.83936 2 3.83936 3
3.83936 4 3.83936
N(2) 5.22(5) 0 -0.030(15) 0.006(15) 0 -0.008(15) 0 0 -0.021(14) -0.006(14) 0
0.016(13) -0.011(13) 0 0 0.168(14) -0.012(12) 0.003(18) 0 0 -0.020(18)
0.026(17) 0 0 -0.027(15) 0.011(15) 0.981326 1 1 1 1 1 2 3.83936 2 3.83936 2
3.83936 3 3.83936 4 3.83936
C(1) 3.75(9) 0 0 0 0.02(2) 0.168(19) 0 0 -0.204(17) 0 0.22(2) 0 0 0.22(2) 0 0 0
-0.05(3) 0 0 -0.03(2) 0 0 0 -0.06(2) 0 1.001(11) 1 1 1 1 1 2 3.1762 2 3.1762 2
3.1762 3 3.1762 4 3.1762
C(11) 3.88(12) 0 0 0 -0.068(19) -0.041(19) 0 0 0 0 0.27(2) 0 0 0 0 0.035(16)
-0.15(2) 0.04(2) 0 0 0 0 0.02(2) 0.09(2) 0 0 1.003(12) 1 1 1 1 1 2 3.1762 2
3.1762 2 3.1762 3 3.1762 4 3.1762
H(1) 0.97(4) 0 0 0 0.18(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29
1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2
H(2A) 0.90(3) 0 0 0 0.17(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29
1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2
H(2B) 0.84(3) 0 0 0 0.14(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29
1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2
H(11A) 1.03(3) 0 0 0 0.118(16) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13
1.29 1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2
H(11B) 1.027 0 0 0 0.1184 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29
1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2
H(11C) 1.027 0 0 0 0.1184 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.13 1.29
1.29 1.29 1.29 1.29 0 2 1 2 2 2 3 2 4 2
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_U_iso_or_equiv
O(1) 0.37477(6) 0.45323(6) 0.19580(5) 1 4 0.006
N(1) 0.20093(5) 0.34040(6) 0.40523(5) 1 4 0.007
N(2) 0.33986(5) 0.65183(6) 0.40862(5) 1 4 0.008
C(1) 0.30810(5) 0.48052(5) 0.33079(4) 1 4 0.005
C(11) 0.14256(6) 0.15878(6) 0.32753(5) 1 4 0.009
H(1) 0.145272 0.378126 0.510382 1 4 0.026
H(2A) 0.282358 0.663272 0.51693 1 4 0.027
H(2B) 0.431948 0.752446 0.360145 1 4 0.020
H(11A) 0.084332 0.06202 0.414586 1 4 0.032
H(11B) 0.036694 0.183991 0.237348 1 4 0.032
H(11C) 0.27057 0.087462 0.280738 1 4 0.031
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(1) N(1) C(11) 121.28(4) 1_555 1_555 1_555 yes
C(1) N(1) H(1) 116.44 1_555 1_555 1_555 yes
C(11) N(1) H(1) 121.55 1_555 1_555 1_555 yes
C(1) N(2) H(2A) 117.34 1_555 1_555 1_555 yes
C(1) N(2) H(2B) 117.93 1_555 1_555 1_555 yes
H(2A) N(2) H(2B) 124.33 1_555 1_555 1_555 yes
O(1) C(1) N(1) 121.68(4) 1_555 1_555 1_555 yes
O(1) C(1) N(2) 121.62(4) 1_555 1_555 1_555 yes
N(1) C(1) N(2) 116.70(4) 1_555 1_555 1_555 yes
N(1) C(11) H(11A) 107.14 1_555 1_555 1_555 yes
N(1) C(11) H(11B) 112.39 1_555 1_555 1_555 yes
N(1) C(11) H(11C) 109.55 1_555 1_555 1_555 yes
H(11A) C(11) H(11B) 111.06 1_555 1_555 1_555 yes
H(11A) C(11) H(11C) 106.59 1_555 1_555 1_555 yes
H(11B) C(11) H(11C) 109.89 1_555 1_555 1_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(1) 1.2559(5) 1_555 1_555 yes
N(1) C(1) 1.3500(5) 1_555 1_555 yes
N(1) C(11) 1.4488(6) 1_555 1_555 yes
N(1) H(1) 1.0097 1_555 1_555 yes
N(2) C(1) 1.3513(5) 1_555 1_555 yes
N(2) H(2A) 1.0098 1_555 1_555 yes
N(2) H(2B) 1.009 1_555 1_555 yes
C(11) H(11A) 1.0666 1_555 1_555 yes
C(11) H(11B) 1.0663 1_555 1_555 yes
C(11) H(11C) 1.0663 1_555 1_555 yes
